Tomboy: Turnabout (Chapter 5) (Patreon)

Tomboy: Turnabout

Chapter 5

“You know the drill, Kelly,” Jessica purred, dangling an open collar in front of her upturned face.

A tear rolled out of each eye, leaving a wet trail down her flushed cheeks. Kelly nodded, throat too tight to speak. She lifted her chin when Jessica tapped it. Brad gathered up all of her long, blonde hair and lifted it back out of the way. The brunette slowly wrapped the black leather, silver studded collar around the blonde’s slender neck, and buckled it snuggly in place.

Jessica untied Kelly’s legs, while Brad released her arms. Kelly was finally able to stand, taking a moment to stretch aching, taut muscles. Then her mistress handed her a pair of black thigh-high stockings. She pulled those on, and then put on the garter belt to hold them up. The blonde was given the tiniest of micro miniskirts, which was white and flouncy. That was followed by a white bikini top that barely contained her tits, but it required the nipple clamps finally be removed. After Kelly put on a pair of lacy white, fingerless over-the-elbow gloves, Jessica made her put on a pair of black patent thigh boots.

Kelly stood straight before Jessica and Brad, who circled her touching, squeezing, and tugging on her body and clothes.

“Totally fuckable,” Jessica teased, looking so pleased. “And, wow, how you’re going to be fucked.”

The busty blonde turned sad, pleading eyes to her longtime rival.

“Please don’t do this to me again,” she begged. “You owned me last summer. You had your way with me. You gave me to everybody in our graduating class, for the love of God. Can’t we just move on?”

“Aw, you are so adorable,” she said. “But we both know I own you even more profoundly now. Not just for the summer, either. And if you are thinking of misbehaving, just think about all of the very bad men who’d love to get their hands on Tomboy. How they’d love to get their pound of flesh.” Jessica’s hand snaked up under Kelly’s skirt. She stroked the blonde’s hot, slick pussy with a long-nailed finger. “Think about how much they’d love to get their pound of pussy flesh out of you.”

“Hold her tight, Brad.”

He pressed up behind Kelly, grabbed her arms, and pulled them back. That forced Kelly to bow her back, thrusting out her tits. The brunette then pushed Kelly’s bikini top up off her tits.

Jessica retrieved a small case from the chest of drawers, opened it on the bed, and pulled out a large needle. A piercing needle. Kelly’s jaw dropped when the brunette quickly pulled on her left nipple, pierced it, and then did the same to the right.

“Oh my God,” Kelly gasped. “What is wrong with you?!”

“So much. I really don’t have time to go into it all,” Jessica taunted. Then she pulled two silver items out of the case. Dumbbell nipple studs. She quickly inserted one through each piercing.

“Ta da! Titty jewelry.”

Jessica stepped back to admire her handiwork. Kelly teetered atop her stilettos, mind in chaos. Jessica was really pushing it this time. It did not bode well for her fate.

“Kneel. Kiss and lick my pretty little shoe.”

Jessica slid her right foot forward. Kelly stared at it as second, then Brad released her arms and pushed down on her shoulders. The hapless blonde rolled her eyes, but dropped to her knees, then rolled forward to all fours.

Kelly lowered trembling lips to the pointy toe of that expensive Christian Louboutin pump and gave it a little kiss. Then she started kissing and licking from the toe to the tall stiletto heel, all while her hands fondled the shoe and Jessica’s nylon sheathed ankle. She rolled her tongue around the stiletto heel, stroking it up and down like that. Yeah, the previous summer Jessica trained Kelly quite extensively on licking stiletto-sheathed feet.

She expected Brad would take the opportunity to either eat out her pussy, or fuck her doggie style. Yet, he did nothing. The two of them just watched her debasing herself by kissing and licking.

“Awesome, Kel,” Jessica purred. “I love how you haven’t forgotten your slave girl training. You are amazing.”

Kelly sat back on her legs, looking up with sullen eyes.

“You’re lucky, Kel. None of our friends are in town anymore,” Jessica said. “So I can’t whore you out to them.”

“That’s good.”

“No, that’s bad,” Jessica said, a look of evil glee spreading across her face. “That means I have to find new, even more disgusting and/or depraved men to fuck you.”

“Good times,” Brad sneered into her ear. “I’m depraved man numero uno.”

“Yes you are,” Kelly said.

Jessica snickered, and then attached a leash to Kelly’s collar. She gave it a little tug, turned, and strode away. Kelly followed obediently. Heeling, as it was called in the BDSM community. Heeling like a well-trained dog. So demeaning.

The shapely nineteen year old was led out of the pool house, around the side of the main house, and to Jessica’s BMW convertible. Brad jumped behind the wheel, while Kelly had to join Jessica in the back seat. The brunette’s hands were all over her body before the car was even started. Soon, Jessica claimed Kelly’s lips and it started in earnest.

The two teens made out like horny minxes in the backseat. Brad drove them through the night-shadowed streets, down to the river. Kelly rubbed her tingling lips together, looking all around with big eyes. It was a scary place, so dark and ominous.

They parked in a dark alley between two turn of the century buildings. Most of the windows were broken. No lights. Everything looked abandoned. Of course, Jessica practically bounced out of the car, so excited. She could barely contain her enthusiasm.

“Come, come, slave,” she urged Kelly. “The party is about to start.”

“Party? Is it some kind of rave or something?”

“Or something,” Brad said, and barked a laugh.

