Tom was by no means an attractive individual; in fact, he was quite average, as far as he could tell. He was a little above average height; his hair was a dark brown, almost fully black, but he kept it clean and neat. He was also a bit of a shy nerd, as some of his classmates would describe him, and the description fit; he wouldn't really speak up in class but was part of four extracurriculars, none of which were at all related to sports of any kind. The only thing he had going for him was the size of his penis, but what use was that to him if he could never show it off, let alone use it? But that was all about to change.
The way one of the school bathrooms at Tom's high school was built made it so that the ceiling was significantly closer to the ground than any other room, only about two or so metres high. This meant that if you positioned yourself just right, you could stand up on the toilets without them breaking and reach the suspended ceiling; most people used this to hide vapes, cigarettes and other banned items from teachers, but it also meant you could look over the walls of the stalls into the rest. Of course, no one used them in such a way; why would you want to see other people in the toilet? Though it wasn't unheard of that people would record others pissing in secret and then upload it to Instagram for the rest of the school to get a laugh out of for a few days.
This risk had never really bothered Tom since he was already the laughing stock of most of the school, so he went anyway, and today was no different. Once the bell rang, signalling the end of his third lesson and the start of his break, Tom shoved his things in his locker and went to the bathroom. He actually preferred it here since most people would wait and use the more private bathrooms elsewhere, made all the better by the fact that the entrance was in an L-shape, meaning you could only see the entrance to the girls' bathroom from the corridor, leading to some of the new students not even knowing about this bathroom's existence.
There was no one else in the bathroom, so Tom decided to take his time and scroll on his phone for a bit; at least it would be a break from the yelling and bullying he'd get outside. That was when someone came in and entered the stall next to his. He thought nothing of it until he heard talking, and the strange thing was it was a woman's voice, and it sounded an awful lot like one of his classmates. He was sure he was in the men's room; he'd taken the right along the corridor and was sure he'd seen the urinal on his way to the stall, so why would he be hearing a woman? He thought about his two options: he could either simply ask if there was someone who had gotten lost, or, and this was the thought that made his heart race, he could stand up and take a look for himself. He chose option two, and he knew it was the right choice as soon as he peeked over.
Sat on the toilet in the stall next to his was Emily, his classmate. Her chestnut hair was in that beautiful, let-down and loose way he'd always found mesmerising in classes; she was wearing a hoodie, but it didn't hide her figure one bit. She wasn't the skinniest girl in the class by any means, but she was still quite slim, which made her breasts all the more distinctive. Her trousers were around her ankles, and she was muttering to herself about something Tom couldn't make out. As soon as she saw her, he let out a slight gasp, barely audible but enough to catch Emily's attention. She spun around to look straight at Tom.
"Oh my God, Tom, what the fuck?" She demanded from him, anger in every word.
"I- well, I just heard; I thought I'd check." Tom stuttered back, but truth be told, his eyes were somewhere else, and his mind had followed. As Emily turned to look at him, she had inadvertently given him a direct line of sight to her pussy, and he was making sure to take advantage of every moment.
She followed his gaze and clasped her hands and shut her legs.
"What the fuck, you creep?!"
"I- I'm sorry. I just, I didn't mean to."
"I know you're a bit of a loser, but I didn't think you were a peeping tom!"
"I'm not, I swear!" He protested, but it didn't help much in his current situation.
"How long have you been staring at me taking a piss? Oh God, don't tell me you have a fetish for that."
"No! I don't, I swear. You saw me as soon as I looked over. Seriously, is there anything I can do to make it up?"
"Oh, this is so fucked up, and no creep, there's nothing you can do to make it up to me, but how about this? You know what mutually assured destruction is, right?"
"Yeah, if you nuke me, I'll nuke you, and nobody wins."
"Exactly, so what we'll do," she said, as she reached down and pulled her phone out of her pocket. "I take a picture of your dick so that if you tell a single soul about this, I can post it, and trust me, this will stick more than any of the football teams cocks because you'll be the laughingstock of the school, well, more than you are now."
"Excuse me? What? No way! That's a huge violation of my priv—" he began before she cut him off.
"Oh, it's a violation of your privacy? As though you didn't disregard mine completely; shut it." She said before he could mutter any more excuses.
"Oh well, I suppose I'll just have to go to the vice principal."
"Wait! Ok, fine, you can take a picture, but please don't post it."
