This will be a long one. For background, high school was not my favorite period of time. I moved a lot as a kid and by the time my family settled down I was better at reading books and writing stories than I was at normal human social interaction. I went on zero dates in high school, never got kissed, and as far as I was aware I was an undesirable nerdy kid that nobody found attractive.
Once I did finally start dating I blossomed and grew in a lot of different ways which is why I have so many wild sex stories to share. Sex is my one true vice and once I figured that out I started to learn (and un-learn) all the things I needed to, to be a great lover. It didn’t hurt that I am 6’2”, can get in shape pretty easily, have a decently big cock, and years of reading good books which taught me the importance of language and how to spit game when I need to.
I skipped the five-year HS Reunion, but by the time the ten year rolled around I thought ‘Fuck it, why not?’ and got a ticket to go solo. I knew a few of my friends were going too and thought it might be fun to experience the train wreck of it all firsthand. The organizers did a good job and set us up at a nice country club. I showed up on time because… well, I’m still a nerd at heart and I like being on time to things. There were four or five people there when I arrived and my initial interactions set the tone for how stupid that night was going to be.
It started off with some awkward ‘Who are you again?’ conversations, some people talking about their kids, and then a super awkward girl who had become white trash walked up and started complaining about how she was picked on years ago and wanted apologies from some of the ‘mean girls’ that made her life hell. I was not going to be party to any of that, so I turned to two of those ‘mean girls’ who were there and asked “Anyone want a drink?” It was a unanimous ‘yes’ and we started drinking early. The pace did not let up.
More and more people trickled in over the next hour or so. A few friendly faces, a few not. About half of my best high school friends showed up including my old pal, Pete, and my old friend with benefits, Penny. Interestingly, Penny and I had, had several threesomes with Pete’s ex after they broke up — Pete did not know that yet. Pete and I had been hanging out once in a while after I stopped sleeping with his ex so it was good to connect with him as we tried to carve our our own fun at this awkward gathering.
Skipping many of the more doldrum aspects of the evening there are three major events I need to outline as setup for the remainder of this story. The first involved me getting incredibly bored and wanting to liven things up. Again, my actions often belie my nature and I got shit going on the dance floor. Yes, awkward in high school. Only went to my Senior Prom (and barely). I was the quiet kid that no one paid attention to. Now, here I was, talking to the DJ and getting them to throw on some good tunes, then heading to the dance floor solo and starting things up. Here is the thing — as I mentioned before — when I realized I wanted to have a lot of sex I started to strategize what I needed to be good at attracting a partner. Dancing was one of those things and — if I’m being honest — it is the one that has paid the most dividends.
In only a few minutes many of the girls who had been popular in high school wandered over to join me and that opened up floor for everyone else to dive in; fueled by liquid courage. The guys who had been popular in high school came up to me to buy me beer and ask me who I was — they didn’t remember me but were so impressed that I got literally all the hottest girls from the old days to dance with me that they wanted to be my friend suddenly. My buddy Pete joined in right away and helped escalate things even more. In the next fifteen minutes we had a good ole’ party on our hands and it wasn’t awkward anymore.
The next big event worth mentioning was when a dead girl walked in with her boyfriend. I saw her face, took a moment to process things, and started to think I must be crazy. I walked up to her — admittedly I was a little inebriated — and introduced myself.
“Hey, I’m glad you are here. I had heard that you died!” She was a girl I had had a crush on once for three days in the 9th grade. The years had been kind to her, she was beautiful, had blonde hair, big blue eyes, a nice figure, and a huge rack.
“Oh my god. What?” I had obviously caught her off guard with my abrupt conversation starter. “Wait. Who do you think I am?”
She raised a good question. I was pretty sure I knew her name. “You’re Kelly Price, right?”
“No, I’m Jane Price.” She corrected me and I had would have given myself the old Picard facepalm if she hadn’t reacted with the following, “Oh my… oh my god. Kelly Price is dead?”
I grimaced. “Yeah, apparently, I heard about it a few years ago. I guess I switched your name up with hers in my mind. Sorry.” They had been seatmates from elementary school through high school and it was a shock for her to hear about it so randomly. That said we suddenly had a lot to talk about and jumped into a really wild conversation. The gist of which was that, after she asked me if I was there with anyone, I explained that I was more of a casual sex loving, threeway indulging, non-monogamous type; she told me that she was too. When she saw Pete walk by — who had been infamous and very well known in high school — she wanted to say ‘hi’ but he blew her off. Well, until I called out to him.
