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Intro to Femdom
The Beginning
It was normal day on the road. I was working out of the Los Angles office for couple weeks and I decided I needed to get away from the local staff. There was a local Mexican restaurant in the neighborhood which was nothing fancy but the food was good, it was one of those places you order at the counter and wait for your food. I headed there for lunch planning on getting a couple of enchiladas with all of the fixings and then taking it back to the office and eating at my desk.
I was standing in line behind a very attractive woman. She looked to be in her 40’s with a body that was very pleasing to look at. The line was moving slowly. She turned to me and commented about how difficult was it to make a taco. I smiled and agreed that it seemed to be taking a long time. Taking the lead, I told her a few of silly jokes about waiting in line and other slow situations. She smiled and laughed at them all.
Changing my mind about going back to the office, I took one the seats at the counter along the wall. I took the middle seat of 3 empty seats hoping she would take the unspoken invitation to take one of the seats next to me. I smiled when she did and we settled into a casual conversation. As we finished, I offered to take her for real Mexican food for dinner at one of my favorite restaurants in Orange County. She placed her hand on my left hand touching my wedding ring. I looked down and then back up to her eyes. She smiled coyly and asked if there was any reason at home with this would be an issue. I replied with no and I live 1500 miles a way I was in town for a couple weeks on business and that I normally came to LA one week a month. Not quite answering her question but looking at her in a way that said there wouldn’t be an issue.
She smiled and said she would love to have dinner. She told me her name was Cindy and told she would meet me at 7:00pm.We parted and I went back to the office. I was a little unfocused for the rest of the afternoon thinking of Cindy and the things I would like to do to her.
I was a little surprised that Cindy accepted my offer. Cindy is an attractive woman about 5’10” with 3” heels on makes her well over 6 feet tall. She has a nice figure with curves in the right places. She has medium length light brown hair which is worn straight with bangs. Her green eye set off her classic “U” shaped face. All though I’m in good shape physically, I’m a man in my early 50’s with a little gray hair and a few too many miles on my face. I’m sure that the fact that I’m 6’3” did help some.
We met that evening for a lovely meal at the Mexican Restaurant near my hotel. She had dressed in a red sun dress and heels. She looked so damn good that I wasn’t sure we would make it through dinner. During dinner, we became very chummy. It was surprising how easy she was to talk to. As I think back on it, she took the lead in much of the conversation.
During the meal our hands lingered as they touched on several occasions I felt that if I asked I had a chance for things to go further. On several occasions during dinner the conversation had drifted towards sexual subjects and she did seem to be flirting back to me. I was surprised when she asked where I was staying while I was here. I told her the name of the hotel and the location. She laughed and said that was pretty confident. I said yes and told her that I had walked to the restaurant in case we did too much drinking. She asked how many drinks it was going to take before I invited her back to my hotel. I said we were there and I asked her over for another drink at the hotel.
We walked to Cindy’s car and got in. We drove to the hotel, parked and exited. In my mind, I was already planning ways to please her and imagining how she would please me.
Cindy was quite a surprise once we got to my room. She started kissing within seconds of entering the room. I started to reach for her breast but she deflected my hand and instead she started unbuttoning my shirt. We kissed and she rubbed my chest and nipples. I tried to reach for her breasts again and she slapped my hands away. We continued to hug and kiss, exploring each other’s mouths. Suddenly, I felt her hand at my belt and zipper. Within minutes she had my pants, shorts, socks and shoes off. Her hands and mouth were covering every part of my body. It did feel strange naked in a room with a woman who was fully clothed.
We moved to the bed. I lay back on the pillows as she shifted so she was straddling me. I could feel the silkiness of the thighs on mine as she rubbed her panties on me.
After about 20 minute of very hard necking Cindy unbuttoned a few buttons on her blouse and exposed a near perfect left breast. She positioned the breast in front of my eager mouth. I started to lick and suck her nipple causing it to harden. I heard her gasp.. She pulled her breast away and told me how she liked she breast sucked. I was only too happy to indulge her. I sucked and licked for the longest time. Much too soon, she put her breast away and took out the other. I worked on it for several more minutes. The whole time she was sitting on my erection. Every time I make a move to remove her clothing or get inside her panties she stopped me.
She put her breasts away again and I began to wonder if the evening was over. But just as I started to say something, I felt her hand on my erection. She turned around and put her crouch over my face. I could smell her sex and feel the wetness in her crotch through here panties. She lowered her dripping pussy to my mouth and I felt her fingers move her panties to one side. As with her breast she took some time to explain in detail how she like to be licked. She would alternate between me sucking her pussy and her playing with my cock and balls.
Then she raised her pussy up form my face and took her fingers and buried them in dripping pussy for me to watch. I though I was going to cum on the spot. She looked back at me over her shoulder. She told me she was going to milk my cock. She then took her wet finger and traced my cock and balls. I could feel her warm breath on my cock. Just as her mouth touched my cock I felt her warm slippery finger entering my ass angling straight for my prostate gland. I could feel her finger pushing the cum out of my prostate gland. Every few second she would suck the cum out of my cock. She said don’t cum that she would tell you when. For the next 20 or 30 minutes she kept me hard without letting me cum. The whole time she was pushing cum out of my prostate. Every few minutes she would lower her pussy on to my waiting lips.
