Tag: High School

My boyfriend was hiding under our bed while I [F27] cheated on him with a college athlete with a very large penis. We broke up shortly thereafter. [MF]

I was encouraged by many to write a few stories here so here it goes my first. This was 5 years ago, so I was 22.

I dated a guy for 4 1/2 years, starting the end of our junior year of high school. I still think he’s my soulmate. We dated throughout our first three years of college, which was easy because we went to separate colleges in the same city. And lived together. We both came from Chinese-American backgrounds, and it felt effortless. Except the sex. And it got worse the further we got into college, and the more schoolwork he carried on. He became very insecure of the guys that would leave me messages on FB and IG.

One of the guys on our college water polo team had seen me and chatted me up in the dining hall several times. I was never with my BF when he’d approach me. He slid into my DMs and we ended up flirting for about a month. He was gorgeous; tall, huge shoulders, swimmer’s body. He told me he had a large penis but I always changed the subject until he sent me a dick pic. And he wasn’t lying. Read more »

For Medical Purposes [MF, cheating, anal]

I mentioned my niece, Ally, in another story–I’ve got more to tell about her, but this one is about her mom from a few years ago. Dani was my ex-wife’s baby sister–7 years younger and completely different appearance. My ex-wife was legitimately beautiful in a classic sense–she had long legs and long brown hair to go with deep blue eyes. She was tall with curves and her ass was hard to ignore. Dani was cute, short, and physically fit but unremarkable. I always enjoyed seeing her walk by in a bathing suit during family gatherings, but she never was the type you’d break stride trying to get a look at. Still, whether it was the taboo aspect or just curiosity about how she compared to her sister, I had thought of her more than once when I was on the road and needed some inspiration.

Over the years, I think my apparent indifference to her took on more significance as she got older and had two kids–she wasn’t getting the minor attention she had before. Her husband, David, had taken advantage of her long shifts as a nurse to make time with the babysitters and then their daughter’s friends with teasing remarks that later turned out to be more involved. No plunging necklines or short shorts could change the fact that her sex appeal seemed to be fading fast. Read more »

I [34M]ustered up the courage to do exactly what she asked [33F]or. [MF]

I discovered my favorite sex act – deepthroat – when I found videos of the G.O.A.T. Heather from iDeepthroat, back in my college days. There’s something about watching someone looking up at you, with your cock vanished into their mouth. In general, I prefer oral sex over all other sexual acts, and could basically 69 all day with the right partner. It’s been difficult to find a partner who can satisfy my desire, but with … her … I had a chance. This is how it happened.

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Quick aside – this is a true story to the best of my memory, though I’m changing the names of the people involved just so I feel more comfortable. This story also happened a number of years ago but I will *never* forget it. Going to give some backstory and build-up here, but if you really can’t wait, scroll down to the next line break after this one to more or less get into the action.

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Bianca, the painter. [FM], [voy], [oral],

I really had to be in that online meeting. It was a key and unchangeable meeting. I needed an internet connection.

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I was a second year History student. I signed up to that internship just to have something to show on my CV. I was enjoying it, but they relied on the online meetings too much.

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I happened to be in a nice little town by the sea. My aunt invited me, last minute, to go with her and my little cousins for the weekend. This meeting was really important and kind of mandatory, but I just wanted to be in the beach so badly, who doesn’t? I accepted, but then we discovered that our condo was having issues with the WiFi. So I still had to find some way to have my videoconference. My aunt figured out I could go to the house of a very close friend of hers.

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Almost getting caught on the boat. [MF]

One of the many perks of graduating college without any debt and inheriting a house from a family friend who had no kids, is that I have been able to spend my pay foolishly as my mother puts it. Last summer I bought a used speedboat and have spent a lot of time over the last 2 summers just relaxing on the river with friends and family; that provides the opportunity for this story/event to take place.

Earlier this week I ( 32, “Dad Bod” Teacher) had been talking to my Coworker MILF FWB Kat (45, 38b) and she was complaining about how her and her sons hadn’t been able to get over to their beach condo due to rentals and how she was bored. I had mentioned my boat before and I said to her, “Why don’t you and the boys and I go out on my boat tomorrow for the afternoon? It’ll be good to catch up with Brad (oldest son) and see Grayson (youngest son) before the school year starts.” Kat responded back, “Well Grayson has to work, but Brad would probably be game, I’ll get back to you.” A few hours later, my phone dinged and showed a message from Kat that said, “ We are good for tomorrow, but Brad want’s to know if Ashley (his girlfriend) can come too?) Since I had both Brad and Ashley in class as high school seniors and now they were juniors in college, I told her, “That’s fine with me. We can just leave from my house around 10:30, just come on over around then.” Read more »

I [F] invite a shy college freshman [M] along for a night of naked fun with friends, then take him home and let him cum on my face and creampie me [MF]

I’m gonna try something slightly different and tell a more personal story. This was a great night for a lot of reasons, not just sexual ones. There’s a little bit more backstory, but it gets incredibly hot, I promise. And I think it’s a cute story.

