The Eighth Wonder of Reddit [MF]

This post is about Caitlin, the eighth Redditor I’ve hooked up with. It also details three encounters we’ve had, so you fine folks get a three-for-one. That’s the kinda guy I am.

**About me**

You can skip if you’ve read my other posts. If not, here’s a verbal snapshot of myself: 28 yo 6-ft, 195 lbs. Gym-goer, but average shape. I’ve lost 12 pounds since March though (woot woot!) Brown hair, (usually) green eyes. I’m hit on quite a bit, which is flattering. Though I do keep my slutty side private, and most friends would have no idea the sort of debauchery I’ve gotten into. Since college I’ve gone from one long relationship to the next. The most recent was an engagement that ended and finally found me embracing the bachelor life. I’ve always had an extremely high sex drive, but being antisocial found myself on Reddit as opposed to a hookup app, or at a bar.

I’ve recently been referred to (I choose to believe lovingly) as a fuckboy. I’m not a fan of the term, but there’s a point where you have to accept it. So sure: I am. I don’t like the word “bull” either, but I love fucking other fellas’ SO’s. So I guess I’m that too.

[MF] Stalls

“Hi, yes, my name is Katherine Bennett — I have a 4:15 to see Jess.”

“Of course, Ms. Bennett. Right this way. Jess is just wrapping with another client. May I offer you anything? Tea, juice, a sparkling water?”

“Oh, nothing for me, thanks. Could you please let Jess know I’m in a bit of a rush? I’m meeting my fiancee in Marylebone, and need to be on my way if I’m to make it on time.”

“Certainly Ms Bennett, thank you so much for your patience, I’m certain she’ll just be along.”

“Thank you.”

I hate to be the posh demanding bridezilla — especially as a result of my own poor planning — but if they’ll accommodate me out of my own mistakes, I might as well take advantage. I’m certain Pippa would understand, even though she’s not about today. Hopefully no one says anything to her; I’d hate her to think me a bitch. She’s a sweetheart, and it really is a lovely shop.

“Kate! It’s so good to see you again. Ready for the final-final-final?”

MySexualConfessions[F] – my real sex scenes.

I decided I will group my confessions from now on just to keep track on them.

[[ For who doesn’t know, I made an account yesterday just to write down all my real and untold sexual experiences. I’ve been through a lot of kinky/messy/embarassing/sexy moments and I could never share them with anyone. I decided to better write them down in here and share them with strangers because I will never talk about it in real life.

Stories will not necessarily be related to each other. They can be different sex miments from different times. Each partner that I had will be named – I will be using initials for their names if necessary. Nothing is fake, they are all my real stories – otherwise I wouldn’t waste time to type imaginary things-the internet is full of fake stories. Thank you for reading this. ]]

Note: I am writing now from my phone so mistakes be forgiven.

Note 2: I will identify myself as A, my ex as J. Other people will be named through the story if necessary.

Unintended sexual escalation [MF]

So a few weeks ago, I [wrote about my wife and I turning a routine visit from a friend into our first threesome.](https://www.reddit.com/r/gonewildstories/comments/6rnpfu/and_the_guest_makes_three_mff/?utm_content=title&utm_medium=user&utm_source=reddit&utm_name=frontpage) I had a few people PM me for a few more details and encouraged me to tell a few stories from my single college days.

I thought back on if I actually had any worthwhile stories to tell, and a couple came to mind. I suppose I’ll write them and let the upvotes/downvotes do the telling.

My freshman year of college, I made one of my best friends of my life. Samantha and I hit it off from the start. I admit I had an outstanding crush on her initially, but her having the whole “boyfriend from back home” really friendzoned me quick. Which I reluctantly accepted.

We remained friends and did tons together; partying, studying, concerts, etc. She became a great friend of my entire friend group, or I guess it really turned into our friend group by our junior year. We had an apartment just off of campus, and she lived in one on the other side of town. Often she’d crash on our couch after long nights or if she had an early class. She really just morphed into the fourth roommate.

My boyfriend [24M] and I [25F] had an incredible Cali sex vacation thanks to our AirBnb host couple [22F and 28M] [Group] [Public]

Hey!
This is a continuation of my post from r/nsfwiama. Basically, my boyfriend and I had a crazy AirBnb experience. In answering the AMA questions, I ended up writing these two longer stories and someone suggested I post them here. I also wrote out the third best story for this post. I will be adding more as soon as I have the time to write them all out. Enjoy!

