Taking the virginity of our High School’s outcast [mf] [bullying, humiliation, rescue, hurt/comfort]

I was no snob in school. Despite being beautiful, meaning I had some lucky genes, I still hung out with a rag-tag group of retards. Just nerdy, strange, people. People who didn’t exactly fit it. Mostly because a lot of them were androgynous or gay/trans, also because they played games, watched anime, the typical considered geeky stuff. So I wasn’t by any means the top of the social food chain. Though even my friends considered me out of place among them. Having come from an extremely wealthy family I dressed well, was white, female, straight teeth, great vision, couldn’t gain an ounce of fat even when I tried. Like I said not stunning but rather lucky genetically. Enough to feel like an outsider in my insecure group of dorks. Also weird enough mentally and emotionally to feel like an outsider among the preppy rich kids.

No where was right for me. Trying to fit in I held a lot of thoughts and emotions back. About life, depression, sadness, I was very angst ridden for a while.

Sweet home Chicago [MF]

He is someone I have a lot of history with, goes back to high school now in our mid twenties. He says I’m the love of his life and I know he’s mine but I won’t tell him because I am not ready. Our chemistry is amazing. I recently moved back home, Chicago. He is black, I am Hispanic and we are both good looking people ( my humble opinion and strangers lol). The other day we had date night and it was one of the most passionate nights of my life

We started the night by going to a comedy show. We drove down lakeshore which is a street next to Lake Michigan and you get a gorgeous view of the city skyline as you ride In front of it. I wore a dress, I’m small but curvy and he couldn’t keep his eyes off me. He held my hand while he drove and “accidentally ” brushed his hand between my legs raising my dress. I told him to stop and he told me ” you knew what you were doing when you put that on” he asked me if that turned me on and I lied and said no. After a really fun time at the show we went to a very nice place downtown Chicago where there is bowling, pool tables, arcade etc.

[MF] ASIAN FEVER

So background info on myself, 5’11, Built like a tank and ready to run through walls, Pakistani descent and rocking the average 5′ cock.

So this happened at the end of high school and just before heading to university, both of us obviously 18. The girl in question was Lucy, 5’1, Curvy with big tits for her frame and the cutest nose I’ve ever laid eyes on lol, not the best ass I’ve seen however it would do. She was of Chinese descent. So this made it almost taboo and extra exciting for both.

We had both been talking to each other for a while, as friends while also sending the odd dirty texts to each other. We had talked about sex on multiple occasions and how we would do it. Discussing going down on each other, positions and other people we would want to fuck.

Term was coming to an end and with us heading to different universities, we most likely wouldn’t see each other again. So we arranged for a meet up at hers while her parents were away. Her mum had sorted her out with birth control pills, so she wanted to go raw.

My sisters roommate (part 1) [mf]

So in my last story I talked about how I had hooked up with my little sisters roommate which caused them to get into a fight that led me to staying over and hooking up with my little sister.

This time I’m gonna start talking about my times with my little sisters roommate/best friend. Now for clarity me and her had an on going thing for about 2 years never really getting together until about a year into it after I had lost my vCard and had gained some confidence. That being said I probably wouldn’t be where I am today without her and the boost to my self esteem that started with her.

Ok background I grew up in a very strict Christian home and because of that I for the majority of my life had thought that I should wait until marriage to have sex. I had a very long and serious relationship that had started in high school and went on until I was almost out of college. She was a missionaries kid so we never went further than a little bit of oral but it led me to be awkward about sexual situations sense I was under the impression that sex was something that only people “in love” could do.

[M]y Girl [F]riend? Or her best [F]riend? Part 3

[Part 1] (https://www.reddit.com/r/gonewildstories/comments/64ny5f/my_girl_friend_or_her_best_friend_decisions/)

[Part 2] (https://www.reddit.com/r/gonewildstories/comments/66fvi7/my_girl_friend_or_her_best_friend_part_2/)

The next morning, I got ready for school totally anticipating the surprise Jacqueline had to tell me. We all went to a private school so I was typically dressed in slacks and a polo shirt, and the girls usually wore skirts with polos. I pulled on my uniform faster than normal, grabbed my bag and left 30 minutes earlier than usual. My parents had already left for work so I didn’t even have to come up with an excuse for leaving so early. I hopped in my truck and headed on down to the park near school.

