Roleplay Gone Too Far

Tom had absolutely no idea what he was getting into when he accepted his friends' party invitation. Make no mistake, the party was a complete mess from the start. Loud music he hated sounded through the house, and his friends bailed on him at the first opportunity.

He couldn't blame them though. Tonight wasn't supposed to be about hanging out, it was about finding someone to hook up with. That used to not be much of a problem for Tom, back when he was in his early twenties. Who knew that just a couple of years could make so much of a difference? It has been at least half a year since he last scored, and that wasn't for lack of trying.

Tom tried to approach a few girls who looked to be looking for someone too. It turned out they were, just not for someone like him. Three times, he was rejected. It should've hurt him more, but he was used to it now and knew that tonight was a long shot anyway.

Just as he was about to leave the party and head back home, someone approached him for once, instead of the other way around. And not just any someone, but a woman, a gorgeous looking woman with hazelnut hair, wearing a tight-fitting red dress.

She started talking to him. Casual small talk at first had quickly turned suggestive as she closed the distance between them and placed her hand over his.

Tom couldn't believe his luck. She was way out of his league, he knew that. But still, she was clearly interested.

They hit it off. Mandy, which he found out was her name after an embarrassingly long time, seemed receptive to his usually not very effective charms. She even laughed at his jokes.

Mandy told him that she was also alone and on her way out before she approached Tom, but now that they had met she suggested that he could join her, if he wanted to. He agreed immediately, eager to turn what he originally thought was another failed night into a sweet memory.

After a short uber drive back to her place, she left Tom in the living room of her cozy flat that she rented, while she went to the bathroom to freshen up. She told him that he could drink whatever he could find while he waited, but he remained glued to the armchair he sat on, scared of getting any more drunk and passing out before the main event.

On his phone, he informed his friends in their group chat that he was about to score with a hot babe. They didn't believe him, none of them managed to get further than hanging out at the party. He wondered about sneakily taking a picture of Mandy so he could brag to his friends. He looked up to notice she was back. His mouth opened in disbelief when he saw what she was wearing.

Gone was the tight red dress, replaced with an edgier outfit made of black fabric and leather. Mandy had on a black leather bra with multiple straps crisscrossing her shoulders and chest, paired with a loose skirt that reached mid-thigh. She even applied some makeup, surrounding her eyes with black eyeshadow.

Tom continued to stare at her in disbelief. Only when she asked him, "Like what you see?" did he finally close his mouth and composed himself.

"Um-yeah," he replied.

Mandy smiled and approached him. With a few long strides she was next to him and dropped into his lap, her arm reaching around to hold onto his shoulder. "I have a little confession to make," she whispered as her face got nearer to his.

"You're a little kinky?" he whispered back.

She giggled and leaned back. "No. Well, I am, but I have a different confession," she replied, no longer whispering.

"What then?" he asked, his eyes glued to her lips as he wondered whether this was the right time to kiss her or not.

"I broke up with my boyfriend a few days ago," she started explaining. She paused, searching for the right words to use next.

Tom had already heard this line before, many times... "And you're still not quite over him?" he asked with a sigh.

"Kind of. Yeah." Mandy nodded.

He knew this was too good to be true. Nothing was going to come of this. She'd just cry on his shoulder all night as he consoled her, telling him how great he is after, and then never calling him back.

Tom tried to gently push her off of him so that he could get up and go home. He wasn't in the mood for this tonight, he'd rather just drink some more and then go to sleep in his own bed. "That's alright," he informed her. "We don't have to-"

"Let me finish," interrupted Mandy as she held onto him, not letting him push her off. "This is happening tonight, at least as far as I'm concerned. It's just that..."

He watched her face turn from a gentle expression to one full of anger and then back to her angelic self. He waited patiently, letting her get it all out. Maybe she meant it when she said tonight was happening, he just hoped she meant the same thing he did.

"My ex, he... hurt me," she continued.

He didn't want to hear any of this. Not that he didn't care, he just wasn't her therapist or something.

