(This entire novel available at www.cafeboudoir.com and www.lulu.com/jmplays - thanks for reading)
Chapter Four – Snowed Out
My trip home that day was filled with dread and apprehension, for good reason as it turns out. I'm not sure it was the day my life changed forever, although I suppose it’s debatable. I think my life officially changed the day that blonde fucking bitch Carissa Taylor walked into my life. What happened on this snowy January day was only a result of her arrival two months prior.
When we got back to Boston, it was snowing like crazy. It's a wonder the plane was even able to land. I guess we barely got in before the bulk of the storm hit, but by the time I got into the cab, traffic was bumper to bumper. There was almost a half-foot of white powder on the ground and the snow fell sideways. It took me nearly three hours to get home. I noticed an extra Mercedes parked next to my wife's little Mercedes convertible. Hmm, I wondered what was up with that.
When I walked in, I saw my wife sitting on the couch with her lawyer, Anna Goldberg. They both had stern looks on their faces. Anna was not only my wife's lawyer; she was also a shopping buddy. Anna was a short brunette, a little bit stocky, but she always dressed well. Today she wore a black pants suit, with ankle-high boots, and an orange scarf around her neck. Scrutinizing her more carefully, I caught an almost satisfied look on her face. I knew the bitch never liked me. My wife comes from a wealthy family, so when I married her, she insisted on an ironclad prenuptial agreement. Anna came from the best law firm in the city and specialized in these types of agreements. Basically, I had no rights at all. My wife got virtually everything if we separated. At the time, I was so desperate to marry Lydia that I didn't care. We were in love, or so I thought, and she was really fucking good in bed. I never lasted more than five minutes with her.
My wife got up off the couch and slapped me hard across the face. "What a loser I married," she said.
"Honey, I'm sorry," I said. "I made a mistake."
"Oh, I should say you made a mistake. How many mistakes like this have you made?"
"I don't know."
"I don't know," she repeated my words and slapped my face again. For some reason, she didn't look upset. Not only was she not crying, but she seemed oddly energized. Even though she probably hadn't left the house, she wore a ruffled skirt, a blouse and high heels. Lydia almost always wore heels.
"Read him the riot act, Anna."
"Charley," said Anna. "Lydia has asked me to stay and give you the following ultimatum. I have the divorce documents all drawn up. You can sign here. As you know, Lydia would get the house, the savings, as well as 75% of your income for the next five years. Not so good for you."
I swear the little cunt smirked as she said it. To my utter shock, Lydia was unable to hold back a grin. She wasn't the least bit upset about me sleeping around!
"Oh my god," I said, putting my hands to my head and sitting down. "I'm screwed."
"That's right," said Lydia.
They let me gain my composure before Lydia said, "Dearest Charley, I don't want you to think I'm unreasonable or unfair. There is another option. Anna, if you would please."
"My pleasure, Lydia. Charley, Lydia has graciously given you an option. It's an option I have employed for my female clients in the past. It has saved marriages."
I perked up. I needed this marriage at all costs. The alternative was not an option. I had seen poor single men and I was hell bent on not becoming one.
Anna continued: "I should add this is a particularly harsh version of this type of contract, but I think it's quite fitting given your past transgressions and some of the things Lydia has shared with me about you, Charley. Plus you don't really have much of a choice now, do you?"
Who was this annoying little tart to talk to me that way? It occurred to me that women were becoming increasingly invasive in my life. I used to rule over women, but I wasn't sure it was the case any longer.
"Go ahead, read me the riot act." I said.
"Very well," Anna said. She began reading, as I sat there increasingly stunned at the ridiculous conditions the women had designed for me to stay married. What was even worse is that both Lydia and Anna had big smiles on their faces as they read their insane manifesto:
Anna: "In order to stay married to Lydia, I, Charley agree to the following set of rules.
1. All decision making and authority in the marriage is yielded 100%, without exception, to Lydia.
2. Since all authority now lies with Lydia, all of Charley' earnings are to be deposited directly into Lydia's bank account. Lydia to provide Charley with a small weekly allowance based on good behavior.
3. Charley is responsible for all tasks, chores, and errands. This includes, but is not limited to all forms of cleaning, dishes, floors, bathrooms, laundry, yard work, etc.
4. Any failure to comply with Lydia's commands can and will result in punishment. Punishment to be in the form of removal of privileges, as well as corporal, bare-assed spanking, and other forms of humiliation as determined by Lydia.
5. Charley to wear a chastity belt on his penis at all times. It is not to be removed under any circumstances without the authorization of Lydia, or Carissa Taylor, Charley's boss, who will also hold a key to help ensure greater compliance at the work place.
6. Charley is no longer permitted to wear clothing while at home, unless advised under specific instructions from Lydia, to wear an outfit of her choosing.
7. Charley to treat all women with complete deference, obedience, and respect, since they are the superior gender.
Any serious violation of said rules will result in immediate forfeiture of marriage rights and removal from Lydia's household at Lydia's ultimate discretion."
The two females looked up at me for my reaction.
WHAT THE FUCK!!??! Things in my life had gone from bad to worse! My wife was now telling me that I had to basically become her live-in slave if I was going to stay married. I felt the sweat pouring down my armpits and my chest. Yet, very oddly, for reasons I couldn't explain at the time, I also felt the tiniest bit of arousal. I chose to ignore it.
"Honey, this is crazy. C'mon."
Anna cut in: "No. What's crazy is the way you’ve treated women over the years, especially your wife. Now you need to pay the piper."
I stomped my feet and took my jacket and hurled it onto the floor.
"That's it, take a big temper tantrum." said Lydia. "It's clear he's made his choice. Draw up the divorce papers, Anna."
"Certainly," she said.
"Wait!" I said.
"No," said Lydia. "Make up your mind. You can either take your proper place as my subservient, or take a hike!" She pointed to the door.
"Ok, I'll do it!!" I yelled. "But she has to leave. This is between you and me, Lydia."
"No, it's not, jackass. I want Anna to see this. Remember the provisions of the contract. You have no say in ANYTHING. Anna stays."
"Lydia," I said pleadingly, attempting to reach out to her.
"Don't even bother," she said. "I told you when I married you that I ever caught you cheating on me I'd nail your balls to the wall. Well, consider Anna the hammer. Plus, she happens to be a feminist who enjoys watching men get their just rewards. Isn't that right, Anna?" she asked.
"It’s true," she smiled.
This was crazy. It was like a sport to these nutty women.
"Anna stays," said Lydia. "Now sign the documents, Charlie."
Anna laid out a pair of documents. One was the divorce document that would basically cause me to give my life away, and the other was the crazy document that put Lydia (and to a lesser extent my boss – or so I thought at the time) completely in charge of my life. I ran the provisions in my mind again. I would be giving up my salary. I would have my penis locked up like it was the middle ages?!? It seemed beyond nuts. But then I felt that tiny twitch again in my pants. Before I could fully analyze the implications of my actions, I reached over and signed the crazy document that would enable me to keep my marriage.
"Ok, it's settled then," said Anna, smiling proudly.
"Take off your clothing," said Lydia.
"With Anna here?"
"I'm not going to tell you again, Charley."
Then, to both my surprise and Lydia's, Anna spoke. "You know, Charley, in my experience, this will be good for you. I've ruined many a man in my day with these prenups, but the ones who signed the other paper lived fulfilling lives serving and providing for their superior wives. Now Lydia happens to be a good friend of mine, and your name has come up over the years. Knowing what I know about you, I'm totally convinced that this is the right thing for you. You might not enjoy it at times, but you'll get used to it. Now you're not my client, but here's some free advice: Learn to embrace your submissive side and everything in your life will become infinitely easier."
I looked at Anna. Can you imagine the audacity of this little bitch? But she was making a lot of sense. I felt outnumbered. Plus I didn't have much of a choice. I began to remove my clothing. It was yet another step on the path to the complete ruination my life was to become.
When I got down to my underwear, I looked up. Both women had a look of smug satisfaction. "Underwear too," said Lydia.
I sheepishly removed my underwear and stood naked in front of them. I felt the surge of blood head toward my groin. I had no idea why it was happening, but perhaps it had something to do with getting female attention from more than one woman. Sure enough, I began to spring an erection. I stood there dumbly.
Anna: "Oh look, I think he likes it, Lydia."
Lydia: " Why did I marry such a pervert?"
"I'm sorry, Lydia, I can't help it," I said exasperated.
Anna: "Geez, Lydia, you weren’t kidding about his little pinkie. You poor girl!" She flipped out her own little finger for emphasis.
I wasn't the biggest guy in the world, but I was sure I wasn’t the smallest either. Now my wife's bitchy-ass lawyer was making fun of my penis? I felt more anger, and I couldn't help myself. "Ok honey, you got your wish. Can Anna please leave now?"
Lydia rose from the couch and approached me. To my utter shock, she reached back and slapped me hard across the face. "No, I think you should leave until you learn proper respect for my lady friends," she said. Then she grabbed my ear and dragged me toward the kitchen. She opened the sliding glass door to our deck and pushed me out into the snow. As I attempted to resist, I felt a thump in my ass. Lydia had kicked me directly in my asshole as I went out onto our snow covered deck! I heard the door slide shut and the lock click in place.
Then, Lydia flipped the light switch on and sat down with Anna at a table next to the door. Now illuminated, I feared the neighbors might be able to see me. The two women sipped wine and kept me shivering out there like an idiot in the snowstorm. Every so often they would turn to me and laugh. Finally, after five minutes, Lydia stood and opened the door. I stumbled back in, my entire body shaking.
"That's the way you can expect things to be from now on when you defy my orders, Charley," Lydia said.
I had no idea my wife could be so cruel! Actually, scratch that, I knew she had it in her, but I thought I had managed to keep it down with years of good income not to mention the inherent dominance of the male gender.
"Lydia, look at his little pinky-dick. It looks more like a peanut than a penis," said Anna.
Could you even imagine the mouth on this little bitch? But then I looked down and she as right. I was not exactly impressive at that moment.
"Oh, you're right," said Lydia. "Fortunately I haven't touched it in ages. He beats off with internet porn all the time. Check this out," she said, as she walked over to our laptop which was located in a corner of our spacious kitchen.
While I watched, she opened the internet and looked at the history. "Look at all these porn sites he visits when I'm gone."
Anna put her hand to her mouth and began laughing loudly. "Oh god - what a pervert! I swear, it never fails to amaze me what a wayward male can do without proper female guidance. Good thing you'll be putting a stop to that behavior."
"Amen," Lydia said. "Anna, I should have listened to you a lonnnnng time ago." She reached into a desk drawer and pulled out an odd looking object. I had no idea what it was.
"Charley, stand in front of me," Lydia said, more like a command than a request.
I hesitated.
"You heard your wife," Anna said. "You seem to have forgotten the paper we just made you sign. Do it NOW!"
For some reason, Anna's bossy behavior was having an odd effect on me. I could feel my loins stiffening again. This was odd because I wanted to ring her little neck. But there was something oddly exciting about being talked down to like this. I still can't explain it. I walked over and stood in front of my wife.
"Look," said Anna, "It's getting hard again. I told you men like to be treated this way." Anna took my arm and made me face her. "Charley, penises don't lie. And your penis is understanding something your feeble brain has yet to accept - you LIKE it. Admit it!"
"I don't know," I said, speaking honestly, suddenly feeling very vulnerable.
My wife's lawyer tucked her nail-polished finger underneath my chin. "Just submit to a higher power, Charley. Female power."
Lydia spoke, "Annie, your making his penis all hard."
I looked down. It was true. "I TOLD you!" said Anna again, still holding my chin. For some reason I couldn’t resist.
"Charley," said my wife from a seated position. "I'm going to place you in chastity now," she showed me the odd looking contraption. "This is a male chastity belt. It's designed to place your penis under my control. You won't be able to obtain erections any more until I unlock you. That way, I get to decide when you can orgasm and you can't masturbate or hook up with fat, ugly floozies anymore."
"I don't know," I said, suddenly very apprehensive about the whole thing.
"You don't have a choice," said Anna again. Why was she so convincing?
"Anna, I can't do this with him all excited," said Lydia.
"No problem, Lydia," said Anna. She slid open the glass door again. "Go grab a handful of snow, boy," she said.
I did as I was told. Something about Anna's self-assurance was making me comply.
"Now," she said, speaking to me as though I was a child. "Hold it up against your penis and balls like a good little boy."
I began to comply. Suddenly I felt a shock on my left butt cheek. Anna had reached back and slapped my ass! "Say 'thank you, ma'am!" Anna said.
"T-thank you, ma'am," I said, not even believing my ears.
Anna turned to Lydia, "See how easy it is."
Lydia smiled. "Anna, you rule."
"No, we both rule," said Anna. "Because we're women. Now Charley, let's see if that penis is behaving."
I pulled my hands away, doing everything this little five foot tall bitch told me to do. My penis had once again shriveled up.
"Ok Lydia," said Anna. "Time to put this penis in its rightful place."
Lydia stepped forward and placed the apparatus onto my dick. She clicked something shut and then pulled away a key, which she held in her hand.
"And so it is done," said Anna. "You've both taken a huge step in your relationship. Congratulations to both of you, but especially you Lydia."
Lydia smiled more deeply than I had seen her smile in years. "Now, I'm in control, Charley," she said.
What had I done! I looked down at the little plastic sheath around my dick. It would make erections impossible.
"Now, wait just a second," I said. "Ladies, can we talk about this?"
"No," said Anna.
"The time for talk is over," said Lydia. "My decision has been made and you signed the paper. This is just the start, Charley. You'll learn to follow my orders, and if you do, I'll let you out from time to time."
Just hearing her talk like that got me excited again. Then the pain in my groin hit me. I winced and grabbed for my dick.
Both women noticed and laughed. I felt my face redden.
"Give me that key," I said.
Lydia slapped my face again. "Shut up!" she said. "Your life as you knew it before is over. I've already instructed your office to begin depositing your pay check in my bank account. There's one more thing we need to take care of. Follow me," she ordered.
I followed the two women upstairs, both of them fully clothed in classy attire and me naked other than this awful contraption on my penis. Lydia sat down on our bed and smoothed out her skirt.
"Lie across my lap face down, Charley," she said.
I thought I knew what she was up to and it was time to draw the line. "Aww, honey, c'mon, you can't spank me."
"Correction, I can and I will. Now, lie across my lap like an obedient little husband. C'mon, I'm waiting."
I hesitated, so Anna spoke. "Charley, do I need to remind you what you signed. Your wife is telling you to do something."
I proceeded to have a temper tantrum. I stomped my feet and could feel the tears filling my eyes. "This is crazy!" I shouted and made for the door.
Anna stepped in front of me and grabbed my arm firmly. I resisted a bit, but her grasp was sure-handed and firm. "Charley," she said in a soothing voice as she faced me with complete confidence. "You know this is the right thing. Plus," she said, and then she shocked me by reaching down between my legs with her free hand. She stuck out her middle finger and lightly scratched the underside of my balls with her long manicured fingernail. I shivered. "I think deep down inside you like it," she said in a gentle, cooing feminine voice as she smiled at me.
