Freaky shemale makes a bully sorry when she has her way with his big dick

It was a balmy evening and the town’s notorious bully, Jack, was out causing trouble as usual. He swaggered down the alleyway, cackling to himself as he pushed over trash cans and hollered obscenities at passersby. Little did he know, his misogynistic ways were about to be challenged by someone unexpected – the town’s most notorious shemale, Chastity.

Chastity had been watching Jack’s antics for too long, his crude comments and lecherous looks towards her and her friends finally getting under her skin. Armed with a sexy little number and the usual ensemble of high heels, fishnets and a fishnet top, she made her way out to confront him.

Jack looked up, his eyes going wide as Chastity sashayed towards him, her large breasts bouncing with each step. “Hey there, fuckboy,” Chastity purred, licking her lips. “Don’t you know it’s not polite to stare?”

“Oh yeah? And what are you gonna do about it, bitch?” Jack sneered, puffing out his chest to look intimidating.

“Not me,” Chastity smirked, “but my big ol’ cock sure can.” With lightning speed, she grabbed Jack and pushed him up against the wall, pressing her body against his. He struggled for a moment before the heat between her legs became apparent – and large.

“W-what the fuck?!” Jack choked out, eyes bulging in shock and something dangerously close to arousal. “You’re fucking sick!”

“I’m not the sick one, I’m just here to teach you a lesson about respect,” Chastity said, nimble fingers already working on his belt. “Now, be a good boy and let me show you what else this hot body can do.”

Gagging slightly as Chastity shoved her huge bulge against his face, Jack was at a loss for words. Chastity laughed, leaning in to whisper in his ear. “I’m gonna fuck that bratty look right off your face, I promise. By the time I’m done with you, you’ll be screaming my name and begging for more.”

Shaking and sweating, Jack let out a squeak of protest as Chastity’s manhood sprang free from her panties, hard and throbbing. She hoisted him up, pinning him to the wall as she lined herself up with his quivering ass.

“You ready to take it like a man, or like the little bitch you really are?” Chastity teased, the threat of her thick cock pressed against his entrance.

“P-please,” Jack whimpered, “Don’t – I’ll be good, I’ll stop, j-just don’t hurt me!”

Chastity laughed again, that heady masculine scent making his knees weak. “Oh, I’ll give you what you need, baby boy.” Without another word, Chastity drove her hips forward, pushing her thick manhood deep into Jack’s hole.

Jack screamed, the sudden intrusion surprising him. But as Chastity settled in, rocking her hips to work her huge cock deeper, the pain started to give way to a numbing pressure – and the first, traitorous spark of pleasure. “Shh, just relax,” Chastity purred, one hand moving down to rub circles on Jack’s belly. “Let me make you feel good, stud. Show you what a real man feels like.”

Groaning brokenly as Chastity’s girthy cock stretched him open, Jack found himself slowly relenting, giving in to the deep, shuddering pleasure. Chastity could feel him starting to loosen up, his hole starting to welcome her. “That’s it,” she cooed, “Ride my cock, baby. Milk me for all you’re worth.”

Jack felt drunk on lust, his mind hazing over as Chastity started to pick up the pace. The wet slide of her cock in his ass sounded obscene in the empty alley, each thrust of her hips forcing grunts and whimpers from his lips. “Fuck, fuck, fuck,” Jack chanted mindlessly, fingernails clawing at Chastity’s back as ecstasy overtook him.

Chastity grinned. She had him right where she wanted him. Giving a final, rough thrust, she pushed Jack right over the edge, his trembling asshole clenching deliciously around her cock as he came untouched. “See what happens when you misbehave, baby?” Chastity teased, giving a few last rolls of her hips for good measure.

Jack could only whimper in response, spent and dazed. Gauntlet thrown, Chastity pulled out – giving Jack’s hole a little slap for emphasis – and sauntered off into the night, a satisfied smirk on her beautiful face.

Sure, Jack was still a piece of shit, but he’d learned his lesson about respect – even if it ended up coming from the most unexpected of places. And Chastity? Well, she was content knowing that the next time Jack thought about being nasty, he’d remember this night under her skirts instead.