This is a print version of story Cross dressed slavery by stig1963 from

Cross dressed slavery

Oh just try it on, don’t act so…stereotypical.”

I started to protest again, I mean I was not trying to be a jerk, but I did not feel like serving as Leena’s dress dummy all afternoon. I felt uncomfortable enough around her and her clothes. The way she dressed made me crazy and I knew she would tease me all afternoon if I let her. It was my own fault really, I approached her at her last ‘fashion show’ and offered to take some pictures. I really did like her designs, but mostly because of my own peculiar fetishes. Leena worked a lot with sweaters and wool, knit creations she called them, and those creations did something to me. I remember clearly her first show, and the first model, coming out in a striped wool tube dress that started at the chin and descended all the way to her ankles. It gave me goose bumps. So I had become friends with her, even shot some photos, but I did not think I could try any of her clothes on without revealing my…peculiarities. And here she was asking me to stand in for her model, while she finished her latest dress: an angora sweater dress that looked like something Morticia Adams would wear. I stammered another excuse and Leena let me off the hook for the moment. She did have a way of getting what she wanted though, grinning up at you from under her dark severe bangs. She was short, and very buxom, and dressed in her own clothes she was VERY attractive. I may love sweaters, but it is a tight sweater on a full-figured woman that really kills me.

She smiled again at my obvious embarrassment, and offered me a glass of wine. Big mistake. Three glasses later I was no longer embarrassed. It kept raining outside Leena’s studio, which was usually packed with assistants and models but not tonight. She asked me again to help her out, and this time I barely hesitated, hopping up on the platform to hold some pins. She and I worked like that for a while, and each time her sweatered breasts (she was wearing a soft cashmere cardigan over a tight little black sweater) brushed my body I felt a thrill run through me. Finally she asked again if I would try the dress on, sighing with frustration, “If I don’t see it on someone I won’t know what it looks like.”

I touched the soft angora dress again, dying inside to try it on, to live out this secret fantasy I had tried to bury for years. What would she think of me if I tried on this dress? What would it feel like? My desire stirred, and I agreed with breathless nonchalance that I would try it on. SO I lifted the dress off of the wire frame she had been using, wondering how to put on a dress like this. Leena laughed at my clumsiness. “What are you doing?”

I stopped trying to find the entrance to the sweater dress. “Max, I’m serious here, that dress is worth about $1600 in materials alone. You have to take off your clothes, that belt especially.” I giggled again. I could not stop. Then she told me I could be a model, flattering me as she pulled my pants off. So there I was standing in front of her, in my boxer shorts, giggling with embarrassment, and trying to figure out why I felt so…malleable.

Leena stepped back, appraising my skinny male frame. She was all business which relaxed me somewhat. “Y’know Max,” she said, “your boxer shorts are gonna bunch up under the dress something awful.” I laughed at this, inappropriately perhaps, but Leena continued: “And your leg hair might snag the angora – I can probably cover that up.”

I tried to regain my composure, but I was starting to feel like a noodle dropped into boiling water. I groped for another sip of wine, while Leena went off to find something to cover my legs. She came back with a pair of lycra tights that kind of shimmered in the late afternoon light, and insisted I put them on. I was laughing uncontrollably now, but Leena did not seem to mind. She ushered me off to the bathroom where she shut the door and told me to change into the tights, she called them tights, like what ballet dancers wore. Now she was telling me I should have been a dancer. I looked at my narrow masculine frame and laughed again. I shimmied out of my boxers, and pulled the tights up my thin legs. They covered my leg hair in a veil of opaque fabric, and clung to me like a second skin. Suddenly I got an enormous erection, and I stopped laughing and giggling. What was I doing? How had this happened? I tried to think away the hardness in my cock, but it was standing straight up under the tight lycra. What would she think? It finally subsided, and I watched the taut bulge shrink down to a semi-soft bump, and just in time as Leena barged in, grabbed my hand and dragged me back to her dress platform.

“Okay, now stand up straight.” She sounds like my mother, which helped.

She pulled the soft dress up around my ankles, easing it past my hips. She never stopped talking, telling me the tights made it easier to get the dress off and on, telling me I looked great. When she reached my waist, the first place my skin was exposed, I stopped giggling. The angora was so soft and sensual, it penetrated my skin sending goosebumps up the soft flesh along my ribs. I think Leena noticed. I was glad my cock was covered, under the sweater and tights. She eased the dress slowly up my sides, but stopped at my armpits. She said, “You know, you actually don’t have the right shape up here, can you hold on a second.” I nodded, my embarrassment growing along with my cock. She left the rest of the dress bunched in my arms, and ran off to her office. When she came back with the old foundation garment that had been on her dressing dummy for months, I knew I was in trouble. I opened my mouth to protest, but Leena laid her soft hand over my lips. She winked and said, I won’t tell if you won’t.

