First Time as Sissy

I'd had fantasies for years on and off about crossdressing, but I'd written them off as the same kind of fleeting idea like going to the moon, or racing formula one. I'm straight, I like women, but I also like pleasure and don't understand why some things are taboo even if they feel good. But those thoughts are best kept to oneself, at least they were where I grew up.

I was surfing the net one day and came across a local site for a dominatrix who advertised as being more at the erotic pleasure end of the spectrum, as opposed to the tie you up on the rack with clamps on your nipples and smack you with a table tennis paddle. I was intrigued.

I made a call, and a few days later I was nervously having a shower while she laid out some clothes for me to wear. I was honestly wondering if I could go through with it, and thinking what would people say if they could see me doing this. Well you might find out... I went out into her dungeon, and she was wearing a sexy tight corset, displaying her beautiful and busty cleavage, and with a mischievous smile and a naughty twinkle in her eye. I knew in that moment that even though I was afraid (yes that's the right word), that I was in the right hands, so to speak.

"Which outfit do you like best" she asked as she made me walk stark naked in front of a table laid out with leather, lace, and all other assorted garments. Oh, and on the walls and racks behind were more clothes, and assorted dildos, masks and other things I'd only ever seen in fetish porn or my imagination.

"This one mistress" I squeaked as I pointed to a purple PVC dress with laced up fuck-me boots.

"Oh, you're one of those are you" you she giggled with delight. "That's a new purchase, and I think it'll fit you perfectly."

She was right, it did -after she fitted the fake breasts and before she applied some bright red lipstick, makeup, and a Mia Wallace wig straight out of Pulp Fiction.

"Look in the mirror" she commanded. I must point out that even though she commanded me, it was with erotic understanding of what I was going through, and felt like she was giving just the right amount of assertion that I needed.

"Wow" I muttered as I awkwardly walked toward the mirror on the 5 inch heels. By the time she told me to feel the clothes I'd already started rubbing my hands up the dress and was caressing my new-found tits, swaying my hips and looking in my eyes in the full-wall mirror and basically finding myself wanting to fuck me.

"Walk around the room" she instructed, adding that I had to do some twirls on the stripper poles positioned in strategic spots. The first twirl was shaky, the second was not great but tried hard, but by the time I got to the third I'd given up worrying and was in the moment. I lifted my right hand high, brought my left knee up to my midriff and gave a spin that for a moment made me feel like I was on stage with a room full of horny people watching and cheering.

After a few more lessons on how to walk and hold myself I was then given a challenge. I had to achieve an 8 out of 10 or more to progress. "An 8 out of 10 mistress?" I innocently asked, as she turned around wearing a thick black strap-on cock.

"Suck my cock sissy" she commanded, "and make it wet and noisy."

So here was this (admittedly fake) cock, attached to this goddess clad in a leather corset with beautiful eyes telling me to do this. I lowered my mouth gently, licking around the head as I like having done to me, then briefly taking the glans in my mouth and out again.

"That's really good" she said, "now get in down your mouth, I want to hear wetness" she commanded.

I went to work on that fake rubber cock. I could feel the fake veins on my lips, and she was thrusting in and out of my mouth. A moan escaped my lips, and I sealed it by lowering my head and taking it deep in my throat. I was almost going to be sick until I remembered something I'd heard years ago that I once told a girlfriend - if you smile it reduces the gag reflex. Well it worked, and by the time I surfaced she told me that I'd passed. Just. But she wasn't happy, and I needed to make up for it.

I was told to lie down on the table, and lift my knees in the air. She positioned herself at the end of the table, applied a dollop of lube to the thick black cock between her legs, and slowly pressed it between my butt cheeks.

"Relax and breath" she told me in that commanding but sexy and caring voice. I tried as she inched it into my nervously waiting body. "It might hurt in a minute" she said just as the large head at the top of her shaft penetrated my arse and I was briefly in a contradictory world of pain and intense pleasure, wanting it to stop but craving it to go deeper and harder.

"How's that my little sissy slut" she asked. I couldn't say much except that it felt so good. She started rubbing my rock-hard cock as she slid hers in and out of me. I was in heaven, my cock being expertly handled, with a rock-hard cock in my arse and a busty beautiful woman looking in my made-up eyes clearly enjoying the pleasure she was dishing out to me.

I couldn't handle it much longer. "I think I'm going to come mistress" I said. She immediately stopped and said "no sissy, you can't come until you tell me what you want me to do."

I assumed she wanted me to tell her that I wanted her to fuck me harder. And that's what I meant to do. But for some reason I blurted out in the heat of the moment "come in my arse mistress."

I think it's a fair bet that she's seen a few men come before, because she thrust harder and harder, moaned, shuddered, lent forward and if I felt some warm jizz in my arse I would have sworn she had just come out of that thick black rubber cock. My own cock exploded and I felt my hot come hit my upper arm, and then pumping up more and more sticky come onto my body-stocking clad stomach.

"Wow, that's a lot of come," she said as she slowly pulled out of me.

"Wow" I replied in turn. "That's because that's one of the hottest things that's ever happened to me. You are amazing."

She sat down and we talked as I lay there wearing PVC, stockings, wig and makeup, and I felt completely at ease with her and what had just happened.

I left with a huge satisfied smile. That was a couple of months ago and I've had another session since which was equally amazing. Right now though I'm a little worried, but if I'm honest I'm also extremely excited. She got in touch and has organised a session where she's going to, in her words "bring in other people and tell me what to do, and let them use you." Where is this going to lead? I'm afraid I'm going to enjoy this far too much... I might even write and let you know how it went.

This story was very much based on real life events. Wish me luck, I might let you know what happens next.