I (M27) hooked up with my girlfriends friend (F27) at a wedding [MF]

Last summer I went with my girlfriend (F28, we will call her Angela) to one of her close friends wedding. We drove up with her 2 friends (both F27 & single). My gf was in the wedding party, and one of the friends we drove up with was as well. The other girl that was not in the wedding we will call Peggy.

The wedding venue was some distance away so we would be staying overnight. As a couple, we got a private room. However the single people had to double up in rooms. This made Peggy very unhappy as she knew very few people at the wedding outside of my gf and the bride. Peggy even asked to sleep on the floor of our room, and my gf had obliged. This actually pissed me off a bit at the time as I knee Angela is much to shy and vanilla to help me turn this into a threesome, so basically I figure I have been cock blocked for this stay.

30[f] I discovered I like being in control a few years ago

Being a mistress brings me a lot of joy and pleasure. I love to be incontrol, is one of my biggest kinks and I often get wet when I see a mancraving for me and do whatever I tell him to do ;) I can be a lightmistress:demandinglight spankings, soft choking, ass play, and make you jerk your cock inso many ways that will make you get a massive load of cum for me (beinggood at tantric massage also helps I always like to surprise mysubjects;). I can also be hardcore, talk really dirty, humiliate you,put you in your place, like a good boy you are, tell you how to bustyour balls, making you eat your cum, stuff like this. I’ve gotspecialized into JOI and I love when I make men cum only with my teasingand voice. I just love being a bad bitch and get pleasure from it, Imight also act bratty, from time to time but men enjoy it :P

[MF] the time I was a milf coworkers boy toy

This happened over 10 years ago. I was around 19-20 at the time. Worked in a big warehouse during the PM-AM shift. So not many other people around and plenty of “blind spots” in the warehouse.

Was working one night and I had to touch base with the people that came in during early AM hours. One of them was this smoking hot milf around 40. I had been eye fucking her for weeks ever since I saw her.

She was average height. Long blonde hair. Small C cup tits. Curvy thick ass. She was me milf fantasy come to life.

One day her and I had to go back to one of the empty areas for something. While back there we did the job we needed to do making small talk. Obvious sexual tension in the air. I had to get passed her so I gently put my hand on her back to let her know I was passing by. When I did she turned her head around at me giving me those “fuck me eyes”. I knew right then I was gonna fuck this woman.

Bad House-Sitter! Bad Boy! Down! [MF]

I had one subject to complete my degree. It was a do-over because too much partying the first time around.

At the time I was working and studying a very manageable workload (one subject that I had done before). Unfortunately for me the subject was a year long ordeal.

Anyway, one of my bosses was going on holiday just at the time that I took leave to study for my final end of year exam. She lived close to town in a little inner-city village, lots of restaurants, pubs and coffee shops.

She approved my leave and told me she and her family were taking leave at the same time. I’d been at her place before and we had a good relationship. She asked me to house-sit and look after the family dogs. Awesome! I’d get out of my housemates’ way and be able to enjoy a little inner city cafe culture into the bargain.

The time arrived and I got the tour and instructions on how to take care of the dogs, tend to the composting and so on. My boss had pre-prepped and frozen some meals for me and her husband showed me their porn stash and given me *carte blanche* to enjoy it.

[M]y crazy night with a petite latina stripper [F] (Part 2)

[Part 1](https://www.reddit.com/r/gonewildstories/comments/t9dafx/my_crazy_night_with_a_petite_latina_stripper_f/)

For some visual reference, this girl I was with looked very similar to [Gina Valentina (NSFW)](https://i.imgur.com/FKstq2q.jpg) both in size and looks

———–

By this time in the night, I have already been with Sapphire for about an hour. There was no doubt in my mind that she knew how to dance well and that we fit well, especially physically. Even though everything up to this point was done over my jeans and her panties, I could tell her ass cheeks fit perfectly around my cock when she danced giving me the maximum amount of contact during her dances.

“Baby, I want you inside of me so badly” Sapphire whispered into my ears and then looked me in the eyes with cute pouty eyes

That was it, I was sold. “Ok let’s do it”

She grabbed my hands and we walked towards the back where the vip private rooms were

“GeekyFun00 – Can you give me some tip for the bouncer. If we tip him at the start he’ll know not to bother us”

At this point I was all in. I was going to see this through the end either extremely happy or disappointed, but I was going all the way regardless.