"I won't unless you start spreading rumours. What would I say if someone asked me how I got the picture?"
"Ok, true."
She pulled up the camera app as he pulled down his pants and pulled his dick out from his boxers.
"There, take your photo, and then we can both leave with some dignity." Then after a few seconds of silence, he said, "Emily, take that fucking photo and…" He trailed off as he saw Emily staring at his cock, eyes wide and mouth gaping.
"Emily?"
"Tom… Why didn't you ever tell anyone what a monster your cock is? It's huge! That's bigger than anything I've ever seen, well aside from porn, but that doesn't really count."
"Well, I'm never at any parties, or events, or anything really. I can't just go up to someone and say, Hey, want to see my cock?"
"That's true. Oh my gosh, it's so big; can, can I touch it?"
"Uhm, I'm really not sure that's something we should be doing in school," he began nervously.
"Oh, c'mon, I saw the way you were staring at me. Do you really want to pass up an opportunity like this?
"Ok, fine, but do it quickly before anyone else comes in."
As soon as he finished his sentence, she darted out of her stall and into his, dropping to the floor until she was eye-level with Tom’s cock. She reached out hesitantly, her fingers brushing against it before wrapping around the shaft and slowly beginning to stroke him.
Her eyes widened.
“Oh my God... you weren’t even hard that whole time?” She said, half in disbelief, half in awe.
Tom chuckled softly.
“Yeah, well… It wasn’t exactly the most thrilling experience of my life up to that point. And don’t get too excited; I’m more of a shower than a grower.”
She looked up at him, still stroking.
“That’s not a problem,” she said, voice low and hungry. “I’ve never seen anything that even comes close.”
As his cock began to stiffen in her hands, she started stroking harder and faster until Tom was at full mast. Then she pulled back his foreskin slowly, savouring every second of his head being revealed. She let out a small gasp once she peeled him back fully. Then, slowly, she gave his tip a gentle kiss, then another. After the fourth kiss, she ran her tongue along his shaft, swirling it on the tip a little.
"Uhm, Emily, should we really be doing this?" Tom asked anxiously.
"Shhhh," she replied before taking his cock in her mouth, slowly sliding along as far as she could go, and then she started sucking him off, taking in his cock as deep as it would go. Slowly pulling back, then she let one of her hands down to her zipper and started undoing it, revealing her tits and letting her hand wander down to her pants, reaching in and rubbing her pussy beneath her pants, all the while making Tom feel like he was in heaven. After a few minutes she was making progress, and he could feel himself getting close to cumming.
At that very moment, the door burst open, and both looked at each other with wide eyes. Tom recognised Dave, the football team's captain's voice as he said, "Alright, man, we only have a few minutes before class; I'll go get the vape from the ceiling."
Tom felt his heart stop beating; if Dave looked down while getting the vape, he'd have a prime view of Emily holding his cock, while she'd probably claim he had coerced her into it or something. In any case, his life would be over.
"Nah man, I got one in my jacket," said another voice, this one Tom couldn't identify but assumed he was also on the football team.
"Dude, what if Mr James asked you to empty your pockets in class? Are you crazy?" Came Dave's reply.
"Man, fuck Mr James; I don't care if he catches me; I'll just say it's my brother's jacket or something."
As the two of them started vaping, Emily started to clean herself up, and as the bell rang, the two jocks opened a window and walked off to go to class. After waiting for a few seconds to make sure they were gone, Tom opened the door and left the stall. Emily followed close behind. Just as Tom was about to leave the bathroom, Emily grabbed his arm.
"Wait, you know, that was pretty fun. Shame we couldn't finish what we started though, no?"
"Well, yeah, I guess so."
"Well, what's your number? My parents are going on vacation soon, and they'll be gone for a week."
So Tom quickly wrote his number into Emily's phone and hurried off to class, in disbelief at what had just happened. The rest of the day was a blur, and all he could think about was getting that text from Emily. Once he got home, he quickly rushed upstairs to his room, telling his parents he had a lot of homework on his way, locked the door and waited, and waited, and waited. Before he knew it, the time was already nearly seven, and still no text from Emily. Then, just as he was about to give up and conclude that it had all been an elaborate prank, his phone chimed. He lunged for it and opened the message. It was from Emily. It was short and simple.
"Parents leave tomorrow; be at my place at five. Bring condoms."
