Hannah, my roommate and boss [MF]

We’ve all heard the sayings before, the warnings from people who have learned the hard way. Never go into business with family or friends. Never sleep with roommates. Both usually end disastrous with one party out for vengeance, or feelings perminatly hurt. I would be the first to tell you that I had the best of intentions before I broke both of those rules, and looking back over the last 3 months would I do it again? You’re damn right.

A few months back our state Governor shut down our state in an instant. With the shutdown came layoffs, and with those layoffs came panic. I lost my job early on, as did my roommate Hannah. I had met Hannah through a mutual friend who had told me she was looking for a roommate for a small apartment. Hannah is a smaller BBW woman, she dresses as if she is from the 90s and has a contagious laugh that is easily her best quality. Hannah and I met for a beer and clicked pretty early on. We both have a similar sense of humor, and are clean freaks. I have lived with females before and there was never any issues with sexual tension. I work in the restaurant field so I was at least prepared in my mind to lose my job. Hannah on the other hand thought that she would be safe, a parapro teacher at a local elementary school she thought she would get paid through the duration. Hannah would realize that not being a union employee meant that she was not entitled to the same benefits. Long story short, as of the 1st of March 2020 both of us for unemployed with meager savings. Our attempts to get through to the unemployment office were unsuccessful. I had no fucking idea what I was going to do.

[F]ucking [M]y girlfriends best friend in the ass [Part 2].

I came home from fucking my girlfriend Tara’s(T) best friend, Bell (B) that evening. Tara and I spent some time talking about what it was lie with Bell and if we obeyed the rules, no fucking her pussy and no kissing. I sheepishly lied and told her no kissing, even though there was peck here and there. I let her know that I only fucked her ass and fingered her pussy to help her relax a bit.
*“Where did you finish”* Tara asked me, avoiding eye contact.

I suddenly felt nervous, almost ashamed *“Well, inside her”* I said.

*“Ah, I see”* Tara said, avoiding eye contact further *“Did you enjoy?”*

*“I did, but nothing beats you babe”* I playfully said, wrapping my arms around her.

Tara hugged me back. I pulled her in closely and our lips met for a passionate kiss. We made love that night, soft and gentle. I couldn’t help my mind wandering to Bell’s tight asshole. Morning came and I headed to work, Tara works from home. Giving me kiss goodbye, I slapped her on the ass and headed out. Bell texted me later the day, saying that it hurt for her to sit down and that she hadn’t been fucked like that in her ass in a while. I apologized and told her I’ll be gentler next time.

I [M] curiosity got me in the wrong place

At one point I was very curious and horny when I turned 18. I was on the internet looking for live cams to hopefully run into a female looking to have fun. After an hour of what seemed like forever just clicking the “next” button. I finally stopped and stumbled upon a black screen. They typed “nice body” and then followed by a longer text stating “would love to invite you to something fun if you’re interested”. I said sure and then he sent a link. The link sent me to a webcam website that started with a B. I’ve never stumbled upon it since, but I was the only one. Soon I was followed by a random text bubble saying “hot body I’d love to see your cock”. For some reason something came over me and my cock got hard. You could see the bulge growing in my shorts. “I see that, take it out. Don’t be shy”. My cock was throbbing and decided to take it and and immediately take one big stroke. Showing my uncircumcised head. I glanced at the screen and saw that there was now a webcam on and a male with his legs spread was on the camera. His balls and cock were wet and glistening. I started to get my rhythm and I noticed two more webcams opening up. Did I accidentally find myself in a group webcam? Was I about to cum for all these strangers.

I [M] found a pic of my mother-in-law’s pussy and I jerked off to it

Ok so first, I’m sorry for my terrible english and I’ll hop you’ll understand and enjoy my confession.

I’m 26 yo and I’ve been with my gf for 4 years now.
3 years ago, my gf’s parents divorced so my mother-in-law is now single (at least “officially”). She is an attractive woman even if she’s 47 yo. She has curly brown hair, green eyes, she’s quite skinny but with a good pair of boobs, probably a C cup. Moreover, since her divorce, she’s in that “single mom who has decided to enjoy her new life” mood. Therefore, she pays attention to her clothes and she often tries to look attractive. I have to confess that I’ve been staring at her ass and cleavage a few time by the past.

Anyway, that day, I was at my mother-in-law’s house with my gf but her mother was not here. At a time, my gf was buzzy calling a friend. As I was alone on the living room, I started scrolling on the iPad of the house…so the iPad of my mother-in-law. Then, I did something that I shouldn’t have done : I looked on the pictures gallery of the iPad and …I start searching on the “recently deleted” folder.

[MF] I accidentally fucked my ex in front her open window and her housemate[F] saw

Back a few years ago I had just gotten out of university, but due to a lot of personal/family issues, I spent my first summer after school at home helping out where I could. This lead to me being a bit cooped up and I decided/my friends convinced me to visit for a party that happened to be 4 days before my birthday.

Now when I was in university, my friends and I partied a lot. I wasn’t and have never been a playboy, but to say I was playboy adjacent would have been very accurate.

