I never thought I'd actually go through with it. All those nights scrolling through forums, staring at pictures of guys in panties getting railed, wondering what it would feel like to be the one bent over and used. I'm 24, slim, smooth from shaving everything below the neck, and I've been dressing up alone for years. But tonight was different. I put on the black lace thong, thigh-high stockings, a short skirt, and a tight top that pushed what little chest I had together. My makeup was slutty, lips glossy pink, eyes lined dark. I met him online, a thick-built guy named Marcus who said he liked breaking in nervous sissies like me. We agreed to meet at his place, no names, no bullshit, just raw fucking.
When I knocked on his door my hands shook. He opened it, looked me up and down, and smirked. "You came dressed like a proper little whore," he said, pulling me inside. The door clicked shut and he didn't waste time. His hands grabbed my ass, squeezing hard through the skirt. "You ever had a real cock before, sissyboy?" I shook my head, voice catching. "First time," I whispered. That made him grin wider. He shoved me against the wall and kissed me rough, tongue forcing its way in while his hand reached under my skirt and cupped my cage. I'd locked myself up earlier so there was no chance of getting hard like a man. Only the ache of denial.
Marcus didn't tease long. He pushed me to my knees right there in the hallway. I fumbled with his belt, heart pounding, and pulled out his cock. It was thick, veiny, already half-hard and bigger than anything I'd practiced on with toys. The smell hit me first, musky and male. "Open up," he ordered. I did, lips parting, and he fed the head into my mouth. It tasted salty, skin hot and smooth. I gagged when he pushed deeper on the first thrust, spit already dripping down my chin. He grabbed my hair and fucked my face slow at first, letting me adjust, then faster. "That's it, suck it like the sissy you are." My eyes watered, mascara probably running, but I kept going, tongue swirling under the shaft the way I'd seen in videos.
After a few minutes he hauled me up and marched me to the bedroom. He bent me over the edge of the bed, flipped my skirt up, and yanked the thong aside. Lube was cold when he squirted it between my cheeks. One finger pushed in first, then two, stretching the hole I'd only ever fingered myself. It burned, but the burn turned into something hotter when he curled them against my prostate. I moaned, pushing back. "Greedy little hole," he laughed. Then I felt the blunt head of his cock pressing there. "Ready to lose that cherry?"
I nodded, face buried in the sheets. He didn't go slow. One hard shove and he was inside, splitting me open. The stretch was intense, pain mixing with this deep, filthy fullness I'd never felt. I cried out but he held my hips and kept pushing until his balls rested against me. "Fuck, you're tight," he grunted. Then he started thrusting. Long, deep strokes that dragged over every nerve. My caged cock leaked steadily into the thong, useless and dripping. Each time he bottomed out I saw stars. He reached around and slapped my ass hard, leaving handprints while he pounded me.
Marcus flipped me onto my back after a while, legs pushed up to my chest. The new angle hit even deeper. I watched his cock disappear into me, shiny with lube and my own spit from earlier. "Tell me how it feels," he demanded. "Feels so fucking good," I gasped. "Don't stop." He didn't. He fucked me like he owned me, sweat dripping onto my stomach, balls slapping my ass. When he got close he pulled out, ripped the condom off, and stroked himself over my face. Thick ropes of cum landed on my lips, tongue, and cheeks. I licked what I could reach, tasting him, swallowing like the sissy slut I'd always wanted to be.
He wasn't done with me yet. After a short break he made me ride him, my stockings still on, skirt hiked up.
I sank down on his cock again, learning how to move my hips, grinding when it felt best. My own denied orgasm built in waves but never broke because of the cage. That frustration only made every thrust more intense. He came inside me the second time, filling the condom deep while I shook on top of him.
We lay there afterward, his cum leaking out of me when he finally pulled free. I felt wrecked, used, and strangely complete. Marcus gave my ass one last pat. "You'll be back," he said. I already knew he was right. My first time as a sissyboy taking real cock had turned me into exactly what I'd fantasized about.
