Tag: High School

[Les] The New Girl [trap]

“Come on, bitch, live a little!” Sarah said, nudging me in the ribs as she waved at the two girls. “Forget about your dick ex-husband, forget about his stupid fucking cunt girlfriend, and let your fucking hair down for a change.”

Sarah had a mouth on her like nobody else I knew. Tall and quick, but slender as a broomstick and an unrepentant and completely open lesbian, when bullies tried cowing her in high school her fists were of little use, so she learned to use her mouth instead, and she did it well.

“She’s actually pretty nice, …” I protested weakly as I sipped from my cranberry vodka.

“Apart from the homewrecking?” Sarah suggested as she gestured to the bartender for some jelly shooters.

“Obviously.” I said with a shrug.

Somehow Sarah had talked me into going out with her tonight, to The Pink Cavern, the town’s foremost lesbian bar. It was more of a club, really, and the bright lights and hopping music had a tendency to ensnare cruisers from Sorority Row who were either oblivious to what the place was, or looking for a thrill. Tonight was no different, and on the dance floor a small clump of coeds in short skirts were dancing along, strong drinks and handsy moves lavished on them by the regular clientele. Read more »

Brother and Sister Roleplay

I created this the other day thinking about if I had a sister. Sadly I only have brothers, I think the taboo is beyond hot! If you like it I have the other half of the story that I would love to pass on to you. Anyways, take a read:

Being home blew. So. Fucking. Hard.

Okay, I couldn’t blame my parents, honestly, they helped put me through college and in the process lost their gorgeous, three bedroom, three story country house and now live in a slummy two bedroom house in town. Since my sister is just now in her senior year of high school she still lives at home, so she’s afforded the second bedroom as my parents have the other.
Which means I’m relegated to the living room couch. Which, again, isn’t terrible, and most of this is the thesis of a first world problem, but sometimes I hate the loss of privacy.

In the old home during my late, sleepless nights I’d splay out on my king sized bed, basking in the light of my laptop screen with my basement bedroom door closed, away from everyone, fervently jacking off to whatever erotic videos I could find on the internet. Sometimes I’d even get daring and hope on cam and let some lucky lady see my youthful stomach clench up as I softly moan and spray cum all over my happy trail, and chest. Read more »

Brother and Sister roleplay

I created this the other day thinking about if I had a sister. Sadly I only have brothers, I think the taboo is beyond hot! If you like it I have the other half of the story that I would love to pass on to you. Anyways, take a read:

Being home blew. So. Fucking. Hard.

Okay, I couldn’t blame my parents, honestly, they helped put me through college and in the process lost their gorgeous, three bedroom, three story country house and now live in a slummy two bedroom house in town. Since my sister is just now in her senior year of high school she still lives at home, so she’s afforded the second bedroom as my parents have the other.

Which means I’m relegated to the living room couch. Which, again, isn’t terrible, and most of this is the thesis of a first world problem, but sometimes I hate the loss of privacy.

In the old home during my late, sleepless nights I’d splay out on my king sized bed, basking in the light of my laptop screen with my basement bedroom door closed, away from everyone, fervently jacking off to whatever erotic videos I could find on the internet. Sometimes I’d even get daring and hope on cam and let some lucky lady see my youthful stomach clench up as I softly moan and spray cum all over my happy trail, and chest. Read more »

Hooking up with my old Monster Cock fling and his Wife [FFM]

I don’t know if any of you have ever gotten caught red handed writing your Gone Wild Stories, but last week that happened to me. I was back in my hometown for Thanksgiving with my parents. I went out to a bar for black Wednesday with my youngest sister. These kinds of things are always kind of awkward: you see people you knew in high school, some more attractive, some less. In my case, I have to fend off the creepiest of the creepers at the bar, while still looking for some kind of prospect.

 

In high school, I had a reputation… I fucked a lot of guys (33 by graduation by my count) and it stuck. I’m 27 now, have a good job, and have fucked plenty more men. But the creepiest of townie lowlifes with multiple DUIs still remember high school Ashleigh. Slut shame me if you want, but no one deserves aggressive advances from fat hairy guys who they barely knew from grammar school. Thank God, I saw some people I could talk to.

  Read more »

[MF] (18yrs) Dropped my girlfriend off before prom party to fuck my best girl friend at the party..

This is my first ever experience I have shared so please bear with me if it is not too captivating. The sexual parts are towards the bottom but I tried to have you guys have the clearest picture about who and what is happening and the context.

Alright to paint the setting, it was the first week of May 2016 and my senior prom was finally coming up. To keep up privacy, my girlfriend in the time frame of this (and current one, lol) will be named S and my best friend will be named M (she’s a girl, thought i would point that out). Read more »

The Cabo Maid [M]

The Cabo Maid

When I was in high school my family took a vacation to Cabo. The resort we stayed at was really nice, it had villas at one end and a separate hotel at the other. Being a family of 5, we were in one of the villas which didn’t have maid service, which who knows why my mom would be a fan of cleaning for everyone even while on vacation.

