winning-her-over
NON CONSENT STORIES

Winning Her Over

Winning Her Over

by septicalmrtestical
20 min read
4.59 (24100 views)
adultfiction

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

Gwen Carpenter slammed the car door closed and stalked up to her parent's house, fuming that she wasn't going to spend her Friday night getting fucked. Her stupid boyfriend had once again canceled their date to spend time with his new frat bros.

Gwen was a 21 year old college junior home for the weekend. She stood about 5 foot 6 and maintained a tight, fit body by going to the gym regularly. Her firm, perky B cup breasts and tight, toned ass garnered her lots of attention from the everyone, but especially the guys. She often wore her long, brunette hair tied in a ponytail to help exposed her toned shoulders. To accompany her body, she had a very pretty face with an easy, white smile and bright blue eyes. She was knockout, she knew it.

She and her jock boyfriend, Mat, had met their freshman year when they all lived in the same dorm building and had started dating within a few months. At first everything was peachy, exciting. He had been attentive and sweet. He would help her with English while she would tutor him in math and chemistry. Their sex life was awkward at first, as they had been each other's firsts, but they developed a nice rhythm.

But now that asshole was in a frat. He no longer put any effort into his school work. Where he used to make her laugh and feel appreciated, he had slowly become a proper douche. Their intimate sex had devolved into a pounding that only helped get him off. She knew it was his frat bros. Some were nice, but his Big was a typical red-pill, grade-A douchebag that was slowly poisoning his mind. Gwen knew deep down that if any of her girl friends were in a similar situation, she would have yelled at that hoe to dump his ass. But of course, her situation was different. She could change him. She had organized a nice lunch date at his favorite restaurant, ordered excellent tickets for his favorite team and bought the skimpy lingerie he had begged her to buy. A beautiful date for her jock boyfriend. She had put it on, under a short skirt and a nice coat, hoping to surprise him but peeling away her outer clothes, when she got a text (a fucking text!) with the first line "change of plans." Absolutely, fucking, not. Still dressed like a slut ready to surprise her man with sex, she got in her car and drove 45 minutes back to her parent's house.

She didn't know what to do with the jerk. He was her first serious boyfriend, and she knew he was still in there somewhere, but it was getting too much. She planned to take a break from her social life and just rot at home for the weekend.

She opened the door and was met with hollers and screams. Her younger brother, loser Ted and his loser friends from the chess club or anime club or whatever nerd club they were in, were sitting in the living room playing some video game with guns. At the sound of the door opening, a total of 7 heads turned in panic at her direction.

"Jesus, sis, I thought you were mom and dad. What are you doing here?" Her brother asked.

"None of your business, Ted." Fuck. She didn't mean to lash out, but she was pissed off at her boyfriend. Maybe she was pissed at all boys. "Sorry, Mat was being a dick, so I thought I'd come home for the weekend. Where's mom and dad?"

"I dunno, they said they were taking a trip somewhere for the weekend." Damn, just my luck. At least somebody in this family is getting action. They did this every so often. Spending the weekend away from their children to just enjoy a nice weekend alone, leaving the kids to watch the house. Gwen always admired how much her parents loved each other. She wanted that with her future husband, but now it just made her sad, thinking of Mat.

"I thought the parents said no guests while they were out." Gwen said, pointing around at his friends who all sat there sheepishly.

"Uh yeah, please don't say anything."

"Whatever, I'm going up to my room."

"Did you want us to beat up that asshole, Mat?" Ted said, half jokingly, half seriously.

"Love to see you try, nerds." She quipped, almost smiling. Mat was a 21 year old, 6 foot 2 football player who was one of those players that tackled people. Ok, she didn't know what the positions were, but he was big. While Ted and his friends were 18 year old D&D geeks. Ted, Carlos, Alex, Chris and Ben were your typical scrawny nerds without an ounce of muscle on them, while Jason and Jimmy were your overweight geeks - also without an ounce of muscle. She was quite confident Mat could beat all seven of them with one hand tied behind his back. But she appreciated the love behind his offer.

"Hey wait, Gwen." Jimmy, her brother's friend, spoke up as she started up the stairs to her room "If you want, you can chill here with us. I'll treat you right - better than Mat would."

"Ew gross, stop hitting on my sister, pervert." Her brother said slapping his friend on the shoulder, while their other friends just laughed.

