High School Archives — Page 560 of 805 — NSFW story

Amazing miniature college orgy over fall break with Kylie. [Group]

(Long, but totally worth it!)

In my first two years of college, my roommate Jay and I both would both have sex with our friend with benefits, Kylie. Regularly, almost weekly, we would have a threesome with her. In fact, I lost my virginity to Kylie when we first did the deed. Though it sounds crazy, I could have not have first had sex in a better environment, as Jay is one of my best friends. My nerves were calmed in a very supportive environment. They both kind of guided me through it, every step of the way. It was incredibly hot to basically take turns with her and communicate with her on such an intimate level. In hindsight, it was fairly reckless to not wear condoms, but she was on very good birth control (an insert in her arm) and we were very upfront with our sexual history. During all of our erotic activities with her, we never used condoms and it really upped the pleasure level. Anyway, because of this, we made an agreement to be exclusive sexual partners with only her. This only changed a few times, when we brought more people we trusted into the mix. Read more »

[MF] Because I Changed My Mind

TL;DR A pushing 60 year old widower tells you about a recent event where he slept with a long-time female friend of his.

Disclaimer: If bareback i.e. “raw” sexual tales bother you then stop reading now. If drunkenness bothers you then stop reading now. It MIT bothers you then stop reading now.

I’d had a series of very shitty relationships, and make no mistake: a huge part of the years of epic failures was on me. Heck I even slept with an ex while she’d been married to someone, the father of their multiple children. Until I met my late wife I was a man who was kind of in the middle of the ocean on a deflating life raft.

Princess loses her virginity [MF]

I had dated Princess for a little over three years, starting a bit after high school. She was a stereotypical country girl, blonde hair, brown eyes, DDs and a Kardashianesque set of ass and hips.

As I had mentioned in previous stories, she had given me head every single day we were together. It didn’t matter where or when, if I took my dick out then she knew what I wanted and would perform without a word need to be said. Several times in a crowded theater, or most often while I was driving. The most memorable time was in her living room while her mom was working on the computer, and all she would have to do was turn her head to see her daughter performing an ungodly act.

After about six months of dating, she told me that she wanted to finally have sex. Since we were both living at home, we decided to go to a motel to do the deed. She said there was no need for condoms since she took birth control to regulate her hormones. Read more »

[M] [F] [F] – A painful wake up spanking

One time after a long night of drinking during my college years with my high school friends (both men and women) we all passed out drunk. I’m an early riser, as were my two friends, both of whom are women. We were still drunk, and were fucking around, talking loudly, enjoying being still drunk so early in the morning…when one of the woman I was up with, Emma had the bright idea to wake up her friend Lizzy, who was face down passed out on the floor of a room underneath a table with a mountain of empty and partially full beer cans on it, with a very hard spanking because she thought it would be funny.

Emma found a large, metal yard stick in the garage and went up over Lizzy’s passed out body and as I and my other friend watched, Emma brought the yard stick high up above her head and down on Lizzy’s ass. It made a *CRACK* as it hit Lizzy’s unsuspecting bottom, which immediately woke up Lizzy with a scream of “OWWW!” but Emma was quick and struck her ass with the yard stick again. **CRACK** right on Lizzy’s ass again. She screamed and said “What the fuck Emma! That fucking hurt!” and got up and ran away, pissed off. We all laughed. Plus I was sorta turned on with this girl on girl spanking. Ohhh college.

Amazing miniature college orgy over fall break. [Group]

(Long, but worth it, I swear!)

In my first two years of college, my roommate Jay and I both would both have sex with our friend with benefits, Kylie. Regularly, almost weekly, we would have a threesome with her. In fact, I lost my virginity to Kylie when we first did the deed. Though it sounds crazy, I could have not have first had sex in a better environment, as Jay is one of my best friends. My nerves were calmed in a very supportive environment. They both kind of guided me through it, every step of the way. It was incredibly hot to basically take turns with her and communicate with her on such an intimate level. In hindsight, it was fairly reckless to not wear condoms, but she was on very good birth control (an insert in her arm) and we were very upfront with our sexual history. During all of our erotic activities with her, we never used condoms and it really upped the pleasure level. Anyway, because of this, we made an agreement to be exclusive sexual partners with only her. This only changed a few times, when we brought more people we trusted into the mix. Read more »

[True Story][M4F] A fantasy 8 years in the making! (part 1)

This is a fun story I wanted to share. This story is 100% true although I want to admit this story did not happen recently. I just had some fun on dirty pen pals today and was reminded of this story and found this subreddit so I wanted to share.

