The semester flew by for Kaitlyn, her secret becoming less and less shameful. She had not met with Jesse to pay her part of the deal as midterms and exams began to overwhelm them both. However, as the semester went on the two continued to text and talk… almost as if they were becoming friends.

Their conversations were innocuous enough; discussing parties, classes, sports, or movies. No mention of finding time to see each other or Oliver was made, and that had been a blessing for Kaitlyn. Since their argument, Oliver had begun to grow distant from his sister. Of course, he felt hurt that she would keep a relationship secret from him and he believed she should be more open, but how could she? If she told him the truth of who she was seeing and why, it would devastate him. No, the secret was a necessity and while it was no longer shameful, it was just as important that nobody found out. Her friends, on the other hand, were relentless.

“So, have you seen your mystery man recently?” Veronica would ask, pushing Kaitlyn for more information.

“Yeah, what have you two done lately? We need the details!” Mel would say, almost salivating at the thought of more gossip. 

Kaitlyn always had an excuse for why she and her mystery man couldn’t meet because they were true. Exams, classes, family; all the normal things that keep University students busy. But that wasn’t enough, and they were slowly starting to close in on his true identity. Explaining how she didn’t want to jinx their newfound relationship, Kaitlyn had convinced the girls that she didn’t want to tell them his name: hoping that they would simply let it go. It turned out, however, that both Mel and Veronica had begun an inquisition into the Delta Kappa Alpha fraternity; the fraternity Kaitlyn claimed the man she was seeing was a part of. In reality, Jesse was in Sigma Sigma Omega, which would hopefully keep them from finding out the truth. They had gotten closer and closer to the men in Delta Kappa Alpha though, and had come up empty-handed; it was only a matter of time until they deduced she had lied.

The line of questioning always was at its worst when the trio was drinking together. Parties now felt the same as minefields, forcing Kaitlyn to tiptoe through them to avoid setting one of the girls off. She was well aware of the effect alcohol had on her, loosening her inhibitions as well as her tongue and it was a recipe for surrendering her secrets. Especially now that the semester had come to an end, it would be non-stop celebrations and risks for spilling the news to her friends. Finally, she had reached New Year's Eve; after the final party of the year it would be back to studying and Kaitlyn felt like she would be in the clear. More importantly, with the start of a new semester came a quiet lull in their daily lives that meant one thing: seeing Jesse.

She couldn’t deny how the thought of seeing him again made her heart quicken. Kaitlyn had long since begun to accept her feelings for Oliver’s bully, or, now former bully, and she knew that he was starting to feel the same. Perhaps it was simply their sexual chemistry that continued to bring her mind back to Jesse, his touch, his cock, and the pleasure he gave her, or maybe it was something more. Regardless, their deal was quickly approaching its end and Kaitlyn wasn’t ready to give it up. The fact they hadn’t seen each other in over a month felt excruciating, but she knew that it allowed her to prolong their temporary relationship as they explored those feelings. 

All she needed to do was get through this last damned party.

“Come on, loosen up Katie!” Mel laughed, handing Kaitlyn a shot glass, along with one to Veronica.

“You seem lost in thought, come on! It’s the last party before we have to get back to classes,” Veronica said, before downing her shot in one swift motion. With a grimace, she sighed and gestured to Mel and Kaitlyn’s undrank shots. “Even if your boy toy isn’t here, we can find you someone else!”

“It’s not about finding someone else,” Kaitlyn huffed, before downing the drink with an equally unhappy grimace. “Ack!... and it’s not about him, just have a lot on my mind.” 

“Yeah, like not getting laid at all over the holidays. I know the feeling,” Mel sighed, before gulping down her shot. 

“That’s all you ever worry about, isn’t it, Mel?” Veronica laughed, shaking her head with disbelief. Turning her attention back to Kaitlyn, Veronica gently rubbed her shoulder. “Alright, we won’t bother you about him anymore. But you do need to go find someone for your New Year's kiss! The Delta Phi Psi guys aren’t the most exciting people to party with, but there are a few cute guys among them! Plus, I know for a fact Richard was asking about you.”

