- Everyone in this story is 18.
- Call this a work of speculative fiction. Everyone has those memories that their brains like to bring up, times when you did something dumb; this is a fictionalized, fantasy version of something that happened to me years ago, when I was too oblivious, insecure, and sexually hung up to actually follow through with a girl who clearly wanted to fool around with me. Names and the like have been changed, as have events - this was an effort to exorcise this memory through fantasy, but it ultimately is inspired by reality much more than it's a realistic account.
It was the summer after his senior year, and it sucked. It had taken until his senior year to really come out of his shell; he'd lost some weight, made a lot of friends, really enjoyed school for the first time ever, and had enjoyed his first serious romantic relationship. Then, the school year ended, friends were going off in all directions, and Rae had broken up with him because she was going out east in the fall, and he was headed to an in-state liberal arts college.
On top of that, his job situation sucked. His parents were driving him crazy. The breakup had splintered his friend group and, anyway, everyone was going different directions in the fall. At some level, he knew he had it pretty good, but he was bored and tired of having his schedule dictated, so he stayed up late most nights on the laptop he got for college, playing games, chatting with friends, and, let's be honest, looking at porn.
It was late June, about 11PM, and he was up to his usual routine when he got a message from a screen name he didn't recognize.
"Hi Matt! I got your screen name from Brandon, how are you?"
"Hi! Uh, who is this?"
Katie was the class valedictorian. She'd been competing with his girlfriend - no, sorry, his ex-girlfriend - for that spot, and had barely managed to lock it up late in the final semester. Despite her class rank, she had a reputation for being a little wild. He didn't know her very well, but when he was dating Rae, he'd felt obligated to casually dislike Katie. Now, he supposed, there was no reason to keep that up.
"Oh, I gotcha! I'm doing alright, how are you?"
"Oh, you know. I'm ready to get out of here." He chuckled sympathetically as she continued. "This summer is like purgatory. I'm bored out of my mind."
"You and me both," he replied. "I'm so ready to get out of my parents house. Where are you headed this fall?"
"Stanford! I seriously cannot wait," she typed. "How about you?"
He grimaced. Deep down, he knew he wasn't any less smart or capable than her (or Rae, for that matter), but he hadn't put in much effort his first couple years of high school, and his straight A's once the classes got interesting hadn't quite been enough to compensate. He tried to bluster it off.
"Oh, I'm staying in state at first," he pecked out, trying not to betray his insecurity. "I figure I'll get the basics out of the way where it's cheap and then transfer somewhere better."
"That's smart. Stanford's giving me a full ride, of course, but if not, I think I would have done the same thing."
He knew she was trying to be friendly - and lord knows he'd had this conversation about a hundred times this summer already - but it was not putting him in a friendly mood, so he changed the subject.
"I think we'll drive ourselves crazy if we spend too much time thinking about that, don't you?" He hoped he wasn't being too obvious. "Are you up to anything fun this summer in the meantime?"
"Ha, true!" she agreed. "No, not really. All my friends are drifting in different directions. I don't have schoolwork to spend time on anymore, obviously. I'm working part-time at my uncle's law firm, but that's it. You?"
Well, shit. This line of discussion wasn't much better. "No, I'm still doing my thing working at the bookstore, but I'm pretty much just twiddling my thumbs. Since Rae and I broke up, I haven't had much to do, either."
"I heard you guys had broken up. I'd say I was sorry to hear it, but I think you and I both know that I don't like her very much." A beat passed. "I'm sorry for your end of things, though."
This conversation was getting to be a real bummer. He was thinking about signing off and heading to one of his favorite porn sites when another message came through.
"Well, since we both have all this newfound availability, maybe we can find some entertainment," she said, with a wink emoji.
Oblivious to the flirtation, he replied, "I'd take just about anything, I'm bored out of my mind. Suggestions?"
Lucky for him, she was not to be deterred. "It's too late to plan anything tonight, but we could make this chat more interesting. How would you feel about some truth or dare?"
A twinge of excitement went through him, settling in his groin. What is she up to? After a moment, he couldn't see any harm in playing along. "Sure, I'm in."