She turned around and sat back down on my erection. She moved her panties to one side and swallowed my cock on one push. It was heavenly. She slowly pumped my cock for the longest time I was amazed I wasn’t shooting cum everywhere. I would see and feel the orgasms rolling thru her body. The more she pumped the harder and longer she came. After 30 minutes she was done.
My first thought was I didn’t cum but then I did feel satisfied. My cock was getting soft and I didn’t feel like I still needed to cum.
Cindy rose up and was standing at the end of the bed looking wonderful and still fully dressed. She asked if I felt good and I responded with yes. She smiled. I said I didn’t think I needed to ask her. She said “no I didn’t”. She asked if I would like to come over to her house Friday night for dinner and other things. I immediately agreed. She wrote her number on the pad of paper on the desk. Gave a quick finger wave and left, I was so sated that I fell asleep within minutes.
Cindy was all I thought about for the next 2 days.
I got to her house at 7 pm. The house was a nice Spanish style house with a private front courtyard with lots of arches and tile roof. It was typical for the LA area I rang the bell and the door opened as I stepped through the front door I noticed there were shoes by it so I removed mine. Cindy was wearing a very sexy, low cut black dress with fishnet hose. We went straight the dinning room. She told me she just needed a couple minutes to finish up dinner.
It was a wonderful meal. We flirted all during dinner. After dinner I got up to help with the dishes. As we were finishing up Cindy came over and started kissing me in the kitchen.
She asked if I would like to watch a couple adult videos, I easily agreed. Much to my surprise Cindy’s video taste were Femdom movies. In the first movie, a busty woman had a houseboy who she always kept nude. The houseboy serviced all her sexual needs. I wondered where I had seen that before. In the second movie, the woman wearing very sexy black leather had a slave with a collar who took care of her and her friends. The slave wore leather and assortment of cock and ball leather straps.
At the end of the movies Cindy asked very nicely if I wanted to stay for the weekend. I responded that I assumed we watched the movies for a reason before she asked the question. She said yes and so did I. I thought I should try everything at least once and I in fact I had a wonderful time Wednesday night.
Cindy said I could store my clothes in the closet by the front door. I felt very naked when I returned to the room with a fully clothed woman waiting for my return. We had a surprising very quiet evening. I’m not sure what I had expected to happen, I spent evening kissing, rubbing, licking and sucking all of Cindy’s body. It was wonderful. I never once had to decide what do next as Cindy told me what she wanted and how she wanted me to do it. I brought her to several orgasms during the evening.
She set a couple of basic ground rules for the rest of the weekend. First one was that she would make all of the sexual decisions. Who touched what and when. I wasn’t to touch myself without her instructions. I wasn’t to cum without her permission. I wasn’t to wear clothes inside her home.
It was kind of liberating not wearing clothing all day.
As bedtime approached I wondered when it would be my turn. I didn’t have long to wait. Cindy had me get on the coffee table on my knees and elbows. I felt her warm wet finger enter my ass and within seconds I could feel the cum dripping out of penis as she rubbed in tight little circle. The cum continued to flow for 10 minutes into the bottom of the small bowl she had placed under my dick. Just as I had felt the first time, I had the warm after glow of an orgasm but no orgasm. I wasn’t sure how this milking worked but it worked.
Then my surprise for the day came. Cindy told me to wait on the table she returned a few minutes later in a bra and panties with large strap-on penis. The strap-on protruded from her crotch like it was real. I knew what she had planned of the rest of the evening, she walked to the front of the table and had me lick and suck her crotch and strap-on. I gave it a blowjob and she fucked my face with it. After she grew tired of the games she moved behind me. I could feel the head run up and down my butt crack then it circle my virgin anus. She slowly worked the head into me. She then started pumping me with little short strokes. She took her hands and started pulling my body in time with her strokes. I knew she wanted me to meet her thrust with a push of my own. With in minutes I could feel her hips as they met my butt. The dildo was fully in my anus. I would no longer be able to think of it as a virgin. I could feel her body beginning to orgasm. She had a long powerful orgasm. Then she went limp behind me. After a short rest I could feel the dildo sliding out of my ass. She petted my head and said I could go to bed now.
I wasn’t sure where I was sleeping that night. She had made up the guest room for me and showed me the basics of the house. As I turned to enter the room, she rubbed my butt cheek and then gave me a little slap. I heard her laughter drift down the hall. I laid down replaying what had happened early. I felt my cock getting harder and was tempted to stroke myself. I remembered that it was against one of her rules so I restrained the urges and eventually fell asleep. After all if we were playing the game I should play by the rules.
I awoke the next morning to find a note on the bed table with instruction for the morning. Seems Cindy was an early riser and was out of the house. When she returned at 10am I had breakfast ready and all of the chores from the note completed.
