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Bisexual Sissy Male Pickup

Bisexual Sissy Male Pickup

I was sitting around, sipping coffee in a late-night coffee house, the sort of place that puts up the artwork of young starving artists and brings in musicians who will play for nothing more than tips and a cup of coffee themselves. Across from me was an old friend and occasional play partner, Karl. Karl was indulging in a bit too much caffeine and decidedly too little sleep this evening.

That is his excuse for the challenge he put to me:

“You are spoiled. You have been playing so long with your fancy array of gear, you wouldn’t know what to do without it. ”

One suspects Karl was also feeling a bit masochistic this evening. He knew perfectly well how fond I was of using my teeth, fingernails and hands.

“I bet that if you had to start over with no toys, you would be lost,” he finished, grinning at me.

I smiled slowly back, “As a matter of fact, Karl, I could do quite well with nothing more than I have on me this moment. ”

He took a moment to survey my clothing: short black skirt, a tight little dark red shirt with a denim vest. Laying beside me was the small purse I was carrying this evening, clearly not big enough to be hiding much.

His grin widened, “Care to make a little bet on that?”

I smirked right back, “Certainly, but not with you as the victim.

That would not be sporting it is much too easy. Besides, I would hate to make you choose between trying to win and trying to lose. Let us stop by that swingers club and see if we can find ourselves a little bi boy or at least a boy who would not mind having you watch me tie and tease him. You can watch and see for yourself how I do. ”

“You’re on.

Just one thing–we do not take him back to your place. I would not want you to be tempted by all your gear. Take him to a hotel. Loser picks up the hotel bill. ”

“It’s a deal. ”

It was a Thursday night, so the swingers bar we went to was not crowded. There were maybe half a dozen single men circulating. Had we waited for the weekend, there would have been more people, but no single men at all–like most swingers places they discourage single men and they don’t allow them in at all during peak times.

I’ve heard that most women in the swinging scene like this, since they don’t have to fend off too many unwelcome advances. I do not care for it much myself, because I like to have as wide a choice as possible when I am on the prowl. However, I am not exactly a swinger myself, just a single and independent dominatrix. The first man we approached said he thought he might like to try submitting, but then proceeded to tell me exactly how he wanted it done: I was to tie him up like this, use these things on him, I must of course ditch Karl, he wouldn’t be watched by another *man*, although another woman would be acceptable.

I turned and walked off, Karl in tow.

The second one was more promising, a bi-curious boy I think. He had that look of hope-and-fear when he asked if there was any chance Karl might join in. Unfortunately, he could not handle the idea of anything kinkier than a little light bondage. I got his phone number–I like bi boys and he looked so cute when he got all nervous–but he wouldn’t do for tonight’s venture.

Karl spotted the next one, a guy in his mid to late 30’s sipping a drink over near the end of the bar. He was slightly older than my usual play partners but fit. We went over and spoke with him. He agreed readily to bondage and some pain, agreed as well to allow Karl to watch. He even had a little experience with cbt. I quietly noticed his shaven arms. A lot of guys shave their legs for various reasons, mostly for sports, but not very many shave their arms.

I choose a nice hotel, confident that I was not going to be picking up the bill for it. When we got in the room, I ordered Butch, my new little toy, to strip off his clothes. He was shaven from head to toe, as I had guessed. With a little wiggle, I removed my bra without disturbing my shirt. I dangled the bit of black satin from my fingertips.

“Hold out your arms in front of you,” I instructed.

Butch did so, and I pulled my bra up along his arms, fastening it on him in back before he knew what I was doing. I heard his breath catch. I picked up a box of Kleenex from the dresser and filled out his new bra, shaping it deftly into a convincing bust.

I stepped back and grinned at Butch. One glance at his expression confirmed my suspicions: he loved his new look.

Reaching up under my skirt, I removed my panties, aware of both Butch and Karl watching the wiggle of my hips as I slid the delicate bit of fabric off and held them up: black satin trimmed with lace on the sides. I tossed them to Butch, “Go ahead. Put them on. ”

He carefully slid the panties up his shaven legs. He didn’t have my hips, but he did have a bit of extra flesh which strained against the smooth fabric, trying to escape and point in my direction.

They fit well enough, and looked good against his smooth skin.

I took some red lipstick from my purse and applied it to his lips: the perfect touch. His large red lips seemed to leap out from his face, begging to be used. I walked around behind him and ran my hand down his back, down inside his panties. I reached under him and dug my nails into the loose skin of his scrotum, pulling it lightly backwards.

“Have you been a naughty girl?” I purred.

Butch swallowed hard, and seemed to remember to breathe, “Yes, ma’am. ”

“Lean forward and put your hands on the bed and spread your legs, my naughty little girl. ”

Butch leaned down and I smirked at Karl over his back. Karl conceded with a little shrug, and curled up in a chair to watch.

I reached down further and got Butch’s balls in my firm grip.

