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.

Five Years of Film School Stories: Fucking the girl I was seeing while her roommate watched. [MFF]

Well, long time reader but I finally decided to share. I went to college in one of the flyover states and then moved out to LA for graduate film school, which was quite the culture shock for a guy like me. That was five years ago. I recently moved back home for a less dramatic life, but have plenty of stories from those five years to share. So, without further ado, here we go.

First, about me. I’m white, 6′ 3″, dark hair, athletic build (I’ve been told I have a “swimmer’s body”), and have an above-average cock. I’m not the most handsome guy in the universe, but people seem to find me attractive enough, so that works for me.

Anyway, this first story is about the girl I started seeing, Rachel, and her freaky roommate, Robin. Rachel was a girl defined by her smile. It was wide and sexy and she knew exactly when to flash it to make a guy feel like a million dollars. She was tall, taller than most girls I had gotten with, at 5’11”. She had these long legs that just kept going and going, a high and plump ass, and small, perky tits. She was dark skinned with big brown eyes and shoulder length hair. A directing student, we met when I pitched her an idea I had for a short film (I was a screenwriter) and we hit things off. We both adored nerdy-ass shows that got cancelled too early and drinking too much on weeknights. Sex came easy between us.

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.

[M]y first time at a stripclub

Naturally, a few months after I turned 18 I decided to check out a strip club (this was a few years ago). It was the night of New Years Day and I figured it would be a perfect night to go. I had some money, had nothing to do, and was horny. So I began to look online and found a club about a half hour away that looked like my best option.

I went and was extremely nervous as a virgin that also has anxiety. I walked up to the bouncer outside and paid 10 bucks to get in. It was a dark hallway with red lights, and my heart was racing as I went to walk up the stairs. I immediately walked over to grab a coke. Because it was a fully nude 18+ club, they didn’t serve any alcohol.

I saw a typical California looking girl up on stage. About 5’5, bleached blonde hair, slim, big fake tits, and a nice tan. I was drawn to her on a magnet, as it was the first naked woman I had seen in person. I sat down in the front row, because there were only like 4 guys in the whole club.

Shameful, Secluded Ravishment [Anal][Feminization][MM][Humliation] [xpost from a /r/dirtywritingprompts request]

I’d just turned eighteen the day before my flight crashed. Brett, the boy I crashed with, was nineteen. The flight was nearly empty and we’d been the only two in the back of the plane; it had broken free of the rest and we’d somehow glided and crashed in water. There had been a storm. It was deep wilderness. We had no idea where. We walked for seven days without finding the rest of the plane or anyone else. It seemed like we were maybe somewhere in Alaska–mountains and verdant forest stretching across what seemed like the whole world. We survived on water and very little food. On the seventh day we found the cabin. We figured it was some wealthy hunter’s cabin. The place was stocked with food, drinks, fuel, toiletries, a generator. It had pretty much everything you’d need to survive in the wilderness–except a functioning radio, any maps, or a compass. We settled into waiting it out for someone to find us in the cabin.

Shameful, Secluded Ravishment [Anal][Feminization][MM][Humliation] (from a /r/dirtywritingprompts request)

I’d just turned eighteen the day before my flight crashed. Brett, the boy I crashed with, was nineteen. The flight was nearly empty and we’d been the only two in the back of the plane; it had broken free of the rest and we’d somehow glided and crashed in water. There had been a storm. It was deep wilderness. We had no idea where. We walked for seven days without finding the rest of the plane or anyone else. It seemed like we were maybe somewhere in Alaska–mountains and verdant forest stretching across what seemed like the whole world. We survived on water and very little food. On the seventh day we found the cabin. We figured it was some wealthy hunter’s cabin. The place was stocked with food, drinks, fuel, toiletries, a generator. It had pretty much everything you’d need to survive in the wilderness–except a functioning radio, any maps, or a compass. We settled into waiting it out for someone to find us in the cabin.

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.

[MF] Seduced by bisexual roommate

I felt like I hit the roommate lottery when I met Claire. This girl was a solid 10. Full D cups, red hair, and a wonderfully toned ass. She carried herself with such confidence too. Didn’t try to flaunt it or tease me about it. It took every ounce of willpower when I met her to talk about the apartment. She later offered me the place b/c she said I didn’t try to hit on her.

Soon after moving in, I found out she had a girlfriend, taking the wind out of any hope I had of sleeping with her. It was already a faint hope anyway, since she was way out of my league. We found out that we got along pretty well and with sex off the table, I was able to treat her like any other friend, though I did occasionnaly jerk off to her.

This story is about the night I found out she was bisexual.

I was getting ready to meet a date for late night drinks. Claire came into the apartment wearing a low cut dress that showed a lot of cleavage. I had accepted sex was off the table, but I’d be lying if I said I wasn’t turned on. She noticed me.

My [F]irst Threesome

Hi guys,

Story of my first threesome – Back Story –
I, 24 Brown hair/eyes 6 2″ English Manc – Was invited to a NYE party with with a few friends. You know the types of friends that have the heavy drug parties. (some may say light – i prefer a smoke so heavy for me) – These people thrive of partying and are different people when partying. So i thought fuck it why not?

Me and a mate (kinda chubby – call him Pete) and another mate – Athletic build fairly small frame but quite muscly – call him Connor) All turn up to Connors cousins party. As the introductions go – we instantly walked in, straight to the kitchen to fix ourselves drinks and glasses etc. We give it the typical “nod” to people we knew and a well mannered “hello” to all the others. The rooms was rammed – there was people in every room. This was no ordinary house party!

The hottest sex of my [30/F] life, with my husband’s best friend [30M][MFM] [slight cuckold][detailed]

Hello all, it’s my first time sharing as I’ve never really had a sex story worth sharing until now, but here goes!

I’m Michelle, I’m 30 years old and have been married for 5 years. My husband Bryan is an an engineer for a large private military contractor so we have had to move several times over the last few years. I’ve always been kind of a hopeless romantic type. I’m an english teacher and an avid writer, though I have not been able to work during the last two years because of our moves.

Our sex life has dwindled starting from about the time we got married. We have both only had two partners in our life times. In fact, my only other partner was someone I was with twice while Bryan and I were broken up for a couple months just after college. I have a huge sexual….imagination…but have never quite explored many of the things I’d like to. I’ve always been sort of a quiet type who is just waiting for someone to bring the inner animal out of me but unfortunately my husband is similar so we’ve always been a bit timid together.