"Never gonna happen creep!" Gwen called down to them.

"You sure, there's plenty of room on the couch. There's plenty of room on my lap!" He said, patting his massive legs. Gwen just stuck her middle finger at him and continued up the stairs. Jimmy had been hitting on her for 7 years, back when he had first moved to their little cul-de-sac. She didn't mind, usually, but it did get a little creepy at times. Usually it was just lewd comments. But she did catch him, going through her room and underwear drawer back when she was 16 and he was 13. To this day, he was the only person she had punched. With his nose bleeding, they had both agreed to keep what had transpired a secret to avoid BOTH of them getting reprimanded.

"Give it up, Jimbo, she is way out of your league." Gwen heard Jason, another friend of her brother's say.

"Shut up, man, at least I'm not too scared to talk to girls. How's it going with Nancy yet? Able to say more than two words to her yet?"

"Fuck off, dude. We're building a rapport."

"Uh huh, well while you're building a rapport with Nancy, I'll be making Gwen all mine." Gwen could hear Jimmy making mwah mwah mwah sounds like he was kissing. Thankfully, she was already heading up the stairs so was blessed to not see his pudgy face screwed up as if he were kissing an imaginary her.

"Gross dude, can we stop talking about my sister like that! And like she said, 'never gonna happen'" She finally heard her brother say over the roar of laughter from his friends.

"Whatever, I'll win her over." Gross. Ok, maybe he did say creepy things a lot. She never wanted to be 'won over'.

Gwen finally got to her room and closed the door. She dropped her bags to the floor and plopped onto the bed. That asshole! She wanted it to work with Mat, but he was changing into someone she didn't recognize. She didn't know what to do. In the safety of her room, she let her silent tears run down her cheek.

***

Eventually, Gwen composed herself and moved on to scrolling on her phone. Thankfully she was back to being pissed at Mat again. Sometimes, one just needed a good, hardcore crying session. Not only had he bailed on a wonderful date she had prepared for him, but he left her aching for a good fuck. Their love making these past weeks had been few and far between and had definitely failed to make her orgasm. She hoped today he would have fucked her passionately and loving like he used. But that wasn't gonna happen. And now she was horny.

She stopped hearing the sound of the TV from downstairs at about 2 AM and instead heard a rabble of boys leave the house. The boys must have stopped playing video games and were either heading out or had moved on somewhere. She crept to her door and opened it a jar. Fuck, there were still voices in the living room. It was 2 am, why weren't they going home yet.

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She was hoping they would be gone by now, but she had to do what she had to do. She really wished the boys had left, or at least that her door had a lock, but she was horny as fuck! She turned on her childhood relic of a computer and loaded up her favorite porn site. Browsing for longer than her masturbation would take, she finally settled on a generic video. The girl was cute and the man was muscular and huge. From her secret stash, she withdrew her oldest boyfriend, her vibrator. Ol' faithful. She started taking off her coat and pants when she realized she had never changed out of her skimpy lingerie. Fuck it, I feel sexy in this, she thought and crawled onto her bed in just lingerie, armed with vibrator.

The vibrator entered her smoothly and she let out a slight moan. It took almost no time for her to get wet. She focused on the sensation of the long dildo run up and down the length of her opening. Occasionally, she head would hit that sweet spot inside her and make her insides squirm. She could hear the man in the video groan and Gwen imagined the big strong man holding her and fucking her slowly and passionately instead. While her right hand pumped the vibrator in and out of her pussy, her left hand rose up to her lingerie covered breasts. Her nipples stood firm. When she massaged the fabric into her nipples, she loved the feel of the material as it tickled her breasts. She always had sensitive breasts, something Mat had known but had since stopped taking advantage of. No, fuck Mat! She opened her eyes to stare at the male pornstar as he rammed the woman from behind. The volume was low but she could hear their moaning. When was the last time she moaned like that? She felt the sensation build up in her. Her orgasm was bubbling to the surface and she was ready. Any minute now she would get pushed over the edge again, after so many weeks...

A knock at the door brought a wave of emotion, from anger... to fear... to excitement? Fuck fuck fuck FUCK. "Give me a sec'." She said a little too breathlessly. In a panic, she shoved her vibrator under her pillow and minimized her browser.

