High School Archives — Page 317 of 805 — NSFW story

[M]y [F]riend introduces me to porn

(Disclaimer: I originally posted this story here six months ago under a different account that I ended up deleting. I am reposting it now for posterity. Enjoy!)

After high school, I had a friend named Madeline. We weren’t especially close, but we had several mutual friends and occasionally hung out. There was never any sexual energy between us.

Madeline was a very attractive skater girl, about 5″4″ish with shoulder length brown hair, piercing green eyes, and a fairly athletic build. I was a lanky metal kid, 5″11″ with chest length black hair. At the time we were both 18.

I was living in my parent’s basement at the time, saving up money to move out. One Friday night, I was hanging out at home, fucking around online when I got a text from Maddie wondering what I was up to. We texted back and forth for a while, remarking on how bored we both were on a weekend night. I let her know that I had several Crown Royal airplane bottles that I had stolen from someplace if she wanted to come over and kick it.

“Hell yeah!” She responded. “Let’s do it.” Read more »

I am a single mommy and i just fucked in a car [FM]

My ex recently broke things off with this girl he was seeing so we got to reconnect.

We went to the gym first, then to dinner, and then since we’re both living at home we parked somewhere and hopped in the back seat. It felt like sneaking around in high school again to be honest. Kind of hot and naughty.

I sucked his dick for a while. I loved hearing him tell me I was a good girl while I choked on his dick.

He asked me to slow down because it was “too good”. He fingered me for a while as well and told me he loved how wet I was. He licked his fingers when he was done.

I climbed on top of him and he entered me for the first time in over a year. And holy shit it felt good. He was bigger than I remember and really stretched me.

And it was the first time I’d had sex since the end of August (other than the virginity I took on Saturday and he wasn’t as well endowed and this guy). Read more »

That one time in the school bathroom… [F/M]

In high school, one of my many crushes was a tall, light-skinned mixed boy with dark hair and dark eyes named Christian. He was the second boy I ever had sex with and his cock was intoxicating. I liked his bad-boy personality and the secrecy of our, whatever this was.

We were walking around the neighborhood the summer after graduation, when I got an idea, “Let’s see if the school’s open”

He smiled and we picked up our pace toward our high school. We walked around the entire school, trying every door but they were all locked.

“Maybe no one’s in the front, we might as well try” Christian said.

Good thing he said something; it was open. It looked like there was a basketball event happening in the gym. We ran upstairs to the third floor before anyone could spot us and he led me into the boys’ restroom. I could feel myself get wet with excitement.

I pulled him into the biggest stall, not bothering to lock the door. I got onto my knees, undid his jeans and tried to swallow his entire hard cock at once. Of course, I gagged; his dick was too big for my very sensitive gag reflex back then. But I’m pretty sure I sucked it like a champ because I remember him grunting and pulling himself out of my mouth. Read more »

I [M] fucked my new hair stylist [F] at her apartment

I [33m] had a longtime barber who recently retired, so I have been going to this new girl [36f] at a national chain haircut establishment. Going from an old guy barber who has been in the game for many years to a younger, attractive female was initially quite different. The first time, Jade and I were quiet as I was just letting her do her thing while I sat patiently. However, the last two or three times we have really opened up and chatted about things and got to know each other.

She’s a single mother and comes from a very Italian family. She’s a little shorter than me at 5’6″ and has that Italian olive skin tone with deep, alluring eyes. She has a curvy body, without being overweight and very large breasts that I can’t help but want to push up against as she’s cutting my hair. She also has one of the coolest, laid back attitudes in a woman that I have ever met. Read more »

[MF] I got to fucked my best friend and lose my virginity soon after she broke up with her boyfriend

I like some backstory and I know quite a few other people do too, so I’m going to give context and lead up in this story. Those who don’t want to read that, skip to (. )( .) for the action. [Also just so it is clear, we were both 18 by the time of this story].

So the girl in this story, let’s call her Amelia, I met the beginning of our Junior year of high school. We bonded very quickly and soon became best friends. Even from an early point in our friendship, we were pretty open about things with one another. We learned quickly about our interests, wants, and desires.

Now Amelia is a cute Filipina girl, round face, big boobs and a nice ass. These boobs of hers are the type that were visible even when she wears a sweatshirt. To say the least, they are fairly big. She is also a short girl, shorter than me and I’m 5’5 (I’m sure she is like 4’10). Because of that, her big boobs look even bigger on her. One of the hottest things I found about her, besides her boobs, was the way she did her hair. I’m sure there’s a name for the style but I don’t know, so I’ll just have to describe it. Amelia likes to have it where most of it is kept up in the back but she lets two short strands drape down on the sides of her forehead(I guess like two bangs). I’ve always thought that was really hot. Read more »

Fucking my Stalker [FM]

Here’s another story from my catalog of awkward sexual experiences. Everyone is 18+.

I used to go to college with this girl, Sadie. For some reason she was *really* into me and even stalked me for a little while. I’ve never had a girl fawn over me before and especially not like this. I can’t lie, part of me felt like it was a nice change to feel chased as opposed to being the one on the hunt, but nothing went how either of us had planned.

Sadie was very short and petite, come to think of it, she may have been the smallest girl I’ve ever hooked up with. She had medium length, wavy blonde hair that she usually kept it up in a ponytail or bun and she touted big blue eyes with reasonable ass and tits for her body size.

I definitely found Sadie attractive, but I somehow had just talked my way into a date with Jen, who was super hot, funny and well out of my league. Our date had got me really nervous and I didn’t want to do anything that might mess up my chances with her. Read more »

[MF] – Unexpected Oral Creampie with my former bestfriend in a movie theater.

Okay a little short background story. It was back in high school many years ago, I was 18. Still a virgin at that time and have many gal friends and I admit I have fantasized most of them through their facebook and instagram bikini pics. One of them is my former best friend and lets call her Gee, she’s 19 and we were very close but not sexually or flirty but in a best friend type of way. She’s not too petite and not too chubby either but a good balance of both.

Anyways, few days before the movie theater, my friends along with me and Gee had a sleepover for a few days. It happened during the holidays so there was no school at that time so we had our own christmas party planned in some rich friends’ house. Nothing interesting really happened much. We were all too innocent to be doing NSFW stuff so we did the usual movies, chips, games and stories type of fun. Read more »

Danni F20s and her BFF’s Dad M50’s

Danielle was the middle child, 2 sisters and a brother. Her youngest sister they all knew was a half sister. The 2 oldest kids? Who knows? Yeah mom got around in her younger years, even after she married the eldest 3 childrens dad. Then one day he just up and disappeared, never to be seen by the family again.

Mom raised the 4 kids the best she could as a single mom. Yes she took suitors, but they never lasted more than I few years, if that. As the kids got older the 2 eldest looked more and more like they’re old man(the one who vanished), bigger build than the other 2.
The youngest never really resembled the others except her mom’s blonde hair. Danielle long brunette hair, slim build, long legs, and a blossoming young lady.

After her oldest siblings had graduated and moved out. Dannielle in high school, a few years left till she can graduate and go off to college. Another thing that would be a first for her family, her siblings, her mom, her aunt’s and uncles had never went farther than graduating high school. Read more »