Category: gonewildstories

Fucking my [M] good friend [F] while her boyfriend was gone

This is a story from a number of years ago. It was one of the most exciting sexual experiences in my youth. This turned out to be longer than I expected.

In the summer of my sophomore year of college, I would spend my downtime chatting with friends online. Jennifer was one friend that I would chat with regularly and happened to also live in the same town. We had known each other when we were much younger from elementary school so we had a bit of a past. We would chat pretty much every day and talk about pretty much anything and everything going on in our lives. She was a very cute petite girl: blonde long straight hair, blue eyes, glasses with a slim and fit physique. She had a somewhat serious boyfriend that she was living with at the time. We were pretty close and had light flirty conversations, but never anything sexual, and I did my best to respect that boundary because she was attached. Read more »

[F]I was almost caught masterbating at work

So if you have read my other confessions you would know that I’m a housekeeper in a hotel and spend a lot of time alone in the rooms where I would just finger or grind on things in the room and on this particular day I was playing it safe my just pulling my leggings down and fingering myself in the bathroom when I heard the door too the room open and I don’t know who it was or why they were in there because I froze and didn’t move a muscle. Idk because if they went into the bathroom they would have seen me bottomless and very wet and legs spread and I didn’t move for about 3 mins before I heard them leave. Honestly it turned me on so much I squirted and had to clean it up.

A story of hooking up with a nerdy woman (part 2) [MF]

This, is a part 2 (and finale?) of my first story found here:

[https://www.reddit.com/r/gonewildstories/comments/v8vbhc/i_25_m_received_the_blessing_of_a_nerdy_29_f/](https://www.reddit.com/r/gonewildstories/comments/v8vbhc/i_25_m_received_the_blessing_of_a_nerdy_29_f/)

You might want to go there for context and exposition.

I (25, M) and a young woman known as Evie (29 F) had masturbated together and Evie had given me one of the better blowjobs of my life in her room, at her apartment, shortly after we had dinner with her roommate Madison. Madison and I had been dating(?) for a couple months with nothing physical occurring, as she was a devout Christian, and I was a filthy Atheist heathen.

Evie was a slightly older woman with a Velma aesthetic. Very shy, a little curvy, and very nerdy. Madison, was basically a brunette disney princess who spent a majority of her time at choir practice.

Well, to complicate matters, I mentioned the three of us worked for the same company? In the weeks that followed our initial exchange, Evie and I would sext at work, and send nudes during and after work. We never wound up making out in the breakroom, or fucking in the bathroom stalls. But she would send me video of her touching her (now) shaved pussy, or pulling her frumpy clothes aside to reveal her pendulous, full, round breasts. I would reciprocate by sending video of myself jerking off and cumming. Sometimes in very familiar settings (her room, my room, the bathroom stall at work). Read more »

Fucking two guys after a frat party [FM] [FM]

During my junior year of college, I was hooking up with this guy Max. He lived in a frat house, which made it super easy to stay over whenever they had a party. We weren’t exclusive, but it was fun to have a reliable booty call.

Early on in the spring semester, his frat had a big foam party. Assuming I would be spending the night, I brought a dry set of clothes to leave in Max’s room. I’m about 5’3″ and was about 110 pounds back then, with B-cups and a runner’s body. I changed into a bikini, cute athletic shorts, and flip flops and headed downstairs. The entire basement was filled with waist high foam, and was super packed! I saw Max behind the bar chatting with his friends, so I made my way over to some of my friends and started dancing with them.

Sometime during the night, I started dancing with this guy (whose name I would later learn was Jake). He was tall and really muscular, and I felt really small as we got closer and closer. We were making out before too long, and he was running his hands all over my ass. We kept dancing for a bit, and then he said he had to go to the bathroom. Read more »

First anal for pregnant coworker [MF]

Stephanie and I used to work together for a couple of years, and often chatted about various things. She was not the woman you would typically call hot, her tall, slim figure, thin hips and small breasts didn’t offer a lot to look at. She had a cute but average face, dirty blonde hair and wore thin glasses. But she had an amazing personality, she was smart and witty. She was in her late 20s and I was 35 at the time. The conversation sometimes did turn flirty, but it was more fun banter than either of us being serious about. I had no way of knowing, but I always thought that she never was too interested in dating and I was convinced that she must be rather boring in bed. Read more »

