High School Archives — Page 299 of 805 — NSFW story

Her revenge 21[F]uck using 19[M]e

This happened a little over 10 years ago. I had been unemployed for about a year. I was trying to take any job I could. I had just started seeing this girl who I knew from high school again. For privacy reasons my girlfriend’s name will be Mai. Back in high school I almost dated Mai’s best friend Tea(also fake name), who we will get back to in this story, but because Mai told me in high school Tea didn’t see me like that I never pursued her. I than started to see Mai but it didn’t last long. Fast forward 5 year me and Tea had started seeing each other again.

I had ran into Mai at a party, one thing led to another and we ended up together that night in a bathroom talking for hours, which led to sex that night. All I remember from that encounter is we started fucking in the bathroom and we ended up in a bed room some how. We were both pretty drunk, so when we woke up we just kind laughed because she only had her shoes on, while I was naked. Read more »

24[M] Corrupted by [F]emale Colleague – Part 5 – Enter Chloe…

Following on from the [previous chapter](https://www.reddit.com/r/gonewildstories/comments/ll1ptt/24m_corrupted_by_an_older_f_colleague_part_4_the/). Thanks to everyone who has enjoyed so far, appreciate they can be quite long but when you’re bored, locked down at home working, it’s quite fun thinking to the good old days when you could actually have casual sex! [Part 1](https://www.reddit.com/r/gonewildstories/comments/lgzc0n/24m_corrupted_by_29f_colleague/), [Part 2](https://www.reddit.com/r/gonewildstories/comments/lhjz8s/24m_corrupted_by_an_older_f_colleague_part_2/) and [Part 3](https://www.reddit.com/r/gonewildstories/comments/libmq0/24m_corrupted_by_female_colleague_29f_part_3/) are also available.

*”I’ve spent three weeks dreaming of that” she muttered as i slowly pulled my cock out of her cum filled shitter. “Now fuck off so I can sleep” as she rolled over and closed her eyes. I quickly got dressed and slipped out whilst my still warm cum slowly dripped out her arsehole.*

As mentioned previously, that afternoon/evening it was my high school friend Emma’s birthday. Emma and I had been very close friends since we were 13 and despite really fancying her during my hormone filled teens, nothing bar making out (which was like shaking hands when you were 15) had ever happened between us. I was well and truly friend zoned and was usually the guy to pick up the pieces over the years when guys had treated her like shit, and there had been many times where I had physically carried her home drunk and put her to bed so I was well liked by her family. I had actually her tits (and she did have a great rack – E/F cups) on numerous occasions and whilst i’d be lying if i said i hadn’t cracked one off to her, there was never any danger of our friendship developing into anything more. Read more »

My [M] first experience with a couple [MF] at 19. They were in their 40s. First swinging experience

About 6 years ago, when I was 19, in college, I first started to discover the world of “Swingers” and couples with open relationships. Back then craigslist was kind of the primary mechanism for ‘free’ posting and searching for like-minded individuals. Being a horny college guy with a high sex drive, I explored the casual encounters postings frequently. Some background, I am a tall (6 foot 5), big (8 in) and athletic guy who, come to find out, is often what a lot of couples are looking for (lucky me I guess!).

One day, a post caught my eye. An older couple (early to mid 40s) looking for a younger ‘stud’ to fuck the wife while the husband watches and eventually joins. The woman was smoking hot. A slender body, fake tits and a nice ass. Burnett. I sent a reply with some seductive pictures and little about myself, fully expecting this ‘couple’ to be a fat, creepy man. However, after the initial response and some chatting, the woman seemed legit and we exchanged numbers and verified we were both who we said we were. Read more »

The tale of tits-out Tammy [MF]

(I’m a dude btw, but this story isn’t about me…)

*Now listen up boys wherever you roam*

*And I’ll tell you bout the biggest slut I ever known*

*She had dirty blonde hair, puffy cocksuckin lips*

*A huge pair of melons and an ass twice as big*

*And everywhere she went she was slobbing on dicks*

*Cos Tits-Out Tammy was a fat fuckpig!*

Gather round fellas and grab your dicks because I’m about to tell you some true tales that have kept me pumping it for almost a decade. They concern a gal that was known as Tits-Out Tammy (or often just Titty for short) that moved into the house I was living in back in the day. Tammy hasn’t picked up her nickname at that point and was just a chick moving out of her boyfriend’s and looking for a room. Me and my pal Stevie were advertising one and in a slightly desperate position regarding rent (our friend had just moved in with his girl). We couldn’t get anyone in and didn’t want to scrape up the extra rent between us. Read more »

Lockdown Love, I Fucked My Daughter

“You should put some clothes on before you come down here, and stop walking around the house like you were still ten years old. You’re eighteen now Rachael, you should act like it.” I told her, the slightest sternness to my tone.