So the hotel was a couple minute walk down the boardwalk. There they had the big pool with the swim up bar, the slide, and the rest of the fun stuff. So for the week we were there, we spent most of our time at that pool or down at the beach.

Sleeping on a sofa bed in a two bedroom room with 4 of your family members leaves you absolutely no privacy, so a couple days in I was getting really horny, and spending days at the pool watching women walk by makes it no easier. Nor does having only a few girls my age either. Read more »

Summers can be hot. But, one summer it ignited a spark with an old friend. [MF]

Hope everyone is having a good weekend! I can’t sleep worth a fuck and since my last story got a good number of votes, I wanted to share again. This happened when I was 18 and it’s definitely one of my hotter experiences.

Like I’ve said in past stories, I was kind of a late bloomer. I had the sexual appetite that most teenage boys have, but my confidence seemed inexistent. Sure I had plenty of friends that were girls, but I got the vibe they just looked at me as a brother. Even after losing my virginity at 16, I still had zero confidence. I don’t know why, but it just didn’t spark. I finally did get enough courage to ask out a girl who I would date for over a year. We had a lot of fun and the sex was great. I think this is what helped me become more comfortable later on with talking to women, well the ones I found attractive. So, once I graduated high school and my relationship ended within the month following, I’d be lying if I said I wasn’t heartbroken. After a year of being exclusive to one person, you would be too. Looking back I believe it was one of the better things I’ve done, but at that time I felt like I truly loved her. Anyway, this isn’t about her. It’s about one of childhood friends. Read more »

The time I fucked my roommate… a cumming of age tale [MF]

This all started when I had just graduated high school in Portland, OR and decided I was ready to live on my own. The initially plan fell through and I wound up living on some friend’s couches, but because most of my friends were female and I was an 18 year old, I looked to find a place of my own. Meanwhile I was working part time and signed up for classes at the community college during the summer. It was here I met a girl in her mid 20’s (I will call her Sarah), who just happened to be looking for another roommate (to split rent between herself and another girl named Tiffany). It all seemed fine and dandy, I would pay $200 a month to have a room with no door to stash my bike, mattress and a trunk of clothes, Read more »

Married co-worker [F] and the young man [M]: an affair (LONG)

Everything I’ve written previously has been about my collegiate experiences–my first time with an older woman ([1](https://www.reddit.com/r/gonewildstories/comments/598ol8/late_40s_f_and_the_college_boy_m_a_first_for_both/), [2](https://www.reddit.com/r/gonewildstories/comments/59xwkg/late_40s_f_and_the_college_boy_m_a_first_for_both/)) and about [an experience with an ex girlfriend, where I gave her an orgasm in front of her dad without him realizing](https://www.reddit.com/r/gonewildstories/comments/5aykbh/orgasm_in_front_of_girlfriends_unknowing_dadmf/) (most of the commenters believe he knew–but I still naively don’t think so!). I have to confess the following experience does come with a little bit of guilt because she was married (it’s so weird how the married also makes it exponentially sexier, which she did specifically mentioned quite a few times). Our first interaction was last March and we decided to chill out recently.

As a reminder, I was a tall, gawky kid growing up, with glasses and an overbite. Then I wrestled throughout high school, got contacts, and dental work fixed my alignment to where I’m actually a pretty good looking guy (I’m told I look like the senior in Sixteen Candles), but I still have the perception of myself as a gawky kid with glasses and can still be somewhat shy until engaged, and alternate between overconfidence and no confidence. Read more »

Lonely, but not when you hold me. [Str8] [F] [m]

“Just tell him Jeremy.”

“It’s really not that great of a story and I don’t even know if I like revisiting the memories anymore,” I sighed.

I looked from John’s insistent pleading face over to Kevin’s face of shock and awe.

“Fine,” I muttered. “I will tell it on the condition there are no stupid questions. None. For one, I probably don’t even remember some of the specifics and the memory has gone from real to fantasy because it was so long ago.”

I let out a breath and started, “It was with the art teacher Mrs. Nichols. I loved that art class from the start. I sat next to this hilarious 4chan meme spewing autistic fat kid and a tall attractive alt girl trying super hard to be unique. She still used the perks of being an attractive high school girl though. They were a hilarious combination. I’m sure the three of us seemed hilarious to everyone else looking on as we were always laughing, but most of the talking was between them two.”

“Jeremy. He doesn’t care about that shit.”

I looked at Kevin who seemed to be interested either way. Whatever that idiot John told him must have been an exaggeration. Read more »