Tag: High School

When I [22M] hooked up with my friend [22F] the day after my breakup [MF]

This is my first time posting on here so I’m sorry if I’m not that good of a writer. Changed her name obviously. I have a few other stories of fun encounters. If this one gets good feedback I might share them too. Enjoy!

This is the story of how I hooked up with one of my long time friends a day after I broke up with my then girlfriend. The break up wasn’t particularly bad but it was a little rough and I just needed to do something to forget about it.

The night that this happened my friend who I had known since freshman year of high school texted me that she was going out to a bar with a few friends and that I should join her. I’d already had a few drinks that night so I said fuck it and I cleaned up a little and headed her way honestly not thinking anything was gonna happen. Read more »

My (22f) roommate (25f) has cut me off, and is teasing me [FM]

My roommate is a friend from way back. We didn’t see each other for years, and then we wound up in the same town. I moved in to her place as her boyfriend moved out. She’s got a nice IT job, so working from home was an upgrade for her. She also pays most of the rent, as she has her office and her bedroom. Aaaaand she’s a bit relaxed with her clothing.

That was a little difficult for me at first, but I grew into it, and I grew to like it. It wasn’t that I was a prude or anything. Honestly, I wasn’t comfortable in my own skin, and I’d experimented in high school. I already thought I was latently bisexual, and she was kinda pushing me towards it. I think I was uncomfortable because she was just comfortable in her skin, and I didn’t want to perv on her.

It eventually wore off on me, and I didn’t have much of a problem walking around in a tank and a thong. Top it off with the heat over the last three months… Yeah, I got much more comfortable wearing less. It became the norm for both of us to lounge around like this. It was her work uniform, for the most part. Read more »

A Sub for Dinner (MF)

“Wait, you mean to tell me you were crushing on me all through high school and NEVER said anything??” She was smiling and I couldn’t tell if it was devilish or not, but I still loved it. Brunette, curvy in ALL the right places, and just plain sexy. She’s looked that good for as long as I can remember.

“Well,” I laughed, “we kinda ran in completely different circles back then. I was more the quiet, nerdy type and you were with all the ‘cool kids’ if I remember correct. Still, I’m glad we ran into each other. Catching up has been fun!”

We just happened to be visiting our home town on the same weekend and bumped into each other. Small towns are good for that. I opted to grab a hotel in the next town over instead of sleeping on the uncomfortable couch of a relative. You were staying at your folks place, but they were gone for the weekend anyway, so it worked out. After the initial awkward greetings were out of the way we decided to meet up later for dinner at your folks’ place so we could catch up properly. Read more »

I “cucked” my boyfriend by fucking his best friend for his birthday. [FM]

This is my first Reddit post in literally about 4 years, but I really wanted to tell the story about how I fucked my boyfriend’s best friend on his birthday last January.

A little brief history, my boyfriend (Xavier, 24), his bestfriend (Ian, 26), and I (24) used to be inseperable back in high school. We were all super close friends. We’d always go to off campus lunches together, and hang out at Ian’s house after school to watch TV, smoke pot, play video games, etc… I even dated Ian for a few months back when I was 16. (We never fucked or anything, but we did make out and get “handsy” a lot.) Needless to say, we were all familar and comfortable with each other.

After we graduated, Ian moved super far away, and I eventually started dating Xavier. Things have obviously been great with us, because we’ve been together since. (6 years!!!)

Anyways, since Ian lives so far away, the last time we saw him before this story was back in 2017. So, 4ish years later, which was this last January, he came down to visit his family and friends for his birthday. Read more »

My first time cumming in front of a woman [MFF]

I was a pretty late bloomer when it came to sex. All throughout high school was on on the shy side and didn’t really do much with girls. But once I got to college I started to open up pretty quickly. One night during my freshman year a group of us were hanging out in my dorm drinking and just fucking around like we did on most Friday nights.

