Tag: High School

That Time in History Class [MF]

Now that I am older I look back on my senior year of high school and realized that I missed out on more than one opportunity if I had only been more confident of myself. Alas, being a teenager (18) in the suburbs leaves you doubting yourself quite a bit, or at least that was my experience.

There was this girl, Sarah, who I had been going to school with since 6th grade. We went to the same church, same sunday school class, similar group of friends but we were never insanely close or anything. We just always happened to be around each other due to our similar activities.

She was nice, opinionated, alternative views type girl. She was pretty, but not like drop dead gorgeous or anything. Her main attributes that men always caught on to were her very large breasts and ass which she had no problem showing off in small torn jean shorts and tank tops. Read more »

My first hookup ever. Cancun pt. 1 [MF]

**Background**

I was 18 at the time and had just graduated high school. Up to that point I had only slept with my high school girlfriend, but we had broken up a few months prior. Just a few days after returning from a Hawaii vacation that I got as a graduation gift, my family took its annual trip to a resort in Cancun this time. I really shouldn’t have spent so much of my graduation money in Hawaii, because in Mexico I was of age and could have had way more fun at the clubs. My family prefers the convenience of filling up our hotel suite’s kitchen at the start of any trip. Knowing I would be stuck at the resort, I made sure to stock up on beer for myself when we were at the store.

**Lead up**

It was my second night in Cancun and I had so far only spent time with my family. I was college aged now, and legal to drink. With college around the corner, I wanted to do what I thought always happened in places like this to people my age: get drunk and hook up. I had always been shy around girls and extremely insecure, which most people wouldn’t expect because I was known for being outgoing and flirty. Knowing I wouldn’t have a problem making friends I filled my backpack with my first legally purchased beers and let my family know not to wait up for me. Read more »

[M]y sexy and intense casual relationship with my [F]ormer high school teacher!

I was 19 years old, I was nearing the end of my first year at college and was preparing to have a relaxing summer. Every day, I would pass my high school on the way home, it was the quickest way to get home. Everyday I remember when I was taught by the most intelligent and beautiful woman, when I was high school, she was my English and Science teacher and she was the closest person I was with friends with in high school. There were no feelings between us back in high school, but when I was in college, the feelings began to develop.

When I would walk pass high school on the way home from college, I would see her leaving and getting ready to go home. One day, we struck up a conversation and caught up with each other, she asked me how college was going and I asked if she was getting worked hard by her new students and she said that our year group was better. At the time, she just turned 32 years old. Read more »

My very sick buddy needed to relieve some tension. I’m just an idea man, folks. [FM]

Note: this story isn’t about me, but I’m directly involved in it, if that makes sense. It’s a sad story, but its also a happy one. You’ll see. I realize in advance that this isn’t a typical /r/gonewildstories post, but it’s one that’s pretty rad in its own way.

Also: trigger warning for cancer, death. I mean, sp*iler alert, but also…yeah.

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In 2015 when [I was the touring DJ for a frat rapper](https://www.reddit.com/r/gonewildstories/comments/i4jdcc/i_got_a_blowjob_from_a_bottle_service_girl_in_the/), it was one of the best times of my life. I got to travel the country and get paid pretty darn well. I was away at one point for two months, and I was texting my buddies from high school and uni pics of the #tourlife.

My best friend (we called each other our hetero-lifemate), Tommy, was as happy as could be for me. I met Riff Raff at one point and I got him to send Tommy a video message (dude was a big fan, in an ironic way). It was fun. After the tour ended, I went back to Manhattan, and Tommy called me. He told me he had stage 4 lung cancer, and he probably had six months to live. This was, needless to say, shocking to hear. He smoked probably 150 butts in his life — turns out he had a bunch of super-rare genetic markers for his ancestry that put that shit in his lungs. Read more »

I [20F] sucked a stranger [25M] in exchange for a beer [MF]

This happened a couple of years ago and was right before I could buy alcohol – just a few months shy. I was at a huge party and had already gotten a few glasses of punch. I was feeling just a bit tipsy but after an hour or two, I was feeling thirsty again. I remember thinking another beer would have been so, so good.

There was only one person with alcohol at the party: a guy, who was slightly older. He was one of the few there old enough to buy beer and had brought a 12-pack, but that mostly for himself and his friends. I didn’t know him at all, all I knew was that he had around six beer left and I wasn’t the only one who was thirsty. The stores were closed at this hour, so even the few people who could buy beer, well, couldn’t.

