High School Archives — Page 268 of 805 — NSFW story

[MF] I fucked my ex bf’s dad in a kohls… [27F]

So a couple months ago I flew home for a funeral. Stayed with my parents for a few nights. Ended up going to a kohl’s to grab a few things, and randomly ran into one of my Ex’s Dad. Hadn’t seen him in almost 7 years, but he instantly recognized me.

Made some small talk for a while, he couldn’t help but compliment over and over on how I looked, how I’ve grown, and how much he missed me being around the house.

He had always eye’d me back when I was dating Dan (his son), back in high school. He was a younger dad, in his late 30’s when I was dating Dan.

It was honestly great to see him, and he lost a ton of weight, seriously gotten into shape.

I had a few items in my hand, we talked for a bit, and I helped him pick out a few things for himself, then he helped me pick out a few things as well.

I couldn’t help but be a little flirty. Read more »

Haven’t had sex all year so my chad friend gifted me a night with two of his fuck buddies for my birthday [MFF]

I’ve read and wanked to many stories posted here, so with no one else to actually share this event with, why not tell you all about the best night of my life.

So I’m just an average looking dude with an average dick but I’ve been close friends with this gigachad since high school, and anytime over the course of our friendship (almost ten years now) when I’ve been in a dry streak with girls he’d occasionally go out with me to get me laid. But he’d never actually set me up with any of his regular “cum dumps” (as he calls them), except the one time with a girl we went to school together.

Now six months ago I broke up with my over a year-long ex and I haven’t had any sort of intimacy since then. So obviously I told him and just thought that maybe we’d hit the city for my 25th birthday, but said he had a better idea. Read more »

[MF] I couldn’t get a date in high school. I showed up to my 5-the year reunion with my gorgeous 10/10 girlfriend and blew everyone’s minds ?

Keeping it short here.

I was a big dork in high school—got teased, bullied, couldn’t even get a date for prom. In college I found myself, mellowed out, gained a lot of confidence and started having success with girls. By a pretty freak stroke of luck (we were paired up for a class project) I became friends with an absolutely stunning girl—tall, blonde, piercing sky-blue eyes and an incredible figure. She had a boyfriend at the time, but he wasn’t great for her and a few months later we hooked up over Spring Break. And then we started dating. That was two years ago. Now we live together.

So, five years after my high school graduation, we show up to my reunion. I’m in jeans and a t-shirt, she’s in a tight, short, metallic zip-up dress and heels (*DM for a pic). As we walk in, heads are turning, and I’m feeling everyone’s gaze on us. She squeezes my arm, I can tell she’s getting a huge kick out of it, and so did I. Once people realize who I am (I’ve got a much better haircut now), suddenly jocks who wouldn’t have given me the time of day five years earlier are acting like we’d been best friends, ex bullies are glaring at me from dark corners, and girls who’d turned me down are smiling and kissing me on the cheek. And even better, my girlfriend makes sure everyone knows I‘m hers—kissing me, holding my arm, whispering in my ear. It’s petty, but I‘m absolutely eating it up. Read more »

The Necklace [MF] [Age Difference]

“No, leave it on,” I insisted.

Shelly gave me a questioning look.

“A promise is a promise, Shelly,” I responded, sternly.

Shelly’s hands moved away from the heart necklace she said she had gotten from her college boyfriend — the one she’d promised she wouldn’t take off. It fell back to her chest, twinkling in the daylight, just above her pair of young, firm breasts. That necklace was all she had on.

“On the bed,” I continued. Obediently, if a little nervously, she moved to the white comforter and sat down. “No, turn around.” She flipped over and got on all fours, pointing her young, firm ass in my direction. Her pussy was glistening with slippery arousal.

“That’s better,” I encouraged, still not approaching her.

I admired the view for a moment before continuing. “Shelly, are you sure you want me to take you? If we do this, there’s no going back.”

She twisted her neck to face me. She was biting her lip, and it was all she could do not to touch herself. She nodded her head.

I still didn’t move.

