A Matched Pair

My girlfriend Wendy was down for the week.  It was Saturday, and my friend Mark came over after dinner to go out with us.  After a few drinks at my place we asked Wendy what she’d like to do.  “How about we go across the highway to Charlies’s?” she said with a sly smile.

Charlies’s is a strip club known throughout the area.  Mark and I didn’t need any other prompting, and soon all three of us walked over to the neon and noise that signaled that the club was hopping.  We walked in and took a side table.  “So dearest, are you looking for a lap dance?” I asked.

Wendy smiled at us with that dazzling smile of hers, “Oh, please.  I think it would be fun!”

Mark turned to her, “Do you have any preference in type of girl?”

“Big tits, natural of course, and preferably blonde,” she replied with a wide grin.

Mark was up like a shot and soon had a buxom blonde dancer.  We moved Wendy’s chair back and were treated to my sexy girlfriend having a great lapdance.  Mark and I sat drinking our drinks and enjoying the show, and I’m not sure which one of us was enjoying it more.  Wendy was reserved at first, but with some prompting began to get into it.  Her smile grew even wider as the blonde grabbed her hands and brought them up to feel her large tits.

Well, we stayed there for a while, drinking and getting Wendy lapdances and generally enjoying ourselves.  I could see that Wendy was getting excited by all the attention until during one break she finally leaned over to us.  She put her hands under the table and grabbed both our cocks startling us, “Boys, I think it’s time we blow this popsicle stand and go back, don’t you?  I can think of some  more fun things do.”

Without waiting for a response, she rose, took our hands and led us out of the club.  We walked back hand in hand to my place, and went inside. 

Now, I should probably mention that Wendy has a dominant streak in her, and occasionally will want to “play”.  Mark and I are both accomplished successful men who are in leadership positions.  This makes submitting to her all the more exciting as it’s such a different side of our personas.  It was obvious that she was in the Dom role, because as soon as the door closed she turned to me and said in a commanding voice, “Jeremy, pour all of us drinks and join Mark and your mistress in the living room.”

I made double Jack-and-cokes for Mark and me, and a Kahlua and milk for my mistress.  Bringing the drinks to the living room I saw Mark standing in the center of the room.  He was already buck naked.  Wendy was in the overstuffed easy chair, right leg crossed over left, her high heeled boot swaying back and forth as she tapped a riding crop in her palm. “That was slow, Jeremy, you’ll going to have pay for that.”

“Sorry Mistress, here is your drink,” I said while presenting her glass.  I stood right there knowing if I took any liberties, she would find it cause to punish me.  “You may have a drink, and let my Servant have his as well.  You are going to need it tonight.  I’m feeling in an especially dark mood.”

I gave Mark his drink and stood next to him.  We both drank quickly, the warm whiskey feeling good going down my throat.  When I finished I stood still, eyes straight ahead.  I could feel Wendy’s eyes on me, and hear her slowly sipping her drink.  “Hmmm boys, you are not quite the matched set yet.  I prefer my subs with less clothing.  Strip Jeremy, and be quick about it.”

I removed my clothing as fast as I could, folding it, and setting it aside.  I then resumed my place standing next to Mark.

“Better, much better.”   My sexy dom let us stand there on display for several minutes while she slowly finished her drink, letting the tension build.  Then she stood up and walked over to us, coolly surveying her men with a critical eye.  She started with Mark, “I see you have been working out Servant”.  She trailed her crop down his chest.  “However, this little thing isn’t very good for me to play with, is it?” she asked while tapping his dick with the tip of the crop.  I could only assume he was flaccid as I knew I was.  He grunted as her crop tapped his prick harder.  One harder rap elicited another gasp.  “There we go; I knew your tiny dick just needed a little encouragement.  It still has a long way to go to satisfy me though, but it’s a start.”

