Category: gonewildstories

[M/F] I finally had my first hook up and it was nice I think

I'm an extremely geeky and socially awkward 21 year old man. My social skills are complete garbage, but hey, fake it till you make it. I'm pretty decent looking though. I just don't know how to talk. I was bullied and picked on when I was little.

I've never really been with a woman who was completely naked. Haven't kissed a girl in over three years.

I was on Okcupid mindlessly looking for someone to love. That is the only way I meet women, through the internet. I asked this one girl out and she said sure, and I asked her where she wanted to go, but she never replied. So I said "Its totally fine if you're not interested." And guess what? She replies that she is mainly just looking to hook up right now. I say I'm down for that. I tell her I'm a virgin and that I don't want sexual intercourse. But I would like to make out and what not. She agrees to that.

So I give her my number and we text. We agree to meet TONIGHT. Read more »

Masturbating with my best friends bra and panties.

So two of my best friends are a couple me and my girlfriend know. We have known them for 3 years and we hang out all the time and just have a good time. But nothing sexual. The female friend is very attractive but there married and I would not want to hurt either one of them. Also she has fake boobs and has let me touch them. But I have not seen them. I have noticed I have started fantasizing about her more and more. I have taken a few down blouse shots when I can. Then the other day I was at there house. I went to the restroom and I saw some of her bras and panties. I picked up her panties and they smelled amazing. Then I started to get hard. I rubbed her panties all over my cock until I got precum on them. Then I took and rapped her bra around my dick and did the same. I was going to cum but I was in there a while. So I tried to put them back where they where and left. But I am not sure what to do. I would love to see her tits. But other then trying to sneak a peek or take a spy video I don't know what to do. And I would love to cum on her bra and panties.

The Long Story of My First Threesome [MFF]

This is a few years old now, but I've just discovered this subreddit, and figured it's just about the sort of thing you'd all like to hear about, so I'll share. For context, I'm currently a 33-year-old male living in Kahului, HI. Most of this story took place when I was 30.

At that time I was living with my ex. I don't just mean that I was living with the girl who is now my ex but wasn't at the time; we were exes at that time as well. I'll spare the details of how that came to be, but the important bit of the explanation is that she and I remained close friends after ending our relationship, and it was easier for us to continue on as friends and roommates than to try and find separate living at Hawaii rent rates. Read more »

The Eyes of Desire(m/f)

This happened a few years back. I was 21, young, and ready to get into the bar scene near my college. It was around this time I found myself ready to join the swingers and get lucky. But there was a problem. I had no game. I thought I couldn’t hit on a girl if I tried.

But that night, I decided not to try. I decided to just grab drinks with my friends, and have a blast. Now, to understand what a bar night was like for me, it’s important to understand who my friends are. One friend of mine had trouble with his liquor. And by trouble, I mean he’d usually cry, be crazy happy and annoy people, or just go rogue because it made sense to him. Another friend would simply sit outside while we drank and smoke. That’s it. And another friend would bring his girlfriend along and always argue with her. And by argue, I mean screaming matches.

Understand what I mean? I’d have to venture outside the usual groups. So I’d be lucky, get into a conversation or two, and dance. It was a ton of fun. But tonight, I just decided to go to the bar and just look around. This was a college bar. It was cheap, there were fights, and the owners overpriced everything. Read more »

Sex in 50 states: Ohio [M/F]

I was told i should post here, but if this isn't the place then let me know. Basically I have a long term goal I'm working on of having sex in each of the 50 states in the US. Started several years ago as kind of a joke with some friends, but now I'm trying to do it for real. Currently I'm sitting at 27 states down, 23 to go, and also have DC down. There's really only one rule, the woman (I'm straight, so only having sex with women) has to be from the state in which we're having sex. Most of these were in the summer when I have time to travel. This might sound nerdy and/or creepy but I keep a journal, which is coming in handy now. Not going to put up a story for every state, but was told I could maybe put up some memorable ones, so I'll start with the first. Read more »

I was an inconsiderate asshole towards a frumpy recent-ex-wife and got lucky.

My friend Steve is a functional alcoholic with a few close friends. On weekends if I don't have plans I join him and his friend Mara for a beer or two. Mara is married to a professional scuba diver who's usually gone for long periods of time, so she's always around.