There was something about her that I couldn't say no to. She was right! Not that I was about to admit it. I moved with her in stunned silence as she took my hand and escorted me over to Lydia. Together, the women carefully pushed me down across my wife's lap.
Even before the first blow was landed, I was crying with the realization of my defeat. Lydia slapped my ass very hard, but not with a lot of rhythm. Every so often, Anna would chime in: "C'mon, slap him harder. Don't hold back. Focus on one cheek. There. Now the other. Teach him respect!"
I could not believe how much smack talk Anna was laying on me. How had I allowed this to happen? Yet again, I felt that buzz in my groin as I heard this short little chubby bitch assist my wife in punishing me. Then I felt nothing but pain, both in my ass and my penis. The feeling of humiliation was overwhelming. I felt my body give in and begin to relax. I cried openly.
"Great job, Lids," said Anna. "Now you're giving him the business. That's how you lay the foundation for a female dominated marriage."
After a few minutes, Lydia mercifully stopped and asked if Anna wanted to partake.
"I'd love to, dear," said Anna, "but I need to be going. I have a dinner date with some colleagues. I'll take a rain check on that."
Lydia gave me a couple of more slaps. Then she ordered me into the corner. "Stay there," she said. I did as I was told. Man, did I feel weird. Yet I could feel that lingering excitement as my entire free will was taken away.
As the ladies walked back downstairs I could hear Anna. "We'll work on the spanking bit in the future. You can do much, much better. It's just a start."
They continued to talk downstairs for a few minutes and then I heard Anna drive away.
I heard the ominous click of my wife's feet as she approached the bedroom. Her skirts rustled as she approached me and again I felt the searing pain in my groin.
"Turn around," she said.
I turned and she slapped my face several times. I tried to defend myself, so she grabbed my ear and dragged me in front of the mirror.
"Get a good look at that, dearest," said Lydia. "And get used to being my naked and obedient hubby. This is your new life. In fact, I want you to repeat after me: 'This is my new life.'"
I said it.
"Louder!"
I said it again.
"Good. Now, you should know that your training will extend to the workplace. Since you work in a small office with only women, I think it will be fitting that you receive on-the-job training, so to speak. I will be informing Carissa that she has the right to punish you as she sees fit. I'm also giving her a chastity key. Welcome to your new life dear."
I stood motionless, feeling angry again. Would she really notify my bitchy young boss? That would be the ultimate humiliation.
Then I felt my wife slap me upside my head. “From now on, you can sleep in the guest room. Take all your clothing out of my room - the MASTER bedroom - and go."
"T-thank you, ma'am," I said not believing the words as they came out of my own mouth.
"Better," she said. "You can call me, ma'am or Miss Lydia. Anything else and I'll spank your ass. Anna suggested I use a hairbrush next time."
That night, as I settled into my new room, I could hear Lydia on the phone. The sound of her conversation was muted because my door had been slammed shut by her. She had put me to bed early! Can you even imagine? I thought I could hear that she was talking to Carissa. And she was telling her everything. If only I hadn't cheated on her! If only I hadn't signed that stupid prenuptial agreement! What would happen to me at work now that my annoying 27 year old female boss now knew that my wife had taken charge of our marriage? What if Lydia mentioned that I had shown signs of actually enjoying being treated this way? I fell into a nightmarish sleep.
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Chapter Five – The Office
The next morning, I woke up feeling hung over even though I hadn't had a thing to drink the night before. Then I felt a pain I would soon become quite accustomed to – the pain of morning wood. I could feel my dick strain against the chastity belt. I thought a cool shower would make me feel better, but instead it had the opposite effect. Normally I would jerk off in the shower - not any more. I could feel the frustration coursing through my veins. I took an open palm and slammed it against the shower wall.
I looked down at the ridiculous contraption attached to my dick. It was a vicious little plastic shell with a loop at the base for my balls to pass through. The head of my imprisoned penis (a horrible prison with a ruthless female warden) poked through the end, so it was possible to urinate. The contraption wasn't overly uncomfortable except for the obvious restriction. Each time my dick tried to rise up, the belt caught it cold. I could feel my dick spasm again and again as it attempted to expand and was efficiently denied by the belt. My balls felt heavy and sore. It was rare for me to go a day without ejaculating and I hadn't yesterday.
I yanked as hard as I could on the sheath, attempting to pull it off my dick. But as I did, the ring pinched my balls and caused more intense pain. Again I thumped the wall of shower stall in agony.
Marching off to my former bedroom, I decided to try talking some sense into Lydia. I saw the light was on in the bedroom, which didn't surprise me. My wife was an early riser. I knocked on the door.
"What is it?" said the voice from within.
I opened the door and found my wife reading in bed. She glanced up at me. "You better have a good reason for entering my bedroom without being summoned."
"Honey," I started.
"Don't honey me. You’re to refer to me as either 'ma'am,' or 'Miss Lydia.'
I felt the anger surging but took a deep breath. "Ma'am," I said, not believing my own words. "Look, I mean, this is crazy. I- I promise I'll never cheat on you again. Just let me out of this stupid belt. Please."
"Someone wanted to beat off in the shower," she said in a singsong voice.
"Oh, Lydia, stop it! I'm your husband for chrissakes."
"Hubby is the more appropriate word at this stage," she said. "You just earned another day of chastity for not referring to me by my proper title. That makes eight days of no release. Want to go for more?"
"Look, L- I mean, ma'am, this is- I promise I'll change! Just give me another chance."
"I'm already giving you another chance by not divorcing you," she said. "And I know you're going to change. You have no choice, silly. Come here." She motioned for me to approach the bed.
"Get on your knees."
I did as I was told.
"Make eye contact with me when I address you," she said.
Once I had complied she said, "This is your new life, Charley. Get used to it. I own that vile little penis now and the sooner you accept that fact the easier it will be for you. Do you understand?"
"I- I-," I searched for something to say.
"Give it up, Charley. Let me repeat what I said. I own your penis now, and I own you too. Understand?"
"Honey, this is crazy!" I yelled.
"You're at two weeks with no orgasm now. Want to go for three?"
"I- I," again I couldn't believe this.
"I- I," she mimicked me. "Look Charley, I'm saving who knows how many women out there from the disappointment of your wimpy little penis. You always sucked in bed anyhow."
I was speechless.
She continued: "Truth hurts, doesn't it?" When I had no reply she said, "DOESN'T IT, Charley? This is the part where you answer your superior."
"Y- Yes, ma'am," I said. Suddenly I felt that odd feeling of excitement. Then my penis began throbbing and the pain hit me again. With it came the anger and frustration.
Lydia pointed to the door. "Now get out of my room, unless you want another week of chastity tacked on."
I reluctantly headed to the door. "Oh, and Charley, your list of chores is on the kitchen table. I expect them to be completed without fail or I'll add more time. One more thing." I turned. "Say hi to Carissa for me," she smiled.
"Yes, ma'am," I said, once again infuriated.
"Good, now run along," she said with a flip of her hand.
Downstairs, I found the list. She wanted me to go to the grocery store, pick up her dry cleaning and start the laundry when I got home. Argh!
Arriving at the office a half hour later, I found a pink post-it note stuck to my computer monitor. It had girly writing on it. The words read, "See me immediately. –Carissa." The stupid bitch dotted her I's with big circles as though she was still a teenager.
I walked to her office like a condemned man. How much had Lydia shared with her? What would this little blonde bitch do? I knocked on the door.
Carissa was seated behind her desk. She looked fantastic today. She wore her crème-colored pants suit that I loved so much. She was writing something on a note pad when I entered and paid me no attention at all. I began to think maybe Lydia had issued an idle threat and Carissa didn't know about my predicament at home, or perhaps she'd just avoid going there.
Carissa looked up and gave me a smile I hadn't ever seen for her. It was a vindictive smile. I could almost see the crease between her eyes. "And how are we today, Charley?" she asked.
"Ok," I said, not wanting to give anything away.
"Just ok?" she asked. "Come around to this side of the desk for a moment," she said, pointing to where she wanted me to stand.
I walked around to the other side. I looked down at Carissa, who folded her legs neatly in the chair that was much too big for her narrow frame. She dangled a red high heel from one foot.
"Feeling a bit frustrated, are we?" She teased. I could feel the pain again in my groin.
"What do you mean?"
"Oh, let's cut the charade right now. I know everything there is to know. Take your pants off," she said, to my utter shock.
"Excuse me."
"You heard me. Take your pants off NOW."
I reluctantly began to comply.
"What do you say?" she asked.
"Yes ma'am."
"No, call your wife ma'am. I prefer 'boss.'"
"Yes boss."
"Good boy. Now hurry up! Don't keep me waiting." I removed my pants and stood in front of her.
"Are you kidding me? Your wife has a lot of work to do to train you properly. Underpants OFF! Don't think you're keeping any secrets from me. When I order you to take off your pants, from now on that means pants and underpants."
I reluctantly pulled down my underpants.
She began laughing hysterically while I stood there like an idiot. "Now that's what I call poetic justice," she said. "A philandering male put in his place by his superior wife. I love it! This is going to make bossing you around so much more fun, knowing you're being denied like this."
I didn't know what to say to that. I felt enraged, but again that creeping feeling of erotic excitement from my groin. I guess there was something about having a female boss who was younger and more capable than me. Then again, maybe it was those tight pants hugging around her unbridled little pussy, just mocking me from the chair.
Suddenly Carissa interrupted my thoughts. "You really had no idea what you were up against, did you? You thought I was some ditzy blonde who you would be able to push around. It's ok. C'mon, be honest with me, Chuck, you thought I'd be a pushover."
"I thought I had more experience than you. I mean, I do."
"True," she said. "You have more experience. You are also talentless and undisciplined. At least you used to be. But we're going to fix that. I had a long conversation with your wife last night. We talked about your training and we agreed it would take a coordinated effort between your wife...and your boss."
"Yes, boss."
"Good boy. I wish I had a mirror in here. You should see yourself standing in front of me like the de-pansed idiot that you are. Okay, here's the way this is going to work. First I removed your pants. Now I'm going to remove your dignity."
She reached into her desk and pulled out a large wooden paddle. It looked like something out of a fraternity. "This is something I've wanted to do for a long time.” She unfolded her legs and positioned her ass in her chair, squeezing her thighs together.
She tapped the large paddle against her palm. She pointed to her lap. "Get your ass over my knee."
I hesitated again. I knew the predicament I was in but there was something about that paddle that put the fear of god into me.
Carissa spoke again, with her annoying bitchy little voice. "Listen, Chuck you have two choices. You can either get your ass out of my office, pack your stuff and leave, where I'm sure your wife will kick you from the house and ruin your financially. OR, you can get your ass over my lap for a good old-fashioned punishment.”
I ran things over in my head. Talk about being in between a rock and a hard place. I did NOT want this little bitch to spank me like I was a child. It would represent my ultimate defeat, as far as I was concerned, at the hands of a skirt no less - a chick, a tart, a dumb blonde. But then I thought of what my life would become when Anna was done with me. I'd be ruined. Then I thought of Carissa. There was something about taking orders from her that I found exciting. Despite what it might mean for my career and my future, I felt myself giving in. With that, I positioned myself over Carissa's lap.
"I knew you'd see it my way," she said. She pinched my sheathed penis between her knees, trapping it firmly. Then she straightened her narrow upper body, which caused my trapped penis to stretch as she pulled her knees down slightly. From my vantage point, I could see her feet pulled neatly together. I had to admit I had a fetish for leather boots. And to think those feet belonged to a woman who was just entering middle school when I received my high school diploma.
"Give me your hand," she said. "No, your other one, stupid. There, that's it." She twisted it behind my back. I groaned from the sharp pain in my shoulder.
"You know," she said, as she rested the paddle across my buns. "This isn't the first time I've had a fully grown man over my lap. I had a wonderful female professor and role model in college who taught me all about the benefits of male spanking. It's the physical and emotional domination of the male in its purest state. There's something so perfect about taking a wayward male over one's lap and smacking his naked bottom. I've found the psychological impact to be totally overwhelming to most men. There's no better form of humiliation on the planet," she said as she stared off into the far corner of the room with a serious look of concentration and contemplation on her face.
With that, she raised her hand and shattered my world as I knew it.
The next ten minutes were the most cathartic ten minutes of my life. At first the blows were startling and incredibly painful. It was a totally different experience compared to the hand-spanking Lydia had given me the night before. I tried to move, but she was much stronger than I expected her to be. She had my arm trapped painfully and her knees were like a bear trap around my sheathed penis. Any wiggling of my ass caused my dick to stretch in ways it was unused to stretching. I began to groan and kick my legs. At some point I started begging her to stop. But the blows kept coming. The paddle was so big, it covered both of my ass cheeks. Every so often she would hesitate from her usual rhythm and I'd be left flinching and flopping in her lap like a fish out of water. I clenched my ass cheeks as I tried unsuccessfully to anticipate the next blow.
"Two for flinching," she said, and gave me two quick whomps before stopping again. Those brought me close to the edge. I kept my ass cheeks clenched, I'm sure to her great amusement, and began begging her to stop. "Please C- Miss Carissa, boss, I- I give up. You win."
She didn't respond. Instead she once again began a rapid, merciless paddling of the center of my now scalding ass. After ten of these, she said, "This is where I put your ass into the frying pan."
Soon after this ominous comment, she increased the pace of her paddling. It was an onslaught and her hardest blows. My legs now convulsed in a futile attempt to carry my body to safety. But it was useless. They took me nowhere. She would later tell me this happens to all men shortly before they break down. It's an instinctual effort to escape the pain. Now I could feel myself giving in. My legs stopped kicking and suddenly I just let it all out. I hadn't cried since I was 14 years old. My sobs were of the deep, heaving variety. I slumped into her lap, head down, just bawling my eyes out. Inside, despite the intense pain, I felt an odd sense of safety as a higher being took charge of me.
Once she felt me go limp, Carissa held the paddle against my burning ass and said, "That's it, Chuck, let it all out. I know it must hurt so much. I don't think you'll go cheating on your wife any time soon, will you?"
"No ma'am," I wailed.
"It's 'boss.' she said. "Do I have to blister your ass for you some more?"
"No boss!" I hurried to correct myself.
"Better," she said. "Now get off my lap and get under my desk where you belong." I felt her sink her fingers into my ribs and shove me onto the floor. I slipped off her lap and flopped two feet onto my stomach, a piece of wreckage in front of my boss, who casually smoothed out the wrinkles in her tight pants.
She stood and held the paddle up menacingly with one hand. She pointed with the other to a spot on the floor beneath her desk. "Crawl under my desk! What are you waiting for?"
I saw her beautiful cunt jutting proudly forward in her pants. It was almost as though she was taunting me with it. Then I felt that tingling submissive feeling again. I scurried under her desk.
"On your stomach and face me," she ordered.
"Yes boss," I said.
Her boots were now directly in front of me.
"My boots need polishing. Use your tongue."
"Yes boss."
She proceeded to make a sales call while I lay there licking at her boots. At one point she paused and said, "Make them nice and shiny." Then she went back to her phone call as though I wasn't there.
Then to my horror, I heard her buzz someone in the office. Marsha answered, "Yes Carissa, what's up."
"Come on in here. There's something you have GOT to see."