After we ate, I was called the bathroom. She pointed at the toilet seat which was in the up position. She explained that it was always to be down. I told her it wouldn’t happen again. She told me to put my head on the bathroom counter looking at the seat and rise on to my toes. I watched as she picked up a hairbrush from the counter. I didn’t know how much it would hurt and burn when the backside of the brush met my backside. After 5 firm blows to my butt I was reminded that the toilet seat would always be down from now on.
Cindy told me to stand up and face her. She then kissed me and told me she had presents for me in the living room. I was amazed at how fast she could change from punisher to loving friend. I walked my sore butt into the other room where Cindy sat with a brand new leather V shaped cock and ball separator. It had a ½” wide scrotum straps the force my balls way in front of my body. There are 2 leather straps that go between the testicles forcing them apart. I will say when she first put in on me it looked amazing. My testicles were sticking a couple inches in front of my body and a couple inches apart. The scrotum strap made my cock seem shorter but even soft it was sticking straight up. Then came the reality of walking around with your balls leading the way, they would bump into everything. Every action I took during the day I needed to see how it would affect the testicles. I was sure Cindy liked them that way because they were easily reached and viewed.
There were 3 other straps for other occasions. There was a basic strap made from ½ wide leather straps a cock ring with two extra straps which harness and separate the balls. One of the straps goes around the balls in front and the other runs between the two to separate them. There is a leather harness consisting of two leather cock rings, one to be worn behind the balls and the other at the base of the cock with a “D” ring on top for a leash. The 4th cock and ball harness consists of a black leather cock ring with 3 nickel-plated adjustment snaps that is connected to a 1½" steel O-ring by two leather bands. The bottom band serves as a ball divider and has 2 snaps, while the top one connects the two rings and has one snap.
Saturday afternoon was a pretty normal day we watched a baseball game on TV had lunch. I did spend some time between her thighs but not much. She would have me run silly errands around the house I’m sure was so she could watch how I was adjusted to cock and ball separator. If I lay down on my stomach it required two pillows to keep from crushing my balls. Of course my ass must be sticking a foot up in the air.
After the game Cindy decides we are going for a walk. I was little taken back. I hoped she didn’t expect to go outside nude. She returned with a pair dark blue gym shorts and light blue t-shirt and my tennis shoes. With the ball separator the front of the shorts are very full. Just as we got to the front door Cindy stopped me and said she may want to use my ass again tonight and it was a little tight last night. She told me to drop the shorts and bend over. I was fitted with shiny new butt plug to loosen me up a little. She reminded me to not let it slip out on our walk. I couldn’t imagine the embarrassment if it fell out walking. Well it was interesting experience walking with a butt plug. I felt it move inside with every step. We took a nice 1 ½ mile walk around the small neighborhood lake. We didn’t run across to many people and when we did we just kept walking.
When we returned to the house I made a big error. I just walked inside the house in my blues shorts. Cindy snapped around when she heard me walking. She demanded to know where I was going dressed like that. I knew I had made a mistake. I quickly pulled the clothes off. She sternly told me to wait in the hall. She walked in the bedroom between the master bedroom and the guest room and a couple minutes later she opened the door an invited me in. She said she had hoped I could have gotten a couple more days to know her before she needed to bring me here. There was a big wood “X” in one corner, a couple of wooden saw horses in the other and an assortment of whips, paddles and canes on one rack. The other had hand cuffs, leather straps, blindfolds and several thing I couldn’t figure out.
I stood at the door for a long time before I entered the room. Did I really want to go down this road? She said I should come in and talk for a few minutes. We sat on two leather pillows in one of the corners. She explained why she liked the Femdom lifestyle as well as all of the reasons she thought I would enjoy it also. We talked about safe words and trust, giving and holding the power. After about 45 minute I told Miss Cindy I was sorry I had broken the rules. I asked for her to help me to remember not to do it again and I was ready to atone for my behavior. I mean it couldn’t be much worst then the hair brush could it?
It was about 3 days before the red cane marks disappeared from my butt. Miss Cindy walked me over the padded sawhorses. She bent me over the horse, took my balls and clamped a long wooden tool on both sides. This in effect prevented me from straitening up. When I jumped from the caning it pulled hard on my balls. She told me she was going to administer10 strokes and that if I didn’t take them as she desired, she would start over. I so wanted to scrim between each hit but that was worse than just standing still. The next 10 minutes were hell. The bamboo cane bit the skin on my ass with each stroke. The narrow cane wrapped around the curve of the ass as it struck. I felt each welt forming before the cane is removed. The sting lasted for hours. There was no question in my mind I wouldn’t make that mistake again.
It was amazing how loving Cindy was Saturday night. She was careful not to touch the fresh red welts on my butt. She didn’t make me bend or sit on them. She treated me like a hurt little boy. She did look at them every time I walked across the room. Near bed time Cindy called me to living room she was sitting next to the coffee table with milking bowl setting on the table. I assumed I was about to get milked. Much to my surprise she unsnapped the cock and ball separator and gently kissed my penis until it was nice and hard. She alternated between sucking and stoking my penis by hand. With in a few minutes I was filling the bowl with globs of cum. I still to this day think it hurt her as much as it did me when she chooses to punish me. Saturday night I slept face down on the bed.
