Category: gonewildstories

How I started sharing my girlfriend with my best friend during the lock down [MFM][consensual][wholesome][sharing][trust][threesome gonne sideways][cuckold]

We play the cards we are given. This has always been my motto in life.

During my 20s, I started experiencing difficulties in maintaining an erection. After seeing a few doctors, I was diagnosed with a venous leak. This is a condition that doesn’t affect my libido at all but makes it difficult for my penis to stay erect for too long and it’s something that progresses as you age. Needless to say, this was a kick in the balls for my ego. This problem was aggravated by the fact that I had come to expect failure. Everytime I got sexual with a woman, I had that fear that my penis would fail me and so it often did. This made me start avoiding relationships altogether.

Meanwhile my best friend who is a couple of years younger than I was quite the opposite. Always the ladiesman. Everytime we went to a party he would effortlessly hook up with someone and even though he is a player at heart, he has that kind of personality that girls just love. Most of the girls he was with were perfectly being fine in being a NSA fling. I was always amazed on hoow things just turned out for him. I’ll admit that I was often a bit jealous as well. Read more »

My stepbrother fingered me [F]

After having my stepbrother watch me finger my pussy and tight asshole, I’ve been dying to have fun with him again. There’s been definite sexual tension this past week, and I finally put us both at ease. Our parents drove down to the beach to grab some local fish, leaving us at home all day. I was talking to my followers, when several suggested I go play with him, while they were gone. In the mood from already playing with my pussy earlier, I agreed and changed into my tight purple bralette and pajama shorts (letting my pussy breathe from my thongs haha), and I walked into his room, noticing he wasn’t there.

Updating my sweet followers with my disappointment, many suggested I grab my vibrator and play with myself on his bed while I wait, in hopes he’d catch me. I ran down the hall in excitement from the idea, and grabbed my toy, before walking back to his room, and getting situated on his bed. I faced my body towards the open door, and took off my shorts, dropping them to the floor. I was so horny from the thoughts of what he might do, when he sees me. I pulled my 36DD tits out my bralette, and laid back, bringing my knees to my chest. I sighed from the AC hitting my exposed pussy hehe. Read more »

I [F] sucked my bosses [M] dick at work

I fucked a lot of coworkers at one of my previous jobs. My biggest regret is that I never got to fuck my supervisor. He was my favorite to flirt with because he was a challenge. He was married and faithful, but I could tell that he used to sling a lot of casual dick and I could tell he wanted to fuck me.

I’m short and chubby, huge tits and ass and a smaller waist – like a short, thick hourglass. I’m white with gray eyes and at the time I had long, red hair. He was over 6 feet tall and looked like he had been muscular about ten years ago. He was in his late 40’s, I was in my early 20’s. He was Caribbean and had light brown skin and a slight accent.

Things didn’t get flirty until he hinted that he had heard some things about my hidden talents. I knew the guys I was fucking around with would inevitably talk so I wasn’t shocked. I asked what talents he meant and he said he heard I gave the best head. I told him the rumors were true and he laughed. I leaned in, pressing my big tits into him and asked if he wanted to see for himself. He resisted and told me he was married. I shrugged and went on my way. Read more »

My first [MFM] threesome

My first job out of college was at a mall photo studio. I was 22, short and chubby, but I got a lot of attention cause I carried most of my weight in my ass and tits. I have pale skin and had long red hair at the time. My boss was about 50, more than 6 feet tall, bald, black and married. We flirted a LOT. We both enjoyed the back and forth, but when I made it known that I was interested in more, he turned me down. He said as much as he wanted to fuck me, he couldn’t cheat on his wife. BUT he had a cousin who was “a freak” and would love me. Sounded right up my alley so I told him to set it up. Read more »

Unexpectedly, the Hottest Dance of My [F] Life With an Old Friend [M]

Let me start by saying, this isn’t a sex story, but it’s definitely sexual. I’ve been partner dancing for nearly a decade now. I’m primarily a follow. There are friends, or leads, I dance with regularly. This is a story about one of them. Let’s call him Matt.

______

Matt invited me to a blues event. I tend to shy away from these, as the crowd can be filled with all skill levels and the style lends itself to incredibly close contact. Body to body, more often than not. It’s more sensual than what I’m used to, and I prefer to know my partner. But I trust Matt.

We met up for drinks ahead of time and chilled. It felt like any other night. Easy and calm.

Once at the venue, Matt extended his hand to me – an invitation to dance. I placed mine in his and he led me to the edge of the floor.

Something I love about partner dance as a follow is the loss of control. Every so often, with a sensitive lead, I can enter into this flow state where I’m *really in my body*. Matt always knew how to draw this out of me. Read more »

[F]ucking [m]y sister in-law

Exactly two people know about this… my sister in-law, Katie, and me. I won’t say whether she was my sister in-law at the time or not – use your imagination to make the story hotter depending on your tastes – but this story actually happened.

