Category: gonewildstories

[FMM] [cheating] Tom comes over

Previously:
https://redd.it/6makte

tl;dr my first “real” boyfriend Jason told me he was interested in me with other guys and, in particular, my friend Tom.

I had been thinking a lot about the very intriguing blowjob I had given Jason. Or, rather, the intriguing talk during. Many different, sometimes contradictory thoughts were going through my head. Especially at school when spending time with Tom.

We still hung out, but I’m sure I was being a bit weird. My mind would drift to what Jason and I had talked about — sucking Tom off. I was still very interested in the idea. But Jason and I hadn’t talked about it since. I didn’t know if he was really interested in it or if it was the heat of the moment. Was it really ok that I was thinking about Tom that way? I had gotten myself off a few times thinking about it. Would Jason be upset or turned on that I had been making myself cum with an image of Tom in my head? Read more »

My first [MM] massage

I remember years ago I was very curious…and horny. Living in a large metro area at the time, I consulted either Craigslist or Backpage…can’t remember.

I found a man (masseuse) offering massages. By the way he worded his ad, I figured that I’d be getting a Happy Ending. I arrived at his place, he told me to disrobe and if I wanted to cover myself with a towel I could. I chose not…

Lying there on my back, honestly, I was already fucking hard with anticipation! He came back in with just his bikini shorts on. He started on my neck, shoulders, then my legs and butt…the usual. He then began talking about how a lot of men enjoy having their perineum massaged. You know, the spot between the your balls and the anal opening. He then began gently yet firmly massaging me there. OMG!!!

He then says, “Better turn over so that we can take care of things on the front side. So there I am, naked, a man in tight undies and my cock, literally bobbing up and down. Again, he does a lil around my shoulders, chest, then massages my nipples. He sees my cock bobbing again and says, “Gee, it looks like you like this.” I just moaned yes. Read more »

[M] a dick pic story

This is a 100% true story. I was working at a restaurant as a cook for a short time. I was 22 or 23 at the time and I’ve always been really quiet and shy. There was this blonde waitress that worked there that was easily one of the hottest girls working there. One day out of no where she gave me her number. I was so surprised. I was like wow a quiet shy polite nice guy like me, this never happens. We texted and flirted a bit and things seemed to be going pretty well. I got to hangout with her and I thought that we were going to end up dating. She said she didn’t want to rush things. So after a while, it seemed like she became hesitant or playing hard to get. We were still texting and flirting. So I got really confident and I said, you know I’ve been told in the past that I’ve got it going on down there. She said oh yeah? With a ;) and I was like yeah maybe I could show you. She said oh wow. So confident. So I asked id she wanted to see some pics. She said yes. So I sent her dick pics. She said oh wow you have a big penis. A few days went past and she didn’t really text me and I was off work. Well when I went back to work as soon as I walked in people would make eye contact and I knew something was up. Everything seemed weird. Finally one of the loud and voicterous waitors came in and screamed “Thats my man right there LONG DONG” I was the biggest joke of the restaurant and for the remaining time I worked there and even to this day my nickname there is Long Dong. In fact people there didn’t know my real name or they just called me dong. I’m a quiet and shy guy and I didn’t think anything of sending dick pics, I thought of it as flirting. She showed everyone and expressed concerns about not being able to or wanting to “take that”. A month later she dated another guy that started working there and they have been together for 3 years. I ended up meeting another waitress there that I dated for a year, but it was a really odd time in my life. People even treated me bad like I was a pervert or a sex offender even though it was consensual flirting. I guess the lesson is to be careful when sending nudes.

Post workout pounding for my friend’s sister [MF]

Hello all I’m back with another story involving My friend Chris’ sister Stacy after we had a somewhat flirty workout session at the gym. It had been a month or so since my [“house warming” ](https://www.reddit.com/r/gonewildstories/comments/6kuseb/house_warming_fuck_with_my_friends_slutty_sister/?st=J5GDCO1G&sh=8bbcf062) and Stacy and I had been hooking up fairly regularly.

Stacy and I had just finished getting a pretty decent workout in and between my workout and her outfit there was definitely some kind of pump. She was wearing a black pair of mesh leggings and pretty much a sports bra, sometimes I think it might be a little too small for her but at the same time her legs and ass look amazing in it. She was well aware of the fact you could see her ass and thong through the leggings when she bent over and she made sure I was watching every time.

By the time we had gotten back to my apartment neither of us could keep our hands off each other, we rushed up to my door almost falling on top of each other as the door opened. As soon as we got inside I picked her up and pushed her against the door. Read more »

[TM] My first time sucking a D

This happened like 2 weeks ago, enjoy. I always had some interest for guys, transgenders too, I’m not openly gay or bi.

