All Chapters of Tales Of A Gay Man 2: Chapter 1 - Chapter 10

50 Chapters

Freshman In His Dorm

Everybody in this story is 18+.This happened during my senior year at a pretty big college. I’d had my fun with guys over the years, and almost all had been off hook up apps. There was a few spontaneous times though, and this was one of them. I was straight, so looking for guys in public was never my thing.I was riding the bus around campus and was planning on getting off by the freshman dorms…it’s where the gym was closest to. As I stood on the bus I noticed a younger boy sitting just a few feet from me. I caught him staring out of the corner of my eye and looked at him. He, boldly, didn’t look away. Instead, he looked me up and down slowly and smiled. Maybe it was due to the fact we went to a fairly large school with a decently large gay community, but he seemed fearless in doing it. When I kept my eyes locked on him, he moved his eyes down to my pants and licked his lips subtly.He was short. Probably about 5’7”. Short brown hair and a twinkish build to him. Definitely a typical

Last Updated : 2023-08-26

Caught Him With His Pants Down

It had been a few weeks since my roommate and I had confirmed our mutual suspicions that we like the taste of a cock, on our knees, in our mouths, or bent over and ass filled.But one particular mid-week worknight I came home a little later than normal after drinks with a client. I had a healthy buzz on and on the Uber ride home realized I was going to need some sex before bed. Traded some texts with my girl but she was already in bed with an early morning and settled for the night at her place, so I headed home. It'd have to be Reddit porn and my right hand.Walked through the front door, dropped my bag, keys, thought I needed one more pour of whiskey to accompany me and my laptop to bed. In short, it was clear I was home. So, as I walked to my bedroom, I was surprised to see Brent's bedroom door wide open. Lights low, the familiar sound of porn coming from the tv and him sitting on his bed. He was also clearly recently home from work. His suit jacket was draped over his desk

Last Updated : 2023-09-03

Sleeping Slut

I have been extra horny recently, and have really been trying new kinks. One of my biggest fantasies is to be used while I am unconscious. I got an idea from watching a video and thought I would try it out but my own way. It took while to convince myself how to do it, because it was dangerous and I had to do it right. First thing I did was get a hotel room. I did not want to do it at my own home for risk of anyone stealing my things. I got a hotel room for the night and packed my bags full of all of my supplies. I got to the hotel around 6:00 p.m. to give myself time to set up before the sun went down, I laid out all of my supplies on the bed. I had rope, three dildos, a blindfold, lube, condoms, my cleaning supplies, a sex sheet, poppers, a harness, a marker, my camera, and my pills. After setting up the room for a good sex session, I cleaned myself out the best that I could. I had gone without eating for almost 34 hours to ensure that I was good. After cleaning, I lubed my hole an

Last Updated : 2023-09-05

Sleeping Slut Part 2

I laid there for only a few seconds before I realize how filthy the bed was, I quickly got up and moved to the chair. With my hole throbbing, I played the tape from the beginning. There was a good 30 minutes or so at the beginning where I just slept. Then after a while someone came in. It was a middle-aged guy who wasn't very attractive. He quickly came in and closed the door. He did a quick sweep of the room to get his bearings, and saw the camera. He asked the camera if I could blur his face out and then went over to me and stared me down. He grabbed my body and flipped me over then started massaging my ass and his dick. Then he grab some of the lube and applied to my hole. He fingered me for a bit as he let his dick get hard, then he took off his clothes and climbed on top of me. I just laid there on my stomach silently. It wasn't the best angle for the camera, all I could see was his back, and my legs sticking out. He leaned forward and I could see him starting to stick his dick

Last Updated : 2023-09-05

Sleeping Slut Part 3

The pills must have made my body fully relaxed because they kept repeating how loose my hole was, and showing how open it would stay when they swapped. By this point it was a sloppy mess. They were mounting me grabbing me by my neck with two hands and pounding until they got tired, then the next one would take over before my hole would close back up. It was such a bizarre feeling to watch a video of myself laying there unaware while this group of guys talked about me like I was an object and passed me around like a bong they were sharing. They were being so aggressive, encouraging each other to fuck harder and deeper, to make sure I felt it the next day. It worked, I definitely felt it right now.They kept shoving their hands down my throat, amazed how they can invade my body without me knowing. One guy said I was too loose and grabbed the largest dildo. He lubed it and stuck it in with his dick. They all seemed surprised at how wide my hole was stretching, making me think even more t

