My Girlfriend’s Sissy

For as long as I can remember I’ve played at being her. In the times I’ve been alone I’ve been Hailey and not Hal, and in all that time I’ve never been caught.

She walked in and found me, dressed up with nowhere to go. My girlfriend who saw me and in an instant understood what I needed, maybe more than I did.

She brought me out to this club. Pushed me to try and experiment. Pressed me to put myself out there and find whatever pleasure I could.

I don’t know his name but I know his body. I know his hard firmness and the press of him on me. In the darkness of this club I’m going to get to know him so much better.

I’m going to give myself to him.

Excerpt

I looked at my man nervously, blushing even harder and wondering whether I’d really have the courage to go through with this. He was so close to me and he seemed so damn big. Could I really do this with him? Could I really deal with everything that was about to happen?

Searching for a familiar face I sought out Liz and saw with shock that she wasn’t cutting any corners. She was already in his lap, straddling him and kissing him with his hands placed firmly on her ass. I watched her hips push forward, grinding against him as they kissed hard and passionately.

And there was a surge in me, not jealousy and not simple desire. Something complex and complicated, a sort of competitive streak. Something that made me want to prove to them and myself that I could do that too. That I could be every inch the woman she was.

So as my man went to say something I didn’t waste any time at all. I pushed myself up and over him, straddling his lap easily and pressing myself into his arms.

He was surprised, I could feel that in the tension of his body. But that tension melted oh too quickly as he felt me squirming and excited against him. And as it melted his hands found me, touching my hips only first but soon growing bolder and pulling me down onto him.

I responded to him, grinding myself against him and letting him touch and explore my body. I figured just so long as I kept him from getting in my panties I was perfectly fine.

Because I knew from experience that no matter how excited I got I’d stay fairly contained. An intricate trial and error process had led me to a tuck and secure method for my most masculine features that would mean that they would remain a smooth and even mound from outside of the fabric.

So I let him touch me, running up and under my skirt to grip and grab my ass, over the front of my dress to paw at my breasts. Playing with me and teasing me to the point where a heat was building in me.

A heat that made it difficult to concentrate, that meant that I was willing to take so many more risks. This was the same heat that pushed me to take clothing from my exes, that pushed me to try them on and doll me up and even come out tonight. This was the heat that told me to be a woman and embrace everything that meant.

So I did, knowing that the darkness of the club and the pounding and pressure of the music hid us just as well as if we were alone in the room I slipped to my knees in front of him and pushed my hands into his lap.

When I was straddling him I could feel how hard he was for me. Throbbing in his pants and begging for release. I knew what he needed and I knew how to give it to him.

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