"I'll be right there," said Marsha. I could hear the excitement in her voice.
Once I hear Marsha hang up, I again heard Carissa's voice. "Get up," she said.
I stood up.
"Are you forgetting something?"
"What is it?" I asked, confused, probably due to the pounding I had just taken.
"Yes, boss," she said, reaching around me and slapping my ass with her open hand. "Now stand with your back facing the door. Like this," she said, standing and positioning me so I stood next to her chair and faced the window.
I heard the door open and click and then the laughter of the company founder. "Oh my god. Look at that ass. It's so RED!" she exclaimed.
" I don't mess around," laughed Carissa. "Why do you think you hired me?"
"Good point. Well I can see somebody is getting a serious comeuppance. How's it feel to be put in your place like this?" she asked me.
I had no idea what to say. Suddenly I felt a hard crack on my swollen ass. Carissa slapped each cheek hard. Because it was so sensitive, the slap instantly produced fresh tears.
"Owww! It- it hurts," I said, and I'm ashamed to say I was crying again.
Again, Carissa spanked each cheek her with hand, causing me to begin my deep sobs again. "Address her as your superior, you idiot," said Carissa. "Yes Miss Marsha."
"Yes Miss Marsha."
"I'm so sorry, Marsha," said Carissa. "Give me some time and I'll have him jumping through hoops for you."
"I have no doubts about that," beamed Marsha. "No doubt whatsoever." Then, she addressed me, "Charley."
"Turn around, Chuck - a woman is addressing you," ordered Carissa.
"Yes boss," I said, out of fear of getting my ass slapped again.
Marsha spoke: "I've been waiting a long time to see someone put you in your place like this. And I'm absolutely thrilled it's a talented young woman. You are to fawn over Carissa. Whatever she needs you to do. And I mean WHATEVER she needs to do. She has my complete blessing to do whatever it takes to humiliate you and teach you respect for women. It’s either that, or a one way ticket out of here. Have I made myself clear?"
"Yes, Miss Marsha," I said, still sobbing.
"Wonderful," said Marsha. "This has been a long time coming. I can't tell how thrilling it is for me as a woman watching a young lady like Carissa come in and reform your behavior over the past two months. And the funny thing is, I think you’ve wanted this on a subconscious level."
"Of course he wants it," added Carissa. “You wouldn’t believe how many times I’ve caught him staring at my body.” She faced me. "Now, Chuck, I spoke with Lydia last night and I promised we'd give her an update on your behavior. So, just stand at attention while we give her a call."
I began to feel angry again. To be treated like a child was upsetting to me.
Carissa sat back down in her chair and dialed off those numbers rapid fire. "Hello," I heard my wife on the other line.
I waited for Carissa to say something. Instead, she turned to me. "It's your wife, Chuck. I think you have something to tell her."
"Uh, yes boss," I said. "Hi Lyd- I mean, ma'am."
"Hello Charley," she said. It sounded like she was suppressing a smile. I didn't know what to say.
"Tell her how your female boss just spanked you to tears," said Carissa proudly, as Marsha smiled at the scene in front of her.
"Ma'am," I said, not even believing what my life had come to. "I- I was a bad boy, and C- I mean my boss-"
"Your FEMALE boss," said Carissa. "Tell her how I took you over my lap and spanked you until you were sobbing!"
"My female boss spanked me to tears." Something about the admission of this fact caused me to break down crying and sobbing again.
Lydia's laughter echoed through the speaker phone and filled the room. "Just wonderful," she said. "Carissa, thank you VERY much for addressing behavior. I'm quite certain he's going to learn his lesson about who is in charge of his life now."
"Oh, it was my pleasure, believe me," said Carissa proudly as she leaned back in her chair and crossed her legs.
"Charley, I hope you know now how serious I am about this new arrangement," said Lydia.
"Yes ma'am."
"You've had this coming to you for a long time. Carissa and I will be speaking regularly on the phone and keeping close tabs on your behavior. Both of us will take great joy in doing whatever is necessary to teach you proper respect and contrition. Are we clear?"
"Yes ma'am," I said, the tears rolling down my face.
"Good boy."
Carissa chimed in: "Isn't it amazing what a little properly applied feminine discipline can do to the male ego?"
Marsha burst into laughter, as did Lydia on the phone.
"You've got that right," said Marsha. I had to see it for myself to believe it.
"You know, my girlfriend Anna the lawyer told me how easy it would be," said Lydia. "I didn't believe her, but now I do. I think Charley might not be so willing to admit it but he likes to be humiliated by women. Don't you Charley?"
"I- I don’t know, ma'am," I said.
Lydia continued. "Last night, Anna just diddled with his genitals a bit and he melted into our hands."
"Is that true, Charley?" said Carissa. "All this time you've been resisting me, you secretly were glad that I was your new boss?"
I wanted the promotion and the truth was I was very unhappy when she got my job. But I figured it would be better to fall into line. "Yes boss."
"Ha! I’m not sure I believe you, but it doesn’t matter. I’m in charge now, and frankly I don’t give a shit if you get off on it or not," said Carissa.
With that they said their goodbyes. "See you at home, Charley," Lydia said. "Don’t forget your chores."
"Yes ma'am."
Carissa turned to me. "Charley, put your clothing back on and go work on those leads I emailed you. Marsha and I need to have a talk."
"Yes boss."
I stepped out into the hall and there was my secretary, Joan and Carissa's secretary Gina. Both must have heard what was going on because they both had wide grins. I should mention we had a very small office with me, Marsha, Carissa, Gina and Joan. The rest of the sales force and management team were located in the suburbs. I only hoped Gina and Joan wouldn't get to witness my shame first hand.
The rest of the afternoon was quite painful. My ass was so sore I couldn't sit properly at my desk. Carissa came in at some point and saw me standing and typing. She flashed a triumphant smile. "I got you good, didn’t I?" she said. My door was partially open and I feared that Joan could hear her in the hallway. .
“Yes boss,” I said.
“Well, don’t you worry. You can expect more of that treatment should there be additional misbehavior, though I might be delegating your spankings to the other ladies from now on.”
What did that mean? Did she mean Martha? Or, heavens help me, one of the secretaries? I tried to put that out of my head and do everything I could to make my new boss happy.
James Pendergrass femdom – www.lulu.com/jmplays. Thanks for reading.
Chapter Six - Crackdown
The next few weeks were just plain brutal. Lydia furthered my submission to her at home. She had me naked at all times, other than my chastity belt, and doing one chore after another. One night, just a few days after I had been put in chastity, I overheard her laughing in the bedroom and I put my ear to the door. She was talking with Anna and speaking of me in the most demeaning manner. "Yes, Anna, it's quite wonderful. He's fallen right into line. The chastity is such an effective tool. Oh, and check this out. Carissa took him to the woodshed the other day. Ha ha! I can't believe how much fun I'm having." I could feel my face redden as I listened to my wife have a good laugh at my expense.
Thanks to my big mouth, I managed to build up my time without a release to five weeks! I was devastated. I soon realized that if I ever hoped to cum again, I needed to make Lydia happy. This meant doing whatever she told me to do, which included every household chore and errand imaginable. She constantly peppered me with verbal abuse, which I learned to endure without complaint. The tiniest infractions on my part were met with harsh punishment. One night she told me to get on my hands and knees and scrub the floors in the kitchen. When she caught me rolling my eyes, she added a week of chastity. It was crushing to me. Not to mention she docked my weekly allowance which meant I couldn't drink beers with the fellas on Thursday night. My best pal Stanley asked me what the hell was going on, but I was too ashamed to share it with him. I complained to Lydia about not being able to afford guys night out and she said it was my own fault and promptly added another day of chastity.
When she wasn’t disciplining me or ordering me to do her chores, Lydia ignored me. She said I wasn't ever to approach her room without being summoned. I also wasn't to speak with her unless it was urgent, such as a clarification on a chore she wanted me to do.
As bad as my home life had become, it was nothing compared to the humiliations that were visited upon me at work. Carissa went on a three day business trip the day after she first blistered my ass, so I had a short reprieve. When I arrived at work the day of her return, I noticed she had sent me a meeting request titled "New World Order." I had just lost a key account earlier that day, so it was with a great deal of trepidation that I entered my boss’ office at four o'clock on the button.
Carissa didn't waste any time. "Pants off. In fact, just take it all off, and kneel before me.”
After acknowledging her with a brief "Yes, boss," I did as I was told.
"I spoke to your wife earlier today. She says she had to add weeks of chastity and cut your allowance."
"Yes boss."
"And now I find out you've gone and blown the Wilson account. What do you have to say about that?"
"Well boss, I've been working on them for the past seven we-"
"You know what. I don't even want to hear it. I told you when they hired me I wasn't hear to make friends and I'm results oriented. It's clear I haven't yet humiliated you enough for your own good."
With that, she turned to her phone and hit the speaker button. To my great horror, she dialed my secretary.
"Gina, can you come to my office when you have a chance?"
"Why certainly, Carissa," said Gina with a more pleasant tone than she ever reserved for me."
"Wonderful," said Carissa happily. "Oh and bring Joan along."
"No problem, hon."
Oh no! Now the two secretaries, both of whom I knew didn't particularly like me to begin with, were going to see me in my exposed state! My face began to redden.
Carissa must have noticed. "That's right. It's time for the ladies to see the REAL Charley, the one your wife and I know all about!"
Moments later, the door opened and our two secretaries walked in the door. Gina was a tall Italian woman with shoulder-length dark hair. She was big-boned - kind of an Amazon woman when you get right down to it. She looked like her usual severe self, with a gray skirt suit, though she did wear spiky high heels, which made her look six feet tall. For years, Gina was my secretary. I had wanted to hire a hot little piece of ass but Marsha wouldn't let me do it. Once I had even fired Gina, but it had been overturned by Marsha, who made Gina her own secretary. After that, Gina and I were never on the best of terms.
My new secretary, Joan, who I had no say in hiring, was practically a brown-haired version of Gina in terms of her personality. She was a bit shorter than Gina and had a fat ass. I knew she couldn't stand me, though it was clear she got along famously with Carissa. To her credit, Joan didn't let her fat ass stop her from wearing nice office attire. Today she wore a light green suit that hugged her bulky butt and showed off her giant vaginal cleft. She wore a lot of makeup and expensive jewelry - a big pearl necklace and diamond earrings. She was a divorcee and had taken all of her husband's hard-earned money. I knew for a fact she was a man-hater, as was Gina.
Based on their reactions to seeing me on the floor and naked, I'm fairly certain they had been made aware of my predicament in conversations I wasn't privy to.
"Well, what do we have here?" said a delighted Joan.
"Charlie,” said Gina. "You seem to have forgotten your clothing today."
"Look at his penis! It's locked up!" said Joan.
"Is there even a penis down there? I can hardly tell," said my bitchy ass ex-secretary Gina. I was tempted to grab her by the neck but instead I merely hung my head in shame.
"Ok, confession time," said an equally delighted Carissa. Why don't you explain to these lovely ladies why you're naked and on your knees."
I had to go through every detail, my cheating, my signing of the contract and subsequent chastity and enslavement, the weekly allowance, and of course, the bare bottom spanking. I stuttered like a fool and every so often my sure-handed boss chided me as I forgot crucial details. At the time, it was the most humiliating moment in my life, being laughed at by a couple of annoying bitch secretaries. Of course, since then I've been humiliated far worse.
Once I was done, Carissa brought out the terrible paddle. I went over her lap and she made me count off ten hard spanks. After each one I was ordered to say "One, thank you for spanking my ass, boss...Two, thank you for spanking my ass, boss."
After seven, my voice was catching and by the time she hit me the 10th time, I was crying softly. Then to my surprise, she lay the paddle across my buns.
"I'm sure I'll be spanking you often, but I want to give other women the opportunity. Get your red ass over Gina's lap, NOW!"
Gina laid into me with absolutely no mercy. I mentioned she was a big-boned woman and she did not hold back. I was sobbing and screaming. As I moaned in pain, you'd think Gina might show a tiny bit of sympathy. But no, her first comment was, "This feels really, really good!" Then she started asking me, "Who's my bitch?"
"I am!" was my fearful response as she asked me again and again. Meanwhile the tears streamed down my cheeks. "Don't forget it!" she warned.
Then I was passed over to Joan. Joan pinned me over her thick lap and began spanking away. Since I was already sobbing when she first began, my loud cries filled the room throughout the severe blistering she gave me. And I do mean blistering – an inspection of my ass that evening showed a pair of serious welts – one on each cheek. It didn't seem to matter to them since they were laughing and joking the whole time.
When it was over, I had to crawl in front of each woman and thank them for the lesson in discipline.
"I'm thrilled to put you in your place," said Gina. “I hope I get the opportunity to do it more often."
"You certainly will," said Carissa, much to my chagrin.
"Nothing like crushing an out-of-control male ego," joked Joan.
Carissa then made me stand in front of her. She took my chin in her hands. "Both of these ladies have my authorization to spank you any time they see fit to do so. They are women, which makes them your superiors. Are we clear?"
"Yes boss," I said, continuing to cry and sob openly.
"In fact, I think it's only fitting that you don't wear pants while you're in this office. After all, it's just you and a bunch of female superiors. We need access to your misbehaving ass at all times."
Now I had to be naked from the waist down? This was too much, but I wasn't about to challenge her authority.
“You’ll get used to it,” said my fair-haired boss.
If I thought the initial humiliation was bad, imagine my surprise when a week later Carissa called me into her office around lunch time. We had a female client that I had rushed off the phone earlier that day. Thanks to Carissa's ridiculous quotas, I couldn't allow her to babble on about my lack of service while I had other calls to make. The woman promptly picked up the phone and called Carissa to complain about me.
On this day, Carissa had dressed far more formally than she had when I first met her. She wore a dark skirt suit that hung appropriately just below her knees, fancy stockings that had a line going up the back. Her suit jacket was buttoned on top of a white blouse. She wore open toed heels, and I had to admit they looked utterly spectacular. I could feel my penis begin to twitch and tried to avert my eyes.
"You seem to be a slow learner,” said Carissa.
"Boss, I had to make other calls. There's only so much time in the day."
"What? Are you mouthing off to me?"
"No boss."
She reached out and slapped my face. "It's amazing, despite all the spankings your ego still isn't in check. I see we need to take things up a notch. Take ALL your clothing off. You need to be completely naked for what I'm about to do."
Since her edict from a week ago, I had been walking around the office in a shirt and tie on top with nothing underneath. Now she wanted me in my birthday suit.
Once I was naked she appraised me carefully. "Is your poor little penis straining against the cage? Let me see,” she said, savoring the moment.
“Well, it just could be your lucky day. I need to take off your chastity belt." She removed her keys from her purse. "Stick your pathetic groin out. Don't make me have to reach for that dirty penis."
Suddenly quite excited, I thrust my pelvis out toward the young woman. Was she going to allow me to cum? I could feel the blood rushing to my dick.
It was as though she could read my mind. "Forget it, dork. Do you really think I'm going to let you cum today? That's your wife's call. I'm just freeing up your penis so I can give it and your balls a severe crackdown."
My heart sank. "That's right," she continued. " By the time I'm done, you'll be begging me to lock it back up."