Kaitlyn rolled her eyes at the comment. Delta Phi Psi was almost entirely made up of students who attended the business school at Britannia Heights University. Almost all of them had rich families who donated to the school which was one of the criteria for membership. Not to mention the many accusations of men mistreating women on campus, none of which had been proven of course, but Kaitlyn was wary of them, to say the least. While Sigma Sigma Omega may be a frat made up of party animals, bullies, and ‘dumb jocks’, she felt far more comfortable around them than Delta Phi Psi.

“Yeah, no thanks. I’d rather date my vibrator for the rest of my life,” Kaitlyn groaned, before gesturing to a group of men all looking across the party at them, almost leering at the three girls. “But you go for it, your pick of the litter over there!” 

“Oh, no way in hell. We’re finding you a guy to kiss, I’ll just kiss Mel at midnight,” Veronica laughed, before getting a frown from Mel in response.

“Hey! It’s not that bad,” Mel grumbled in annoyance, causing her two friends to laugh. As Veronica and Mel began to discuss the possibility of their own New Year’s kiss, Kaitlyn felt her phone vibrate in her back pocket. Sliding it out, she took a look and saw that a new message had come in from Jesse, her heart immediately beginning to quicken. 

Jesse: Hey you, happy New Year!

Jesse: I know we’re normally supposed to say it AFTER midnight but wanted to see what you were doing

Smiling down at her phone, Kaitlyn began to quickly type out her reply, her heart racing. 

Kaitlyn: Happy New Year :) 

Kaitlyn: The sorority is having a party with Delta Phi Psi tonight. I wish it was literally anyone else lol

Jesse: I feel that, anytime they’re invited to a party I immediately want to bail

Jesse: If you’re looking for something else to do, a buddy of mine is having a party off campus. None of the SSO brothers are going to be there 

Jesse: No pressure though

Feeling her stomach drop at his response, Kaitlyn bit her lip nervously. She wanted nothing more than to leave her sorority party and go to see Jesse. The thought of him as her New Year’s kiss was almost enough to make her drop everything right then and there… but what would she tell Veronica and Mel? Looking up from her phone, she saw that two of the Delta Phi Psi brothers had come over and begun to chat them up, seemingly paying no attention to Kaitlyn anymore. With a smile, Kaitlyn gently tapped them on the shoulder, before gesturing towards the door. 

“Hey, I’m going to head out. I’m a bit tired,” she said, giving them an apologetic smile. Both of the girls looked at her sadly, shaking their heads.

“Aww, you okay? Are you sure you can’t stay?” Mel asked, taking Kaitlyn’s hand gently. “Want us to bring you back home?” 

“No no, it’s okay. I’ll call an Uber and get home,” she replied, taking a step back towards the door. “Have fun, but not too much, okay?” 

“Yes Mom,” Veronica laughed, before leaning in to hug Kaitlyn goodbye. Turning on her heels now that she had bought herself an alibi, Kaitlyn responded to Jesse’s text.

Kaitlyn: What’s the address?

—--------

The entire Uber ride had Kaitlyn squirming in her seat. She and Jesse had gone so long without seeing one another that she had fantasized about being reunited. The thought of his touch had plagued her mind since they had last seen each other, and even when Kaitlyn had tried to get herself off she was unable to unless she thought of Jesse. During the drive, she continuously looked back at her phone, looking at the various photos she had taken before of herself after their previous hookups, her ruined makeup, her disheveled hair, and her euphoric eyes: all of which brought her mind back to each time she had been fucked by Jesse.

