Author: gwsth

Webcam follies [MF]

So this happened quite a few years ago.

I had dated Jessica when we were in our late teens. We split up amicably simply because we were heading down different paths in our lives. No issues, no regrets. It just “wasn’t meant to be”. But when we were together, we did have lots of sex.

Fast forward about 15 years. Mid 2000s. She’s now married. Her husband and my SO both knew about our previous relationship and had no issues. We had been over at their house for dinner a few times. The family’s computer (a desktop) was in the kitchen as she spent most of the day looking up recipes, cooking, and monitoring her son’s internet usage while doing so.

Her husband had bought her a Logitech webcam on my recommendation. He had gone away on a trip and she wanted to make a video call so they could all spend a little online time together. She got the camera hooked up, but was confused about the software he was telling her to use. (I don’t remember what it was). So I downloaded the software and started walking her through it step by step. “Ok, now hit this. You should see XYZ on the screen. Now hit this.” Read more »

Bree, Part 1. The party [MF][Long]

I had met Bree back when we were teenagers at a party hosted by a mutual friend. Angela and her then-fiance threw parties virtually every weekend, usually attended by about a dozen or so people. I had seen Bree at some of these parties but outside of knowing her as “the one with the incredible rack”, I really didn’t get to know her all that much. She was about 5’3, definitely a bit thick but not overly so. She had a smile that could light up a room, exuded confidence without coming off as overly cocky, and had a set of tits that pornstars go to plastic surgeons and pay good money for.

Shortly before this particular party, Angela and her fiancee had a huge fight after he had accused her of sleeping with half the guys in town. Now this was completely unfair to Angela as she had only made her way through a quarter of the guys in town, restrained herself by only sleeping with one of her downstairs neighbors after her fiancee had left. And there was no way she was going to stop partying just because her fiancee had gotten hung up on stupid little things like fidelity, and she spent the majority of this particular party in bed with my best friend. Read more »

I have never admitted that I stuck [m]y dick in crazy, and therefore have never told anyone how [f]ucking amazing it was. (Long)

I had met Angel and Shelly at the same time while hanging out at the mall. Shelly was far more attractive….blonde, about my height (5’4″), great tits, and looked like the standard metalhead girls of the 80s. Angel wasn’t the worst in the world. Average looking, mildly overweight. There was nothing that stood out about her one way or the other, outside of the fact that she had probably the best rack that I had ever seen. Angel was about 3 months pregnant. Her story is that the pregnancy was the result of her ex husband; she had married him and got pregnant shortly after before he ended up in jail on drug charges across the country. The pregnancy was real, but I do not know if this husband of hers even existed or if he was a figment of her imagination. Who the actual father is is beyond me. She may not even know. For the record: At the time this happened, all of us were high school seniors. Shelly and I were 18, Angel was 19. Read more »

A drunken party fight leads to an FWB relationship that may be rekindling soon….[MF]

So I was about 19 when this happened.

I used to party pretty regularly at Jack & Jill’s house. Looking back, they were probably two of the most irresponsible people I’ve ever known, but 19 year old me didn’t care. There was a party and plenty of alcohol to go around every weekend. Eventually, Jack & Jill got into a fight; Jack basically accused Jill of sleeping around on him, mostly because Jill was sleeping around on him. Jack left, but Jill had no intentions of cancelling her usual weekend party.

So I’m at the party. Jill decides to show Jack just how faithful she can be by spending the entire party in the bedroom banging my best friend. I’m sitting around after having several beers, and for the first time I start talking to Amanda. I had seen Amanda several times at previous parties, but this is the first time we really got to talking. Amanda is visibly overweight, but not morbidly so. Gorgeous eyes, a smile that could light up the room, and tits that would make a pornstar jealous. We were splitting another beer. The conversation was going great, and things were looking good. Read more »

An affair with my high school sweetheart [MF] (Long)

I’m going to start by saying that I’m not going to try to justify my thought process or my actions. I’m just telling the story as it happened. This was back in the early 90s.

Jess and I were high school sweethearts. We had dated during most of my senior year in high school. We broke up largely due to us being young and stupid because we were young and stupid teenagers. Shortly after we broke up, her family moved a few towns over. Now this was just before the internet really became a thing, before either of us had drivers licenses (I didn’t get mine until I was 20), and when calling even a couple of cities over meant huge long distance charges. Which basically meant she might as well have moved across the country since there was no practical way for me to get in contact with her. I had regretted our breakup, but there really wasn’t much I could do about it. Read more »

20 years and lots of dirty talk later…..[MF]

[So I already shared the story of my first outing with Melanie](https://www.reddit.com/r/gonewildstories/comments/bzfptc/partying_and_fighting_and_sex_oh_my_mf/) many, many years ago. We could never really get along as a couple outside of the bedroom, but I never had more sexual chemistry with a woman than I had with her. But life kicks in. We both went our separate ways, got married, had kids, got divorced, etc.

I saw Melanie’s friend request on Facebook, and my first thought was “Well that’s a name I never thought I’d hear again.” And I would find out that 20 years changes a lot of things. In this case, it was largely for the good. She still had an absolutely amazing rack; for a woman in her late 30s who had multiple children, her tits hardly sagged at all. At least, nowhere near as much as you’d think they would. Further, she had dropped a good deal of weight, and her somewhat slimmer body had accentuated her boobs just that much more. Melanie was always a very confident, aggressive woman in bed. But now she was at a whole new level. Read more »

Partying and fighting and sex, oh my! [MF]

This one is quite a long setup. I’ve marked where the sex part begins below if that’s all you’re interested in.

Melanie and I had attended several of the same parties, but hardly knew each other as we otherwise were largely in different social circles. Up until this point, she was little more than “the chubby chick with the really nice tits”. She was overweight, but not morbidly so. She had gorgeous eyes and a smile that could light up a room. But her tits…..OMG, her tits were incredible. There are some women who are overweight and have enormous boobs that are little more than useless excess squishy fat that they wouldn’t have if they were normal weight. And there are some women who have nice, firm boobs that they would retain even if they dropped the weight. Melanie was one of the latter. *(I would have further proof of this about 20 years later when we briefly hooked up again, but that’s a story I’ll share later.)* Read more »

[MF][Cheating]Slept with high school sweetheart years after we split up.

This happened many, many years ago. AOL instant messenger was all the rage, to give you an idea. I’d say this was about 1998-1999, give or take. Keep in mind that I’m not justifying our actions here…I’m just explaining what happened. And 20 years later, I still have fond memories.

Jessica and I were high school sweethearts, and ended up breaking up for reasons largely related to me being a complete idiot. We were teenagers, we’d fight over stupid shit because that’s what teenagers do, and we’d blow stupid arguments out of proportion. But this isn’t about that.

A few years after graduation, I saw her for the first time working at a shop in a mall a few towns over. I was expecting the conversation to be awkward, but we ended up chatting it up like nothing ever happened. And I quickly realized that everything that attracted us to each other the first time was still there. We quickly started to click. After that first conversation, I made excuses to conveniently show up at the mall right when she was closing. I’m sure she realized my excuses were full of shit, but she didn’t seem to care. Read more »