Cassidy Makes Him a Bitch

It was a long night. They rarely got together anymore, as was all too common amongst newly graduated college-friends. So, on such occasions where the stars aligned and eight busy technically-adults were able to get together, they tried to make every second count. Two members of the group had to leave, regretfully of course, just around midnight. They both worked the morning shift, and so cut themselves off after one or two beers. The rest of the group felt no need to restrain themselves. Drinking game after drinking game was played, each one trying less and less hard to disguise the true objective of getting absolutely fucking hammered. The group bled members as the night continued. A few people passed out after the third round of stack cup. Another fell asleep in their pajamas while everyone watched "The Fly". A few more had to tap out after the final round of tequila shots. Finally, at 3:00AM, there remained only one person left conscious.

Her name was Cassidy, and she was stone cold sober.

While the others were making mixed drinks that could only be described as flammable, she was sipping on seltzer water. If her friends hadn't been so busying pouring vodka shots down their throats, they might have noticed that hers were going down the sink drain. She played the part well enough; laughing too hard at unfunny jokes, wobbling when she stood up, even slurring her words a little. But truth be told, she had less than a thimble full of liquor over the course of the night. Normally, she would drink the rest of them under the table without a second thought. She was the largest out of the group, dwarfing even the men by several inches and a dozen pounds, and so naturally had the highest alcohol tolerance. She would normally take great joy in lording her size over the others, be it stealing a friend's drink and holding it out of reach over their heads, or wrestling a man to the ground and mocking him for losing to a girl. But tonight was different. There were no games, no horseplay, no drinking. No, tonight, Cassidy had a goal.

She was going to make him her bitch.

His name was Tom, and he had royally fucked up. You see, he used to be her boyfriend. They only dated for a month or so back in college before deciding they'd be better off as friends. Or at least, he had decided that. Tom was shy, a sweetheart, the kind of guy that didn't speak up if the waiter brought him the wrong meal. Cassidy was loud, confident, with the kind of extroverted charisma that Tom found equal parts charming and abrasive. He was drawn to her, at first, probably because she scared him a little. And she was drawn to him, probably because she liked men who scare easily. At first, all was well. There was certainly a mutual attraction between them, and despite having opposite dispositions, they got along well enough.

The problems began to arise once they started taking things to the bedroom. Cassidy was, in a word, dominant. She liked overpowering people, making them feel helpless, humiliating them until there were tears in her eyes. Simply put, vulnerability got her off, and being as large and strong as she was, it was easy to exploit that vulnerability. Tom wasn't spared any of that treatment; at 5'5" he was substantially shorter than her, and only half as strong. The first time they had sex, he expected it to go normally: There would be some light foreplay, she would blush chastely as he gently took off her pants, then missionary for three minutes and they could call it a day.

So, you can imagine his surprise when Cassidy slapped him across the face, ripped off his clothing, and threw him onto the bed. He barely had time to sneak in a word of protest before she was pinning his ankles to his ears.

"Shut the fuck up, slut."

That was all she said, before sliding him into her and fucking him amazon style until his eyes rolled back into his head. He must have came three times, his hypersensitive cock constantly under assault, begging her to stop through gasps and moans. But she didn't stop pounding her hips into him until she was satisfied, until there were tears streaming down his face and drool dripping from his mouth. She mocked him all the while, calling him pathetic, telling him he moaned like a little bitch, daring him to try and escape while knowing full well that he stood no chance of overpowering her.

They only had sex one more time after that, and it went much the same. A week or two later, Tom meekly broke the news: He liked her and all, but...things just weren't working out, you know? They still had all the same friends (the very people drunkenly passed out around them now), so they could still hang out, but he felt that they just weren't compatible. He didn't say: Cassidy, I'm breaking up with you because you routinely shatter my masculinity through violent sexual humiliation, but he didn't need to. That much was implied by the deep crimson on his cheeks as he dumped her.