"I don't mean he hit me, I mean emotionally," she continued. "Tonight was the first time I went to anything social since he left. At first, I just felt sorry for myself and cried in my bed all day. But fuck that." He could see her eyes were watery as she continued staring down at her hands. "He was always a jerk, never caring what I thought or wanted. I should've ended it a long time ago, but..." Her eyes widened as she looked up to meet his gaze. "Oh, I'm sorry, I didn't mean to drop all of this on you, I'll get to the point." Great, he thought. "I was thinking, that maybe, if you're okay with it. That you could help me get over him."

Not exactly the thing you want to hear from a girl you're trying to hook up with. She clearly had issues, but he wasn't looking for a longterm relationship anyway, just a couple of wild nights together, so he could make do with a little crazy.

"Sure," he replied. "Help you, how exactly?"

She smiled back at him and wiped her eyes with her hand, causing her eyeshadow to get even messier. "Well, I was thinking maybe we could do a little roleplay."

"Okay?"

"I'd still be me and you'd pretend to be my ex. We'll have a little... you know, 'hatefuck session' together so that I can get all this pent-up aggression out of my system." She raised both her eyebrows. "Oh, and trust me, there's a lot of it."

Yeah, this was getting real weird, real quick, he thought. Under normal circumstances, he'd bail on her, but beggars can't be choosers.

"Alright, I can do that. What do you want me to do then?" he asked, his mind already clouded with lust ever since her hand stroked his thigh during their whole uber ride to her place.

"Really? You'll do it?" she asked, immediately hugging him. "Thank you so much." She let go and sprang up to her feet. "Okay, I was thinking something like this. Let's pretend that you came back after breaking up with me, okay? I'll take the lead, so just follow. Oh, and I'll probably get a little rough, that okay?"

He nodded in response as he got up, trying to keep up with her. Looking over her lean figure, he was sure he could take anything she'd dish out without much of an issue.

"Great, come on," she said and took a hold of his wrist, pulling him behind her as she walked to the front door of her apartment. "You'll knock on the door, and I'll answer already in character, okay?"

"Sure," he responded, unsure if she was even still listening. She seemed to be in her own little world, excited to have her fantasy play out.

She opened the door and shoved him out into the hallway. As the door closed, she stopped and leaned her head out to face him. "Oh, and I'll call you Bryan from now on, okay? That's the name of my ex."

He nodded at her and smiled.

"Thank you again for doing this."

"No problem," he replied.

"Give me a few moments before you knock, so that I can calm down a little and get into character."

He nodded at her retreating head before the door closed. Tom turned and leaned onto the wall next to her door, checking his phone. It was nearly one in the morning, and he was alone in the hallway of some strange building, about to roleplay that he was an ex-boyfriend of some crazy girl so that she could fuck her anger away. This was certainly not how he saw his night going, and while it could be better, it definitely could have been worse.

It really was too bad that Mandy was clearly mental, because Tom could see himself waking up next to her every morning. With all her energy and cuteness, they'd make a good couple. But he wasn't about to go unraveling the minefield her past obviously was.

After almost ten minutes of browsing his feed, he put his phone back in his pocket and turned to the door. He had a bad feeling. Last chance to back out, he thought. He wasn't sure why, but it felt like he was about to step back into the lion's den. He took a few deep breaths to calm himself down. A few more minutes went by, and he was finally ready to get the show started. He knocked on the door and waited.

It didn't take long, and the door swung open. Mandy looked out at him, tears in her eyes. A white silk bathrobe covered her daring outfit from before. "What do you want?" she asked with disdain. She really got into her 'role', he thought.

"I came to-uh," he struggled to come up with something.

"Came to what? Apologize? Insult me some more?" she barked her questions at him before pulling him inside by his shirt collar and slamming the door closed behind him. "I can't believe you cheated on me Bryan. I loved you, I... I still love you. And you love me. Why would you do something like that to me?" More tears began to roll down her eyes.

Tom was completely stunned. This was going way beyond just some casual roleplay. He had to admit she was a pretty good actress though.

She pushed him up to the closed front door, still gripping his shirt with her hand. "Well? Cat got your tongue? Why don't you tell me how lousy I am in bed again and how much better 'Stacy' is?"

This was going way too far, maybe this wasn't worth it after all. "Um, I-uh..."