I was flabbergasted, but I let her strap the long line brassiere around my waist, pulling me in there, and filling my chest out incredibly. The cups were stiff, forming bold pointed breasts, that reminded me of cadillacs. The dress slid over them like a second skin, and I was suddenly looking down at two sweatered breasts standing off my slender form. Leena was busy at my back, buttoning the high neck all the way up to my chin. She was so busy I don’t think she saw me gently caress my new curves, the soft aura of angora highlighting the feminine silhouette. Why did this feel so good? My cock was no longer throbbing
with excitement, it felt moist and hot down there, but what felt better was the soft feel of the angora on my body, and the glimpses of my feminine self in the mirror. It was like a dream I had had.

Suddenly Leena was turning me around, pulling at the fabric, admiring her work…and then the phone rang. Leena winked and said she would be right back, leaving me to stare at myself, to touch the sweater girl image before me. I brushed my hand across my crotch absently, feeling the angora’s cool touch through the lycra tights. I arched my back a little to bring my breasts forward. Hopefully Leena did not see me, as she came flying back into the main room with an anxious look on her face.

I asked what was wrong, and she said that the BIGGEST Japanese buyer was in town for one night only, and had called to see if he could look at anything before he flew back to Tokyo. It was a once in a lifetime chance, this guy never made studio visits.

Great, I said, what’s the problem? Leena looked at me, with careful consideration. She said, he is going to be here in fifteen minutes. I have no one to model the clothes. I waited. Except you, Leena said.

I started shaking my head, saying I had enough, and there was no way some guy was going to believe I was a model. I mean look at me, I almost shouted, do I look like Cindy Crawford to you? Leena stood back smiling. Well, she said, you do have a nice pair of legs. But we would have to hide your face somehow.

My mouth dropped open. Hide my face!? Yeah, I said, you’d have to completely hide it! Like with a paper bag. But Leena didn’t listen. She was off and running again, darting into her office, while I felt for the snaps at my neck to try and get out of this thing. She called back, Don’t touch anything. And what size are your feet?

I stammered a reply, still trying to free myself.

But then Leena was there in front of me, looking sad. Don’t, she said, and the look in her eyes melted me. OK, I growled, but you owe me one. She smiled and danced up onto the platform. Her breasts pressed against mine, and she kissed me hard, way harder than friends usually kiss. She said, Do what I say, and I will owe you the hugest favor.

She slid two large high heels onto my stockinged feet, and told me to walk up and down on the platform, to get the feel of it. Luckily they were three inch heels, and not that hard to master. I was sure however that I looked like an idiot. Then Leena appeared with a strange leather mask, with a plume of real blonde hair sticking off the top. She shrugged and said, Bondage hood. She explained that she had designed some fetish wear when she was starting out, and that this had been a left-over prop. With exaggerated care she slipped it over my face, fastening it behind my head. I could see through the eyeholes, although they were not that big, and my mouth was visible. My lips were big for a man’s so Leena seemed to think that worked to my advantage.

She was excited by the bondage look and asked me to put my hands behind my back. I did, and she smiled, saying I looked stunning. She said keep your hands there, and she ran off, while I looked at my image in the mirror. I couldn’t help it – I looked ravishing. I stepped off the platform and headed for the mirror. My steps in the heels made me sway like a woman, and with my hands behind my back my breasts jutted out like a figurehead on a ship. I licked my lips at my reflection, trying to keep my excitement down. Leena was behind me with another handful of stuff, saying how great I looked. She asked me to turn around and stay very still. She brushed something around my eyelids, and when I opened my mouth she shushed me while she concentrated. Then she applied lipstick. Again I should have stopped the whole thing, but Leena seemed so happy, and part of me was enjoying this. A large part of me. I looked at my reflection now, and someone else’s dark eyes looked out at me, and my lips were glowing red targets. I licked them again, but carefully.

Great, Leena said, breaking me away from the mirror, Now this belt. I looked at the big clunky leather belt in her hands. She shrugged and said, You have no waist. I let her fasten it on me, felt it’s tightness around my waist, and I commented that it went with the hood. She said, You know what else would work? And she lifted a bright shiny pair of handcuffs from behind her, smiling like a little girl. I had to laugh as she spun me around and snapped them on my wrists. This was getting ridiculous. She led me back to the platform, and I have to say I presented a very alluring package. Underneath it all I felt my penis stiffen, straining against the lycra tights. I glanced down at that bulge of manhood, and for some reason I felt upset that it showed, not embarrassed, but upset. Leena glanced down and said don’t worry about it. I was startled and looked at her to see if we were talking about the same thing. She reached out and smoothed the dress over my pulsing hard-on, and said, It doesn’t really show.

Suddenly the buzzer rang, signaling the arrival of the Japanese buyer. Leena jumped down off the platform and ran for the door. It would take five minutes for the freight elevator to get downstairs and bring them back up. I looked at myself, suddenly terrified at being seen this way. I looked like a woman, and more than that I looked like an ad for sex, in the tight sweater dress, my arms locked behind my back, red lips peeking out from behind the bondage hood. I felt this urge to hide, but at the same time I was proud of my silhouette, and I stood up a little straighter, there on the platform. Leena came running back in, a crooked smile on her face. What is it?, I said. She shrugged and told me that if I opened my mouth the whole illusion would fall apart, and this buyer was notorious for grilling the models on the cut and feel of the outfit. So I’ll play dumb, I said. Leena said, That might work, or…Her eyes lit up, and she was off to her office again.

