Tag: High School

Daddy Dearest[F]

My name is Felicity, I am 18 years old and I have just become a woman. This is the story of that moment and of the realization of my most shameful and glorious fantasy.

When I hit puberty I never really was very interested in boys, I didn’t date, I didn’t even begin touching myself until i was 16. I just had no interest, i had seen sex scenes in movies, some friends in high school used to giggle while watching porn videos at sleep overs, i dont know, it never really seemed exciting to me. I tried, of course, i participated in the normal slumber party experimentation, but even as i had a cute 17 year old red head buried in my pussy, i just felt bored and underwhelmed by it all. The very first time i felt that sexual tingle was when, at 16, my father walked into the bathroom as i was showering. Something to note, i look very similar to my step mother. We are the same build and height, we both have fairly small, perky breasts and pale white skin. I have lighter and shorter blonde hair than she does, down past my shoulders, but when wet it looks a lot darker. At this moment i wonder, well, i secretly hope, that my father married her because she looks like me. Read more »

Daddy Dearest[mf][incest]

My name is Felicity, I am 18 years old and I have just become a woman. This is the story of that moment and of the realization of my most shameful and glorious fantasy.

When I hit puberty I never really was very interested in boys, I didn’t date, I didn’t even begin touching myself until i was 16. I just had no interest, i had seen sex scenes in movies, some friends in high school used to giggle while watching porn videos at sleep overs, i dont know, it never really seemed exciting to me. I tried, of course, i participated in the normal slumber party experimentation, but even as i had a cute 17 year old red head buried in my pussy, i just felt bored and underwhelmed by it all. The very first time i felt that sexual tingle was when, at 16, my father walked into the bathroom as i was showering. Something to note, i look very similar to my step mother. We are the same build and height, we both have fairly small, perky breasts and pale white skin. I have lighter and shorter blonde hair than she does, down past my shoulders, but when wet it looks a lot darker. At this moment i wonder, well, i secretly hope, that my father married her because she looks like me. Read more »

[MF] Becoming my Boss’s Slave part 2

It had been a few days since I had seen Alex Chain at work, so my life was back to normal. I was attending training sessions, learning more about the world of finance, and planning out my future career. I tried to pretend and tell myself that I didn’t care about him not calling me or showing up to see me, but it was obvious by how often I looked over toward the door during course sessions that I was only lying to myself.

Even if nothing else happened with Alex, I would have appreciated experiencing him. It was becoming clear that what I felt for him far surpassed lust. Actually, it felt as though I were falling for him, and hard.

After training that day, I was tired of arguing with myself about it and decided to try to find out where Alex was. I was walking out the door and turned to the receptionist, trying to appear as though I had just remembered to ask.

“Hey, I was wondering if you’ve seen Alex lately, I needed to ask him something about the material,” I said.
“He went to the Bahamas for the week,” she answered. “He tends to do that when he needs some time to go think over big business strategies.” Read more »

[MM] Cheating on my gf with my roommate

Originally posted about my experience in r/gaystoriesgonewild, someone suggested I should post here.

I was a freshman in college. I always thought I was straight. I was into girls, I fantasized about girls, I dated girls. Specifically, at the time, I was dating someone I knew from high school, call her Kate obviously a fake name). She was in the same friend group since freshman year, and we started dating junior year. We were both studios and were accepted to the same state university–not that surprising since state uni accepts ~40% instate students.

Anyways, first day of college, we drove with each of our families to uni, we unpacked, each had dinner with our family, and met up and explored the campus. Because we had come so early, I had not met my roommate yet. When I came back, it was night, and he had already unpacked his stuffs.

I was surprised when I first met him, let’s call him John. We couldn’t have been any more different. I was moderately tall (5’8) with blondish hair, and slender frame with a boyish look. He was maybe 6’3, with ragged brown hair and beard, with a muscular frame. I felt small in front of him. When we shook hands, I noticed how bigger, and rougher his hands were to my smooth hands. Read more »

Fun on the farm – [M]y [f]irst mutual masturbation

I was just a few weeks shy of 18, and it was literally my final official day of high school. Exams were over, teachers were cleaning out their classrooms, but I had to go one more time, to get my photo taken for a couple of scholarship applications. This was long before email, and I lived far out in the country, more than 20 miles from school, so it wasn’t easy. I got a lift from the school bus driver, who was dropping it off for summer maintenance, but after the photo session, I had to hitch a ride back home.

There I was, standing with my thumb out at the edge of town, at 11 am on the last day of June, and a very hot day it was already. To my surprise, the third car going by slammed on the brakes and pulled over, and I ran over to hop into a sporty-looking red Mustang – an unusual car for a rural area. Even more surprising, the drive was one of my classmates, a young woman named Patricia. It turned out she had also been getting her photo taken, and she was dressed up way beyond her regular blue jeans and patterned blouse. Today she was in a short pastel yellow dress, matching her hair. Patricia was a quiet, “big-boned” farm girl, one of those who did a lot of chores and had the legs and arms to prove it. I tried not to stare at those legs as I climbed in, but couldn’t help it. Read more »

[MF] Banging my friend on Christmas

This about a girl named Lily that I had great sexual relationship with.