Jessica and Brad put on masks. Kelly’s heart rate soared. Why did they need to wear masks? What was about to happen? Who were they meeting?

They wore the cheapest of cheap plastic Halloween masks with elastic strings holding them in place. And then Jessica gave another tug on the leash, before striding purposely to a closed door. Brad rushed ahead and opened it for them, and the women clattered inside to be plunged into darkness.

Not complete darkness. Kelly’s eyes were pulled toward the source of light. Firelight. Fires burned in three steel drums. Men stood around eating, drinking, speaking. All eyes turned toward the newcomers.

“Hello, boys,” Jessica called in a seductive voice. “Do you want to party with us?”

“What do you mean by party, Miss?” an elderly homeless man asked.

“And you are, sir?”

“Otto.”

Kelly looked Otto up and down in the dim light. He was tall, white, maybe a hundred fucking years old. He only had three teeth left up front, one upper, two lower. His beard was as long as his hair, tangled and greasy looking. He wore a tattered blue suit.

“I’m Mistress Lexy,” Jessica said. She indicated Brad. “This is my man servant. I haven’t given him a name yet.” She smiled at the dumbstruck homeless man. “And the hot little blonde slavegirl is Kelly. Poor Kelly is so young, so nubile, so damned horny. Honestly, I am beside myself trying to keep her libido satisfied. I’m desperate, Otto. Can you and your friends help us help Kelly? I promise, you’ll enjoy the experience, too.”

“She looks more scared than horny.”

“Kelly?” Jessica asked, giving her a warning look.

“I get… I get off being scared, Master Otto,” Kelly stammered. “I am dying I’m so horny. Please help me.”

“And how can they help you, Kelly?” Jessica asked, sounding so sincere and innocent.

“B-By fucking me,” Kelly whispered, dropping her eyes. “I need to be fucked by…” She looked up at Otto, then past him at all the other attentive homeless men. “I need to be fucked by all of you. Please.”

“Your begging still needs some work,” Jessica said. She removed the leash. “All fours. Grovel. Beg. Show these fine men just how much you need them.”

Kelly looked up at her in horror for a second, then swallowed the lump in her throat. Then she nodded, dropped to all fours, and crawled up to Otto.

“Master, I hunger. I need so much,” she whispered. Kelly reached up to stroke his crotch. His cock started to swell. “Please, I’ll explode if you don’t fuck me. I’m just a dirty little slut. I have such need. A need to please big, strong men like you. Please fuck me, Master Otto.”

One of the other men groaned, another growled softly. Kelly started crawling towards them. She licked her lips, ran her tongue across her teeth. Anything to excite them.

“I’m just a little lost slave girl,” Kelly said, almost choking on the words as she watched men grabbing their aching crotches. “So lost and helpless. I need a big daddy to take good care of me. I need my daddy to make me scream. Make my body sing. Will you guys be my daddies?”

Jessica rushed past her. “See her need, boys? Don’t you want to make our little Kelly happy? Don’t you want to make her come so hard her brain melts?”

The brunette pointed at a large black man. Kelly guessed him in his twenties. Already a casualty of society, living on the streets. Jessica got him to strip and lay on his back. She waved Kelly over, who had to crawl atop him and straddle his hips.

“Hi, I’m Charles,” he said, even as he started fondling Kelly’s tits. “You are so beautiful.”

“What are you waiting for, slave?” Jessica asked.

“Nothing, Mistress,” Kelly whispered, reaching down between her legs. She wrapped long, delicate fingers around his massive erection and guided him to her entrance. Once he was firmly ensconced in her slippery folds, right at her entrance, Kelly thrust her hips and impaled herself on his meat. “Ugggggh! Oooooh.”

Charles spread her little hole out so wide, so well, so wonderfully. Kelly hated how much she loved it. Why did sex have to feel so amazing? Jessica would just use it against her in the most insidious ways.

“Otto, how would you like to take Miss Kelly up the ass?” Jessica asked.

Kelly slanted a worried look back over her shoulder. The old man came toward her, his ravaged face a mask of lust and desire. And two more homeless guys pressed up to either side of her. She looked up with big eyes, and they grinned back down at her.

“I’m Al.”

“Hi, I’m Bailey. You got the prettiest lips.”

So creepy!She thought, but smiled and wrapped her hands around the two homeless men’s dicks. Kelly started stroking them, turning to first Al to suck on his cock. That’s when Otto pressed up close and personal behind her, fingered her asshole, and then fondled her ass.

Jessica produced a tube of lube, slathered Otto’s erection, and then Kelly’s butt hole. Kelly felt gratitude for that courtesy, despite everything.

“Ugggggh. Oh! Oh!” Kelly gasped when Otto penetrated, quickly getting well mounted. And then he started reaming her out with abandon. “Ooooh, baby.”

She turned to Bailey and wrapped her lips around his cock. And for the next few minutes Kelly turned back and forth, taking turns sucking their cocks, while Charles and Otto double-penetrated her down below.

Those four homeless men quickly turned her insides into a hot mess, and had her body singing despite her misgivings. Kelly wiggled and bucked, she gasped, groaned, and moaned wantonly. She gave them all they ever wanted, and then some. And as she felt that rush to climax building, Charles sheathed himself balls deep and flooded her womb.

“Aaaaaggh,” she screamed her climax around Bailey’s cock, and was rewarded with a mouthful of cum. “Mmmmmm.”

Otto creamed her ass next, followed quickly by Al coming all over her face and tits.

“Who wants to be next?” Jessica asked.