Last Updated : 2023-09-05

Help My Straight Friend Out

So we have been friends a really long time and he of course knows I’m gay. We are really close, so it wasn’t hard to establish this arrangement. He pretty much just asked me one day if I’d do it and not tell anyone, I agreed, and I do it for him once a week or so. It’s hot, he always holds my head and makes me blow him really really fast so he cums quick. He says my blowjobs are the best he’s ever had.Will he ever return the favour or could it turn into something more?

Last Updated : 2023-09-12

Roommate DL Top

This morning, I moved into my place for the new semester. It’s not a dorm room, thank god, but it is a big apartment building that is mainly students. Regular people can live there too tho! I was the first one there, bright & early, and I got my stuff arranged and when I was setting up in the kitchen (I’m a part-time chef, so I have a good amount of equipment), my new roommate walked in. He’s an attractive guy, 22, dark haired, clean shaven, maybe 6’0” and pretty average build - he clearly worked out and took care of himself, but not a bodybuilder. Anyways, we exchange formalities, say our hellos and both get on with moving in for ourselves. Later, we had a drink together and talked, he’s a student as well but took gap years to work in a factory and save money, he’s from cali, he was a wrestler in high school. It was cool. We have another roommate, but he’s not gonna be here for a couple more days. Later, back in my own room, I start to get horny. My favourite thing about living aw

Last Updated : 2023-09-12

Me & The Foreman

Years ago I used to work construction. I had only worked there for about a month but my foreman and I became pretty good friends. He was a 45 year old man and I was only 22. Every once in a while we would go and have a beer or two after work. He would always be talking about the problems he was having with his wife. I’d try to help with advice but I don’t think I was any good at it. One night he was giving me a ride home and he mentioned something about how if she just gave him head once in a while it would relieve a lot of stress. I jokingly said “I’ll relieve it for you”. He kind of took a double take at me and we both laughed. After about 5 more minutes of driving he randomly pulled into a Walmart parking lot. I thought he might have to stop and pick something up but I found it weird that he parked in the back of the lot. He put the car in park and turned to me and asked if I was serious about what I said. I nervously chuckled. “Ya. I mean, sure” is what came out. He didn’t hesitat

Last Updated : 2023-09-23

Brothers “Straight” Best Friend

I let my little brother’s friend Elijah move in with me. Dude was desperate to find a place on short notice, he broke up with his girlfriend of 4 years and she was kicking his ass out. He couldn’t afford his own place, so I rented him a room in my basement on a 1 year lease. We are both students, him being 24 and in college, I’m 32 and pursuing my masters. I’m 6’5, brown hair and eyes, muscular, and hung. Elijah is 5’11, blonde hair, freckled white skin and also muscular. We rarely hit the gym together, I tend to hang out with people my age. I’m also bisexual but never told a soul. While I was out of town, I let Elijah borrow my MacBook MagSafe charger. I was taking a semester off and rarely used it. A month later it was time to register for classes and my laptop was dead. Elijah was at work so I went into his room looking for the charger. I careful searched as to not make it look like the FBI was looking for the Watergate tapes in there. In his desk I came across what appeared to b

Last Updated : 2023-09-23

Friend Tries My Ass (Part 1)

For a little over two years now I’ve been having regular fun with my “straight” friend. We usually hang out every couple weeks and about 75% of the time I end up blowing him. It’s a pretty good deal for both of us. I satisfy my craving for dick and he gets to a blow a load in someone's mouth. Sometimes we jerk each other off and on a few occasions he’s actually given me head. Despite all of this he maintains that he is straight and that we’re just comfortable with each other. I bring this up because it is likely the reason I have never offered him my ass. For whatever reason I never thought about it, never considered he’d be interested. After some thought though I decided it was time to change that. I discussed my desires with my wife, who gave me the ok, saying it fell well within our normal fun. Desires approved I made a plan. During the football season my friend and I get together every time our team is playing, so I didn't have to wait long. As usual we started playing with each o

Last Updated : 2023-09-23

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