A very sneaky fingering [MF]

I met Juliana at my favorite pub. My friends and I were playing pool. Badly. But generally minding our own business. When suddenly she came to introduce herself while handing me a pint and her phone number.

Now, I am definitely not what I consider a handsome guy and I’ve never been approached by another girl this way before. I was genuinely like a deer caught in headlights. Nothing much happened that night other than me buying her a drink as well. After that evening we texted a bit, sexted more and we ended up spending the night together not long after our first meetup. She had incredible red hair, long and curly. Blueish green eyes, and a lovely curvy body. She was insatiable and came very easily. A perfect combination!

One evening, another couple came over to watch some DVD’s with us at my apartment (yes, this was many years ago). I cant even remember what we watched but it was a cold evening and we were all under blankets on separate couches in the dim room. Juliana laid on her back with her legs over my lap and promptly shoved my hand down the front of her jeans. No panties, shaven and VERY wet…

[M]y third time fucking a married woman. While her husband slept in the next room.

When in my twenties all my friends were getting married and I wasn’t having any luck with love. I got cynical about relationships and stopped respecting them. I fucked a college friend’s wife–more than once (https://www.reddit.com/r/gonewildstories/comments/bfdcac/m_fucked_my_married_college_friend_while_her). I fucked a woman I met online who was engaged and looking to get in one last fling (https://www.reddit.com/r/SluttyConfessions/comments/bcdkm8/i_fucked_his_fiancé_then_i_kept_doing_it/.

Desi was the third woman in a relationship that I fucked. I met her on the kind of crappy free hookup site that existed in a world before tinder. She was kind of a train wreck. She was younger than me, had been a stripper at one point, had a kid with one guy, and was married to another guy. They were getting divorced, but both of them were so broke that they couldn’t get their own place, so they still lived together in different rooms of the same apartment. He had the bedroom. She slept in the living room.

But she was attractive. And really funny in an irreverent way that I appreciated. And we clicked talking about indie and classic rock bands. And I was still relatively new to the area and lonely. All of that is rationalizing, I know. But I’m ok with that.

The Tinder Match that would lead to the best semi public blowjob [MF]

Hi Guys,

Long time reader first time poster. I’ve read a lot of amazing posts of previous re-collections and I thought why not share mine.

I thought I joined Tinder when all the girls seeking once off fun had already left and everyone was after a relationship. That mentality definitely changed when I matched with Tina. Now at the time I was 28 and although some may consider me handsome I was and still am to this day a bit of a bigger guy but I’d like to think I have a sense of personality.

Tina’s profile had not a lot in it aside from two face photos and an intro noting she had curves not for the faint-hearted. I quickly introduced myself and soon it was apparent I had stumbled across a really cool girl that had a nice personality although you could definitely tell she was only 24. Within half an hour, our phone numbers had been exchanged and whilst we both were looking for work, we had agreed to meet up the next day for a drink.

He was such a cute girl (Part 3) [MM] [Crossdresser]

I was standing alone in the living room feeling pretty good with myself. I had finished my glass of milk, effects of alcohol from the party were gradually vanishing and I just had the best blowjob of my life. I was almost sober now, my balls were empty and my cock was under control, when suddenly reality hit me hard: I just had my dick sucked by a guy. More precisely, I just had my dick sucked by the little brother of the girl I liked. And now he was waiting for me upstairs after I promised I’d fuck him! Jesus Christ what the fuck was I thinking? I mean I could live with the blowjob it could be a single drunk mistake in a single drunk night. But to fuck a guy in the ass while I’m mostly sober? Nope! Not gonna happen! I went upstairs determined to offer my apologies to Christian before sending him home.

He was such a cute girl (Part 3) [MM]

[https://www.reddit.com/r/gonewildstories/comments/d3ucpd/he_was_such_a_cute_girl_part_1_mm/](https://www.reddit.com/r/gonewildstories/comments/d3ucpd/he_was_such_a_cute_girl_part_1_mm/)

[https://www.reddit.com/r/gonewildstories/comments/d3yjqu/he_was_such_a_cute_girl_part_2_mm/](https://www.reddit.com/r/gonewildstories/comments/d3yjqu/he_was_such_a_cute_girl_part_2_mm/)

I was standing alone in the living room feeling pretty good with myself. I had finished my glass of milk, effects of alcohol from the party were gradually vanishing and I just had the best blowjob of my life. I was almost sober now, my balls were empty and my cock was under control, when suddenly reality hit me hard: I just had my dick sucked by a guy. More precisely, I just had my dick sucked by the little brother of the girl I liked. And now he was waiting for me upstairs after I promised I’d fuck him! Jesus Christ what the fuck was I thinking? I mean I could live with the blowjob it could be a single drunk mistake in a single drunk night. But to fuck a guy in the ass while I’m mostly sober? Nope! Not gonna happen! I went upstairs determined to offer my apologies to Christian before sending him home.

