Tag: Gay

Taking /u/highavailability’s anal virginity. Lots of pictures. [f/m] xposted from /r/hastories

It’s no secret that I’m kindof obsessed with HA’s ass. It truly is a thing of beauty. I’ve never been particularly interested in exploring the male-gspot with anybody else, but HA’s ass is just begging to be played with. I initially approached that line awhile back when we were both pretty heavily under the influence. There was only light external massage on that occasion (mostly bc I have long fingernails), but I couldn’t stop thinking about it thereafter. HA was, understandably, apprehensive about the possibility, but somewhere along the way his curiosity got the best of him and he gave me carte blanche to do whatever I wanted…with the stipulation that anything I did to him, he could also do to me. Well, seeing as how he has fucked me in the ass on multiple occasions, this fine print didn’t dissuade me in the least.

At the time, I didn’t think I’d be seeing HA until mid-January, so I leisurely started reading up on prostate massage, watching tutorial videos, and consulting with my gay bestie. I ordered some things online and continued with my “education” because I approach sex like I do everything else….all or nothing, and if I’m going to do it, I’m going to do it right. Read more »

(M)y first time with a (T)rans girl

(This is a true story and also my first attempt at writing. Hope you enjoy)

This happened back in college at the 21st birthday of an acquaintance of mine. My friend Josh was a pretty cool guy, lived in a decent sized house off campus, and loved to throw parties. Josh also happened to be gay as were most of the attendees at the party. I had hung out with him before and knew what his party scene was like. Although I was straight none of his antics never bothered me or made me feel uncomfortable. The same cannot be said about his roommate.

The party got started about 9 o'clock and there were probably 30 to 40 people in the house. Josh's roommate was there and was already drunk by the time I got there. His normal aggressive manners were on full force thanks to the alcohol. I had come in from the patio to get another drink and the roommate corners me by the drink table. He basically pushes me into the table, grabbing at my crotch, and tries to kiss me. Now, I'm not homophobic in any way, but I can't stand this type of aggressive behavior from people. Read more »

[M] My night doing [M] what a redditor told me

M/M story here. Long post. Skip to "THE GOOD STUFF" if setup isn't your thing.

A few weeks back, I got home from work after a long week, and started chatting with a Reddit buddy of mine. After some normal back and forth, I mentioned how horny I had been all week. He ended up edging me on even more, and getting me feeling particularly horny, and a bit aggressive. It was a Friday night, and I had a few friends I was planning on going out with. My Reddit buddy told me I should take someone home, then send him some pics of us together. It was something I had never done before, and the thought felt a bit exhibitionist, and pretty hot. So, I made this my mission for the night, and headed out with my new goal. Read more »

(m/m) He gave me (straight) my first, and most intense orgasm with a man.

Let's start with a description of myself and Joey first. Joey is six feet tall, muscular, brown hair, blue eyes, chiseled jaw and a great smile. A very handsome guy.

I'm a little bigger, topping out at 6'5", 200lbs. I have short thick brown hair, dark blue eyes, a swimmers build and very thin body hair. I have a bit of a baby face and could be defined as a twink.

I had been single for a couple years when I started getting bored with jerking off. I had sex occasionally but I was having trouble finding a steady partner. I ended up trying new things, I started with fingering my ass lightly with a finger while I jerked off. This got more and more intense as I bought lube and started pushing more fingers inside of myself. For those who do this they know it's not a comfortable position, I wanted something bigger and easier filling me up. Read more »

Strapped to a St. Andrew’s cross [group][m/m/m/m/m/m/m/m]

This is a true story from the Bournemouth gay sauna-bar at its old location, when it had a dedicated playroom. Locals will know what I mean.

The sauna-bar was huge. Half of it consisted of showers, saunas, hot-tubs and the like. Separated by a bar in the middle, the other half was a dark labyrinth of rooms. Some were private, some had mirrored windows and some contained toys. At the very back of this maze through a barred door was a bondage playroom replete with a lovely assortment of equipment. I’ve had many adventures in that place, but this was my favorite.

In a dark corner of the playroom lived a sturdy wooden X-shaped St. Andrew’s cross. It was heavy and intimidating, with a complex array of straps and buckles dangling from its matte black bulk. Visible to the whole room, it set the tone for the entire area. Amazingly, it was never occupied. One day, I decided to change that.

