The Story of [M]y [F]irst Internet Hookup

So this is the story of the sluttiest thing I’ve ever done.

I was 22 at the time. I was just out of a 5 year relationship with my first and only high school girlfriend, and i was truly single for the first time since becoming an adult. Our breakup was less than amicable, seeing as how we were both trying to end our first relationship and had no real idea how to go about it. Needless to say, it was a rough patch, and without going too much into detail, suffice to say I was in the mood for some exploration. This led me to OkCupid. And OkCupid led me to, for the purposes of anonymity, Toni.

Toni was an older woman. Well, at least it seemed that way to me at the time. As a 22 year old man, 9 years seemed like a huge gap. However, this just added to her allure. I had never been with someone who wasn’t my own age, and she seemed so confident and sure of herself. Little did i know that this night would be the start of a long and lustful fondness for older women. Toni was my first match on OkCupid, and she sent me my first message. Her agenda was summed up very succinctly in 4 words:

[M]et and [f]ucked a girl off of Omegle [cheating]

For a variety of reasons, I’ve always had a hard time staying faithful in relationships. Porn addiction, sex addiction, whatever you want to call it. One of my guilty pleasures was using Omegle for cam sex. I don’t know if it’s anything like it used to be, but damn there were some hotties on there! This story took place about 6 years ago now. At this point I was in a relationship going on a few months, but I figured what the hell, I’ll log on and see what’s happening. I didn’t have any cam sex that night, but somehow ended up talking with two girls across the country from me for about an hour. One of them was a little chubby but had a cute face, but the one I was really attracted to was Holly. She was a redhead (my favorite), freckles, 19, pretty skinny as far as I could tell but it was hard to get a good look at her body with how the camera was facing. We exchanged numbers after talking for a while. Figured it would be like the rest of the numbers I collected off sites like that – chat for a few days before things fizzle out.

My Cum Guzzlin’ Maybe Bipolar Cheat [affair] [deepthroat/gagging] [anal play]

***Out of the blue, I got a text from Mia.***

*MIA:* Hi.

I had just set up my laptop and monitor at my workspace. It takes a few minutes for me to take out all of the wires from my backpack and hook everything up. The workspace manager doesn’t recommend leaving your equipment unattended despite security cameras in every room.

*MIA:* Come over real quick

*MIA:* If you can

People leave their shit out all the time, I thought. Here was my chance, after 2 years, to finally fuck Mia. After she sent me pussy pics and me dick pics. After I’d called her “undiagnosed bipolar”.

*ME:* Gimme 20 min

I left all of my stuff. Whatever, I thought. The only person that would steal someone’s stuff is me anyway.

I got in my Camry and glanced in the rear view mirror at my teeth – looks clean. Started up the car – 1/8 of a tank left. Mia’s apartment wasn’t too far away. I could make it there and still have enough gas to last me until the nearest station.

I[F] cheated on my bf with a stranger[M] from tinder

This happened a few hours ago and im pretty sleepy so please excuse my english thanks.

I thought I was going to make it out of the quarantine
unscathed, but here we are. I know that it is irresponsible to break the quarantine, but ya girl needs some dick.

My boyfriend is stuck at another country due to lockdown, and im left alone in our apartment. I tried sex toys, porn, sexting with my boyfriend, I never felt satisfied. Even before my boyfriend left for his business meeting, I was never satisfied.

It started from imagining being with another guy, to fantasizing while I play with myself then lastly, downloading tinder. I got so wet thinking about the ocean of guys messaging me asking when and where we could fuck.

I matched with a cute guy, lets call him Dave. Dave was tall, toned and was hot. He looked like he could be a model. He was way older than me, and im into old guys so thats a check for me. He wasn’t boring to talk to like the other guys, so I was interested. He likes being rough and so did I. We agreed to meeting up.

Another time that I [m] waited on the couch for her [f]. Long and Detailed.

My last story was about the first time I ever purposefully let a girl walk in on me while I was edging, this story is about the second time that this happened. It was the same girl that walked in on me in my other story and it took place a couple months after the first story. To give a little more context I’ll describe her a little bit. For the purpose of the story I will call her Amanda. She was about 22 or 23, about 5’6″, a little on the heavier side with the benefit of huge boobs and a giant ass. She was very curvy with brown hair and some of the sexiest lips that I have ever seen. She also had huge brown eyes that made blowjobs even sexier. She was just as horny as I was at all times and had very few limits.

Now on to the story…

A couple fantasizes about a friend [MF]

The weekend had begun. For Arun, that usually meant a house party with his close friends. But this particular week, each and every one of his friends were either out of town or were too busy to meet. But Arun wasn’t complaining. Because he could spend quality time with live-in girlfriend which on a Friday night usually led to sex. Arun was already very horny, so this was just perfect.

