tagTranssexuals & CrossdressersMy Girly Boy in Drag

My Girly Boy in Drag


"Hey, Rourke," I drawled as he entered the lounge, "What's up, sexy?"

"Oh,..nothing." I could tell he had been smoking weed, he had a slight hint of the scent radiating from his skin. I gazed longingly at his smooth, tan skin as he made spaghetti in the kitchen. I waited for him to finish, dropping my eyes back down to the book I had been reading.

I had wanted him since the day we'd met. He'd been wearing this cute black miniskirt with fishnets and a pink lacy top. His hair had been up in a high ponytail, and at first I thought he was a girl, if a somewhat gangly, tall one. But this was my moment. As he was cleaning up his dishes I mustered up the guts and decided just to go for it.

I walked up to him. I grabbed his hand and led him outside and into my room across the walkway. I shut the door and pinned him up against it. He looked surprised; his beautiful, brown eyes were wide and looking straight into me. I slowly closed my eyes, slipping my fingers through his hair across the back of his neck, and simultaneously our mouths met. Rapture was the softness and agility with which he skillfully maneuvered his lips across mine.

I slid my hands up his thighs, lifting and bunching his plaid black skirt as I went. I pressed my body against him, further immobilizing him. He moaned softly in the back of his throat. I undid his skirt and let it fall to the ground. He freed himself and removed his combat boots. I shoved him back up against the door. I moved my lips forcefully to his neck, reducing temporarily my passionate fervor to gentle kisses. He buckled under me and sighed. I led him onto my bed and lay him down. I slid my hands across his stomach, up across his chest, pulling the frilly black plunging V-neck off . I reached into his bra and pulled out weed, his pipe, chapstick and a lighter. I took the bra off adeptly and flung his shirt and bra off onto the floor. I slid his panties off and threw them on the floor as well. I wrestled my own clothes off and straddled him. He flipped me onto my back and looked into my eyes. I melted as he slowly lowered his body onto mine and I felt his warmth sweep over me. I slid my hands across his back and into his soft, brown ringlets that were intermingled with dreads wrapped in hemp and adorned with seashells. I wrapped my legs around his hips as he began to fuck me, nice and slow. He kissed my cheek.

"I wondered when you'd pounce me," he told me softly.

"I didn't know you wanted to be pounced by me."

"Well, I did. I was just waiting on you. I mean, c'mon Gwen. You wrote a SONG about me. Make that TWO songs."

"Meh. Well now I have you here in my Vagina." The Vagina was my bed, sitting on the floor next to my dresser under another lofted bed. It had dark red curtains draped framing the entryway. The inside of the Vagina had mirrors and little lights providing mood and atmosphere for just an occasion as this.

"Yes," he laughed. "Yes I am." He pressed his chest against my breasts as he wrapped his arms around me, the tempo of his lovemaking increasing slowly but surely.

"I really could fuck you like this all night, you know."


"Yes, really. Would you like that?"

"Only if we translate Latin together afterwards."

"A girl after my own heart!" I sighed happily. He was perfect. I glanced over at his skirt and bra on the floor and grinned. I had finally found my girly boy Classics geek.

Rourke fulfilled his promise. He made love to me all night long, making me climax over and over again, so many times that I lost count. Afterward, we sat up talking until I fell asleep on his chest. We woke up in the afternoon and did our Latin homework together, and he borrowed my black flowy skirt and a tee-shirt.

It's not that he looked like a girl. If that was what I was attracted to, I would be a lesbian. No, I liked that there was masculinity in his feminine appearance: the scruff on his face, his hairy legs with combat boots, and when he was naked....well, that was ALL man. It is difficult to explain, but I don't need to justify it to the rest of the world. I've found that perfect blend, and that's all that matters.

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