Finally, she arrived at the address Jesse had given her. The house was massive, clearly belonging to a wealthy student whose family didn’t care if it was trashed for New Year's Eve. Even from the sidewalk she could hear the loud, thumping bass of music within, laughter and cheering from drunk students along with cat-calling and hollering. The party seemed far more wild than she was used to attending; even her sorority parties, which often had some people using drugs or having sex, never got this out of hand. Kaitlyn steeled her nerves, knowing that Jesse was inside waiting for her, and if she backed out now, it would do nothing but provoke his ire. Opening the door, Kaitlyn walked inside the house confidently but was unprepared for what she saw.

Inside, the house was packed. Drunk students were crammed in shoulder to shoulder, dancing, playing drinking games, and generally celebrating the New Year. It was by far the most full party that Kaitlyn had ever attended, and the energy in the room was hypnotic. Casting her eyes around the room, she could see couples making out on all furniture, in the dark corners of the dimly lit party, hands in pants or people grinding a little too enthusiastically. Just what had she gotten herself into? 

Suddenly, Kaitlyn felt a pair of strong arms wrapping around her waist and the warm feeling of a body pressing up against her back. With a yelp of surprise, she looked over her shoulder, looking into the dark eyes of Jesse.

“Hey, beautiful. Glad you could make it,” he said happily, the smell of alcohol on his breath. The moment she saw him, felt his warmth pressed firmly against her back, it felt as though she were melting. She had been craving Jesse for so long, but she hadn’t expected to feel like this. Feeling her face burn scarlet, she pressed herself back, letting him tighten his grip around her waist.

“Mmm… hey yourself,” she replied, before craning her neck to peck his lips. “Thanks for inviting me. It’s wild here, huh?”

“You have no idea. Mack’s parties always get crazy, and it’ll just get worse as the night goes on,” he said, before gesturing towards the far side of the room. “Come on, let’s get you a drink.” 

With a nod of agreement from Kaitlyn, Jesse released his grip around her waist before taking her by the hand. He led her through the crowd, weaving through the throng of drunken partygoers and towards an equally packed kitchen. Several kegs had been set up on the center island, along with numerous bottles of liquor that were constantly being used to fill drinks. Jesse began to pour them each a rum and coke, handing one to her in a red solo cup. 

“I’m surprised you actually came, I figured you’d be too busy with your sorority party,” he said, before taking a long sip of his drink. 

“I figured if you were inviting me over, it was because you were striking out with all of the girls here. I needed to take pity on you,” she replied, jabbing him playfully. Jesse let out a laugh at her barb and nodded before flashing her a charming smile. 

“You know me, I have no game,” he chuckled, before gesturing at the crowd. “But striking out was the best thing that could have happened. Especially since it brought you here.” 

Kaitlyn smiled softly at the flirtatious comment. Her time with Jesse had felt so different since the first time they had hooked up. He had tortured her brother for years, and the only reason they had grown closer was because Jesse all but blackmailed her into it. Memories of how degrading their first few encounters were; Kaitlyn being throat fucked in the school bathroom, being forced to walk home with her hand and arm splattered with his cum, being fucked on Oliver’s bed… now he was flirting with her. Jesse could easily say he wanted his next payment and she would obey, so why was he making the effort to charm her? 

Perhaps he simply liked the chase. He wanted to feel like he could charm the sister of someone he bullied, and not get sex just because he threatened to continue bullying her brother. But, had he not threatened her in the first place, would she have given in? It was hard for Kaitlyn to decide; although she found him physically attractive she hated his personality. She still harbored some level of resentment for how he had treated Oliver in the past… but she had begun to see another side of him. Putting her hatred aside to make him happy had done the trick in protecting Oliver so far, it had quickly become a win-win.

“Well, cheers to your lack of game then,” Kaitlyn said with a smirk, tapping her cup against Jesse’s before they both took a long swig. The pair continued to talk for what felt like hours. It was such a refreshing change for Kaitlyn, normally when she and Jesse met there was little talking and they would dive right into the action, but tonight was different. He hadn’t asked about or commented on their arrangement once, and their rapport felt so normal. It reminded her of her last relationship and how she and her boyfriend had started dating after a party. 