Sunday morning was the day my life changed forever. Cindy woke me with a gentle kiss on my tender ass. We talked for hours about her role and my role in our Femdom relationship. Her hands were tender as she tended my bruised red ass. She said that most submissive men are loving and caring, and want to please she felt that I was that way. Deep down they want to know that someone to accept who they are, and their gift of submission. She told me how much she wanted me to fill that role in her life. She asked me if I was willing to be trained as her personal slave. To be that someone who took care of her personal needs. I decided I was willing to be trained as her personal slave; I would give her full control of us. I would devote myself to making her happy. Her joy would be my joy. Her fulfillment would be my fulfillment. She wanted me to know that she enjoyed being my mistress. In simple terms, she would truly enjoy 'owning' me, and truly enjoy the authority she would have over me. The first new rule being nude in her home now started on the other side of the front door.
We started the day checking me out of my hotel for the rest of the week I would be staying a Cindy from now on when I was in town.
The Closet
A few months have pasted and my involvement with Cindy has matured. I’ve change my travel to schedule to make sure my monthly visits to the office always include a weekend in LA. Plus I’ve tried to get there a little more often.
Our roles have become more defined. Mine is somewhat that of a traditional slave and submissive. I have chosen to surrender and be obedient to her. Why, the mental freedom it gives me. I know once I step through her front door I will no longer require to make any decisions. I don’t have to plan the next step. I don’t have to out guess what will make her happy, she will tell me. But in some way I do expect some gratification in return for my submission. I recognize that I have chosen to give Cindy the psychological power over our relationship. The relationship does seem to have some of the mutual respect and support that many vanilla relationship have. She is always there when I need to just talk thru something and I’m good listener when she needs emotional support.
Cindy role as the dominate partner, makes her in charge of most aspect of our relationship. She does the planning, controls the schedules, sets the rules and if needed the punishment for not following them. Our relationship is by no means sado-masochistic but she does enjoy some physical parts of BDSM. We have agreed on some limits, which she has respected. Much to my surprise she hasn’t asked me to help pay for any of expenses when we are together. There is no expectation that either of us is monogamous. In fact sometime she will leave on a Friday or Saturday night for a date and doesn’t always return before morning. And I am not there 3 weeks a month.
She does like to push the limits of my submission. One night we talked about my being the closet was hurting her relationship with her friends. We agreed to work on that sometime. The next Friday night I walked in the courtyard and began removing my clothes I noticed a note on the door which told me to ring the bell someone would open the door for me. Standing there nude waiting for the door was a little disconcerting. When the door opened there was woman had I had never seen before standing in the door way. She said “you must be Cindy’s boy toy” come on in. I followed her to the kitchen were Cindy sat with 3 more women. I wasn’t introduced to them but they where all told who I was. Cindy as she did every day put one of my cock and ball separators. For the next 45 minutes to and hour I served drinks, dinner to the group. Most of the women talked about me as if I wasn’t there. A couple asked me questions which Cindy answered. At some point someone said something and my reactions was an erection. Cindy snapped the end of my penis with her finger nail and said my friends did come here to see that. I was instructed to go wait on the milking table. I did.
Cindy cuffed my hands behind my back as I knelt on the table my butt sticking high in the air my chin hanging over the front of the table. I heard Cindy put on a rubber glove, that met I was going to get a quick milking nothing loving or tender for me. With in seconds the lube finger was circle my prostate and I could feel the cum dripping into the mirrored bowl she use to milk me in. Several of the women asked her questions. She explain how milking worked and how to do it. One of the women asked to try it. I felt several strange fingers rubbing my prostate.
When the milking was over we returned to the kitchen were I severed more drink and desert. Of course it was much hard with my hands cuff behind my back. I could tell Cindy was happy with my performance in front of her friends. I was obedient and very respectful of them all.
After they left Miss Cindy said I could leave clean up until morning, she took my arm and then walked me down the hall but we didn’t stop at my room or the playroom she took me to her room. I had only been in her room once before. Normally when we played it was in the playroom or my room. Cindy guided me on to the bed. I was lying on by back with my hand still cuffed behind my back. Cindy left for the bathroom, a couple minutes later she returned. Her breast were both bare, she had on a good sized strap-on and nothing else. It was the closest I had every seen her to nude before outside the bath tub. She strolled up the bed the strap-on swinging like an elephant’s trunk. She palace her breast for me to suckle, she had me lick and suck her pussy and the strap-on. The much to my surprise she removed my cock and ball separator. I could feel my erection raising. For quite sometime she would move between my legs placing her breasts for me to suckle, then giving me her pussy to service and rubbing my erect penis as she changed positions. Then she started to rub lube in my ass, which was a job that was almost always done by me. Her fingers moved between stroking my penis to exploring the enter depth of my ass. She started tracing the outlines of my penis, by scrotum and run the head to strap-on up and down the crack of my ass. She moved the head of strap-on to line up with my ass and started to push in. I was shocked; I have had the strap-on used on dozens of times but never when I could see her it was always done doggie style.