I pulled them down, then back, digging my fingernails in and giving little hard tugs until he gasped. I pulled his panties down in back to expose his ass. Reaching my left hand around and putting it down the front of his panties, I transferred his balls from own hand to the other.

I caressed his ass with my hand, then brought my hand up and lightly swatted him. He shifted slightly but I held him firmly in place by my grip on his balls.

“You have been a bad girl; such a dirty, sluttly girl. I can see it in your eyes. You will have to be punished, my little slut. ”

Butch moaned and spread his legs a little further apart. I began spank him lightly, pausing now and then to dig my nails into his balls or run my nails down his back and ass. After I got him warmed up nicely, I reached down and picked up his discarded belt without releasing my grip on his balls.

I doubled the belt over and brought it down on his ass. Butch put his head down on his arms and stuck his ass further out in the air to make a better target.

“Just look at what a little slut we picked up, Karl. What a darling little girl in her black satin and lace. ”

Karl agreed, “She does make a very cute girl. Who would have thought she was such a slut?”

Butch shivered at the sound of Karl’s voice.

“She really needs a better name. Something that starts with a K. Hmm… Kathy? No, she does not look very chaste, does she? Perhaps Kimberly. Yes, Kimberly seems like a good name for a pretty girl. With a name like that, maybe she can grow up to be a good serving maid.

“What do you think, Kimberly?”

“Yes, ma’am, thank you, ma’am. ”

“From now on it’s ‘Madam’ to you, my girl.

I brought the belt down on his ass, a dozen quick blows of hard leather. I watched his skin redden under the blows, and ran my hand across the red stripes, feeling the heat they radiated.

“Her skin does redden nicely, don’t you think, Karl?”

“Yes indeed… it matches her blushes when you tell her what a slut she has become. ”

Kimberly blushed harder, making her face almost match her red ass, indeed.

I pulled a hair brush out of my purse. I ran the back of it over my slut’s reddened ass, and gave his ass a couple of hard blows with it. Turning it over, I drove the sharp spikes of the brush into the sensitized skin. Reaching around I tucked it into the front of his panties, adjusting it so that the satin held it firmly in place, driving the sharp bristles into the skin of his ball sac.

I raised my foot and pushed the brush up hard, making it bite into his skin. I pulled my skirt off, feeling both men’s eyes follow me. I wrapped the skirt around Kimberly’s waist and buttoned it.

“There now,” I cooed, “Out of sight, out of mind. ”

I gave the brush a sharp blow, mocking my own words.

“Oh… Madam. ”

“Now how can I have my girl serve me?” I mused.

Butch licked her lips, looking from the soft jiggle of my breasts, unrestrained under my shirt, to the glisten of dampness on my naked thighs.

“Has my naughty girl been good enough? Maybe she should have a treat. ”

I arranged the pillows on the bed in a big heap. I guided Kimberly around to the foot of the bed.

I pushed the brush upwards and held it firmly, telling Kimberly to bring her legs tightly together.

With her legs together holding the brush in place, I picked up the belt I had used on her ass and wrapped it around her legs just above the knee, cinching it in place as tightly as I could. Taking off my denim vest, I twisted it into a makeshift denim rope and bound Kimberly’s wrists together in front of her.

I pushed Kimberly forward onto the bed, where she lay face down.

Circling around her, I settled myself down in the nest of pillows, laying back comfortably and running one hand up my thigh.

“Now you may come and serve me, Kimberly. ”

Kimberly scooted awkwardly across the bed, crawling on her elbows and bound knees, each movement driving the bristles of the brush into new and more painful places. As I watched her struggles, I relaxed on my pillows and let one of my hands drift up under my shirt to rub across my breasts.

I trailed my other hand over my thigh and allowed myself to rub my clit, playing lightly with myself as Kimberly struggled to reach me.

A glance over at Karl showed that he was ahead of me–having already unzipped his pants, he was running his thumb lightly over the head of his cock as he watched from his chair.

I massaged the swollen outer lips of my pussy, and held out my damp finges for Kimberly to lick clean.

Her bright puckered lips wrapped around my finger enticingly as she sucked my fingers clean. She pulled herself along the bed with her elbows, finally close enough to reach me with her head. I wrapped my fingers in her short hair and fucked her head down into my lap. Kimberly reached out eagerly with her tongue, licking all traces of my moisture from my thighs. She licked her lips, then stuck her lips between my lower lips, parting them for her tongue to enter, seeking my clit.

“Such a greedy little slut,” I murmured as she licked her way up and down.

I came once, quickly, and then pushed her head away. I stood up, leaving her laying across the bed, her weight still driving the sharp points of the brush up into her tender balls.

I motioned to Kimberly to push herself up onto her elbows, then I flipped Kimberly’s little skirt up onto her back, pulling her satin panties down to the belt that held her knees bound together.

