Jake used to strut around like he owned every room. Six-foot-two, gym-built, always the loudest guy at the bar bragging about pussy. That changed the night his girlfriend Lena caught him jerking off to sissy porn on his laptop. She didnt yell. She just smiled, locked the door, and told him to strip.
From now on youre not Jake, she said, voice low and filthy. Youre my little sissy bitch. Names Jenny. Say it.
He tried to laugh it off but his dick betrayed him, rock hard. Lena made him repeat it while she shaved his legs, balls, and ass smooth. Every stroke of the razor came with her fingers teasing his hole. This holes getting trained tonight, Jenny. Real girls dont have hairy cracks.
By the time she was done, he stood in front of the mirror in nothing but pink lace panties shed bought for him. His cock strained against the fabric, a wet spot already forming. Lena snapped a photo on her phone. Proof youre a slut now.
She dressed him slow and mean: matching bra stuffed with silicone tits, garter belt, sheer stockings, and a tiny plaid skirt that barely covered his ass. Makeup came nextthick mascara, glossy pink lips, blush so he looked like a cheap whore. Every time he complained she slapped his ass hard enough to leave a handprint.
Walk for me, Jenny. Shake that sissy ass.
He wobbled on the heels she forced on him. Lena laughed, then pushed him to his knees. She hiked up her own dress, revealing she wasnt wearing panties either. Eat. And thank me for turning you into the cumdump you were born to be.
Jakeno, Jennylicked her like a starving man. Lena grabbed his wig and ground on his face until she came, soaking his makeup. Then she flipped him over the bed, yanked the panties aside, and pressed a lubed finger into his virgin hole.
Beg for it, sissy.
Please fuck my ass, he whispered, voice cracking.
Lena worked him open with two, then three fingers, scissoring him until he was panting and pushing back. She strapped on a thick black dildo, pressed the head against his rim, and shoved in deep on the first thrust. Jenny screamed into the sheets. It burned, stretched, and felt so fucking good he started leaking pre-cum onto the bed.
Lena fucked him hard, calling him every degrading name while the dildo pounded his prostate. Take it, you panty-wearing faggot. This is what you get for pretending to be a man. She reached under and stroked his cock through the lace until he came untouched, shooting ropes into the panties.
She didnt stop. She made him lick the mess out of the ruined underwear while she changed the dildo for a bigger one. Round two was slower, deeper, until Jenny was sobbing and begging to be filled again. When Lena finally pulled out, his hole stayed open, winking and empty.
Lena snapped more pictures. These go in the group chat if you ever act like a man again.
Over the next weeks the training got worse and hotter. She locked his cock in a tiny pink cage, made him wear plugs to work, and introduced him to her bull friends. The first time a real cock pushed past his lips, Jenny gagged and drooled but kept sucking like the desperate sissy hed become. Lena filmed everything.
By the end of the month Jenny was on all fours in a cheap motel, skirt flipped up, cage dripping, while two men took turns stretching his ass and feeding him load after load. Lena sat in the corner smoking, telling him exactly how low hed fallen and how much he loved it.
Jenny came again without touching his cage, hole spasming around a thick cock, mascara running down his cheeks. Lena leaned in close and whispered, Good girl. Youre never going back.
And Jenny knew she was right.