She unlocked my belt and stood up from her chair. "Spread your legs," she said.
She put her hands on my shoulders. I could smell her scent and my suddenly free penis instantly sprang to life. She looked down at me and began laughing. "That's why Lydia had no choice but to control your penis.”
I looked at her. She was the picture of femininity.. Her scent was overpowering. She just smelled like sweet pussy. There was no other way to describe it. For the first time, it occurred to me that I was dealing with a woman here. Carissa had a woman’s body and a woman’s confidence. It was her youthful face that had caused me to underestimate her. Now I realized how devoted I was to her. There was something just so right about being taken control of, outsmarted, and dominated, by such a sexy young woman. My cock began throbbing as I began to get over-excited by my state.
“Look at you!” she laughed openly. “You love it. Tell me how badly you want me to bust your nuts for you.”
“Please, boss,” I practically slobbered. “Bust my nuts.”
She took my face between her hands and gave me an intent stare. ”Ok, since you obviously need to be humiliated so badly. I think it’s high time I kick a little sense into you."
I knew what she was about to do to me but I was powerless to stop it. She stepped forward and drove her knee up into my exposed groin. The last thing I recall prior to the devastating pain was the look of sheer determination in her face as she caught my dangling testicles with her hard little knee. I can only guess she caught them perfectly because I felt a wicked impact drive me up almost off my feet as my balls compressed sickeningly from the power of her pointy knee. I hadn't come in five weeks and my balls were absolutely full. How they didn't rupture I'll never know. I crumbled to the floor in total agony.
Before I could even recover my breath I heard her standing over me. "Thank me for busting your balls,” she said.
“Thank you, miss, er, boss.”
“That was just the beginning," she said. "On your knees."
She sat back down on her big chair - the chair that should have been mine. "Crawl over in front of me," she ordered. "Don't make me have to lunge to do what needs to be done."
I crawled over to her. She looked so beautiful and - I hate to say it - in command as she sat back in her chair. I focused on the outlines of her shapely pussy through her tight little skirt. Now that my dick was free, despite the pain, I suddenly wanted her so badly. But I knew better than to say anything. It didn't matter - my dick was doing all the talking.
"Look at that little dick," she laughed. "Give it an inch and it takes three!"
"I'm not going to lie to you," she said. "I really enjoy busting balls, even more than I enjoy spanking. Except, I'm not just going to bruise your balls. I'm going to kick your penis for you, until it goes limp. Now, spread 'em."
With that, she began kicking me in the balls again and again. Every so often, she would kick me right in the underside of my dick, which caused it to waggle up and down. The sound of her kicks was sickening. She kicked hard, but she seemed to know exactly what my limits were. Every few kicks I had no choice but to crumble to the ground and cover up. Her response? "GET UP!"
After five minutes, she was really getting into it. I noticed she had begun groaning with apparent pleasure as she delivered each kick. I was also groaning, but my groans were not happy ones. I fell to my knees. In the past two minutes, my balls had grown pretty swollen and I was unable to stand more than one or two kicks at a time. Carissa pinched my ear painfully. I looked up and saw her beautiful pussy only a few inches from me. I swear I could smell it. She ranged back and began kicking my swollen sack rapid fire with her right foot. I watched in awe as her hips flexed - I swear I could see her vagina flex as she delivered 10 to 15 hard kicks in a span of maybe five seconds. I looked down as my balls and dick were battered repeatedly. Each time her foot crashed into my groin, my balls and dick went flopping around from the impact. I tried to fall so I could avoid the assault, but she held me in place by my ear as she racked me again and again. I heard her groans of ecstasy. It sounded as though she was having an orgasm. Finally, after one particularly devastating kick, she released my ear and I splattered all over the carpet, a total piece of wreckage. I looked down and my limp penis was almost engulfed by my swollen sack. Thanks to her violation, my “package” was considerably redder than the surrounding skin.
But she wasn't finished.
"Inspection time," she said. "Time for up-close examination of that penis and those balls. I want you face up across my lap, NOW. C’mon, you should love this part."
Normally I would, but my groin was so sore. Nonetheless, I felt myself began to tingle in anticipation of the attention I might get from her.
She sat down with feminine grace in her chair and pointed to her knees in an unspoken command. I submitted myself face up across her lap, totally exposed. I looked down at my package. It was bad. My balls were swollen beyond belief. Thanks to Miss Carissa, my scrotum had become a big angry looking crimson and purple ball. You could no longer see each nut since the entire package had been so racked by my female boss. Carissa noticed and commented on it.
"I promised you I’d bust your balls for you," she giggled. Then she casually reached down and slapped my balls three times in succession. They were light slaps, but enough to cause me significant pain. I convulsed like a rag doll in her lap. “Oh, relax,” she said. “I’m not finished yet.” She gave me a fourth slap, this one a bit harder.
I convulsed instinctually, but before I could wriggle out of her lap, she grabbed a flap of nut skin and pinched it between her thumb and index finger. I was going nowhere. I groaned in pain. She threw her head back and laughed. "This isn't going well for you, is it?"
"No, boss," I grunted.
"Those balls look appropriately disciplined. But it looks like your penis needs additional lessons." She took her other hand and grabbed my dick in her slender fingers. A feeling of pleasure overcame me. It had been a long time since I had felt the pleasure of a female's touch on the most sensitive part of my body. My chest began tingling and my cock instantly expanded in her hand.
“Look at you. Reduced to a throbbing pervert!” She squeezed my cock, rather gently, then slackened her grip, then squeezed again. I could feel the waves come over me as she continued. "So easy to manipulate,” she said, stroking me gently as I relaxed temporarily in her lap. “It's only going to get worse for you, you know. I would have fired you a long time ago, but I needed a male clown to be able to take my frustrations out on. Marsha and I talked about this. She wanted to keep me happy and I said, 'let me have a nice male ass-clown to tinker with.' She was skeptical but ultimately I convinced her it would be good for the company."
She pivoted the chair toward her desk while continuing to hold me by my throbbing penis. She released my poor balls with the other hand and grabbed a ruler from her desk.
"Time for a good hard penis spanking," she said. I looked at her face and could see it was slightly flushed. It occurred to me she was getting off on this.
"This is going to hurt, but I don’t care."
With that, she bent my hard penis down between my legs, and exposed my purple head. Then she began rapping the sensitive head with the ruler. I was afraid it would burst! It was incredibly painful but she gripped me tight. I grunted and squealed with pain as the ruler stung my penis head again and again.
"I'm not going to stop with your penis punishment until you go flaccid," she said.
And she didn't. It took a long time because I was so turned on by the feeling of her thumb and forefinger as they combined to force the lower portion of my shaft downward and away from my penis’ natural inclination to throb against my belly. Again the symphony of noises - the rapping on my penis head, the female grunts of joy and the male groans of agony filled her office. I threw my head back in tortured angst. My mind went almost blank as it focused entirely on the stings on my once proud organ. I was completely dominated and I knew it. I don’t know how long she kept me there, but at some point she stopped cracking down on me. I looked down and was horrified to see my cock red and sore, but also limp.
"Get off my lap!" she said, shoving me onto the floor. Her order wasn’t necessary, since the shove she gave me was more than enough to knock me off her lap. I crumpled up into a ball as I felt my penis continue to burn from her punishment.
"Now we're getting somewhere," she said. "But there’s one more crucial step. You still need a proper ass kicking, and I'm just the girl to give it to you. Get on all fours and face the door."
I wearily crawled into position. She stood in front of me and stuck her foot under my chin until I was looking up at her. "Ok, I've punished your cock and balls, but don’t think I’ve forgotten about your asshole. And that tender spot between your balls and ass? Don't think I'm going to ignore that either."
With that, she walked behind me. "Spread your legs!" she ordered. "Hands on the floor, ass high in the air! "C'mon, I want you up on your tippie toes. Higher! That's it." I felt a hard thud as her foot slammed into the area between my balls and asshole. It wasn't a sharp pain like the ones I had been experiencing thus far, but it still hurt. Then she did it again. And again. And again. For the next five minutes, she quite literally kicked my ass. There is no other way to describe what took place. Every so often her kick went too low and caught my balls. This caused me to bounce up into the air and collapse in a heap. She just ordered me back into position. It was vicious. "Nothing like kicking some dumb male ass!" she said gleefully. "Uhh! Take that, lackey. UHH! And that! UHH!" Finally, with one vicious kick, she nailed my already devastated balls from behind. I heard the sickening clapping sound as my balls were flattened against my body by her foot, and I fell onto my stomach. I saw stars. I think I lost consciousness for a moment.
I looked up and Carissa was walking over to the door. She opened it wide. Oh no! The secretaries were out there. And I could see they had company that had joined them for lunch. Gina's friend Sue was there. She was the receptionist at a place down the hallway. I think she was around 40, and a good looking petite married bitch. And Amy was there! Oh no! Joan's sister in law who she often dined with us was a knockout little red head who I had hit on unsuccessfully in the past. I could see them all there chatting.
"Girls, there's something I think you need to see," said Carissa. "I was just in the process of kicking this ass clown out of my office."
She walked back behind me. "I'm going to kick you out now. Crawl forward a foot or so with each kick. But keep those legs SPREAD."
This was going to be horrible. I was finished.
Thump! Thump! Thump! Thump! Thump! Carissa literally kicked my ass out the door. As I reached the edge of her office, I now saw all four women standing outside pointing and laughing at the spectacle moving toward them.
"Now, get that ass high in the air. Up on those tippie toes!" ordered Carissa.
With that, I felt one final thump from behind, only this one crashed into my dangling package. The pain was so intense that I reacted as though I'd been hit with a cattle prod. Again, I saw stars. I tumbled onto the floor, defeated worse than I'd ever been defeated before. And what did I hear? Female laughter and lots of it.
I looked up and there was Carissa standing triumphantly above me with a big smile, hands on her hips. "Apologize to these ladies for interrupting their lunch!" she ordered.
I was made to crawl to each of them and apologize profusely for making such an ugly spectacle of myself.
"Ladies," said Carissa. "I am so sorry he pulled this crap. I think he needs one final punishment. Do you have any suggestions?"
It was Gina, not surprisingly, who spoke. "Well Carissa, I think we'd all feel better about things if you gave him a good hard bare-assed spanking for being such a bad boy!"
The other ladies laughed.
"Yeah, I would LOVE to see that," said Amy.
With that, Carissa brought out the big paddle and ordered me back over her lap, this time face down. She pinned my arm behind my back, not that she really needed to. I was already completely under her control by now. You won't be surprised to hear that she did not hold back. My ass soon turned an even darker color than my cock and balls. I kicked my legs for a while before breaking down in tears of great shame.
Once she was satisfied, I had to again go and apologize to each woman for making such a complete ass of myself. They laughed and made vicious jokes at my expense. Gina couldn't resist grabbing my ear and giving me a few hard open-palmed slaps on my burning ass. My futile efforts to evade her hand caused Amy to exclaim, "Look at the way his penis is bouncing around!"
"Would you like to give him a few good slaps, Amy?" asked Gina, holding me by the ear.
"Sure!" Amy said. She walked behind me and slapped me five or six times causing me to break down again in a fresh round of sobs. I think the other women were a bit surprised at the young lady’s brazen confidence. "Wow," laughed Amy. "This is, like, perfect frustration relief."
"I'll call you the next time he's bad and you can take him over your lap," said Carissa.
"Really?"
"It'll be my pleasure," said Carissa. "Now get over here, you bad boy."
I cried on over to Carissa, who locked my limp penis back in my belt and ordered me to go sit in my office and think about what I had done to deserve such treatment.
I cried all by myself as I heard the excited female chatter on the other side of the door. Both Amy and Sue had all kinds of questions. Amy told them about how I had hit on her in the past, and that I was obviously an egotistical, chauvinist pig. She said it was hilarious to see me “punked in such humiliating fashion.” Carissa told them every single sordid detail of what she’d done to me. Her stories elicited more joyous female laughter. I just lay on my stomach and groaned as I felt a combination of stinging and throbbing pain in my cock, balls, ass and anus.
Ten minutes later, Carissa poked her head in. "Come back out here for a minute, ass clown," she ordered.
Once I was outside, Carissa asked me, "Are we going to have any more misbehavior out of you?"
"No boss," I said.
"Then get down on the floor and promise these women you'll try to be a better, more obedient ass clown.
I went to each lady, and each one had a remark for me, like "I hope so," and "You'd better or your ass will be sorry." Meanwhile Carissa picked up the phone and filled in my wife on the details of the day. She handed me the phone and my wife's happy voice was on the other line.
"Well, Charley it sounds like you've had a most busy day."
"Yes ma'am.”
"You should know based on your lousy performance at work, I've decided to add another two weeks of chastity."
Oh no! I had expected to have the opportunity to come in a mere three days!
"Yes ma'am," I said, and felt the tears loosen again.
"Your allowance will be $20 a week for the next two weeks."
"Yes ma'am," I said, now crying for like the fifth time that day.
"Oh lighten up, you fool. At least you'll have no choice but to go on a diet. Now, I have to go. I have an appointment at the spa. Work hard, OR ELSE."
"Yes ma'am."
CLICK
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Chapter Seven – It Gets Even Worse
One morning, I arrived early to work. It was a week after Carissa had first kicked "the starch" out of me. She'd done the exact same thing yesterday after I had fucked up another account. Even worse, Joan had taken a video of the racking with her digital camera. After it was over, Carissa reviewed the humiliating ballbusting with me. She focused on one kick in particular since it was a perfect kick in the nuts and featured both of our faces in the frame.
“Look at the look of composure on my face,” said Carissa. “Do you see how focused and calm I look?”
“Yes, boss.”
“Now look at you. Look at how flustered and dominated you look. See the expression of angst on your face as I drill you?”
“Yes, boss.”
“Now, look at that perfect kick. Look at your balls and penis at the point of impact. Look at the way they recoil from the blow, how they flop around so haplessly. Now, look at your reaction!” She laughed in my face as she played the moment of impact in super slow-motion backwards and forwards. “Boom! Bang! Wham!” she said after each replay.
“Yes, boss. Thank you, boss.”
“You’re welcome. That’s what it’s all about,” she said finally.
I didn't seem to be having a great deal of sales success lately, but the company was doing better than ever. I had to admit it was due to Carissa's leadership. She was selling up a storm, more than Saul ever did.
Checking my email, I saw there was a note from Carissa ordering me to come to her office as soon as I got in. When I entered her office, she was reviewing something on the computer. She motioned me over and as I got closer I got a whiff of my boss' lovely scent. She looked stunning as usual today, dressed in fall colors - a brown leather skirt and an orange blouse. She wore a garish belt with a huge buckle that highlighted her superiority. Her brown leather boots matched the skirt.
"Good morning, ass clown. Stop staring at my body and go fetch me some coffee," she ordered.
I went back into the kitchen. I heard the click of high heels and Joan marched in behind me. "Oh," she said, chuckling. "I still haven't gotten used to you marching bare-assed around the office."
"Good morning superior Miss Joan," I said. I turned and presented my ass to her as I was now instructed to do when I crossed paths with the secretaries. She gave me a half-hearted slap, but otherwise ignored me. Seconds later, Gina marched in. I presented my ass to her, but she also ignored me.