Anyways, I had met Sarah at a Toga party the previous year. She was stunning. Like out of my league gorgeous. Imagine a blonde bombshell with a girl next door vibe. The toga didn’t show off her breasts, but it hung nicely off of what was clearly a very nice and shapely ass. I later learned she was a dancer, and boy did it show. We had a short, but intense relationship, as I later learned was kind of her MO.

Update: told my [F]WB about my neighbour [F] listening to us, so we put on a show (bonus pic included)

After my last post telling you about my neighbour Ana (who I slept with) which followed with her telling me she how loves listening through the wall to me having sex, I decided to tell my FWB.

I had invited my Jay (FWB) over yesterday (not at the request of Ana), and decided to tell her what had been happening. Jay is open minded and also happens to be very sexual, so she was turned on by the thought of someone listening to us fuck. I text Ana asking if she was home, she replied and said yes, asking if I needed something. I didnt bother replying because by this point Jay and I were both really turned on. Jay wanted to put on a show, so she pushed me against the wall that is adjacent to Ana’s room, quickly stripped naked and got on her knees, this caused me to start softly moaning. After a few minutes we changed positions and I warmed her up, luckily she was already soaking wet – so her moans were already louder than mine were. “Fuck me already” Jay says louder than usual with a smirk on her face. I stand up, spin Jay around and start fucking her from behind with her hands pinned against the wall. I didnt waste much time in starting to thrust harder and harder, Jay was looking back at me over her shoulder and started to moan and pant with each thrust. I started taking longer strokes so my hips were slapping Jays ass she was moaning louder and louder, deliberately putting on a show. Jay is usually quite vocal but she took it to the next level and started talking more(usually its mostly moans), telling me to fuck her harder and panting louder.

For real though, how [M]any of these stories actually happened?

I’m not sure if I’m allowed to post this. Apologies if not, please don’t ban me. Are these stories here actually real? Like the top ones, do we all agree and think they happened? I want to believe all these for lots of reasons, but if I’m the only one not in on the truth I wanna be. Haha.

Lustful island drive [MF]

30 minutes into our drive up island…

I start to rub your clit through your panties. Your hips sway even more. I can feel your wetness and heat through your CK panties. I can’t wait to finger your pleasure hole. I ask you to bend forward as insert my hand under and around to your warming ass. I grab it and play with it. And tease your asshole and then Labia from behind.

I cannot hold back any longer as your juice is flowing right back into your ass crack. I slide in a finger and cradle your clit with my thumb, you exhale with ecstasy. I rub your g-spot and clit and you forcefully push your hips and ass onto my hand and my arm almost snaps.

Meanwhile you decide enough is enough. We are now on the highway past Parksville. Kind of in the wilderness. You unbuckle my jeans and pull them down my legs. I put the truck on cruise control. You look at my swollen cock and gasp again as I stick a finger so deep up your wet pussy.

[FM] The Weekend Getaway Part 1 [mentions of group sex]

You can [read one of my previous stories](https://www.reddit.com/r/gonewildstories/comments/gt7qyl/fm_my_boyfriend_came_inside_me_while_a_friend/) for background on the main players, but TL;DR my boyfriend Henry and I went to a cabin for our one year anniversary with a group of five friends, two of whom are named Elizabeth and Tony. We suspected them of hooking up that weekend, but didn’t have confirmation.

For context, Tony is bi but he usually dates women, I’m pan and date anybody who makes me laugh, and Elizabeth and Henry are both mainly straight. I say “mainly” because Elizabeth had brief dalliance with her married female Sociology professor during college (SUCH a cliche), and Henry used to occasionally get off with a male friend in high school during dry spells. The moral of the story is that sexuality is fluid and labels help us communicate what’s going on but don’t always accurately describe it. Also for context, Tony and I once had a threesome with a male classmate of ours at the beginning of grad school before I met Henry. I promise I’m writing up that story, but it’s a struggle to not make it sound like a cheesy porno. Henry knows and doesn’t really care – it was only one night, and Tony and I transitioned to a completely platonic friendship soon after.

[MF] The second time I got a handjob off Craigslist

So this time was a little different, on Craigslist personals I posted “add me on SC to watch me cum”, and I would get a lot of people adding me, mostly female, males of course even though I asked for only women. On the post I also mentioned we could meet up in person and they could watch me jack off for them. Later that day I got an add on Snapchat and this girl and I talked for a few weeks and she would watch me jack off for her on snapchat. We exchanged numbers but she would never really answer or have the time to meet up. Then finally one day I uploaded some videos to my story and she messaged me on Snapchat and inviting me over to finally meet with her. So she sent me the address and I did not hesitate. She told me her friend was there but it was okay her friend is cool with it and she would watch as well. So when I pulled up and parked in her apartment complex parking lot she messaged me that her friend changed her mind and she wanted to do it a different day. I told her I was outside already and she was like “nevermind my friend can wait in the apartment I want this!” And about 2 minutes later I saw a beautiful curvy black woman walk out from the complex and I stepped out of my car hoping to god it was her. “*Name*” she called out my name and I let her know it was me and I walked towards her and she gave me a hug and we walked back to my car. When we got in she was staring at my shorts already waiting to see me.