"Hey Gwen!" the little fucker, Jimmy said as she opened the door. She realized almost too late that she was half dressed in just lingerie so she just peeked her head around the door, obstructing his view of her body.

"What do you want?" She snapped, a little more harshly than she thought meant.

"Dang, sorry, Gwen. Carlos, Ben and I are having a sleepover and we ordered pizza. Want some?"

"No, thanks I'm good." She made to close the door, but he spoke up quickly.

"I wanted to say I'm sorry."

"What do you mean?" Gwen inquired.

"About earlier, you did seem upset over your boyfriend and I think it was a little insensitive to say what I said." He said sheepishly.

"Oh, yeah it was a little insensitive, and definitely creepy. But thank you for the apology."

"Are you feeling better or do you want to talk?"

"I think I'm ok Jimmy. I do appreciate it though, but I think I need to sort things out myself." Despite who she was talking to, she was genuinely touched. Jimmy had always been her little brother's pervy little friend. But they did know each other for almost 8 years and she did think of him as a friend. However, this touchy-feely Jimbo wasn't what she was used to and she narrowed her eyes and joked "You're actually a nice guy Jim, when you're not creeping. Better not let anyone hear you be nice."

Jimmy laughed and said "don't worry, the others are knocked out. They won't hear anything."

Gwen was about to bid him goodnight when a loud moan and a 'harder' sounded behind her. FUCK did I forget to mute my porn? She looked at Jimmy in alarm who stared wide eyed back at her.

"What the hell is that?" Jimmy said, still shocked.

"Nothing, just watching a movie."

With the panic of being caught watching porn and her masturbation session temporarily out of her mind, she quickly rushed to her computer to find the mute button. However in doing so, her door swung open giving Jimmy a full view of her body covered only a thin, almost see through bra and panties. The curves of breasts and the sway of her hips were on full display to her younger brother's perverted friend.

"Woah! Were you watching porn?" Jimmy's eyes bulged as leered her ass. His eyes almost looked in danger of popping out as he ogled her stomach and finally came to rest on her barely covered breasts. The outline of her dark nipples slightly visible under the fabric. "Holy hell, Gwen, you look hot. Why are you wearing that?"

"None of your business. Now get out!" She yelped attempting to cover her exposed midriff and barely covered breasts.

However, instead of leaving her to preserve any dignity she had left, he came into the room. "Why are you wearing only underwe-" He stopped mid sentence as he noticed her dildo peeking from beneath her pillow. "Oh my god, were you masturbating?!?" He said with absolute glee in his eyes. "You don't need to do that alone, you could have just asked me! Want any help?"

"Get. OUT." She yelped. She tried being as authoritative as possible, however it was a little difficult after being caught watching porn, dressed in her night clothes and masturbating.

No longer attempting to cover herself, she began trying to push the boy out of her room, while he only laughed saying other lewd comments.

"Get out" She repeated, now slapping his shoulder. If she couldn't push his pudgy body out, then maybe hitting him would get him to leave.

"Alright, alright, I'm going. Ouch." He started moving to the door while attempting to ward off her blows. She continued to hit and pull him toward the door.

As they neared the door, however, one hand covering his face, he reached out his other hand grasping for the door, Gwen felt his hand accidentally grab her boob instead! His large hands slid over her still erect nipples sending a jolt of electricity through her. In that moment, her sexual frustration and arousal came bubbling up to the surface again. And without any warning, she moaned.

Jimmy froze in shock. His hand still rested on her breast. "Did you just moan?"

She wanted to speak, but was afraid to open her mouth again.

"Sorry, didn't mean to touch you there." However he made no effort to remove his hand.

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After a couple of seconds, she felt brave enough to speak. "Didn't mean to make that noise. I was just surprised." They stood there in the doorway of her room, his hand still resting on her left breast, for what seemed like a minute.

He slowly spread his palm, fully cupping her right breast. His finger than traced the curve of her breast and came to rest, circling her hard nipple. And she moaned again.

"Jimmy, please. I'me very sensitive right now."

"Do you want me to stop?" He asked innocently. When she didn't answer, he reached out his other hand and began fondling her other breast as well. "Your tits feel amazing, Gwen. I can't believe I'm finally touching them." He said in awe.

She knew she had to stop him. This was creepy Jimmy! No way she wanted him anywhere near her breasts. "That feels... good." She breathed out, instead. He continued to fondle her breasts for a beautifully long couple of minutes.