Immediately after, his phone chimed again, and it was another text from Emily containing her address.
The next day went by in a flash, and before he knew it, the day was over, the final four o'clock bell rang, and he rushed home to leave his stuff and pick up his condoms. He took a quick shower and put on his shirt, and drove off. As circumstances would have it, he only lived a few blocks away from Emily's house, but he couldn't bear the thought of walking all the way there.
Once he pulled into her driveway, he walked up to the door and, after taking a deep breath, rang the bell. After a few minutes, no one answered, so he rang again. This time, instead of the door opening, he got a text.
It was from Emily; it read, "Come in, the door's unlocked," followed by a winking emoji.
Tom could feel his heart beating faster as he turned the handle and pushed the door in. As he looked around the spacious and tidy living room, he couldn't see Emily anywhere.
"Emily?" He called out into the house.
"Up here, stud," came her sultry response.
Tom walked over to where the sound had come from and saw her standing at the top of the stairs, her left leg wrapped around her right and her arms stretching from door frame to door frame, reaching just slightly above her head. To call her outfit arousing would have been a gross understatement; she was wearing what looked like a waterfall of silk across her body, running from her shoulders to her waist, where it parted into two curtains next to her legs, and as she stood in the door frame, her dress hung from her arms like the wings of a majestic bird preparing to take flight. Tom could just barely make out the luscious mounds that were her breasts through the transparent material, but the finer details were obscured by the dark staircase. He had to take a few seconds to register the beautiful sight in front of him.
"Well, aren't you going to join me?" Emily asked as Tom took in her slender form.
"Oh, I- I-yes. I mean, of course!"
The words had barely left his lips when Emily lowered her arm and beckoned towards him with her fingers.
"Then come," her tone commanding yet gentle, and her voice sounding as smooth as the silk which clung to her body.
As Tom made his way up the stairs, almost breaking into a run from excitement, she turned around and walked off towards her room, swaying her hips enticingly as Tom followed.
Emily's room was on the second floor of their house, with the slope of the roof being apparent on the wall furthest from the door, on which was a window which also functioned as a skylight, beneath which was Emily's bed. It was covered by a white duvet and had a wall of pillows in front of the headboard; to the left, Tom could see a wardrobe running from wall to wall, not unsurprising since Emily almost never wore the same outfit twice in a month, and to his right was a neat desk with a computer. While Tom had been taking in the sights of the room, Emily had walked over to her bed and lay down on it, allowing the gentle moonlight from the window above to wash over her body and reveal her slender form. As Tom took in the sights from head to toe, all he could think was, "Damn, now I feel underdressed for the occasion."

"Oh, don't worry; I doubt we'll be spending too much time in these clothes," she responded, "Speaking of, why don't you get out of those pants? I'm sure they must be smothering your poor cock."
Tom didn't need to be told twice and quickly pulled down his pants, along with his boxers.
"Ohhhh." Emily let out a long gasp.
"It's so big; I remembered it being smaller." She said, starstruck, but with a huge smile filled with lust creeping across her face.
"Maybe it's because now I'm hard."
"Mmm, I can't wait to feel it in my tight little pussy."
The very words made Tom's cock twitch with excitement as he imagined her pussy swallowing his dick; he couldn't wait.
"Come here to the bed; I think it's about time I finished what I started yesterday."
Tom practically jumped into the bed and lay down, eagerly anticipating the wondrous feeling of his cock in Emily's mouth.
"Mmmm, it's such a nice, big, girthy cock," said Emily as she stroked her hand up and down his shaft, spacing each word to match the motion of her hand. As she kept stroking Tom's shaft, her other hand began to wander along her body, caressing her breasts before drawing a line with her index finger along her stomach to her pussy.
When her hand reached the end of its journey, she thrust a finger into her vagina while simultaneously dropping her head on Tom's cock, taking it in her mouth. As she carried out her double operation, she let out a slight moan of satisfaction before beginning to play with the enormous cock in her mouth.
After a few seconds she pulled her head up, and Tom could see her drooling a bit from her lips onto his cock; the thin strands of saliva were illuminated by the moonlight as though they were the web of a spider, except the only thing this web could catch was passion.