The drinks that Jesse continued to make were strong, and it wasn’t long before Kaitlyn began to feel the buzz taking over. Not only was the alcohol loosening her inhibitions but that still constant hunger Jesse inspired continued to gnaw at the back of her mind. Eventually, that hunger began to win out. 

“Come on, let’s go dance!” Kaitlyn said, finishing her drink and taking Jesse by the hand, dragging him back towards the packed living room. With a laugh, Jesse nodded; downing the rest of his drink, before being led back into the crowd. There was barely enough room for one person to join the dance floor, let alone two, but Kaitlyn used it as an opportunity to get close to him. Jesse eagerly played along, taking her by the hips and pulling her body close to his once again; her ass pressing against his crotch. 

Their hips swayed to the thumping bass of the music, letting the crowd around them disappear into the background. To Kaitlyn, there were only the two of them, moving in tandem. She could feel her heart pounding harder and harder, and she wondered… could Jesse feel it? Letting her head fall back against his chest as their bodies ground together, she could feel Jesse’s breath on her, his hands exploring her body. Suddenly he leaned in to kiss her, his tongue pressing into her mouth hungrily, which she happily accepted with a soft, contented moan. Reaching a hand up, Kaitlyn slid her hand behind his neck, holding him in place as they passionately began to make out. Spreading her legs slightly to slide back even closer to him, Kaitlyn began to grind herself on his thigh, feeling a shock of pleasure creeping throughout her body and causing her to moan into the kiss.

His scent, the firmness of his grip, and the pleasure she felt grinding on him were more intoxicating than the alcohol. It was everything she remembered, and everything she had been craving. Kaitlyn was tempted to ask Jesse to take her right then and there… but she wasn’t ready to become an exhibitionist just yet. Pulling away from his lips just enough to speak, Kaitlyn bit her lip with a mischievous smile.

“Mmm… I can’t take it anymore…” she panted, her innocent eyes full of hunger as she stared longingly into Jesse’s. 

“You read my mind… come on,” he said, leaning in to kiss her once more before sliding his body away from Kaitlyn, but keeping one hand firmly on her hip. Kaitlyn let Jesse lead her through the crowd, deeper into the house until finally they reached a doorway. Opening it, Jesse ushered Kaitlyn into a small bathroom, the closed door doing nothing to drown out the noise of the party outside. “There are people all around, so we’ve got to be quick unless you want someone to come watch.” 

Kaitlyn giggled at the comment, shaking her head before leaning in to kiss Jesse again, her hands reaching to his belt. “Don’t think I’m interested in that right now… but I am interested in this.” 

With his belt undone, Kaitlyn sank to her knees, feeling as though she had been possessed. Her mouth began salivating as she tugged his boxers down, with Jesse leaning back against the sink. The look of surprise mixed with excitement on his face told Kaitlyn everything she needed to know: he had planned for something like this to happen but was surprised by how eager she seemed. Even with their last few meetings, Kaitlyn had been much more forward; of course the sooner they reached ten orgasms, the sooner their deal would be completed, but it had become something more primal. They craved each other, and it was apparent how badly they wanted to enjoy each other’s bodies. 

Kaitlyn finally slid down his boxers, releasing his cock and she wasted no time leaning in and kissing along his shaft. Feeling her lips against his sensitive skin, Jesse let out a soft sigh of pleasure, his cock slowly growing against her face. Closing her eyes, Kaitlyn simply enjoyed the experience, relishing in his scent and taste, her lips exploring his cock. One hand gently gripped him and began to stroke, assisting with his growth as she lifted his shaft to continue kissing along the underside; down to his balls. She opened her mouth and let her tongue hang out, teasing along his balls as she continued to slowly stroke his manhood.