Her response was almost instantaneous. "Alright then, truth or dare?"
He hesitated, but decided it was better not to show fear. "Dare," he typed.
After a beat, her dare came through. "I know you can't do it tonight, so we'll have to follow up on this later, but here you go: I want you to go buy the skimpiest little man-thong you can find and show me your ass in it."
She's not wasting any time, is she? As the brief moment of anxiety receded, a practical concern emerged. His boss hadn't had many hours for him this summer, so any fun money he spent came out of what he'd gotten for graduation. He didn't really know what that kind of underwear cost, but he didn't really want to pay for it.
Well, they always say honesty is the best policy. "I'm willing, but broke. How would you feel if I went commando instead?"
It took her a moment to reply. "I guess that'd be fine...as long as you're willing to prove it."
He wasn't sure what to do with that, but it seemed resolved for the time being. "Okay, sure," he said, doubting that she'd follow up. "I can do that. Your turn, then: truth or dare?"
She replied immediately. "Truth."
He thought for a moment. Well, two can play this game, I suppose. "Alright then, tell me about your first time." He didn't really know who she'd dated, but she'd surely been with someone.
A moment passed. "Hasn't happened," she finally responded. "They've tried - coming over, thinking they're going to get with some wildcat - but none of them have been worth it. Yet."
He was a little startled - frankly, it had never occurred to him that someone like her hadn't had sex. But there it was. He didn't have long to ruminate before her next message came through.
"You're up. Truth or dare?"
He didn't really want to pile up a big to do list tonight, so he figured he'd play it safe. "Truth."
She didn't hesitate to reclaim the upper hand. "How big is it?"
It's a good thing the computer was sitting on his desk, because he damn near fell out of his chair. Once he'd regained some stability, he realized that he didn't know. He'd never thought to measure. So that's what he said.
"Um, I don't know, really. It gets bigger when it's hard, obviously. I've never measured it."
She didn't let him off the hook. "Well, no time like the present!"
Before he realized what he was doing, he'd found a ruler in his desk and had started to unzip his pants. He paused briefly, feeling a twinge of guilt, then thought about Rae and the fact that her rival was asking about his cock. Something a little ugly - and a lot horny - reared up in his brain, and his hesitation ended. He slid his pants out of the way and pulled out his mostly hard member; a few strokes had it at full mast. He held the ruler against it.
Suddenly a new quirk arose. He didn't know whether he was big or small. Would she laugh at him? He was too deep now to back out, and too much blood had left his brain to lie, so he told her the truth. "Uh...seven, seven and a half inches."
She didn't respond for a moment. Then two passed. Was she angry? Had she lost interest for some reason? Finally, a reply: "Really?"
"Uh, yep. Really. I've got the ruler right here."
Another few beats passed, then her reply. "Hey, sorry, I have to run. It's late and I have work in the morning." Then she logged off.
He sat there in shock for a few minutes, hard cock in one hand, ruler in the other. She didn't log back in, and he was horny, so he wandered to one of his favorite sites, jerked off, came in about 3 strokes, and fell asleep.
The next morning, his dad woke him up at 11AM. He wasn't happy about it, but his dad insisted that they were going to go have lunch with his mom at noon, and then Matt had pool chores to do in the afternoon.
Grumpily, Matt got out of bed, and set about his prescribed activities for the day. He tried not to think too much about his conversation the night before with Katie. Unfortunately, an afternoon of scooping dead leaves out of a swimming pool doesn't offer much in the way of mental distraction. By the time he was finished and dinner rolled around, he was horny and irritable. He knew deep down that he probably wasn't being fair to his parents, but at 18, there wasn't much else he could do.
Finally, they went to bed, and he headed downstairs to his room.
He logged into instant messenger and was thinking about starting a game of Counter-Strike when Katie messaged him.
"Hey there! Sorry I left so abruptly last night - suddenly, I realized it was 1AM and I had to be at the law firm at 8. As it was, I fell asleep in the file room! How was your day?"
He was a little baffled at the superficial line of questioning, since their last topic of conversation was his penis, but he went with it, telling her about his irritation with his parents and the afternoon spent cleaning their swimming pool. Finally, in a lull in conversation, he seized the opportunity. "Want to resume our game from last night?"
