High School Archives — Page 628 of 805 — NSFW story

[FM] Going topless and giving head to do better in a class

When I was in college everyone was required to take a bunch of classes outside their majors in order to graduate. One of the requirements was taking a history class. I was never great at history in high school, but I wasn’t too horrible. Unfortunately, I fucked up with registering for class and ended up taking a history class on the medieval era. The professor required that we write basically one paper per week. The first paper I got a D on and I straight up failed the next one. It was too late to drop the class, so I really needed a way to do better in this class.

The class after the second paper was handed back, I looked around the room for anyone that I thought could help me. I saw a boy who I thought his name was Derek. He was in one of my classes from the previous semester, and he seemed pretty smart. I decided I would approach him after class and ask for his help (and if his name was Derek lol). Derek was 5’9”, had short blond curly hair, and had a thin frame. It was winter so he was dressed in a hoodie, jeans, and sneakers. I asked him for help (and confirmed his name) and he seemed happy to help me. We agreed to meet in a couple of days at in his apartment to work on the next paper together. When I got back that paper, I got a B. I was so happy! Derek and I kept working on the papers together, and he was a huge help. My average went from almost failing to a C+, with plenty of time to bring it up. Read more »

That ti[m]e I [f]ucked my high school crush in the ass

(I wrote this up approximately ten years ago, right after the event. Just found it recently. Everything described here took place after we graduated, and thus the participants are over 18–don’t get too excited, ya perv.)

I had a huge crush on Meghan in high school. She haunted me like a ghost, always in my dreams and daydreams, but things never quite got started between us. I never got the timing right, I suppose. She’s incredibly gorgeous, in a way that’s more cute than seductive (most of the time). She’s tiny–I doubt she’s ever weighed more than a hundred pounds in her life–with a moon shaped face, freckles, and lips that are always sticking out slightly in a little pout. Even though she’s small, she’s well built for her size–her tits are big for her frame, about the size of large oranges, and her ass is firm. I always imagined it to be perfectly ripe for a good fucking… Read more »

My [MM] first time with another guy

We talked online forever, it seemed like… I found him on a site and discovered he was a few cities over. I had a girlfriend. We started to chat normally and soon asked each other if we ever had been with guys. He had and was a year older than me, I told him I hadn’t. We talked more and eventually sent each other pictures. He was so handsome!

Soon our talks became more sexualized. He asked me if I ever thought about him while getting off, I shyly said I did and he asked me what I thought about. I told him a few fantasies and he shared that he was turned on and asked me for pictures. I promised that when I could take a few, I would and finally I sent him a few of me in a speedo. He was so complimentary and sent me shirtless pictures in his underwear. Pretty soon it escalated… We were requesting specific pictures from each other and going back and forth. He asked me to shave my hair off and pour oil on myself and send him an oiled pic. I still remember how hot it felt to show him. Read more »

Taking an old [F]riends virginity one su[M]mer

This takes place exactly a decade ago this month. 18 year old me gets a text from Heather. Heather is a childhood best friend that I grew up with and lived around the corner from. We have a lot of history. None of it sexual until now. We just graduated high school and both turned 18 recently. Our conversation goes something along the lines of “hey. I need to ask a favor. A serious favor.” I’m typing from memory, none of this is direct quotes, just a summary.

Me – everything ok?
Heather – yeah, it’s something personal though and I don’t know how to say it.
Me – I can’t help if I don’t know what the deal is.
Heather – ok, fine. I want you to take my virginity.
Me – are you fucking with me?
Heather – I’m still at work, I’ll come by after I get off.

Now at my house…

Heather – you’re one of my oldest friends. You’ve always had my back and been good to me. I trust you and I know who you are. All of my friends have been talking about sex lately and I’m the only one that hasn’t had sex. I think about it all the time and I want to do it. I want it to be you. So? Read more »

Work Trip Distraction [MF]

I was away for a work trip the other day, to a city where I happened to have a lot of friends from the past. It was an overnighter, and I did have a work colleague with me, so I had to play my cards right. Maybe a six hour window that I could have some fun, as we had meetings all the following day. I didn’t particularly want to do the open call out I usually do when I’m in town, and so I messaged two old friends that I knew would be up for it.

