Winning Her Over

All characters in this story are over 18 years of age.

Gwen woke the next day still completely nude. Lying down with her eyes closed, she could pretend the events of last night never occurred. She could pretend that her little brother's creepy best friend, Jimmy, never saw her naked, and what's more, never ran his tongue over her entire body - never made her cum. She could pretend he never took photos of her while she was recovering from her orgasm. And she could pretend she never agreed to fuck the little creep so that he would delete them.

But what made it worse, was that she enjoyed it. She had been sexually frustrated with her boyfriend for the past few months. The build up, and his surprisingly skillful tongue was all that was needed to push her to have one of the best, most explosive orgasms she's had in a long time. It didn't help that she was also intrigued about his big dick. Her boyfriend's dick was on the smaller side, so despite trying to convince herself that she was repulsed by what happened, a part of her ached to feel his dick inside of her. She was quite curious how his dick would feel sliding up and down her vagina. How the head would push inside her and would begin pumping in and out of her. She felt the familiar sensation of wetness in her pussy and the tingling in her loins. Fuck, stop thinking about it! There was no way she was going to enjoy sleeping with that blackmailing pervert.

But as always, reality hit her like a brick. Checking her phone, she had a message from Jimmy that simply said: 'Last night was fun, can't wait for tonight ;)' Oh god.

She didn't want to go downstairs yet because she knew her brother, Ted, and his friends Carlos and the perverts Ben and Jimmy were still there from last night's sleepover. She didn't know if she could handle the embarrassment or look her brother in the eye. So lying in bed seemed like a good alternative.

Eventually however, her bladder and empty stomach forced her hand. Putting on a t-shirt and shorts, she headed out of her room, hoping to do her business and retreat back to the safety of her room.

But as she entered the kitchen, she saw all of the 18 year old boys eating leftover pizza. At the dining room table.

"Morning sis, you feeling better?" Her brother asked.

"Morning. Yeah, feeling better." She said monotonously. She didn't mean to be so reticent, but with Jimmy sitting right next to her brother and grinning knowingly at her, she found herself wanting to stay silent.

"Good morning Gwen. I hoped you had a good night's rest and sweet dreams. I know I did. You were all that I dreamed about." Jimmy spoke up, wiggling his eyebrows at her suggestively.

"Dude gross, that's my sister."

"Gwen doesn't mind, do you Gwen?"

"Gross. I hope your dick gets caught in a door." She mumbled at him. The four boys laughed.

"See, Jimbo, no way you're ever getting Gwen. She's way out of your league" Ben chortled.

"I'll win her over." Jimbo smirked.

Carlos was silent as always. In the years she had known Carlos, they had never said more than a few words to each other. Not for lack of trying on her part, he just seemed to have trouble talking around her. Around most girls it seemed, from the stories she heard.

Ben, the other creep of the friend group, spent half his time joining in on the jokes, and the other half ogling her when he thought she wasn't looking. But she would notice his head turn her direction when she would bend down to stare at her ass, or peer down her top hoping to get a good look at her cleavage. While Jimmy was the obvious pervert, Ben, she felt, was the more discrete, but just as equal, creep. His little rat face and small, scrawny body only added to his creepiness. Whenever he was around at their house, he would always end up sitting next to her and would "accidently" cop a feel. Like Jimmy, she was pretty sure he snooped around her room, because her clothes (mainly used panties or bras) would sometimes go missing, and it was only after Ben had visited her brother, but she had no real proof. Jimmy was at least friendly with her, She did not like Ben.

The four boys (well, three, minus silent Carlos) joked around some more as she prepared toast. She made it a point to look at Jimmy as little as possible. She knew if she looked at him, last night's escapades would come screaming back and she would die of shame. She could feel his eyes on her, though. She knew he was probably undressing her with his eyes again (as usual, the creep), but this time he knew exactly what she looked like without clothes. He would never need to fantasize what she looked like naked, because he had seen her - he had tasted her. Ugh, why did last night happen? Eventually though, she heard chairs scrape and her brother spoke up again.

"You sure you guys can't stay longer?"

"Yeah, I've got to go home and finish homework, and I think Carlos has to help his parents with something." Jimmy said. Carlos nodded vigorously.

"Yeah, and I got work." Ben's monotone voice replied.

"Alright, then see you guys at school." her brother bade his friends.

