High School Archives — Page 444 of 805 — NSFW story

[F]inally got with a guy I had a crush on since high school (15+ years ago)

I’d always had a crush on Tom in high school. He’s this tall (6’2″), handsome guy that was the all-American type (good student and athlete, totally respectable). I was more of a theater nerd but he and I were friendly- he was the kind of guy that was sort of friends with everyone. And the kind of guy every girl in class had a thing for.

Years went by- I got married, had kids, and divorced. He was engaged but it got broken off for reasons I don’t know. He has a pretty high profile job in our area while I head up a non-profit currently. And we found ourselves at a Christmas party last December hosted by a couple we were both friends with. We chatted and had some drinks. There was a little bit of physical contact and there’s no way he could not have known I was totally into him.

As the party was winding up, he and I left at the same time and he remarked that he wasn’t really tired yet and asked if I wanted to have a drink art his place. We both knew what that really meant and got into his car. Before he could start the engine, I leaned over the console and started kissing him. He kissed me right back for a bit and then broke it off so we could head to his apartment. Read more »

Guest comes to visit [Cheating] [MF] [Cuckold] [First time]

An old high school friend from where I (38F) grew up was visiting my town and posted on Facebook that he needed a place to stay for a few nights after his conference each day.

I hadn’t seen him in 20 years but I told him that we had an extra bedroom and he could stay with my husband and I since we happened to live near the conference center in town. He agreed and went to his conference for the first day and then showed up after dinner at our house.

When he showed up, I was surprised because he looked so different from when we grew up. He was kind of a dork and not really out of shape but definitely not in shape in high school, but now he was pretty good looking and he had gotten really fit.

We caught up for a bit and it was pretty late so we showed him to the guest room. In the middle of the night, my husband was snoring so I got up, and forgetting we had a guest, sorta sleep walked down the hall. I went to the guestroom (that is where I usually relocate in the middle of the night), pulled the covers back to get in bed and about had a heart attack as I realize/remembered my high school friend was sleeping in there! Read more »

My GF and Her Friend [MFF]

My girlfriend, Jess, had a best friend from high school, Elise, that hung out with us pretty often. Jess and I lived together in a nice enough apartment in an American city and Elise lived about 30 minutes away just outside of the city limits. Often on weekends she would come over to our apartment and we would go out into the city and have a fun night out on the town. Jess and I would serve as her wingmen helping her pick up various boys around the city. One time we even let her use our bed while she hooked up with a complete stranger. I wouldn’t classify Elise as a slut but she was definitely more outgoing than most and I enjoyed our adventures together.

Elise had an incredible body and a cute face. Slim and taller than most girls, she had a cute plump butt that was a product of the yoga classes she went to consistently, and perky B cup boobs. Jess was a head shorter than Elise, slightly wider and had larger C cup boobs. Both girls were attractive and definitely attracted attention whenever they walked into a club or party together. I’ve never seen Elise naked but I’ve seen her in her underwear and bikini enough times to know how much I was attracted to her body. Read more »

[M]y [F]irst story, losing virginity, 18+

Hi. So I’m attempting to write an entire timeline of all of my sexual partners. I know it’s an undertaking, so bare with me. I’m doing everything I can to remember everything in order and accurately without embellishing. Some stories may be boring! I am 6’0, always have been skinny, now athletic, dark hair, white but darker skinned, and horny.

This is the first story of my first girlfriend in high school (18+)

Oh the joys of being in high school. I was never a prude but I think the catholic middle school and private elementary school threw just a tad too much out there on the scary abstinence education, so I was hesitant, and probably a tad socially awkward, but who wasn’t? I had a few girlfriends in high school, but the one who was my first was my senior year. Luckily, my birthday was at a time where I was 18 almost the entire year. We were both 18+ for the duration of our escapades

She was guatemalan, 5’8, fair skinned, pert ass, b cups, great teeth. Sofia. Not curvy but proportionate. Read more »

She [F] came up to me [M] after closing and said she likes tall guys.

She(f) cam up to me(m) right after closing time and said she liked tall guys.

This was 2 years ago when I was 27. I went to a bar on a Thursday night with my friend. I’d never been to that bar before but it was clearly the city’s best Thursday night spot because I was packed.

After plenty of drinks and flirt, closing time hits and the mad scramble for ubers starts. My friend got his first, not one minute later a girl who introduced her self as Mary walked right up to me and said she had been eying me all night because she likes tall guys.

For reference I’m 6’6, athletic build with a beard. I would describe Mary as the cute band girl from high school. 5’5, blond hair, with a good body. They way she looked at me I could tell she really wanted me and that was turning me on.

I asked if she wanted to share and Uber and she agreed and put her address in the app. I learned it was her 25th birthday, she was there with her friends and to my surprise they didn’t try and stop us leaving together. Read more »

Sex with my high school girlfriend [F]

My girlfriend came over to the US very recently from Vietnam. In my school, I was the only one that could fluently speak Vietnamese so I had to translate everything to her. We would talk together at lunch and sit together in our classes and soon enough, we started dating. My parents now allow me to go to her house every Monday to help her with the online learning since she doesn’t understand it. Today when I was there, she accidentally stumbled backwards while trying to grab a book and ended up sitting in my lap. I was trying really hard to hide my boner, but she ended up seeing it anyways. When she noticed, she gave me the cutest smile ever (God I will never forget that look) and told me not to worry. Two hours later, I helped her finish the work she had for the rest of the week. When her mom went out to go grocery shopping, my gf decided to take a shower. I was trying to be respectful and not look at her while she was undressing, but I ended up taking a peek anyways. To be honest, I don’t consider her body sexually attractive so I guess I was just nervous. She noticed it again and asked if she could see it. As I was blushing, she came over and proceeded to bite my neck. A couple of minutes later, she took off my pants and started to stroke my cock. Later, she started sucking and moaning at the same time and about 20 minutes later, I came. Her face was then covered with cum and after that I hugged her goodbye and left. I’m going to her house again next week and I honestly hope that we do it frequently.

Not proud, fucked my married step sister [mf]

So, I have shared a bunch of my personal sex stories, but due to the content, this was one required a throwaway screenname. What is interesting for me is that I now see that most of the things that spark me the most sexually began on this day: Panty/ass/pussy sniffing, pregnancy risk, being dominant, fucking married women, cheating, risky sex (where you could get caught easily). And this all happened with my step sister in the course of one day. This is really difficult for me to write because it is the sexual experience I am most ashamed of, but to this day the most intense sexual experience of my life. Read more »

That time I let a stranger eat me out in a park [FM]

Skip to ———— for the good stuff.

I (29/f) had been chatting with this dude (37/m), ghosted him off and on for a month when I took a huge risk and had my pussy eaten in a public park at midnight the Friday before our town started shutting down non essential businesses. I had just been ordered to work from home, had made the decision to not see my family and had been drinking to deal with the complicated feelings this is bringing out in all of us.

So, fast forward to me getting back on hinge at around 10pm , tipsy after a whole bottle of Shiraz with my neighbor. I’m swiping and this incredibly persistent man messages me again. Feeling frisky and joking about having to meet up in a park for date for the foreseeable future. Then we start talking about fantasy, one of his was walking in on a strange woman who’s masturbating, eating her out and then leaving. I am just tipsy enough to be WILDLY intrigued and we start talking dirty. Read more »