Category: gonewildstories

I (m) was thinking back on that one time she squirted.

I used to have this friend with benefits. I worked the front desk at my gym and she was a member. There was a colleague who had a crush on me but was NOT my type, so this member comes to me and says, “Hey listen if you’re not into her, I can come down and kiss you in front of her and say, ‘see you tonight’ and she’ll get the message.”

I took her up on the offer and it worked. I texted her later to say I really appreciated her help. I needed my colleague to help cover shifts and if I told her to leave me alone, she might get pissed and not cover my shifts … selfish. But whatever.

She responded to my texts and was flirting big time, so I flirted back. One thing lead to another and she revealed that if I were to in fact come over later, she’d have to take herself to the spa and get waxed. I’m really into a big bush, so I told her that wouldn’t be necessary at all. Read more »

I (34/M) fucked my (45/F) boss while traveling on business last week

I travel a lot for work. From time to time my boss will accompany me on some VIP type meetings. Last week was one of those times. We were in San Fran and, to make really long story short, the hotel screwed up our booking and had us booked in one room rather than two separate rooms. After some protesting and some escalation, nothing could be done as they were 100% sold out. So we had no choice but to stay in the same room. A little awkward but we’ve worked together for several years and have been on several business trips together so not TERRIBLY weird.

So my boss is a total milf. Remember Desirae Spencer? She looks very similar to her, except the tits aren’t quite as big. When I first started working for her I totally wanted to fuck her. She dresses well – always wearing tight skirts and nice button up, with the occasional dress. And she’s really smart, which is a big turn on. Anyways… Read more »

[25M/21F] WWII role-play

This is a much better, consensual role-play similar to what I previously posted. Other then the date and the role-play it’s not really different from other sex in terms of just doing some kind of uniform fetish. There’s limitations on things that wouldn’t be done then, which feels really geeky to say.

I was having a really nerdy WWII fetish that I wanted to try but I was afraid that it would make my girlfriend think I was really weird and I was worried about whether it was a holdover from worse times. I went on /r/Sex and asked about it would seem really weird to ask about, and I actually got very positive feedback. I told my girlfriend about it and she said that it sounded interesting to try even though she thought it was very unusual. We planned to go on a date as a Red Army officer and a German girl. Even though I have Autism (if that’s a surprise) I have social discretion and planned to go on the date somewhere outside of her college so she wouldn’t have to look like a weirdo to everyone and possibly get hit on by sovboos. We made the uniforms with a green henley shirt, slightly brown green dress pants, black rain boots, and a Soviet ushanka. She wore an overcoat, a white button shirt, a gray skirt, and those leather hipster boots that look like something from the 19th century. She also knows German so we spoke that. Read more »

(M)y successful experience (F)rom RAOMD

I’m not much of a writer but I hope you all will enjoy my account of this amazing experience.

A few months ago I posted looking to pleasure one lucky lady with my mouth. I received two replies to my post and one really caught my eye. It was from a guy asking if I’d be interested in showing his girlfriend a good time. He included her username to look at her post history so I could see her pics(she posts to r/petitegonewild) and his kik to respond if I was. I’ve seen her username before and knew I was interested before I even clicked it.

We get to talking and he explains his situation to me and asks for pics so she can see me. She says she’s interested and I kik her. She’s not the most talkative person so it was really hard to read if she really was interested or if she was just doing it for him. We exchange messages for a couple weeks and we try finding a good time that will work for both of us but we aren’t able to get on the same page. So things die out and nothing happens. I figure it was too good to be true. Read more »

[28M/28F] Hooking up with the Red Headed Nerd turned Hottie from High School

I went to High School with a girl named Molly. Molly was a very nice and sweet girl but she suffered from social awkwardness which is the equivalent of a curse or plague in High school. Molly was a bit shorter than me standing at about 5’5” and she was a curvy girl. She had dark red hair which she always kept long and went great with her beautiful blue green eyes. I will say she did have amazingly huge breasts all through high school. Looking back I wished I had been better friends with her in high school because she is one of those people who is just good all the way to their core.