She pulled him closer, leaning in, and... kissed him. He opened his mouth and let her tongue meet his, her lipstick tasted of cherries. Tom winced as she bit down hard on his lower lip and broke off the kiss.

Mandy let go of him and stepped away. He looked up at her, she was smiling at him as he checked if his lip was bleeding with his finger. "Mandy, I think this is all a little too-"

Her hand stroking the side of his face made him pause. Her bathrobe hung open, revealing her outfit again. She snickered when she noticed his eyes landing on her almost exposed breasts. Her fingers stroked up to his left ear and gently caressed it. All his hesitation was being washed away by the sight of her perfect body.

He yelped in pain as she took a hold of his ear and pulled at it. "Come on," she said, and continued pulling him by the ear behind her. "I'll show you how much you hurt me."

They stopped in what he assumed was her bedroom. A large queen-sized bed with a metal frame dominated the small room, its headboard made of long metallic pipes.

She let go of his ear, meaning Tom could finally stand up straight. His ear still hurt as he softly rubbed it. Meanwhile, Mandy stepped behind him, pulling his shirt off in one swift movement, and then pushed him onto the bed.

The mattress was soft, and the bed creaked as his body bounced on it. He turned onto his back and looked back up at her. She was watching him like a predator watches its prey. Her bathrobe was long gone. Seeing her now, towering over him in the leather outfit, he felt vulnerable, like a cornered animal.

She smiled as if she could read his thoughts and stepped closer to the edge of the bed. Slowly she crawled onto the bed and over his body, straddling him with her knees on either side of his chest. She looked down at him, still smiling. Her hand slowly caressed his face, stopping when it reached his smooth chin.

"Are you sorry, Bryan?" she asked, staring into his eyes.

He nodded, his eyes locked with hers.

"Did you come back to apologize?"

"Yes."

She slapped him hard.

"Do you think you can just come back here, say you're sorry, and we'll be back together?"

With how good and convincing her acting was, he started to get into it too. "I'm sorry Mandy, it was a mistake. Please, take me back. I was a jerk, let me make it up to you, please," he begged as his hands slowly traced over her stomach and up to her breasts. Before he could get his palms all the way to their destination, she took a hold of his wrists and pressed them down onto the mattress above his head.

"It's not going to be that easy," she said, leaning down closer to his face. "First, you'll have to convince me that you really mean it." He nodded eagerly, but before he could say something, she continued. "By taking some well-deserved punishment."

He continued nodding, horny and ready to score. "I will, whatever you want."

Her smile widened as she leaned back. "Good." She let go of his hands and reached over to the bedside table. He watched her exposed hip as the skirt shifted to the side with her.

Tom froze when he saw what she pulled out of the drawer. A pair of leather cuffs. They were sturdy-looking ones too.

Mandy slowly reached for his left wrist, still pressed against the mattress above him. She gently wrapped the cuff around it and pulled his hand up to the headboard, looping the chain connecting the cuffs around one of the vertical metal bars. When she reached for his other wrist to pull it up too, he resisted, keeping it firmly in place.

She looked into his eyes and raised one of her eyebrows. "Is this how you want to show me how sorry you are?" she asked.

"Mandy, I don't think I'm comfortable with-"

She squeezed his cheeks before he could continue. "If you're gonna act all bratty like you always do, Bryan, then we are over. Either let me take the reins this time, or you can go. Your choice." She let go of him and waited.

He knew this was a bad idea. But he also knew that he was hard as a rock and she hadn't even touched his dick yet. All her forcefulness was driving him mad with lust, he had never met a girl like her before. As much as he knew it was the right choice, he couldn't just leave now, not without getting some relief first. He'd just have to go with it for a while.

He raised his right hand up to the cuff voluntarily. Seeing this, she smiled and cuffed his right hand.

"Try to get out," she told him.

He tried pulling his hands down, but the cuffs held strong, and the metal bar the chain was looped around did too. He wasn't putting all his strength into it, but with how little it budged, he already knew that he wasn't getting out without her help.

"I can't," he replied. Looking up at her, he saw her smile widen, her eyes glowing with excitement.

"Let's get started then," she said, and pinched both his nipples.

