Category: gonewildstories

[MF] my naughty thanksgiving

I’m tall, fit and and blessed below. I do well on dating apps and I’ve been telling my naughty hookup stories.

Enjoy!

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Thanksgiving hookup

This happened when I was M29. My family decided to do a destination thanksgiving. Rented an air b n b. It’s the Friday after thanksgiving. Family time and drinks occurred. Everyone was in bed…
Laying in bed, tipsy from red wine, I start mindlessly swiping and match 27F. White blonde with light beige skin. Her tits were round and full. 5’6. Athletic build (she does her squats 🍑)

We chat. I find out she’s from out of town too with her family. Staying at a hotel less than a mile from me… I send an insinuating message about how we should make a hot memory before we return to our normal lives. She sends back a picture of her tits from the ladies room at the hotel bar

“Night cap?” She sent with the pic. Read more »

My GF Exposed [M]

Okay so long story short I was texting my homeboy that I knew from childhood about some stuff I got into and I had pictures to show him so they were scattered in my phone so I selected multiple of them to send. Well come to find out I accidentally attached a picture of my gf(22) of her being arched in doggy position from the back in a thong that I didn’t realize I sent him by accident until he texted me and said who is this? I was so shocked and embarrassed that I sent it. I told him I didn’t mean to send it and that it was my girl and told him to not say anything about it. He starts to tell me congratulations and that she has a nice ass and that I’m lucky and that he didn’t know she was that curvy and what not.

[FM] I, a lifelong lesbian, had sex with a man and realized I’m straight leaning bi

I almost can’t believe it. At first it felt like a betrayal and like my identity was crashing down but now I accept it. Having sex with men feels so right. It feels so right to get on my knees and wrap my lips around his dick. Getting so wet as he tells me I’m a good girl and how I’m sucking his dick so good. Moaning in doggy as he drills me so good a dildo will never cut it for me ever again. I’ve always been butch and masc but the sex makes me feel so feminine. Makes me want to look and act feminine. It feels so good to sink into submissive bliss and have a big strong guy have his way with me. Feeling so tiny and weak and losing control of my body as he uses me. And god, it feels so good when he cums and pushes himself deep, and his dick pulsates inside me. I get it now. I used to be appalled at the idea of having sex with men and now all the layers of repression are falling in a mix of shame and pleasure. No woman has ever made me this wet. No woman has ever made me orgasm this hard. I can safely say I’m bi and honestly at this point I may be leaning straight because I don’t even think about girls anymore. Could just be the excitement of discovering dick, who knows.

[MF] Trick or Treat

8 years ago on Halloween, I stayed in. I was in the middle of a home workout when I heard the doorbell.

I [19M] opened the door to a cute neighbour [18F]. Cutest smile, kind, dark eyes, long, shiny, black hair. I had seen her a few times, bumped into her a couple other.
I suddenly realised it’s kind of inappropriate to be this sweaty and shirtless. She has her little sister by the hand, they’re asking for sweets.

I bring them some chocolate and ask my neighbour her name. Monica. Cute. I crouched to give the little girl another chocolate and fake whispered “don’t tell Monica.” Smiles all over. Nice. We say goodbye and she mentions how she should knock on my door more often.

I finished my workout and went on to take a bath. Fully intending to have a good masturbation session. When I hear the doorbell again.

She’s back with 2 bottles of wine. She essentially invites herself in and waits for me to finish my bath.

Eventually we started drinking and playing the film. This led to as touching each others arms, waist.. Our faces closer together but facing the TV. Read more »

[F] First time (41F) actually cheating

Okay, so I’ve been having some fun unleashing myself on Reddit today. Someone I’ve been chatting with challenged me to write this story and I only have 10 minutes before the kids get home. So here it goes!

Since that cuckish hookup hubby had me do a few years ago, I’ve had many encounters with other guys, young and old! Regardless if it is considered the permanent hall pass or cheating, it doesn’t matter to me. I enjoy it shamelessly.

I was at the mall and stopped at the food court for lunch. A decent looking guy asked to join me at the table and I accepted. He isn’t HOT, just a decent looking average married guy; very non-threatening. We chatted enough that we ended up exchanging full names and he asked if I was on any social media. We parted ways and that was it for the day. Until later that night I saw a friend request from him.