A long time ago I was in high school. I played soccer my entire life and even did some football. I wasn’t a nerd, but I definitely cared about my grades a bit (nowhere near top of my class, but took some honors classes and did fine). However, I was definitely a ‘good’ kid. I didn’t smoke, I didn’t drink alcohol, I didn’t have sex. This isn’t because I was some sort of narc or thought I was better than anyone, I just was too scared (lol) to even risk doing it. I would go to the occasional HS party and just hang out completely sober lol. Sure, I missed out on some good times but whatever. I had a high school sweetheart for a time, but all we did was kiss. Got the picture of who I was? Ok good. Read more »

Hacker Blackmail [MF] [Bribed] [LONG]

I was around 12 when I got into computers, at 15 I started using them for hacking, then, at the age of 19 I started to get into some darker stuff, hacking for my own personal evil.

It was a Saturday night in the hot floridian sun, maybe 9:00 pm, I remember the whine of the box fan I had resting on my window as it did nothing but circulate the thick, humid air.

I decided that tonight would be another night that I could exploit some poor woman.

I fired up my laptop and clicked on the icon on my screen, a piece of software I had worked on with some friends around a year ago, though I had modified it to my liking.

After everything had started, my trap was in place, a worm that was linked with one of those “you won’t last 5 minutes” games that you see on pornhub, at the click of the games ad, something downloaded in the background, I could then take full control of someone’s computer, see all of their personal information and most importantly, see their webcam.

I flicked through what seemed like hundreds of people… Read more »

[MF][Cheating]Slept with high school sweetheart years after we split up.

This happened many, many years ago. AOL instant messenger was all the rage, to give you an idea. I’d say this was about 1998-1999, give or take. Keep in mind that I’m not justifying our actions here…I’m just explaining what happened. And 20 years later, I still have fond memories.

Jessica and I were high school sweethearts, and ended up breaking up for reasons largely related to me being a complete idiot. We were teenagers, we’d fight over stupid shit because that’s what teenagers do, and we’d blow stupid arguments out of proportion. But this isn’t about that.

A few years after graduation, I saw her for the first time working at a shop in a mall a few towns over. I was expecting the conversation to be awkward, but we ended up chatting it up like nothing ever happened. And I quickly realized that everything that attracted us to each other the first time was still there. We quickly started to click. After that first conversation, I made excuses to conveniently show up at the mall right when she was closing. I’m sure she realized my excuses were full of shit, but she didn’t seem to care. Read more »

Hotel Convention (MMFF, Bi) Parts 9-12

**Part 9**
1415
After joking about how we’d need to run back to our room to get something, we both realized that the USB drive we were just given could wait.
Steve said, “If the mascot said that we should find her later, then we probably don’t need to see what’s on that drive right away. At this point, I think we need to wrestle some lunch out of that packaging supply company.”
“You’re probably right.”

Neither one of us wanted to overeat in front of the vendors, it seemed a bit late for lunch, and it made it easier to think that we did it to stay sharp, but I think we ate less than usual so we could go check out that drive. We thanked our lunch host, shook a few other hands, and told some people which lecture we were headed to in the later session.
1500
We headed back to the room, knowing that we had at most an hour to see what was on the drive and get back to the ballrooms for the next lecture. It was hard to tell if we were excited to see what was on the drive or if it was just that we were going to get a few minutes alone. We sat next to each other, not sure what we were getting ourselves into.
I loaded up a virtual machine session on my laptop, hopefully secured well enough that if there was any funny business it would stay right where it was. I laughed once I saw what the file was, though.
“What’s so funny?” Steve asked. Read more »