After taking a big gulp of air, Emily dove back onto his cock, continuing to play with her own pussy all the while, letting out small moans of satisfaction as she did so. Then, she pulled her hand out and began to stroke the exposed shaft with her hand, smearing it with her pussy juices, and began to gently massage his balls with her other hand until Tom let out a sudden groan and his cum exploded in Emily's mouth. Slowly Emily raised her head, taking one final long lick along his shaft as she did so, gently swirling it at the tip of his dick, before taking a few seconds to swallow his cum.
"Mmmm, delicious," she said seductively, looking into Tom's eyes as she did so.
"That was fucking amazing, Emily. Where did you learn how to do that?"
"Oh, just here and there, I read a few articles on the internet and watched a couple of porn videos every now and again. Oh, and I practised – lots of practice. At first, I just used cucumbers and things like that, well before I worked up the courage to go to a sex shop for the first time, and then I started using dildos."
"Wow, well, it shows that you had a lot of practice; damn, that was incredible."
"Oh, the night isn't over yet, stud; I've still got plenty planned for that cock."
"And I can't wait for it."
"Why don't I go get you a towel so that you can dry off and put on a condom?"
"Sounds like a plan if I've ever heard one."
And so she walked out of the room, leaving Tom alone on the bed, thinking about what he had just experienced. Never in a million years would he have thought that he would ever get laid, let alone in high school, by one of the prettiest girls in class, no less!
And yet here he was, lying on Emily's bed, his cock covered in a mix of her spit and pussy juice, getting ready for round two. Just as his dick began to rise again, Emily returned with a towel; she'd evidently cleaned up a little since her hair was loose and her lips dry. She gave Tom the towel, and he dried off his penis. The motions helped to get him back to full mast, and he rolled on the condom.
"Woah, that was quick. Are you that excited for this?" She asked.
"Absolutely, it's not every day you get to spend a night with a pretty girl named Emily."
"Stop, you'll make me blush!" Then, she got up, tossed her silky clothes off and to the side, positioned her pussy opening above his cock, and bent over. She leaned into Tom and gave him a slow and gentle kiss, then said, "Enjoy the ride, stud."
She lowered herself slowly onto his cock, gasping as soon as he entered her. She lowered herself gently, not going too fast, all the while breathing heavier and heavier, letting out small moans every now and again. Then once her hips reached the base of his cock, she exhaled.
"It feels so fucking good. I don't think I've ever been stretched this much."
She began to ride him, slowly lifting and lowering her hips, moaning and gasping as she went. As she got used to feeling him inside her and her pussy slowly stretched to accommodate his girth, she began to speed up her pace, giving out moans of pleasure every time she reached the base of his cock. She looked straight at Tom as she said,"How's this for a view, peeping, ahhh, Tom?"
In between catching his breath and letting out groans of pleasure, Tom replied, "Much better than anything I could see in a school bathroom."
Emily chuckled slightly and kept riding Tom until he could feel himself about to cum.
"Oh, I think I'm about to—"
Just as he was about to finish his sentence, his cock exploded for a second time, emptying his load into the small latex sock around his shaft. Just as the last of the cum drained out of his balls, his dick began to shrink.
"That was it?? You came so quickly; what the fuck?" Demanded Emily.
"Well, this was my first time; of course I was going to cum fast."
"What?! You were a virgin till today?"
"Well, yeah, of course, who would have slept with me? I don't go to any parties, football matches, bars – the list goes on."
"Still, with a cock like that? It feels like an honour to be the first person to experience that."
"Well, my left hand beat you there by about three years."
"Ew. That's gross; don't say that again."
"Sorry, but you know, I have more condoms; I just need a minute or so to rest."
"Condom or no condom, I'm not satisfied with that much; we're going at least one more time."
After a minute Tom rolled a second condom onto his cock and let Emily grind on it for a few seconds.
"Oh, my pussy's still so wet for your cock."
She lowered herself back onto Tom's cock, moaning as she descended onto his shaft. Once she reached the base of his dick, she began to rock back and forth, then side to side, then back and forth again, repeating those motions a few times before raising herself up and lowering herself down to keep rocking her hips along Tom's waist. Soon she'd settled into the rhythm and was beginning to pick up pace when she felt the condom bulge and Tom's dick begin to go flaccid again.
"Well, at least it was better than last time. How many condoms do you have left?"
"Just the one," he replied.
"Then I guess we better make that one count, or else I'm sending you to the pharmacy butt naked for more of them."
"Oh my, I suppose we'll have to make this count indeed."
"Ok, go clean up and get ready for round three; I'll give you a slight edge."