[F] 26 Had two orgasms back to back from anal

I started to get a little horny sometime after dinner. My husband was playing Elden Ring and I was laying on the couch browsing NSFW subs especially anal related content. I was dropping subtle hints all day about him putting it in my butt or joking about doing it myself with toys. Nothing usually comes from it and I just typically stick with vaginal penetration but I couldn’t stop thinking about it.

I waited for my 4 month old to fall asleep so I could have some alone time and jumped into the shower. Aside from my usual cleaning routine I reached for the lube and my 7 inch pink suction dildo. I’m still a little nervous doing anything related to anal and the last time I tried it I was 7 months pregnant and ridiculously horny. But if I was going to attempt anal with my husband again I want to prep myself and warm up. I’m horrified that it will be a messy process and I let it stop me from potentially having a fun experience. But not this time, I lubed up my dildo before I could over think it and stuck it to the wall of the shower. I realized I was already dripping just thinking about it so now my heart is racing with the thought of something new, I turned around and backed up to it. I felt the pressure against my entrance and pushed back a bit more, the tip popped in easily. I started moving down on the toy a little more and with a startling realization my ass was already pressed up against the wall. It went in easy, the full length of the toy was already up my ass, the pressure was amazing. I started to grind on it, first slow but once I realized it didn’t hurt I picked up pace.

My first threesome was with two of my former high school teachers! [FM]

To give you an idea of how much of a weird girl i was…..i visited my old high school after I graduated and went to college. There was a teacher who I had a crush on since, honestly, the first day of my freshman year. He was smart and cute and a good teacher and I sorta low-key obsessed over him. But nothing ever happened.

So I graduate….I go to college and come home for a break and go to my old school to visit. And of course I visit Mr. X. And we have a great talk, like we always did. And it was great to just talk to someone about school and my insecurities and my goals and all of that. And he was a great listener and it was just great. And finally he said he had to go, but would i like to have dinner that night.

The time my GF picked up a stranger from a hotel pool to suck off while I fucked her [MFM]

“You’re serious?” Kaitlyn rolled her eyes in mock disbelief. “You really want to see my give a blowjob to another guy?”

“While I fuck the ever living shit out of you, yeah,” I said challengingly, “that is you think you can get someone to agree to it.”

Kaitlyn and I were staying at the Gaylord Resort in Orlando for a conference so I could get some CLEs and we could hit up Disney and Universal. We had recently had our first threesome with Madi, and I was pushing to see if we couldn’t make some more magic happen in our hotel room.

“Oh my God, you’re such a perv!” Kaitlyn roared, but deep down she knew she wasn’t any less perverted.

“I’m just saying, if the opportunity presents itself and —“ I began.

“You’re ok with me bringing him back to our room for a quick blowie.” She said now with a hushed voice. I could tell it was making her hot to think about, which is why I love her. It was always so easy to convince her to try new things. I had just seen her cum on her best friend’s face. Twice. I knew the idea of it gave her a little thrill.

How Lady Luck changed my life [MF]

Well, longtime lurker, first time poster. For once one of my real-life exploits is relatable to the monthly prompt (more like I have some free time for once), so I thought I’d give it a shot.

The story in question takes place on my 21st birthday, well, the weekend after, when I decided to take my grandfather up on going a bit wild for once, and spending the weekend in Vegas. Completely out of the ordinary for me, what you’d describe as a quiet nerd, but I figured, what the fuck, you only turn 21 once. He paid for the room, the flight out, and gave me some mad money that didn’t all make it back to college at the end of the trip. What I failed to realize beforehand was that that particular weekend in January happened to coincide with the AVN awards…

Sex with my cousins girlfriend but now what [MF]

There was a family gathering two days ago and my cousin and his girlfriend came. The family gathering took place in my aunts house. My cousin and cousins girlfriend are 23, they have a three year old and I am 21, they just came to the states about a month ago and they have a three year old. While at the gathering my cousins girlfriend started talking to me and we actually talked for a awhile. She asked me questions about getting a job and how to make connections. I felt like I was getting interviewed with all these questions she was asking. Eventually she stared smiling and touching her hair more and playfully touching me.

Eventually it was dinner time and she immediately sat next to me. She kept asking me more questions about places to visit and if I could Introduce her to my friends because she doesn’t know anybody here. I was getting really annoyed because she wouldn’t let me talk and she just kept taking and talking. While we were eating she touched my thigh while I was drinking orange juice, I coughed a little and spilled some juice on my shirt. The table looked at me and said what was a wrong. I lied and said I choked on the juice. The table laughed and my aunt said, “I didn’t know the juice I made was that good.” I looked at my cousins girlfriend and she just giggled.