Nothing like a good challenge [FM]

*Really appreciated the amazing reaction to my first story:* [*Six Close Friends in a Dark Closet*](https://www.reddit.com/r/gonewildstories/comments/fppy8e/six_close_friends_in_a_dark_closet_group/)*. At over 3.5K upvotes, I’m absolutely floored by the response, and everyone’s PMs of support and thanks. This one’s a bit different, but I hope you’ll still enjoy it!*

This story takes place during my freshman year of college. I wanted to try and meet some new friends outside of my little bubble and joined a study group for a large gen ed course. It was there that I met Aaron, an older tall nerdy kid who was overly friendly and easy to talk to. I’ve always had a thing for guys with glasses, and slowly realized I had a bit of a crush. We hung out quite a bit over the first couple weeks and my advances weren’t quite working the way they usually do. It was strange – I could tell he liked me, or at least was attracted to me, but he seemed to always be stopping himself from making any moves.

[Group] First goursome in a tent, hottest night of my life

I have always love going to festivals because the girls are always so excitable and ready to party! This was the first festival of the year (2019) and I was ready to rock! It was me and a big group of my friends from high school, we drove up the country to get there and after a 4 hour car ride we were all ready to get out and party!

We got inside the venue and pitched our tents, I was in a tent with my friend Daniel. He is a few inches shorter than me at 6’1 (Im about 6’2) and he is quite a looker with big arms and a fairly built body. For context, I am also a bit built with toned arms and thunder thighs. I dont see it as much of an achievement because these girls are all so horny and drunk, but Daniel and I get a lot of girls at these festivals and this time around we were extra ready for a party.

[M]y First Escort.

My first escort was when I was the age of 19, I’m 23 now. I was in college and my roommates were either out of town or at work and we lived in a town house in an apartment complex near the school I attended.

It was late that night and I was on my phone browsing escorts on backpage (this was before it got banned). Now for the record I’m a pretty decent looking guy so I really don’t need to be doing this but I find it super hot to get an escort. Maybe it’s the fact that you just fuck them and it’s meaningless, I don’t know. Not a single person knows I’ve done this too.

So, I came across a young (I was 19, younger) looking girl that caught my attention, Vanessa. Her ad said she was 18 but she might have even been younger, I’m not sure, but I liked what I saw. I like petite looking latinas with a pretty face so I was intrigued.

[FF] I gave my roommate a full body massage with a happy ending

Hello! It’s been awhile, but I’m back again with another story about myself and my roommate, Layne.

First, a quick reminder about what we look like:

I’m Brooke. I’m 20. I’m bisexual. I’m 5’5, with short-ish dark brown hair and blue eyes which I’m told are large and innocent-looking. I’m relatively pale, despite my best efforts to tan. I guess have a little of an hourglass figure. I’m only 130lbs but I have decently sized boobs with wide hips and a big, round bubble butt! My butt is my pride and joy, as you can probably tell from my username haha.

Layne is gorgeous. She is 21. Physically she is quite different from me. She is taller by a few inches, with dirty blonde hair that she almost always keeps in a ponytail, and lightly tanned skin. She has a slightly more athletic frame, with large, natural breasts that form the perfect cleavage. Her butt isn’t quite as big as mine, but it still fills out her pants nicely, and she has long legs to go with it!

[FM] Fucked my college professor in his classroom and almost got caught

Okay this is my first time posting on this sub so hopefully you enjoy it! Also this happened around finals at my college back in december!

Since it was a few days before finals and everyone was stressed, I decided to go to tinder to find someone to take my mind off of all that was going on and have some fun! While swiping through, I find one of my professors on the app. He taught the class I was having the most difficult time with (a science class if anyone was wondering!)

He was not the type of guy I usually would match with considering he’s like 30 years older, but I don’t mind that at all. I swipe right, we match, and we exchange some texts! After a few messages, I tell him I take one of his classes but it’s one that has over 200 students in it so it is no surprise that he did not know I was one of his many students! Since I have class the next day with him, we agree to meet up before my class starts and get to know each other.

