The Date

By T IM

Published on Jul 31, 2007

Transgender

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Steve is an average looking, smallish guy with long hair pulled back into a ponytail. Most people wouldn't give him a second glance. He's shown me pictures, though. With make-up and the right clothes, he transforms into Sylvia. Sylvia is stunning. I begged and begged Steve for a date with Sylvia. Finally, he agreed.

I picked hir up. S/he was lovely in a grey blouse and black skirt, black hose and pumps. We started with dinner, and then a comedy movie. We held hands as we walked back to my car. I stole a kiss before starting the motor and driving back to Sylvia's apartment. I stole another kiss at the door. S/he invited me in. We sat on the couch, kissing slowly. Our mouths opened and our tongues slithered out. We made out feverishly. Sometimes I could feel a bulge through hir skirt, and that excited me. I reached up to squeeze hir breasts, even though I knew they were just padding. I puledl hir collar aside and put a hickey at the base of hir neck. Hir hand was in my lap, rubbing my cock through my pants. I reached over and fondled hir bulge. S/he unbottoned my shirt, and began sucking my nipples. Somehow s/he knew that I love that. S/he kissed down my chest and stomach before opening my slacks and taking out my cock. Hir mouth took it in, leaving lipstick on the shaft, S/he rolled my balls between hir perfectly manicured fingers. S/he looked so beautiful, so sexy. I knew I wouldn't last long. "Sylvia!!" I gasped as I came. S/he gulped down most of my load, saving a little in hir mouth. Stroking my softening, dripping cock, s/he kissed me, letting me taste my sperm.

I reached under hir skirt and slid hir panties down. Lifting the skirt, I lowered my head to hir lap, kissing hir erect cock, then licking it with broad strokes, before letting hir slide into my mouth. I bobbed my head, listening to hir moan. Wetting a finger, I wiggled it into hir backdoor. S/he squealed, and pushed down on my head. I sucked and fingered hir faster. "I'm going to cum, baby!" s/he panted. I sucked deep and let hir explode in my mouth. I kiseds her, sharing cum with her.

"Baby, will you fuck me?" s/he asked.

Sylvia lay on hir back, rubbing lube on hir tight hole. S/he lifted her legs, placing them on my shoulders. I moved hir ballsack aside and pressed my cockhead to the hir rosebud. I pushed gently. Then a little harder. Then I thrust firmly. Sylvia cried out, hir pucker opened and accepted me, and I was inside hir. I waited, letting hir muscles relax. S/he nodded, then, and I started to pump slowly, in and out. I watch hir pretty face as I took hir ass. Her hands wentto my chest, her thumbs brushing my nipples. I fucked faster, wanting hir, needing hir. I caught hir cock in my hand, jacking it. My cock head bumped hir prostate with every thrust. I felt my orgasm building. I grunted and I filled hir backhole with my love suds. S/he came seconds later, shooting all over my stomach and chest , and hir own belly, and even onto hir nice clothes. I fell on hir, kissing hir. "Oh Sylvia!" I whispered.

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