"See ya'. And bye Gwen, can't wait to see you later tonight!" Jimmy said cheerfully at her.

She looked at him in shock. Did the little fucker really say that? Did he tell his geeky friends and her brother?

"Very funny, Jim! Hit on someone else's sister!" Her brother yelled after him.

"I'm kidding, I'm kidding" Jimmy laughed. He then winked at her and closed the door.

Her brother sat down with her at the kitchen table. "Hey, are you sure you're alright?"

"Yeah, I'll be alright." She said, "I just wanted to get away from Mat for a little bit, you know."

They sat there in silence. Then Ted spoke up again "I hope Jimmy didn't bother you too much last night."

She choked on her toast. "What do you mean?" She asked nervously.

"Well you know, his comments. I try to tell him to knock it off when he makes passes at you, but I don't think he means anything by it." Oh Ted, you poor, naive fool.

"No, yeah it doesn't bother me too much. If it did I'd tell him to stop." They continued to sit there in silence for a few more minutes when her phone chimed. In it, a message from Jimmy read: "Hey, my parents will be out all day and won't be back till tomorrow. Want to complete our little deal?"

She opened her phone wanting to tell him to fuck off, or some other similarly friendly greeting. But thoughts of his 7 inch dick flashed through her mind and the tingling in her loins returned. Fuck, she couldn't believe what she was about to do. She very much enjoyed her orgasm from getting eaten out last night (even if she didn't enjoy who it was that made her cum), but it wasn't the same as getting properly dicked.

"Be more discreet, dumbass. I'll be there later tonight. Let's just get this over with." She texted back. She knew what she had to do to get Jimmy to delete those pictures. She just wished she wasn't (slightly) looking forward to it. Thankfully, he was true to his word and deleted the pictures with her face. Now just get him to delete the rest.

At 10PM, she stood in front of Jimmy's door. Dreading what was going to happen. However, despite her supposed reluctance, she had put on a different pair of skimpy underwear and bra. She wore short shorts that she knew highlighted her ass and a tank top with spaghetti straps that exposed her midriff. A perfectly inconspicuous, if a little revealing, outfit in the current warm weather, but it could be easily removed when needed. Taking a deep breath, she rang the doorbell.

Almost as if he was waiting for her at the door, Jimmy opened it immediately. "Well hello, Gwen." He said grinning. His eyes drank in her fit body, from her defined long legs, to her toned stomach to her perfect cleavage. "Babe, you look ravishing as always."

"Stop calling me that. Now get out of the way before someone sees me here."

"No hello kiss for me?" He said with mock disappointment. She only glared at him and swatted him aside. He then led her inside and he shut the door behind her. "So, do you want anything to drink or just want to get down to business?"

"Ugh, you pervert."

"You know, Gwen, I think you're actually eager for this. You responded awfully quickly this morning and I can see you're wearing lacy panties under your shorts." he retorted. "Admit it, you were looking forward to sleeping with me. Mat not satisfying you anymore?" How the hell did he know all that? She wasn't sure if he was bluffing or not, but he was a lot more accurate than she would have thought he would be. She turned away, not able to look him in the eyes. But no matter what she may be feeling, she did not want to give this creep the satisfaction of knowing that he may, possibly, perhaps, might be, perchance, could be right that a part of her wanted this.

"Listen, Jimbo." She said, coldly, still not looking him in the eyes. "I'm only here because you blackmailed me with naked pictures of me. As soon as we have sex you're deleting those pictures and we pretend none of this ever happened."

Jimmy's face fell, slightly, but it was brief and he recovered quickly. "Very well, Gwen. You can pretend all you want, but I know I made you cum last night. And I could see you looking at my dick like you wanted it."

"Let's just get this over with."

"Gladly m'lady. Let's head over to my room."

She had never been to Jimmy's house before, much less his room. But it looked and smelled exactly like she thought it would. His walls were plastered with posters of geeky shit and slutty women doing suggestive poses. On his desk stood a giant bottle of lotion and tissues with a basket of used tissues next to his desk. It was the typical room of a geeky, highschool incel. Well, not an incel for long, unfortunately.

Gwen was shocked to see a picture of a naked woman pulled up on his desktop computer. She couldn't see the face, but she could tell by the shape of the body, the placing of the nipples on the breast and by a mole on the woman's thigh, that the naked body on Jimmy's computer was hers.

