High School Archives — Page 138 of 805 — NSFW story

I told [m] girl[f]riend to blow a fellow Marine #TrueStory #California

~2012

A few years back when I was stationed in California I had a girlfriend who, to say the least, was open to just about anything. This is a true story of an unintentional 3sum that didn’t go as she had planned.

Actually she didn’t plan it at all, nor did I.

Lilly was a beautiful Hispanic girl, about 15 years younger than I was at the time. She was about five feet tall, weighed about 100 pounds even and had a set of aftermarket boobs that were probably too big for her natural frame. That said, this happened in Southern California and those proportions are not uncommon amongst the local population of beach bunnies.

Our relationship was accidental in that we met at a high school quarter mile running track late one night. I was a master sergeant in the Marines at the time and assigned to a general officer’s staff. I was a minion with no real responsibilities to the colonel that I worked for, other than to keep his staff officers on task by managing the shop and keeping them on timelines. I worked long days, usually going in at 06:30 and not leaving until about 12 hours later between 18:00 and 19:00. Most days I brought my lunch and rarely went to PT during duty hours. I was single and had no family responsibilities, no dog to walk, and no grass to cut; just work. Read more »

My high school gf (Jenny) and I reunite after a summer apart. (MF 18)

Jenny and I dated for most of high school. We were each other’s first real bf/gf, first kiss and everything else. For anyone who has not read other Jenny stories, she was petite, thin, short reddish brown hair, brown eyes, some freckles, small tits and nice legs and a nice ass. She was very cute.

Back when we were dating, I worked at a summer camp several hours away during the summer. This was pre-internet and pre-cellphone days, so other than actual mail, I pretty much disappeared for the summer. Every time I came back, Jenny I just picked up right where we left off.

One summer, I came home and I had some temporary job for the week before school started. I was driving to work on the second shift at some factory or warehouse one afternoon, when I heard honking behind me. I looked back and saw people waving frantically at me.

I pulled over into a small parking lot and the car followed me in. I got out of my car and immediately recognized the people in the other car. Jenny hopped out of the backseat of the car and ran over to me. We hugged and kissed in the parking lot, standing next to my car. She looked so hot. Read more »

Latina Cougar at a Sex Club

I was around 30 years old when this happened. I had joined a sex/swinger website called sls. A sex club had listed their events on sls. I signed up for one of the events and was approved by the host(s) or people in charge of it. I had attended a few sex clubs before and quickly realized that sls/sex clubs can often be tough for single men. I knew that I needed to be patient and have thick skin.

A woman that had also signed up for the same event contacted me on sls. Her name was Christine. We emailed/texted each other and agreed to meet each other at the event. I arrived at the sex club on a Saturday night. I was wearing a sweater and jeans. The sex club was at a converted 3 floor colonial house. The first floor had a room for food / drinks and a socializing room. The second floor had a dance room and a few sex rooms. The top floor had more sex rooms. Read more »

Sex with brothers babysitter[MF]

Last week when I(21M) went home to visit over spring break my parents told me that they are going out to dinners with some friends and that they hired a babysitter to babysit my younger brothers(10&12).

When I got home my sisters had already gone to sleep and only the babysitter was there. When I saw the babysitter I couldn’t help but notice how attractive she is. She had vibrant gray eyes with an olive colored skin and wavy blonde hair. She was wearing a loose brown tank top and some really short jean shorts.

We chatted for a little about life an through this I figured out that her bf broke up with her and that she was a senior in high school. She then put her hand of knee and came in to kiss me. We kissed as we continued to go down to bed in the basements.

I pressed her up against the wall and I removed her top. After this she leads me to the bed and she starts taking off her cloths. After that I began kissing her chest down to her stomach and then flipped her over and started eating her out. This lasted for a couple minutes. Read more »

Dad’s New Assistant

Shortly after I turned 18 my dad divorced my mom after 20 years of marriage. He was forty eight at the time and mom was forty six. They were high school sweethearts and married shortly after they graduated. They traveled around and worked real hard to save up enough where mom could stay home to watch me when I was born. I loved being the only child and loved having time alone with mom while dad traveled for work. We had some pretty special times together if you get what I mean.