Her tongue began to lap at the underside of his balls, taking them into her mouth and gently sucking on them. Letting out a soft, low moan, Kaitlyn savored the taste of his skin in her mouth, the soft taste of skin and sweat, his scent filling her senses. With her free hand, Kaitlyn reached down to undo her jeans, sliding the hand down to tease herself. Feeling the jolt of pleasure coursing through her body, she gasped but continued pleasuring Jesse, desperate to make the most of this situation. 

“Fuck that feels good…” Jesse panted, running a hand through her hair and gently gripping it. “Stop teasing, I want to feel you suck my cock…”

Kaitlyn obeyed instantly, gently sliding herself up from Jesse’s balls; dragging her tongue all along his shaft, pausing for a moment to tease his frenulum, before finally making it to the tip. She took her plum lips and wrapped them around his head, her tongue swirling around to coat it in her saliva, teasing him all the while. Kaitlyn looked up at Jesse, her eyes wide and pleading, almost as if to ask if he was enjoying himself. Finally, Jesse could no longer take her teasing, and with a rough thrust, he pushed himself deeper into her throat.

The sudden fullness of his thrust made her body quiver and almost gag. Over their previous hookups, along with a healthy dose of practicing in between, she had been able to, for the most part, control her gag reflex. The sudden roughness took her by surprise though, and as his thick cock slid down her throat, the room filled with a loud glk. Jesse wasted no time, beginning to thrust, using her throat as a toy. Kaitlyn was in heaven, holding her head in place as his cock began to violate her throat over and over again, a wet slapping sound filling the bathroom. The hand that had been stroking his cock slid down to massage his balls, her lips closing around his shaft to ensure that she was giving him as much pleasure as possible. 

It became harder to breathe the rougher Jesse went, but Kaitlyn didn’t care; she was simply happy to be with him once again… helping give the pleasure that Jesse so obviously craved. The hand in her pants continued to rub small circles on her clit as Jesse used her for his own enjoyment, the room filling with the wet glk glk glk of her throat being fucked. Kaitlyn no longer wanted to be passive though; something had awoken inside of her and she craved the experience of giving him satisfaction. With each thrust of Jesse’s hips, Kaitlyn began to bob her head forward and backward, ensuring that he was able to thrust himself as deeply as she could take it with each movement. 

Pre-cum began to coat the back of Kaitlyn’s throat, drool dripping down her chin as his cock became soaking wet with a mixture of their juices. Her hand slid upwards to gently massage his balls, ensuring that no part of Jesse went without worship. His cock began to swell within her throat and his balls began to tighten in her hand, and she knew he would be finishing soon… all it would take is one last effort on her part. Bringing her hand from her pants and her other hand from his balls, she gripped his hips to hold him still, and the moment he stopped moving, Jesse let out a low groan of frustration. She looked up at him, her eyes watering from the strain almost as if to say ‘trust me’, before she began to rapidly throat his shaft, her tongue swirling and lapping against him like crazy.

Kaitlyn had become ravenous and knew that the only thing that could satisfy her now was his cum. Her head bobbed at a rapid pace, with each push in she could feel her nose pressing against his stomach as his thick member stretched her throat. With a few more loud slurps, Jesse was pushed over the edge; a loud moan of pleasure filled the small bathroom and if anyone were standing immediately outside the door, they would have most certainly heard. Cum began to pump directly down her throat, bypassing her mouth as she hungrily gulped it down. All the while, Kaitlyn never slowed, her mouth sucking harder now as if trying to drain him entirely. Each pulsing shot of hot cum sprayed against her throat, the salty bitterness of his cum making her feel euphoric. While she would have loved to have Jesse fuck her, she was more than satisfied with getting him off… and hopefully, he would have enough energy to return the favor. 

With the last ropes of cum spraying down her throat, he leaned back against the counter, panting heavily. Kaitlyn slowed her bobbing movement, simply keeping his cock nestled in her throat as she continued to gulp down the remaining seed, before slowly pulling herself back. Every agonizing second had her continuing to slurp along Jesse’s cock, ensuring that he was completely clean, finally pulling free from him with a soft sigh of pleasure. Kaitlyn wiped her mouth with the back of her hand, panting in tandem with Jesse as she grinned up happily at the man. 

