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My Voluntary First Time Crossdressing for Gay Sex — Highlights

My Voluntary First Time Crossdressing for Gay Sex — Highlights

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I had been thinking about it for months, that quiet pull that started as a late-night search and turned into something I could no longer ignore. At twenty-four I was tired of wondering. So one Thursday I ordered the things online with money I had saved from overtime: a black lace garter belt, sheer stockings, a simple black thong, and a soft camisole that would cling. When the package arrived I locked my apartment door, stripped, and took my time. The stockings whispered up my legs and the lace felt cool against my skin. I stood in front of the mirror and looked at myself, really looked. My cock was already half-hard from the anticipation alone. I felt exposed and strangely calm. This was my choice. No one was making me do it.

I met Marcus on a forum where people posted what they actually wanted instead of pretending. His messages were direct and kind. He said he liked first-timers who dressed for themselves. We talked for three weeks. I told him I wanted to keep the lights low but not off, that I wanted to feel his hands on the lace, and that I wanted him to fuck me while I was still wearing everything. He agreed without hesitation. We set a date for Friday at his place across town. I shaved carefully that afternoon, packed the lingerie in a small bag, and took the train with my heart beating so hard I could hear it.

When he opened the door he smiled like we already knew each other. He was taller than me, broad through the shoulders, with a calm way of moving that made the small apartment feel safe. We talked for maybe ten minutes on his couch, both of us sipping water, both of us clearly hard under our clothes. Then he asked if I wanted to change. I nodded. He showed me the bathroom and waited outside. I slipped into the stockings and thong first, the garter belt next, the camisole last. My cock strained against the thin lace. When I stepped out he was sitting on the edge of the bed, shirt unbuttoned. His eyes moved over me slowly and he let out a low sound that made my stomach tighten.

“Come here,” he said, voice quiet. I walked to him and stood between his knees. His hands slid up the backs of my thighs, thumbs tracing the straps of the garters. He leaned forward and pressed his mouth to the front of the thong, breathing warm through the fabric. I felt myself twitch against his lips. He hooked his fingers under the waistband and eased the thong down just enough to free me, then took me into his mouth without warning. The heat and the wet pull made my knees weaken. I held onto his shoulders while he sucked me slowly, deliberately, like he had all night. Every time I started to thrust he eased back, keeping me on the edge.

After a few minutes he stood and undressed. His cock was thick and already leaking. He reached for lube on the nightstand and told me to lie on my back on the bed. I did, legs open, stockings still clipped to the garters. He knelt between my thighs and spent a long time opening me with his fingers, one then two, crooking them until I was pushing down onto his hand and making sounds I had never made before. When he finally pressed the head of his cock against me I was shaking. He went slow, watching my face, stopping whenever I needed to breathe. The stretch burned and then melted into something deeper. Once he was all the way inside he stayed still, letting me adjust, his hands stroking the lace across my chest.

He started to move in long, steady strokes that dragged over the place inside me that made my cock jump against my stomach. The camisole rode up and he leaned down to suck one nipple through the fabric. I wrapped my legs around his waist, the nylon of the stockings sliding against his skin. Every thrust pushed a soft sound out of me. He told me I looked beautiful like this, that he loved how wet I was getting just from being fucked while dressed. The words went straight through me. I reached down and stroked myself in time with him, the lace of the thong still caught under my balls.

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We changed positions once, him on his back so I could ride. I sank down onto him slowly, hands on his chest, the garters pulling tight with every movement. The feeling of being filled while still wearing everything made me dizzy. I came first, untouched except for the friction of the camisole against my cock as I rocked. It hit hard, pulsing through me in long waves while I clenched around him. He followed a minute later, gripping my hips and pushing up deep as he spilled inside the condom. We stayed like that, breathing hard, until he eased me off and pulled me against his side.

Afterward he helped me out of the damp lingerie and brought a warm cloth. We lay there talking quietly about nothing important. I felt loose and open and strangely proud. On the train home the next morning the memory of the lace against my skin kept returning, and I knew I would do it again. Not because anyone asked me to, but because I had chosen it, every step, and it had felt exactly right.

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