Part 1:

The whole thing got started partially because the host couple were just so attractive. For the first 2 days, my boyfriend and I kept making half-jokes / half-serious remarks about how sexy they were. It was a private room, so we all shared the same bathroom. I woke up super early one morning and wanted to take a shower, but the woman (for fun’s sake, I’ll call her Heather) was already in the shower, and she definitely left the door open for either my bf or I would see. Historically, I’m not into other woman sexually (like, I can recognize when someone is hot or not, but I don’t want to have sex with them), but seeing her naked got me surprisingly excited. I don’t think she saw me, so I went back into the bedroom to wake up my bf (Mark) and tell him. Of course, he then got super excited at the prospect of her leaving the door open on purpose. But, also, he was like, she could have just forgot to close it and assumed we would be asleep for a few more hours.

Playing from a distance [F], [M], [public]

A vendor had invited me to a baseball game. I was going to be one of twenty or so guests at PNC Park, a park that I had caught a game or two in the past. I would have maybe five minutes of face time with the vendor and then I would be able to either make small talk with some professional and press colleagues or catch a decent game.

Pittsburgh was a city that I had visited a few times and I had gotten to know it well enough. I could find the ballpark from my downtown hotel and I knew where the good pancakes are located. And since I first posted in this sub-reddit, I also picked up a friend from the area. Monica had PM’ed me and we bounced back and forth. She had fantasies of giving up control and I had the ability to give her ways to more fully live her life. This was not a daily banter, but an occasional e-mail exchange. She made me smile and I evidently improved her orgasms. That was, in my opinion, a fair trade.

My First time as a Dominatrix [Group]

I am a tall pale girl with short red hair, right at 6′ I play plenty of sports and manage to keep any weight off, sadly my tits suffer from my excessive exercise and are fairly small (*not always a bad thing*) especially when running! But who cares about all that, time to get into the story!

I was 22, it was a summer while I was in college I spent the time to save up money for rent during the school year. I was working two part-time jobs while being a live-in Nannie, I picked up the kids from school and made sure they did their homework, for a single well off woman lets call her Jessica. She had just gone through a divorce, and based on the house she had been on the winning side. I got to stay in the house for free, while taking care of the kids – it was a great way to save up cash, but left me with almost no personal time, I slept in the same room as the daughter and she was a light sleeper, so often I would only really catch a break to get off in the shower and even then I would get interrupted by an upset child hammering on the door.

The Craziest New Years Eve [mf]

The craziest New Years Eve [mf]

2005 was not the greatest year for me as a “moral” human being. I got a DUI after I finished student teaching due to a month-long drinking binge, and I slept with my 2 best friends’ girlfriends. As 2005 was winding down, I thought I’d just ring it in low-key at a buddy of mine’s house with a few of my high school classmates; little did I know the night would be anything but low-key.

The night started out pretty tame, as there were only about 10 of it’s at Nicks house. He bought a keg of Busch light, so we were set for the group to survive the night. We played some beer pong, some flippy-cup, fairly basic midwestern get together, but then I got a text from a co-worker of mine asking what was going on. She was only 10, and the party she was going to had fizzled out before it even began, so I invited her over, along with some of our other coworkers. Lynne was my best friend from grade schools ex-girlfriend, whom I unintentionally slept with to cause their breakup. Since we still worked together, it was hard to give the sex up.

Bi Glory Hole Virgin [M]25

Last weekend while my fiancé was out of town I got extremely horny and decided to jerk off. I found myself being drawn to glory hole videos and amateur bi mmf. Watching this videos got me so horny and I came much harder than usually thinking about how hot it would be to suck a random cock at a glory hole. I decided to have a couple beers and relax for the rest of the night.

No matter how hard I tried I couldn’t get the idea of the glory hole out of my mind. With the help of a few beers I decided that I needed to find out what it was like while my fiancé wasn’t around. I looked online and found an adult theater in a adult shop not to far from my house. I grabbed a handful of condoms, some lube and drove to the store. Once there I paid for the theater and got my tokens; the whole time being so nervous and excited about what I was doing. After going into the back I headed for the group theater which was nothing more than a bunch of old couches in a room with a projector. As my eyes adjusted I looked around and saw men sitting around in various of states of undress. Some were stroking their cocks or playing with others.

Enamored [M][F][m][f][humil][nc][reluc]

Enamored
by Carolyn Hooke
The essentials of this story are all truthful. One of my very good friends worked as an office manager for a clinical psychologist. A very conflicted young man came to her clinic one day and began a case with her group. Fortunately he had a patient and understanding counselor to work through matters with him. And, as you will see why, it became our favorite topic as it unfolded over the next few months.

Cubicle

“What are you doing for lunch?”

That was the earliest conversation I could recall having with her. She had been hired about a year after me and placed in the same business group. Initially, she’d been paired with a more senior colleague to train. I’d just turned 23 and she was one of our a recent college graduate hires.

The firm handled the registration and licensing concerns for firms operating in multiple states: compiling business documents, forms, and records and making certain that all requirements were followed. Within it, recent young college graduates were paired alongside a crowd of older workers and slowly and steadily built their professional resumes in hopes of eventually landing a better job, or, they worked there until they became a member of the seasoned crowd.