A First Time Out

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.