I thought very erotic thoughts so she wouldn’t find my cock limp as well.  I just imagined how hot her body was, and how good it felt to be in her and I could feel my manhood begin to grow slightly.  Good thing too because she finished with Mark and came over to me.  I could feel her eyes on me as her crop slowly stroked my sensitive skin.  “Not bad my dirty little whore” she commented.  It moved down until she stroked my dick with the tip of her crop.  Moving around my still form she spoke sternly, “but stand straighter".  I felt her crop lash out against my naked ass, stinging it sharply.

“AUGH” I cried out.

“What?  I didn’t give you permission to say anything.  Did I?”

I answered at once, “No Mistress, you did not.”

She moved up against me and I heard her voice whisper in my ear, “Then you shall taste my crop again, until you can learn not to say anything.  You aren’t earning any points with me this evening.”

I felt her crop again crack against my ass.  I bit my tongue and kept from crying out despite the pain.  9 more times it was used against me.  “Oh, that’s a nice shade of red.  Mark, you don’t match him, whatever shall I do?”  I heard a crack and knew that Wendy was now whipping his ass as well.  He got ten strokes from her strong arm.  He learned from my mistake by keeping his cries silent, but I could hear his breathing coming hard and fast as she worked him over.

“Lovely, just lovely; I do so like to have things nice and even.  I have to keep things fair until one of you proves his worth and my favor.  Damn it subs, you are both soft again!  This won’t do at all.  Neither of you are making me happy tonight, I see a lot of training is in order.”

She went over to the pegboard that holds our “toys” and took two cockrings down.  “Put these one.  The one who does it first will get a reward”.  She then held them up in front of us.  I quickly took the one I was given.  It was a set of three rubber interlocking bands.  One goes around the shaft next to the body, the second around the sack pulling it downward, and the third band loops around the cock in front of the other two. 

I quickly put it on, having to separate each ring, and attach it after wrapping around my manhood.  Once done, I sneaked a peak at Mark.  He was fumbling with his.  It was a wider studded band.  One strap goes around the base of the shaft like mine, but there was a strap that separates the balls before coming up over and around the dick. 

“Seems my whore has the advantage of practice,” Wendy said after Mark finally got his on.  Wendy took our cocks, one in each of her hands.  Both our pricks were now standing at attention, the cockrings keeping them firm.  Squeezing them hard, she snickered as we gasped, “Now that’s how I like my subs; hard and ready for my use.   It seems Jeremy wins a small prize for being first.”

“Thank you Mistress,” I said, beaming.

She released Mark and came over to me.  She took my head in her hands and gave me a deep kiss that sent shivers to all the way down to my toes.  She then started to stroke my erection.  “See how good performance brings rewards, subs?”  I could feel the tri-bands biting into my shaft as I grew even bigger.  She began to stroke harder and faster.  I used every ounce of determination I had to avoid moving.  I also knew I couldn’t cum unless told to.  My mistress put her face right next to mine, and gazed into my eyes.  “Having problems Jeremy,” she asked with a grin, obviously seeing the strain on my face.

“No Mistress, I am happy to have pleased you.”

“Ah, yes, good answer.  However Servant, since my dildo whore got a reward for winning, what do you think happens to you for losing?”

I heard a Marks soft reply, “I failed my Domina.  I expect to be punished.”

“Right answer, down on all fours,” Wendy said in a stern voice.

As Mark hastened to comply, my mistress went back to the pegboard and took down a pink paddle.  It was about two inches wide with XOXO on it.  She came back, came up to me and turned me to face Mark.  “Jeremy, you need to observe what happens to bad subs.”  I saw my friend on his hands and knees next to me, his ass still red from Wendy’s crop.  I knew what was to come and was happy I won her first challenge. 

Wendy moved over to Mark’s body and I saw her caress her paddle.  “I just love the way these X’s and O’s leave their mark in your ass, don’t you?  You need to kiss my paddle before it leaves its kiss on you.”  She then put it in front of his face and pulled his head up by his hair.  He kissed the paddle and she let his head drop, walking around his body. 

She reached back and brought her paddle down on his rear with a resounding *crack*!  He winced and lurched forward.  “Count out loud servant, you are to receive twenty as your punishment.  If you lose track, I’ll be happy to start again at zero.” 