"How?"
"By masturbating for a bit now; at least that way I'll be closer to cumming when you return."
And so Tom left for the bathroom to take a quick break, and Emily put a pillow under her ass and began to circle the edge of her pussy lips. She kept stroking for a minute or so before she gently rubbed the outside of her pussy before thrusting two fingers inside. As she did so, she closed her eyes and imagined Tom's massive cock thrusting into her; she couldn't help but start moaning after a few seconds. It was strange; she'd been with some of the most popular boys in school, and even the ones with big cocks didn't make her feel this way. She was wetter than she had been for anyone else, and she enjoyed this sex more than she did with anyone else.
Was it possible that she was starting to like Tom? No, she dismissed the thought almost as soon as it crossed her mind; there was no way that she, Emily, one of the most popular girls in the class, was developing feelings for the biggest loser in the entire school, maybe in the entire town. It was just his massive member speaking to her arousal; yes, that was it. She was just horny and wasn't thinking straight, but she just couldn't shake the feeling that there was something different about him.
Just at that moment she felt a hand on her wrist, and her hand was pulled away from her pussy and into Tom's mouth.
"You taste delicious."
"How would you know if I'm the first girl you've ever been with?"
"Shhhh," Tom said as her parted lips felt Tom's thumb find them, while the rest of his fingers rested on her cheeks, except his pinkie, which he used to lift her head. She eagerly kissed his thumb before sucking on it. Tom took this as his cue to start using his one redeeming quality, his cock.
He gently rested the tip of his penis just above her pussy before sliding it down her pussy, making her moan while she sucked on his thumb. Then, when he found her entrance, he slowly pushed it in. This made Emily moan so loud. Tom thought for a second it was from pain before realising she was rubbing her clit at the same time. He kept pushing deeper into her pussy, the head of his cock rubbing against the roof of her vagina. Suddenly, Emily let out a huge moan, and her hips bucked.
"OH, yeah, right THERE."
She screamed the last word as Tom pulled back slightly.
"Is everything ok, Emily?"
"It's more than ok; it's perfect. You hit my G-spot; keep going; don't stop!"
And so Tom kept thrusting back and forth across the same region, whilst Emily's moans kept mounting in intensity, until suddenly she screamed as her hips bucked. Tom felt her pussy tighten around his cock, and then, after a few seconds of intense pleasure, she collapsed, panting. Tom kept going, but after a minute or so, he also came, and after cleaning up, the two went to sleep.
Early the next morning, Emily woke up, not entirely sure of where she was or what had happened. After taking a few seconds to wake up and look around, the events of last night came flooding back to her: the blowjob, the sex, and her orgasm. Her orgasm. Her first orgasm from sex. Somehow, Emily, who had been with so many guys more experienced than her and certainly more experienced than Tom, had had her first orgasm from sex with Tom. She thought it would only be right to pay him back for that, so she thought about what her best course of action would be, and after a few minutes, she settled on a plan.
Slowly and quietly she crawled beneath the covers until she was right in front of Tom's cock, and then, slowly, making sure not to wake him up, she began to kiss it, small gentle kisses all along his shaft. She could feel it begin to stiffen up in her hands, so she started using her tongue and then her lips before eventually taking it in her mouth and beginning to suck on it.
After a few minutes, Tom began to wake up, and she could see him looking around before noticing the movement under the covers; she could tell he'd decided to relax and trust the process. As she continued sucking, she felt his cock twitch, and she braced for the coming explosion of cum, and a few seconds later, her entire mouth was coated in his sperm. She emerged from under the covers and took a bit of time to savour his load in her mouth before making sure to swallow theatrically in front of him.
"Well, that was certainly a fun way to wake up," he said, smiling at her.
"I thought you'd enjoy it."
"Well, you were right; how did you do it? Did you read my mind??"
Emily giggled before saying, "No, but I was thinking about something. You know, it just seems so wrong for me to keep all of this amazing cock for myself," gesturing towards Tom's waist, "but it also feels wrong to just throw you to the wolves when you're so unprepared for the real sexual world. So my plan is I'll prepare you for all the sexual adventures to come, practise techniques, build your endurance, and act as a bit of a sex coach. But of course that wouldn't be free… So my proposal is for me to use your cock whenever I want it, wherever I want it, however I want it. Deal?"
"I think that's an excellent deal; I can't wait to start."