“Taking A Chance” A Sexy Short Story

07relationship

The following is a sexy short story about trust, taking chances, and believing that people can be decent and loving, even in sexy moments. I think it’s an important message that’s worth affirming every chance we get. Enjoy!

“Never trust men. They have too many reasons to use you.”

Sharon Kena had heard that mantra from her mother all her life. It was one of the first lessons she’d taught her as a kid and she belabored it every chance she got. It didn’t matter who she met or what she did. The message was always the same.

“Avoid men at every turn. If you can’t, make sure you use them before they use you.”

She said it so often that Sharon hadn’t given it much thought in recent years. She made it through high school without dating any men and none of her current friends were men. Sharon still dealt with them, but even the slightest interaction with a man was enough to draw scrutiny from her mother. At one point, she made a scene at an airport when the flight attendant made her sit next to a middle-aged man on a trip to visit her grandmother.

As mortifying as moments like that were, Sharon understood her mother’s sentiments to some extent. She knew, as well as everyone else in her family, that she had a bad history with men. Her father ditched her when she was a baby, her uncle abused her, and every man she’d ever dated found some way to hurt her.

Sharon’s own father was probably the one that went too far. He’d been so nice to her, treating her mother better than any of the abusive assholes she’d dealt with before. He was older, but claimed to love her. It wasn’t until her mother got pregnant that she found out she was just his mistress. Her father actually had another family across the state, complete with a wife and three kids. His wife apparently let herself go and he just wanted to sleep with a woman under 150 pounds.

Her father had used her mother and essentially abandoned her, even after she was born. Sharon was perfectly fine keeping him out of her life entirely, but he’d left such a deep scar on her mother that she went out of her way to inoculate her from such men. For the most part, she succeeded.

However, there was always that gnawing curiosity in the back of Sharon’s mind. Were all men really that bad? As much as her mother belabored that point, a part of her just couldn’t leave it at that.

“So…you want to come up and see my apartment?” Sharon asked in the most seductive tone she could muster.

“Boy, you sure like to skip ahead, don’t you?” replied the surprised, but intrigued young man in her presence.

“Is that a yes or a no?”

“Hell yes!” he said with a cocky grin. “For a girl as pretty as you, I’ll skip all the steps you want.”

Sharon replied with a half-hearted laugh. It couldn’t have been that convincing, but Chris Chadwin didn’t strike her as the kind of guy who cared. Why would he? He was about to get laid.

As Sharon latched onto his arm and led him up to her fourth-floor apartment, she could hear her mother’s voice echoing in her head, yelling at her to throw Chris out the nearest window. She was about to do something her mother urged her to avoid at all costs. She was going to willingly have sex with a man she barely knew, didn’t care for, and wasn’t even that attracted to. It was the antithesis of everything she’d been taught, but Sharon had already made her choice.

“I’m taking a chance, for once.”

That was what she’d told herself that afternoon, less than two hours before she accepted Chris’ offer to join him for happy hour at a bar not far from where she lived. It hadn’t been the first time he flirted with her. He wasn’t even the only woman he flirted with. He was just the easiest man to hook up with and that was all Sharon needed.

He was already getting frisky. As they ascended the stairs, he slipped his arms around her waist and playfully kissed her neck. Sharon didn’t care much for neck-kissing, but she appreciated the intimate grasp. The feeling of two powerful arms wrapped around her from behind was surprisingly arousing. It shouldn’t have been, given the influence of her mother, but it was.

“It’s just down the hall,” Sharon told him after ascending the final round of stairs.

“Lead the way, beautiful,” Chris said playfully.

He must have thought he’d charmed her perfectly. He had no idea of her true intentions and she had no plans to tell him. If Chris knew his actions that night might confirm or discredit everything she thought about men, then she wouldn’t be taking a chance.

Sharon chose to hook up with Chris because he was the kind of overly-macho flirt that her mother warned her about. He was a sophomore at the nearby community college who spent his weekends cruising bars, looking for pretty girls to get with. Some of the other girls who worked at the same software company as her had shared sordid stories about their encounters with him. Some showed regret. Most just shrugged him off as an arrogant meathead.

Whatever they thought of Chris, he still had a reputation as a guy who got more women than most. Despite not being exceptionally attractive or accomplished, he somehow managed to convince plenty of women to sleep with him. He never pretended to seek anything romantic, either. He was just a horny guy who wanted to have meaningless sex with pretty girls.

That fact, alone, didn’t surprise her. It was consistent with at least some of what Sharon’s mother warned her about. What still bugged her was the bigger implications.

Did he really just want to use her the same way he’d use a tissue to blow his nose?

Was she just a pair of breasts, a nice set of legs, and a pussy to him?

Did he only care about getting off and ditching her for his next sexual conquest?