“But you liked it didn’t you daddy?” She said smiling, toying with me. “Didn’t you?” She said, now pulling at my cheek jokingly, trying to make me laugh.

She always liked to play games. It was impossible to admit that I liked what I’d seen. She was my daughter, how could I?
Being a dad is a pretty tough job, the stresses and strains of bringing up kids can be overwhelming and my teenager daughter had always been a handful. Going through high school it was clear to me that Rachael was an exceptionally clever kid and she would need a lot of money spent on her in the form of private tutors for all of her subjects. As early as ten or eleven her ability far outpaced everyone in her class and even her entire grade and I was rarely able to help her with her homework anymore. She had to change high schools twice before she hit eighteen because every time she went to a smarter one she would soon outpace everyone and eventually need another new high school. Read more »

Being naugh[t]y in my sister’s bedroom

This is another true story about one of the times when I was all dressed up as Josie. Sorry kinda long, but figured it would make the story better.

I was in the middle of moving to another city and had to stay with my parents for a couple of weeks until my new apartment was ready. I would stay with my parents for holidays and random occasions while in college and had not stayed there for that long since I was in high school. My old bedroom was turned into their new office and the only bed available was my sister’s who is two years younger than me. I spent many days in high school dressing up in her clothes, however had a decent collection of my own that happened to be with me since I was moving.

At that time i had a gf, but we were always off and on and my decision to move to a city six hours away did not help the matter. We were planning on seeing how things go once I got settled in. I recently started meeting people while dressed up,especially during my off times with my gf. She was one that got me back into dressing up since not dressing up in college until this point. Read more »

She was 27, I was 18. [M]y true story

In high school I basically live with my cousin and his gf. They lived in an apartment up the street from my school. They shared a hallway with their neighbors, a couple in their late twenties their names were Nick and Amber. We all became close friends and would often play cards, drink or smoke weed. Amber caught my attention right away, she was 5’5 with a mom bod, b cups and long blonde hair. She was flirty, outgoing and touchy sometimes. I was 6ft 185lbs, I played sports so I was fit, not buff but fit. I lost my virginity when I turned 17. I told my cousin and that loud mouth asshole told Nick and Amber, and that’s when I caught Amber’s attention. One night the nextdoor neighbors plus a friend came over for poker night. We gathered around the table and amber decided to sit next to me. We all were drinking and smoking having a good time and all of a sudden I felt Amber put her hand on my thigh. No one could see what she was doing, it was a tall table and the chairs were short enough to hide it. I thought Amber was being her normal touchy and flirty self trying to distract me. I gave Amber a minute to take her hand off my thigh and she didn’t. I tryed moving my leg but her hand stayed. I gave amber a look and Instead of looking back at me she just gave a flirty grin. She started to run her fingers up and down my thigh and each time her fingers would get closer to center. My heart was racing, I was getting excited and she could tell. That’s when rested her hand on my dick. Nick stood up and amber and I froze. Nick went to the fridge for another beer but we ran out, so my cousin, Nick and their friend decided to go get some more. It was just my cousin’s gf amber and me that stayed. I went in the kitchen for some water and my cousin’s girlfriend went into the bathroom. Amber watched as she left the room and followed me into kitchen. I turned around and the next thing I know were making out. Her hands behind my head and her leg wrapped around mine. She run one hand down my chest and slid into my pants, she had me but my cock. She started to slowly rub my dick. I grabbed her by her ass and her pace pace quickened, that’s when a the toilet flushed. Amber ran back to the table and I stayed in the kitchen. Shortly after everyone else had gotten back. After the poker game I had just laid down in bed when Amber texted me saying goodnight ;) followed by a topless picture of her, that’s when I found out she had her nipples pierced. I played with myself tell I sleep