"Alright," she replied. "Truth or dare?"
For a moment, he was annoyed. It's supposed to be her turn! There was no value in picking a fight over it, though. "Truth," he answered.
"You ever go skinny dipping in your pool?"
Somehow, he was still startled by the suggestive inquiry. Unable to come up with an alternative, he answered honestly: "Nope. It had honestly never occurred to me."
"Such a waste," she replied, with another wink emoji. He didn't miss the totally unsubtle flirtatious tone this time. An idea started to form. He took his turn. "Now you: truth or dare?"
She didn't disappoint him. "Dare."
He hesitated, old social scars flaring. Was this some kind of trick to humiliate him? Then he remembered his imminent departure. What the hell?
"I dare you to come skinny dipping with me."
A moment passed. It was probably mere seconds; it felt like hours. Then, her answer. "I'm in. When?"
He looked at the clock. 11:30PM. "Hang on a sec," he typed, and carefully crept to the top of the stairs. He could hear his mom snoring through their bedroom door; they were asleep. Trying to stay quiet, he hurried back to his keyboard. "Be here in 20 minutes," he sent, along with his address. "Park in the street, come to the gate, and be quiet. My parents are sleeping, and we can't wake them up."
He could feel her hesitation through the empty chat window, but she rose to the challenge. "On my way. See you in 20."
He stared at his computer, unbelieving. Was this really happening? He walked into his bathroom, and looked at himself in the mirror. He looked okay, he thought. A clean band t-shirt, khaki shorts. His shoulders were broad, and while he wasn't ripped, he thought he looked okay with his shirt off. He looked at his watch, and quietly slipped out into the backyard through the garage.
He didn't know how long he'd been standing by the gate, but it seemed like hours before he heard a car come down the street and park. His heart rate accelerated. He put a foot on a cross piece of the fence and peeked over. It was Katie. She closed her car door, careful not to slam it, then saw him wave over the fence. He opened the gate, willing it not to squeak, and let her in.
They stared at each other for a minute, breath a little heavy. He took her in. She was tall, lithe, blonde. A bit angular, with a sharp nose and dark eyes. Her breasts and hips were small, but present, and he thought he could see her nipples through her t-shirt. She caught him staring, but he recovered. "This way, and keep it quiet" he whispered, pointing upward "That's my parents' bedroom."
She nodded, and he led her through the dark yard, around the corner of the house to the pool. He was barefoot; she had flip-flops on. When they reached the pool deck, she kicked off her shoes and looked at him appraisingly.
After a beat, he realized she was waiting for him. "Uh...same time, then?" he inquired, grabbing his shirt to demonstrate his meaning. She nodded, and he thought he heard a hitch in her breath as she reached for the hem. He couldn't help himself, staring as she pulled the shirt off, her blonde ponytail bouncing as it slid through the neck hole. She wasn't wearing a bra; her nipples stood out proudly atop her small breasts; her slim body tapered enticingly to her waistline. She raised an eyebrow at him, and he realized he'd frozen with his shirt half-off. Hurriedly, he finished the job.
Then, watching each other, they both unfastened their shorts and peeled them downward. He caught a glimpse of blonde curls between her legs, then she was in motion, sliding into the shallow end of the pool. His foot caught in his shorts, so it took him a moment longer to follow suit. Finally, he gingerly lowered himself in after her, trying not to splash loudly.
He lowered himself until his neck and head were the only thing above water; she had done the same. In the dark, very little was visible below the water. After a moment, he stammered, "Uh...now what?" She stifled a laugh, then collected herself. He saw a glint of mischief in her eyes.
"You owe me a dare, I think," she said.
He was confused - what dare?
"From last night," she clarified. "You were going to go commando and prove it. I think this counts as commando, but you still have to prove it. Let's see that ass."
He was frozen for a moment, but he'd come this far. No sense not seeing it through.
He turned, rising up out of the water with his back to her. The water cascaded lightly off his broad shoulders, down his back, and as the cheeks of his ass emerged from the water he was a bit surprised to find he was hard as a rock. Then he heard her move in the water behind him, and, without thinking, turned.
