I am a transvestite who does most of his cross-dressing in the closet, so to speak. When I’m not dolled up, I prefer women to men for sexual relations. The only time I have sex with a man is when I’m dressed as a woman.
Every so often, when I get really brave, I pack up my female attire and go to a motel and get a room. Then the fun begins. I put on a padded bra, a pair of silk panties with a matching garter belt, and stockings. I also put on makeup and douse myself with perfume. Then I go to a popular club and sit at the bar.
When a man approaches me, I whisper to him that I have laryngitis.
After a couple of drinks, I am looking at him in a seductive manner and batting my beautiful eyes. When he moves closer, I brush against his crotch with my hand as I look into his eyes and seductively lick my lips. This lets him know that I’m a lonely lady from out of town looking for a hot time.
Well, last Saturday night I played out this scenario and wound up in my room with Ned, a real hunk. As I fixed him a drink, I told him that I had a thing for screwing with my clothes on. I also told him that it was my time of the month but that he could fuck me in the ass. By this time, he was so hot to fuck me that he would have accepted any condition. Besides, no guy is going to turn down the opportunity to fuck an attractive woman in the ass.
Anyway, we french-kissed for a few minutes, and then I gently placed my hand on Ned’s beautiful bulge. I sensuously stroked it and then unzipped his pants and took out his cock. I continued kissing him and jacking him off. Then I started unbuttoning his shirt. I kissed him slowly, from his lips all the way down his chest, leaving lipstick smudges on his body.
When my mouth reached his throbbing penis, I delicately tongued it and kissed it. By now, Ned was ready to shoot all over my face, so I took his whole cock in my mouth. Right up to the balls I worked my moist lips up and down the hard shaft, slowly increasing the speed. When I heard him start to moan, I started licking the head of his cock, making my tongue twirl around and around the plum-shaped flesh. Then I started jacking him off with my hand. Ned moaned loudly and shot semen all over my face.
By now my asshole was really tingling, and I couldn’t wait to feel his big prick inside my ass. As Ned stroked his cock, getting it hard again, I started begging him to stuff his cock in my asshole and fill me with his hot come. He greased up his mighty rod with KY jelly and stuffed a greasy finger in my ass. I moaned in anticipation and told him how bad my asshole wanted his cock.
Ned propped me up, “doggy-style,” and pressed the tip of his cock against my asshole to tease me. Then he slowly slid his cock into my ass, filling me all up. As always, I felt so very feminine at that moment. As he started pumping in and out, thrusting deep, I felt an orgasm starting to build. My own cock was about ready to explode. I came all over the inside of my dress, all over my garter belt and stockings. I was so sticky. My body was one solid mass of pleasure.
At that point I believed that I truly was a woman. I howled with delight and begged Ned, in a delightfully feminine voice, to shove his cock deeper into my ass. As my orgasm subsided, he shot his hot load so far up my ass that I swore I could taste it in my mouth.
In the morning when I awoke, Ned was gone, but he had left a note saying he’d had a great time. I cleaned up and went home, my anus still tingling from the beautiful fucking it had gotten the night before.