Mara is a nice girl with soft brown eyes and always a slight smile. She is a sweet girl with genuine intentions and her husband always in mind. When we hang out, we usually skype with her husband who's usually in some off-shore hellhole. There's a running joke where I pretend Mara's real name is Maranditha, and I'm generally a punk towards her.

Last night Steve called me up and mentioned that Mara is coming over for some board games and booze, so I said right away that I'd join them. Steve mentioned that Mara's sister, Kayla, was coming over too. That's weird, I thought – I didn't know Mara had a sister.

I had a good mood when I went over to Steve's place, and said hi to them, making sure to say Maranditha to Mara's face. She introduced me to Kayla, using, and I quote "and this is that asshole who pretends not to know my name" as the first greeting. Read more »

My First Babysitter [m/f]

It wasn't planned, although I had lusted after her in my heart for several months. She was cute, of age, the girl next door, and very sweet towards my entire family. Which is what made what happen all the worse.

My family takes Black Friday very seriously. Its odd, almost like some strange bonding ritual every year. So my wife, in-laws, etc. were are ready to go last year, and they roped me into it. Samantha came over to sit for the kiddos. It was especially cold, and I wasnt feeling up to it. After the madness at Kohl's where there was almost a riot, I had enough and said I was going home. I knew they would stumble in about 7am, bleary eyed. So I went home, and found my kids asleep in front of the tv, while Samantha was messing with her phone on the couch. I went and got ready for bed. About 15min later I went into the living room to say goodnight and make sure everything was ok. Thats when I noticed Samantha was wearing a loose top and I had a clear view of her young teen tits, I could just see the outline of her nips. Hmmm, I started having dirty thoughts and drew out the conversation. Read more »

A Night to Remember [Group]

My first group experience with wife and some friends. My first attempt at writing as well:

My wife and I have been together for 12 years, when we first started dating we were just teens, fresh out of high school. as we age together we have become more sexually curious with exploring our overall boundaries. Over the years we would party with our closest friends and while as close of friends as we could be, nothing ever occurred. We would joke about threesomes and everything, share stories, explain new and exciting toys, but it never went further than the occasional tits popping out in some friendly board games. As the years progressed, my wife and I begun taking an interest in voyeurism, this definitely started with me and through time, I was able to get my wife on board. When I say over time, I am talking about two years or so. We never did anything too wild. We would have sex out in the back yard, where our next door neighbors might catch us, in public, dressing rooms, our car… Read more »

Trying something new, my first couple swap (part 2) [MFMF]

So like I said at the end of part 1, Karl and I were in the shower and still horny, and decided if Wes and Whitney were up for it, we would go for another round. We toweled off and started to head back to the living room, but when we got out there, they were nowhere to be found. We went back to the hall and heard some wet noises and light moaning from one of the rooms, and when we peeked inside, Wes and Whitney were in a 69. They were laying so I could see Whitney sucking his cock, which wasn't hard again yet but she was still going at it. She saw us standing there and said to come on in, so Karl and I didn't waste any time, we climbed up on the bed next to them and got into a 69, too. My whole body shook as his tongue licked my pussy and I took his cock in my mouth. He wasn't hard yet either, but before too long with both Whitney and I sucking, both guys got hard. Read more »

Skinny dipping with a friend[M] leads to me [F] losing my virginity – part II

This is another part of my adventure with Nick, a friend of mine. Part one can be found here

Hot and heavy bits after the

After all that happened, the rest of the camping trip was pretty much uneventful. Nick and I never needed to talk about it, but we kept it as a secret just between us. It would have been weird to let our friends know what happened, because we always thought of eachother as friends. (Maybe there were other flings behind my back though. Who knows?) I also thought it would be a one time thing, and didn't feel the need to ever bring it up. I just recorded it in my journal (is that dorky? come on, it was a spectacular night.) and proceeded to go on with my single and Nick-less life for the next week or so. Of course, I thought about the sex frequently.

Our next encounter was a movie night at Nick's. I was thankful, though concerned about whether anything would happen at all. (At this point, several months ahead, I'm happy to tell you Nick initiated this meet-up.) Excited and anticipating something more than just a movie and sleepover I wore nothing but a matching black lacy bra and skimpy panties set under my oversized tank top and short pyjama shorts. Read more »