Author: Sex-DungeonMaster

[MF] Domination & rough sex with a stuck-up hipster barista

Aria and I met at the exact right time in both of our lives. We had both just gotten out of serious, long-term relationships. Our break-ups were messy ends to toxic relationships that had been on life support until we pulled the plug. I dropped in to the coffee shop she worked at from time to time, although we knew each other through friends-of-friends outside of her work. One day while we were making small talk she gave me her number and we got to texting all night.

We vented about our exes and talked about the relief and the numbness we were both feeling. Part of it just didn’t feel real. Like clockwork though the conversation shifted to how we could make ourselves feel something. You may know where this is headed. Our first ‘date’, if you want to call it that, ended with some of the rawest, roughest sex I’ve had to this day. This woman bruised me and drug her nails through my back, drawing blood on occasion. I’d respond by picking her up and fucking her against the wall till she couldn’t see straight. Read more »

[MFF] Adventures in swinging: First threesome with my gf & a married woman

So far I’ve only really talked about encounters with individual women, but I went through a phase with one of my exes, Beth, where we would fuck other people together. And sometimes not together. This particular instance was early in our experimentation, our very first threesome. Our “date” was a girl named Kara, who was actually part of a thrupple (she had a husband & live-in boyfriend). We all met for our first date and had a couple subsequent dates at their house, just hanging out, sometimes getting a little naked, sometimes kissing.

We were basically just a group of friends that knew at some point they were going to have sex. It was kinda cool. Kara was a very cute, nerdy, weeb; she loved anime slice-of-life shit. I really wanted to suck her titties so I pretended to like anime slice-of-life shit. But seriously, I liked her. I also liked her… dudes. They were both good guys who were easy to talk to. If we never had sex I probably wouldn’t even be upset. It just felt good hanging out with them. One night Kara came by herself over to my house to hang out with me and Beth. This was unusual but not so much so that I thought anything of it. Read more »

[MF] Reverse ‘bored and ignored’ blowjob from my degradation-seeking gf

I’ve always been a pretty avid gamer, but when certain games come out I sometimes can’t help but become entranced. Blame it on my ADD. The summer of 2012 was no different. Mass Effect 3 had just come out and although I’d completed the campaign I found myself addicted to playing the multiplayer online. I had a very powerful Vanguard that I’d zip around levels with, absolutely decimating everything. When I got bored of easily beating gold and platinum I’d switch over to my sniper Adept and just play around with some good old fashioned space magic, trapping enemies in midair before riddling them with holes. Say what you will about the Mass Effect franchise but I was having the time of my life. Around that time I was also dating a gorgeous black nerd named Kay. Read more »

[MF][MF] Fingering my lesbian friend in the club & fucking her cousin back home

For a couple years in my 20s I was part of a friend group that loved to go clubbing. I liked getting drunk and sleeping with randoms I’d meet at the club, so I went along. Several of the girls in the group were gay including Lilith, who came out with me that night. I had always liked Lilith, she was just this beautiful, curvy ball of sunshine. She had just gotten out of a pretty toxic relationship with her ex-girlfriend and I think she just wanted to have some fun. Despite my horndog nature, my first priority is generally making sure my friends are having a good time while also making sure they’re not falling on their asses drunk.

So I spent the first half of the night buying fireball shots for Lilith and myself (her favorite, not mine) and trying my best to get the perfect level of drunk for the dance floor. Over the course of my life some very generous people have told me that I’m a good dancer, I’m not really sold. But I will say that I’m what you might call ‘pretty fly for a white guy’. I look like fucking Shaggy from Scooby Doo, so people are always shocked to see I have decent rhythm and smooth footwork. The problem is that if I don’t get drunk enough I will never have the guts to get on the floor, so when I go clubbing I have to front-load my drinking. I started with 2 shots and a ‘strong island iced tea’, by the time I finished the cocktail I was convinced I had Liberace’s drip. Perfect. Read more »

[MF] Possibly knocked up a single mother of two

Another story from my extremely unwise twenties. At this particular time I was kind of an obnoxious shitposter. I posted memes all day on facebook and was quite unfortunately “horny on main” as the kids say. Apparently I garnered the attention of another shitposter named Gemma. She was an incredibly funny lady and we had a very casual online friendship that consisted of us sharing jokes and liking statuses. Simple, meaningless shit.

One day she liked one of my overtly horny memes about not pulling out and immediately sent me a message. It seemed like harmless flirty humor but I ended up making a joke along the lines of “You’ve already got 2 kids, are you trying for lucky number 3?” This went back and forth, I teased her and she leaned fully into it.