He discovered that she'd moved closer, a hand outstretched. She'd meant to touch his ass, cup a cheek, but when he'd turned she ended up with his cock in her hand, hard and glistening with the pool's moisture. Her long fingers wrapped instinctively around it.
They both froze, a gasp of pleasure caught in his throat as she squeezed him. After a moment, he saw that glint of humor return to her eyes.
"I guess you weren't lying."
He was still in shock. "Lying? About what?"
Her eyes flicked meaningfully downward, and her fingers lightly squeezed his cock. "Looks like seven and a half inches to me. I thought you were making it up."
He didn't know what to say. His mind was overwhelmed with the situation and the sensation of a woman's fingers wrapped around his thick shaft. Finally, he croaked, "N...nope."
"It's so...thick, too," she mused, stroking it lightly.
Then, their eyes locked. Before either of them knew what was happening, he'd pulled her against him, their lips meeting, tongues exploring hungrily. Her hands wrapped around his back, and one of his found his way to her hard nipple. He tweaked it gently, and she gasped into his mouth. Encouraged, he kissed her harder, their hands roaming, his cock pressed hard against her abdomen.
As she ground against him, her arms drifted around the back of his neck, pulling him to her, as one of his hands drifted toward her ass. Unable to reach it as he wanted, he lifted her upward, out of the water. Instinctively, she wrapped her legs around him, her body sliding upward along his cock until suddenly he was poised at her entrance, the tip barely inside her.
They froze, panting, and eyes opened. He stared into hers, unable to form words, some part of him communicating his question, his desperate need for her consent, to be inside her. She must have understood, because she shifted slightly, resuming their kiss as she pressed downward onto his cock. As she slid, a moan escaped; neither of them knew whose it was.
He couldn't believe the tightness of her pussy wrapped around him. It was wet, slippery, and somehow still hot and tight. The feeling was overwhelming; he knew he wouldn't last long if this feeling continued. Then, mercifully, their hips met, and she froze, holding on for dear life, overwhelmed by the feeling of her body stretching to accommodate him.
He found her eyes, and his voice: "Are you alright?"
She nodded, and smirked as she began to work her hips, awkwardly trying to ride him as he held her on uncertain footing. He slipped, splashing, and they froze. A moment passed, and another, and a feeling of safety returned.
An idea occurred to him. He moved carefully to set her on the edge of the pool, allowing it to support her lithe body, never pulling out of her. He gave a gentle, exploratory thrust, and sensed her discomfort. He shifted his feet carefully, being sure not to slip, and she gasped as the adjusted angle hit something deep inside of her. He smiled; her ponytail had come partially undone; he threaded his fingers through the base of it. Then, with his other hand, he pulled her hard against him, sliding his cock in her to the hilt and kissing her deeply, his mouth muffling the resultant moan.
They wasted no further time, fucking frantically on the side of the pool, with only the tiniest thought given to the need for quiet. She could feel him hitting a spot deep inside her, and the feelings of pleasure built, and built. She knew what was happening, she had been masturbating for years, but this was different. She couldn't catch her breath, and broke the kiss, turning her head aside over his shoulder.
"Don't. You. Dare. Stop." she whispered loudly into his ear. "I'm. On. Pill." Finally, he drove his cock deep into her, and then ground his pelvis against hers. The sudden stimulation of her clit against his body put her over the edge; to keep from screaming, she sank her teeth into the meat of his shoulder. The sudden flare of pain and the feel of her spasming walls around him put him over the edge, and he came, hard, groaning as quietly as he could as he filled her with his hot cum.
They held like that, locked together, as they came down and caught their breath. Finally, the separated, his cum leaking out of her as his softening cock emerged. He kissed her again, but they both winced as their overstimulated bodies met. They reluctantly pulled apart, sliding back into the pool and catching their breath.
She looked at him, and their eyes met. He looked at her questioningly, but couldn't quite form the thought. The wildness and mischief returned to her eyes as she reached out and stroked his spent cock. "Worth it."