Some backstory:
My wife is about 4 years younger than Katie. Katie is the oldest in her family and completely spoiled. Like struggles with being an adult because she has been coddled her whole life. My wife is much more independent, hotter, and had more success with men. Katie is solidly curvy, but definitely cute and has some nice large assets which I am sure many people would find attractive. People including me. I actually knew Katie before my wife. We went to school together, but this happened well after we had graduated.

My wife, Katie, and I were at a party. Katie had come with her BF at the time as well. Sometime during the night, Katie’s boyfriend left and she was hanging around my wife and I. There were drinks and some dancing and I thought that Katie was being a little flirty, but brushed it off as just the alcohol and certainly not on me in front of her sister. Read more »

How I [M] managed to hook up with the coworker that I had a crush on [F]

For context – this was a story I recently shared with a Reddit friend of mine, and she insisted that I post it here – so if it reads a little oodly you’ll know why!

So myself and DD work together. We sat next to each other for a number of months and got quite close to each other. I made her laugh a lot. There was a tension between us that we didn’t address… But anyway, I had friends over from work for a party, and we were a little touchy-feely (not in a flirty way, but just a lot of contact), but I know she had a boyfriend. I didn’t make a move.

So, I have another drinks night soon after, having my work friends over again. We get more drunk, and her and another friend of mine and me all stay in my bed. I had given her a t-shirt and shorts of mine, and my other friend stayed fully dressed, with him on my left and her on my right. Eventually, the other guy left (maybe he picked up the vibe?), and I spooned her with her holding my arm around her waist, rubbing her feet against mine… and of course we gave in to our temptation. She had actually fought with her bf that night about staying over at mine because he saw me as a bit of a threat… whoops! Read more »

Sharing my wife against my will? [MF] [M]

Sharing wife against my will? [MF] [M] With updates

Original post followed by updates. I was adding them last night but not sure people could see them.

My wife [27] and I [28] have been married almost four years. We started dating in college and got married a little while after I graduated.

She has a good sized following on Instagram and 99% of what she posts is from our workouts, whether it’s CrossFit or hiking or whatever. I will be the first to admit I married way out of my league. I will never deny that.

We have worked out at the same gym for a while now. Lots of old faces but some new ones every so often. Not a lot of people stick with CrossFit but there’s always a new person willing to try it out. On Monday, a new guy showed up. The guy is in incredible shape, and he’s a freak because of his size. He’s probably 6’5” and I’m guessing 245, but that’s a guess. He has nothing but muscle on his frame. Read more »

I [f]inally hit rock bottom when [m]essaging a guy online

Ok some of you are going to find this sad and the rest will find it sexy so strap in.

Also quick disclaimer at the start, when I say I have daddy issues, I mean I see a therapist and what we mostly talk about is my dad. I don’t fake it like a lot of girls.

So I was mildly horny so I went on an anonymous messenger and met a guy, let’s call him will.

Will started off being nice, being polite and blah blah blah until he starts asking me if I have day issues, clearly it’s a turn on for him.

I say yes, and he just flips and starts purposefully degrading me, but I’m really liking it. I send him a few photos of me (clothed) and he says I’m ugly, and the only way he’ll give me attention is if I pay him, and he sent his PayPal.

Now I’m not desperate for attention, admittedly I can’t hold down a relationship but I can definitely get myself fucked pretty regularly. But I was desperate for his attention, for his approval. So I sent him $5. Read more »

Me [M], 30, getting head from 21 yo park visitor [F], while her family was nearby.

So I volunteer on weekends at a local historic site park. I’m usually dressed in period costume (think colonial days, Revolution). There’s the main site and then a small old cabin off to the side. Anyway the girl, “J”, showed up last weekend with her family. We know each other already and had hooked up a few times when she was a freshman/sophomore in college when I worked maintenance at that school. Haven’t seen her in a year or more. I didn’t recognize her at first due to her mask, and I had never met her family. but her dad apparently is a big history buff and was asking me all kinds of questions (which was great, that’s the reason I volunteer) and she stood there quiet in short shorts and a tight top that showed off her shoulders and cleavage. I could see her smile at me and then it hit me who she was.
Her dad and mom and younger sister then went off to keep looking at stuff but she stayed behind to catch up, and actually made it clear to her family that we knew each other from the school. It was one of those rare movement when timing is perfect cause I was on my break (a full hour for lunch) and very quickly she started making it clear what she had in mind. So, we walked off to the little cabin I mentioned which has one wall facing the woods, she dropped to her knees and as a joke produced a bottle of hand sanitizer. After unbuttoning my colonial-style breeches, and giggling the whole way through she then said “hashtag covid” and began jerking me off with the sanitizer. I haven’t gotten any in almost three months and I told her I would cum quite quickly. She then put me between her lips and tied up her light brown hair and sucked me slowly for a few seconds before I shot a load into her throat. She swallowed, coughed from the mixed taste of sanitizer and cum, buttoned my pants back up , then stood up and simply said “you looked like you wanted to bang me before you recognized me so I figured I should help you out,” and kissed my cheek. We then actually caught up for real and spent the next hour talking about life. Her family were clueless.