Dad always had a couple of people that were his direct reports at work. Over the years he had quite a few in fact but recently he had one that was a young fresh faced college grad just starting her way in the professional world. He would have work people over for dinners and barbeques and she would always be the first one there and the last to leave. I have to admit she was pretty fucking hot and more than once I tried hitting on her. She always shot me down. I don’t know why. I was young and in great shape. Had well off parents and a great future ahead of me. Then it happened. Read more »

I fucked my first boyfriend only when he became my ex [FM]

*A warning: the lines between consent and non-consent might get blurry.*
———-

First boyfriend gave me [my first taste of cum](https://www.reddit.com/r/gonewildstories/comments/td5uj2/my_first_blowjob_or_i_swallowed_sperm_at_grandmas/), but when we dated I was not ready to go all the way. After our break up, we remained friends. At times, he flirted with me, which felt benign because he had moved to a different place and was getting plenty of quality pussy.

So, 7 years after our break up, I did not take him seriously when he said his main regret was not fucking me while we lived in the same city. I laughed it off. Well, it turns out he really did mean it, and this became a sticking point in our conversations for months. To his credit, he waited for me to break off a marriage prospect before he pounced.

“I thought he was the keeper. He would have made you a very happy wife.”

“There are some things I need to do before I commit at that level.”

“I sure hope fucking me is one of them.” Read more »

Meeting my French penpal (MF) (Fiction)

I had been exchanging letters with my penpal, Camille, since March 2020. Like a lot of people, I was stuck inside, on my own for much of the early part of the pandemic and I figured this would be a good way to pass the time. You have no idea how exciting receiving a handwritten letter is when the only thing you did that day was go to buy milk.

I found Camille through a penpal website that introduces people with similar interests. The way it worked was you put in your name, age and hobbies and you were matched with someone.

In our first letters, we explained who we were and what we did. I told her I was 19 years old and was a student. In her reply I learned she was 27 and an English teacher in a school in France. We hit it off (as much as you can through letters) immediately. I think she enjoyed hearing the perspective of someone slightly younger and I appreciated her advice. Read more »

[M]y [F]irst Time [Cheating] With Lily

If you want to skip to the action, go to the *****

This story takes place nearly a decade ago when I was 21. For a brief period of time I was sleeping with my OG high school crush, Lily. Lily and I had always been close friends in high school, but owing to my own nerdy demeanor and bad timing with our other relationships we had never actually gotten together during our teens. Like a lot of guys, I didn’t find my confidence until University, when girls started noticing and hitting on me for the first time.

Lily was an absolutely bombshell. 5′ 9″ (somewhat shorter than my 5′ 11″) with alabaster skin in contrast to her crimson red hair and sharp green eyes. Her classic hourglass frame and plush D breasts made her the subject of many people’s attention – guys and girls alike. She was the most outgoing bisexual girl I ever had the pleasure of seeing romantically, and was simultaneously flirty but dismissive in a way that just made everyone around her crave more of her attention. Read more »

18th Birthday Bukkake – Pt. 1 [Cumshots][Gangbang][Blowbang][Age Gap][Free Use][Public]

“Happy birthday, Nessie!” Mrs. Bauer called over her shoulder, departing arm-in-arm with her husband as he shimmied his steps to zip up his fly. The balding deli clerk had impatiently waited for the singing, presents, and cake to conclude so that the real reason everyone attended these festivities could begin. Then he’d hunched over me, sweating and stroking as I knelt in my birthday suit, until he went rigid and drizzled a warm, stringy load over my left eyebrow and cheek.

My singed-caramel skin was already spattered with the underwhelming climaxes of my family’s mailman and my old school bus driver, making Mr. Bauer the third “marker” of my womanhood for the day. Some girls were lucky to only have 5 or 10 guys from town show up for their 18th birthday party — but my dad was the former mayor, and I was cursed with unhideable F-cup tits above my slim waist. So my party was more of a backyard bash, and the streamer-strewn canopy my mother had ordered was packed with half the guys in town. Read more »