Dating App Cougs: A Miami Night with a Shy Cougar from Brazil [MF]

This happened a few years ago, but I recently found we had each other on Facebook and tried to reconnect. It spurred some memories, most of which are NSFW and I’ll enjoy sharing them below.

I was in my 20s, had just moved to a major northern city, and was very cold and lonely at the time. Most Tinder dates were really off and girls my age seemed to care too much about things I didn’t care too much for. So I was excited to learn that my family was staying in Miami for the holidays. After buying my ticket, I changed my dating app location and started doing some early recon, but I capped the lower age range at 35.

The match was simple and straightforward. No pointless text game. I’d pick her up that Wednesday night for some drinks at Wynwood. Sounds trivial, but that was already a sign of good chemistry for me.

My most adventurous few days [FM] [FM] (long)

Almost a year ago I wrote here about my first cheating experience:

[https://www.reddit.com/r/gonewildstories/comments/a0bqgp/my_first_indiscretion_fm_cheating/](https://www.reddit.com/r/gonewildstories/comments/a0bqgp/my_first_indiscretion_fm_cheating/)

The TL;DR is that then-37-year-old, petite, professional, married Asian Good Girl me hooked up with a grad student at a conference, and I was still feeling both excited and tremendously guilty about it. Quite a lot has changed in my life since then, and maybe I’ll write more about some of that later. But for now I want to reminisce about the wildest fling I had in my single days. It was also at a conference, but when I was myself a grad student, and part of what still gets me feeling frisky every time I attend one of these things, though after getting married I never acted on it. Until last year, of course.

[M]y Jess used her hall pass this weekend for [f] again…and may be so did I!

Jess and I have a hall-pass thing, but it’s only reserved for when one of us goes on a trip/tour. Two weeks ago, Jess brought up the hall pass and asked me whether she could use it while I was at my friends’ place 2 hours away. Straight away, I was suspicious (and jealous, and of course, hard as rock lol).

I said fuck it, let’s get this hot slut get it on with whoever she wants, I mean, she’s hot as hell, and deserves all the good cock she wants/gets – so I told her, sure babe, this weekend is your hall pass. She was working the Saturday morning, but I knew she was going out with friends in the evening.

I went to my friends’ place on Friday morning, spent the night partying, and – for another story for another time – I got a handjob from this hot girl (but that’s for later).

Saturday morning I got a call from her, as she was leaving for work, telling me how she wants to get some hot cock today, all giggly. Made me even more suspicious, and I decided to trace her movements for my own perverted voyeuristic self.

Natural Beauty (mf+, teens, cons, gay, school) [Part 1/3]

*The author does not condone child abuse, this story is meant as an erotic fantasy, not real life. Please treat it as such.*

***

The idea of “natural beauty” day was to let all the kids at Jefferson Washington High School know that everyone was beautiful no matter how they looked. Tom stepped off the bus in his normal jeans and t-shirt, his blue backpack slung over one shoulder. He was normal height for a Sophomore and had shaggy black hair that he let hang down to his collar. He still had a bit of baby fat on his face and the girls all thought it was cute, yet he had only had two girlfriends last year and now both of them were with other guys.

It was quiet outside today, normally the yard was full of people walking around and talking but today the administration had asked that all students come immediately inside and go to their homerooms upon arrival. A few Juniors that weren’t old enough to drive and still rode his bus pushed past him and quickly made their way up the steps and Tom followed behind them. He was excited about “natural beauty” day, not knowing what to expect, and felt butterflies in his stomach from being anxious.

My roommate [F] and I [F] kept each other warm during a power outage.

Hey everyone, so a looooong time ago I posted a story about the time my roommate Layne walked in on me while I was twerking with my ass out. Since then I’ve had a lot of people asking me if anything every happened between us. There was one time, not too long after the twerking incident, and I wanted to share it with everyone!

Just to get everyone caught back up, here is what I and Layne are like:

I’m Brooke, I’m 20 (19 during this story) and in my junior year of college. I’m bisexual. I’m 5’5, with short-ish dark brown hair and blue eyes which I’m told are large and innocent-looking. I’m relatively pale, despite my best efforts to tan. I guess have a little of an hourglass figure. I’m only 130lbs but I have decently sized boobs with wide hips and a big, round bubble butt! My butt is my pride and joy, as you can probably tell from my username haha.

