Tag: High School

Sucking on [m]y best [f]riend’s tits

First time posting and it is a true story, so apologies if it isn’t written out the best.

The summer after freshman year of college my group of friends from high school decided to rent some cabins at the lake, have a non-stop party for a few days. Since we were all broke we rented to cheapest cabins which we could find, and while they weren’t nice they were clean and air conditioned. There were around 25 of us split between four cabins, though people had to share beds.

Literally all we did the entire time was drink our asses off, hanging out on the dock during the day and cabins in the evenings. After three straight days of this I was trying hard to Party the last night but it just wasn’t happening. Most of my friends were still going strong but I couldn’t keep up. I realized my friend Jane (not her real name) felt the same way, so we decided to head to one of the cabins where no one was partying and watch a movie. The only vcr (it wasn’t that long ago but like I said, this place was cheap) was in a bedroom so that’s where we headed. Read more »

[MF] Sharing stories of the girls I’ve been with (26M)

You know, before now I’ve never actually gone over, in detail my sexual history with anyone!

I’d like to go over girls I’ve had sex with, it turns me on sharing details and I’ve never actually sat down and gone over it all with anyone before! I’d love to hear your stories in response, I always like some interaction. Feel free to ask questions and comments about my experiences!

I’m trying to keep it realistic, I don’t like huge lists of bragadocoious, unrealistic sexploits and this is not supposed to be one of them. We aren’t all porn stars here.

That being said, I was in a fraternity and on the football team so I did have plenty of encounters. There’s stereotyping for a reason haha. And for the record I measure 6in long by 6in girth, for some girls that’s nothing for other’s it can be a bit much!

Kira –

The first girl I ever had sex with, she was a year+ older than me, which in highschool was a big deal! She was my female best friend’s, best friend. She had a reputation for getting around but actually talking with her she is the nicest girl who is just truly interested in life. Read more »

Sex with Teacher in Cuba

When I was a senior in high school, a trip to Cuba was arranged for everyone in AP History – about 60 students in all. I didn’t overly care about Cuba, but I appreciated the chance to get away to a hot climate and to have a break from school and my family. Most importantly, my favorite teacher — the one I had a crush on, lusted after, and frequently masturbated to, Ms. Gordon — was going to be there. We actually had a great rapport in class, and I looked forward to the prospect of bantering with her as we toured and dined in a hot foreign country where, I hoped, she might wear some clothes that showed off her large breasts.

Deep down, as much as I joked with my friends about how hot she was, this was just a fantasy. I had a loving girlfriend, Rebecca, that I was committed to. Besides, I was only 18 – I wouldn’t know what to do with a grown woman if I had her. Ms. Gordon I knew had just turned 40, and had dark hair, very full breasts, and a slightly curvy figure without being at all fat. She was authoritative, but if she liked you and you didn’t give her problems you’d find out that she was really cool and had a sharp sense of humor. History was my last class of the day, and I’d often hang around and chat with her about TV shows or whatever else. She was the first adult I ever met that I could relate to. Read more »

Community Pool’s Shower [MF]

Hello GWS! Sorry for any issues with the format, I’m on mobile.

Anyway, this story takes place last summer (after freshman year of college) I was visiting a friend from high school that I had been friends with since middle school. A little about myself, I’m a 6’3″ white guy, about 195 pounds, blonde hair, blue eyes, and a 7 inch tool. ANYWAY, On this particular day, it was nearly 100 degrees out so we decided to go to the pool in his community. After being there for about an hour or so, we see two girls from high school. Olivia and her friend who’s name escapes me.

Now, I had a huge crush on Olivia since 9th grade and she looked fantastic. She walks in with a loose fitting floral top and a pair of running shorts, immediately my eyes are fixated on her, I can’t stop staring and she hasn’t even taken her top off to jump in. While we were in high school, Olivia had perky B cups that looked much bigger on her 5’2″ frame. But since then, she had become a thick goddess with long blonde hair, A nice big butt and what I would later find out to be C cups. As she begins to get ready to get in the water, I walk over to say hello. As I walk over, she takes off her top to reveal a tight black bikini that left little room for imagination. I had to keep the introduction short as I was afraid she would see my semi erect state begin to show through my trunks. Read more »

Neighbor, Sir: Part 3 [D/s, MDom, FSub]

He was described as an odd child: sensitive, compassionate, and decidedly withdrawn. Seeming to get on with adults better than children, he preferred to stay inside during recess and help Sister Mary prepare the classroom for the afternoon classes. She called him “charming” and “mischievous”, sometimes even “devilish”, even though he was never in any real trouble to her or anyone else. Once, during her morning coffee with the other nuns and faculty, however, she confided the strange influence this six-year old boy had on her. It unnerved her, sometimes, how strong the desire to be in his favor, to anticipate and attempt to meet his needs. She was a professional with 20 years of experience, and she knew she should not choose favorites. He did not overtly seek her attention; instead, he appeared to be the kind of child who preferred not to stand out, yet he seemed to speak to a part of her that she originally associated with motherhood, something that, because of her vows, she would never experience. Further reflection revealed that this child appealed to a deeper desire within her. She never considered any interaction with the boy inappropriate; however, she was unsettled by how she was drawn to him. Read more »

