Tag: High School

[mff] What I learned about myself in a hotel room with 4 coeds.

This story takes place years ago. I was a sophomore in college(art student). I had always been shy, and was never very comfortable talking to women. Lucky for me, my senior year of high school, a very insistent girl asked to my girl friend and we dated until shortly before this story begins. I was newly single at that time, so on top of being shy, I had no recent practice flirting with women.

To make up for my lack of social comfort, I got a little weird. I had embraced thrift stores(velvet sport coats, torn jeans, etc.), and had shoulder length dread locks(I’m white). At odds with my fashion, I was also pretty athletic. I road a vintage road bike (which wasn’t really hip at the time) everywhere, instead of driving, I rode 40+miles per day. That and I climbed a lot at a pretty high level.

So I’m trying to say, I looked like a hippy art kid, but I was a pretty ripped little guy, and I had fairly low self esteem.

One of the art clubs I was in organized a trip to NYC for 3 days so we could visit galleries. The story begins as about 10 of us art kids jet off to the big city. Read more »

[MF] Thinking with the small head

When I was a college sophomore many years ago, it was a period of time when the Pill was widely available and STDs were rare, at least among my peers at college. I’d lost my virginity as a freshman to Leann, a longtime girlfriend I’d had in high school. She was a year behind me and attended a different high school. We’d done most everything except PIV intercourse when I was a senior and she a junior, our reluctance stemming from an fear of pregnancy. Early in my freshman year she phoned to tell me that her mother had taken her to a doctor to get a prescription for the Pill – to “regulate her period” was the rationale, perhaps just for Leann’s father’s benefit, as her mother probably noticed our increasing physical intimacy and wanted to ensure that “regulate” meant “keep occuring.”

Leann and I fucked several times during that school year. She visited me a few times and spent the night in my dorm room, and I’d occasionally go home for the weekend and we’d find a private place for a quickie. Things continued through that summer, but our time together came to an amicable end when she enrolled at a college 1000 miles away. I could go into more details about Leann, but my story now is about what happened next. Read more »

Making the Good Little Christian Girl Mine [MF]

My name is Andy. I grew up in a very religious household, so I was kind of a late bloomer. It took me until college to have my first kiss, and I didn’t lose my virginity until I was twenty-one. But since then I’ve been doing my best to catch up. This is the story of the second woman I ever slept with.

In college, I was a member of a Christian outreach group for high school students called Young Life. I’m sure that plenty of people are aware of it, but essentially it’s a weekly club event where high schoolers come and play games, watch skits, sing songs, and hear a brief message about Jesus from one of the college-aged leaders. It was always a lot of fun and while I don’t currently consider myself a Christian, it was a big part of my college life.

There was this high school girl that attended every club, as well as our weekly bible studies. Her name was Rosie, and she had the greatest pair of tits I have ever seen. To this day they’re still my favorite. But she was in high school and I was in college, and there was a very strict policy against doing anything romantic with the Young Life attendees. So, like any good Christian I did the right thing and masturbated to thoughts of her constantly. Read more »

October Night [Mast, F]

Jessica sat on the front porch swing and listened to the sounds of the night air. It was early October and there was a bit of a crispness in the air. The blanket she was laying under kept her warm enough. Below the covers she was only wearing a pair of boxers (the ones she adored of her husband’s) and a thin t-shirt. She liked coming out to the porch on nights like this to relax. Her husband was off somewhere across the country on a business trip and she missed him so.

The cool night air was kicking up a bit more than it had earlier and a slight draft was coming in under the covers. Her nipples began to stiffen and she felt a familiar urge begin to take over her body. Many were the nights like this that she would begin to think about John and start playing with herself. John was the handsome young guy that lived down the road a bit. He was muscular and tanned from working in the fields all day. He would occasionally drop by the house when a package would be left by a fill in mail carrier that always seemed to get the addresses to their houses mixed up. Read more »

My time in Malia [NSFW][group]

This is my first story and first post on Reddit. It is completely true. Please let me know what you think.