Before my next visit to the sauna-bar, I bought a blindfold and a piece of underwear made from leather straps that came with an accompanying metal cock ring. I nervously made my way there early in order to arrive before it got busy; so early that I was the first customer of the evening. Read more »

My flat mate and his gf suck my cock (MMF)

I live in East London, UK and this is the true story about what happened when me and my ex-flat mate played around with his gf.

Me and my flat mate had watched porn and wanked together before. We both got off on watching the movies together and describing how we'd share the same girl in a threesome. We are both bicurious and talked about how we could try and sneak a few grabs of each other's dicks while fucking his gf without her knowing.

So one Saturday morning I got a text message from him saying how he'd been chatting to his gf about me watching them fuck. She wanted to watch me wank myself off while they were fucking. I couldn't join in but could watch. This was on for that night!

Me and him exchanged a few text messages and things escalated a bit where she wanted to watch us wank each other. My cock was getting harder with each text message.

So later that night they came back to the flat and we arranged to go to the local pub for the evening to get a bit drunk before coming back home. Read more »

Poker with my wife, her bf and my fwb

For those who haven't read my previous stories I'm Kai (36) my wife is Haley (34) the bf Ian is (29 I think now) and my fwb Laura is about 31.

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If you don't understand Texas Hold em you may need to look up some bits.

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"Two pair on Queens" smiled Ian as the sandy haired and broad shouldered guy placed his cards down on the table. Haley and I had folded when Laura and Ian started bidding stupidly out of nowhere. The hands can't have been that good as they were looking apprehensive right up to the river then went crazy. Presumably both had a Queen in hand. Laura my raven haired, amber skinned and large chested fwb purred "Don't beat my witches honey" as she dropped her pair of Queens onto the table with a smirk.

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"Well shit." Cursed Ian with a smirk "I thought I had you."

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[GAY] Halloween 3sum MMM

I was invited to Halloween party downtown this year. When I showed up to the address, it was in a nasty part of town. Literally crack whores and homeless dudes everywhere. Despite the scene, I said fuck it and went to enjoy my night.

The guy hosting was from my college math class. I thought he was super cute, but I didn't think he knew I was gay. I came to the party to score some ass. I didn't care if was hairy or they just took a messy shit. I wanted to stick my flesh pole in some ass.

The beers started flowing and the host was too busy to chat with me. I ended up talking to his neighbors who lived across the hall. Let's call one, /u/ChokinMrElmo and the other /u/Hulkx.

After a few more drinks, /u/ChokinMrElmo invited me back to their apartment. He whispered in my ear that he was a power bottom and craved dick. He wanted me in him now.

We said our goodbyes, and the host raised an eyebrow when I told him that I was going across the hall. Read more »

That time I watched hi[m] [f]uck my dream girl and I learned size matters

This is a long, completely true, vaguely cuckold-y story from my college days at a large American university. It’s about how a small group of girls who I hung out with a lot proved to me that size matters. I’ve changed the names for obvious reasons, but every detail is as accurate as possible. I made up things like measurements, because obviously there wasn’t a fucking ruler lying around every second, but I consider myself a pretty decent judge of breast and penis size just from having a ton of experience with both. (I’ve been with dozens of women, and I’m one of those over-the-top critique-ers of dick pics on the internet who knows Mandingo is really only like 9.5” long at best.) So there you go, read on if you want to know my story.

 

 

Back when I was in college, I had a close girl friend named Nicole. To be honest, I was friend zoned by her. She had an interest in me, briefly, but I pursued it too hard – which is very unlike me – and I pretty much lost my chance. I lost it completely when she became enamored with the male subject of this story. Read more »

I Cheated on my Boyfriend at Work. [F/F]

I’ve changed some details about this because I could get in a lot of trouble if it came out. For that reason I might not answer too many questions. Well I won’t be too specific with my answers at least.

My name's Helen I’m a very normal person really. I’m outgoing and like normal stuff, and I have an outgoing boyfriend who likes normal stuff too. We both exercise a lot together and we’re both in good shape which is something important to both of us. But other than that we’re like any couple. Our sex life is fine too, and the only complaint I have is that he doesn’t go down on me nearly as much as I would like. But it’s not a big problem really. All in all we’re very happy, we live together, and are planning a future. So I never thought of myself as a cheater, which is why it’s so weird to me that I’m writing this. Part of me writing this is because I want to share something with a subreddit that I have enjoyed for a few months now (made an account for this!), and part of it is to get it all off my chest because it's been a weird few weeks. Read more »