Long story short, the conversation turned to sex and it became clear pretty quickly that one of the girls in the group was totally uniformed about everything relating to sex. She seemed particularly mystified by ejaculations, but clearly didn’t want to say too much. The night carried on and eventually a few people went to sleep and the rest went out to a club, leaving just me and two of the girls in the room.As they were getting ready to leave we had one more drink and one of them just asked point blank: “so it really just shoots out?” I was no expert in anything but my own gear, but I told her that yeah, pretty much it just shoots out. And then she asked if she could see it. Read more »

Finding Love Again [M/F]

*** ***Laura*** ***

I’m grateful to Chris for making me feel desirable again and for making me feel loved, even though it was for a fleeting moment.

When Bella, Alana, and I were kids, our family spent Thanksgiving together. We took turns hosting it in each other’s house and, despite Alana’s house is much smaller than ours, her father still managed to host one for us. Our parents didn’t care about socioeconomic statuses, all they cared about is that their kids were best friends with each other and we had a lot of fun!

Of course, my stupidity and selfishness ruined that. Lately, however, our families have been talking about doing it again. Alana’s father, understandably, couldn’t host it anymore since he and Alana live in an apartment now, but regardless we’re going to start spending Thanksgiving again!

Well, next year we will. Alana’s dad has a girlfriend, my parents are out globetrotting and Bella’s parents are having their second Honeymoon. Bella’s and my parents are, rarely enough, so much in love with each other’s spouse that we’re afraid that we’re going to have younger siblings. Read more »

Amnesia Was The Best Thing To Happen To My GF [M/F/F] Part 19

*** ***Chris*** ***

I damn near tipped the chair over. That’s how my day is going to start I guess. Bella and Alana are still sound asleep, and I’m feeling mighty thirsty and I walked out and into the kitchen. There’s two empty glass in the sink. Who the… really? I washed the glass and looked in the fridge.

“Morning,” I hear and I immediately knew who it was.

“Morning, Dean,” I said and he immediately punched my arm, but then he kind of recoiled. Huh, did his punch get weaker or something?

“Damn, bro, you’re been working out?” I shut the fridge door and he got a better look of my shirtless body, “Holy shit, you really have been working out.”

“We’re really starting this now? At this time?” I said in exasperation. Dean and I are only a year apart and looking at him and how much he’s starting to slip up on his body, I’m feeling a bit more confident that I can take him if we start having our fights again.

He laughed and backed down with a dismissive wave. I grabbed a bow and poured myself some cereal and a bit of 2% Milk and dug in. Read more »

[MF] How being the sober one led to my (M26) first casual hookup (F21)

Growing up I was extremely shy and was far too nervous to talk to girls. I had one girlfriend in my early 20s but after we broke up I didn’t really date very much and I didn’t have sex again for four years, until I was 26. The girlfriend wasn’t my first sexual experience but she was my first love and we had a very active sex life and became very good at what we were into. Following the end of that, however, I reverted to my natural introversion and social anxiety and thought this was it for life. That is, until this first casual encounter. After that it was like the floodgates opened, and I made up for a lot of lost time, and while I’d always had a very very high sex drive I’ve since then also developed my tastes, interests, and kinks. I’m in my early 30s now, male, and in Australia, and I’ve dated, had short flings, had ongoing friends-with-benefits, had fuck buddies (less friends than FWB I think), had one night stands, and had a small number of BDSM focussed relations. But this is the story of the first casual encounter and the one that really got my confidence up. Read more »

My Sons Girlfriend

My Sons GF

Not too long ago my wife was out of town on business. My oldest daughter was away at school and my 20 year old son, Scott, was at work. I thought since nobody was home I’d spend some time at the golf club with the guys. When I got home and went upstairs to take a shower. I had my earbuds in listening to music so I didn’t hear any noise in the house. I hit my bedroom and stripped down. I turned on the shower, extra hot, and waited for a good steam to build. I got in and took a good long steam shower. It felt so fucking good to wash off the day.

I got dressed in some very loose fitting gym clothes. I wasn’t leaving the house so I skipped the underwear. My plan was to fix a drink and sit and watch some television. I opened the bedroom door and started to head downstairs. I could hear some noise from the family room. The TV was on. I could see into the room to see my son’s girlfriend, Kendra, stretched out on the couch watching a show. When I walked in I caught her taking a selfie to send to Scott. I jokingly said to her that I bet he really enjoyed the view. Read more »