Miss Cindy was a vision of power and sexiness as she worked my ass with the strap-on. I could see her breast raise and fall as she push in and pulled out. She placed her hands on my hips to direct me to push to meet her thrusts. Then every few strokes she would wrap her hand a round my penis so my hip strokes would push my penis between her fingers. The pressure of strap-on against my prostate and warm of her fingers was getting to me. I asked Miss Cindy for permission to cum she told me to wait. For what seem like an hour I struggled to control my orgasm. Finely I felt her start to orgasm. What a heavenly sight. The glow on her face, the heaving of her breast and quivering of her hips and legs, then I heard her tell me I could cum, she direct the cum on to my chest and stomach. I shot 3 or 4 big squirts of cum. Miss Cindy rubbed it from my chest hair to my testicles. She slump onto my chest her breathing was fast and I could feel her heart bounding. With in a few minutes I could feel the strap-on sliding out of my ass. Miss Cindy rolled me over and turned down the bed she then rolled me to the other side of the bed. She snuggled up behind me putting her arm over my shoulder. Like a mother bear might do to protect her young or maybe just to show me I was hers.
After that day I wasn’t sent to my room when Miss Cindy’s friend came for a visit. It make thing much easier. I adjusted pretty easily to being there nude when her female friends visit. I did have a little more trouble when her male friends came by. I never did like being their when other men came to take her out. I never quite knew what they were told about me. But I didn’t have to interact with them so it all seemed to work out.
One 3 day holiday weekend Miss Cindy told me we were going to party at some friend of hers on Saturday night. I mistaking asked if they knew anything about our relationship. She smiled and said of course. Mid-afternoon on Saturday Miss Cindy started getting us ready for the party we when to barber shop and hair saloon. I got the pleasure of a Brazilian wax. I’m a somewhat hair guy and with was the first time I had my crotch hair removed. I was an interesting feeling the guys did look a little naked down there. It made my balls look huge.
When we returned home, Miss Cindy took me in the bathroom and setup my enema kits. Although Miss Cindy required that I have an enema almost every day, after the first couple that she supervised I normally did them myself. Miss Cindy laid me in the tub and inserted the nozzle in my anus. Every 4 or 5 minutes she had me turn to my other side. I don’t know how much water she ran into me but my belly was extended when she was done. I had to wait 20 minute before I could empty my colon out. I took several tries to get it completely empty. She shower and primed me for over and hour. About 7 pm we loaded into her mini van me in the middle of the middle seat dressed in my finest cock and ball separator and a brand new shinny slave collar. When we arrived at the house hosting the party I notice several cars park in driveway. The driveway was relative well screen but not completely out of view of the road. As the Miss Cindy opened the side door she added a ball gag and blindfold to my outfit. As I step on to driveway I could feel her clipping a leash on to the collar. I walked slowing into the house. I could hear and sense several other people in the room. I was walked to a spot were Miss Cindy pulled my leash until I dropped to my knees. Someone cuffed my hands behind my back and cuff my ankle I could feel the chain connecting the two pair of cuffs. I was sure there wasn’t enough chain for me to stand.
There was someone kneeling on my left it appeared to be a woman as she was much smaller and softer than a man would be. A few minutes later someone else knelt on my right. I was pretty sure it was a man. I could hear the cuffs being attached. Time is very hard to judge when you’re blindfolded. I was aware of people walking by some stood and watch those in the line. Some talked about us. A few just stood there and breathed out loud. From the number of stops and commits people made I guess there were six or seven of us in the line. I was near the left end.
A couple times during the early part of the evening Miss Cindy would bring me a drink of water. During the early part of the evening guest would stop by and add toys to the people in the line someone add nipple clamps to me. A little later someone added weights to the chain between the clamps. At one point I feel someone adding weight and cloth pins to my testacies. Miss Cindy would come by often and check on me. Some times she just committed on what was added sometimes she would move it.
Later in the evening I could hear the party moving into the area we were kneeling. A man with a strong voice seem to me in charge, Miss Cindy was standing behind me with her hands on my shoulders. The man explained we were going to have oral sex contest. The 3 lowest scores would be sent to dungeon. She removed the ball gag I could feel people moving closer. Then I felt a pussy move up to my lips I wasn’t sure what would happen to the rest of us but I had no interesting going to the dungeon. I started liking and sucking for all I was worth. After a couple minute the judges were told to move. The next judge had external plumbing; I had done many blow jobs on Miss Cindy strap-on I had never had a real cock in my mouth. It was actual much easy to suck on, softer, more flexible, no hard plastic taste and it had character with thing like a head. I wasn’t sure how well I had done but I was happy when the judge moved on. There were 4 female judges and 3 male judges; I did manage to get one woman judge to orgasm during my time with her. I’m not sure how I scored but during TV game show style selecting I didn’t get walked back and forth between staying and going to the dungeon groups.
The next major event for me that evening was Miss Cindy talking about prostate milking with a group of people. It doesn’t that a rocket scientist to know I was doing to get milked for the crowd. But I will say having several people’s fingers up my ass was a lot better than the noises coming from down the hall. I could tell the hands doing the milking were much more experience than Miss Cindy’s group of friend from a couple weeks ago. They were not hesitant entering my rectum them move to round quickly. I will say it didn’t take them long to drain me dry.