I had just turned 18 and left high school. For most Scottish and British teens it’s almost tradition for you to go to one of the party destinations. We decided to go to Malia. I was deeply in love with my girlfriend at the time and went in a group of around 20 people. Clara (my girlfriend) and I shared a room with her best friend (Laura) and her boyfriend (Mark). Previously we have toyed a little with them but nothing serious, just a couple of dares and topless nights. I had fallen in love with the idea of sharing and wanted to do it again. Read more »

[FM] Food for Thought or Something Like That [kink]

Tldr; It’s an odd kink but sometimes you luck out. One day you’re just craving for raspberries and whipped cream the next thing you know you’re being pinned against your kitchen’s counter top and being fucked.

Let’s just say he got home before me – texted if I wanted anything to eat beyond dessert to which I replied: I want whipped cream and raspberries! TYVM! YW~ ;P :*:*:*:* And of course he would comply being the nice man that he is and knowing that I’m mostly stressed with day.

Upon arriving home, I took off my shoes and went about depositing the rest of my stuff on the couch. I greeted the cat – who often ignores me anyway – and went straight to the kitchen to find him with the stand mixer, a gallon of heavy whipping cream, and fruit. The place reeked of pot roast and hints of vanilla and lemon here and there. Read more »

[MF] Met a young girl online and flew her across the world to meet me

I’ve lurked on Gonewild Stories for a few years now, but never thought much about writing a story about myself before a few weeks ago, when I had one of the more interesting/unusual sexual experiences of my life. I’ve decided to write it down mostly for myself (as a journalistic writing exercise and as a way to hold onto the original memory and all of the specific sensations I felt and thoughts I had at the time).

I tend to get far more enjoyment out of stories that feel true and authentic; I suspect that many here feel the same way. With that in mind, here is my disclaimer: the story that follows is true, and my goal is to summarize the events with the utmost accuracy, even when those events do not reflect optimally on me or create the ideal pace, tone, whatever. It all happened, exactly as I will recount it. Read more »

[MF] Mistress Fail

Disclaimer: I’m married and this story contains extramarital sex. If you’re going to PM me about what an asshole I am then, please, go big or don’t write.

I met her on Tinder. She’s an extremely attractive woman with a public persona. At first I thought it was a fake profile but I soon verified she was who she said she was. We chatted. She found me attractive. We chatted some more. She was curious about having a married FWB. Too busy for a real relationship she said. We decided to meet for a drink.

Over a beer we really hit it off. She was definitely my type – natural beauty, hyper intelligent, open sexually. She was a bit awkward in an endearing way. An hour flew by. I had to go.

We chatted here and there. One Friday night we planned to get together again.
“What do you want to do?” I asked.
“I want you to fuck me.” Read more »

[MF] I [25M] hate-fucked a Trump supporter friend [24F] on the night of the election

This summer I moved to a new town for work. It’s a decent-sized Midwestern city, the kind of place with a small but active nightlife, a few colleges, etc., but nothing crazy. I didn’t know anyone here, but for the first couple of weeks that didn’t bother me, because I was focused on making a good impression at work, especially considering the way I fucked up my previous job. (It was a complete & unmitigated disaster. Long story, though, and beside the point.)

One day I was in the office building’s cafeteria, standing in line for another dilapidated burger and mound of soggy fries, when someone shoved their fingers *hard* into each side of my abdomen, right below my ribs. I’m a fairly fit guy, but definitely on the skinny side, so I don’t have much padding there, and it was extremely uncomfortable. I leapt instinctively away and collided with an old lady, sending her tray flying. In total fight-or-flight mode, I spun around, bringing my fists up, only to see Ashley grinning back at me.

“Still ticklish, I see,” she said. Read more »

[MFF] A very organized threesome

I’ve been back and forth on posting some stories here, so I figured I’d finally take the dive and share by far my favorite experience. This happened several years back with two friends of mine. I have a solid amount of back story, if you want to skip to the good stuff scroll on down to where I put GOOD STUFF.

Back when I was in high school I went on a date with a freshman (I was a senior) named Jennifer. Jennifer is half Puerto-Rican, she had think lips, about 5’3, tight cute butt and nice perky B cups. We went out on the one date and made out at a movie (classic high school). As I went through my college year we maintained a friendship. One time when we were smoking she disclosed she was bi-sexual. Our conversation turned sexual and I eventually said “well hey, if you ever find a girl to do a threesome I’d be totally down” and she laughed in response and said “sure you got it!” I logged that exchanged into my vault. Read more »