“Hey, Pete, hold up.” He stopped and swung around on his way to the bar. “Do you remember Jane Price? Well she’s into the same shit I’m into if you know what I mean.”
“Ohhhh yeahhhh?” Pete walked up and suddenly poured on the charm giving her all his attention and pervy focus. I walked away to get myself a drink and get back to the dance floor and that was that for a while.
The last major event of the reunion itself that made any big difference was last call. It was 10 pm and things were shutting down. The people who were down to party started to get a little disappointed and I offered a solution to the group. There was a dive bar nearby whose reputation was synonymous with trouble and I started the effort to rally the troupes and get everyone to head there. It worked, I was the life of the party that night, I had the Midas touch and I could do no wrong. Damn near half of the people at the reunion made their way to the bar and we made that places night. The drinking continued, the dancing continued, the shenanigans continued.
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What happened next is where the good stuff starts. Everyone was having a good time, especially my buddy Pete. The girl, Jane, who I had been talking to — who was there with her boyfriend, a slightly older guy I’ll call Tom. Well, Jane was getting Pete’s full force attention on the dance floor. He was dancing on her — hard — grinding with her, grabbing her ass, kissing her neck. I was pretty sure he was not aware of the boyfriend and I was pretty sure the boyfriend could whoop Pete’s ass. Pete was a charming and good looking guy. Olive skin, dark hair, great smile. However, he was short (maybe 5’6” or 5’7”) and slim and his ‘Napoleonic complex’ had gotten him his ass kicked on several occasions.
I spotted Tom standing at the bar drinking whiskey and Coke and decided that I needed to protect lil’ Pete. So I started to dance up on Jane in such a way that he wouldn’t be able to see her or Pete doing their thing. My old FWB, Penny, was there dancing with some other guys and we made eye contact. She had seen Pete kissing on the girl and saw me swoop in. Penny looked at me with a ‘What the fuck are you guys doing?’ look that I knew all too well. I shrugged with a ‘The same crazy shit I always do’ look which she immediately understood.
Pete was continuing to escalate things with Jane and Jane was really enjoying it. I decided that I would try to mitigate any future disaster by buying a few drinks. I got Jane and Pete’s requests, then went over to Tom and asked him what he was having. He declined the offer, but I insisted and bought him a beer. While I waited for everything to get made, presented, and paid for I watched Tom closely to see if he was paying attention to Pete and his girl. He was. He didn’t seem to care. I started to piece things together and wanted to confirm.
“Hey, Tom. Here’s your beer.” I passed it to him casually as I nodded my head toward where Jane and Pete were grinding. “Question for you. Are you guys swingers?”
“You could say that.” He nodded in the affirmative as cool as a cucumber.
“Cool. Very cool.” I got the rest of the drinks and made my way back to Pete and Jane. Beverages distributed I offered my next errant thought freely to the universe and leaned in close to make sure both Jane and Pete could hear me. “Hey, just so you know, Pete and I will fuck the shit out of you while your boyfriend watches if you want.”
She started to grind her ass into my crotch more as she raised one hand up and gave me the ‘OK’ sign. Then she turned around and kissed me hard. When she was done she turned and kissed Pete the same way. Penny saw and shot me another glance — probably a little bit jealousy, a little bit concern, and a little bit confusion.
“I have no idea.” I mouthed back to Penny as Pete and I continued to dance up on Jane. That wasn’t true though; I knew what I was doing.
The four of us — Pete, Tom, Jane, and me — ended up standing outside the bar for a few minutes to discuss the plan in a place where we could actually hear one another. They invited us over to their apartment which was about thirty minutes drive from there and that sounded good to us. Pete lived about two hours away and I lived forty minutes away and had two roommates who probably wouldn’t appreciate hosting us all for what we were about to do next.
We took three vehicles back to their place — yes, I am fully aware that we should not have been drinking and driving — this is not a story of the laudable decisions I made that night. We had a little time to sober up as we drove and, to my reasoning, everyone the chance to decide if this was something they actually wanted to do or not. I parked next to Pete and asked if he was good; not only was he good, he was fucking excited. We walked up the house, walked in, and had a perfectly normal awkward conversation for a few minutes while we got a tour of the kitchen and were offered some drinks. Jane and Tom had changed out of their formal wear and into something more comfortable.
