High School Archives — Page 166 of 805 — NSFW story

(MF) Fresh out of College (Cheating, Age Gap)

First time writer so be kind.

Brad was 22, fresh out of college and starting his first job as a high school teacher and athletic coach. During his orientation with the AD, he was introduced to Sara, the athletic secretary. She was in her early 40’s and was absolutely gorgeous. It took all Brad could do when he saw her to make sure he didn’t stare too long.

Well the school year started and Brad was having tryouts, collecting paperwork and doing all the administrative things coaches hate. Although Brad was kind of enjoying it. He spent a lot of time in Sara’s office, turning in stuff, asking questions and trying his best to flirt without being over the top or creepy.

Brad was a good looking guy. He was 5’10” 185 pounds. Hardly an ounce of fat on him. Almost every morning he’d go in and see Sara. At first all they really talked about was sports, but it didn’t take long for conversation to become personal. Brad found out Sara was in a loveless marriage. She had two daughters. Her husband traveled a lot and was only home one week per month. He was a great provider and Sara really didn’t have to work, but working at the high school gave her something to do, but still gave her lots of time off. Brad on the other hand was single, he had ended his year long relationship with his college girlfriend before graduation since they were headed down different paths. Read more »

[MF] Ryan and His Stepsister Part 20

Ryan was very excited about the eventful week that was in store for him. He was going to see Joanne on Friday and hopefully get to fuck her again. Maddy was going to meet her and also share her plans for all of them as well. He wondered what exactly were Maddy’s plans. Was she going to be a bitch to Joanne? Was she going to treat her like she did him?

Ryan’s cock twitched at the thought. He would love to see Maddy dominate a woman like she did him. He wondered if she had ever dominated a woman before. He had seen her be a bitch to several girls while they were in high school. She had even picked on several stuck up girls who were afraid of her but never like how she treated him.

He was also thinking about the party on Saturday. Maddy had given him the task to eat a random girl out and film it too. This was crazy! He had no idea how he was going to do that. He had never eaten a stranger out before. It had always been a girlfriend or a girl that he hooked up with. Read more »

My First Threesome (with two of my former high school teachers) [FM]

This story is embarrassing to write about….not because of the sex, but because of how naive and stupid i was. Also, warning….i tend to write long and detailed. But every bit is true.

To give you an idea of how much of a weird girl i was…..i visited my old high school after I graduated and went to college. There was a teacher who I had a crush on since, honestly, the first day of my freshman year. He was smart and cute and a good teacher and I sorta low-key obsessed over him. But nothing ever happened.

So I graduate….I go to college and come home for a break and go to my old school to visit. And of course I visit Mr. X. And we have a great talk, like we always did. And it was great to just talk to someone about school and my insecurities and my goals and all of that. And he was a great listener and it was just great. And finally he said he had to go, but would i like to have dinner that night. Read more »

Her First Fuck

A lot of my friends are wanting to know about the first time my wife ever had sex. They wanted to know if it was with me or someone else. I told them it was not with me but with her high school boyfriend.

My wife dated her boyfriend on and off through high school. You know how teenagers can be with relationships, one day they’re together the next day they’re not. The wife and I have had conversations about our sexual experiences with others, that is when she told me about her first-time having sex. Keep in mind this is a true story of my wife and when she lost her virginity.

She grew up in a small town in north Georgia where high school football was the thing to do on Friday nights. She and her boyfriend would all go to the Dairy Queen after the game just to hang out in the parking lot with their friends. There were many nights where they would leave the game and she would give him a quick blowjob on their way to Dairy Queen. She would talk to her friends about him and their relationship as teenage girls do. Her friends were doing the same with their boyfriends, but there were a few that had already had sex. This Friday night she told me about was different than the others. Read more »

I [20M] took a babysitting job, didn’t expect their older sister [18F] to be so hot [MF]

I’m gonna edit this to get around the post size limit

Like the title suggests, this story starts with me getting hired as a babysitter. After graduating high school my family didn’t have enough money for college so I ended up working in customer service, and I babysat occasionally for a little extra cash. The kids I was babysitting in this case were 4, 8, and 13, but they also had an older sister who was a high school senior (18F), I’ll call her Maisie.

