Category: gonewildstories

This is a continuation of my times with Jamie. For the others go to my account and you should find them pretty quick.

When I was in college I had a friend named Jamie. She was a small girl between 95-110lbs blond hair, but tall. Me and her were quick friends and sometimes more. This is one of those times.

I lived at home when I went to college, because the dorms added an extra 5000$ to my tuition and there was no way I was paying for that in the long run. My friend Jamie stayed in the dorms but she hated it.

My family would often go out if towns on the weekends to visit my sister who lives about 3 hours away. I would normally go, but eventually I got tired of the trips there and back and would have just rather stayed home, so I started telling them I had too much work to do, to be able to leave. They said they understood and would leave me home alone, so I would invite Jamie over for the weekend. Read more »

Was messaging a fellow roleplayer on r/gonewildstories when this story came out, figured I should share it.

Me! I am 6’3, have brown, shaggy but swept back hair, and at the time I had a clean, short-medium length beard. I’m not shredded by any stretch of the imagination, but I am fit and healthy. I’ve also got a fairly rich voice that women seem to enjoy as well as just have a fairly masculine aesthetic.

Back a while, I used tinder for a few months to pass the time. My luck was decent as the metropolitan area I lived in at the time wasn’t for lack of attractive college girls. I eventually matched with a girl named Sandy who had this SUPER cute, nerd aesthetic to her. Freckles, glasses, gangly but rocking it (if that makes sense?), tall, and just the best fucking smile I have ever seen. Honestly, before her, I wouldn’t have said that I had a kink for the nerd aesthetic, yet here we are. Now I had just had a ROUGH relationship that included a lot of lying and abusive behavior, so I was down for something simple finally. Sandy looked like just the thing to fill that space. Read more »

am a terrible story teller, so hope you bare with me.

couple months ago, my bf brought up that this was one of his fantasies.

I have been always self conscious about my body, but as we discussed it more, i understood his reasoning and decided to take it a but more serious.

He has done some photography work and know a female photographer who he worked with before. He reached out and luckily she agreed! and for free too! it was something that she wanted to creatively challenge, but never had an opportunity.

cutting to the day of the shoot. I was nervous as heck!! i had stayed over the night before. woke up. and he says “i don’t want to have a hard on during the shoot. It will be super embarrassing. Can we do it now before she comes?”

so… we had a quickie. a good one. we take a shower and get ready for her.

about an hour later, she arrives. we chat! she is such a sweatheart. brought coffee and timmies to ease us in and make us feel more comfortable, which totally helped. Read more »

This happened when I was 22. When the casual encounters page could still be found on craigslist. I’m now 28. I had been trying for a couple months, to find a woman who would like be my first fuck. A few close calls, but everything kept falling through. Until one day in October. I get an email, from somebody who is interested. She’s 38 years old(let’s call her Rachel), from my home town, and is turned on by the thought of taking the virginity of a much younger man. We exchange numbers pretty quickly. We’re talking through text while trimming weed. She sends me some nudes of herself. I am instantly turned on. She is incredibly hot, a milf to die for. I told her I was turned on, and my cock was now hard. She asks to see! I of course, happily oblige. Take two pictures of my cock , and send them to her. (I am working, but I’m alone in a shack, on somebody’s property, with 2-3 pounds of weed on the table in front of me.) She is impressed by my size, and how nice my cock looked. It doesn’t take long for her to ask to meet me later that night. I was in shock, I was about to be laid for for the first time. We agree on a time I’d pick her up. Read more »

I met up with an old flame a couple of weeks ago, we’re both married now and it was just catching up for a drink. I wondered if it could be more again.. but put the thought out of my mind and headed out.

We were having a great time catching up… and I was remembering how much I had enjoyed spending time with her and how damn hot she was.. and the things we used to do. After a few drinks I began to get quite turned on and I realised that our legs were rubbing under the table.. could we be picking this up again?

After having something to eat, we decided to go to another bar. We were walking close.. closer than just friends should and down a quiet street, I couldn’t resist and grabbed her and started to kiss her. She didn’t resist and soon we were making out like crazy, it was so fucking hot to be with her again. Read more »

After the first time we had sex we texted for the week after. We met up the following weekend again. We weren’t vibing like a bf/gf. It was just like this unspoken agreement that we were using each other for sex on tap. I did enjoy her company though. She was cool.

We had been sitting on the back porch just talking. After a while I asked if she wanted to go inside, aka “wanna fuck?” I went into the bathroom and grabbed a condom and the lube. She had sat on the couch in the living room. I don’t know why but we almost always fucked in the living room. On the floor, on the couch. Wherever.

She stood up and I didn’t waste much time. We kissed for a minute and she took my pants and my shirt off, I took off her hoody and her sweatpants. She was not wearing a bra, but she was wearing panties which I removed. I rubbed her pussy while she stood there kissing me and slowly jerking me off. I grabbed a handful of her hair and gently pulled her downward. Read more »