“I’m a sperm bank, okay?” She joked, “So are you gonna make a deposit or what?” I got a kick out of that one. But I definitely got the vibe that she was only joking if my answer was no. I didn’t know much about her personal life but she seemed like a person with a lot going on. Always trying to catch up, never quite making it. She had two kids with (I believe) two different dads, she had pink short hair and she apparently could not use a condom to save her life. Read more »

[MF] Knocked up my [18f] co-worker in a parking lot

When I was a younger man, I worked at a terrible convenience store on the graveyard shift. My job consisted mostly of serving and cleaning up after drunk people and various non-drunk regulars. When this happened I would have been either 22 or 23. Most nights were uneventful but about once a week, something mind boggling would happen like someone would pee on the floor or fall asleep in the utility closet. It was a very memorable job. Being the only semi-attractive guy on night shift, all the older drunk ladies would come in and hit on me. One of them tried to drag me into the bathroom one time.

Around this time I was still pretty deep in my awkwardly shy phase, so I was flattered but always responded with a polite “no thank you.” My coworkers thought I was a boy scout, but really I just had only ever been in long term relationships at that time. I wasn’t even sure how to parse having casual sex and for some reason I was very worried about losing my shitty job. So I kind of kept everybody at work at arm’s length. One of the evening crew, a young girl named Autumn, would come in sometimes at night for a drink or a snack and just make conversation with me. Read more »

[MF] Big titty goth gf accidentally slips it in while grinding

Since my first few stories were less than chipper, this is a story from when I was in a long-term stable relationship (every now and then I shake things up and try to be happy). I had been seeing this beautiful girl for a few months and we were in that phase of the relationship where you just want to fuck every which way all day long. Drea was very cool and aloof but simultaneously deeply anxious. As a fellow anxious dude that pretends to be chill, we hit it off pretty quick. This was before I knew such a thing as a “big titty goth gf” existed, but that was Drea’s overall vibe. Always in black, always with the big titties.

One snag in our desire to have infinite sex was that Drea had a looming fear of getting pregnant. She was extremely adamant about condom use, which was probably wise considering she wasn’t on birth control. We had talked a couple times about her getting on the pill but she hadn’t gotten around to it. At this point in her life, Drea had never, ever had unprotected sex. I had been having unprotected sex since I was a teenager because I’m an irresponsible hedonist. Read more »

[MF] Friendly wager with a sweet & slutty gamer girl

As a nice change of pace, I want to tell the story of a first date where we just had good, clean fun. Well maybe not that clean. But it was a brief period of no drama, no strife. Just pure exploration. It began with a match on Bumble. Bumble back then seemed to yield one of two types of women: a woman who was tired of the hookup culture of Tinder, or a woman who was using both Tinder AND Bumble to double up on her potential to get laid. Ellie was the latter. On her profile I believe she made reference to her love of tequila which I also have a deep affection for. We hit it off fairly quickly and it immediately became flirtatious.

In her pictures I could see that Ellie was cartoonishly bottom-heavy. On top she was almost flat chested but her hips were just unreal. Very wide-set with a nice thigh gap despite her thighs also being thick. She had what we in the biz call child-bearing hips. Her face was deceptively cute. A dusting of freckles adorned her chubby cheeks. She had hazel eyes that looked like little sunflowers, and her short, strawberry blonde bob really accentuated her slender neck. If Ellie had just been beautiful and adorable that would have been plenty. She also happened to be absolutely filthy AND interested in gaming, essentially a perfect human being. Read more »

[MF] Losing control with a one night stand

This is another story from the before times. From the age of having risky sex with strangers without much thought. Normally the women I met for casual sex would end up hanging around for a while until one of us lost interest. This was the first time I ever had a one night stand, and in a city I was only visiting no less. I got to work immediately, looking for tinder matches in the local area and after 2-3 dead ends I had a bite.

Jen was a very cute, kinda chubby girl of southeast asian descent (I want to say Vietnamese but I didn’t really ask). She had that sort of lighter caramel skin tone, black semi-wavy hair and well-shaped lips. We talked over the course of the week, ironing out the details at first. According to her, she was in a long distance open relationship and she had one rule with her boyfriend that she absolutely would not break: always use condoms with outside people. I was totally fine with this, it would be dumb (even by my standards) to go bareback in this situation. Read more »

[MF] Watching porn with a friend gets messy (part 2: I did mention it got messy)

Just as an aside I’ve been writing for about 3 days straight. I have serious problems with focusing and memory so when inspiration struck I just kind of dropped everything. I had a really good time recalling some cherished memories from my spank bank and I have many more but I will probably be taking a break after this one. It’s pretty damn long so I’ve sectioned it off a bit, hopefully it’s easier to digest that way. Some of you have expressed interest in how things turned out with Casey so this is that. I hope you enjoy reading and I hope to bring you guys more stories in the future, preferably some more lighthearted ones.

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In the months following [my experience with Casey](https://www.reddit.com/r/gonewildstories/comments/is90qk/mf_watching_porn_with_a_friend_gets_messy/) it became apparent that I had deep feelings for her and I think she knew that. Every intimate moment we had shared before now suddenly seemed much more meaningful to me. Those late nights at the bar when she’d leaned over and laid her head on my shoulder. The secrets she had shared with me. So much seemed new and different; my mind raced to follow it to its logical conclusion.

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