She then began to work on his ass with her paddle.  Each time she lay into him, the sound filled the room and he lurched, and said the count.  She got to ten then picked up the pace.  However, when she got to 15, she stopped suddenly, but Mark lurched forward in anticipation of being hit.  “Oh my gods!  I can’t believe you did that.  You don’t ever try to avoid my punishments, subs.  Just for that you get five extra.”  I winced as I watched Wendy turn Mark’s backside into a bright shade of red with several welts starting to form.

As she finished all 25, she then surveyed her handiwork.  “I bet you’ll be quicker fulfilling my tasks now.  I see we have you two mismatched again.  This won’t do.  Dildo Whore, get on all fours next to servant, now.”

I dropped down to the floor and lined up next to Mark.  I could hear his heavy breathing and feared she was going to make my ass match his next.  However, our devious mistress had her own plans.   “Now, that is a fine sight.  Two strong men down on all fours like dogs.  I know just what to do now to complete that picture.”

Again a trip to the peg board was made and Wendy came back.  I couldn’t see what she had since I was on the floor, head down.  She leaned down and I felt her encircle my neck with a wide collar and pull it tight just to the point of restricting my breathing.  Moving over to my friend next to me she redid the procedure.  I then felt her attach a leash to the collar with an audible *click*.  Mark was then also leashed. 

With a laugh Wendy jerked on our leashes, “Oh now that’s perfect.  My subs turned into the dogs they are.  I think it’s time to take you two for a walk, move out my doggies and don’t be slow or I’ll have to quicken your steps with my crop.”  I felt a sting on my ass as she drove home her point by cracking her crop against my ass, then she did the same to Mark’s.  We moved out crawling behind her as she led us across the floor.

This was total humiliation, naked, collared and forced to walk on all fours next to my friend in the similar predicament.  Wendy led us around the living room, to the kitchen and had us heel there while she got herself a new drink.  Then she walked back to the living room to the big sliding door leading out to the patio.  “I bet my doggies need to use the bathroom.  Can’t be making a mess inside now, can we boys?”

She opened the door and led us out on the patio under the stars.  It was tough crawling on my knees like that and they were getting very sore.  Wendy stopped at the edge of the patio and said, “Now boys, if you have to pee, you know what to do.  I won’t be giving you another chance.”

I had to go a little bit, but didn’t want to humiliate myself further.  I guess Mark had more to drink than I because he moved to the edge of the patio and lifted his leg.  Wendy sat in the patio chair and watched Mark try to pee like a dog.  Unfortunately, with the forced erection, the stream shot straight ahead and almost hit him in the face.  He jerked back, and finally got it under control.  When he was done, our Mistress yanked on our leashes and said, “Heel boys, one on either side of your Dom.”

We crawled over to the chair and took up position on either side of her.  We sat on our haunches as she sipped her drink.  She patted our heads and said, “What a perfect evening. I had some lap dances, some good drinks, now I have two subs as my doggies at my side.  You know boys; I think it’s time to turn our playtime up a notch.  I believe I have a contest for you two.”

She then got up and led us on our leashes back into the house.  After closing the door she had us move to the center of the room again.  “Now subs, we’re going to have some fun.  Up now, but stay on your knees.”  We complied and she took the leashes off, but left our collars on along with the cock rings.  We were side-by-side, naked and kneeling in front of her.  It was a position that enhanced her commanding role and emphasized our submission to her will. 

She looked into our eyes and with an iron tone said, “Now here is the contest.  You are both to start stroking those cocks of yours.  You are NOT to cum.  I want to enjoy your performance for a few minutes.  Once I’ve tired of your little show, I will tell you how to win.  Now begin to jerk off my subs.”

We both began to masturbate as she went back to the chair with her drink.  My knees were killing me but it felt good to jerk off.  It was very strange to be next to Mark as he was pleasuring himself as well.  I could feel my cock strain itself against the cock ring as it got even bigger.  Wendy was watching us with glee in her eyes.  “Pull on that meat harder boys.  It’s precious to see you two jerking off like bad little boys.  Let me tell you that you DON’T want to lose this contest.”