My hairbrush fell to the bed and I picked it up. The skin where it had pressed was dark red, with clear impressions from the bristles. I picked up the brush and bounced the bristles against the head of her swollen cock.

I looked thoughtfully at her cock, “Tsk, tsk. My girl is still such a slut. Whatever can I do with this?”

I pulled some lotion out of my purse and rubbed it onto my hands as I looked down at her.

I ran one finger down her ass, feeling my way down to her puckered little hole. I rubbed my lotion-covered fingers back and forth over that sensitive skin.

Kimberly thrust her ass into the air to meet my hand, and pressed her cheek against the bed. I encircled her cock with well-lotioned fingers of the other hand as I eased the tip on my finger into her ass. I ran my hand up and down her shaft, spreading the soothing lotion over her abused skin as I thrust my finger more fully into her ass.

Kimberly moaned loudly and then whimpered as I wiggled my finger inside her. I pulled my finger out of her, and then began rubbing lotion onto her balls as I thrust into her with two fingers. I massaged the last of the lotion into her tender skin, then allowed my free hand to rest on her hip as I thrust in and out with my paired fingers inside her ass.

“I have no use for that bit of male flesh myself but,” I leaned down to stage-whisper to Kimberly, “if you asked Karl really nicely, maybe he could think of something.

” Kimberly whimpered again, then twisted her head around so that she could see Karl, playing with his cock and grinning at the two of us.

“Of course,” I added cheerfully, “it’s entirely up to you. You could just stop and go home now. ”

I thrust my fingers deep and twisted them against one another inside her.

Kimberly buried her face in the comforter for a moment, then raised her head and looked at Karl.

She licked her lips u*********sly, and whispered, “What would you do to me?”

Karl walked slowly over to stand in front of her as I continued playing slowly with her ass.

“Just a fair trade,” he said casually, “you take care of my problem, and I’ll take care of yours. ”

Kimberly closed her eyes and then nodded. Karl stepped closer and pressed the tip of his cock against her mouth.

I watched as her lips parted and she took the head of it into her mouth. She sat frozen there for a moment, then began to suck rhythmically. She opened her mouth wider and took in as much of his cock as she could, letting it slowly slide out of her mouth and then pulling it quickly back in.

With my fingers in her ass, I set up a tempo which she mirrored in her sucking.

Penetrated from behind, having her ass fucked by my fingers and her mouth full of cock, her body shifted back and forth between the two of us, used as a toy which amplified my movements and translated them to Karl’s cock. She lost herself totally, moaning and writhing as she strove to take all of Karl’s cock, tried so hard to lick and suck his cock as she was being taken herself. I slipped a third finger in between the two already in her ass.

Her little hole was so tight I barely made it. Her muscles strained helplessly, but could do nothing to prevent me from thrusting into her ass, filling her hot flesh with my hand.

She clearly welcomed the cock in her mouth now, glad to have something to suck on, something to do to relieve the overwhelming sensations as I fucked her ass, filling her hole, pushing deeper and harder into her than she had ever felt before.

Karl gave a little moan and leaned forward against my shoulders as he came deep in Kimberly’s mouth. His cum leaked out around the corners of her mouth, and dribbled down her face. She released him and hung her head down, gasping a bit. I smacked her ass with my free hand, “Clean him up, my little slut. ” Kimberly raised her head and licked along his shaft, cleaning off the traces of his cum.

Drops of cum were already drying on her cheek, alongside the red smear that was all that remained of her lipstick. Combined with the look of hunger, shame, and desire on her face, she looked ready for the cover of “Crack Whore Magazine. ”

“Free her hands and hand me the vest and your belt,” I instructed Karl.

Once her hands were free I pulled her arms behind her and cinched her elbows together with the belt.

I took the vest and put it in her mouth, tying it behind her head. I pulled back on the ends of the vest, forcing her to lean back against my body. I held her in place, my fingers still in her ass and moving in a slow but steady rhythm though I didn’t have room enough to fully withdraw them to thrust them in and out.

Karl knelt in front of her as I held her, bound and pinned against me.

Kimberly watched him as she might an approaching snake. He leaned down and ran his tongue up the shaft of her cock, then licked his lips and pulled her inside his mouth in one stroke. She turned and pressed her face against my breast, not wanting to watch but unable to protest the exquisite feel of Karl’s mouth on her abused cock.

I watched as he gave my slut a quick and expert blow job, wiggling my fingers inside her ass as in time with his movements.

Finally, Kimberly came with a loud moan, mostly stifled by the cloth in her mouth. Karl licked up the last drops of her cum and helped me to release her from her restraints. Kimberly lay on the bed, breathing deeply for a moment. I looked over her body at Karl.

“I guess you’ll be paying for the hotel room,” I said to him.

“I guess I will. ”

“We should do this again sometime.

“It could be an interesting summer. ”

We grinned at one another and I helped our slightly dazed guest into the bathroom to clean up.

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