Hey readers! My name is John, if you're my parents or teachers. If you're my friend, I'm Jack. This story is true up until the day where I lose my virginity (yeah, I'm still a virgin). Everything after that is just one of my recent jerk-off fantasies. I was describing it to my friend a while ago and he said I should write it into a full story. So here it is!
If you want me to write a sequel to this story, or write another one, or tell you more about myself, or just want to talk, email me at jacksta@ymail.com.
Perfectly, beautifully unapproachable Samantha
There she stood. Long, flowing blonde hair. Perfect symmetric face. Lovely pink lipstick. Firm high tits. Thin white blouse showing just a bit of her stomach. Tight white short shorts showing off a gorgeous ass. Perfect, beautiful Samantha. Talking and laughing beside her locker with some other girls on the cheerleading squad. Perfectly, beautifully unapproachable.
I know she's not nice. She spits on twerps like me. Slaps us if she catches us even glancing at her chest. That's why I can never look long. And I really shouldn't like her. But I can't forget about her physical perfection. I should just call her a bitch, but instead I think I'd do anything she asked. If she told me to come to school naked to embarrass me, not only would I do it, but I'd do naked jumping jacks in front of the entire school. Sometimes I hate myself more than I hate her... but those tits...
Shit. I thought about her tits too long and now my dick's hard. And you know, getting a boner in school is hard enough, but getting one when your dick one of the longest and thickest out there just fucking sucks! I can't just hide it by putting it down a pant leg and carrying some books around. Managing a hardon takes work!
And I'm sure I know what you're thinking! What right do I have to complain, the boy with the massive cock? Well, if you must know, I'm still a virgin. I don't think a girl has ever seen my dick! Not since puberty started anyway. In my mind I've fucked the entire cheerleading squad, but in real life, having a big dick doesn't make jerking off all that much more fun. And the looks on my friends' faces when I change clothes facing them on sleepovers is priceless... but that's still not good enough. Right now it's a nuisance. Maybe someday in college I'll be the big man on campus and the girls will all line up to take a turn riding the monster, but I'm 15 now. No good thinking about things still years away. Especially when I'm trying to lose my erection during school hours!
Too late. It's not going away on its own now. I need to take care of it. The boy's bathroom on the upper floor has the least traffic this period. If I can cum in under 5 minutes, I can usually get out before any other boy walks in. That's really important because, if you hadn't guessed it already, I jerk off at the urinals, not in the stalls like most boys! I check under the stall doors for unwanted company, then walk to the far urinal and pull my dick out. Already hard, I start stroking fast right away. No easing into this jerk off session!
I try to keep my mind off her, and on more sensible fantasies. But I can't. I can't think about anything but ripping her top off and sucking on her nipples. Licking on down to her totally shaved pussy. Rubbing my rock hard cock over her pussy lips as she moans. Pushing it inside until... Shit! Footsteps. I freeze as another boy walks in and starts peeing a couple urinals down. Shit Shit Shit! I know him! It's Chris. I can't just wait for him to walk out because he might figure out what I'm up to. So I do the only thing I can do... I quickly tuck my dick up and button my pants over it. I really hate doing that, but it's the only way to hide it when it's that hard. At least I remembered to wear a longer shirt that day!
So... I guess I'm off to the bathroom on the main floor! This time I have this! The bathroom is empty and I'm only a few strokes away from cumming. One more thought about her pussy and... mmmm yeahhhhhh. Even the quicker orgasms still feel amazing! Six shots of cum dribble off my dick and land in the bottom of the urinal. Thirty seconds later, I'm shoving my softening cock back in my pants, and I stroll out of the bathroom with a sigh of relief.
I probably should fill you in on some details I left out about Samantha. About why I spend so much time fantasizing about her, and not any of the other equally pretty cheerleaders. It's hard to picture sex when you've never had it, especially with a girl you've ever seen naked. Try to fantasize about it, and you just end up picturing the last porno you watched! What makes Samantha different is that I've seen her naked. Not in person, of course, but in cell phone pics. See, at the beginning of the year, one of us twerps stole James's phone during a game. Yeah... that's her boyfriend, and yeah, he plays football. Typical!!
But what we found on his phone was not typical. Seriously, this guy must want to be a porn star! He had naked pictures of himself from every angle, and maybe a dozen videos of him jerking off and cumming. But that wasn't the real jackpot we found! Amongst the hundreds of pics of him naked, we found a couple of her. Tits, pussy, everything! That moment was one of the most magical in my life. Seeing a girl you know naked for the first time isn't something you forget! And what's more, we found in their text messages everything about their sex life. They were discussing positions and schedules and even the possibility of a sex tape. So they were fucking! We weren't sure we believed they really were until we read in her own words that she preferred reverse cowgirl over forwards cowgirl and that missionary was getting boring. Who knew!!