I continued to jerk off.  I had to swap grips and techniques to avoid cumming too soon.  I heard Mark groan a few times and knew he was barely holding on.  After 10 minutes of this, my cock was as sore as my knees.  Wendy finished up her drink, stood up, and walked over to us.  Standing tall in front of us, she was impressive in her dom role.  “Now the contest is about to begin, my pets, you are to cum on my boots when I tell you.  Don’t miss or you’ll have to clean it up.  I’m interested in how much seed you are going to spill.  Now… CUM!”

I jerked off hard, rubbing right in the sensitive spot under the head of my prick.  I felt my dick begin to grow and my orgasm near.  However, just as I was about to cum, I heard Mark cry out and saw his white seed spew onto Wendy’s boots.  “NO” I yelled as my own orgasm hit me.  I almost blacked out as I felt my balls tighten and my own semen surge out of my throbbing cock.  It flew out onto Wendy’s other boot.

I was breathing hard, my dick throbbing as my orgasm subsided.  I heard Wendy’s voice, “Oh, dear Jeremy, it seems that you came second.  It appears you’ve lost my little challenge, and that means you are going to have to pay the piper – or Mistress in this case.”

My head bowed as I realized that my night was going to get a lot harder.

A Matched Pair

Part II

Wendy put her hand into my hair and pulled my head up to look at her, “It appears that my boots are soiled, Dildo Whore.  You better go get something to clean them up quickly or I’ll have you use your tongue.”

I got up and quickly ran into the bathroom to get a towel.  I returned to the living room and knelt by my mistress.  Her foot was tapping and Mark was still kneeling next to her, cock in hand.  I used the towel on each of her boots in turn, wiping up the white cum that was sprayed onto them.  I was shocked at how much fluid there was, but I guess I shouldn’t have been surprised as she had kept us on edge for so long.

When I was done, I tossed the towel to the side and knelt next to Mark, figuring that was what Wendy would want. 

“That was slow, Dildo Whore.  Next time be quicker about it or you’ll taste it instead.  Nice try lining up next to Servant, but you aren’t going to be so lucky.  Go get the pony bench, and bring it in here.”

I went into the bedroom and brought out the pony bench.  It was a contraption I created to Wendy’s specifications made from PVC pipe.  There were two horizontal sections about 4 feet apart and parallel which were connected by a center section.  It looked like a giant capital I on the ground.  On one end was a vertical “T” bar about 2 feet from the ground, and on the other end was a vertical bar which had a hard PVC round section.

“Put it next to the chair and mount it.”

After placing it where she indicated, I bent over the vertical “T” bar, putting it against my hips.  On all fours, this placed my wrists and ankles right at the spot where the ends of the horizontal poles were.  My mistress came over to me, an opened up the circle which I put my head into, then she locked it around my neck.  My wrists and ankles were then encircled with leather straps and tied to the four corners of the “I”, forcing me into a pony position on all fours, ass up.

Wendy spanked my ass with a loud *smack* and said to Mark, “How does he look Servant?  Aren’t you glad you were able to win my challenge?”

Mark answered, “Yes my Domina, I am very happy.  He looks very vulnerable and helpless.”

“You’re right.  Now that I think about it, I probably should have had him put wheels on the pony bench. Then we could have wheeled him outside to the parking lot for all to view.  Oh well, an improvement for next time.”  Wendy then came over to me and ran her fingernails lightly down my spine causing me to attempt to twitch. 

“Servant, my drink needs refilling.  Go get me a refill as I ponder DW’s fate”.

“Yes Mistress, right away.”

Wendy sat down in the chair and put her feet on my backside.  I could feel the heels of her boats dig into my ass cheeks as she awaited her drink.  When Mark returned she said, “Servant, you are to rub my shoulders as I have my drink.  It’s tough work keeping you two in check, you have no idea.”  She was quiet for a minute as Mark rubbed her shoulders and neck.  She kept digging her heels into my ass and questioned, “Just what to do, what to do?  Decisions, decision…  If it wasn’t so late I’d order pizza and have the delivery boy just come in to find you as my table.  That would be sweet.  I guess I’ll have to come up with another way for my slave boy here to pay his penalty.”

