I 54[M] slept with my friends (19 y/o) daughter

I don’t know if I should be ashamed or proud but this happened a couple of weeks ago. One of my oldest friends lives just around the corner from me, I know his family well and watched his daughter grow up. I have to admit that in the last two years she has turned into a really beautiful woman. Blonde hair, big breasts, long legs. Anyway, her parents went away on a business trip together and I agreed to stop in on the house every couple of days to check if everything is OK. I’d knock on the door and the daughter who stayed home would let me in. The last weekend before her parents got back I went to their house, I knock on the door and no answer. I needed to go in and feed the cat so I used the spare key to unlock the door. I went in and checked around the house, I went up the stairs and as I turned the corner she was standing there with wet hair and a towel around her… I didn’t know where to look. As I stammered an apology all of a sudden the towel slipped out of her hand and fell to the floor. Her body was better than I ever imagined. Pale but tight, pink puffy nipples and a shaved vagina. Before I knew what I was doing I stepped towards her and pulled her body against mine. I kissed her hard and she kissed me back. She undressed me as we made our way to her bed room. I felt her perfect naked body against mine and we had beautiful, passionate sex. The best I’ve had in a long long time.

[FM] Just a solidly good hookup

The universe always comes through for me.
So I had a hard week, my best friend broke up with me out of the clear blue sky, and of course the best way to get over someone is ;)
Messaged someone cute and local on okcupid and we decided to meet up for a walk by the water because going anywhere indoors felt too risky covid wise.

I knew I was in the mood of a good fuck with nothing emotionally intense. But I’ve been stepping away from unattached hookups in the last few months because they were seeming unsatisfying and also I’ve been working on being able to feel more comfortable initiating touch and being able to verbalize what I want. (Grew up religious etc, long journey to unpack and work on things)

So I decided to wear a sexy surprise underneath in case something fun would happen. I’m kind of a lingerie addict. Anyways I had so much fun dancing naked in my house. Then put on a red lace bodysuit,  a vneck crop sweater so the red lace was a little peeking out, and jeans.

I [M] love overhearing sex in hotels

I can’t be the only one, but the sounds of couples going at in hotels is one of my biggest turn ons. The hottest experience I’ve had happened during the summer when I was on holiday on a well know European party island with my gf (F 28 – absolutely stunning, blonde, 5’5, big ass, small waist and perky tits).

One evening we had got back to the hotel and didn’t fuck as she was tired so just went to bed. About 20 minutes later, I heard the familiar sound of a bed creaking from the room above, then the headboard from the bed knocking against the wall. As the session continued the woman started moaning, softly at first, then louder and louder. Eventually the pounding was so hard, I thought the bed was going to come through the ceiling. During all this, my girlfriend was ‘asleep’. The next morning when the couple started up again, albeit much quieter, my girlfriend rolled her eyes…got me thinking if she was actually asleep that night.

[MF] My Girlfriend’s Mother Made Me Cum Under A Blanket The Night Before Christmas

I was hoping to share this story before Christmas, but I was too busy pretending to care about conversations with people I won’t see for another year. Being social is exhausting.

Anyway, this happened a few years ago, but I think about it every December. I had been going out with this girl (we’ll call her Stephanie) for around 10 months. We argued a lot, but had a lot of things in common, so we probably stuck it out longer than we should have. Our relationship was basically hanging by a thread when December rolled around. I think we both wanted to end things, but neither one of us wanted to do it around the holidays.

Every year, Stephanie and her entire family rent out a cabin in the woods for Christmas. She has a relatively small family. It’s just her, her sister, her mother, her grandmother and her mom’s brother and his wife. Their father lived across the country. He left them several years ago, so the connection is not a great one. He actually left her mom for another woman. He was apparently pretty wealthy and wanted someone younger.

First Posting, Tinder Hook up between me [M] and hairdresser [F] [MF}

This story is going to be my first attempt at putting a hookup story into words. If it does well, I’ll write out more of my conquests. This takes place in 2014, between the Seahawks epic overtime with vs the Packers and the heartbreaker to New England.

At the time I was 33, single and quite active on Tinder. I have a job that requires a uniform and that tends to get me a good many right swipes. I was dating around, had one girl that I saw frequently, but still was keeping my options open.

It was a Friday night/early Saturday morning around 1am, when I swiped right on this cute girl. Late 20’s, black hair, nice eyes, really nice curves/thick, tats and completely the goth/hairdresser vibe. I got a “you have a match” a couple minutes later. We’ll call her Charlotte (not real name)

We started chatting and had immediate chemistry flirting. She asked why I was up so late/etc. This lead to us exchanging numbers, and around 4am, I said “If I’d known our conversation was going to be this good, I’d have told you to come over, cuddle and have this talk in person”. She responds with “well, I’m not tired, if you’re not tired”. Game on.