She took the rejection well, at least on the surface, and played nice for the rest of college. They hung out, they studied, the friend group didn't have to "pick sides". Tom was hesitant at first, worried that she'd hold some kind of grudge, but eventually the two regained the sort of easy banter that made them friends in the first place. He assumed that she'd moved on, gotten over him; that she agreed they should just be friends.

But he was wrong.

You see, Cassidy had a particularly strict stance when it came to her sexual partners. In her mind, once she had topped a boy, he was hers now. Especially if she totally and completely dominated them in the way she had with Tom. He was really going to cry and beg one moment, completely submissive and at her mercy, then ask for a breakup the next? As if little bitches got to decide things for themselves? No, that wouldn't do at all. The second he invited her into his bedroom, he had made a choice. He was hers now, whether he knew it or not.

She just had to remind him of that fact.

And so, she had planned, and waited, and schemed. And it was all coming to a head tonight. She walked into the living room, lit only by the gentle blue light of tv screen. Four of her friends lay sprawled in various places around the room, in sleeping bags on the floor, on the love seat, cuddled up on the couch. She ignored them, tip-toeing past to reach her prey. Tom lay by himself on a small couch, covered only by a thin blanket that was falling off onto the ground. She hungrily ran her eyes over him. He was sound asleep, deep into a drunken slumber. He had stripped himself down to his boxers, leaving most of body exposed. One arm reached behind his head, while the other dangled off the side of the couch, his fingers brushing the floor.

Cassidy could feel herself getting wet already. Just the sight of him there, helpless, completely unaware of what was about to happen, was enough to get her blood pumping. She sat down softly near his waist, careful not to disturb him. She traced a single finger down the length of his torso, dragging her long nails from collar bone down to his waist. He twitched a little when she passed over his nipple, but other than that he remained completely still.

"Perfect." She whispered, smiling at how well her plan had worked.

Her hands snaked down below his waist, gently prying open the front of his boxers. Slipping one hand in, she slowly pulled out his flaccid cock. Tom's legs moved a bit in response to the intrusion.

"Shhh. That's it, bitch." Cassidy cooed in response. She took the head of his penis in one hand, slowly rubbing the underside with her thumb. Tom let out a soft moan.

"You're mine." Still fast asleep, his dick began to grow. She stroked it harder now, adding three fingers to the top of his shaft, rubbing up and down with increasing speed. He let out another soft moan, and his slender frame began to stir. Realizing her window was closing, she sped up once more, taking his cock in her hand. He was fully erect now, and she firmly pumped up in down, once, twice, three times. The boy's hips began to buck slightly, his own unconscious body betraying him as the feelings of lust took over. She could tell he was getting close, so she sped up again, gently caressing his balls with her free hand.

He started to moan more loudly now, that slutty, girly moan that Cassidy loved to mock him for. His hips flexed into the air, and his legs twitched and tensed in rhythm with her strokes. She could tell he was getting close. Bending forward, she ran her tongue over his cock head. This new sensation caused his eyes to snap open. A look of confusion washed over Tom's face; he was startled, totally thrown of guard by being woken up in the middle of a sex act. He looked down at Cassidy, then to his now aching cock, then back to Cassidy with an expression of shock and disgust--

--that Cassidy simply craved. She immediately clamped a hand onto his mouth, stifling the cry of protest that was gathering there. Her other hand remained firmly on the shaft of his cock, continuing to pump up and down even as his hips struggled against her. She moved onto them, straddling him and easily pinning him in place with her superior strength.

"Keep your fucking mouth shut, whore. You don't want to wake the other's, do you?" She whispered, a look of malicious glee in her eye. "Unless...you want that? Is that it, you pathetic little girl? You want your friends to see you get treated like a little bitch? To see how much of a slut you are?"

Tom's eye went wide. The thought of his friends seeming him like this terrified him. What would they think of him if they saw him being man handled, forced to submit against his will? Cassidy saw that fear, and knew she had him.