“I’m so fucking glad you came tonight,” Jesse laughed, reaching down to pull up his jeans. Kaitlyn rose to her feet shakily, catching a glimpse of herself in the mirror. As far as rough oral sessions could go, she looked relatively put together still. She had avoided wearing too much mascara or eyeliner which certainly would have run, but her lip-gloss had smeared and her hair had become disheveled. Quickly running her hands through her hair, she straightened herself out and tried to make herself look more presentable.

“Me too, I’ve been craving that,” she giggled, leaning in to kiss his cheek gently. “Hopefully we can do it again soon?” 

“The night is young,” Jesse replied, as he finished doing up his jeans. Taking her by the hips he kissed her passionately, before pulling away once more and gesturing to the door. “Come on, let’s get back out and hope nobody noticed us go in.” 

Unfortunately, the moment they stepped back out into the hallway some of the nearby party-goers began to cat-call them, whistling and jeering. Kaitlyn immediately felt her skin flush as she became self-conscious of her disheveled appearance. Nobody would believe they had simply gone into the bathroom to make out. Kailyn had never been more thankful for being a stranger at a party and knowing no one else other than Jesse. That knowledge that nobody would recognize her gave her a new-found renewal of confidence, as she took Jesse’s hand in hers. 

“Come on, I need another drink to get the taste out of my mouth,” she said, giving him a playful wink.

—----

The pair spent the rest of the evening drinking, dancing and talking. In the past, whenever they had finished; Jesse would leave. It was clear that he wanted more than just sex… and that they had grown closer. Especially tonight, Kaitlyn had begun to see a new side of the bully… ex-bully assuming he kept his word to her. He was charming, playful, and funny; all words she would never have associated with Jesse in the past. Throughout the night, she had forgotten what brought them together, only focusing on the fact that they were now together. She wanted him, she craved him more than just physically, and it began to gnaw at the back of her mind if he felt the same. 

By the time midnight had arrived, Kaitlyn had felt thoroughly drunk. Every time Jesse spoke to her, she giggled like she was a teenager again, constantly flirting with him and doing everything she could to touch and be close to him. As the party-goers began to count down before the year ended, she paid no attention, lost in his eyes and smile… and as everyone's cheers rang in the New Year she lost herself in his lips. 

Their New Year's kiss had been the best she had ever experienced, not because he did anything special but because he was someone special. Her mind had been decided: she would spend the rest of their time together trying to steer him straight. Not only would Oliver be protected from his bullying ways, but anyone else who had suffered at his hands would see a newly reformed Jesse with her at his side. As their lips parted, Jesse continued to hold her close, that same hunger that had been present when she drained him into her throat returning in an instant.

“So… I was only planning on staying until the New Year started,” Jesse said, trailing off towards the end with a mischievous smile coming across his face. Kaitlyn bit her lip playfully pressing herself into his body.

“Oh? So you’re planning on abandoning me at the party you invited me to?” she asked playfully, beating around the bush. Jesse rolled his eyes sarcastically at the comment before leaning down, his lips brushing against her ear as he whispered.

“No, I plan on taking you back to my place so we can celebrate the New Year together,” he whispered, before biting her ear-lobe playfully. The feeling sent an electric sensation jolting down her spine, as she whimpered softly in response. Kaitlyn could only nod in agreement, as Jesse pulled out his phone to call an Uber. Within minutes the pair had been spirited away, cuddled in the back seat of the Uber as their driver tried desperately to start a conversation with them. Kaitlyn had no interest in speaking though, constantly kissing Jesse, her hand rubbing his lap… she was astonished he was able to focus enough to thank the driver as they rushed inside.