"Joanie, the video is SPECTACULAR. I swear it's just wonderful to see such lovely female dominance at the exact point of impact!"
"I thought you'd like it, thanks."
"I love them. The look on this dipshit's face is priceless," said Gina. With that, she reached out her hand and gave my balls an underhanded slap. The pain almost caused me to drop the coffee as I stumbled, but I made sure to say, "Thank you, superior Miss Gina."
I walked back to Carissa's office. She motioned me to come stand beside her and look at her computer screen. On the screen was another scene from yesterday.
"Look at this photo we made from the video, lackey. It's my favorite." If the video wasn’t enough, now I had to look at her giant 25" monitor. It was a particularly vivid femdom photograph. Carissa was wearing her all black outfit yesterday - skirt, blouse, heels, and stockings. In the photo, she's got me pinned up in front of the hall mirror. It's a rear view of her sleek body. The woman has the balance of a gymnast. Her right foot is planted firmly on the ground, while her left foot is planted firmly between my legs. Joan managed to capture the worst moment of impact. You can't see the tip of her shoe because it's embedded in my groin, but the bridge of her foot has crashed into my balls and they are compressed against her lovely foot. My penis, meanwhile is pointing straight up in the air as her foot drives me up off my feet. Only the very tips of my toes are on the ground. I remember this kick well since it put me on the floor for several minutes. You can see the look of total agony on my face and in the mirror you can see Carissa's face. Her mouth is open slightly as she exerts herself. It looks like she's groaning with satisfaction. You can also see Joanie holding the video camera. She has a big smile on her face. Gina is also there in her blue dress. She has her hands together (I think she was clapping) and a look of sheer joy as she watches intently.
"Just look at how badly I'm racking those balls," she said. "Look at your penis! Look at how exposed and humiliated you are! Look at how happy all the women are! Now that's female power right there. And to think you actually enjoy having your ego - and balls - racked." She laughed heartily.
Carissa tossed her head back until her pretty blonde hair cascaded with it. It was a decidedly feminine maneuver. "Now, what's this I hear about you fucking up another account?"
I stammered, "Yes, I- I'm so sorry, boss. I tried so hard to keep it."
"You tried so hard to keep it? It's all about the bottom line, dummy. It's amazing that despite all of my efforts you are still underperforming. Ok, listen lackey. You need to be punished again. However, I'm going to be busy today training Amy and don't have time to do it myself. Here's a list of what you need to get from Home Depot. I'll explain when you return."
I went to the hardware store and purchased the required items. I could only imagine what it was for. On the way there, I thought about Amy. Carissa had decided to hire the little bitch in some capacity. Amy might have been little and cute, but gosh what a cunt she was. I recalled how she took such joy in my destruction. It was like she never forgave me for those times I tried to get with her. Just great. Now we had another woman in the office to participate in my daily humiliation. I wondered what Amy would be doing and why Carissa had to train her.
I returned to the office with the hardware Carissa had requested. It was several 2x4"s, a hammer, a saw, nails and a triangular-shaped piece of hardwood. I couldn't imagine what she had in mind. When I returned, Carissa was busy with Amy in her office. Carissa took one look at me and said, "Why are your fucking clothes still on? Strip and come back in here when you are properly exposed.
I returned and Amy smiled brightly when she saw me. "Well, hello Chuck," she said. She was so hot in her little purple skirt and white button-down shirt. She wore 5" high heels that helped accent her feminine curves even though she was a little wisp of a young lady, probably 4'10" and not 100 pounds.
"Hello, superior Miss Amy," I said. Both women nodded their head in smug acknowledgement of my addressing a woman by her proper title.
"I see your training is paying off, Cariss," said Amy.
"It’s a slow process, but I’m starting to see results," said Carissa. "Ok, lackey, we need to measure you. Stand here on your tippie toes." I did as I was told. Carissa measured the distance from the floor to my groin and jotted down the number. She tucked the tape measure beneath my dangling balls, and held her hand there – an intentional maneuver designed to arouse me (It worked). She pulled a piece of paper off her note pad and handed it to me. It was a crude diagram of some kind of weird wooden structure.
"I want you to work on this in your office this afternoon. I expect it to be complete by four. Bring it in here when you're done," said Carissa.
"Yes boss."
"Well, what are you waiting for? Get your hairy rear end out of my office and get to work."
I immediately turned and left, with Amy's sweet high-pitched laughter trailing me out the door.
All afternoon I worked on the project. It called for me to build a frame of 2x'4s and then place the triangular piece of wood on top, sort of like a balance beam - except Carissa had ordered me to have a sharp angle of the triangular beam facing upwards. I was actually pretty good at construction and took pride in doing a thorough job. Once I had the job done, I returned to the office, naked of course, at four. Carissa was still working with Amy, but they both smiled when I walked in.
"Let's see how it turned out. Oh, perfect," exclaimed Carissa. "If only you could sell so well, maybe you wouldn't be in this predicament." Again, Amy the kiss-ass laughed at my boss.
I was ordered to position the beam in the middle of the room. "Good, now climb right on top of it, one leg on each side." ordered Carissa.
I never imagined I was building something for my own punishment! I felt tricked and outsmarted yet again. As I struggled to climb aboard the object, Carissa explained it to Amy.
"I needed something that would rack his balls without any effort from any of us. Don't get me wrong, sometimes there's no substitute for a good healthy kick in the groin, but we're busy and this will solve all our problems."
They watched as I struggled onto the beam. Amy laughed as she saw me strain with effort. I had to stand on my very tip toes to keep the sharp wood from digging into my groin. "You're a genius, Cariss," Amy said giggling.
"You haven't seen anything yet, girlfriend. Check this out. Ass clown - there's one more set of instructions when you're using your new balance beam. Not only do I want one leg on each side of the beam, I want to see one BALL on each side of the beam."
Amy began squealing with delight. I struggled to comply with Carissa's orders. I felt the triangle dig into my scrotum as I strained to stay on my toes. Any time I relaxed my ankles I would sink down onto the sharp hardwood and it would dig into my sack. Also, if I shifted my weight from one side or the other it would cause one of my balls to get trapped between my inner leg and the wood.
The two women stood next to me. "Now that's just perfect," said Amy.
"Needless to say, if we check on you and your pent-up ball bag isn’t properly straddling my balance beam, you will end up over the lap of a woman in this office. Am I clear?" said Carissa.
"Yes boss," I grunted. As exhausting as this was, I had grown to become terrified of bare-assed spankings and would do ANYTHING to avoid them.
Amy couldn't stop laughing. "You are awesome, Carissa. Just awesome. You've taught me things about men I never knew."
"Glad to help. You’re my protégé," said Carissa suddenly quite serious. Then she turned to me. "I'm giving you a half hour for starters. Keep quiet while we do our work."
I stood there for a half hour. After fifteen minutes, my leg muscles ached sp badly. I had to rest them. As I did my balls were punished by the devious contraption. I had no choice but to grunt from time to time. Each time I did, the ladies would look over and share a good laugh.
To top it off, I could hear that Carissa was training Amy on selling techniques. It began to occur to me that I might be replaced. I felt panic!
The women reached a break and Carissa announced that it was time to bring Joan and Gina in. They ushered the other women in who crowded in front of me and laughed at my predicament.
"I have an announcement to make," said Carissa. "Effective immediately, Amy is replacing Chuck as Regional Sales Manager. I've decided to keep Chuck on as Amy's secretary. Joan, you're being promoted to executive assistant for me. Chuck, you no longer report to me. You report directly to Amy, and you have a dotted line to Gina."
The room exploded in celebration and laughter while I turned red-faced and angry. Of course I was upset, but didn't show it. Carissa removed me from the beam and the women showed me my new cubicle out in the middle of the office next to Gina.
"I know this must be hard for you," said Carissa in front of all the other ladies, "to be outmaneuvered and outsmarted by women. But just think - you still have a job. I suggest you make damn sure my new sales manager is happy. If I get bad reports from her or Gina, you'll be out on your ass."
Before I left the room, Amy informed me that she wanted me in at seven in the morning from now on so I could make her fresh coffee and be ready to answer her calls. "Oh, and even though I'm your boss, I'd actually prefer if you continue to refer to me as Superior Miss Amy," she said, smiling. “Do you understand?”
As angry as I was, I fell to the floor and kissed each of Amy’s high heels. “Yes, superior Miss Amy.” The women seemed satisfied with my performance and I managed to avoid any OTK correction. Thank god.
"Let me know if he gives you trouble," said Gina. "I'll blister his ass for you."
"Thank you, Gina. I think it will be best if we all share in keeping his ego in line," said a very confident Amy.
Just great, I thought. I had gone from being supervised by a little blonde pussy to being supervised by a tiny red-headed pussy.
When I got home that night, I had to relay the news to Lydia. To my surprise, she had heard the news and wasn't upset. "I know you'll be getting a pay cut," she laughed. "That's ok - my trust fund kicked in two months ago. I didn't tell you. I don't need your money anymore. But I think I'll keep you around just as long as you do a good job cleaning and tending to my needs. You've been a much more loyal and subservient husband since I took control of your orgasms. I suggest you keep it that way."
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At work, Amy was such a bitch. It was as though she had taken a cue from Carissa. She was so high handed with me. Most of the time, she just ignored me. When she needed me it was for the most menial of tasks, like mailing envelopes. When I displeased her, she preferred to just put me onto the beam rather than deal with me herself. She usually gave me an hour on the beam. This caused me a great deal of trouble, for I could not hang on for more than 35 minutes, tops. Then, for the last 25 minutes, I would literally have no choice but to shift painfully from one nut to the other, a self-busting that would result in an extremely swollen scrotum, something Amy happily pointed out to the other ladies in the office.
One afternoon, she called me into her office.
"Cariss and I are going on a sales trip tomorrow. We'll need you to join us, as there is some heavy lifting that needs to be done and it's the one thing your good for."
She instructed me to book them at a boutique hotel while I was to book myself in a cheap motel down the street. "This is the O'Leary account, the one that you fucked up," she said in that rapid-fire sassy tone of hers that reminded me of a younger Carissa.
I thought of the O'Leary account and that horrible bitch, Kara, who I didn't get along with. I only hoped she wouldn't see me, though I suspected she would. Kara had to be the stupidest cunt alive. Of course, I probably shouldn't have told her that, but I had done it in frustration.
Amy brought me back from my thoughts. "Yeah, you remember, the woman you called a stupid cunt? Well, we've convinced Kara to sign back up with us. It was easy once Carissa explained what has become of you. We’re going to make sure Kara gets to witness your humiliation first hand. Yes, Chucky, you'll be eating your words. Now get the fuck out of my office."
I didn't sleep much that night. The following I picked up Amy and Carissa and we drove off to the hotel.
"We're meeting Kara in our hotel room at three. That should give us enough time to prepare you for show time," laughed Carissa.
For the rest of the two-hour ride, the two of them chatted with each other about various work and non work related stuff. They sat in back as I chauffeured them around.
When we got to the hotel, I was forced to immediately strip down. "Kara will be here in forty minutes," said Carissa, pulling out a pair of lipsticks and tossing one to Amy. "Let's do this."
I was made to lie on the bed, naked, while the ladies went to work with the lipstick. Amy put her dainty hands on my thighs, which immediately caused pressure in my groin. She wrote "Kick them please" on the inside of each thigh and an arrow pointing to my balls. Carissa sat on my stomach and wrote "LOSER" in big block letters across my chest. She then had an arrow pointing to my face.
"Turn over, ass clown," said Carissa. The two of them started writing on my back and upper legs. Then my ass. They were giggling the entire time. When they were done I was made to look in the mirror. They had written, "Spank me please," in big letters on my back with arrows pointing to my ass. Then on my thighs it said "Teach me respect," again with arrows pointing to my ass. Then finally, each ass cheek had a bull’s-eye drawn on it, with the center of the bull’s-eye focused on the most sensitive piece of flesh on my ass. I hadn't been spanked for five days, which I've come to learn, is an eternity, so other than a few old bruises my ass was due for a feminine whupping.
"Now I think he's ready for punishment," said Amy.
"Indeed," smiled Carissa. "Now lackey, when the WOMAN who you referred to as a stupid cunt gets here, you are to put on an immediate show. I want you to get on your hands and knees, wiggle your ass, and spank your ass with one hand and your balls with the other. You are to apologize and absolutely BEG her to spank your sorry behind. If Amy or I don't think you're doing a good enough job, we'll inform Lydia and I'm sure your chastity will be extended. And I hear you're so close to release, so DON'T disappoint us."
"Yes boss."
This was going to be horrible. I hated Kara. She was in her early 30s and had always acted so aloof with me, as though I was her inferior. Now as it turned out, she was right. She was one of those squeaky wheel customers who always wanted extra service. One day I had had enough and thus the "stupid cunt" comment. I remember how her voice dropped and she said, "What did you just call me?" And I repeated it. It didn't matter that she was an important customer. And now I would pay the price.
At three, there was a knock on the hotel room and there was Kara. She was a skinny brunette with a narrow pointy nose. She kept her hair short, but even I had to admit she had pretty eyes and looked quite feminine. Today she wore a casual floral skirt with sturdy black leather shoes and a lime colored top, which matched some of the color on her skirt.
We hadn't spoken since the famous incident. I assumed my position on the floor as instructed while my two superiors greeted Kara warmly and invited her in. Once they were done I crawled to her feet and kissed each toe. Then I began slapping my ass and saying "I'm sorry I called you those horrible names. I'm the stupid cunt. Please punish me, superior Miss Kara. I’m the stupid cunt! I’m the stupid cunt!"
Kara took a deep breath and then began absolutely cackling with laughter. "Oh my god," she said and began to laugh some more as Amy and Carissa just smiled.
I continued to kiss her feet and beg. She kicked me in the mouth somewhat firmly, enough to stun me and said, "Ok, wimp. That’s enough.”
I moved back away from her. "Roll over and spread 'em!" ordered Carissa to help break the awkward silence. I rolled onto my back and spread my legs. "I'm sorry, Superior Miss Kara," I said again. "Please kick my balls for me."
"With pleasure," she said, stepping forward and delivering a well placed kick in my groin.
"Kick him again," encouraged Carissa.
She stepped forward and kicked me again. I squeezed my legs together and attempted to roll onto my side, but I heard Amy’s tyrannical high-pitched voice, “Roll back onto your ass and spread ‘em! Thank her properly and ask her to kick you again!”
"Thank you, ma’am," I gasped. “Please kick me again.”
"I had no idea that could be so satisfying," said Kara. "This is fantastic. [Kick, Kick] Thanks so much for arranging this."
"For a client like you, it's our pleasure," said Carissa. "He's been fired from his sales position. And I can assure you Amy will manage your account with a great deal more energy and care."
"I have no doubts," said Kara. "What do you have to say for yourself, you stupid cunt?" she asked me, planting her foot in the middle of my scrotum. She wore pointy shoes that splayed my balls apart, much like the contraption back at the office.
I had no idea what to say. "I'm sorry. I've learned my lesson," I managed to sputter.