[M] I made my [23F] fiancee’s roommate [22F] touch herself

a bit of context:
I am 19, my fiancee is 23. We both are in college.
you can check our posts(confessions and pics for more proof of this being real)
I will refer to my fiancee as Caroline.

Caroline lives with other 3 young women in her room. While we were chilling in bed, only one was there, in that moment. Caroline’s roommate is really chill, even told us she doesn’t mind if we fuck in front of her thanks to being so respectful towards her everytime and being a chill guy.

Well, things got nasty really quick since lights were off. My kisses were wet and full of hunger and my hands chose to be on her ass the whole time.
She couldn’t resist so she put her hand on my dick and started stroking it through the jeans.

To be honest, since being a bulk bed, I knew her roomate knew we were up to something, because it was moving, but it made everything even more exciting cause we really are desperate over making another girl horny. (read our confessions)

I 20[M] fucked my friends mom 42 [F]

Title is a bit sensationalist, sorry. Let me explain, I 20m have been fucking a friends mom (42f) for the past few weeks. I used to be friends with a dude during high school, but because of college he moved out of state and I stayed local (within 30 mins) and I haven’t really talked to him since. With that said, I started seeing his mom (she knew me) at the gym very frequently, and we started having conversations when we’d see each other. She’s a very attractive woman and I loved subtly checking her out at the gym. Our conversations started getting a bit flirtier over time, and she eventually explained that she had gotten divorced during 2020, and that she finally felt “free” as she put it. After some time of us flirting in the gym (at this point we were getting to be touchy) she finally invited me over one morning.

The morning I[M] fucked my Ex[F] 11 times, in public [Part 3]

This it the final part of my long (really long) story. I posted this yesterday, but my Reddit App was acting odd, so I’m posting it again. For the ones who’ve managed to read it all, thank you in advance! And thanks everyone who DMed me with positive feedback. If you’ve missed the previous parts:

[[Part 1]](https://www.reddit.com/r/gonewildstories/comments/rqxad8/the_morning_im_fucked_my_exf_11_times_in_public/?utm_source=share&utm_medium=web2x&context=3) & [[Part 2]](https://www.reddit.com/r/gonewildstories/comments/rogsdt/the_morning_im_fucked_my_exf_11_times_in_public/?utm_source=share&utm_medium=web2x&context=3)

Part 3 – If in a church, get on your knees and pray

We sat next to the monument for a while, recovering from the insane morning we were having. I sat on the top step with my back leaning on the monument, while she sat in the lower step between my legs, leaning against my torso.

“I can’t believe what we’ve been doing. I’ll definitely remember this day for the rest of my life” – She said.

By now, we’d fucked 5 times in just over 2 hours. Everyone says it’s all about the quality, not quantity, but guys and gals let me tell you, all of them were amazing.

“What would you’ve done if that person had kept walking towards us?”, she asked

I smiled, looked again to the sky and paused for a few seconds:

A Christmas present for [M]e 50’s from my stripper sidepiece [F] 30’s

A Christmas story from my long time affair with a stripper, stage name Sunny. She was in her 30’s then, nearing the expiration date on her stripping career. She had graduated from college, but never worked except as a stripper. Blond, 5’1″. Enchanting pale blue eyes. Submissive. Tight body . Shaved, sweet pussy. A very sexy, energetic performance every time she was on stage. She was married but bored. Had a few kids. Thinking back, I think she was on the hunt for her next husband, but that thought never crossed my mind back then. I just was in it for the thrills. I was then in my 50’s, grey hair professional. Married, grown kids. Also bored. I’ll admit it—an average cock.

We hit it off in a strip club in the Northeast, nude on stage and private lap dances with bottoms on. While the lap dances were fun, we both needed more. It eventually moved OTC to motels, my house, her house, our cars, my office, parking lots, anywhere we could slip away. She was the most sexually adventurous woman I had ever met. We had a 7 yr affair, now over as she got divorced, and got remarried.

The beginning of my [MF] sexual adventures

*** Normal guy who is told he’s good looking and this has led to some fun sexual adventures. With that said I am not perfect as it did lead me to a path of cheating at times. Though some adventures did start before I was 18 yrs old, I am only writing about those after I turned 18. ***

*** Back history***
How did this start…
Well, I never thought of myself as “popular” with the girls. I had the two or three girls each year expressed their liking of my since 1st grade. This continued on to 8th grade. It started as a boring school year. I didn’t dress the best and guess I didn’t care. Apparently how you dressed was a big thing and I failed to notice. That is until I met “N” who was a grade lower. This change my world for the good and the bad. N was in someway part of my life from high school and beyond. This Jr High romance became short lived but N will pop up from time to time in future stories so I believe it was important to mention her. Also to mention I never had done anything other than kiss N until my senior year. The main thing to know is she, N was part of that “popular” crowd. She got her hooks in me and changed the way I dressed from bargain basement to the world of popular name brand. I will go into her more later.