Those were just some of the questions that Sharon sought to answer. All her life, she had only her mother’s answers to go on. For once, she wanted to answer those questions for herself. It meant putting herself at risk, but for her own peace of mind, she needed to find them on her own.

“We’re here,” Sharon told him upon arriving at her apartment door.

“Finally!” Chris said, still embracing her from behind. “These pants are getting really tight.”

“I think I can help with that,” she quipped, “so long as you return the favor.”

“Oh, don’t you worry!” he said boldly. “When it comes to ladies and favors, I know how to prioritize.”

His bravado was obnoxious, but the sentiment was endearing. Sharon even managed a genuine smile, if only to give Chris incentive to honor his word.

She could already tell he was plenty motivated. With the way he rubbed up behind her, she could feel the bulge in his pants pressing up against her. He was horny, that much was clear. He wanted sex and he wasn’t afraid to be crude. Sharon was willing to tolerate that, provided he didn’t confirm too many of his mother’s warnings.

Upon entering her apartment, she didn’t waste time. Before she could second-guess her choice, she led him into her bedroom. There, she finally turned around and let every reckless whim guide her.

“Want to help me get out of these itchy clothes?” she asked him.

“Of course!” Chris said eagerly. “Isn’t that what a gentleman does?”

Ignoring, for the moment, how little he had in common with a traditional gentleman, Sharon let him strip her as they made their way to the bed. He was surprisingly courtesy in that he didn’t rip her clothes off like her mother said men would if she gave them the chance. He was almost gentle in how he slid her pants down her legs, even teasing her feet as he laid her down on the bed.

“Simple, brand-name underwear,” he commented up on seeing her in her bra and panties. “I like it!”

“You probably say that to all half-naked women,” Sharon said.

“You’d be surprised.”

He might have been right about that, but Sharon tried not to overthink the situation. She just watched as Chris shed his clothes, as well, removing everything but his boxers. He then joined her on the bed, getting on top of her gazing upon her with a lust she’d been taught her whole life to avoid.

“You ready for the main course? Or do you need some appetizers?” Chris asked, sounding like every bad porno she’d ever seen.

“It’s uh…been a while for me,” Sharon told him. “I might need a little extra care.”

“No problem!” he said confidently. “I don’t mind going the slow and steady route.”

Sharon replied with a flirtatious grin, hiding the fact that she had never let a man touch her in such an intimate way. For much of her life, the thought of letting any man put his hands on her like that was abhorrent. She had to set all that aside, if only to give Chris – and men, as a whole – a fair chance.

It wasn’t like she had avoided all sexual activity. Her mother – most likely in an effort to keep her away from men – actually bought her a vibrator when she was a teenager. She even let her watch porn, although she only tolerated lesbian porn. In her youth, that had been plenty stimulating. She’d even had a sexual relationship, of sorts, with a lesbian woman at one point.

Even though her mother had been vocal with her approval, something about it just didn’t feel complete. It was as though she’d only ever explored half of her desires, at most. At time went on, men found their way into her sexual thoughts, so much so that she couldn’t shut them out.

Chris wasn’t the first man that had evoked sexual feelings in her. He was just the most convenient way to explore those feelings. In her mind, if she could still experience pleasure with a man after everything her mother had done to demonize them, then that would go a long way towards proving her wrong.

“Just lie back and let me work my magic,” Chris said as he guided her to the center of the bed. “I think you’ll find I know my way around the female body.”

“That…would be surprising,” she said under her breath.

Despite all the factors urging her to do otherwise, Sharon went along with the horny man’s lustful request. She soon found herself lying flat on her back, resting her head on her pillow, as Chris got on top of her and went to work.

It started with a simple make-out session, his lips smothering hers with his sensual hunger. Somewhere, along the way, he removed her bra and trailed his lips down her body, paying extra attention to her breasts. He kissed her exposed flesh, again showing a surprising amount of care. He wasn’t trying to devour her as much as he was trying to savor her exposed flesh.

At first, it felt strange. Before long, though, it felt good.

“Mmm…you taste good,” Chris said, his voice muffled by her breasts.

Sharon replied with light moans, but didn’t completely succumb to the same lust. However, that quickly changed after he removed her panties and got his first taste of the tender womanly flesh between her thighs.

“Ooh!” Sharon gasped.

“Whoa!” he said. “It has been a while for you.”

He had no idea and Sharon didn’t intend to let him know. She’d presented herself as someone who regularly took guys up to her apartment and fooled around. She needed Chris to believe that in order to make all the risks worthwhile. Near as she could tell, he wasn’t overthinking the situation.

He was just touching and tasting her naked skin, as though it were a succulent treat. After tossing her panties aside, his gaze narrowed on her inner thighs. She even noticed him licking his lips in anticipation.

“That’s a nice-looking pussy you have there,” he commented. “Mind if I have a taste?”