Then to my surprise, Amy took over. "Like hell he's learned his lesson. He has a lot more learning to do." She reached into her pocketbook and pulled out a hairbrush. "Kara, I haven't had the opportunity to give him a good hard spanking since I took over his position. Make yourself comfortable. I think you'll enjoy this."
"I think so too," said Kara.
With that, for the first time I went over Amy's little lap for a little OTK discipline. Or should I say, a LOT of OTK discipline. Amy blistered my bottom fiercely. It was as though she was making up for her little size. I won't go into too much detail, but let's just say I did a lot of crying Amy led an enjoyable (for them) male hating verbal session.
Toward the end of my punishment, Carissa took my head and made me face Kara. "Who is the stupid cunt now?" asked Carissa.
"I am!"
"Then tell Kara."
"I'm a stupid cunt, Kara." Kara just laughed.
When it was over and many tears had been shed, Carissa asked Kara is there was anything else they could do.
"Now that you mention it," said Kara. "I think it would be really cool if you, like, turned him into a sissy and made him suck cock. You've done everything else there is to do. But why not turn him into a dick-loving whore? Then he really would be a stupid cunt!" She laughed. I had no idea she could possibly be this devious.
Amy and Carissa turned to each other. "What a wonderful suggestion!" Carissa said. "I'll call his wife tonight."
"Ladies, this has been an incredibly satisfying day. Well done. I know we're going to do great work together. Thanks again."
Chapter Eight – Suck It
Saturday was a day I had been looking forward to for a very long time. After two agonizing months, this was the day I would finally get a chance to have an ejaculatory release.
I was incredibly attentive to my wife all morning long. It occurred to me how owned I had become at this stage of the game. Lydia had me conditioned like a dog to respond to her commands with total devotion. I respected and feared her. In fact, I guess you could say I had a great deal of respect for all women in general.
Lydia surprised me by informing me Anna would be joining us today. I knew what that meant: More humiliation. But I vowed to be completely deferential to her as well. I didn't want to screw this up. And Anna was not a woman to be trifled with, even though deep inside I still felt like she was an annoying little hussy.
Lydia had me stand beside her as she applied make-up for the day's "festivities." She wore a turquoise floral dress. I had to admit she looked stunning as she admired herself in the mirror and carefully applied her eye liner. I stood, head hanging in shame, waiting for my orders, like the fool I had become.
The doorbell rang. "That must be Anna," said Lydia. "Go answer the door. When she enters, kiss her feet and then offer your backside to her. Tell her you're a bad boy, and beg her for additional female correction."
"Yes, Ma'am," I said without hesitation, though I could feel my face reddening. You would think by now I would have become accustomed to being spoken to that way by my wife, but my face always turned red, probably because once upon a time I was a misogynist and it never failed to humiliate me when I was spoken to in such a manner by the women who now ruled my life. And I truly hated submitting to Anna, the short, chunky lawyer-bitch, who never liked me to begin with and now had gained this control over me. Anna was a mean, vindictive woman and I knew she wouldn’t take any mercy on me. My heart began beating faster.
"Hurry up!" Lydia said, not taking her eyes off the mirror.
I rushed to comply, my penis bobbing up and down the entire way down the staircase. I could feel the air between my legs since I was naked as usual other than the restricting device attached to my sex organ. As I thought of who I was about to greet, my face turned red and I felt an urge to run away.
Anna clenched her hands together and let out a big giggle when she saw me lie on the floor and give her a “proper” greeting. "Look at what's become of you," she said. “All that obedience training is paying off, just like it always does.”
She wore a striking dark purple dress with a big leather belt that helped highlight her full-bodied curves. She had matching high heels that made her look taller than she was. I had to say - probably because I was so horny - that Anna looked like a real woman. Plus, the scent of her perfume invaded my senses and made my penis begin to twitch against its cage.
Anna was still a total bitch as far as I was concerned, and she could stand to lose 15-20 pounds, but I had no choice but to recognize her as my superior. As I took my place at her feet to offer her a proper greeting, it occurred to me that she Anna had been right along - maybe I had learned a few things about respect for the female. As she stepped inside the house, I planted several kisses on each shoe. I heard her laugh again and say, "Someone has had a serious attitude adjustment. And they say corporal punishment is a thing of the past. Look at what a wonderful impact it has had on you."
"Thank you, Superior Miss Anna," I said, and then I remembered to turn offer my ass to her. "I'm a bad boy, Miss Anna, and could use additional female correction." Then, as instructed by Lydia, I gave myself a couple of slaps on my own ass.
Anna howled with laughter. "There will be plenty of time for that later, if necessary, so make sure you behave today. Now where's the head of household?"
As if on cue, Lydia appeared at the top of the stairs. "Hey, girlfriend!"
"Oh there you are." She walked right past me and greeted Lydia with a warm hug, while I stayed on the floor and awaited instruction. "Look at what you've done. I'm so proud of you. Does he have any idea what we have in store for him?"
"Of course not!" laughed my wife. She turned to me. "Charlie, we're taking a road trip. Run upstairs and put on some slacks. No underwear! And a collared shirt."
"Yes, ma'am," I said. I ran upstairs while the women exchanged greetings. The thought of a potential orgasm caused me to dress in double speed. Back downstairs, the women were talking on the couch.
With that, I followed the women out to the car. They made me hold the door for each of them - they both sat in the back - while I drove. They directed me to the local high end mall on the opposite end of town. When we arrived, we headed right for the lingerie store. It was a French boutique, which specialized in lingerie for women who had “graduated” from Victoria's Secret.
Several fashionable saleswomen were busy with customers. I could see where this was going and my heart began racing. Unfortunately the store was quite full.
Lydia walked us over to a pair of young saleswomen who were chatting idly near the back of the store. Both were dressed professionally in dark, tight pinstriped suits. Neither of them could have been more than 20 years old. They had similar figures, both around five and a half feet tall and quite fit. One was quite beautiful, with long dark hair done up in a sixties bee-hive sort of hairdo that I guess was making a comeback. The other was blonde and more cute than beautiful. She even had some of her baby fat left on her cheeks.
"Hi, girls, we'd like to feminize my slave husband here," she pointed at me. "We intend to purchase this bitch a full wardrobe of panties, stockings, bras and corsets. Can you help us?"
The two girls turned to each other and their faces absolutely lit up. "Sure," said the blonde. "Come right this way, ma'am."
"Please, I'm Lydia," she said, "And this is my friend Anna. The only person here who can call me ma'am is this bitch right here," she pointed at me. "And he should refer to both of you as ma'am as well. You can call him, bitch."
The girls turned to each other and giggled. "Sounds good to us," said the brunette.
"Lydia, Anna, bitch, follow us," said the blonde, causing a wave of laughter.
I made to follow and felt a ringing in my ears as Anna of all people slapped me in the side of my head. "What do you say, bitch?"
"Thank you ma'am."
"No problem, bitch," said the blonde, laughing. "I know about femdom relationships. One of my girlfriends treats her boyfriends this way. Maybe it's time I did as well."
With that, we went into the back room.
The next hour was humiliating, frustrating, and also highly erotic. The young girls paraded me in front of Lydia and Anna in one sissy outfit after another. My name soon became "sissy bitch." Everyone except me seemed to be having a grand old time. When I was first stripped naked, both girls were curious about my chastity device. Anna explained that it was a tool women used to keep men in line.
"You mean so he can't jerk it?" asked the grinning and astonished brunette.
"Exactly!" said Anna and Lydia in unison.
"Wow, sucks to be you," said the blonde.
I hung my head in shameful agreement.
Both sales ladies got a serious education in female dominance. They both reveled in my humiliation. At one point, they put me in a set of crotchless panties and stockings and showed how the outfit would provide "full exposure and extreme humiliation," as the blonde put it.
"There will be plenty of that," said my satisfied wife, "I intend to pimp him out and introduce him to cock. He won't like it at first, but he'll learn to LOVE it."
This caused a fresh round of laughter. It dawned on me that Lydia was dead serious. I began to fret about when or where this might happen. Lydia seemed to sense my apprehension.
"Look, girls! Sissy hubby doesn't like what we're talking about. Well, there's a quick solution for that. Across my lap, NOW, bitch!"
Across Lydia's lap I went. Then, she reached into her purse and pulled out a sturdy little hairbrush that she had been using for situations such as these. My ass had grown calloused over the past couple of months from all the spanking I had received, but the women in my life never failed to locate my weak spot and exploit it with their hard hairbrushes. I saw the animated look on the girls' face as my fresh tears began to flow.
"Isn't it a wonderful sound, girls?" asked Anna.
"Rebecca would LOVE to see this," said the blonde.
She left and moments later returned with an older woman, who I guessed was the store manager.
"Oh what do we have here?" said the woman in a British accent. "Ladies, allow me to introduce myself, I'm Rebecca - the store manager. It's great to see women like you visit our store. Please let me know whatever I can do to be of assistance."
By then, I was sobbing and kicking up my legs. Lydia put the hairbrush back in her purse and ordered me to thank the store manager for the privilege of shopping for my new "sissy bitch" outfit.
I still wore a pair of stockings and also had a pair of light pink frilly panties that were down around my knees. I stumbled over to the sales manager and began worshipping her and thanking her as instructed.
"Oh I'm doing it for your wife - not you, weakling." she said. She was a particularly beautiful and mature woman in her 30s, with a full set of lips. She wore a fashionable skirt and knee high boots, which I kissed.
"Is that a chastity device he's wearing?" asked the knowing sales manager.
"It is. Show Rebecca what that captured and controlled penis looks like!" ordered Lydia.
I immediately rolled onto my back at Rebecca's feet, and spread my legs as I was trained to do. Now all five women had full viewing access to my captive genitals, which must have amused them based on all the heartfelt laughter.
Rebecca put her hands on her hips and beamed down at me. "You know, there's something about poorly endowed men. They always seem to end up this way. Now, why would I even call you a man? Real men have real penises. That little thing couldn't arouse a 12 year old girl." For emphasis, she stuck her boot between my legs and gently prodded my desperate organ.
"A little dicklet such as this belongs in a nice pair of panties. Now stand up and pull up your new undergarments so we don't have to spend another moment looking at your pitiful excuse for a cock."
The room erupted in laughter as I did as I was told. I had to admit the panties felt good as I pulled them tight.
"Wait, Rebecca, before we finish, would you like to spank him?" offered Lydia.
"Oh dear, I'd very much like that, but I need to get back to the main floor. Oh, what the hell, I could at least give him a few slaps."
"Wonderful," said Anna, offering her chair. "Take him over your knee. It's the only proper way to teach respect."
With that, I went over Rebecca's knee. She refused the hairbrush instead choosing to spank my already tender ass with her open hand. The crisp slaps and my accompanying cries soon filled the room, as she spanked me to her complete satisfaction.
"Here's my business card," she said, when she was finished. Please call me any time. Good luck with this sissy wimp. Oh, by the way, if you need high heels for your bitch, my friend Leanna has a lovely boutique on the other side of the hall. You can't miss it. It's called Leanna's."
With that, we were off to the shoe store for more humiliation. By the time I got home, I had a full wardrobe of feminine attire.
I thought the day might be finished, but I didn't realize it had only just begun. In fact, it was about to get worse.
"What do we have, about a half hour before they come?" asked Lydia.
"I ordered them to arrive at 3:00 sharp," said Anna.
I knew better than to ask questions. I assumed it was more women to revel in my humiliation, but the fact that Anna used the word "ordered" got me thinking.
"Let's dress up this silly slut and make her look nice and pretty for her guests," said Lydia.
They brought me upstairs and ordered me to undress. Then, together they selected just about the frilliest outfit they could find. It was a pair of light pink satin panties with white ruffled laced edges. They ordered me to pull it tight around my ass until it wedged into my butt crack. I felt my cheeks turn red as I was hit with the realization that felt great.
Anna: “Look Lydia, I think he likes it.”
Lydia: “Is that true, bitch?”
I had to admit to them that the panties felt good. The women smiled and winked at each other. They had me put on a matching lace corset, bra and stockings. Then I was forced into a pair of hot pink 6" high heels they had purchased at Leanna's. Then, each woman took one of my elbows and escorted me over to the mirror. I kept slipping and turning my ankles, but neither woman seemed to mind. They were too busy insulting me.
Lydia: "Look at what an ugly slut I married, Anna!"
Anna: "If this whore is to make any dicks hard we're going to have to primp him up a bit."
With that, they took out some make-up and began fixing me up. First, Lydia wrapped a pink bow around my hair. Then Anna did my eyeliner, except she put too much on. Lydia applied a healthy amount of red blush to my cheeks. Then, to top it all off, Anna took a big thick tube of lipstick and smeared a healthy amount on my lips. She ordered me to smack my lips for them and they both got a good laugh as I did. They forced me to look at myself in the mirror and I have to admit I almost resembled a pretty slut. Then they made me walk back and forth and sway my hips in exaggerated fashion, so I looked like “the slag whore that I (was).”
"It's almost show time now!" said Anna, glancing at her watch.
"I can't wait," said Lydia, clasping her hands together. "This is going to be sweet revenge."
"You've had quite a bit of that already, don't you think?" asked Anna.
"Yes, but this will be special," said Lydia.
I had no idea why this would be special. What was the difference between this and some of the stuff I had already been put through by Carissa at work? It was just more of the same. If it meant I'd get to cum, then I would do anything they wanted. Little did I know what "anything" meant. These women had me so dominated and controlled, not to mention completely clueless at the devious plans they had in store for me.
The doorbell rang and the women excitedly escorted me downstairs. "Why don't you answer it, dear? I think it's for you," said Lydia.
"Yes ma'am," I said, opening the door expecting to be laughed at by a new group of female faces.
Imagine my surprise when I opened the door and discovered two big guys, both bald with goatees. And here I was dressed up like a complete sissy slut. It now dawned on me what was to take place. I turned and began waddling toward the steps, trying to find a place to hide. But thanks to the high heels, I couldn’t move that fast, and I twisted my ankle painfully.
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Anna stepped in front of me with a big smile on her face. "Not so fast, sissy bitch." For a moment I was tempted to push her out of the way but I knew that wasn't a realistic option. I heard my wife's voice.
"Charlie, these men are here for sexual satisfaction. As I'm sure you can imagine it won't come from me or Anna. Quite frankly, we're out of their league. No, they need a total cock-loving whore and you're it. Now you have a choice. You can either service their hard dicks the way we want you to. Or, you can resist and they are still going to bang your virgin asshole. In fact, go ahead and resist. It will be more entertaining that way, and you won't get to cum. What the fuck do I care? I’ll just leave your chastity belt on if I sense your lack of total enthusiastic cooperation."
I turned, weak at the knees and looked the men.
"That's what I thought," said Lydia. "Now get on your knees and warm them up."
I fell to my knees in front of the two men. Lydia and Anna stood next to the men and unbuttoned their jeans for them. They pulled out the men's hardening cocks. Both were in the 7" range.
"Who wants to go first?" asked Lydia to the two men. Lydia and Anna teased the men's rapidly stiffening dicks. It took no effort on the part of the females. They merely gripped the sensitive organs and the penises immediately responded, turning hard and purple.