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The initial thrill of the prospect of what we were about to do seemed to be wearing off. No crowd, no music, no urgency of the situation left things wanting. Well, I came to fuck, so my bold approach and Midas touch needed to shine again. I looked around the room one last time to gauge interest, then I made my move.
I walked right up to Jane, grabbed her shirt, and pulled it up over her head exposing her massive breasts — the biggest I have ever seen in person. I leaned over right away and took one of her nipples into my mouth as I sensed Pete walk up and start to make out with her. I looked over my shoulder and Tom was just standing in the kitchen watching — still perfectly cool with everything going on — so I took another bold step and pulled off Jane’s shorts leaving her fully nude. I dropped to my knees pushed my face into her snatch and started to lap away at her pussy.
Pete tore off his shirt and pants and kicked them aside. I started to do the same, but with more patience and precision as I was intent on eating Jane’s pussy. When Pete was left in only his underwear he returned to Jane and started to play with her nipples. I could feel her legs starting to give out and suggested we move into the living room and told her to lay down.
We migrated a few feet, I stripped down to just my boxer briefs and A-shirt and returned to the action on the floor. I spread Jane’s legs wide and thrust my tongue as deep into her vagina as I could and started to tongue fuck her. I wrapped one arm around her thigh so I could reach her clit from above and began to strum at it as I shoved my rigid pink tongue into her juicy wet pussy. I looked up at Jane’s face to see if she was enjoying herself and I saw that Pete had his cock in her mouth. For a little guy I was surprised how hung he was. Not quite as big as me, but way more impressive than I thought.
I looked around for Tom again — I always get slightly paranoid when I join a couple for the first time — and he was nowhere to be seen. ‘Whatever’ I thought, ‘I’m having fun.’ It looked like Jane knew what she was doing and I wanted to put my cock in her mouth too. I leaned back, peeled off my shirt, and then pulled off what was left and tucked it to the side like a little care package for myself at the end of this thing. I walked on my knees up to the other side of her face and presented myself. She turned to look at me, smiled, and then slurped my semi into her mouth as I started to fondle and squeeze her breast. I got rock hard as she expertly swirled her tongue over the head of my cock and I let out a groan.
Pete was stroking his cock as he slipped two fingers into Jane and started to spout some serious dirty talk that caught me off guard. “That’s right, suck his fucking cock you slut.” I never said degrading things to my partners so that caught my attention and I looked him in the face. He was staring at her sucking me off as he rapid fire finger blasted her. “You dirty fucking whore. Suck it. Suck that fucking cock you slut.” He sidled back up to her and grabbed her head, moving it back to his hard on. “Suck my fucking cock. Do it. Fucking do it you whore.”
I wanted to fuck her, so I got down between her legs, spit, and then slipped my fat cock into her with ease. Her pussy was incredibly wet and I was wildly turned on. She started to moan and pant as I fucked her and Pete didn’t let up on his verbal abuse. I looked around again for Tom and saw him by the edge of the living room near the stairs with a handheld camcorder. He had apparently run off to grab the camera so he could film us fucking his girl. I was suddenly struck with an emotion that was equal parts panic and joy. I did not want someone else to control an amateur porno staring me and risk it getting out one day — but I also loved the idea of filming a good fuck.
“Whoa!” I called out, “How long have you been filming?”
Pete looked over and saw the setup, he didn’t give a fuck. He just wanted Jane to make him cum. He used the opportunity where I stopped to move the action over to the couch nearby. Jane followed him on her hands and knees and returned to sucking his cock from a much better angle. Pete grabbed a hold of her hair and began to slam her head down, face fucking her hard. He continued to spout his derogatory dirty talk and she seemed to love it.
Tom walked up closer to get a better shot and I gestured for him to give me the camera. He shook his head ‘no’ and I shook my head ‘yes’ and put out my hand. Begrudgingly he passed it over and I gestured for him to join in the fun with Jane and Pete as I started to pass out direction.
“Get in behind her, Tom. I want to see you fuck her. Pete, pull her hair out of the way. Yeah, good. Now go slowly. I want to see her take every fucking inch. Jane, look at the camera. Look. At. The. Camera. Goooooood girl.”
Tom stripped down and started to fuck Jane doggy style from behind. His cock wasn’t long, but it was very thick and had a sharp curve to it. He started to pump into Jane like she was a dog in heat and she came almost immediately. He clearly knew how she liked to be fucked and was hitting all the right spots.