I remember it was gloomy overhead as I pulled up, the spring rain was constantly rolling in. Jacqueline was already there waiting for me. I climbed down from my truck just as it started to sprinkle. I got into the passenger seat of Jacqueline’s car and she immediately gave me a kiss and hug. She told me she missed me so much and that she couldn’t wait to see me. I kissed her back but felt strange that she was so happy to see me knowing that the day before I licked and fingered the hell out of her best friend. She could tell I was perplexed and ran with it. Instead of jumping right in to telling me her secret, she started small talk. She asked about my classes and homework, my truck… I couldn’t handle it. Finally I cut her off, and flat out asked her what her big secret was. She smirked at me with a devilish grin.

A good reason to go to your high school reunions [MF, oral]

I received the letter in the mail inviting me to my high school’s 15-year reunion. I had to double check that it had actually been 15 years. I don’t have the best memories from high school so I wasn’t even sure if I was going to make the trip back home to see a bunch of people that I didn’t talk to anymore.

After escaping high school l, graduated college, then grad school and found a job that I’m good at and pays well enough. Backtracking 15 years to rub elbows with people that didn’t like me then and will probably resent me now.

So why did I go? Part of me wanted to rub it in their faces. Part of me wanted to see the real life version of Facebook, the ones with rapidly receding hair lines, the ones who grew their beer bellies in collegiate drinking competitions, and the ones who peaked in high school.

Before I knew it my flight home and hotel were booked for that weekend in June. I spent most of the flight wondering who else would show up to this thing. Undoubtedly all the cool kids from high school would be there. But all the others like me are more or less a coin flip.

Drunk girl’s friend. Reward for the do-gooder. [MF]

So I sometimes hang out in Chicago between jobs. I work contract work all over the country and have / had a relationship with two college friends who both moved out there after graduation. In fact they were roommates there at one point. I’d love to tell you the story you’re hoping for but it’s not really sexy or adventurous. Just an easy friends with benefits thing we all kind of Adulted our way into. The arrangement was sorted out as dispassionately as a corporate merger. I mean we scheduled little 3 person talks from time to time, when one of them was in a relationship and I switched to staying with the other one when I was in town. To, you know, make sure we were all still emotional detached and shit.

They were not into the 3 way thing and I could respect it and never brought it up. It actually got worse when they became roommates because when I visited I had to stay on the couch unless one of them was out of town / in a relationship.

[MF] Dirty Long Distance – Part 1 [Long]

I don’t recall exactly how things got started with Amy. I know we met in high school as the far reaching periphery of a vast friend group. Rachel and Thomas were the main continent in the center of the map, surrounded by land clusters of friends from every walk of life imaginable. To speak in cliches a moment, it didn’t matter if someone was a nerd, a jock, a theater kid etc etc, they were welcomed by Rachel and Thomas. Meanwhile, Amy and I were almost poles. This wasn’t a designed occurrence we just didn’t have a lot of overlap socially. She seemed cordial from the dozen or fewer conversations we had, though.

So when I say that I don’t know exactly how things started with Amy, I mean that I’m not sure at what point we actually made a meaningful connection and why it was suddenly when I was in college, away from the continent of friends I once knew. It must have been something that I posted on Facebook. It’s been odd the handful of friendships/relationships that have spawned out of conversations over a Facebook status. I just know that for about a week, I spent a lot of time on Facebook, either waiting/hoping for Amy to get on or chatting with her.

[MF] [Cheating] Escalating with an ex

This is longer than I thought it would be, so I’ll post part 2 tomorrow.

I suppose I should start out saying I know that cheating is wrong, and I’m a terrible person. Let’s move past that.

Now, some background. I dated a girl in high school for a few weeks. It didn’t really get too serious because her family ended up moving to Florida. The craziest we ever got was making out on a couch at a church New Year’s party. I got a handful of her ass, and some under the shirt over the bra boob. She got to feel an outline of my erection through some blue jeans. Her name was Sara. In high school she was as skinny as a rail. Dark blonde hair, blue eyes. Her boobs were smaller than I’d prefer, but man did she have an ass.

[MF] Mourning sex

After college, a close friend hit a rough patch, and ended up committing suicide.

As one of the high school friends that stayed local, I had to contact everyone in our circle. I also hosted most people for the nights they were in town. The whole thing is a blur of airport trips, heavy drinking, the funereal, and a crazy party to celebrate his life.

Most people left the day after the services, or spent a day with their families. Only Sara stayed an extra night at my house, before her flight home.

We had been in high school band together, and then fooled around a few times over school breaks, but never slept together. Being exhausted from the past 3 days, we just stayed on the couch to watch movies. Pizza and wine were the menu of the night.

About halfway through our second bottle, we started to have the emotional conversations about our friend. She felt bad about not being around, and maybe she could have helped. I comforted her.