[MF] Milf next doors Daughter

So a while I (Male 25) ago I told you all about my adventures with my next door neighbour (Female 51). Well nothing really happened after that until her Daughter (Female 25) came home after months away. She’s about the same age as me, and I even went to school with her. I always had the biggest crush on her but never really had the chance to tell her. Shes about 5’2. She not fat but certainly not thin, honestly has a perfect little body, and pretty big boobs to boost.
So anyway, she’d been away for a while, with her Fiance, or ex Fiance now, and had nowhere else. So she moved in with her mum, which meant I wasn’t needed anymore.
We started chatting over the fence, at first she just wanted to thank me for helping her mum out. But over the past few weeks we really got talking. About how she’d just gotten through a nasty breakup and how it was nice to have someone to talk to. And eventually she invited me over, I know in these times I shouldn’t, but, she’s hot.
So I spent the evening next door, had a nice dinner, things felt a little weird with the two of them in front of me, knowing that her daughter had no idea. We then watched a film, but you’re not reading for that. At the end of it her mum decided it was bed time, and wished us both goodnight. Leaving just me, and her daughter.

[MFM] Our first threesome at a sex club

My ex-wife and I started going to swingers clubs during the final year of our marriage. It all started when we were planning a trip to Vegas. She wanted to see a topless show, and somehow the research of that morphed into researching strip clubs, and then finding out about swingers clubs.

We had months until that trip was coming, so as time went on, we researched clubs closer to home. We started going about once a month, and we both loved watching, and being exhibitionists. We’d role play at home discussing involving other people with us, but we never did. There were a few times we would have sex in the common areas that other couples would join on the bed next to us, but that was the closest we ever got.

Then we separated.

Of course we kept fucking. We had a great sexual chemistry, so why not?

Then we decided to go to one of the clubs together. Since we were now separated, I think we were both more comfortable with anything happening. We had both been fucking other people, so we were really cool with it.

Ben and his hotwife [mmf]

A few years ago I met a guy on reddit (Ben) who loved posting pictures of his wife (Michelle), a stunning hot chinese girl who had an incredibly good body and was teasing him about still fucking her ex.

As we continued to speak I was asking Ben about Bulls fucking Michelle and he said he had always wanted it but his wife had never said yes. She always wanted to fuck the ex because he was well hung, had huge loads and would fuck her 4 or 5 time’s in a session.

As time went on and she posted more and more incredible videos of her ex fucking her and cumming all over her and I started to plan with Ben of how we could get her to enjoy the bulls and be shared by more guys

Ben and the ex new each other quite well and the ex was going on a trip soon so the husband and I put our plan to work, with the ex fully aware and keen to see Michelle being shared out more. A few days before he left Ben saved my number on Michelle’s phone with the ex’s name and his picture and I messaged her saying that I had a new number whilst pretending to be the ex.

[MF] A teasing start to the day

Today is the start of vacation for the family. Because we were going to hit the road before lunch, I decided to skip the gym (they’re open in my state). As a result, I woke up morning wood and decided to shoot my shot.

I shimmied out of my boxers, and then reached over to my wife to start rubbing her back and fondling her breasts to wake her up. Her eyes didn’t open, but there was a sigh and little wiggle as my hand slipped up her t-shirt to start playing with her nipples.

She rolled over, looked at my sleepily, kissed me, and moved her hand down to my cock. When she realized I was naked, she smiled and commented that I was pretty confident.

Her hand was gently wrapped around my cock, slowly stroking. It was almost like she was barely touching it, but every graze was amazing.

“I’m sleepy,” she said. “Can I just jerk you off?”

“Yes. Please. God.”

The lack of constant contact was driving me insane, and every touch I did get was sending shivers through my body.

“Faster, please.”

My signal to my BF, that I just got fucked by another man [MF]

A while ago, I was dating my BF at the time. He had some cuckold tendencies that we were really able to explore together. I don’t know, maybe I tend to be more attracted to this type of guy.

When we were dating, he encouraged me to fuck other guys. FWBs, fuck buddies, random Tinder hookups. It didn’t happen all the time, but often enough. He used to love to see me after the fucking. We had this secret signal that we used, to indicate that I just fucked another man.

I would wear this pink silicone ring on one of my fingers. It’s something I wore in public, and only he would know the true meaning. Sure, I would get a few compliments from friends, saying how pretty it looked. But what my friends didn’t know, and only my BF knew, was that I just fucked a guy who wasn’t my BF. So we would meet up for a date or something, I’d already be wearing the ring, and my BF knew exactly what I was doing, or where I was coming from.