"These are a couple of maintenance guys from my office," Anna explained to me as she squeezed the shorter one's hard cock. "When I told them what I had in mind, both seemed eager to help fill in so to speak."
"Charlie," said Lydia. "I want you to love their cocks. Suck on them as though they are your salvation. In time, you'll learn to enjoy it. And if you don't, I don't give a damn."
With that, I took one man's cock in my mouth while stroking the other one. The penis felt hot and stiff as it throbbed up against my throat. Although I felt queer, I had to admit that there was something enjoyable about taking a good stiff cock in the mouth.
Anna: "That's it. Suck it like you mean it! I think he's a natural, Lydia."
Maybe it was because I was so horny, but I was almost enjoying sucking this guy off until Anna forced my head forward and his bulbous head gagged the back of my mouth. I began choking and tried to pull away. Anna grabbed my hair and pulled me forward while also squeezing my throat and restricting my airways. She was stronger than she looked.
"Take that cock back in your mouth NOW, BITCH, if you ever want to cum again." she yelled harshly into my ear. She had me. As the realization hit me of what she was subjecting me to, I could feel the humiliation well up deep inside my brain.
I choked a few more times and tears poured down my cheeks as I gagged mightily and groaned in distress. But Anna was indifferent. She just held me firmly and said, “Deep-throat that hard cock, you fucking ten cent whore!” I felt the salty taste of pre-come and my throat began to relax and accept its uninvited guest. “Fuck this bitch’s throat. That’s it,” Anna said to the dude who was doing it to me. “I told you he’d love it, Lydia!”
A few minutes later, I heard the man began to groan. Anna pulled me back by my hair while continuing to hold my throat. “Slide it out a little bit so we can see it squirt,” she ordered the man.
I looked up and Lydia was pointing a camera at my face. “Smile, Chuck,” she said, with a cruel grin. At that moment the man began shooting big chunks of semen into my mouth.
"Stick your tongue out further, so we can watch!" ordered a beaming Anna. "Don't swallow yet, cum-guzzler," she said as she increased the pressure on my throat.
The man groaned as he spurted away. I felt a fountain of hot sperm splash in my mouth.
"Now face your wife, MOUTH OPEN, TONGUE OUT!" said Anna. I turned and Lydia snapped shots of me in this ridiculous position.
"Now, swallow the entire salty treat," said Anna, still holding me like the bitch I had become.
I swallowed and it tasted gross. I felt my gag impulse take over as my throat sought to reject the foul-tasting gunk. Sensing my reticence, Anna inserted her hand beneath the waistband of my panties and squeezed my balls. She pulled on my hair with her other hand while fixing a determined gaze upon me.
"I said, Swallow. The whole. Fucking. Load.”
How had I allowed this little bitch to humiliate me so thoroughly? This thought went through my head as my stomach heaved in protest at the forced meal.
I heard my wife's excited voice: "Now that's how I like to see hubby dominated. Bravo, Anna!"
"I'm only getting started, girlfriend," Anna said. "I'm going to teach this floozie to absolutely LOVE dirty semen." She turned to me. “In no time, you’ll need cock all the time, faggot!”
"I'm sure Carissa will be thrilled," said Lydia. "She wants him trained to service her clients. I can't wait to show her the photos."
"Well, let's make a few more photos. It's Billy's turn to be serviced," said Anna.
With that, the larger of the two men brought his cock over.
"Wait just a second, Billy," said Anna. "Charlie, I want you to BEG this man for his cock. C'mon, open that mouth for us, stick out your tongue and tell us how hungry you are for more spunk. Do it!"
"I- I'm hungry for more spunk," I said, not believing the words as they came out of my mouth. In time, Anna would prove correct. I would learn to love the penis, but I wasn't there yet.
"Suck on his big hairy ball sack and beg him to fuck your mouth," said Anna.
I positioned my head between the man's legs. He wasn't exactly clean. His balls had a thick nest of hair on them. Once again, my gag reflex kicked in as I rolled the balls around in my mouth.
"Fmmmph my Mphhh," I begged, mouth full of scrotum. Lydia and Anna laughed heartily and made fun of my pronunciation.
"Ok, Bill, give it to him."
Bill pulled his hips back and began fucking my mouth, shoving his dick deep down my throat as I just held my mouth in place and allowed him to use me. Satisfied that she had trained me properly, Anna sat down on the couch next to Lydia and crossed her legs.
The next thing I knew, I felt a pair of strong hands grab hold of my hips. Then my panties were yanked rudely down and I felt a man's thumbs prying my ass cheeks apart. Then I felt the protrusion and knew what it was. The other man was raping my asshole.
Then I heard Anna, "The only thing we need is some popcorn for this show. Let him have it, boys!"
Lydia: "Use the fool as a spunk bag!"
Anna: "But don't cum in his anus. I want him to learn to love the taste of sperm. All discharge should be directed into the cum guzzler’s mouth."
One of the men said, "yes ma'am."
This caused Anna to sigh with satisfaction. "Ah men," she said. "So easy to control."
I felt the dick penetrate my asshole and it hurt quite a bit. I made some weird squealing noises in protest, which caused Anna and Lydia to laugh and slap their skirted thighs. But once he started pumping, I could feel the pressure and it was mildly satisfying. Soon after, Billy shot a massive load down my throat while the women continued to cheer at my defilement.
The men changed positions just in time for the other man to splatter his second load onto my waiting tongue. His cock had the stench of my ass, and I felt myself shying away.
Anna came over and reached between my legs, securing my balls again. She then ordered me to "Clean that dirty cock off thoroughly. DON'T disappoint me, or your wife. If I don’t sense some real effort, I’ll have you over my knee and trust me when I say you want to avoid that.”
She was right about that. I sucked on the cock that had just been in my ass with as much passion as I could muster. By now, my mouth was lubricated with so much cum that it began to ooze down the corners of my mouth.
Anna took me by the neck again and turned me so I was facing Lydia, who still held the camera. "You've got man chowder all over your chin, sissy bitch. Let me help you with that." She scooped a big gob of cum that I had failed to swallow. It gathered on the inside of her long fingernail. "C'mon, show your wife how much you love this. Beg for it! Stick out that tongue!"
Anna held the spunk away from me as I begged. She made me beg even louder. Finally she said, "Fine, have it your way, you floozie," and she smeared the gob onto my tongue. She spent the next minute finger feeding me the discharge that had landed on my face.
I felt used and abused. And oddly, I didn't really mind it. I hadn't had any type of sexual contact in two months and it felt good to have my ass pounded. If this was all I was going to get, then it was better than nothing.
In a half hour's time, I had swallowed four big loads. I could feel the dried cum caked all over my face.
I was then made to kneel in front of my female superiors. Clearly pleased with herself, Anna stuck her finger underneath my chin. "Think of all the semen you've eaten today. You must have a billion little spermies swimming around your tummy, faggot." Anna then made me escort my satisfied customers to the door where I was ordered to thank them for the good time and beg them to come back soon.
"We have one final humiliation in store for you today," said a thrilled Lydia. "I think it's only fair that you do the honors, Anna."
"I'd be more than happy to."
Anna removed her keys from her pocketbook, and to my great delight she ordered me to kneel in front of her. She reached between my legs and unlocked my penis. I looked down at my quivering prick. It was quite discolored and it throbbed away as it slowly hardened for the first time in months. It seemed almost uncertain of itself since it was so used to denial.
"I don't know how you put up with that pathetic little thing for so long," said Anna to Lydia.
"Me neither," she said.
"Well, enough about that. Those days are over. Now, cum whore, lie on the floor and throw your legs back over your head," ordered Anna.
Without a moment’s hesitation, I tossed my legs up over my head and pointed my suddenly emancipated penis at my own mouth.
Lydia then reached into a drawer and pulled out a thick white wand. She clicked it on and it began vibrating. Then she handed it to Anna.
Anna turned to me. "You've sampled so much other sperm today, I think it's only fair that you should get to sample your own, don't you think, fool?"
"Yes ma'am."
"But I'm not going to touch that dirty thing. Thank goodness for modern technology," said Anna.
She placed the vibrator on the underside of my penis and the two women gazed down at me. I immediately felt the stirrings of a powerful orgasm and began groaning.
"I think he's losing it! Talk about a 30 second wonder!"
"Come on, bitch," said Anna, as the pressed the vibrator down on the most sensitive part of my shaking penis and smiled triumphantly at me. "Give it up for your superiors!"
With that, the cum began oozing out. At first it didn't really shoot out. I think I was so pent up from so much inactivity that my ejaculatory ducts must have been gummed up. It came out like snot dribbling out of a sick person's nose. Except it kept coming and kept oozing until gravity took over. The first glob landed in my right eye, drawing laughter.
"Eww," said Lydia.
"Open fucking wider!" said Anna, pressing harder on my penis and adjusting her aim slightly. The next glob landed directly on my tongue.
Then I started spurting as the main orgasm swept over me. I can't possibly guess how many spurts came out, but by the time I was finished, my mouth was almost overflowing with my own discharge.
"Don't swallow yet!" said Anna. "We want to hear you gurgle it for us. In fact, I want you to gurgle the alphabet for us!"
I was made to gurgle the entire alphabet before finally being given permission to swallow my load.
When it was finally over, Lydia locked me back up and ordered me to go to my room. Over the next hour or so I could hear female moaning. It sounded almost as though my wife and Anna were hooking up, but it couldn't possibly be the case. Or could it? I was too busy in a post orgasmic depression, wallowing in a confused male haze as I tried to figure out how I ended up like this.
END CHAPTER 8
Young Blonde Executive – By James Pendergrass
Chapter Nine - Cuckolded
Having been pimped out by my wife and Anna, my submission to the superior gender had officially reached a new level of degradation. Sunday night, my wife laid out the outfit I was to wear to work the next morning. She informed me that she'd had a lengthy discussion with Carissa and they agreed it made sense for me to be fully feminized at the workplace. After getting Marsha’s ok (Marsha was semi retired and spending a year in France, now that she trusted Carissa with the keys), Carissa informed Amy, Gina and Joan of the new arrangement and it was relayed to me from Lydia that all the women were very much looking forward to seeing me in my new work outfit. In the meantime, Lydia informed me that she had emailed the photographs of Saturday's escapade to the entire office.
I glanced at the outfit my dominant wife had laid out on the bed for me. She had selected a tiny pink miniskirt made of cheap fabric with a matching pink top that was more a sports bra than an actual top. I was made to wear the hot pink high heels we'd purchased the previous day. But the kicker was the panties. She picked out the sluttiest pair of see-through bikini panties. They were nothing more than a pink strip of silk fabric that would serve to bunch my imprisoned package in front of my body. The only place there was any appreciable fabric was on the edges, which were made of a ruffled ultra-feminine knitting. The back of the panties would wedge deep into my ass-crack, leaving my behind completely exposed.
"That way, the ladies just have to flip up your slut-skirt when they want to discipline you," Lydia said matter-of-factly.
Lydia noticed my misery. "Aw, don't feel so bad, Chucky," she said, laughing at me. "At least you still have a job - and you get to serve a higher purpose. Now, go wash up and get ready for bed." She turned and walked confidently from my little room.
The next morning I put on my outfit and applied my make-up. I have to confess I got a strange thrill when I pulled the tiny pink panties up over my hips. I felt so feminine! Before leaving, I knocked on the master bedroom door so that Lydia could inspect me. Of course she ordered me to flip up the skirt and do a proper courtesy. "Don't you look ravishing," she smiled. "You’ll be a big hit at work," she laughed loudly. "Now run along."
The executive assistants were the first to see me when I arrived at the office. Joan and Gina began laughing hysterically as I staggered into the office. "I didn't know Amy had fired Chuck and hired a little sissy bitch," chortled Joan, as she positively snorted with laughter.
Gina approached me with a huge grin. "Let's see those panties, bitch," she said. "Flip up your skirt for us, you dirty little whore."
Having been savagely spanked by Gina on several occasions, her orders were not to be taken lightly. I immediately flipped up my skirt and thrust out my crotch so the women had a nice view of my tiny silk panties. They hugged my chastised penis and balls and caused me some degree of pain. I had to admit I was turned on both by the feel of the silk and the feeling of being so controlled.
"Curtsey for us, like a proper panty slave," ordered Joan. "And smile."
I forced the corners of my lips up and felt positively dizzy with humiliation as the composed women inspected me.
Joan took the opportunity to jab my package a few times with her pen. I didn't move a muscle and said, "Thank you superior Miss Joan."
"Look at how well behaved our little office slut is," said Gina. "The hairbrush truly is a wonderful thing."
"Indeed," said Joan. "You've clearly managed to spank all signs of disrespect out of our former sales exec. Let's show him to the young women that helped put him in his place."
The two women escorted me to Carissa's office and cracked open the door. Inside, Carissa and Amy were both decked out in sensible feminine business attire - dark skirts, stockings, white collared shirts, and heels. They were working on a presentation. Both of them dropped what they were doing and began laughing as Gina and Joan both pushed me forward for inspection.
"Oh my gawd," said Amy, as the beginnings of a huge smile came across her pretty face.
I hung my head in complete shame.
"Now we've officially reached a state of complete humiliation, haven’t we?" said a beaming Carissa.
“Yes ma’am,” I said. No longer did I call her boss, now that I no longer reported directly to Carissa.
"Show her your panties, bitch," said Gina. She then slapped the flimsy fabric of my right ass cheek with her open palm. If anything was to jar me to attention it was a blow on the ass from Gina. My mind instantly recalled the sheer terror of being over her lap for a full blown spanking.
"Yes Superior Miss Gina," I said, staggering forward from the blow. I repeated the actions from before, thrusting out my crotch and lifting my tiny miniskirt so that my female conquerors had full viewing access to all of my shame. “I love stiff cock in my ass and my mouth!” I said, repeating something Lydia had ordered me to do when I was in front of all the ladies.
They all burst into hearty laughter.
"I hereby declare total victory!" said an elated Carissa. "We've officially crushed the egotistical male penis!"
It took a while for the four women to compose themselves, but when they did, things got even worse for me.
"Girls, you have to see these photographs," said Carissa, escorting them over to her desk. "You too, sissy bitch. Come over here, but keep your skirt up nice and high so we can all be reminded of your complete defeat."
"Yes, superior Miss Carissa."
"Fucking right I'm superior," she said, rubbing it in. "Look what I've done to you. In fact, look at what all these women have done to you. You have become our willing ass-clown. Now just stand there and shut up while I show the ladies some photographs."
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I looked in horror at Carissa's big flat-screen monitor as the show began. And of course, I was the butt of all the jokes. The photographs featured me taking cock in every orifice. The women made all kinds of lewd comments, as each photograph appeared on screen.
"Look at the look on his face. I think he likes it," said Gina.
"He already likes it, but he'll learn to LOVE it," said Carissa.
"Who is the woman that's dominating him?" asked Amy.
"That's Lydia's lawyer, Anna," said Carissa. "She's an awesome female. She was a big factor in helping us nail his balls to the wall," she said proudly.