A second later she was back with a black rubber ball, fit with a strap and a small circular aperture in the center. Put this on, she said, and we will play up the whole bondage angle. I looked a little skeptical, but Leena was already fitting the strap through the d-rings on the bondage hood. The gag was obviously made for the hood, and I wondered where Leena was pulling all this stuff from. Before I could ask a question, or object, it was in my mouth, the strange taste of rubber and something medicinal on my tongue. It was crafted in an oblong shape, so that my lips were spread around it in a very suggestive and obscene manner. I grunted in surprise, and realized now I was really silenced. No more objections. I tested my weight against the handcuffs. A surge of fear went through me. I was helpless, I felt a wave of anxiety build behind my eyes – but then it passed, and I felt instead a strange sense of release. The gag even tasted sweet, and I licked it tentatively. Then the doorbell rang, and I turned to look at the door.

Leena let the two Japanese men in with absolute confidence. They were young and dressed in sharp black suits, with black sunglasses. They looked surprisingly hip, compared to the image of a gray haired department store buyer that I had in my head. And then behind them came a large black woman, dressed in a tight pair of go-go pants and fishnet stockings, and a long open trenchcoat of black silk. She looked familiar, but maybe only because of all of the tall, busty models who worked for Leena. For some reason the sight of her filled me with fear, maybe the idea that another woman would look at me, dressed like this. She smiled at Leena and shrugged off her coat. Underneath she was wearing a fluffy white mohair sweater, cropped at her stomach and stretched around her ample bust. I sucked in air around the gag in surprise, and for some reason they all turned to look at me at the same time. I stood there, frozen, unable to walk. They all approached the platform together.

Leena said, Here she is. A real surprise. She gestured, waving circles with one hand, which meant I was supposed to walk the platform. I turned carefully, and imitating the models I had seen here, did a short turn down the platform, then spun and came back. I heard a soft laugh behind me and my skin suddenly burned with embarrassment. When I reached the end of the platform I stopped and looked down. The Japanese were smiling, nodding politely, and Leena looked pleased, but for some reason they all looked…carnivorous.

Well, Leena said, do we have a deal? I was confused, they had not discussed the dress at all. I looked past them at the full length mirror there. I could barely recognize myself. I tried to move the black ovoid that was gagging me, but it was wedged between my red lips. I closed my eyes carefully, feeling the weight of the mascara on my lashes, and opened them again. I was still there, dressed in the tightest of sweaters, the halo of angora fuzz surrounding my pointed breasts, my shoulders (pulled backwards by the handcuffs), even the gathered turtleneck which came almost to my chin. I felt dizzy. The Japanese and Leena were discussing something, but the words sounded garbled and far away. I shifted on my high heels. Leena gestured with her hand, and helped me to step down off the platform. One of the Japanese stepped forward and ran his hand over the dress. I shivered at his touch. The black woman laughed, she was standing off to the side, grinning wickedly. I could see through the loose weave of her sweater either a black bra, or her dark breasts showing through. The effect was very exciting, but I also felt strangely jealous. Leena was fixing something to my neck, and I heard a distinct snap. I looked in the mirror and saw a collar, as well as a leash hanging down between my breasts.

So it’s settled, Leena announced, this one for $10,000, with a buyout option of 200 thousand. I looked at her trying to make sense of what was going on. Leena smiled, and continued her sales pitch: The beauty of this slave is that he is not a willing subject, but his natural desires, to be dressed like a woman, and especially to be dressed like this, in sweaters and wool, are already overwhelming his resistance. The initial dosage will take full affect in about ten minutes, but until then you can all relish the look of fear in his lovely dark eyes. And, she laughed, you can feel his body betraying him. She reached out and stroked my hard manhood through the sweater, through the tights. I felt hot and wet down there, and uncontrollably my penis bucked at her touch.

They all laughed. The black woman stepped forward and took my leash. Her voice was deep and gravely. Don’t worry s****r, she said, we will take good care of you. Her glowing mohair covered breasts pressed against mine for an instant, and she smiled. Her lips were large and soft looking, a gentle shade of brown, but she exuded cruelty, control, domination.

Money changed hands. The Japanese exited, followed by the black woman leading me like a dog. Or a slave. I tried to scream, I tried to say something, but the gag silenced me. I tried to pull away, but the large black woman whispered what punishments awaited me if I resisted. So I surrendered, and the taste of submission, actually some chemical dripping from the gag in my mouth, was surprisingly sweet.

I would never see Leena again, but I would feel her presence around me, as I was f***ed in and out of her sweaters, her knit creations, for my new owners. Like a Barbie doll, I came with those outfits. And like a model, I loved trying them on…

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