Fucking my Thai Twin Neighbours – [Asian], [BWC], [British], [English], [FFM], [big dick], [big cock], [cock worship], [rimming], [threesome], [hand job], [blow job], [pussy eating], [arse eating], [ass eating], [face sitting], [Thai], [cute], [facial], [dirty talk]

Kanya and Lawan had come to Britain with their mother, when she married a British man. They’d been in their house about five years before I moved into the house that backed onto theirs. They were now attending university but regularly came back home to relax and get work done.

Ever since we’d moved in I’d been able to see the girls showering in the bathroom and even through the frosted glass I could tell they had beautiful bodies and perfect tits. I’d been getting to know them, Kanya and Lawan, over the past few months when we were both out in our back gardens. We got friendly and soon I was heading over to hang out at their house when their parents were out.

They both turned out to be quite cheeky and brilliantly foul-mouthed! It was very easy to feel comfortable hanging out with them. We used to laugh about how their dad talked to their mum. He was so stupidly patronising to her and used to speak in broken English to her, presumably believing she would find this easy to understand. We used to love laughing at the time I overheard him in the garden saying “You know how I say I like gooseberry, size of grape?” It became a running joke.

Im a straight guy and my i cummed in my guy friends mouth [MM]

So this happened couple months ago, iv only been attracted to girls and nothing else. Not even a little bi curious. I was hanging with my friend who had a new roomate move in recently. The roomate is half thai and half white and is pretty fem.

Whenever i use to go over to my friends house, we would all hangout and i actually became friends with the roomate. One night i stopped by friends house to chill after my kickboxing class but found out he was away for the weekend with his girlfriend. So i decided to have a beer with the roomate and then woud leave after.

As me and him are having a beer he’s talking about how he hasn’t had too much succes with guys since he moved here and how hes been really horny. I told him obv i can’t help him in that department. He kinda laughed it off. I changed the subject and told him how my legs were killing me from class and he said he went to school to be a masseuse and would give me a massage if i wanted.

How sucking one dick led to sucking dicks

So after I sucked off the black guy and posted the story of reddit I ended up getting a text from a guy a hour after sucking the 1st saying “I heard you suck a mean dick. Keen to give mine a try” with a pick of another black dick. In my mind I was thinking okay he didn’t reply back but I must of done a good job if he gave this guy my number. Was I going to let him use me also. The answer was yes he was black and I wanted more so I again replied with my address and got any extra criteria. He replied back naked, blindfold with head hanging off the bed.

Interesting situation every black guy doesn’t like to be seen. So I stripped and waited with my head hanging off the end of the bed. My 2nd Guy came in and without warning put his cock on my lips I opened my mouth and he slammed his cock straight down my throat, his dick must of been the same size 7-8inches as I gag around that size. That when I hear him say balls deep my throat. “Ty was right. This bitch can take a good dicking” and with that I wanted to make my first guy proud and let him have his way pumping my throat as hard as he could I just laid there waiting for him to cum 10mins after he empties his load straight down my throat.

[MF] a friends weekend at a cottage

So a few years back my girlfriend , myself and our close mutual friends would always organize a cottage weekend together.

There was me, my girl, two couples we knew from work. But my girl had also invited her two best friends to join us.

I was 23 and my girl was 20 at the time. We had been together for 2 years at the time.

My girl was a bit of a prude but I did know her and her two best friends talked about our sex life.

One of her best friends was this incredibly sexy 5’10, petite white brunette , big blue eyes. My girl was much shorter with a similar bra size. But her friend was not only a 32D, she had a tight body and a great ass. She always wore revealing clothes and would always hint at me that she knew all about how lucky my girl was.

The first night at the cottage we were drunk playing cards against humanity when my girls best friend gets up to get a drink . As she walks back we all notice she’s wearing this satin pink g string bikini and a push up half cup bikini top.

[MF] Colleagues ex girlfriend got creampied after movies

A year ago I got my first real job. Its a nice job, nothing too hard, close to my home and colleagues are great. We are divided in a teams of five to ten people maximum for our projects. Our project leader is a great guy. Smart, funny, understanding, always ready to help, and apparently has a very, very slutty ex girlfriend.

A month ago, his longtime girlfriend left him. He was devastated. He barely ate and had no concentration for work. One day she left the apartment where they lived together and left him a message not to call her. After his million of attempts to reach her, she finally answered and told him that she no longer loves him, and that was the end of the story.

I met her at one of our company events. She was very beautiful. Skinny brunette with sky-colored eyes. When she looked at you, it would feel like she was looking straight into your soul. I didn’t pay much attention to her at the time because she was a colleagues girlfriend and some things you just don’t do.