After a few minutes, the photos got even worse, as they focused on my face getting absolutely covered with semen. The ladies snorted with laughter as they got to a particularly lewd photograph. Anna was next to me with a determined and satisfied look on her face. She held my throat and pulled my hair back as the larger of the two men emptied his balls on my outstretched tongue. My tongue cradled his hard dick. By then, I had already taken several loads to the face and my cheeks and chin were covered with spunk. The women all made it a point to discuss every detail of this incredibly humiliating photo. They talked about what a badass femdom Anna was, and what a complete cum-guzzling slut I was.
Gina: "Look at all the spunk on his face!"
Amy: "Yeah, it's like, caked on."
Joan: "I would like a copy of that photo."
Amy: "Me too."
"You all can have copies of it," said Carissa. "In fact, we've already sold the entire series of photos to a popular femdom site. Charlie's shame is going to be witnessed by millions of people worldwide.
I could feel the panic setting in as my predicament became increasingly apparent. I again began to wonder how I had allowed this to happen to me.
Almost as though she could read my mind, Carissa turned and said, "Look, I can see the panic in his eyes. You're probably wondering how this happened to you," she said. "Right?"
"Yes, superior Miss Carissa," I said, as the sweat began coming out of my pours.
"You STILL don't get it, you stupid pervert. I used your misbehaving little penis against you. I outsmarted you and I took everything you have. I've reduced you to a cock sucking whore whose sole purpose is to serve and entertain the superior gender."
"I still don't think he gets it," said Gina. "Let me take him across my lap for you," she said, to my utter horror.
Carissa considered the offer, as I looked on, just praying she would decide to be kind for a change. I realized I was no longer in charge of anything anymore. My life was ruled by a group of women, led by this skinny 27 year old blonde bitch.
Carissa finally made up her mind: "That's a great idea, Gina. Can't have too much discipline as far as I'm concerned."
The women cheered and I was immediately placed upon Gina's lap. Carissa produced a sturdy hairbrush from her desk drawer. Gina flipped up my pink miniskirt and gave me a blistering I will not ever forget. I never forget any of her spankings, but this one was particularly savage. I screamed, cried, sobbed, and did all those things I do when my ass is violated by the sadistic, unforgiving head executive assistant of our organization. My legs positively convulsed as I tried in vain to escape. None of them cared. They just laughed and enjoyed my punishment. When it was over I had to crawl on the floor and kiss four sets of high heels as four composed and satisfied women looked on.
“You’ve ruined his make-up,” said Joan.
“Go to the ladies room and compose yourself,” ordered Carissa.
“And come back when you’re done,” said Amy. “We have additional orders for you.”
When I returned, Amy ordered me to go fetch her and Carissa some coffee while they resumed preparing for the presentation.
After serving my superiors, both of whom ignored me as I placed their coffee down on the table in Carissa's office, I sat down at a cube in the main reception area and began arranging Amy's travel plans. My feet were already sore from the painful shoes and my ass was so incredibly blistered that I found it hard to concentrate. It didn't help that both Joan and Gina bossed me around all morning long, constantly making me fetch various things for them so they didn't have to move their big asses. Their idea of 'thanks' was to reach under my skirt and give my imprisoned package a squeeze.
At lunch, Gina handed me a list of lunch requests. They wanted me to walk down to the corner sandwich shop and get everyone salads! I was maybe a bit hesitant, so Gina lifted my mini skirt and gave me one hard smack on the ass. It was more than enough to send me on my way. I felt fresh tears as I walked down to the store to get the sandwiches. I received more than a few strange glances in the store, but fortunately made it back to the office without any major incidents.
When I got back, I was surprised to see that Kara had showed up at the office. The former client who I called a cunt had a huge laugh when she saw me. Then Amy surprised me by announcing they had invited a couple of maintenance guys up that afternoon.
"They will be having a party in your mouth," she said.
"Thank you so much for inviting me," said Kara. "When I said I wanted to see him eat dick I had no idea how serious you ladies were."
"We aim to please, Kara," said Carissa. "It's our new way of doing business here. Anyway, we all love to see him get humiliated so it's not a major sacrifice."
Kara turned to me. "I hope you're hungry," she said with a big grin.
Amy then made me tell her how much I was looking forward to having the opportunity to guzzle some sperm for her amusement. She then pulled out a banana that she must have brought to work and made me demonstrate my cock-sucking technique. Like Anna had done yesterday, the petite Amy grabbed my throat and pulled on my hair while I choked on the banana.
After lunch, the maintenance guys showed up. Both were dirty-looking gruff guys who seemed excited to be there.
Carissa and Amy positioned me on the big couch in Carissa's office. I was made to lie on my back and put my legs high up in the air while my head was positioned on the edge of the couch. This way the men could take turns fucking my face while the women gathered around and cheered them on.
The first man, Hector - a big fat guy - pulled his pants down and stuffed his dirty, uncircumcised dick down my throat. I nearly choked, but was already getting better at handling penis. Soon I had a great rhythm going as I wrapped my red lips around his shaft and teased the underside of his unkempt dick with my tongue. He grabbed my ears and began pumping away in my mouth. Then he shot a huge load in the back of my throat.
"Oh, come on Hector," said Carissa. We want to see it squirt into his dirty mouth."
Hector pulled out of my mouth and positioned his spurting dick on my lips where the last couple of spasms oozed out onto my tongue. I greedily lapped up his sperm. For some reason I enjoyed getting men off. Perhaps I could relate - it was as close as I was going to get to my own orgasm on this day.
"It looks like he loves it," said Kara.
"He does. Tell us how much you love it, cum slut," said Carissa.
"I love it," I mumbled as I thoroughly cleaned off Hector's cock, flicking my tongue on his pee hole until it stopped oozing.
"This isn't even a punishment," said little Amy, feigning disappointment. "This cocksucker is enjoying himself too much."
Amy wanted me to suffer. It was amazing what a little bitch she had turned into. The other women were enjoying my show. In fact, I suspected that they were turned on. Kara looked particularly flushed.
Next, I serviced Hector's buddy Jose. This time I pumped his big shaft as I sucked on the head and tickled his balls. When it was apparent he was ready to cum, I stuck my tongue out and said with a lisp: "Feed me your spunk, you big stud." This caused the room to erupt into hysterics. I didn't like to humiliate myself like this, but at this point I would do ANYTHING to please my superiors and help ensure I didn't get spanked again any time soon.
"Make sure you don't spill a drop on my carpet," said Carissa, or I'll turn Gina loose on you with the hairbrush." I swear that intelligent young woman could read my mind. With that, I made certain to hold my mouth perfectly steady as Jose pumped his creamy sperm safely into the back of my throat.
After cleaning him off thoroughly, Carissa ordered me to get on all fours in the middle of the room.
"Who wants to see him take it in the ass?" she asked.
All the women immediately raised their hands and said, "meeee!"
Amy seemed to brighten. She made me beg for it, but she was once again disappointed since I enjoyed getting my ass pounded. It stimulated my prostate gland and gave me a combination of pleasure and pain as my penis leaked cum and strained against my chastity tube.
Over the next half hour, Jose and Hector took turns fucking my ass and mouth. Carissa made sure they both shot their loads into my hungry mouth and once that was finished I was ordered to clean my anal juices thoroughly off their cocks.
“Who’s the fucking cunt now?” said Kara, as she exchanged gleeful high fives with the other ladies.
“Urghhh, I am,” I said through the penis that was stuffed in my mouth.
By the end of the day, my ass was so incredibly sore - both from the pounding it had taken and the lesson in respect Gina had administered in the morning. I felt so used and was having trouble walking. Amy gave me the once-over late in the day when I was about to leave, and for the first time since the morning, she seemed pleased with my state.
I kneeled in front of her and recited the line I was always required to recite: "Boss, I hope I was a faithful lackey for you today. Can I have your permission to go home?"
Amy sat back in my former chair and crossed her legs. She looked quite satisfied as she gave me the once over. "Just look at what we've done to you," she said. "And to think, you love being treated this way. Yes, you're dismissed. I'll call Lydia if I feel there are any behavioral issues that need to be addressed."
She turned away from me. I knew I had to kiss her feet as a sign of respect before I departed, but as I assumed the groveling position, she kicked me lightly in my chin and said, "Get out of my sight, you dirty whore."
I thanked her and left.
___________________
When I staggered into the front door that night, I was initially relieved. I looked forward to a hot shower and a chance to clean off my face and my sore asshole. I figured I'd just stay out of Lydia's way and could have some time alone to wallow in my sorrows that evening.
Right when I entered the front door I heard the shrieking coming from upstairs. At first I thought Lydia might be in trouble, but then I realized the sounds I heard were groans of pleasure, not panic or pain. As I went up the stairs, the sounds became even clearer. "YES! YESS! YESSSSSS!!" Followed by, "Oh god, yeah, Fuck me harder, Harder, HARDER!! YESSSS!"
I realized it was Lydia and my heart dropped. Opening the door to the bedroom, I was stunned to see my wife lying on the bed. Her legs were high in the air. She still had her high heels on, but that was the only thing she was wearing. Her beautiful tits were bouncing back and forth as a large man absolutely pounded her pussy with his big stiff rod. Looking closer, I was even more stunned to see that it was a junior salesperson from my company, Keith Williams. He was pumping my wife like a diesel engine. His balls smacked against the underside of my Lydia's ass, as she squealed in ecstasy.
"Keith!" I said, "What the hell?!"
Keith looked up and to my surprise he began laughing. Then I realized I was standing there in my sissy slut outfit. My hair was a mess and makeup was all over my face.
Then I heard my wife: "Charlie, get the FUCK out of my room, you sissy bitch, before I throw away your chastity key and blister your ass!"
I immediately went to leave and on my way out, I heard my wife's wanton voice again. "Stand by the door so you can hear the sound of a real man making love to your wife."
I stood by the door and listened as Keith fucked my wife for another 15 minutes. The guy must have had some amazing stamina. My wife had at least five orgasms. I had never heard her make sounds like that in my life. Keith was enjoying it as well. He groaned and said, "That’s it, beautiful. Your pussy feels so fucking juicy. That's it, purr like a hot bitch in heat. Who's your daddy?"
"You are!" she moaned. "You arrrrrrrrrrre!" And again she was overtaken by a powerful orgasm. I felt the shame come over me again, but I was also immensely turned on.
Finally after what seemed like forever, I heard Keith say, "I'm gonna cum! I'm gonna cum!"
"Shoot it deep inside me, you big stud," moaned Lydia.
Keith began groaning and then I could tell he had a powerful orgasm. Finally they calmed down. I heard them whispering amongst each other as I stood there like an idiot.
Then I heard my wife: "Charlie, come in here. NOW!"
I opened the door and kneeled by my wife. Keith was getting dressed.
She ignored me. "Keith-stud, you want this sissy whore to clean off your big, thick cock?"
"No, that's ok. Gotta run," he said. He came over and while I kneeled there, he grabbed my wife like a rag doll and French-kissed her deeply. He gave one of her tits a good grope and they said their goodbyes. Lydia's face was flushed with a happiness I had never seen before.
As he departed, she turned to me and said, "Now that's a man!"
For some reason, it hurt my feelings. I could feel the tears well up in my eyes.
Lydia laughed out loud. "Oh come now, Chuck, don't make me have to use the hairbrush."
I immediately composed myself. Lydia ordered me to look at her.
"Look, Chuck, it's OBVIOUS you aren't going to be fucking me anymore -Thank god," she added. "I need a real man to satisfy me. Keith has a real-man's cock and he knows how to use it. He gives me deep vaginal orgasms, something you never ever could do."
She paused to let it all sink in, while I hung my head in shame.
"What did you expect to happen, dummy?" she said. "I have needs that you can't meet. I need a real man to satisfy my cunt - not a feminized sissy. But there's something you can do." She pointed to her ravaged pussy.
"Get down there and clean it up nice and good."
I hesitated.
"C'mon, you fool. You should be used to it with all the man chowder you've been guzzling. Now, don't make me tell you again. Clean Keith’s paste out of hot cunt this instant."
I stuck my head between my wife's thighs. Her pussy had been stretched by Keith. It was partially open, and fully engorged from its recent strenuous activity. Her dark pubes were soaked, and the odor was quite strong. An amazing amount of cum had pooled on the bed below her snatch, but a healthy amount continued to ooze from her gash.
"Clean the bed with your tongue as well," she said. "If I don't sense that you are putting proper effort into it, I'll up your chastity by a month," she said, dangling the key in front of me. "And I'll let Gina know, so she can take care of you tomorrow morning, if you get my drift."
With that I lapped up the fluid on the bed and thrust my tongue deep into Lydia's sated vagina. I began ingesting the gobs of hot cum recently deposited by Keith. Eventually Lydia had an orgasm and for a moment I felt proud.
"Ahh, it feels so good to be able to have multiple orgasms whenever I want. Of course, you wouldn't know anything about that, would you?"
"No, ma'am."
"I knew we could find some use for you," she said with a deep sigh of satisfaction. "Now get out. I'm through with you for the time being."
Epilogue
I’m pulling my panties up over my ass and now I’m admiring myself in the mirror. The hormone treatments or "whoremone" treatments prescribed to me by Carissa and Amy are beginning to pay off. I’m looking more and more feminine every day. I’m very excited for the day ahead. Carissa has found a couple of big gay guys at the gym who want to fill me up. It’s been almost three days since I last took hard cock in the ass. If it was up to me, I’d take big, thick cocks in every orifice five times a day, but my female superiors insist upon regulating this, and all other aspects of my life. No cock without their consent. As it so happens, I’m no longer required in the office unless there’s cock that needs to be serviced. I spend most days cleaning the ladies homes for which I’m paid a small stipend. It’s just enough to cover my bare necessities.
I can feel my anus buzz with excitement as I apply my lipstick. I’m also salivating at how it will feel to have my lips wrapped around their thick cocks and how delicious their salty loads will taste. It’s especially exciting because Carissa and Amy will be back in the office to witness me “in action” (they missed my last gang-bang). Kara will be supervising the event – She seems to take great joy in humiliating me in this fashion. I don't think she ever got over the "stupid cunt" comment I had made back when I was a man. She's been making me eat those words - literally - ever since. She likes to make me actually chew on my cumloads before swallowing. I find this habit annoying since it delays my gratification. But she, Carissa, and Amy convinced me it was for the best because it gives them pleasure to see the look on my face while I eat semen. Oh, just the thought of all that delicious sperm sliding down my throat as the women point and laugh is making my micro-penis strain against my chastity belt. But there will be no release today, nor for another six weeks if, and only if, I perform satisfactory “work” between now and then.
I’m checking myself in the mirror one more time before I leave my apartment. Lydia kicked me out a month ago, deciding she didn't want me around unless she needs me. Now I live in a cheap apartment a mile away from my old house. I suppose I could feel bad that Lydia, Carissa, Anna, Amy and the rest of the ladies that rule my world all live in nice big houses and drive big, luxury cars, but what’s the point? They’re my superiors and it’s my true calling to serve them in any way I can.
Now I’m smacking my lips once in the mirror. And now I’m sticking my ass out. I look great! As I stick my ass out, I feel the nylon of my cheap miniskirt rub against my naked cheeks and it hurts. Gina spanked me savagely two days ago when I was five minutes late with lunch. I’m giving myself one last look before I walk confidently and happily toward my little used Hyundai.
THE END
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