A First Time Out

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A surprising first night out dressed as a girl.
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I'd always fantasized about going out to a bar or a club, dressed as a woman, and after a few drinks managed to find the courage to do so. By the end of the bottle of wine I was dressed up and ready to go, suspenders, stockings, a corset on so tight it was hard to breathe underneath a loose, knee length skirt and close fitting top. My make up was done, a touch up of lipstick after the long black wig had been smoothed down and the last of the wine polished off.

I'm always told I look gorgeous when I dress up, but I'd never been out before. Before it had just been for other people in private, but that night, well, that night I was going out.

I swear I wasn't expecting anything to happen, it just seemed to. I was so taken aback when she came onto me, her hand snaking up under the skirt, along my thigh and running her fingers over my crotch shamelessly whilst we were still in the bar. She flattered me, whispering in my ear that she loved a guy in woman's clothing and bought me another drink. I couldn't say a thing, my breath caught in my throat as I smiled nervously, my cheeks blushing furiously and found little comfort from her amused gaze at the bottom of the glass. Her fingers lightly trailed up and down my thigh and she took my hand and before I knew it we were back at hers.

She sat me down on the sofa, not letting me touch her, lightly slapping my hands as I went to run them over her gorgeous body but her hands didn't seem to know any boundaries. Despite my pathetic protests, any objections were completely undermined by the way my body responded to her touch and she ended up in between my legs, her fingers pulling my hard cock out of the panties and taking me in her mouth. As I got harder she stopped, stroking my cock with one hand, her nails scratching up and down the length of it as she smiled mischievously at me and asked if I wanted to cum in her mouth. I just nodded, unable to respond beyond that and she smiled in delight. She said my hands wandered too much and that I should keep them to myself. That she would hate to be put off what she was doing so I let her bind my hands behind my back, shuddering as the binding was pulled taut around my wrists. She moved back round after spanking my bottom with a soft laugh and took me in her mouth again. The electrifying sensation of her tongue licking at the head of my cock and balls mixed with the sharp spikes of pain as she used her teeth to nip and bite, quickly making me cum, my entire body shivering with pleasure as I filled her mouth. So lost in the feeling was I, I didn't notice what she was doing until she had straddled me, pushing me down in the seat, my arms still pinned, tied behind my back. She smiled, a sharp fingernail tracing across my cheek and line of my jaw before she leant in to kiss me. I returned it hungrily, enthusiastically until suddenly the salty taste of my own cum filled my mouth as she passed back what I had given her. In shock I tried to pull away from her kiss, but I couldn't escape and almost choked as I tried not to swallow it.

Trying to squirm beneath her just got me forced down harder into the chair, her hands either side of my head to hold it still as she forcibly kissed me, biting at my lips to get me to open my mouth. She laughed in amusement at my discomfort, not letting me move under her and lightly wiped a dribble of the cum from around my mouth, smearing it over my lips, ignoring my discomfort and pushing her fingers in when I open them to complain. She made a comment about how it was a pretty little mouth and how it should be put to use as she smiled and got off me, standing up and slipping out of her dress. She laughed as I shivered, my eyes going went wide at the sight of the cock in her own panties and not for the first time that night I found myself speechless and looking at her with an unsure, embarrassed expression.

She sat down next to me, one hand running along my thigh, up the side of my body and up the back of my neck and into my hair as the other pulled her growing cock out of the tight panties. She tightened her grip on my hair and pulled my head down into her lap roughly, her cock shoved forcibly into my mouth as I squirmed and squealed in pain and tried to get comfortable without falling off the sofa. Up and down she made my head go, making sure to get all of her cock in regardless of my choking, squirming and whimpering. Soon my whimpers were joined by her moaning and I could feel her getting bigger, harder in my mouth. She swapped hands, gripping my hair tightly with the other one as her nails ran along my skin and ended up dug savagely into my bum cheeks. Humiliation and longing washed through me as I realised my squirming suddenly wasn't to get away from probing fingers as they explored and hurt my arse but to move a little to give her better access to whatever she wanted.

I groaned, my lips still wrapped around her cock as she pushed a finger inside me and after a few moments whimpered as she pulled the finger back out and groaned herself, the head of her cock in the back of my throat. Roughly she pulled my head out of her lap and demanded that I kneel on the floor and put my head face down on the sofa seat. I went to say something but the words were cut off by the stinging slap across my face before she stood up looking expectant. After a moment's hesitation, I began to shuffle and sort my self out so I was face down into the sofa, my knees on the carpeted floor and my arse open and exposed. She didn't say anything, merely spread my legs a little with gentle strokes on the insides of my thighs and it's hard to know if my breath was catching due to fear or desire. There was a pair of quick, sharp, stinging blows, one on each of my buttocks and I yelped in surprised pain, only to be pushed back down into the sofa as she laughed and said that was for not moving quick enough.

I started to say something, finally finding my voice and I got as far as just about to start the sentence before it was stolen away again by the unexpected feeling of the head of her cock rubbing against my anus.

"Tell me you want it." she asked, her mischievous smile evident despite her controlling tone of voice. "Tell me you want it in you. Tell me and I'll be gentle."

But I couldn't, all I could manage was some sort of breathless mumbling, brought on by the fear and wanting coursing through every inch of my body. She ran her hands lightly over my bum, spreading my cheeks a little more as she said "Have it your way." before digging her nails into my hips for purchase and forcing her cock inside me. My scream was muffled by the cushion, as was the pathetic pleading, the worthless begging and moans that occasionally came out as she thrust in and out of me viciously. I don't know how long that went on for, it felt like forever but then she murmured "Good girl." in-between her own noises of pleasure and I realised I was thrusting my hips against her instead of trying to get away, to escape, and wanting more of her inside me, wanting her to cum inside me and fill me up, my own cock rock solid.

One hand slipped between my legs, her nails lightly brushing over my balls before her hand wrapped tightly around my cock. And that was it, that simple touch caused me to explode in her hand, and she moaned out loud in pleasure as she came inside me at the same time, her touch like someone pulling the trigger on a gun.

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5 Comments
AnonymousAnonymousover 9 years ago
please continue

Please continue this story. I am a CD who loves to go out all dressed up. I haven't met a TV yet but I can't wait for that night when I meet a sexy TV at a gay bar and go back to her (his ?) place. I can't wait to suck on her tits, suck her cock and then get fucked deep and hard. Please continue.

AnonymousAnonymousover 10 years ago
sissy in Ar.

Nice story, widh it would happen to me. I have been picked up and kissed by two other men and it was sweet but I need more. Please continue the story

AnonymousAnonymousabout 12 years ago
awesome story

I am so envious, i want to be taken so bad

AnonymousAnonymousabout 13 years ago
Oh Yes

I love being a transvestite and enjoy the women who like to take (and send) me out wherever they want at any time of the day in full feminine attire. These girls understand me and I am always fully body shaven, always wear lacy lingerie and have my toenails polished at all times. I would love the women in my life to introduce meet artreligis. At the end of a perfect girlie evening out, to go home to bed with her would be bliss. Would artreligis accept me as as a housemaid / sexdoll? I am willing to dress in female clothes and full make-up 24/7 for the rest of my life. Perhaps artreligis could do with me as a woman (with a mainly un-used penis)

JentvcdJentvcdabout 13 years ago
I need this done to me so bad...

I need this to happen to me so bad...

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