My first experience [MF][semi-public]

Some people might put me down as a “late bloomer” and I would have to say the reason is partially not attempting for experience, partially not desiring. But there did come a point where I realized I wanted some.

The college I went to after high school was very specialized, to the point where most of us all went through the same classes at the same time. Every time we would finish a class, we would have a party. I had a few drinks in me, and so had “Lizzie”. Lizzie was this black, big boobed, big sized lady around the same age as me. We had both decided to stay the night, and with some egging on, she had chosen to sleep next to me on the living room couch.

I Hooked Up With [M]y Ex-Girlfriends [F]riend

A couple of years ago, I was in a weird spot romantically. I had dated this girl for about 3 years and it took me a while to fully get over her. While we were dating, I had become very close with her family and her friends, to the point where I could go to her house and hang out as if it were my own family even if she wasn’t around. Her friends had become my friends (guys and girls) and I would hang out them even if she was not with us.

When we broke up, I, of course, didn’t hang out at her house anymore, but I was still pretty close friends with her sister and their friends. There were no hard feelings about any of it. It wasn’t like we had a custody hearing over who got which friends.

By the time that this story happened, my ex and I had been split up for maybe a year, but I still felt like it wasn’t over (it was) and I had already hooked up with one of her other friends by this point and felt bad about it (I’ll tell that story another time). This time though, it happened so unexpectedly, I barely even had time to process what was happening. So enough backstory, let’s just jump into it.

One night with Katherina – Part 13 [M+F][prostitution][anal]

*This story is the result of a long term roleplay exchange through* r/dirtypenpals

*It features Mathis (u/lmczpn) in first person ordering and enjoying a prostitute, Katherina (u/aurora_w), who is competent and experienced in the anal arts, but touches on some other kinks along the way.*

***Katherina:***

She nods “Yes baby…I want you to fuck me. Gimme that cock of yours. I want to feel it deep inside me!”

During the kissing she would suck on your tongue, greedy for more in her mouth.

***Mathis:***

After her words of encouragement I go in for another deep kiss, giving her as much tongue as she wants. While our mouth are entwined she can feel a smile spreading across my lips. I´m feeling extraordinary lucky as I push my cock right back into her tight asshole.

My moans are muffled by her mouth on mine and her greedy sucking on my tongue, almost like she was giving a blowjob. I settle on a steady rhythm as I pull out and thrust back into her.

***Katherina:***

My very first blowjob and one of my best sexual experiences [FM]

I’ve been reading this sub for a while and thought I’d actually make a post because as it happens my very first sexual experience was at a wedding (well, just before).

This happened a few years ago now. It was the night before my sisters wedding. I live with my parents, who also had the grooms family staying over for the wedding.
His parents were sleeping in the living room downstairs, whilst his brother was in one of the guest rooms. His brother was around my age. I was 18 and he was 20. He was pretty hot and I’ve fantasised about him a few times, but I’m far too shy to do anything about it. Besides he had a girlfriend. I was still a virgin at this point as well.

He was such a cute girl (Part 2) [MM]

[https://www.reddit.com/r/gonewildstories/comments/d3ucpd/he_was_such_a_cute_girl_part_1_mm/](https://www.reddit.com/r/gonewildstories/comments/d3ucpd/he_was_such_a_cute_girl_part_1_mm/)

‘So… would you fuck me?’. I still didn’t know what to say. Or maybe I did. Or maybe it was just another stupid joke by the guys. A weird one I must say. As I tried to figure out what the fuck was happening I couldn’t help thinking that the girl in front of me would have been absolutely gorgeous – if I hadn’t known it was Christian! She had the cutest petite figure, long lean legs underlined by those sexy denim shorts, a surprisingly slim waist, smooth tanned skin and most of all the same beautiful face as his sister, with sexy lips and sparkling brown eyes. Think the cute teen type, maybe Emma Watson or Lily Collins… yeah I know… I was thinking of all kind of random stuff as Christian moved a step closer to me and gently repeated the question: ‘Would you fuck me?’.