"Whoops" Jimmy said laughing. "Just making sure to study before the exam, you know how it goes." He moved to the computer and turned it off, still giving excuses. The little fucker knew what he was doing. The little fucker.

"Alright, ground rules, no coming inside me got it?"

"You bet." Jimmy said, already removing his pants.

"And we're only doing things I want to do. If I say 'no' or 'stop' you stop."

"Definitely." Jimmy removed his shirt.

"And lastly, no one can find out. That means no telling anyone, no pictures, no whatever."

"Yeah, yeah, I figured. Now let's make out." Completely naked, his dick already semi-erect, he approached her. "I've been wanting to fuck you for so long."

He leaned down and puckered his lips, waiting for her to kiss him. He definitely wasn't what she would call an attractive man. That, and the fact that she had known this boy who was 3 years younger than her, for almost half of her life, she would have never entertained the idea of kissing him. But the sight of his seven inch dick only reminded her how much she had been craving a good pounding. She tried to tell herself otherwise, but she could feel a tingle in her loins and she felt herself become moist. She could only hate that it was Jimmy the pervert who was making her feel this way.

She leaned up and gave him a brief peck on the lips. "Come on, Gwen, I could feel how hard you kissed me yesterday. Give me a proper kiss."

Making sure he could see her grimace at him, she stood up on her toes and kissed him more intensely. She was hoping not to use tongue, but a moment later his tongue snaked its way into her mouth and began playing with hers. His pudgy arms wrapped around her back, pulling her into him. His semi-hard dick once again pressed into her stomach and she had to shift it to slide between her thighs. The girth between her legs only fueled her growing hornyness.

After a minute, she felt him paw at her bra straps, but was unsuccessful in his attempts to remove it. "How the hell do you take these things off?"

Now it was Gwen's turn to smirk at him. "I'm only required to have sex with you, we never agreed that I had to be completely naked."

Without warning, Jimmy reached up and began fondling her breasts over her bra. Unfortunately, her low cut tank top and skimpy bra did little to hide her breasts, so he was able to trace his beefy finger over much of her skin. Gwen gasped, partly in surprise at the sudden sensation of her sensitive breasts getting attention, and partly to the pleasure of it. "If I remember correctly, you loved having your titties played with." He then slid his hand under her bra and began pinching her nipples again between his fingers. "Don't you want to feel me play with them again? To bite them?

Gwen did her absolute best to glare at him. To infuse as much venom into her stare as she could. But she knew she couldn't. Not with her tits being played with. Not with the idea of having her tits sucked again. Mat never played with her tits anymore. Still trying to glare at him, she slowly undid the clasp and threw the discarded bra on the floor.

"Now let's get this shirt out of the way." Jimmy said and began removing her shirt. Now completely topless, he took a second to ogle her then reached up and began fondling her tits. And Gwen moaned.

Without waiting for him to say anything, she grabbed his face and pulled him into a deep kiss. Gone was any reluctance she had about kissing the younger boy and she thrust her tongue into his mouth. He likewise ravaged her in the makeout, in pure anticipation for what they were going to do. He continued to pinch and flick her nipples. And she melted. Her own tongue lashed out and wrestled against his.

His hands found the lip of her short and quickly had them on the floor around her ankles. Now the only thing separating his dick from her pussy were sheer panties. For her part, Gwen's hands couldn't help stroking his penis, trying to get it as hard as possible, which didn't take much time. Their kissing remained passionate, only stopping when Jimmy pulled away for some air.

"My, my." The fat 18 year old said panting from the makeout session and looking down at her tight body, covered only by skimpy underwear. "If I didn't know any better, I would say you really are as eager as I am. That kiss was something else."

"I just want to get this over with, nothing else. The sooner you cum, the sooner I can forget this ever happened." She said. Any reluctance she tried putting in her voice was completely mitigated as she continued to stroke his penis. Jimmy only grinned at her and she knew he could feel her anticipation.