[FF] Preparation for Hubby’s B-day

Hubby’s birthday is coming up this week, meaning NV and I have started our scheming. We still have a couple days, but we’ve booked next weekend at our favourite hotel, we both bought matching lingerie aside from the colours I went with black, she went with white, which also led to us having some flirtatious fun in the changerooms, consisting of mainly eating each other out and sharing some sloppy kisses with our lips soaked in each other’s cum. Perks of working at VS and being super close with the owner. We also got some naughty “candy,” which NV’s never tried, and it’s been a couple years since my last time, and we’re also working on bedazzling our new robes, so they say Daddy’s Lil sluts on the back. Then finally, we were debating bringing some microkinis with us, which would be a big step for NV since she’s never worn one before and, realistically, would only wear it in the hotel room since it’d be one of mine, and they don’t leave much to the imagination. Read more »

My Friend Loves Porn, and Helped Me Find a Girl To Fuck In Front of Her [MF]

I have this friend named Alexis. I call her Lexy. I met her online because we have common kinks. We began to talk and learned that we go online as a release. We explore our deepest and darkest kinks that we would never share in the real world. None of our friends and family know this side of us, and that’s how we like it.

Lexy is interesting, because she LOVES porn. She thinks it’s so hot to watch people fuck. Lexy and I have had sex multiple times. I learned that she likes to have porn on in the background while we fuck.

She told me that she wants to watch me fuck someone. She doesn’t want to participate directly. She just wants to watch us fuck while she rubs her pussy. She said she’d suck my dick and let me fuck her for a few minutes to get my dick hard, but her main goal was to just watch while she masturbated.

At first, I set up online accounts and wrote in the description that I was looking to fuck someone while a friend watched. I didn’t get many responses to that. And those that did respond, weren’t exactly the type of people we were looking for. Read more »

I [F] blew a guy as he sexted his wife

So I’m not into cheating, the wife in question was fully aware of what was going on.

I like meeting up with men who travel for business because it’s low commitment, they are often older (I’m 22), and they need to let their frustrations out.

I matched with this 44 year old dude on tinder and we met up a few times. The first few were my general degrading sex and roleplay visits, but our last encounter was a bit more exciting.

He told me his wife wanted to text him while he used my face. He promised me she was cool with our encounters, and that she loved degrading his sluts. So being the cock hungry slut I am I agreed. Our big rule was he could only text her, or record audio clips of himself. No filming me or taking pictures of me.

He had me lean my head off the bed, that way he could thrust into my mouth and have his hands free to text. He’s cock was decent size but not huge so I was able to take it all no problem he fucked my face hard, occasionally warning me he was recording voice messages for his wife, and reading me all the slutty names she called me. Read more »

[FM] Helped my flat mate to show her brother around our place. It ended up with him balls deep inside me the next hour. But the worse thing is that we got caught by her…

Kinda fucked up story to tell Reddit but seems like the correct place to let it off.

Short context: so my flatmate’s brother (name is A) came to our student dorm today to vist his sister place because he would soon becoming a freshman of our University in a few months time. Kate – my flatmate asked if I could greet him and show him around instead cause she needs to work an extra shift. I said alright no problem. But my dumb ass thought it would be funny to tease him in my [robe](https://www.reddit.com/user/Puzzled-Rule9387/comments/vkevr7/prepare_for_trouble/?utm_source=share&utm_medium=ios_app&utm_name=iossmf). Also did an equally stupid thing which is asking Redditor to provide me with some ideas for it. And my god it actually worked.

“Stuffs” that I have performed:
– Reached out to open the tab for the bath in the common bath room.
– Slightly bending down to open the oven.
– Drop a pen on the floor and picked it up
– Jumped on Kate’s bed to adjust the drape and pillow. Was on my knees so hopefully he has got a good look but god knows if he actually did.
– Asked him to check out my room to see the different in the view since Kate’s room is opposite to mine. Told him to feel free to have a look around while I’m outside getting some drinks. Hope he found something interesting. Read more »

[MFF] Masturbating for my Roommate and her Friend

It was a Friday night like any other. A long week of work was over and I was exhausted. I had no desire to do anything other than order a pizza, drink some beers, and find a movie or two to watch. My roommate at the time would be out on the town with a friend she went to college with and thus I was looking forward to a nice quiet night in the apartment.

Fast forward to around 1am, the night has gone exactly as planned for me and I’m nearing the point of heading back to my bedroom for some intimate self care and a long slumber. Right before I’m about to retire I hear the door to our apartment unlocking. It’s my roommate Katie and her friend Lisa. They burst into the apartment rather boisterously, clearly they’ve been having fun tonight and their drunken laughter fills the entire apartment. I hear them fixing themselves fresh drinks in the kitchen before the clack of their heels grows louder as they head towards where I’m stationed on the couch in the living room.

”Oh hey there, didn’t know if you’d still be up! Mind if we join you for a drink?” Read more »