***

Not wanting to push his luck too hard, Jimmy refrained from attempting to get underneath her bra. But he did begin to let his hands wander. His left hand continued to play with her nipple. Tracing around the tit and pinching them between his fingers, eliciting small moans. His right hand began to slide down her toned stomach. Tracing ever so tantalizing to her underwear and covered pussy.

Finally at his prize, he avoided her pussy and instead traced his finger down her upper thigh, then around her vagina to the other thigh. After a while, he couldn't stop himself and moved two finger to the growing wetness coming from her panties. Holy hell, she was WET! His finger became slick with her juices as he found what he believed to be her opening through the panties.

Gwen let out a noise halfway between a yelp and a moan. "Wait" She breathed weakly. "Not there."

Jimmy felt disappointed but wasn't going to let this opportunity slide. This was probably going to be the one and only time he would ever do this.

"Ok, do you just want me to massage your tits and thighs then?"

No answer from Gwen, just a moan as he pinched her nipple gently.

"Do you want to lie down?"

Ever so slowly, as Gwen looked at him with a horny expression, she nodded. He closed the door behind him and guided her to her bed, keeping one hand on her breast and the other gently guiding her to the bed. His finger was still slick wither her juices, so he stuck out his tongue and tasted her. It was faint, but what a taste it was. It was a little salty but tantalizing as hell. He silently told himself that he had to taste it from the source.

He continued to play with her tits and thighs while she lay on her bed, moaning. Jimmy would again trace his finger up and down her thigh getting close to her pussy, but never touch it. Every so often, his back hand would bump her pussy eliciting another moan. She would also spread her legs more and more giving him easier access to her panty covered pussy.

Jimmy drank in the sight. Not daring to believe what he was doing. He had dreamed about touching her all over like he was doing since he first moved here at 11 years old. Once he knew what sex was, he knew he wanted to fuck her. He had to push his luck now.

"I really like playing with your tits." He said after a long minute debating how he was going to pull this off. "Do you think it would feel better without your bra on?" He glanced up at her eyes and for a moment feared he had pushed too far. She stared at him with an expression he had never seen before on her. Slowly She sat up on her bed and began to remove the top portion of her lingerie. The top and bottom were connected, so she let the top fall to her side while keeping her bottom on.

"This is as far as it goes." She murmured, half-spiritedly as she lay back down. Jimmy on the other hand didn't hear a word she just said. His eyes remained glued to her bare tits. And what tits they were! He had only ever seen tits online. But the bare breasts in front of him at that moment were the ones he had been fantasizing about for years! Slowly, with shaking hands he enveloped her breasts with his hands, feeling his first bare tits of his life.

***

Gwen had a feeling she shouldn't have removed her top. But that bubbling feeling in her loins was taking control and Gwen was enjoying every touch. She closed her eyes and let the feeling of gentle hands caress her nipples and breasts fill her mind, unable to do anything else. But she wanted more, dammit.

She raised her chest into his touch wanting to increase the feeling but to no avail. She needed more!

"Bite them." She whispered before she could stop herself.

The hands stopped playing with her tits as Jimmy stared at her disbelievingly.

"You, you want me to bite your nipples?"

"Yes, bite them already!" She groaned, already missing the feel of her tits being played with.

Without further prompting, Jimmy the pervert bent over and took her nipple in her mouth. He bit, he licked, he sucked her nipple to her immediate pleasure. First the left, then the right all the while continuing to explore the rest of her body with his hands.

"Yes, that's it!" She moaned. No longer caring about who was touching her.

As his hand came up to her chest again, to massage the other nipple not currently being ravished by his mouth, she reached up and caught his hand. She dragged his hand below in the direction of her pussy. Her past declaration was completely forgotten or ignored, she directed his hands to slide underneath her panties. A crude finger slide over her clit, eliciting another moan "Can you touch me down here too."

***

Jimmy couldn't believe his luck as Gwen guided his hand to her pussy. He circled her vaginal lips with his finger, reveling in the slickness of her bare pussy.

"Put it in." She whispered. He had a clear idea of what he wanted to put in, but didn't dare mention it yet. His finger found her entrance with some difficulty. He was a virgin after all. And pushed two fingers into her tight, wet pussy.

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