Just before our 10 year high school reunion I connected with Molly on Facebook and we caught each other up on our busy lives in the 10 years since we last saw each other. We ended up messaging and then texting each other quite a bit and became really close friends. She was still just as sweet and caring of a person as she was in high school but she seemed more open and confident socially which was great to find out. We were both single at the time and we got to be very open with each other for example I found out she had only been with one guy and didn’t do very much. Somewhere along the way an attraction began to grow between us. Read more »

[f/m] Reddit is really good for having guys between your legs!

Hello again!
**(x-post from r/RandomActsOfMuffDive) **

Writing this message from the friendly skies up in the sky! Leaving NYC, and if was great! New York was damn good to me. Made [this post](https://www.reddit.com/r/RandomActsOfMuffDive/comments/51zozp/22_f4m_nyc/) hoping to get some success stories out of it and I Got over 150+ replies and I believe I answered everyone! (Yay) narrowed it down to 5-10 guys, and tried to see where things went. And it was a mission accomplished, was able to have two amazing success stories while in the city, it was almost 3 but this girl loves sleeping too much, and wasn’t able to wake up for early morning sex. Which I kind of regret :p

This is the story about the second NY guy, let’s call him Alex, look for the /*|*/******** to get to the gooey parts of it.

Alex messaged me early on with a success story about him, it really caught my eye as it was super sexy. His picture was also damn hot. We soon got to exchanging messages on kik and exchanged some live verification photos. We were both interested! We discussed meeting up Wednesday night or Thursday night. Read more »

[21F/26M] Breastplay

My girlfriend was living with me over the summer. We were in my room and walked behind the couch and put my hands on her shoulders and touched her hair. I told her that she had really amazing breasts and asked if I could fondle them. She told me to go ahead and I felt them up for a few minutes while I told her how fun it was to play with them and complimented how hot she was. I lifted up her shirt and squeezed her breasts quickly and then pulled it off. I asked her to leave her bra and shorts on while I undressed. Then I asked her to get up and go into the kitchen with me since there was no one home and we like the feeling of being naked or mostly naked together. When we were out in the kitchen I grabbed her breasts. She gave me a big closed mouth smile and pulled them out and asked her to leave them that way for a while. Read more »

Wanted to try Bi

I (M) was looking at some of the Reedit stories about relationships and saw one on a MMF threesome. I was intrigued by the thought of all members interacting with each other. There was a spectrum of reactions in both the male and female comments on the MM aspect. I wondered how I would react IRL, it always seemed that any interactions would be fun, and how could you expect your SO (F) to do anything you would not do. This was on my mind but my SO was not interested. When the relationship ended (for other reasons) I responded to a MM posting from another bi-curious guy and after a few emails we met. We were nervous at first, and things did not finish up completely. About a week later we ended up giving it another try and knew I had to go first or I might not go through with it again. So he lay back on the bed and I began. As he got more into it and began to move in time I found that I liked knowing I was making him move. I could feel it and when it happened I kept at it a while figuring that would make it better. By the time we finished, swallowing was not even a question. I noticed I had a quiet satisfaction that it was now inside and becoming part of me. While I have no desire to seek out further encounters, another part of me is glad I did experience it. I was surprised that I have never felt any guilt associated with that adventure. I am glad I now know I would probably go with a MMF if that would ever comes my way.

I [25M] did Red Army rape play with my girlfriend [21F]

We’ve done this multiple times, but this used to be really intense for me and honestly, it’s the only pretend rape that I can deal with. She started telling me about rape fantasies, and I was really freaked out by them and didn’t want to take part, and she pressured me and belittled me, so I made a compromise. I told her I would dress up as a Red Army soldier and have her dress up as a German girl and I would pretend to rape her. Read more »

Freak Nasty With a Stranger

I turned in my first reddit sex story a while back and it was a liberating experience. So here I go again, but obviously it’s gotta be better than the the last. No pressure!

The first story was about my first handjob – a tale that still turns me on when I think about it. To change it up, I think I’ll write about the time a couple years ago I basically had sex with a stranger because he said his dick was big.

By this time I was single, a few relationships removed from the boyfriend that I had cheated on in the previous story.

A girlfriend and I made an hour and a half drive north to a somewhat secluded town for night of live music. She had frequently listened to me moan about being horny but not wanting to just hook up for sex, so the agreement for tonight was that I would drink a little, maybe meet a guy, and she was the designated driver for returning home. Needless to say, I wouldn’t be needing a ride home from her that night. Read more »