The moment the door of the Sigma Sigma Omega frat closed behind them, Kaitlyn couldn’t wait. She threw herself at Jesse, the pair beginning to make out hungrily as Jesse led them upstairs to his room; their lips never leaving one another. Before, Kaitlyn would have been terrified that someone would see her, recognize her, and that news of her time with Jesse would get back to Oliver… but whether it was due to the alcohol or the sheer need she felt, Kaitlyn no longer cared. Finally making it to Jesse’s room, he lifted her easily into his arms and placed her on the bed. 

She reached down for his belt, but Jesse stopped her, catching her wrists with a small grin and a shake of the head.

“No, I need to pay you back for earlier,” he said, kneeling in front of her and undoing her pants. She cursed herself for choosing such skinny jeans, but Jesse had no trouble tugging them down and tossing them aside, revealing her lace panties. His large hands squeezed her thighs, spreading them and draping her legs over each shoulder as he began to kiss and nibble along them. It was obvious that Jesse simply wanted to tease her; and build up the tension as much as possible… and Kaitlyn hated that he knew her body so well. Pulling her panties aside, his tongue began to gently flick against and tease her clit; just as she had done to his frenulum earlier.

Letting out a loud moan of pleasure, Kaitlyn didn’t care if they were overheard. She reached down to grip Jesse’s hair to guide him, positioning his eager tongue exactly where she liked it. His wet tongue began to explore every inch of her quivering sex, moaning at the taste and relishing in her squirming at his touch. Nothing mattered anymore but the pleasure she felt, and Kaitlyn laid back and closed her eyes, enjoying the sensation. She could feel herself becoming wetter against his tongue, and she needed more from him. 

“P-please…” she panted, her thighs tightening around his head. “F-fuck me, Jesse…” 

Pulling his face away from her, he looked up, smirking playfully. Kaitlyn lifted her head enough to see him, his mouth and the lower half of his face glistening with her juices.

“I love to hear you beg for it Katie…” he chuckled, raising an expectant eyebrow. “If you want to be fucked, tell me why I should.” 

Kaitlyn shuddered at the sheer aura of dominance radiating from him. She nodded, sitting up slightly so he could see the sheer desperation in her eyes.

“Please Sir, for months all I could think about was your cock… feeling it stretch me and fill me,” she panted, almost whining in need. “The feeling of you filling me with your cum last time… It’s the only thing I can think about when I get myself off. I thought I’d be better at restraining myself tonight but after tasting your cum earlier… I need more. Please, I’ll do anything.” 

“Anything?” he asked, tilting his head curiously. “Would you let me cum in you again?”

Kaitlyn froze for a moment, feeling conflicted. It had felt incredible when they had last done it, but… it was risky. Not only was there the risk of pregnancy, there was the risk of catching something. Jesse was popular at school and she knew from seeing him both in University and high school that he had no shortage of girls fawning over him, much like she had been. There was the risk that if he had been sleeping around he could have picked something up. However, a part of Kaitlyn whispered to her like the devil on her shoulder, ‘Surely if he had something, he wouldn’t risk spreading it to you. You’ve already done it once with him, what’s the harm?’

Hesitantly, Kaitlyn nodded and smiled sheepishly at him. 

“Y-yeah… you can. Whatever you want,” she panted, her body desperately trying to grind against his face again. “Please just fuck me…” 

Jesse’s eyes lit up happily, and he immediately stood up and tore his clothes away. Before Kaitlyn could even focus, she felt his strong hands gripping her hips, pulling her body to the edge of his bed. Her eyes widened in shock as he lifted her hips slightly, positioning his cock at a slight downward angle against her soaking wet pussy. Slowly pressing himself against her, Kaitlyn gasped, feeling her lips spreading to accommodate his impressive girth. Finally, after so long, Jesse was fucking her! 

“God… I forgot how fucking tight you are…” he sighed happily, slowly sinking himself deeper and deeper into Kaitlyn’s body. She couldn’t respond, the sensation of pleasure overwhelming her mind. Like an addict finally relapsing and feeding her craving, she felt like the weight of the world had slipped away. All that mattered was the pair of them, in that bedroom, on New Year's Eve.