She stood up and picked up two clothespins.  She leaned down and fastened them to my nipples making me wince in pain. “Oh, servant, help your mistress out and go fetch the large black dildo for me please,” Wendy asked in a sinister voice while digging her nails into my back.

Mark quickly answered, “Yes, Domina, at once.”  I heard his footsteps recede and I felt Wendy’s breath on my neck.  She bit it and whispered in my ear, “Oh Dildo Whore.  I think it’s time for you to earn your name.  What do you think?  Oh wait, it doesn’t really matter what you think, since you lost the contest, are now helpless and I get to do what I want.”

Mark returned with the sinister toy in his outstretched hands.  It was twelve inches long, very thick, and black.  It was double-headed and flexible.  Wendy brought it around to my head and stuck it in my face. Smacking me with it across my face while saying, “Here it is my pet.  Just think, in moments this will be shoved into your asshole, fucking you like the dildo whore that you are.  Since I’m a generous mistress, I’ll allow you to lubricate it if you like.  Open up!”

She then forced that monster dildo past my lips into my mouth.  I tried to pull back, but strapped to the pony bench, I had to feel that hard piece of plastic invade my throat.  I tried to get it wet as she moved it back and forth, fucking my mouth.  Gasping for breath and almost gagging, she kept ramming it in and out of my mouth.  Finally, tears in my eyes, she removed it and went around my bound body.  I felt her spread my ass cheeks and put the head of her black dildo against my asshole. 

I tried to move, but was secured too well, I felt that monster press against my tight hole.  It wouldn’t go at first, but then Wendy gave a grunt and shoved it into my inner recesses.  I yelped in shock as I was fucked by her toy.  I didn’t think I could take any more, but she kept pressing it in, further and further.  When I was sure I was about to taste it, she stood up, and surveyed her work, saying, “Oh my yes, that’s just the way my dildo whore should be; bent over and fucked with a big dildo hanging of his gaping asshole.”

Then her voice turned nasty and she said, “But again I don’t have the matched set anymore.  Jeez, what is a girl to do?  Servant, get on all fours.  Then back up with your ass facing Dildo Whore’s.”

“But Domina, I thought I won the challenge?” Mark asked.

“Are you questioning your Dom?  Bad idea servant.  Don’t worry, your reward is in store for you, but right now I’m having my fun.  And you are ruining my matched set, so if you don’t want to feel my wrath, you will comply, now!”

I couldn’t see what was occurring, but I felt Mark get on all fours behind me.  Wendy instructed him to back up a few times and I felt pressure on the dildo in my ass.  Mark let out some grunts and groans.  Then I saw my mistress move over to the side of us, put her hand on her chin and smiled.  “Oh that’s perfect.  Now both my subs are on all fours, with the dildo connecting them by their asses.  Since my dildo whore can’t move, Servant, you are to push back and forth and fuck each other while I go enjoy my drink.”

I felt Mark move back, forcing the dildo further into me. I grunted and was forced hard against the pony bench.  Then he leaned forward, slowly pulling the rubber cock out a little.  I couldn’t see what it looked like, but I could feel myself getting fucked up the ass every time he moved.  I heard Wendy laugh and turning my head saw her sitting back in the easy chair, surveying us with a critical eye. 

“Oh my gods, this is so perfect!  Subs, you are in the perfect position, on all fours and fucking each other for my enjoyment.  Servant, pick up the pace a little, you’re being too nice to Dildo Whore.  He can take it harder, trust me.”

I felt Mark quicken his movements, and my ass got violated harder.  He was grunting in time with my own moans of pleasure/pain.  My arms were getting sore from being forced in the position they were in, unable to shift position.  After several minutes of this, I saw my mistress get up and get her strap-on harness.  She stepped into it after removing her dress.  It was an awesome sight, her perfect nude body shining in the light, an eight inch hard rubber dildo sticking out of the center of her waist. 