Tom winced in pain and buckled under her, but she remained firmly on top of him. She shushed him and caressed his bare chest, her fingers tracing over his muscles.

"You started working out since you left?" she asked.

Unsure what, if anything, he should say, he just nodded.

"Hmmm. I always asked you to get in shape, but you kept on about how going to the gym was stupid. But a few nights with that whore Stacy, and you go to the gym like an obedient little pet of hers." She continued tracing her fingers over his smooth skin. "But you aren't hers anymore. No." Her sharp nails began to scratch across his skin, not drawing blood yet. "You're all mine again. Right where you belong."

She leaned down and kissed him passionately. Their tongues were wrestling for control. Briefly, she leaned away, looking into his eyes. "Right?"

He wasn't paying attention. There was only one thing on his mind, this whole roleplay bit was just a distraction. Seeing her intense stare as she awaited his response, he improvised. "Yes." Her smile told him that was the right answer. Her head dove down again, connecting their lips.

She shoved his face to the side as their lips parted. "You don't deserve me," she said and began to shuffle on top of him. Soon he was facing her backside, barely covered by the loose skirt. From the lower angle, he could tell that she wasn't wearing anything underneath.

He felt her undo his belt and pull his pants down to his knees, exposing the impressive tent he was pitching in his boxers.

"I see you are still as horny as always," she continued talking as she slid his boxers down and took a hold of his member, slowly stroking it. "You'd love to stick this in me and get off, wouldn't you?"

"Yes Mandy," he moaned from behind her.

"Not this time, though," she informed him as her teasing hand left him. She propped herself up on his chest and looked back at him. "This time, my pleasure comes first." She slid her butt back and dropped it on his face. Her wet lips were right over his mouth. He didn't need to be told what to do. He had plenty of practice and immediately got to work with his tongue.

She seemed very receptive to his tender care, and moaned in response. "Hmm, what's this? You never used to like eating me out, and now you're like a pro. What-" She couldn't help it and had to pause for a second as her body shivered from the sensations his tongue was sending through her. "You had training, didn't you?" Her hand returned to stroking his cock. "From that bitch Stacy." Her grip tightened, driving her nails into his sensitive skin as she pulled hard, eliciting a pained groan from him.

"But that's fine," she continued, returning her fingers to gentle, teasing strokes. "Now you belong to me again. But I can't just let your cock inside of me after it was in her." Her hold tightened again, causing him to wince in anticipation, but no pain came this time. "At least not until I give it a thorough cleaning."

He felt her shift on top of him. Her warm breath flowed around the tip of his cock. Shortly after, her tongue slowly traced up his length. When it reached the top, she enveloped his cock in her mouth. Her tongue continued teasing him as she took him deeper.

Tom shuddered. His mind was flooded with the sensations her mouth and tongue put him through. It was clear that she was just as experienced at giving head as he was. After just a few moments, he was right on the edge. And as if she could sense this, her movements slowed, keeping him right there.

He moaned in frustration and continued working his tongue, sure that if he managed to get her to climax, she would return the favor. But even when her body rocked on top of him as her orgasm hit, she didn't relent in her teasing. His frustrated protests continued as she rode his face to another orgasm.

Eventually, after about half an hour, which felt like a lifetime to him, she stopped and slid down off of his face back onto his chest. Her mouth left his frustrated cock as she sat up and shifted around to face him again.

"Please, Mandy, I have to-"

She pressed her finger to his lips, silencing him. He could smell himself from her fingers that were fondling him just moments ago. She grabbed his chin with her fingers and pulled his mouth open.

He waited, expecting another kiss. Instead, she leaned her face over his and spit into his open mouth.

He coughed, trying to get the taste of her spit and his precum out of his mouth. "What the-"

"We're not done yet, but I promise I'll let you come if you continue being a good boy for me, Bryan."

She looked completely unrecognizable to him. Gone was the sweet girl he met at the party earlier. This girl was trouble.

"Listen, I-"

She silenced him with a slap to his left cheek. "You'll only speak when spoken to, understand?"

He should get out of there, demand to be let go or something. He knew that. But he still hadn't gotten what he wanted from her... what he needed. He swallowed the last remnants of her spit in his mouth and with it, the last of his hesitation.