Miss Cindy brought one of her friends over for near the end of the evening I spend some time licking her to a couple of orgasms. It was interesting lick and sucking the whole time she and Miss Cindy were talking about sometime going on in the dungeon to the woman I was sucking slave. It was nice to know she could understand why her girl was in there and not me.
On the way home Miss Cindy told me she thought I was enough out of the closet that it wouldn’t affect her social life anymore. To my surprise on the rare occasions we had a BDSM evening out not much really happen. Play was generally pretty limited. But Miss Cindy did always enjoy the evening out.
The Other Men
Miss Cindy and I never had an exclusive arrangement. From the very beginning she dated other men. I don’t know it the relationships were vanilla or Femdom. I always assumed there was some of each. The fact is it doesn’t really matter. We have what we have when we have it. There was never any talk of the relationship being more than it was. Just as she did with bring me out of the closet one day she decided she needed for me to be more present when she dated. It was hard to bring dates home when I was there. She told me a few days in advance that weekend she had a date I was going to met. We discussed some limits. I wasn’t expected to have sex with them. But she did expect me support their sexual effort with her when needed. I was told I would have some clean up duties. I should expect some warm up duties for both parties.
The first night Miss Cindy had a stay over date when I was there was a little hard to explain. When Miss Cindy and her date arrived from at the house from dinner I don’t thing he was prepare for seeing a nude man in the house. The guy wasn’t really sure what to make of me. Miss Cindy told him I was there to help if needed. I really sure he didn’t have any idea what that met. I know he was expecting me because he knew was to call me and knew he should ask Miss Cindy to request anything he wanted from me. I server a couple rounds of drink. They started making out heavily on the couch. I waited behind them out of line of sight by the kitchen door. I wonder what the etiquette was for my position should I be watching or turned the other way. I must say it was some what exciting watching a live sex show. I stood there quietly has he worked at removing her clothing. I remember my first effort at that. Will say she did get him naked long before she was there. I watched as she guide him between her legs even for my vantage point I could tell he wasn’t doing thinks the way she liked. She tried moving his head the way she wanted but she meet with little success.
I heard her call for me and signal for me to move between her thighs. She pulled him up to her breasts and mouth. I did several minutes of licking a sucking. In the back my mind I wanted to get her to cum and ruin his evening. But alas she stopped me for I could get her there. With in a few second he was trying to mount her. She used her hand to stop me from leaving. So I knelt next to them as he humped away. I could tell she wasn’t done we he finished. I knew I was going to get a taste of male cum very soon. She directed my head between her legs. It only took me a few minute to bring her off. She then dismissed me to the kitchen door way. I stood in the door way with my crotch throbbing. I watched as he tried to get seconds. I could tell it wasn’t happening.
The next morning at breakfast Miss Cindy told me we had another guest that evening. The evening started much the same. This guy wasn’t nearly as surprised. They started on the couch with wine and cheese. This one did was much better at getting Miss Cindy’s clothes off. But he still was nude first. And OH my, when I saw him nude with a good 9 to 10 inch cock. I had never seen anything like that in real life. It swung around like a sword. In the middle of their heavy petting he asked me to stand were he could see me. Miss Cindy had me move to the other side of the room. I will say the view was much better in front of the couch. From this side his cock looked as big as Miss Cindy forearm. Miss Cindy made several jesters to have him go down on her. He deviously said isn’t that what he’s here for. Miss Cindy motioned from me to come over; her legs were spread wide when I got there. I did my part, I got Miss Cindy very wet and worked up. Then her new friend asked when was he got his turn? Miss Cindy grabbed his cock in one hand and pushed my head toward it with the other hand. I worked on his cock for the next few minutes. I don’t think, I every got more than the head in my mouth. For some reason I did think about making him cum to mess up Miss Cindy’s day. I do think our male guest was very surprise when Miss Cindy mounted him. And she did ride him hard. I could tell she was not happy with his performance. There wasn’t much clean up, I did take care of it for her only. Miss Cindy asked me to make sure he didn’t hang around. When I came back from showing him the door Miss Cindy was waiting in the playroom. We spent the next couple hours working out her frustrations. Seem Missy Cindy thinks most men with big cocks don’t know how to use them.
Day to Day Life
Day to day life can boring when you only see one person in the inside of one house. When Miss Cindy decided we needed to get the relationship out of the closet it opened up a whole new world. It gave us other people to interact with, now that Miss Cindy’s friend Staci and Beth know about me all kind of things change at the house. It’s not uncommon for one or both ladies to come over for dinner or just to visit. We even have had a few nights were we played Spades and Poker. I was the only one in the room who didn’t laugh when Beth say shall we play strip poker. Except for a few strange questions Beth and Staci seem to be taking our relationship in stride. Beth in always interest in what ever cock and ball separator Miss Cindy has me wearing on a given day. She always asked how they feel and what they do. Staci just seemed to like to have someone the run and fetch from the kitchen. For her that’s a little piece of heaven. I know both are marriage I never did meet a hubby for either. Other than Beth poking a finger at my restrained cock and balls I don’t recall either of Miss Cindy two friends being physically involved in anything we did. Miss Cindy never said much in front of me about our relationship to them. There were a few exceptions to that, mostly when I screwed up.