“That’s good Servant, you’ve pleased me and you can stop now.  You’ve prepared him nicely and now it’s time for me to take over fucking my Dildo Whore.  Pull out and stand up next to me so you can watch me fuck him.” 

I felt Mark stand up and the big black double-headed dildo came out of my asshole.  He stood next to Wendy, looking all sweaty and worn out.  She pulled his hands behind his back and fastened them in place with a pair of metal handcuffs.  A ball gag then followed and she made him open his mouth.  Fastening it tightly around his head, his mouth was forced into a grimace with a red ball keeping him silent.  “We can’t have you making noises and ruining Dildo Whore’s fun, now can we?” she asked.  Mark grunted and shook his head no.

Not finished, she then took a blindfold and coming over to me put it over my head, blocking off my sight.  “Now now, Sub.  No peaking.  I want you to be able to focus on how I’m going to dominate your helpless body as you pay your penalty for losing the competition.  It’s time for you to get my toy wet again, open up that mouth.”

The blindfold was taking away my sight, but as instructed  I lifted my head as far as it would go and opened my already sore mouth.  I’m sure my ass was already wide open, but didn’t want to let my mistress down by not getting her dildo lubricated.  I felt her move in front of me and pull my head up by my hair.  Then I felt her push her dildo into my mouth again.  This time it was much smaller and I was able to wrap my lips around it easier.  I felt her hips move slightly and the dildo slid deeper in my mouth.  It was horrible being forced to suck her off like that, helpless to move.  I was sure Mark was glad he had won the contest.

Just then I got a shock as I felt someone’s hands on my hips and something pushed into my already violated ass.  I grunted and shook, trying to figure out what the hell was going on.  I heard Wendy laugh and she ripped the blindfold from my eyes.  All I could see was Mark pressed up against my face!

“Surprise, Dildo Whore!” I heard from behind me.  Since he won the contest I figured I’d reward Servant with a blowjob.  However, I wasn’t about to do it, so I guess that just leaves you!”

I was trapped in the pony bench, in the middle of Mark and Wendy.  She had her strap on buried in my sore ass while Mark, handcuffed, had his dick into my mouth.  I had been turned into nothing more than a whore for their enjoyment, a fuck toy for their pleasure.  I know Mark hadn’t planned on this, but he seemed to have gotten over any reticence as he began to thrust faster into my mouth.

“That’s it servant, he can take it.  If you want your reward, and not take DW’s place, then you are to fill his mouth with your spew.  I want to see him humiliated, forced to eat cum for the first time.”

She kept up the pace, splitting my hole with her strap on while spanking my ass.  Whenever she thrust into me, I was pushed forward, taking Mark’s swollen cock further into my mouth.  All I could do was gag on his meat, my saliva pouring across it.  I heard him start to moan, and his hips began to buck wildly.  I was feeling his dick begin to grow in size, stretching my mouth.

“Yes, now, feed him your cock!” Wendy yelled with abandon.  Mark shuddered and made one wild inarticulate yell against the ball gag.  “That it, take it Dildo Whore… get us off!  Fuck this is hot, why didn’t I ever think of this before?  Oh yes, I’m about to cum, jam your meat into him my Servant!”

The both bucked and jammed their respective cocks into me hard.  With a yell, my mistress grabbed my hips and forced her strap-on deep into my sore hole.  I felt Mark shudder and then it happened.  I felt his hard cock pulse and I felt it spew into the back of my throat.  I didn’t want to take it, but it sprayed deep into my mouth,  his sperm leaking out around his cock and down my chin.  He groaned and slumped back, finally freeing my mouth as I gasped, trying not to think of what just happened.

Wendy sauntered to the chair, slumped down and put her feet hard onto my back with a thump.  “Oh my pets, you have done well this evening and made me proud.  That was a great release I just had.  I may just leave you tied up like that until the morning when we can start a new competition.”

Mark groaned against the ballgag as I just slumped; locked in the pony bench, cum slowly dripping off my chin.