Well… the deal is everytime I get stoned I get really super horny and gay too lol, like sometimes I start just googling some trans escorts in the web and messaging them. I was really stoned and horny that day, and I had this transgender’s escort, that I already messaged days ago,(pre operation) number on my phone, messaged her and started talking for a while, I was really near her apartment so it was the time for it. I was nervous as fuck, running out of battery so had to make a decision asap. It was either call my uber or go to the escort’s apartment, have fun and charge my phone there. I chose the second option so I called her, she gave me the exact direction and I went as fast as I can, she let me in and sht she was so damn hot, her tits were so soft and her ass was firm. I told her it was my first time and I didn’t want to have anal sex, just oral, massage and idk, I was stoned af LOL. Read more »

My college roommate joins me for a threesome. [MFF]

So here is a little story about my college roommate Samantha. She was 5’4 125lbs 34DD long blonde hair and killer curves and she was an extremely open person when it came to sex. So, needless to say she and I had a lot of fun together.

We met freshman year and got along with each other right away. We had a couple classes together and found ourselves hanging out a lot. One day we were talking and she just groaned and announced that she needed to get laid. I laughed and asked her about her boyfriend who went to another school a couple hours away. She said that she needed something closer and ASAP! Then she looked at me and simply asked if I ate pussy. This was in the student center, by the way. Needless to say, we were back in her room 10 minutes later.

We became roommates sophomore year, and our room became the nudist room fairly quickly. Everyone was welcome, but everyone had to get naked. And group sex was very common in that room. Read more »

[MF] No extras at the strip club

A little while back I was on a work trip to a small city with a large state university and a few little tech companies. I arrived late the first night and while driving around looking for a place to eat I saw a strip club. Traveling alone and not knowing anyone in the city other than the people at the company I was visiting, I thought it might be fun to checkout the club sometime during the trip.

Back at my hotel I looked up the club online and found some sites with customer reviews. The reviews all described the place as having cute and friendly dancers. A few described them as college girls, and all said extras were never offered or provided. While I would enjoy getting blown by a stripper as much as the next guy, not getting extras wasn’t a deal breaker. I like spending time with cute and friendly women, cute and friendly women getting naked for my entertainment is even better.
The second night I went out to eat with some of the people I was working with then out for drinks and back to my hotel. But the third night I was on my own so after some steak I dropped into the club to check it out. Read more »

[MF] The Drew Chronicles, Part 3: Descent

[Part 1: Discovery](https://www.reddit.com/r/gonewildstories/comments/6nel4x/mf_the_drew_chronicles_part_1_discovery/)

[Part 2: Dalliance](https://www.reddit.com/r/gonewildstories/comments/6npy7g/mf_the_drew_chronicles_part_2_dalliance/)

—

It truly didn’t take long for the tension between Drew and I to reach a boiling point. We continued to text and tease each other throughout the next week. We took every opportunity to lay hands on one another. Whenever Drew was sure no one was looking, her hand would find my bulge and give a squeeze; whenever I was sure no one was watching, my hand would cup her ass or tit.

It became our little version of the Penis Game, that junior-high distraction that saw kids gradually say the word “penis” louder and louder, trying to be the one that could say it loudest and clearest without getting in trouble. Drew and I kept fondling each other and teasing, until we couldn’t take it anymore: The night of the homecoming football game.

In small town Texas, high school football is religion. Homecoming was an enormous production, with all the pomp and circumstance of a professional game. This year, our opponent was to be our most hated rival, a team from a town just across the interstate. Whenever we clashed, the atmosphere was electric, and it was doubly so for homecoming. It was as if the whole town went crazy for one night. Read more »

[mf] I got to fuck my coworker!! A lot! Part 2

Hey guys!! I hope you are enjoying the story!! Moving on!!

I go through the normal work day doing teacher stuff… Pretending like I didn’t know what was coming later… Fast-forward…

The final day of school has ended and my room is ready to go!! Then I hear a knock at my door… I already know it’s Chris… I hadn’t seen her today so I was floored to see her in yoga pants and a tight t-shirt (she had probably changed to do some work in her room)… I invite her in and lay her down on a mat (brought for this specific purpose) and immediately begin her massage… She moans a bit as I decide to go under her shirt… In my head I’m thinking “we’ll maybe this will be a normal massage…” then I ask, “is there a spot I should be working on?” and she tells me that her thighs are tight “especially under my butt” she says… Read more »

[MF] Celebrating a divorce on a business trip (long)

This happened a few years back but in light of my last confession I wanted to tell this story as well. Every you read is 100% true!

The Background:
I was on a business trip in Chicago a few years ago on my own and was staying at the Crowne Plaza for 2 weeks. On my second night there I was pretty bored and decided to browse this app known as Whisper. It’s an anonymous app where you post random confessions and secrets. Its anonymous but you have the ability to message people posting secrets and even exchanging pictures. Anywho, I saw a whisper from a girl (Nicole) that said something along the lines of “who wants to celebrate”. I decided to message her back and said, what are we celebrating. To which she replied saying she just got divorced!

The lead up:
So we continue to chat on this app, still don’t know what either of us look like but we’re flirting hard. I gather the courage to ask Nicole if she wants to come over and pop a bottle of champagne and really let her sluttiness loose and surprisingly she said yes, but first we need to exchange pictures so we’re not surprised.she sends me a picture of her and wow was she absolutely stunning. She was in her late twenties, slight freckles, pixie cut hair and the cutest smile. She joked that I won’t be able to pull her hair since it was too short and I responded accepting that challenge. Read more »