Tag: High School

That time I won a prize [MF]

I’ve had a few fairly long term relationships, most with a generally decent sexual component. Just after the break-up with a long term post high school gf (and after an almost unbroken 7 month dry spell that had been preceded by almost daily sexual activity) I was approached by someone in a college class I had. Melissa, physically, was the polar opposite of my ex, with D-cup breasts and a decent ass. She was a little chubby, but that didn’t bother me, as, when in college, I wasn’t the most outgoing person, and the combination of the dry spell and the fact that she approached me led to a frankly not great in any way relationship.

Anyway, the sex was…fairly vanilla, as I was (and presumably still am) more experimental than her and willing to try new things, both in and out of bed. The “kinkiest” thing she would do is ask me to rent some porn from the local video store for us to watch together (damn I’m old). And she would get invested in the story. Read more »

The ti[M]e I fucked 3 girls in 1 day and 2 were strangers

How I [M33] fucked 3 different girls in one long day, 2 that were strangers

Sorry if this is a long one, but the details matter.

I start my day waking up with my normal fuck buddy at the time. She was a tiny Latina girl with perfect tits and a tight fit body. She was in college and a party girl who would be out late, come over drunk in the middle of the night and we would usually wait until the morning to fuck as I would be asleep. I woke up, reached over and found her panty-less with a sports bra on next to me. I’m instantly hard, start rubbing her pussy from the back and she’s drenched a moment later. I lift her tiny cheek and slide right in and begin railing her from the back hard. She was kind of a weird moaner, low and deep but also loud at the same time. We go at it for 5 or so minutes and I unleash my load deep in her. She whimpers a bit and passes right back out. I jump out of bed and get on with my day. Read more »

[FM] The Time I Fucked My High School English Teacher At A Swingers Party

Hey everyone. I was told this might be a good place to tell my story. Probably don’t need to, but I’m using fake names to help protect identities. Sorry if this gets kind of long. There’s a lot to unpack!

I graduated high school about 15 years ago. While I was in school I had a teacher, Mrs Simmons, several times for a couple of different English classes including my AP English course. Over the years we became pretty familiar with each other. I had always thought she was a pretty woman. Early thirties, blonde hair, and what I suspected was a pretty nice body, but she always wore conservative and sort of baggy clothes that never showed it off. We never got too personal with each other, but I always figured she was a pretty straight laced person.

After I graduated high school I moved out of town, and met a wonderful woman who I later made my wife. After a couple of years things in the bedroom started getting a bit stale, and we decided to really spice things up and attend a local swingers party to check it out. We didn’t hook up with anybody that night, but fell in love with the lifestyle, and how close all of the couples there were. We ended up diving in head first, and before too long we were doing full swaps and having an absolute blast. Read more »

Classroom Fuck-Circus [Mind-Control][Anal Toys][Free Use][Orgy][Humiliation]

In my senior year of high school, I stupidly enrolled in a “Writing the Essay” college prep course. The class was comprised of four guys, counting myself, and six girls, all of us seniors. Our teacher, Mrs. Floyd, droned on wearing a stupid grin about what to expect our freshman year and how important these skills would be. I paid a third of attention, my focus divided between ogling at my female classmates and tinkering at a certain device under my desk.

My step-father worked at the NSA, and always kept his work squirreled away upstairs. By happenstance, I went to look for a pen in his office and stumbled across documents pertaining to radical sound research. I took a picture of the papers on my phone and disappeared into my room. The analytics described a device that could subliminally message a massive group of people. Using my relatively strong computer skills, I devised a smaller device that would work on a select group of people, say ten, but with greater effects. Read more »

The Pregnant Woman on the Ferris Wheel [M/F] [Public] [Oral]

It was a sweltering day in the middle of July, and FunWorld was packed. I was accompanying my girlfriend Lisa and her parents, who annually met extended family here for reunions. Lisa and I had been together for a little over three years. These familial gatherings were a fairly exhausting exercise, putting on a nice face and talking about my job or whatever other trivial tidbit to 20 different 2nd tier cousins. Standard obligatory boyfriend stuff, but I was still relieved when Lisa and I could break off and do our own thing.

The sun was hanging sexily low in the sky, bathing the amusement park in that magic, yellow-orange, late afternoon summer light. It made Lisa’s platinum blonde bob glisten. We got a funnel cake and sat near a directory sign that laid out the major landmarks of the park.

“What do you feeling like riding?” I asked her.

“Ooooh The Devil’s Dirge!” she excitedly suggested.

This coaster was the park’s newest attraction: one of those towering, loop-filled, highest-allowable-speed-and-height kind of monstrosities.

