A Fantasy - Sex Stories

Late-Night Crossdresser Gangbang Bliss

I’m a juicy male crossdresser—prim and proper until I relax, then a total slut for young, fit men. One night, my straight buddy Dan, a chiselled, athletic 23-year-old woman-chaser, invited me over. He knew I was gay but had no idea I transformed into Lena—a wigged-up, mini-skirt-wearing whore with fishnets, red lipstick, and a peachy ass. I expected beers and his usual chick-chasing tales, but when he didn’t buzz me in, I fumed home, horny and ditched. Screw it—I dressed up anyway, lingerie teasing out, heels high, makeup slutty. At 3 a.m., wig on, I was set to club it. Then Dan texted, grovelling. His mates dragged him to a strip club, but now he was home, begging me over.

Hell yes. I strutted to his place, buzzed in, heart racing from four drinks. A blonde Adonis barged past me into Dan’s flat, music pumping. Four hot guys in their 20s sprawled out—two gaming, two smoking on the balcony. Dan emerged, saw me, and smirked, “Who the fuck are you?” I fluttered, “I’m Lena when I dress like this.” He laughed, “Lena, you’re hotter than the strippers! Boys, meet Lena!” Eyes turned, cocks twitched. A long-haired rocker kissed my hand with a wink, a Mediterranean stud grinned, gamers nodded.

I swayed to the kitchen, poured a drink, and danced solo, hips popping. Ready to split, I reapplied lipstick—then a gamer grabbed me. “Babe, stay,” he growled, wedging me between him and his bricklayer-hot pal. His hand grazed my knee, then rubbed. I blushed, letting it ride. He ditched the controller, stroked my back, sniffed my perfume, and pulled me in. His lips smashed mine—straight, horny, and all over me. Hands roamed my tits, bra strap down, sucking my nipples. I was soaked with lust.

Lights dimmed, porn blared, a mattress hit the floor. He shoved his cock in my mouth—I sucked like a champ, his hands pushing me deep. Then he demanded my ass. I stood, skirt up, and saw four guys watching—Dan included—stroking hard. Dan leaned in, “Lena, we’re all fucking you tonight—yes?” I nodded, trembling with need.

Five ripped studs took me—Dan and his crew pounding my ass, stuffing my mouth, treating me like their dirty girl. Two were steel-hard, relentless, fucking me raw. It was sweaty, slutty paradise. They finished, bolted, and I limped home at dawn, wrecked and grinning. Dan texted later, craving more. I’ve been back—dressed as Lena, sober—but that five-man night? A filthy, perfect memory.

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