. I arrived at 5:00 and the parents said they’d be back around midnight and left, telling me that the kids’ bedtimes were 7, 9, and 10 in ascending order of age, and dinner was usually around 5:30, they told me to order a pizza, and that they had an indoor pool in case any of the kids wanted to go swimming while I was there. I brought a swimsuit in case the kids did decide to swim. Read more »

[F] Secretly Finding Hubby’s Porn Stash

This took place a while back, around the time we had just gotten married, but the day I discovered my hubby’s porn stash was the equivalent of me getting the cheat code for our sex lives. I’m well aware that there are competing views when it comes to guys and porn stashes but hear me out, this was a game-changer. He had it stored in a random folder, which I figure is pretty common for most guys, and it wasn’t till I was trying to clear file space that I happened to stumble upon it. At first, I was a little shocked because the folder size was in the 100’s of gigs. Truthfully I didn’t understand why he needed all of it, seeing as they were mainly photo sets of models with a few videos sprinkled amongst them.

At that point, my brain was telling me to back out and just let him keep his secrets, but my naughty side told me to keep going down the rabbit hole. Needless to say, I spent close to two hours looking at these models, watching porn videos, and learning all about what my husband loves in a sexual sense and some of the things he wanted to try. BDSM and public play being major ones. So after spending those hours fingering myself and enjoying a few orgasms, I started taking notes. Locations, toys, equipment, everything I could think of to make his fantasies a reality, and it’s really paid off for the better. Read more »

My (20M) girlfriend’s (21F) best friend (21F) gets dumped [FM][FFM] (long) PART 1

This is a story about a night I never expected to happen, and is among the top material in my spank bank. If you want to skip ahead to the sexual stuff, see the ****** below. I think this will be three parts.

A cool April evening and my girlfriend, Julia was coming over to spend the night. Julia and I were high school sweethearts, started to date senior year and being each other’s “first” for most things sexual. I had (stupidly) hooked up with someone at a party a year before Julia and I got together, so had sex once before we got together. I was her first for pretty much everything on a typical sexual bucket list.

My family was out of town and so we had the house to ourselves and intended on making use of that time to do what horny 20 year olds do. She arrived in the early evening in a pair of yoga pants and a sweater, not expecting to do much other than take them off. I should describe Julia. Your classic “girl next door” vibe, with light brown hair, curvy in the right places with a big but strong ass from her gymnastics and dance background. Julia had hair that teasingly covered her ample, C cup breasts, which had a great pear shape and large, very sensitive, nipples. She always kept her pussy shaved bare. Her fair complexion was not yet spotted with her summer freckles as we were just emerging from a freezing winter. As we had been together for a few years, Julia often kept a few things at my place. Read more »

The Lies We Tell Ourselves (M/F) (Cheating)

This is for u/Ji11Lash

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We used to be right for one another. We used to be a rock for each other. But as things goes, we grew apart. I sort of grew up while he, well, he didn’t.

Freshman year of high school is where I met Geoff. I was a sort of the chubby girl that someone wouldn’t even bat an eye for, let alone give the time of their day. I was kind of nerdy, but then again what girl wasn’t back then, and Geoff and I had the same interest in a lot of things. So, he and I grew close and eventually he asked me to be his girlfriend, and I gladly accepted him.

Then I started working out. I went to the gym, I went to yoga, I went to kickboxing, I went to a lot of fitness and classes offered by gyms. I weight 190 Lbs. at 5’4, and by the time high school was finished I weighed about 120 and was fit and tight in all the right places. I had abs and muscles and my thighs looked oh-so-fucking good! Read more »