“Yeeesssss! Think the line is still super long?” We’d considered riding earlier, but the wait was around 3 hours. Read more »

[MF] I (M36) Went from teaching her (F23) English, to teaching her sex (Part 2)

A couple of months passed since my last “lesson” with Hina. I thought about her from time to time, but she was dating some other guy, not to mention our age gap and the fact that I used to be her teacher back when she was still a young teen. I decided I was lucky to have gotten her to blow me twice and swallow my load once, and move on keeping the hot memory. One day Hina messaged me out of the blue and we texted for a bit, which lead to a meetup. While there I asked about her and her new boyfriend and if our lessons were any help.

“Yeah, everything went okay I guess.” She said not sounding all that excited.

“Just okay?”

“We made out, got naked, I gave him a blowjob and I think he liked it. Then we had sex. It was a little painful and uncomfortable at first but I got used to it, and it wasn’t bad.”

“You still don’t sound that jazzed about the whole thing.”

“Yeah, I guess I was just expecting more. SEX! Everyone’s so crazy about it. But he put it in, in and out for a few minutes, and then he was done.” Read more »

The girl who started flashing me on her graduation photo shoot… [Mf] [public exhibition] [oral] [fuckin’]

*I got a PM from a throwaway account containing a real sexy story and a request for me to re-write it and post it here. So, these details I made up. But the core of the story is (supposedly) non-fiction.*

I am sitting on a park bench taking in the scene — a fountain across from me, a field of grass beyond, shady trees and a creek past that — when coming around a neighboring shop, I see Tina walking toward me, proud, tall, and blonde. A tall, nervous looking girl trails behind her with hunched shoulders and jittery movements.

I sigh, then pick up the bag of cameras from the bench beside me and go to meet them, forcing a smile to my face.

Tina immediately starts in, “It’s Emma’s fault we’re late,” gesturing at her daughter, “What do you have to say for yourself, Emma?”

Emma’s gaze is fixed on the ground. “Sorry,” she mumbles.

Late for an outdoor portrait session isn’t great, the golden sunlight of late afternoon lasts only as long as it does. But there’s nothing I can do about that, and it is looking anyway like calming Emma’s nerves will be the bigger challenge. Read more »

[MF] I (M36) Went from teaching her (F23) English, to teaching her sex (Part 1)

Warning, lots of backstory. Skip to **–>** for the sex.

I’m a tall black guy, currently living in Japan. It’s not what I do now, but I originally came here as an English teacher. I worked in a high school in a Tokyo suburb. Some of the student girls developed silly crushes on me, some were obvious, some I didn’t realize until the end of the school term, when they either told me in a letter, or their friends ratted her out. I never liked young girls, and working with them I could see that they were basically still just kids, and of course it would have been a horrible ethics violations, so nothing ever went any further than that.

There was one girl, Hina, who I enjoyed talking with after school and between classes. I never got the vibe that she had a crush on me, but she was cool to talk to. She was down to earth and had a dry sense of humor. She wasn’t the cutesy giggly type at all, kinda a run of the mill, average girl, but not in a bad way. Read more »

Medical Mother [MF] [Friend’s Mom] [Oral]

After several weeks of studying and wrapping high school up graduation came and passed. The summer to follow was more quiet then ever because all of my friends were on trips out of town. Everyone came up with their own way to celebrate and I had mine, which was just sitting at home and playing video games.

One of my closest friends, Bryan, was in town and had some drinks to hangout for a night. I took him up on his offer almost immediately and drove to his house in less than hour at noon.

I was about 6ft tall, Bryan being 5’8. We weren’t football players or in any specific cliques but we were relatively popular in high school. Bryan was in a relationship and I broke up with my girlfriend right after our senior prom. Bryan and I had known each other since elementary school and we stuck together because we knew we’d be trapped in this town for all eternity.

Bryan lived with his mother and older sister Hannah. Hannah, like seemingly half of the town was also on vacation with her friends. She was pretty hot and I was never shy of admitting this to Bryan. I could probably never swing with her, however, as she was in a three year relationship. Read more »

My Secret pt II [F] [m] [non-fiction] [Adultery]

I have recieved many questions about my post ,’My Secret” and what happened and if I seen Carlos again. I will share but once again I am not a writer so be kind :)

It was awkward at first when I went back to work and I tried to think of many reasons not to go back and face Carlos and the fear that he would talk or it would leak out what happened that night but to my surprise he never spoke a word about it and never tried to push me on it. It was about 10 days after it had happened that Carlos got fired from work, he went out his own way I guess you could say as he was caught having sex in the stairwell of the building with one of the girls who worked in HR. I always thought he got shafted though as he was fired but she was just reassigned to another office and kept her job. Anyway, so I have made several chat friends on another site and some i make it a point to talk to when ever I can and others we just chat as time permits but I have found them to be exciting, fun and sometimes hot, sexy and erotic. It is a way for me to express myself without fear of ridicule. Read more »