One had a cousin’s birthday to get to, and wasn’t sure what time she’d be finished up. A bit of a pity, as she’s the one I spent the most time with on my last trip out, and to say that she was a lot fun would be a grand understatement. The other had other friends in town, but she was quite convinced that she’d be finished dinner early with them, so had time to catch me later for drinks. Read more »

[MF] Co-Workers, Cheating, LA Business Trip…(Part III)

[Part I](https://www.reddit.com/r/gonewildstories/comments/8r31u6/mf_coworkers_cheating_la_business_trip/)

[Part II](https://www.reddit.com/r/gonewildstories/comments/8r5opi/mf_coworkers_cheating_la_business_trippart_ii/)

For those joining for the third part, welcome and feel free to skip ahead! Newcomers – I’ll give you some background.

Ashleigh – She was 23 at the time. New to the company within the past year and very confident. She had been in a relationship with the same man since high school and was happy as well. She had curly brown hair, 5’6, athletic body and just enough sass and personality to make every man’s head turn. She could fit in with any crowd and could talk with anyone. She was a joy to be around. Her name was Ashleigh.

Me – I was 25 at the time. Working for a staffing company in the suburbs of Chicago for the past few years. I had been engaged and soon to be married in a week. I was and still am a 6’1, blonde haired, blue eyed, athletic male. I was happy and enjoyed my life. Young and energetic with a bounce in my step!

As Friday night came to an end I laid down in bed knowing tomorrow would be even better. I had one more night in LA to make sure Ashleigh and I had time alone. Read more »

I was fondled by dozens of old men at a Korean Spa [TM]

*Message From Aly: I’m back by popular demand! Thank you guys so much for like probably hundreds and hundreds of msgs here and on kik asking me to write more. I love you guys :)

So this one takes place shortly after this story: https://www.reddit.com/r/gonewildstories/comments/4jayg6/first_night_at_college_ended_with_two_cocksm_in/

So back when this happened I was totally a virgin about sexual encounters and anything related to men. I had always been sexually repressed after going through so much in high school with transitioning and living in a conservative town. When I finally was able to live the way I always dreamed I’d live, the first few months on my journey were a bit awkward to say the least. I had no idea where to begin to find someone to want to explore with me. Yes, I thought I was good looking enough at 18-19 years old and with my petite body and feminine features thanks to HRT, I really didn’t worry about whether men would want me or not. I was more like afraid of the actual process since I was not pursued at all in high school. In fact, I was bullied like crazy for being a “sissy” or “gay”. Read more »

Becoming My Roommate’s Toy [MM] [BDSM]

This story is the first erotic work I’ve submitted online. Hope you enjoy it! ;)

I awake to a loud sound of glass breaking.

It’s probably my roommate coming home drunk again. Mitch had gone out to a bar with his friends earlier, so I expected he would make his usual loud entry to our apartment at 3AM.

I met Mitch during the summer before my senior year of high school. We were both working as lifeguards at the public pool. We soon became close friends, then got an apartment together after graduating last year. We are both 19 years old, now working as waiters at a local restaurant.

He can be kind of an asshole at times. He calls me gay because I’m a virgin. If only he knew I actually am gay and the only person I want to sleep with is him. I’ve had a crush on him ever since I saw him in those tight swim shorts from across the swimming pool. It’s too bad he’s as straight as a ruler.

I’ve gotten used to hearing a lot of stumbles in the middle of the night as he’d walk to his bedroom after having a few too many drinks. Read more »

An eventful month, part 4 [MF] [long] [series]

Part 4:

If you want to read the previous parts to catch up on the events so far:

[Part 1](https://www.reddit.com/r/gonewildstories/comments/8nm5f0/an_eventful_month_part_1_mf_long_series/?st=JIEVPBCU&sh=42b25dfa)
[Part 2](https://www.reddit.com/r/gonewildstories/comments/8nwbkm/an_eventful_month_part_2_mf_long_series/?st=JIEVQFS3&sh=ee28071d)
[Part 3](https://www.reddit.com/r/gonewildstories/comments/8pnwxp/an_eventful_month_part_3_mf_long_series_cheating/?st=JIEVQYAN&sh=c1ff01e6)

To summarize: Back about 15/16 years ago, I had a very fun and sex filled month. It started with a friends with benefits situation with my supervisor at my night job. After a couple hook ups (Parts 1 & 2) and at the start of the first extended hook up at her place, she finally informs me that she’s married. I fuck her anyway. (Part 3)

A few days later, I get a call from a high school friend of mine. I’ve graduated but she’ll still finishing up her undergrad degree. She’s home for the holidays and wants to know if I’d like to meet and catch up, etc. I say yes and we set up to meet the next night. Read more »