“Please,” Sharon said, as though it were the most polite thing in the world.

With a dazed, but eager look on his face, the young man pushed her thighs apart with both hands and indulged in her womanhood. His eagerness, alone, surprised her. Sharon had been led to believe that men only liked receiving oral sex and rarely gave it. Even if Chris was an outlier, there was no denying his demeanor. He was a man and he enjoyed eating a woman’s pussy out.

That was jarring enough, but Sharon didn’t care. His efforts did exactly what she needed him to do. He was not too coordinated. He wasn’t overly-thorough, either. That didn’t matter, though. Chris showed he knew enough about female anatomy to get her juices flowing in ways that directly countered her mother’s warnings.

“Ohhh yeah!” she moaned. “That…that feels good.”

“Mmm…you almost sound surprised,” he teased, briefly looking up from her inner thighs.

He had no idea how big a deal it was for her. The idea that a man actually enjoyed something that gave a woman direct pleasure just didn’t fit with her mother’s narrative of men being selfish pigs. While her mother would’ve argued that Chris had only gone down on her to ensure he got what he wanted, Sharon couldn’t accept that something that felt so good could be that selfish.

As enjoyable as it was, she picked up on Chris’ secondary agenda. While giving her oral sex, he’d been pleasing himself as well, getting his manhood nice and hard. It was the most effective act of multitasking she’d seen in any man to date. Regardless of how her mother viewed men, Chris proved that they could stay focused when motivated.

“God, I love the taste of a hot, moist pussy,” said Chris after giving her outer folds one last lick.

“I love that you love it,” Sharon teased. “Your generosity is…appreciated.”

“Just doing what I got to do to make the next part easier for both of us!”

With a curt grin, as if to flaunt his manliness, he rose up and removed his boxers, revealing a fully-erect penis that looked ready to enter a willing vagina. Her mother once told Sharon that any penis attached to a man was inherently repulsive. Chris might not have been the most attractive or endowed man she’d ever seen, but the sight of his manly physique hovering over her did plenty to fuel her arousal.

“You ready?” he asked as he loomed over her with lustful intent.

“Are you asking me? Or telling me?” she teased.

“Only if you’re anything less than ready for some fucking!”

“Then, I guess that depends.”

“On what?” he asked intently.

“On just how good you can make it!”

It wasn’t just a flirtatious quip. Now clutching his shoulders, gazing up at him with burning desire, she dared him with her eyes to prove himself. He didn’t have to completely disprove everything her mother had ever taught her about men. He just had to demonstrate that he could give a woman quality, enjoyable sex. Chris, meathead or not, seemed up for the challenge.

“In that case, I’d say we’re both ready!” he said confidently.

“Less talking…more fucking,” Sharon said intently.

There was no turning back. At that point, she’d given Chris free reign over her naked body. He could drop the façade and use her like his personal fuck toy. He could also demonstrate that even a horny man getting what he wanted could be trusted to that extent. Sharon was about to find out.

Instinctively, she braced herself, closing her eyes and taking a deep breath. She felt it as Chris’ upper body made contact with hers, his manly sinews meshing with her feminine curves. As naked skin meshed with naked skin, he tightened his grip on her thighs, holding her legs apart as he guided his rigid manhood to her womanhood.

Then, with a thrust of his hips, he entered her.

“Ohhh yeah!” Chris moaned. “So hot and tight…you like that?”

Sharon replied with a sharp gasp. That was all she could manage. She genuinely struggled to process the feeling that had just washed over her. She’d been led to believe that any act that involved a man penetrating a woman with a body part could only be uncomfortable. While it hadn’t been disproved entirely, she already found herself questioning that assumption.

Chris didn’t wait for her to finish processing it. He had already begun moving his body, burying his face in her neck and working his dick within her tight folds. He wasn’t too rough, establishing a steady pace of sex. It didn’t completely rock her world, but it certainly rocked the bed enough to remind her that she was really doing it. She was having sex with a man, despite her mother’s efforts.

“Wow! This feels good…no, great!” Sharon proclaimed.

She sounded even more surprised than she did before. Chris didn’t seem to notice, though. He was too focused on their sex, thrusting his hips and caressing her naked body. It was so hot and intimate, his naked skin gliding against hers, masculine sinews meshing with feminine curves. It wasn’t supposed to be so intoxicating. It was just supposed to be sex, but it quickly evolved into something else.

As Chris maintained the sexual rhythm, Sharon found herself supplementing his efforts. She acted on a mix of instinct and lust, raking her fingers down his back and arching her body in just the right ways every time he drove into her. The feeling of his hard, manly flesh slithering inside her stimulated parts that she didn’t know existed. Even a vibrator could only do so much. There was just something different about an actual, throbbing penis in conjunction with a man’s body.