The last time we took his phone, we even found a couple pics of his dick inside her pussy! Every time we kept hoping for that sex tape, but it hasn't happened yet. But we keep checking. We even took to calling ourselves the Boys Under the Bleachers. That name stuck even though we don't actually steal phones by hiding under the bleachers. We get them from the lockerroom during the game. Fortunately, their coach makes them leave their phones in their lockers, and fortunately, he left his lock's combo sticker on the lock, and fortunately, one of us spied on James to get his phone password. We basically have the whole game to look through his phone. We could even have a circle jerk in there, if only so many of them weren't afraid of getting caught. So we just pass his phone around and remember what we saw for later.
So that's why I can't stop thinking about her when I'm jerking off... I can picture her naked so easily. Some day maybe I'll find naked pics of a girl who isn't a total bitch. But then I guess I'd feel guilty about it. At least with Sam, I want to punch her almost as much as I want to stick my dick in her. I want to slap her boyfriend too. He's as much of an asshole jock as she is a bitch cheerleader. But I guess I don't want to stick my dick in him as much, haha!
I really should get my mind off them. It's late now, and I still need to jerk off before bed. Fortunately, tonight I can distract myself with porn. My current favorite: those Russian porn videos where a guy rents his girlfriend to pay his own rent, and has to watch a pretty rich boy bang his girlfriend in his own bed. I have no idea whether they're real, but it's pretty hot assuming that they are. Ten minutes later, I'm catching five shots of cum in my hand. A minuter after that, I'm wiping the sixth shot up off the floor. Two minutes later, I'm crashing naked on my bed.
The next morning felt very normal. I should have guessed that it would be a special day, but I didn't. Morning routine was normal. Squeezed in a quick jerk off session in the shower. Normal horseplay on the schoolbus, uneventful classes. But at the end of science class... there was a hand on my shoulder as I was getting up to leave. Of course, I knew who it was. She sits in the row behind me, two desks to the right. But I didn't believe it till I saw her looking straight at me. And she had a worried look on her face.
"You're good at science, right? You know all this stuff?" It was weird to see her talk to me, instead of looking down on me disdainfully.
"Uhh..." was all I could get out.
"I really need a tutor. Do you think you could help me out?" This was surreal!
"Well... I guess..." I wasn't getting more coherent.
"Thanks! Meet me in the cafeteria after school!" She touched my nose for a moment before walking out.
I sat in stunned silence for a minute. I managed to reassure myself that this was reality and not just my mind playing weird tricks on me, and left the room. But it was still all I could think about for the rest of the day. I couldn't tell you what any of my other classes covered. And I think I missed my friend making a joke at my expense at lunch about my dick or jerking off or something. When the last bell rang, I went straight to the cafeteria. And there she was... sitting totally alone at a table, with her textbook and notes out.
I walked up behind her, but found it hard to work up the nerve to say anything. I probably stood there for five minutes just trying to control my breathing. But then she stretched a bit and saw me, and I couldn't pretend I wasn't there anymore. So I nervously sat down at the table, and just let her talk.
"Hi, John." Of course she called me what the teachers called me.
She rambled on for a couple minutes about how she was headed for an F in science class and she'd get dropped off the cheerleading squad and could even be forced to repeat the grade. I almost smirked at the idea of her getting the punishment she probably deserves, but then she offered to pay me money. Normally the idea of getting paid would be funny. Most people have no pity for the boy from a wealthy family who gets basically no allowance. But I actually had assumed up until now that she was just gonna ask me to tutor her for free. Like it was such a privilege to be around her. But no, this was actually serious. She was in trouble.
At that moment, I had a thought. And I summoned up all the courage I've ever had in my life, and told her, "I can tutor you if you pay me, yeah. But it won't be in money."
"Oh great! I really need this. But what do you mean it won't be in money? It... ohhhhh," it suddenly dawned on her.
My mind was racing. Did I really just ask her to offer sex for school help?
After a moment, she continued, "But we can't do it here! We'd get caught!"
Shit! My heart skipped a beat as I realized that she accepted my offer! She was such a slut she had already jumped to the idea of having sex without even leaving the school! I should have just fallen apart there, but I held it together and kept going.
"But the upper floor of the library..." She knew what I was talking about. The library had more bookshelves on the second floor, and nobody went up there. There were no computers, no group tables. Just rows of books. And the librarians didn't watch that floor after school. I should know... it's been a last place resort for jerking off on days when the bathrooms were full and there was a team changing in the lockerroom.
I took her by the hand and led her there. On the outside I managed to look calm and serious, but on the inside, I was going nuts. Was I really just minutes away from losing my virginity? Was I gonna pull my dick out at school so I could put it inside the pussy of the hottest girl I know? Am I just going crazy?
Maybe I was going crazy. When we got behind the last row of books, I immediately stripped completely naked, head to toe. I must have totally forgotten my normal caution, because I only paused to pull the condom out of my pants pocket before tossing all my clothes aside. I just stood there, my 7.6" in length, 6" in girth cock pointing out straight in front of me, harder than it had ever been.