I was probably 20 at this point, it was the start of my junior year of college, and I had been putting off my required math classes for the last two years; I hadn’t done a single one. I started in college pre-cal. Naturally, most of the class was freshman, since you’re not supposed to wait to take this class.

On the first day, I sat down next to a boy named David. Well, not quite “next to.” It was a large lecture hall so there were a few spaces between everybody. He was young, with dark hair. He was super hot, like that cute, boyish kind of hot. He had a great, kind of prominent nose, and these Ryan Gosling looking eyes. He dressed nicely. Kinda professional vibes. The freshmen are always kinda try-hardy in those nice programs. After about two weeks of never talking to him, I noticed he came in with a coffee-to-go cup one day. I decided to make some small talk. “Where’d you get that?” I asked. “Oh um, the engineering building has a little cafe. It’s fancier than the little dining hall mini cafes.” “Oh, cool. It smells great.” “You want me to bring you one next class?” he asked. Read more »

Bestfriends Forever [M/F] [Fiction]

High school had officially ended for me and i was glad to officially being done with waking up early and taking a dirty bus to school everyday while counting down the minutes to lunch and for school to end. I was done with anything related to school.

BUT that also means i didn’t want to go to college. This meant that i had to take another boring bus to my dead end job at a restaurant, yet again counting down the hours to my lunch break and then till my shift ends. The only think I’ve been looking foward to from my shitty job is my co worker Mallory. Now there were alot of beautiful waitress here but mallory was the one who trained me when i first started here. We got pretty close and exchanged phone numbers like on the second week of me working there. We become fast friends after that and every lunch break, we managed to always have the exact 30 minutes off. Those 1,800 seconds are the best seconds I’ve ever had. Read more »

Breaking in the young girl, part 1[Str8][Mf][Mdom][Fsub][oral][reluc]

This is the next story I wanted to share. My first couple of stories were about sisters, and there is another story to tell about that family, but there are some more stories I should share first for that one to make sense. I’ll include the links to the other stories in the comments, so I’ll keep the intro short. These stories are a mix of fiction and non-fiction.

This story takes place when I was just out of high school, but I won’t include ages of those involved. I’m fairly tall, and at that time I was pretty fit from playing some sports in high school. I’m lucky to have a nice sized dick, at about 7″ and girthy. At the time I’ll admit I was pretty arrogant and self centered. I thought I was pretty experienced with sex, but a lot of what I thought was good came from porn and was obviously not the right way to treat women. I’m not proud of how I acted in this story, but it led to some pretty hot sex from my side. Read more »

Straight but feminine boy raped by bullies [non-con][forced feminization]

This story is a work of fiction and all characters are 18+

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It’s prom night and this torturous high school journey was finally going to end. Fives years of being bullied and alone. Five years of ridicule just because of my naturally feminine body and smooth hairless skin. Granted, with my shoulder length hair, slim body and delicate facial features, nobody would bat an eye if I accidentally walked into the girls washroom. I suppose my timid demeanour and shyness are inviting qualities for bullies who get off on the feeling of superiority.

My main bully – let’s call him E – was very popular, the captain of the basket ball team, in fact. He was also decently smart. He never bullied me in the open, where he risks tainting his reputation. He and his lackeys find opportunities when we’re alone to push me around. They call me cruel names, give me wedgies, and sometimes pull my pants down in the washroom to laugh at my small penis. They even took pictures of me with my pants down, and then send them to me occasionally to remind me what could happen if I tell my parents or the teachers about their behaviour. Read more »

My insatiable high school bf part 2 [MF]

After writing about it the other night, I decided to do another installment about my high school bf and I (MF both 18 at the time). He was horny and adventurous enough that I have plenty of material from our time together. It helps that I was so new to sex (and totally new to good sex) at the time that those memories really stick out in my head.

Even though he had never had sex before me, he was a very horny teen who watched a ton of porn. Where this can often be a not-so-great thing, in his case it really increased his stamina from what it typically would be for a virgin, and it made him curious and open-minded about a lot of different things. There were always new sexy things he wanted me to try, and he was an animal in the sack from the word go. Read more »