I first met Lily in high school and didn’t actually get to know her very well until senior year when we had several classes together. Started getting a fondness for her due to the fact that we disliked a lot of the same things and people.

My fondness became more of a crush because she is a very hot chick. Huge ass, firm body and a great smile. I swear, she was shaped like a delicious pear.

We always flirted with each other, back and forth. Teasing with shoulder shrugs, leg strokes, arm squeezing and playful winks. But we never dated.

It was always awkward for us because we were never single at the same time. That didn’t stop her from being a huge tease, flaunting her ass at me during quiet moments alone. I’ll admit I’ve given a squeeze to that huge booty more than one occasion and she’s always someone who reciprocate a squeeze.

We had a falling out after highschool. I tried to have her break up with her then boyfriend because I wanted to be with her. Lily decided to stay with him and I didn’t take the news well. Read more »

[MF] An awkward encounter with my cousin

I know I missed the boat on all the cousin-fucking stories that blew through here a while back, but to be perfectly honest, my own story seems downright *quaint* when compared to a lot of the ones that have been posted, in that no actual sex occurs. Much like my last story, I suspect this one is unfappable, but maybe everyone will at least find it interesting.

Sorry to disappoint off the bat – I promise, the story does include a somewhat *sexy situation* or I wouldn’t post it here. I’d be lying if I said that I was 100% into it (this is my cousin, after all), but certainly the moment has ingrained itself in my mind as thoroughly confusing – one of those moments that regularly becomes buried in your subconscious, resurfacing at strange or inappropriate times, like when your grandmother gives you $20 on your birthday and you suddenly have to sit on the couch with a pillow in your lap. It wasn’t *you*, Grandma, it was my *cousin*.

Hmm, not better. Read more »

[MF] My first time

This is my first post so feedback will be appreciated. This is a true story to the best of my memory of how I lost my virginity.

First, let me start off by giving a bit of background about myself. I’m in my late 20s and was a virgin all the way up to last year. I grew up religious which meant that early in my life I was set on staying a virgin until marriage. I was popular and attractive in high school so I had plenty of girls to date but nothing ever happened more than kissing and some heavy petting (and one single blow-job but that’s a story for another time). While I was in college, my sexual views became more liberal and I started hooking up more but still held out and never actually had penetrative sex. Once I realized that sex really doesn’t mean a whole lot, I had gained a bit of weight and lost a lot of hair (DAMN YOU MALE PATTERN BALDNESS). I was ready to finally have sex but I couldn’t find anyone to have sex with! Until…

Enter Mel Read more »

[MF] Fulfilling high school fantasies with an old crush.

*Get comfy. This is a long one.*

—————-

So it’s been a while since I’ve posted, but it’s been a while since I’ve experienced anything worth posting. This story isn’t going to be as kinky as some of my other ones, but it’s been a wet dream of mine since high school, so I’d figure I’d share it anyway.

This starts back in junior year of high school when I met V. She and I shared a class together–I don’t even remember what class–and she slowly came into my friend group. I had a pretty big crush on her right away, but she fell for my best friend, and he and she dated for about a year, so I let my feelings go. By the time he and she broke up, I was dating another girl, so again, things never developed between V and I. But that doesn’t mean I didn’t think about her.

V was about 5’6″ with hazel brown eyes and curly black hair. And by curly black hair I mean **curly** black hair. Like, basically-a-fro curly hair. She was a little on the thick side with perky tits and a big ass. We always teased her that Apple Bottom Jeans were meant for her. Read more »

[MT] Cum swapping with my girlfriend in college.

Sorry this is a bit long…

Back in college, I was a nerdy computer science major, and roughly dressed the part – I wore graphic tees with excruciatingly pedantic designs, wore a mop of messy unkempt black hair, and walked around in flip flops until the weather made it unbearable. My only redeeming quality was that I was not terrible-looking, and I was in fantastic shape at that point – I wasn’t the most athletic guy, but I spent a lot of time at the gym. And so, I’d had girlfriends before, but as you might have expected, I was about as smooth as your typical computer science major and so aside from one awkward, messy night of sex, they never really went anywhere.

So when college hit, I felt this was my chance to come out of my shell, sleep with some girls, and explore (not unlike most nerdy college freshman). But I went to my first party, and, having not had any alcohol before, drank something like 1/6th of a handle of vodka and got absolutely black out drunk and woke up on the floor of the communal bathroom (not even of my own dorm). My friend later told me I’d stripped down to my boxers, began yelling something about love, I then proceeded to start biting things and flirting with random strangers. Read more »