"Oh... big boy! You're bigger than him!" Of course she had never thought that a skinny guy could have a bigger cock than a football jock. Typical!
She breathed in sharply as I walked up to her. She was actually turned on! I unbuttoned her shirt and attempted to take it off, but she resisted. Of course she cared that she could get away quickly if caught, but didn't care whether I could. And of course she didn't treat this like it mattered. I wanted to be naked because I wanted my first time to be as real as possible. But who knows how many times she had been fucked before!
I pushed those thoughts to the side. I was gonna enjoy this as much as possible, and I was gonna pretend to be as experienced as I could. While I unzipped her pants and pulled them down enough to expose her pussy, she unhooked her bra. I started rubbing her pussy with my right hand as I leaned into her chest and started to suck on her left nipple. I had no idea what I was doing really, if you don't count all the porn I've seen, but she sure liked it! She started breathing faster and I actually felt her pussy get wetter. If it were possible, I would have gotten even harder!
I rolled the condom onto my cock before leaning in to kiss her. This was the second time I kissed a girl, but it was way better this time, with my cock just grazing her pussy! She broke the kiss as I started to push it into her. She moaned a little each inch that went in. My pubic hair touched her shaved pussy lips, and I could only say "Wow..."
To our right came an angry whisper, "What the fuck!?!!"
James had caught us. An angry jock was staring down at me, with my dick visibly inside his girlfriend. Now, you'd think that I'd panic. But I had never felt braver and more masculine.
"Sup, dude?" I asked casually, while slowly withdrawing my dick.
He looked even most pissed, but turned to her. "What the fucking jesus christ are you doing with this little bitch??" I wasn't really offended by the little bitch comment because I had pulled my cock all the way out, to rest against her pussy entrance, so he could clearly see that I was bigger than him.
They had an angry whisper fight for another minute while I stood there naked except for a condom. He lost the fight the moment she threatened to skip their sex night that weekend. She told him to go stand guard, and he reluctantly did so.
Wait. If she normally manipulated him with sex... did she think she was manipulating me into giving her free tutoring? What a ridiculous thought! But no time to think that through.
I started to push my dick back in her. I paused for a moment when I was fully inside her again to enjoy her pussy squeezing the entire length of my dick, then I started to thrust. And with every thrust, I got faster. The warm insides of her pussy rubbed against every inch of my cock as I reached the deepest point, then I would pull out so just the head was inside, then slam it back in. I was in heaven the whole time, my dick exploding with some of the greatest preorgasmic pleasure I had ever felt. After just over 5 minutes of pounding her, my orgasm rolled over me. I moaned at full volume as the feeling increased to one of the longest and hardest cums I've ever had. My god, that felt amazing! And I was enjoying losing my virginity the way I always meant to. Even if it had to be standing up!
I looked over at James. Sam and I were sweaty and breathing hard, and James had an obvious hardon that he was trying not to play with. My bravery keeping up, I slipped my cock out of his girlfriend, and walked up to him. I ostentatiously removed the condom in front of him, took his hand and folded the condom into it, and touched him on the nose the way she had touched me earlier. He glared at me, but did nothing.
As I went to get dressed from my clothes on the floor, he dutifully knelt down in front of her to bring her to orgasm. Fifteen minutes later, he was gone, and she joined me at a study table on the lower floor. I held up my end of the bargain, reteaching her the material she needed to know. Honestly, I'm probably not the best tutor she could get here, and it's really good for me that she doesn't know that. Because we both knew that me fucking her was the cost for every session. Maybe it was even good that I was only okay at teaching, because that meant I'd be tutoring her for a very long time. Tutoring her in her bed... in her boyfriend's bed... maybe even at school again!
As she was packing up her books, I got a text message, "yo dude this sux. usualy i get to blow my load b4 i gotta eat her out! wtf shud i do?" I had no idea how James even got my phone number.
I took that to mean that he didn't bring her to orgasm while fucking her either. That was a relief! I didn't want him to be superior to me in any way today. But I held back on taunting him, and just texted back a jokey offer to give him a handjob the next time i saw him. He probably didn't even realize what was in store for him. Of course I was gonna make him watch next time. Make him watch my giant cock stretch her pussy more than he could stretch it. Make him watch my ass flex as I push into her. Make him listen to me moan loudly in orgasmic ecstasy while pumping cum out.
And you know what? One of these days I'm gonna make him film it on his phone. Maybe after I get some more practice fucking. Then someday the boys who have never seen a girl naked in person will borrow his phone and see what's recorded on there. And I'll be fucking the hottest girl in school, rubbing it in the nose of the jock we hate the most, and I'll be a sex god to all the Boys Under the Bleachers.
So yeah, there ya go, my first story ever. If you want to see more, let me know at jacksta@ymail.com.