High School Archives — Page 702 of 805 — NSFW story

[MFF] Max and her sister

Mallitzfest – that was what my dad and Max’s dad called our annual get together. It was a mix of our family names. They were the Malloys, Irish as you like, red hair, freckles, big personalities. We were the Spitzes, German to the core, serious, precise, well-ironed. There was a lot of beer and a lot of sausages.

Max and I had been good friends when we were little. Same elementary school, same high school, but we had gone our own ways to college. I hadn’t been to a Mallitzfest for a couple of years. Max and her sister had grown up. Max was slender with her hair straitened and cut into a short bob. Her sister, Mary, was a year or two younger, a carbon copy of her big sister but a little curvier and with a mane of long flame curls.

‘Hi Joe,’ said Max. She was carrying a couple of boxes of beers towards a huge tub of iced water. Her sister, unloading another box into the bucket, blushed furiously and said nothing. ‘You going to stand there like a potato or are you going to help?’ Read more »

The night I was used for revenge [MF] [cheating]

It was the summer between high school and college when I started dating Lydia. I use “dating” in the loosest sense because while we talked quite a bit and actually went out on several dates we were never official by any stretch of the imagination. We made out but that was basically it physically for us.

Lydia had a cousin named Tiffany who was usually at Lydia’s house. She had a crappy home life so I understood why she was there. Tiffany and I were friendly. She was a cute girl with black hair, deep brown eyes, freckles, b-cup and perky breasts, and thick muscular thighs. She had been a cheerleader in high school so she was pretty fit. She wasn’t a knockout but she was attractive.

We were all hanging out at Lydia’s house one night and had watched a movie. After the movie I was heading home. There were no frills when I left, not even a kiss from Lydia or an offer to walk me to my car. I didn’t need her to it just seems like the polite thing to do when you’re “dating” someone. As I’m walking out the door Tiffany comes out behind me. She says she’s going to have a smoke and we walk to my car and start chatting. Nothing extensive just talked about the movie and joked around. I’m leaning with my back against my car when Tiffany asks me how serious I am about Lydia. Knowing it’s her cousin I’m careful with my reply. Read more »

My [F]irst Experience, Part Four

For those of you only joining now (though I can’t imagine why *anyone* would start by reading a story which is titled “Part Four”, unless of course it is a tale which starts *in medias res*, like *The Odyssey* or *Star Wars*) these are the continuing adventures of my not-quite deflowering by my first boyfriend, Gordon. By the end of my relationship with Gordon I was still a virgin, although we did everything but. So this has been the story of everything but! (But not “everything butt”: that was several boyfriends later!)

Previous episodes ([Part One](https://www.reddit.com/r/gonewildstories/comments/643txs/my_first_experience/), [Part Two](https://www.reddit.com/r/gonewildstories/comments/65kugl/my_first_experience_part_two/) and [Part Three](https://www.reddit.com/r/gonewildstories/comments/66x4jb/my_first_experience_part_three/)) have established that we – I – had in some ways become adventurous, but within a narrow set of strictures. I’d say that we had only scratched the surface, but it was more a question of him *rubbing* against my surfaces to our mutual enjoyment, but only to his actual climax.

Then came the day that we widened our horizons. Read more »

My Summer with Mrs. C [MF]

Back when I was in high school and college, I was a lifeguard at a local swim club during my summers. I would teach private swim lessons when I was off duty in order to make some extra money. My clients ranged from little kids who didn’t have time for the Red Cross sponsored lessons to adults who never learned how to swim and an occasional kid or two who’s alpha parents wanted them to “be more competitive” on the swim team.

After my sophomore year in college , I was teaching a brother and sister back to back once or twice a week. Their father wanted them to be great swimmers, so I worked them out and refined their strokes as their mom (Mrs. C) sat on a lounge chair and read a magazine and chatted with the other moms. Mrs. C was in her early 30’s and in incredible shape. She definitely ranked in the top 3 hottest MILFs at the club by the staff including the females. Read more »

Becoming His Daughter, [crossdressing, Mm, Older/young]

Note: I wrote this a couple weeks ago, looking for input before I write another.

How I became a Crossdressing Sissy Slut –
When I was 16, the summer before my Senior year in High School; I use to chat and cyber with men and women from around the US. I use roleplay/catfish as a teenage girl, most of the time if they asked, I would tell them the truth. I found a guy that lived near me and he convinced me to meet him. He knew I was a boy and enjoyed being a girl.

We talked about what we could do together. We concluded that I could probably fit in his daughter’s clothes, who’s a year older and just graduated. She was out of the house a lot and he found himself alone on his days off while his wife worked.

The day came and I showed up at his house. He was super nice and offered me a alcoholic drink that I took him up on, to calm the nerves. We both were nervous, neither of us had done this before. He showed me his daughter’s room and he had laid out an outfit he would like me to wear. Short while skirt with a lacy tank top. Matching bra and panties of course. Read more »

[MF] Fwb at work, cheating

It all started when a co-worker I had never met before scheduled a meeting with me and another IT guy I work with, stating that she needed help with an issue she has encountered. She hadn’t spent much time in our IT area, so I led us all to a smaller conference room kind of out of the way. As it turned out, we only needed the other IT guy for a little while, as the problem she encountered dealt more with the software that I manage/maintain.

Anyway, the meeting stretches out pretty long, and we eventually made our way to my desk to go over data since I didn’t bring my laptop to the meeting. Over the course of 3 hours I learn that she is kinda new to the company, and is currently only a temp worker. Despite this, she seemed to have a very solid understanding of some complex business processes, and I was quite impressed with how much she had learned. Read more »

[MF] I (M) won a bet with a friend of a friend.

This happened about 15 years ago when we were in our early 20s. My senior year of high school I moved to a new school and connected with a girl in my graphic arts class due to a shared interest in ska/swing music. She was my only friend that year even though I was cool with lots of people. She’s white with short brown hair and bangs, skinny, killer ass and cute as a fucking button. We hooked up once and realized that relationship wasn’t going to happen and we were better friends. We graduate, I moved away and lose contact for a couple years then reconnect later.

She invites me over to her friend’s apartment that I met a few times from high school. I think she went to another school. Really hot and a budding professional singer/guitarist. (She never made it big, but has plenty of live performances on YT… I would love to link but I couldn’t blast her out like that) Read more »