I didn’t really know how to ask for a beer and didn’t want to be “that” girl, so I just thought I would chat him up until he offered me something to drink. It worked. Flirted with him, smiled at it, showed a lot of interest. Then I subtly moved the topic to how I was still 20 and not old enough to buy beer, but I would in a few months. Read more »

[MF] What Happens In Exam Room 16, Stays In Exam Room 16 – Until Today ;) Part 1

What follows is a story about a tryst I had at work with an older woman. This will likely end up being part 1 of a multi-part story, that is, if anyone finds this interesting.

When I was 21 I started working at a company doing medical billing. My mom has worked at this company for a long, long time and this is how I got the job. I had worked some odd jobs there over the years, but this was my first time being employed full-time. In previous stints at this place, when I was in High School and college, I would be working with other individuals my age. There were two girls during this time that were very attractive. We generally worked in an unoccupied doctors office, or in the basement, and I always fantasized about fooling around in one of the offices with one of these beautiful girls. Unfortunately, that dream never came true.

When I was hired on full-time, I found myself – a 21 year old, fit young man – working in a department of all women. This time, however, there wasn’t an attractive one in the bunch. Given that it was a large employer, there were quite a few attractive doctors, nurses, receptionists, etc. working in the building, and I still fantasized about messing around with someone at work. Read more »

Our Sex Life – Part 1 The Lead-up [FM] [MFM]

Hey there! We are long time lurkers first time posters here. We are a young couple who has been together for about 10 years and we have had some experiences that still drive us crazy to this day. We are writing this series hoping you’ll find our history sexy too;) The stories will be primarily chronological with pictures where available. Our adventures include lust, love, exhibitionism, sex games, cheating, make-up sex, threesomes, and more! We hope you’ll stick with us through this journey and we look forward to hearing your responses! Enough background and on to the good stuff… Read more »

Tales From Boarding School: A True Story. (#1)

When I (21 F) was a junior in high school, I began attending a military boarding school several states away from my home. I was a devious teenager so my parents weren’t sad to see me go, but going to boarding school was mostly my decision. I have always welcomed change. I have always been a small girl. Back then-just like now-I was short, skinny and tan, with small breasts and a large butt. I dyed my hair blue-black and drew skulls and upside-down crosses on myself with sharpies during class. Me and my friends snuck in alcohol and cigarettes at the risk of suspension (or expulsion after first offense).

There was a guy named Cam Hanover at my school. He was nice. We had talked a few times before, and he was one of the teachers’ sons. His hair was cut short like the other boys at the military school. It was dirty-blonde in color, and his skin was pale. I knew he was smart, and not straight-edge. He was a runner, and you could tell by looking at his calves. He wasn’t a boarding student, as he lived with his mother (who had been my teacher the previous year), Ms. Hanover in town. Read more »

Rekindling an old flame (MF) (slow) (masturbation)

Part 1, more to come.

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“I had a dream of you last night.”

    I watched the text cursor blink a few times, then hit send.

    The blue chat bubble popped up on my screen and my stomach did a little flip. I hadn’t talked to Trey in years. We’d circled around each other in high school, making nervous, awkward conversations until we’d exchanged emails and started chatting online. He was a goof, and so was I. We grew used to each other online, and it made us more bold in person. Slowly we became friends. With the buffer of our computers between us we’d started exploring with each other, as young people do, but that was as far as we went. I knew the way he thought about me, but I just wasn’t ready to have a physical relationship, and there was no way he wouldn’t want one from me eventually. So after a while we drifted away from our explorations and our friendship settled back into platonomy. Every so often I caught him looking at me with those eyes, but he wouldn’t push on me what I didn’t want. Read more »

Bicurious best friends (18F & 20F) make out, eat each other out and trib while boyfriend (25M) watches.

It was Tessas first night in the city with her childhood best friend and now roommate, Bella. Bella was wasted and putting on a show for her 25 year old boyfriend, Jordan, who was sitting on the couch and drinking whatever was in his cup. Tessa giggled drunkenly at Bella and took a swig of the bottle of wine. Tessa had never seen Bella like this before, Bella moved to New York City two years ago after she graduated while Tessa finished out her last two years of high school. Now she’s graduated, all moved into their small two bedroom apartment and ready to finally live a different life. They were definitely polar opposites, Bella was the life of the party while Tessa had only been to one party before, her Sophomore year she attended a Senior party with Bella and threw up all over her then crush, Jimmy Henderson. Embarrassing, to say the least and enough to put her off to drinking until now. Sure, she’d had a few drinks here and there and smoked on occasion but she’d always known her limit. She still did.. until one glass of wine to celebrate Tessas move turned into three bottles shared between them. Read more »