Neighbor, Sir: Part 3 [D/s, MDom, FSub]

He was described as an odd child: sensitive, compassionate, and decidedly withdrawn. Seeming to get on with adults better than children, he preferred to stay inside during recess and help Sister Mary prepare the classroom for the afternoon classes. She called him “charming” and “mischievous”, sometimes even “devilish”, even though he was never in any real trouble to her or anyone else. Once, during her morning coffee with the other nuns and faculty, however, she confided the strange influence this six-year old boy had on her. It unnerved her, sometimes, how strong the desire to be in his favor, to anticipate and attempt to meet his needs. She was a professional with 20 years of experience, and she knew she should not choose favorites. He did not overtly seek her attention; instead, he appeared to be the kind of child who preferred not to stand out, yet he seemed to speak to a part of her that she originally associated with motherhood, something that, because of her vows, she would never experience. Further reflection revealed that this child appealed to a deeper desire within her. She never considered any interaction with the boy inappropriate; however, she was unsettled by how she was drawn to him. Read more »

[F][Masturbation][Anal] Young me discovering anal masturbation

Heyy everyone! <3

This story is about me. I was a younger girl in high school at the time. I was just getting around the age where I was sexually piqued. As my body developed, so did my interests in the sexual sphere of life. I spoke to friends of mine who would describe their sexual experiences. It wasn’t that I was desperate to relate. I was desperate to find out more.

A bit less than a week before this story happens, I began masturbating. This came after many fantasies about both boys and girls, and the sexual acts known to me at the time. Primarily, I was a more submissive role in these fantasies. The boy/girl performing the act would often be pleasuring me for many, many minutes on end. Unfortunately, it took me quite some time to discover that I could enhance this experience via masturbation.

I looked up some wikiHow-style articles on the subject. I watched girls talk about it on YouTube, I read articles and even looked at a couple pictures (insane for me a few years ago). I’ll write about my first vaginal masturbation at a later time. For now, I’d like to start with this story, because it was a whole different level. It was a much different experience. Read more »

My Trip for Pizza Reveals A Teen’s Secret (M/mf, voy, 18+, Longish)

I had been married to my new wife for 3 years when her son Mark started dating Tiffany. They were both 18, seniors in a catholic high school, promise rings and chastity pledges all around and heading to the same college upstate. Early on they had a lot of study dates, and this story begins on one of those. My wife was working late and the two were studying on the couch under a blanket while I watched TV, just a normal Thursday evening.

My stepson was average-looking, but Tiffany was nearly an archetypal male fantasy come to life. 5’6″ but usually stood 5’8″, couldn’t have been a pound over 110. Her bra tag says 34B but it looks a bit small on her. Cheerleader, of course, not the head cheerleader but definitely the most attractive. Better than A-student and they go to a tough school. I have no idea how Mark found such a beauty, but good for him! Read more »

Annie and Jess, high school besties [ff] [anal] [oral] [mast] [fist] [pee] [spit]

Annie and Jess, 18 year old seniors in high school, spent almost every weekend together. They’d order a pizza on Friday, do their nails, talk about boys they liked, give each other mud mask facials, and eventually, change and snuggle up and go to sleep.

But you’d be fooling yourself if you didn’t think there was some sexual tension between them. They’d always linger a little when they hugged. In bed, they’d run their fingers through each other’s hair and breath on their necks as they snuggled.

Neither one was courageous enough to make a move, though, until one night, Jess’ parents went out of town and Annie came over. Annie, horny as all get out, wanted to fool around.

“I wish I had a boyfriend,” she said. “I’m super horny.”

“Oh my god, me too,” Annie said as she went to Jess’ dad’s liquor cabinet and opened it.

“What are you doing?” Jess asked.

“Shhh, it’s okay. I just want to try something.”

Annie pulled out a nearly full bottle of vodka and took a small sip. She handed the bottle to Jess, who also took a sip. They took a few more small sips, giggling, blushing nervously. Read more »

[MF] Home for the Holidays – Part 2

Part 1 can be found [here](https://www.reddit.com/r/gonewildstories/comments/7h98b1/mf_home_for_the_holidays_part_1/)

Ok, so, quick recap of Part 1: I go home for the holidays, run into old high school GF and her still MILFy mom. Find out old GF is single again, we drink, and have some crazy sex like we used to. Old GF manages to forget her skirt in my hotel room, but leaves no way to get in touch with her, so I head over to said milfy mom’s house.

So, I’m heading over to Cynthia’s house going through how i’ll bring this up. I go through multiple conversations in my head, but somehow they end in versions of “Hey, I just fucked Ally, again, and wanted her number so we can arrange it again soon”. As I turn down the street I realize l can just BS some technocrap about making sure her wifi was still working. I walk up to the door still half-thinking this is a bad idea, but when Cynthia answers the door in a skimpy bathrobe, I clearly realize this was the best choice I could have made. Read more »