Looking at me expectantly, impatiently, she finally let out a whimper. “Sam. Please.” Read more »

First time virginity taker [MF]

This story happened when I was 22, the summer immediately following my college graduation (4 years ago). I attended a pretty good school in Boston and, like many people in my stage of life, I was trying to figure out what to do next. I had a liberal arts degree that, while interesting, wasn’t the most practical in terms of finding a job. So, in the mean time, I had taken a temporary position in the public school system while I tried to figure my life out. I had an income, a nice apartment, and was enjoying bachelorhood. I had been in a semi-serious relationship over the last few months before graduating, but that had ended as school did so I was enjoying bachelorhood.

I had been using the usual gambit of dating apps to try and meet some new people (Tinder/Bumble, you know the deal). Anyone who has been in these situations knows that those apps can bring some amount of success, the occasional ONS or something along those lines. But it is far from a guarantee, as most conversations just die out over time.

[F]resh air and a su[M]mer breeze

All person’s depicted are 18+
NSFW starts at all CAPS marker.

“Good thinking” she whispered in my ear as I felt her hips thrust harder against my pelvis and begin to grind against me. My cock was hard but the extra motion felt good and I began to press back into her
.
.
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This took place between my second and third year at University. I had moved back home for the break, jobless and unable to stay in the city. I had been dumped a few months before and had only hooked up once or twice and was feeling fairly low.

When I got home, I was browsing facebook and started chatting with a girl named Erika I had gone to school with. I’d always thought she was cute and it turned out she was planning to move to my city the following school year.

I suggested we meet up, as I would be home all summer and could tell her the highlights of the city. Erika seemed quite excited by the idea and we quickly decided on a coffee shop to meet at. Read more »

[MF] The second time I [18f at the time] had sex [unknown age M]

I am currently a early-mid 30something woman. I’ve been having sex for about 15 years or so, and probably would have longer if I hadn’t been so awkward. Once I got over that initial hump of the “first time” needing to be special, I went wild. After years of reading here when I need a quick way to focus my attention and get off, I decided to share some stories myself (I realize this story isn’t as overtly sexual as other stories here, getting the hang of writing these and keeping them accurate). This particular story is about my second time.

The summer after graduating high school, I had the opportunity to go to Europe for two months. I spent one month at a program though my high school and then spent the second month touring with a friend who lived there. During this trip, I had sex for the first time, although it’s not something that is worthy of any story. It happened and that’s all that matters at this point. Read more »

Fucked by my high school crush [FM]

>DISCLAIMER: Long story. If you only want to read the sex part, please jump to Day #3, paragraph 3. Sorry, I know my stories are long. I promise I’ll try to write shorter ones next time.

I am so bored. This was supposed to be our first summer trip where I joined my older cousins and got to party with them out on the lake. Instead, I got stuck baby sitting my younger sisters and cousins. One of my older cousins did come, but he was more of an oddball. He never played with us growing up and had never come over to our holiday parties at grandma’s house. So the fact that I got stuck with him being the only person who I can relate to is just great. So far, my week-long camping trip was looking like it was going to be an awkward baby-sitting job with absolutely zero fun. Oh boy was I wrong.

Day #1 – Late Night Hike Read more »

Solving Problems I was Walking In To Pt 4 (FF)

Pt 4

I have to say I am getting more than a little nervous. Two days ago I fucked my wife, Amy, in front of a camera, with Lily and Sally as cameramen, or women, whatever, Sally having the backup role of fluffer. Today, I am filming, with Lily’s husband as a second cameraman, Amy and Lily fucking, a full on lesbian action scene. What the fuck am I doing?

Two nights ago, the evening after we did our scene, Amy confessed she was, for the first time ever, letting her inner slut go. I’ll say, she’s wearing me out, or rather, I better go and get some Viagra if this keeps up. Remembering the events of the day, she was again seriously wet and I better get in to make her cum. Fortunately, my tongue worked better than my dick then and a quick, thorough, tongue lashing was what she needed to get some sleep. During the night, I woke with her sucking on my dick, a pleasant experience at the worst of times, but right then, fucking brilliant. Better than ever, in fact. She learned a new technique the day before and was using it on me. Unbelievable, as I came deeply into her throat. In the morning, she told me that was for her, so sexy, so pleasing she could do that to me and looked forward to many more years of doing it. Read more »