Skipping ahead through a few weeks of flirty chat and all the emotional baggage of cheating for the first time…. I ultimately decided I will fuck this man. Hubby unleashed a beast that couldn’t stay dormant any longer. Read more »

[MF] “Leave your door open and be naked. I want to go down on your before you go for drinks with the girls”

A few years ago I had a 26yo FWB in the town I was travelling to regularly. I was 42 at the time, and still couldn’t believe a woman as attractive as her was into me. I’m confident enough to say I’m a good-looking older man, and I know I’ve got a great cock, but this girl was GORGEOUS to me.

Fortunately, the first time we hooked up was amazing. She even stopped to ask “how the fuck did you do that?” when we finished, and followed it up with “I guess what they say about older men is true…”

She was incredible to look at. About 5’6, around 125lbs, a former cheerleader with a full B-cup, a toned stomach and a perky ass. I can remember her walking back from the restroom naked in my hotel room one time and telling her “you better not ever get work done… your body is perfectly proportioned.” Even thinking about her now I started to swell.

We had a fun relationship. I think if I lived in her city we would have dated, but since I didn’t we kept it very casual. I gave her freedom to do whatever, but she usually dropped some evening plans to meet up with me when I was in town. Read more »

[F] 33 – I got offered to be a pornstar

I (F33) work as a barista in one of the hotspots where casting directors and producers frequent in SFV. This man (Let’s call him Mr.X) is a regular to our bar. He was in his late 30’s, tall, handsome, always dressed up, very charming and seemed like a proper gentleman. Always made sure to shower me with compliments and some harmless flirting and not to forget checked out my tits (he thought he was being sneaky lol) which I did not have a problem with. After couple months, he asked me out, I was interested and we set a date. The date was great, we both made it clear we were not looking for relationships but some fun. One thing led to another and eventually ended up fucking at his place. I left later that night after multiple sessions and it was amazing. I spotted cameras and lighting at his place which seemed very professional but didn’t look too much into it as he mentioned he was producer for some studio in LA. Read more »

[MF] A very private after graduation party

This must be one of my most private stories, although technically nothing wrong happened.

A few years ago, in my first year of teaching, i was, kind of, having an internship in a high school (only year i taught HS also) and got a senior class, where were this girl who was already 18yo. I don’t know if it was for not having that “minor tag” or for me being the youngest teacher in that school by far, or both, but she loved to flirt with me at any chance she had. Anyway for a few different reasons and particularly being my first year i sure as hell did everything i could to avoid to even go correspond in the slightest. I would joke with her to a certain point but make sure the line wouldn’t be crossed. Read more »

I 33[m] my first bi experience

A few years ago I was curious about sucking cock. I’ve tried it a few time but couldn’t get into it. So, one night when my.wofe was dog sitting her parents dogs, I was buzzed and horny. I got on grinder and invited a guy over. We sucked each other but he finished first and left. Still horny and wanting more I got another guy to come over and we both finished. It was so hot. Ever since then I like sucking cock. I’d love to suck cock with a girl or my wife but she is not into that sort of thing

My wife and I [MF] spent the weekend with another couple [MF] and had an accidental night time mix-up.

Last year, my wife, Lily, and I were invited by another couple to stay in their family cabin in rural Michigan. The couple, Alice and Robert, had their first child about 18 months prior and were taking their first vacation since. Lily and I were in the same boat at 15 months, and desperately needed some time away to recharge.

The vacation was fairly standard as far as cabin trips go. We swam in the small lake that the cabin sat on, grilled food out on the deck, and played some drinking games off of a makeshift saw horse/plywood table. It’s important to note that neither couple had been drinking much for the past few years, especially the moms since they both had primarily breastfed. The drinks were hitting harder than usual, but we kept foolishly drinking like we were back in college.
Somewhere along the line of the night, Robert broke out some edible gummies and offered them to everyone. Considering how drunk everyone was, we should’ve said no, but we were still in party mode. We threw our gummies back and went back to playing more drinking games. Roughly two hours later, the high started to kick in. I rode it the best I could, but the combination of the gummy and whiskey put me on my ass. Read more »