I [M]et up with a high school [F]riend I hadn’t seen in 15 years, right after a break-up

Something magical happens when you change your relationship status on Facebook. Old (female) friends come out of nowhere to make sure you’re “doing ok”.

Becca wasn’t by any means my high school sweet heart. We traveled in overlapping social circles, but barely crossed paths during school. But we both thought the other was attractive and this led to a few random kisses and touches exchanged at random parties as we got high together. It was so very high school. But that was ages ago, and we are both functioning adults and that was a different time and a different life.

She messaged me only a few days after my status change.

Becca: *“OMG, I can’t believe you’re single, I would see your posts and always thought you two looked like the perfect couple”*

Me: *“Well, sometimes things aren’t as they appear. I’m just trying to get my new life straightened out”*

I had been with my ex (lets call her Beelzebub) for nearly 10 years. A dead bedroom and constant bickering over money (she wanted more), sex (I wanted more) and a lack of common ground (we both needed more) had eventually lead to our going separate ways.

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.

Goodbye Amish, Hello Fucking. 40s F teaches 20s Amish M virgin to fuck. Part 3 [FM]

Part One: https://www.reddit.com/r/gonewildstories/comments/d3o1n0/goodbye_amish_hello_fucking_40something_f

Part Two: https://www.reddit.com/r/gonewildstories/comments/d3yg3l/goodbye_amish_hello_fucking_40something_f_teaches

If you didn’t read the first parts, the situation is:

A young Amish (well, formerly Amish, leaving his church) man messaged me and we started talking. It slowly grew into something more risqué as he told me his fears of dating as a young twenties virgin who has never been kissed. He fantasized about having an older woman take control and teach him everything about a woman’s body and sexual pleasure.

I’m a 40-something married woman in an open marriage. I offered to teach him. I’m short, curvy with long brown hair and huge boobs and a small butt.

***

Part Three:

I was exhausted and starving. I looked at my watch and realized we had been fucking for nearly 2 straight hours.

I suggested we order room service. They had an all-day breakfast menu so I ordered pancakes and eggs and bacon and orange juice. It felt like a Saturday morning breakfast in bed as we sat together eating and talking about everything we had done so far. You couldn’t stop smiling and it was adorable. Your confidence in yourself seemed to have doubled in the 2 hours we had spent together.

My Robot Boyfriend [mf] [piv] [manbot] [robot]

“You’re a sweet, talented, hard-working young woman, Kelia. You’ve got a bright future ahead of you. Don’t let anyone derail it.”

Those were the serious, yet sincere words of Kelia Aden’s mother. She’d first heard them in junior high. It came shortly after she brought home her another straight-A report card and a letter from her guidance counselor saying that she was gifted. More than one teacher had told her that she had a great chance of getting into an Ivy League university if she maintained her current path.

It was a challenge, but Kelia always rose to the occasion. Even as she progressed into high school, getting top grades and high test scores, her mother kept belaboring that fateful message. At first, she thought she was just being an obsessive parent. Then, she suspected there might have been other motivations. That became obvious whenever cousins, aunts, uncles, and family friends saw her.

“Kelia is growing into quite the babe,” they would often say. “Pretty soon, she’ll be beating the boys back with a stick.”

Slut rebirth with [F]irst successful anal

I recently started using dating apps and a forum to fill my days with sex. Now, I’m no stranger to dating sites; I used to be on AFF for a while and then took a break but I guess now I’m back at it. I’m a curvy asian with long wavy hair, some of it bleached. 

So before this I never really got into anal coz all my encounters were not good. I had come to the conclusion that it wasn’t adding much to the sex I was having; hence not worth saying I’m open to it. But yesterday I went did it.

After work I went to meet this masseur I’ve been seeing once a fortnight. He’s asian, a little taller than I am, maybe 170cm or so. Tanned skin hair cut short, slim build. He said he runs and plays soccer.

He didn’t massage me this time. We got rinsed off and lay in the hotel bed naked. He was showing me some porn he downloaded; something about this blonde broad teasing 2 dudes into giving her DP. 

One night with Katherina – Part 15 [M+F][prostitution][anal][ass2mouth]

*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.*

***Mathis:***

I´m all too happy to give her what she wants as I grab a hold of her and begin to pound her as hard as I can. Every time my hips impact her butt it sends shockwaves through her cheeks making them jiggle enticingly. “Hmpf.” Is the only sound that escapes me whenever I prepare for another thrust.

I grab her hair with both of my hands and turn her slightly, pressing her face into a pillow instead of the backrest. I position one foot on the couch while the other remains on the floor. With every thrust her entire face is shoved across the pillow, smearing makeup and spit all over it. It´s probably ruined I think but only for a moment. I don´t care about it at all in this moment as I´m completely caught up in the rhythm of fucking Katherina´s magnificent ass.

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:***

One night with Katherina – Part 8 [M+F][prostitution][rimming][toys]

*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 moans surprised as you enter her, but then falls into a synchronous rhythm of slightly pushing back and sighing every time you force your tongue inside her.

At first the hole is repeatedly clenching up in surprise to your contact but after several strokes it remains still and open. Perhaps she is willing herself to relax. Her eyes are still closed.

As you continue Katherina lowers her front to her elbows and placed her brow on her arms on the floor.

***Mathis:***

I continue for some time lost in the rhythm of tongue fucking her ass. Pushing my tongue inside, holding it there a little, trying to swirl it around before pulling out and repeating the process. After a while I stop and get up. “Stay right there.” I request as I walk over to the suitcases and open them. I look through the gigantic assortment of toys the agency has provided us. Finally I find what I had been looking for. Some anal beads and a decent sized dildo.

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.

Wedding Tease [MF]

The sun was going down and the air was getting cool as the fairy lights above their table flicked on. Jess and Ben were sitting at a table of 8 amongst 12 other tables, all full of guests. It was Jess’ childhood best friend’s wedding – Jess hadn’t even expected to be invited, but she was glad to come have the excuse to come dress up, eat some good food, and have a night of dancing with Ben.

Ben had something different on his mind – Jess. He loved seeing her get all dressed up, wearing heels that made her legs look long and shapely, a dress hanging delicately off her shoulders and fluttering around her thighs. She was wearing bright red lipstick outlining the curves of her lips, and eyeshadow that made her eyes look an even deeper brown than normal. He couldn’t get his thoughts off of her. Sitting next to her at this table wasn’t helping things, her leg occasionally brushing against his. He longed to keep his hands under the table and just stroke her silky thighs underneath her dress.