Even though Jesse had cum earlier in the night, his impressive stamina shone through. As he reached her depths and slowly began to pull himself out, his thrusting began to consistently quicken. Kaitlyn’s legs tightened around him, pulling him deeper into her, as his thick cock began to grind along her g-spot, hitting the perfect spots. It was as if his cock was made for her pussy, and she knew that nobody would ever compare.

Whether it was due to Jesse holding himself back, the alcohol, or a mixture of the two, Jesse was able to control his orgasm expertly. Their session felt as though it lasted hours, especially after his thrusts began to go fast and hard. Every movement pounded his manhood into her, over and over again, as her screams of pleasure filled the room. Jesse leaned in to kiss her, the pair making out and his lips being the only thing to subdue her screams. For months she had teased herself, the only thing able to give her any sort of relief was imagining this exact scenario… and she felt her built-up pleasure threatening to spill over. 

Her pussy tightened around his cock, almost as if sucking him in… but Jesse suddenly pulled himself out. 

“Huh?” she mumbled, her eyes heavy and her mind clouded with pleasure. In one swift movement, he flipped her over into doggy style. Kaitlyn braced herself on all fours, arching her back so that when he entered her body once again, he could get as deep as possible. She felt Jesse’s hands hold her hips and with one mighty thrust, pressed himself balls deep into her. No longer kissing him, nothing was able to suppress her moans of passion.

Jesse immediately began to pound into her, the room filled with a wet slap slap slap slap along with the creaking of his mattress, and the gentle sound of Jesse’s headboard hitting the wall. The cacophony was enough to wake everyone in the house, and it was fine by Kaitlyn. She needed everyone to know that Jesse was the best she ever had. Whether they knew it was Kaitlyn being fucked in this room didn’t matter, all that mattered was she enjoy herself to the fullest. Feeling her breasts swinging gently beneath her, she could feel her orgasm creeping back up, her pussy tightening around his shaft. 

With every thrust by Jesse, Kaitlyn met him by pushing herself back, feeling him bottom out with every movement. The mixture of pain and pleasure became too much and she felt liquid drip down her legs as she came hard, clenching around his cock. He continued the same pace even as she let out a scream of orgasmic bliss, her tightening body desperately trying to milk him. One of his hands released her hip and grabbed the back of Kaitlyn’s hair. Gripping her hair hard, Jesse yanked her head back, forcing her to arch herself even more so he could lean in and kiss her. She was shocked by her flexibility, and by how deep he was. It felt like his cock was pressing into her stomach, and her sensitive nerves still reeling from the after-shocks of her orgasm felt as though they were on fire. 

As they kissed, she could feel him panting against her lips, his cock swelling inside of her. He was on the verge… and as before all it would take is one last push. 

Pulling away from his lips just enough to speak, Kaitlyn whispered, “Cum for me… f-fill me up, Jesse!”

Almost immediately Jesse began to thrust like a man possessed. With a grunt of effort, she could feel him slam himself balls deep, as he let loose a flood of cum directly into her. The spray coated the inside of her pussy, spraying against her cervix. Even though he had cum earlier in the evening, it seemed like an endless torrent of seed pouring into her. It was almost frightening as she felt him pump more and more into her body. All of the fears she felt before agreeing to let him cum inside of her came rushing back… but the sheer pleasure of it told her that what was done was done. Now, all that mattered was this moment.

Even if Jesse didn’t want anything more than their deal from her… she was okay with that. Content with simply being the outlet for his pleasure, letting him take out his frustrations and pent-up sexual aggression on her. In one night they had reached their eighth orgasm. Two more and their deal would conclude. But as Jesse slowly slid himself out of her pussy, his cum dripping down her leg, and as he pulled her into his arms to lay in post-orgasmic bliss together, only one thought could penetrate her pleasure-addled mind.

‘Maybe we don’t have to end at 10?’