"Are you gonna behave?" She said through a gleeful smile, "Or do I need to wake up the peanut gallery?" He hesitated a moment, considering putting up a fight...but he knew it was hopeless. She was too strong, and he couldn't risk being seen like this. Reluctantly, he gave a small nod. "Good boy." She replied, before returning her tongue to his cock head, swirling it around and around. A gasp escaped his lips, muffled by Cassidy's hand. In response, she moved her hand to his throat, lightly squeezing around the sides.

"Better be quiet, Tom. James is a light sleeper." She teased, "If you wake him up, I'm gonna ask him to join us." She gave his shaft another hard pump. "You'd like that, wouldn't you? Fucking pervert. I bet you'd secretly love to get dominated by another man. Maybe I'll wake him up on purpose."

"P-please, no-" Tom whispered in response. Cassidy tightened her grip on his throat, cutting him off.

"Or maybe I'll wake up Paige? I know she thinks you're cute. I hear you two went on a date last week. Tell me, slut, will there be a second one if she finds out what a little bitch you are? I bet not." She pumped his shaft again, slowing twisting her fingers around the head. His dick was twitching now, and she could tell he was close. She kept him on the edge, twirling his cock between her index finger and thumb, not applying enough pressure to make him cum. "Once you see a man getting held down and fucked like a little girl, it's hard to see them as anything other than a bottom."

Despite his fear and revulsion, Tom found himself to be hopelessly aroused by Cassidy's taunts. He didn't want to be humiliated in front of his friends, to be dominated by a man, to be reduced to nothing in the eyes of his crush, but...the shame he felt at each prospect was a powerful aphrodisiac. There was a part of him that did want to feel small, inferior, and defeated; that reveled in having his agency violated without any hope of escape. Cassidy had a gift for identifying, and exploiting, this weakness in men. She knew that if you brought them low enough, making them feel the worst kind of humiliation and mental pain, then you could break them. And once you break them, you can make them your bitch forever. All she had to do now was finish the job.

It only took one more firm pump for Tom to finally blow his load. As soon as he began to orgasm, she removed her hand from his shaft and pinned both his wrists above his head, denying him any chance at real pleasure. His hips thrusted at the air desperately as his balls emptied onto his own chest and stomach, covering him in thick white globs. Cassidy maneuvered her own body just out of reach of his aching cock, allowing him no contact but the air between them. Tiny, pathetic moans began escaping his mouth, and he had to bite down hard on his bottom lip to keep himself quiet. Cassidy relished the look of desperation in his eyes, the silent pleading of a man defeated.

After a few moments, he was done. His exhausted body slumped down against the couch. She slowly released her grip on his wrists, then sat back to appreciate her work. He was red faced, tears gathering in the corners of his eyes, and covered in his own cum from chin to cock. She could tell from the look on his face that he was devoid of any and all masculine pride, that she truly had taken something from him. Now for the final push. Cassidy removed a cell phone from her pocket and pointed it at Tom's disheveled form.

"Say cheese!" She said gleefully, snapping a picture that perfectly captured the fear and humiliation in her ex's eyes. Tom scrambled for the blanket near him, but Cassidy snatched it out of his grasp. "Hm? What are you doing, sweetie? Trying to cover up that pathetic little body of yours?"

"Cassidy, please, I-I don't want- please don't take pictures of me!" He tried covering genitals with one hand, using his other to cover his face. Cassidy responded by moving the phone closer to him and snapping another picture.

"Move your fucking hands right now, or I wake up the others. Tell me, how are they going to react if they see you covered in cum? I'll tell them I caught you masturbating over Paige."

"Why are you doing this? I just--" He mewled in response.

Cassidy just smirked and held up three fingers. "Three. Two. O--". Tom dropped his hands. He knew her threat was real, that he had no choice but to comply. "Good boy." She purred, "But I've already got a few pictures of you like this. I have a better idea." She fished around in her pocket for a moment before tossing something over to Tom. "Your underwear is ugly. Put these on."