***

Jimmy still couldn't believe he was going to do it with Gwen. His crush and obsession for the past 7 years. He had spent many a night masturbating to her. And now she was staring at him with lust in her eyes. She wanted this. He leaned down and took a nipple in his mouth, eliciting sounds of approval from Gwen. He made sure to play with one nipple then the other so that neither felt ignored. Once both nipples were sufficiently serviced and slathered with his saliva, he began kissing his way down her toned stomach to her panties covered pussy. He reached up and slid her panties to the floor. Once again, he could only stare at her beautiful (and wet) pussy. He gave it a kiss and a lick then stood back up.

They stood there, both naked staring at each other. Her beautiful, dark nipples were just as he remembered, soft and firm. Her shaved pussy was on display for him again and he could definitely see her wetness dripping down from her lower lips. Oh yeah, she wanted it. It was a beautiful sight.

Then she stepped forward and wrapped her arms around his neck, pulling him into another kiss. She was the first to thrust her tongue into his mouth first and he could feel it explore his mouth again. He bent down slightly and gently picked her up and she wrapped her legs around his waist. He could feel his fully erect dick rest between the crevice of her ass cheeks, and could feel the warmth of her pussy.

He carried her to his bed plopping her down on it. He extracted himself from her arms and legs and began kissing and licking his way to her breasts. No way was he going to give up another opportunity to take in her whole body. He heard a familiar moan of pleasure as he bit down softly on her nipples. He then trailed kisses further down her stomach to her pussy, now displayed in full sight with her open legs. The scent wafting from her exposed vagina was intoxicating. He eagerly longed to run his tongue all over her pussy.

Jimmy dove for her clit with his mouth. He could feel her writhe beneath his tongue. He loved the taste of her and could eat her for hours and never get bored. He stuck a finger inside her as he continued to attack her clitoris with his mouth. She felt so tight and wet. He became giddy knowing his dick would be inside her soon. Above him, Jimmy could hear the college girl moan. The sound was so erotic.

"Jimmy" Gwen breathed. "Put it in me already. I want to feel your dick inside me." She was right, he had a goal. He couldn't get distracted by the taste of her.

He removed his face from her tantalizing pussy, his lips coated with her juices. He got into a missionary position and kissed her deeply. The thought that he went down on a girl and was now kissing her with her juices on his face felt so arousing. And she was into it. Gwen grabbed the back of his head and began licking his lips and forcing her tongue into his mouth. He felt ready to fuck her. He began maneuvering his dick to line up at her entrance.

"Wait." She got up. For a second, Jimmy feared she had changed her mind, until she bent over and without warning, engulfed his dick with her mouth. Never in his life had he felt something so wonderful. The feel of her lips as they bobbed on his dick. The feel of her tongue as she caressed his head. She licked up and down his shaft making to cover every inch of his big dick with her spit.

"Oh Gwen, your mouth feels so good." But all too soon, it was over. His dick now completely lubricated with her saliva. She laid back down and spread her legs. Her glistening pussy seemed to gape open, inviting him to enter her. Gwen's body looked divine, and her face looked at him with a pleading, lustful gaze.

"Jimmy, please fuck me. I want to feel your cock inside me." She moaned. Where was the girl who called him creepy? Where was the girl who punched him when she caught him looking through her underwear drawer? Where was the girl who told him that she and him together would never happen?

He lined his cock at the entrance of her pussy and slowly pushed the head of his dick into her. Holy hell, she was tight. Only the head was in, but he could already feel resistance to his girth. He pushed in slowly, reveling in the feeling of his first pussy. He pulled back his dick slightly then pushed in deeper. Again he could feel more of his dick entering Gwen and could feel the walls of her pussy clamp down around him. He had to pull back and enter her a few more times until he was finally able to push his entire dick into her warm, velvety pussy. All the while, he could hear Gwen moan and gasp. His dick now fully inside her, he grinned down at his accomplishment. His prize! He did it, he finally got to fuck his longtime crush.

"I can't believe I get to fuck Gwen Carpenter. Hey Gwen,how does my dick feel?"

"So good. Please fuck me already."

"Better than your boyfriends." He asked. When she paused, he withdrew slightly and rammed into her again, hard. "Am I better than Mat?"

"YES." She yelled, grabbing his sheets as her body shuddered. "I wish he was as big as you."

Smirking to himself he began pumping away at her.

***

Gwen was getting absolutely fucked. She could feel Jimmy's monster penis fill her entire pussy, rubbing every sensitive spot she had. His hips rammed into her. No dildo could hope to replace the feel of getting pounded like this.