“Fuuuuck yes!” I muttered under my breath as Jane screamed her orgasms out into the universe. Pete got up and I handed him the camera, then I took his former spot on the couch and watched as Jane started to suck on my cock again. My dirty talk was more kind, but she responded to it enthusiastically. “What a good fucking girl you are. Taking three big fat cocks at once. We’re going to fill up all your holes. Fill you with cum. Would you like that? Do you want to be covered in all our thick cum?”
She was moaning ‘yes’ with my cock in her mouth and it sounded great. Tom decided he wanted Jane in a different position and flipped her onto her back and began to pound the absolutely living shit out of her pussy. Her huge tits were swinging everywhere and Pete and I just stood back and watched; wholly mesmerized. I took the camera back from Pete and he made his way back into the fray, taking one of her huge tits in his hand and placing his other hand around her throat and choking her lightly.
“Your turn.” Tom said to Pete who smiled, nodded, and then took Tom’s place. Pete smashed his cock into Jane like a warrior going into battle and Tom and I simply stood back, stroking our cocks, and watched the whole thing.
“How do you like that cock you dirty whore?” Pete was non-stop. “Fucking three guys at once. What a slut. What a dirty fucking whore-slut. Come here!” He was looking at me and gesturing for me to come back in. “Fuck her whore mouth.” I did. Tom joined in a moment later and Jane had one cock on either side of her face while Pete pounded her pussy like a jackhammer.
Jane was incredible, alternating between my cock and Tom’s. Slipping the head of each of our cocks into her mouth, doing her best to get all the way down our shafts. She started to lick and suck both at the same time and I ‘crossed swords’ with a man for the first time. I think some part of me had always been worried ‘that would be gay’ but in the moment I realized that didn’t matter at all.
“I want to ride you.” Jane told Tom in between alternating cock exchanges. “I want you to fuck me.”
Tom got on his back immediately and Jane pulled away from Pete. She jumped up and then slowly squat down on Tom’s stubby-thick cock. For an older guy he certainly had a lot of energy. He immediately began to thrust into her as she sat back, grabbed her own tits, and rode him expertly. She came almost right away, then she came again. It was incredibly hot to watch and I wanted to fuck her again myself; I wanted to make her cum.
I handed Pete the camera and got in position between both Tom and Jane’s legs as though I were going to take her from behind. I decided it would be hot to fuck her asshole while Tom was in her Pussy. That way Pete could put his cock in her mouth and we could truly fill all her holes. I spit on her asshole and started to rub it with my thumb to prep her for pushing inside, but she panicked a bit and asked what I was doing.
“I’m going to fuck your ass.”
“No, no, no. Just fuck my pussy.”
“Okay.” I looked down and saw that Tom was still inside her, but… ‘fuck it, if that is what she wants’ I thought to myself and then pushed into her vagina with him. Again, Tom and I crossed swords and we were double stuffing Jane. She let out the biggest gasp and then Tom and I fucked her like that for a minute, maybe two. She was losing her mind in both pleasure and pain being fully stretch and filled more than she had in her entire life. Suddenly she started to cry and I pulled out to make sure she was okay.
“Oh my god, that was amazing, but it hurts so bad.” Jane lay on the floor crying for a minute as Pete, Tom and I stood back, got her some water, and tended to her needs for a bit. By the time she recovered the feeling of awkwardness returned and Pete and I decided we needed to get the fuck out of there. It was probably 3 am and our day had gotten incredibly weird. He and I got dressed and they invited us to come back any time we wanted. She added the both of us on Facebook to make sure we wouldn’t lose touch and then Pete and I got the fuck out of there and had a good laugh outside by his truck before we parted ways.
“What a crazy fucking night.” Pete said to me.
“Yeahhhhh…”
“I can’t believe you set that up.”
“Yeahhhhh…”
“You’re a wild man.” Pete smiled as he shook his head in disbelief.
“Yeah, life is more fun this way.” I acknowledged before we parted ways. There is a lot more to this story were I to tell fully, but this is the logical place to stop. Suffice to say, the next 48-hours got even crazier.
Source: reddit.com/r/gonewildstories/comments/nap61l/our_10year_hs_reunion_turned_into_a_gangbang
Awesome story and so much detail! Thanks for sharing!
Gotta write about the next 48 hours!