It felt so good that Sharon expected it to end abruptly. She’d heard plenty of jokes about how men barely make it beyond the first dozen humps before they blow their load. Chris didn’t seem that eager to rush the experience. It was easy to assume that he just wanted to show off his prowess so that he could brag to others who good he was in bed. However, it was just as likely that he wanted to draw out an inherently pleasurable feeling and Sharon was more than happy to let him.

“You…are so sexy,” Chris said into her ear, part of his face still buried in her neck.

“And you’re so…considerate,” Sharon gasped, still struggling to form words.

“Considerate? I can do better than that!”

Chris seemed to take that as a challenge. At first, Sharon worried that she’d said something wrong. For all she knew, the best parts were over and everything from that point forward would prove her mother right. Once again, she braced herself.

In another display of bravado, he rose up slightly so that he was in a more upright position. Her legs still hooked around his waist, he began humping her at a different angle. However, he threw a little something extra into his efforts. As he worked his manly flesh within her depths, he used his thumb to stimulate her clit. Either the man had just paid extra attention in health class or he genuinely cared about bringing a woman to orgasm.

“How’s that? Is that better?” he said with a cocky grin.

“Oohhh!” was all Sharon got out.

Her body reacted before her brain could process everything. She grabbed hold of the sheets, closed her eyes and panted heavily as a flood of powerful sensations shot through her. What they’d been doing before had been pleasurable, but it only took her so far on the path to ecstasy. That extra effort, stimulating her most sensitive areas with such determined care, sent her down the rest of that blissful with stunning efficacy.

At that moment, another profound realization sank in. She wasn’t just having sex with a man. She was going to achieve orgasm with one of them. If that weren’t astonishing enough, a man was going to give it to her. If there was a more effective way to shatter her old assumptions about men, she hadn’t heard of it.

“Like that! Ohhh just like that!” she gasped, increasingly short of breath. “You’re going to make me…I’m going to…ohhhh yes!”

That orgasmic chorus filled the room. There was nothing fake or exaggerated about it. She experience a real, toe-curling orgasm. Every muscle contraction and blissful sensation carried more meaning than usual, as if to directly counter every man-hating rant her mother had ever made.

“The sound of a woman coming,” Chris said, “I never get tired of that!”

He still sounded arrogant and crude, but Sharon didn’t mind. He’d just giving her an orgasm. He earned the right to brag. Logistically speaking, it made too much sense. To back up his bravado, he had to give her great sex. To give her great sex, he had to do it in a way she enjoyed. He got what he wanted. She got what she wanted. It was almost like sex was a collaborative effort.

Sharon would’ve laughed if she weren’t still processing the ecstasy. She was content to just soak in the feeling while Chris pursued his own peak. He kept the pace of their sex slow, shifting his grip to her butt and giving it a firm squeeze as their naked bodies moved together in blissful harmony. By the time he neared his peak, Sharon had completed her orgasmic journey. In doing so, she opened her eyes and watched the man before her complete his.

“Almost…there!” Chris grunted. “Just…a little…oh fuck!”

His orgasm wasn’t as theatrical as hers. After a few more targeted hips thrusts, his expression contorted and his grip on her butt intensified as he got his release. Sharon even felt it as his cock throbbed inside her in accord with his release.

Her climax directly led to his.

Her pleasure became his pleasure.

Inside her, the juices of their sex blended together, their shared ecstasy taking a tangible form.

“I feel it,” Sharon said distantly. “Inside me…so nice and hot…I really feel it.”

She doubted Chris heard him. That look on his face – the O-face that she once joked about, no less – made clear that he was in too blissful a daze to hear. That didn’t matter, though. Whether he knew it or not, he just changed everything she thought she knew about men.

When he finally opened his eyes, that post-orgasmic afterglow already setting in, she made it a point to cast him an affectionate smile. He smiled back, still looking dazed, if not somewhat goofy. That didn’t stop her from drawing him back into an embrace and giving him a kiss.

“Thank you, Chris,” she said to him intently.

“For giving you the good fucking I promised? You’re welcome!” Chris replied proudly.

He laughed as their naked bodies finally parted, exhaustion and satisfaction settling over them as the room fell silent. Sharon smiling, though. Chris might have been arrogant, crude, and immature. From his perspective, he just banged a pretty girl and did it well enough to ensure she enjoyed it. That was as meaningful as their sex had been for him.

For her, however, the meaning went beyond the sex. Chris was not some dignified gentleman. He wasn’t some thick-headed brute, either. He sought sex with a pretty girl and getting it didn’t mean using her, as her mother often warned. In fact, that would’ve made it harder to achieve the satisfaction they’d shared.

She trusted him with her body.

He rewarded that trust and she rewarded him back.

A man she barely knew, who only wanted sex, proved that she could trust a man. The end result wasn’t just great sex. It was definitive proof that her mother had been wrong.

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