“Let us watch a movie.” Preethi shouted from the back. She had just finished a long shower.

Arun cursed under his breath. A movie at this time meant both of them would be too tired for sex by the time it ended and they would end up sleeping. Arun was about to complain but then Preethi emerged from behind.

Preethi stood in front of him, her head tilted on the side. She was drying her curly hair with a towel. She wore no makeup, But her round face was radiant as ever. Her comfortable baggy pajamas and t-shirt couldn’t hide her curvy body. They has been dating for a year and living together for 6 months. Her presence always had a calming effect on Anil. She was just perfect for him.

Finally losing my virginity to my dream girl in high school (Part 3) [MF]

Thanks to everyone for the outpouring of support! Here’s part 3.

Part 1:[https://www.reddit.com/r/gonewildstories/comments/gfbhdz/a_lifechanging_high_school_blowjob_mf/](https://www.reddit.com/r/gonewildstories/comments/gfbhdz/a_lifechanging_high_school_blowjob_mf/)

Part 2: [https://www.reddit.com/r/gonewildstories/comments/ghdxzv/sneaking_off_with_my_dream_girl_at_a_high_school/](https://www.reddit.com/r/gonewildstories/comments/ghdxzv/sneaking_off_with_my_dream_girl_at_a_high_school/)

Preface: some details have been changed for the sake of anonymity and storyline, but all the plot and events are all true. I love almost all the PMs I’ve gotten but please, stop asking for pics of Jules. It’s not happening. I’ve posted my own nudes but don’t feel comfortable sharing hers.

Even before the nights we’d spent together, Jules had always been in the back of my mind. But in the last few weeks, she’d become the only thing I could think about. I couldn’t stop thinking about her reactions. The way her eyes lit up when she unbuckled my pants. How she giggled. I felt so lucky. I thought it was just a matter of time before I lost my virginity to her and it flooded my head with excitement and anxiety every day. Even with all the things that’d happened, I didn’t know how we would take the next step with her. I still didn’t have the confidence to make the next move. I spent all weekend again hemming and hawing over what to do. Should I wait? Should I let things play out and maybe things escalate? Or should I ask her out? I spent hours torn over what was next. I’d never asked anyone out before. Even if I decided I should, how would I do it? But as Sunday afternoon rolled around, a text from Jules made my decision for me.

Taking three for the team. But I did it for the art… [Group]

While I was at University I made friends with a particularly arty farty group of ‘creative’ people. Arty-farty in the literal sense as they were studying art in its many and various forms. One of these friends was working on a piece which examined the relationship between pornography and social media, holding a mirror up to society’s eagerness to shame sex scandals while simultaneously consuming porn at a tremendous rate behind closed doors.

It was a truly brilliant concept, and an excellent piece of work. It was provocative and intriguing, scandalous yet essential. It involved the use of some hardcore pornography, but it was entirely artistically justified.

But he ran into an issue because as part of his installation, he required a piece of intimate video. And due to copyright, intellectual property, and permissions etc, he wasn’t able to use any existing footage.

Which meant he needed to produce some himself.

Long story short, he needed someone willing to let three guys ejaculate over them on film as part of the project. Faces would be blurred to protect identifies, and there was no penetration or actual sex, it just needed to be ‘climax’ and the resultant mess.

[MF] my first time with a girl

Just a little context,so a few months back my (M27) friend (F25) and I, hung out at her place and drank. We had never hung out before but she just moved back to town and I hit up on instagram and after a brief back and forth she invited me over. The night was fun and i was not expecting it turn the way it did.

We got drunk, she suggested playing a game, so we played “never have i ever,” which was just her way to ask me my sexual past. I had to admit to her then I had no sexual experience before. So that game ended quickly. She at some point is laying down with her head on my lap looking up at me. We’re talking about how i was still a virgin; she thought I was actually lying and it was just some “move.” I was honest and told her no. I remember stroking her head and asking if I could kiss her. She smiles and says yes, so I leaned down and kissed her! Not really making out with tongue or anything.

[M]e Tit [F]ucking A Friend

[M]e Tit [F]ucking A Friend

This story takes place in the early 2000s when I was in college. As with my previous post, I was still attending school and working part-time.

This particular story involves a girl named Danielle- an average looking young woman whom I had known for several years since before high school. Danielle had two excellent things going for her. One, she was rather exotic looking- she was half Puerto Rican and half Dominican, and two, although her body was nothing special, she was blessed with a spectacular pair of tits or “cans” as my friends used to say.

Danielle always attracted the attention of the guys at school because of her “bags” but was actually known as being prude and never really dated anyone. I didn’t know anyone who had ever hooked up with her.