He picked up the crumpled piece of fabric, holding it out in front of him. He nearly gasped when he saw what it was: A pink, frilly pair of panties, complete with a little black bow on the front. He opened his mouth to protest, but Cassidy shut him down before he could even start. "If you even think about telling me no, I'll send these pictures to everyone on my contacts list." And just like that, Tom was taking off his boxers.

Cassidy snatched them from his hands as soon as he had taken them off. "You won't need those anymore. Those are for men, but you're not a man, are you? You're a little girl." Tom slipped the panties around his ankles. His lip was quivering slightly, a fact that drove Cassidy crazy in all the right ways. She could practically smell his breaking point. "Say it," She said, almost breathlessly, "Say you're a little girl."

Tom pulled the frilly panties up over his cock. "I'm a little girl." He whispered, averting his eye towards the ground. "That's right." She replied with a cruel smirk. She snapped another photo with her phone, making sure he was aware that his humiliation was immortalized. Tears began streaming down his face, though he tried to hide that fact from Cassidy. He was, of course, unsuccessful. Cassidy felt almost high watching the last of his pride fall off a cliff. She was close, so tantalizingly close to gaining a slave for life.

"Alright, Tom. We're almost done. You just have to do one last thing for me, and then I'll leave you alone. Ok?" Tom still couldn't meet her gaze, but he gave a small nod. "Good. Stand up." He did what he was told immediately now, without any protest or hesitation. Whether that was due to the blackmail Cassidy now possessed, or his spirit had just been sufficiently broken, she didn't know. Either way, she knew she was in control. "Walk to the center of the room. Don't wake anyone up." He gave her a small glance at that, but again, followed the command without argument. Tom tiptoed past his sleeping friends, stepping over Paige, past James, right by Derek's sleeping head. He stood in the center of the room, surrounded by his friends. Despite his predicament, his dick was already standing tall again, straining against the pink lace panties in an almost comical display of emasculation. Cassidy had to stifle a laugh, placing a hand over her mouth to muffle the giggles.

"Looks like you're enjoying yourself. Guess we'll have to do this more often." She saw a delicious spark of fear flicker through his eyes. "Start stroking your cock, sissy. I want to see you cum again." As a fresh batch of tears began running down his face, Tom wrapped a hand around his humiliated cock and began to pump. Cassidy took another picture, this time with flash. The entire room was brightened for a moment, the light illuminating several sleeping faces. Tom's eyes went wide.

"Cassidy," he whispered frantically, "Don't!"

She only smiled at him. There was only one thing left to do. Slaves didn't need friends, did they? At full volume, Cassidy yelled across the room:

"Oh my god, Tom! What the fuck are you doing?!?"

All four friends immediately began to stir. Tom's face went white with shock, and his mouth widened into an circle. He tried to stammer out a response, but the words simply wouldn't come. Paige opened her eyes first.

"Tom? What are you wearing? And what are you--oh my god, is that cum?"

James chimed in. "Dude, what the fuck?! Are you jerking off right now?"

"Hey, that's my underwear! That went missing the last time we slept over at my place!" Cassidy added, doing her best impression of incredulity.

Suddenly, the room was alive with shouts, jeers, and laughter, all directed towards Tom's mostly naked form. He tried to defend himself, tried to explain; but only sobs would escape his lips. As the taunting got louder, and the accusations more emphatic, Tom found that his cock was only getting harder, his body fundamentally betraying his mind, as if it had already accepted its new role as Cassidy's slave.

Cassidy just smiled, content in the knowledge that Tom's torment was only just beginning. She took our her phone, selected the photo of Tom in her favorite pair of panties, and hit "send all". Now she was sure he'd never have a social life again.

That's ok though, she thought. I won't let him leave my apartment anyway.