One afternoon when Beth was over for coffee I some how had gotten pretty involved in the conversation. I normally just answered questions and didn’t add much during girl talk. I told a joke that got big laughs from both women. Then Miss Cindy gave me the look and told me to go the play room. With minute I heard Miss Cindy coming down the hall. Beth was waiting in the kitchen. She entered the room, left the door open and told me to bend over the fucking horse in the center of the room. There was no question the door was open so Beth could hear what was going on. She removed my cock and ball device, I knew I was in for a busy afternoon. I could feel her attaching the Humiliator ball vice to my balls. It’s a long wooden board with a thick middle with a 1 ½ inch hole in the middle the board is cut in two halves. When in use the victims balls are stretched thru the hole the other side clamp the down it pulls their balls away from their body. In this since the vice was attached behind my leg my ball were pulled behind my ass. It is nearly impossible to stand; you can’t make any quick movements of your legs or upper body. It is an under statement to say it’s very controlling of movements and not at all comfortable. Miss Cindy then took her time telling that telling jokes about men being smarter than women wouldn’t happen again, I agreed with her of course. She then walked out of the room for a minute I could clear hear her and Beth in the hall talking. When she return she used a paddle and strap to make sure I remembered. I could her Beth gasp almost every time my ass received a stroke. I don’t know if she watched or just listened from the hall. Miss Cindy left me on the horse for a half hour. I could hear them talking like nothing happen. Later Miss Cindy came and got me to finish the afternoon chat. I was a lot quieter. Poor Beth couldn’t help to stare at my red ass and of course Miss Cindy had lots of running for me to do.
Our in general quite night at home involved me arriving at the house. Getting undressed in the courtyard, once inside there would be a cock and ball separator, note or Miss Cindy there with instructions. I cooked about 1/3 the dinners, Miss Cindy cooked a 1/3 or with went out for a 1/3. For dinner out I always wear a blue polo shirt and dark blue pants. Of course no underwear, yes to some kind of cock and ball device, about 50% of the time yes to some kind of butt plug or vibrator in my ass. I got good at following Miss Cindy so the bulge in my crotch didn’t look as big. When we return home I would general spent some time on the milking table. Sexual activity after that was always at Miss Cindy’s choice. Mostly Miss Cindy loves her oral sex.
One very nice spring night we when to Mexican Restaurant we first me at, I was a little surprised it’s not as nice as most of the places we would go to dinner. The one thing it had going for it was many of the eat stations were standup. Since Miss Cindy fitted cock and ball separator that had an attached butt plug and waist ban. I didn’t wear this device often and I was glad I didn’t the leather ball separator was very stiff and really pushed my ball forward, and the butt plug looked like the size of beer can not on did it stretched my rectum but the sphincter ring was very large stretching it to it’s maximum. I’m sure the waist ban is required to keep it from working its way out. The plugs size requires that I keep my feet a little farer apart, and shorten my stride when walking other wise the friction is unbearable. And there was a chance I would get to stand during dinner. Miss Cindy found a table with two very nice stools to sit down. I can’t recall a meal where Miss Cindy required so much service, I was up and down a dozen times for more forks, spoons, hot sauce, napkins, straw and more soda.
When we arrive home Miss Cindy had me go straight to the play room I could tell she was real worked up after watching me suffer thru dinner. She laid me on my back and attached a spreader bar between my knees. Normally the spreader bar is put between my feet, between the knee just forces my legs farther apart which actual helped the pressure the large butt plug was putting on my rectum. The bar was attached to a rope and pulled back over my head. My crotch and anus were very exposed. Miss Cindy slow removed the device from my crotch. I knew when she pulled the plug out my sphincter was doing to take a beating since the head was at least an inch bigger around the bottom shaft. And it did. I could feel the gaping hole that was once my anus. I could feel the air in room blowing inside me. Miss Cindy would easy put three and four fingers in the hole. She had talked about fisting before I wonder it today was the day I would learn more about it. I got my answer quickly as I felt them warmth of more lube being added to my rectum. I could feel the pressure as more of her hand moved in an out of my ass. Then it came the push as her thumb slipped passed my well stretched sphincter ring. It was almost a relief as I close down on the much thinner wrist area of her arm. I would hear the camera clicking to record the event. Then came the finally her hand balled into a fist. I felt full before but now it felt like I was going to burst. I could feel ever knuckle on her hand. She moved her hand in and out for several minutes with each push she went deep in by rectum. I raise my head as much as the rope pulling my legs back would let me there was white ejaculate dripping of my dick. Her arm looked like it was in me up to her elbow, I sure it wasn’t that far but I felt like there my insides were being push in to my stomach. After she took all the photos she needed I feel her hand relax and slid out of me. I felt like there was nothing holding my insides in. The hole where my anus was several inches in diameter and not closing very fast. To show me what it looked like she put the giant butt plug I wear to dinner, it just slipped easily into my ass now. Miss Cindy lowed my legs and but a couple towel on by ass. I laid there for an hour and the lube ran out of my ass and my anus returned to something like normal size. When I stood I was sure my inside would fall out I felt like nothing was holding me in. Miss Cindy was so proud I did it for her.
