High School Archives — Page 794 of 805 — NSFW story

[m/f] Had sex with my best friends VERY hot mom.

So this is my throwaway account since my friends know my main one. Im 21 and have been friends with Ryan since early high school. All through high school everyone always joked about how hot Ryan's mom was. She was in her early 40s, about 5'6, and in great shape. (she was a runner) All 4 years of high school I was best friends with Ryan and spent almost every week at his house. His mom was always extremely nice and friendly, but never gave off any vibe that she would do anything wrong (they were a church going family). We were close enough where we would talk anytime we were together, but it was never anything inappropriate.

Fast Forward to 3 years after high school. In those 3 years I was going to college 2 hours away, so I only saw her maybe 10 times in that time span and they were all very brief hellos. Ryan and I were still really good friends and we planned to meet up and go on a trip over spring break. Me and 2 other friends went to pick him up at his parents house. We got there, and while he was loading up I had a brief catch up with his mom. Again, nothing unusual. Just the expected, "oh, we've missed seeing you around, etc. etc.". So we pack up and head out to camp for a few days. Read more »

My very own MILF (M/F) (long)

I enjoyed writing about my 1st m/m experience yesterday, but here's something more recent with a MILF that is definitely one of the sexiest life experiences I've had the joy of taking part in.

This story took place late last June. I work in a pretty typical office, a 9-5 job, but on this particular Friday evening last June I was working a bit late. We had a fairly large project that needed to be wrapped up, and it was almost 7pm by the time my workday ended. My friend Tom also works there, and after we finished up for the day we decided to head down the street to our regular pub to wind down.

The pub isn't anything fancy, but is where those that enjoy a pint or 2 in my office go to get their fill. It has barstools, tables along the wall, and a fair sized open floor that is either filled with tables or cleared as a dance floor. There are also some dart boards along one wall, and a back patio. On a typical Friday evening it would be half full, mostly filled with locals that live or work nearby. On this particular night, though, it was packed and the place was hopping! Tom and I arrived around 7pm expecting it to be a typical evening, but it turned out to be anything but. Read more »

Cock blocked by a cop, followed by [m]y [f]irst time receiving a great blow job and some other fun stuff

When I was a junior in high school I was seeing this girl named Miranda. Miranda was a "scene kid," each week her hair was a different color, she had three piercings in on ear, and she was always either wearing the t-shirt for some band or some obscure 90s cartoon character. She had gorgeous dark blue eyes which usually popped thanks to the bizarre colors of her hair, stood about 5'7 with long legs and wide hips. She was also just always fun to be around, had a fantastic sense of humor and a way of making others around her feel comfortable.

We were making out in my car when she groped me over the fabric of my jeans. "Someone's eager," she laughed, leaning in to whisper in my ear "want some head, Gulp?" Gulp, short for "Big Gulp," was her nickname for me, because I worked part time at the 7/11 nearby. Among other reasons, I guess. I apologetically explained that I wasn't the world's biggest fan of blowjobs, I'd actually never come from one. Read more »

If he knew what I [F]antasize about at night [Str8] [MF] [oral]

I’ll give her credit for a gutsy, last-resort move. She has been trying to get with him for months, and every time he gently refuses her. There are only four women at this get-together, so she had a decent shot of getting picked. Too bad for her, that bottle stopped spinning while pointed at me instead. I put on a good show of being the hesitant good-sport, just like I did when she suggested the amateurish game.

“Come on! It will be fun. Just like in high school.” She had said. He had to have known what she was attempting, but he did have a good shot at getting one of the other three. Being a few drinks in didn’t hurt either. So he agreed, and let her blindfold him and leave him waiting in his bedroom.

What she didn’t know was that, like her, I want him. I hadn’t let a single hint show to him, though. I like a bold move, and was waiting for the right moment. She had unknowingly given me just that. But unlike her, I had gotten his signals clearly, and knew he wouldn’t refuse me. Read more »

[MF] How I met Alice. (First fucks and Anal)

Hey guys, it looks you appreciated my story . I decided to tell you how I met and the first time having sex with Alice.

First time I met Alice I was 18 and she was 19, we were in Engineering School, fresh out of high school. In France many colleges and schools have what we call a 'BDE' which is an organisation of students who creates events (parties, trips, whatever where you can drink and party). During the first days of college you have the 'Integration', the goal of that period is to get to know each other and is also a good excuse to drink too much.

So we were leaving the city for a weekend to go camping in a small camp in the wood. Older students prepared games, we were in teams and after putting up our tents we did the games. My team was composed of two guys I already knew and two girls, first one was Alice and the other was a pretty girl, very nice but not single. I immediatly hit off with Alice. We spent a great part of the weekend together, talking. She told me about her ex, always using the word "she". I assumed she was a lesbian. Read more »

Just a Rando(M) High School (F)ling

This story happened while I was in High School and for the sake of the rules we’ll say I was 18 at the time. Given that quite a bit of time has passed the dialog has been mostly improvised from memory but the meat of the story is exactly how it happened.

So there we are in the dead of night driving through the type of place where they play banjo music, refer to black folks as ‘Boy’ still and generally just don’t like their daughters dating people with as much pigment in their skin as I do. Why you might ask? Because I had met another girl off the internet who was very much interested in fucking, but even I was hesitant about going to a place like this by myself.

“Dude, sure you want to do this” My cousin Jay said looking at the house/large trailer that we pulled up too. “You know they probably still lynch your kind around here, right? He said half joking. Read more »

I’m really into this girl I met a few weeks ago. Recently, she surprised me with an incredible blowjob [M/F]

Jump to "While talking about my job" (it's bolded) to get to the actual gw story.

This actually started out as a relationship story elsewhere, then I got a bit carried away. Anyway, I'll leave these details in as I feel the back story provides a little more immersion.

So I recently got out of a four year relationship. It was with a girl I can say I was truly in love with, but was very oblivious to how much of our relationship's shortcomings that we ignored. She was very quiet around my friends, never wanted to try new things, didn't really have a cheery attitude as much as I wanted her to (and needed to be surrounded by). But she was a cool girl, pretty, sweet, and we made a lot of memories together. Time just went on and neither of us were aware that it was actually pretty boring and we were just sticking it out.

We eventually split up because as we became more mature we finally did discover we weren't right for each other. Read more »

Pool Party as a teen (M+F)

I was a fairly outgoing guy in high school, so I always made friends easily, but I was also really geeky and kind of insecure, so girls were rarely interested in me that way.

That all changed the summer after 9th grade. I am rather… generously proportioned, and the girl I had been dating at the time gossiped a lot about my "gift." We didn't date long, but the rumors spread like wildfire in my small Midwestern town.

at the time this story took place, I was used to girls being a bit odd around me because of the rumors. But this is the first time anyone has ever outright hit on me because they heard I was big.

Her name was Lisa. She was a year older than me, a bit of a good girl but I knew from a year of band that she had a wild side. She was a short "blue bone," and that day the sun glistened off her dark skin beautifully. Lisa was blessed by nature as well, and even in her modest one piece bathing suit there was no hiding that she was stacked. Read more »