Some of the nights we stay at home we just hang around the house like any vanilla couple. We sit a round and talk about what is happening in our life and the world. We have differing political views. Other night we play Miss Cindy’s special BDSM games. Would it surprise you to learn the sub almost never wins at any of those games? Well expect the one where the prize in the sub licking the Dom pussy, I did manage to win that one often.
Miss Cindy had several games she loved to play, strip Black Jack was on of her favorites of course when you don’t start with any clothes you giving up sexual favors very quickly. She also likes a special version on kids game slap jack where the card pile in on my scrotum, so to win the pile I had to slap my testicles faster and harder than she did. It is amazing how slow your reaction time is when you smacking yourself in the balls. I did seem to lose this game often.
The Ending
Miss Cindy and I have been together for almost 5 years. Lots of things change over that length of time. Over the years other people have come and gone. Some guys hang a round, some guy just stay for a couple weeks. I can never tell what Miss Cindy is looking for in men. I she love the Femdom life but I don’t think she ever thought it was the answer to the rest of her life. The men who are more dominate didn’t seem to be willing to put up with her dominate side. I never meet and other sub men in her life but I always assumed there are others.
Then came the Saturday morning, Miss Cindy often enjoys a morning round with her strap-on. It is her way of getting the weekend days started. A bit of a morning warm up you can call it. If I not on my best behavior or she just wants something a little more interesting she will cuff me to the dinning room table. My wrists are cuff to the far side of the table and my feet are cuffed to the legs on my side. One day she seemed to want to make a point about something. I was cuffed to the table then Miss Cindy told me she was going shopping. She left me with instruction to tell her girl friends she would be back later. You feel a little more exposed bent over the table when you hear the door close and knowing company is coming. The 1st person to walk in was one of Miss Cindy’s none BDSM neighbors, we have meet several times before so she wasn’t real surprised to see me. She was carrying a several big green bag from the local farmers market. We chatted as she split the continents of the bags in 4 piles she told me who each piles was for.
Great more company was coming. One by one the local ladies pick up there stuff. Then in walked “The Marine” one of Miss Cindy boy friends I called him the “The Marine” he worn his hair in the military style, and frankly he acts like he was still in the service. He acted like an ass from the minute he walked in the house. He knew who I was and I knew who he was but we had only met in passing before. He was somewhat verbally abusive to me. He called me a few names, like pussy, wimp, and queer He was picking up CD’s and other items from the house. It seem to me he was picking up his stuff. He asked me several time were tuff was and acted the fool when I didn’t know the answers. I asked him if Miss Cindy knew he was there and he gave me a smart ass answer. I’m not sure what I thought I was going to do about I could only see in one direction and wasn’t very mobile.
“The Marine” took a couple boxes of stuff out to his car. He came back and gave me a message to give to Miss Cindy. The message had a lot of unkind commits and words about Miss Cindy. I told him he should tell her in person. He said “fuck you” to that commit. He started to leave but then turned around and said I’ll leave her a message you will give her. He walked behind me and I heard his zipper unzip, we yelled at each other I tried to fend him off with my ass. He reached down and grabbed my balls which were stretched out with a leather ball stretcher.
“Be nice pussy this is happening it’s just a matter of how much it’s going to hurt you.”The Marine said as he twisted my scrotum just to make sure I knew he was serious. I felt the head of hard dick pushing between my ass cheeks I clamped them together and moved from side to side to keep him out of my ass. He swatted my ass very hard and pulled very hard on my scrotum and squeezed until I stopped the wiggling around. The next thing I felt was the head of his cock pushing by my dry sphincter ring. I took a deep breath and tried to relax. It didn’t help much. The second push and he was thru my inter sphincter ring and in my tender rectum. It only took a couple more pushes before I could feel his ball bouncing off the backs of my legs. I don’t know how big his cock is but it felt like it was splitting me open. I wasn’t very happy when I felt him start to cum. He said give her this as a message pussy; with in minute of his cumming he was gone.
It seemed like hours before Miss Cindy got home. I did ask one of her friends who stopped by to call her. I didn’t tell her why just that I need Miss Cindy. She was pissed when she walked thru the door. She wanted to know what was so important that I couldn’t wait. I started to tell her what happen about the same time she saw the cum dripping out of my ass. Who did this was her only question. Even before she un-cuffed me she was on the phone with The Marine. She scream at him for quite sometime, during the call she un-cuffed me. I though about calling the cops but decide I didn’t want to explain why I was cuffed to the table to them or anyone else. Miss Cindy went on the rest of day about what an ass The Marine was. What didn’t happen was Miss Cindy asking me if I was OK or saying she was sorry. It was all about how could he do this to her.
I went into the guest room and packed up my suit case. I kissed her and told her I needed some time to think thru what happen. We talked a couple times after that day. I haven’t been back since.