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Help My Straight Friend Out
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2024-10-29 19:42:56Related chapters
Tales of a gay man 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
Tales of a gay man 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
Tales of a gay man 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
Tales of a gay man 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
Tales of a gay man Friend Tries My Ass (Part 2)
The slow thrusting began to quicken and he gripped my hair, pressing my head into the wall as he began to drive hard into my tight hole. The room filled with the sounds of his hips slapping against my ass. The pleasure filled me, the thick head pulling deep inside me. I let out a loud moan as he pulled all the way out to the tip then sunk all the way back in. I was not new to anal but god his cock felt so much better than the others. The roughness with which he pounded me, pinned me to the wall, it was perfect and I felt as if I might cum right then and there. Eventually the thrusting stopped and he grabbed my hips pulling my ass back and pushing himself in. Balls deep inside of me he lead me backwards and we stepped together back to the couch. He sat down and I came down with him sliding down even deeper onto his cock “Fuck!” I cried with the sudden sting. “Ride my cock” he said. I adjusted myself, putting my legs in between his knowing it would make my ass look that much better and
Tales of a gay man Customer Service(D)
I was traveling through California’s Valley. I stopped at a city that has a porn theater and video booths. I paid to go into the theater from a tall, in his 20s bearded guy, stayed for a about 15 minutes, there was a bunch of old fat guys in the back row and I just couldn’t get into it. I exited the door and the five rows of booths (two per row) were right there. I went down into the third row first booth. The booths have a cushioned bench with a big screen but no doors. A few guys passed by to check if I was jacking off, but I wasn’t. I think the booth area was finally empty (I didn’t hear anyone walking on the squeaky wooden floors). I undid my baggy jeans and pulled my cock through the fly of my plaid boxers. I heard the door to the enclosed employee booth/register. I could hear the sound of a sloshy mop. He finally came to my row and started mopping towards the back of the second booth. I had a choice to make. Hide my dick in case he kicks me out or just take a chance. I decided
Tales of a gay man Summer Camp BJ
I was 23 and Toby was 24 in this story.I’d arrived at the summer camp in Canada with excitement in my veins. Ditching my shit job for a summer of fun is just what I needed. I was going to be a camp counsellor along with a load of other young people. One guy, Toby, kinda stood out, he was from Michigan, and he’d played lacrosse in high school. He was handsome in a slightly goofy way. He has bushy brown hair and he was tall, athletic. In the few weeks before the campers arrived, we got to know each other. I really liked him, we made each other laugh and just his presence nearby got me hot and heavy, with at least a semi. I found him irresistibly hot. The sight of his clear bulge in his shorts was too much to bear. His cock outline looked pretty big. Sometimes he’d have a line of sweat on his shorts which made me rock hard. I jerked off like crazy thinking about him. Each morning the guys would shower first and then the girls would shower after every guy was done. The next week it s
Tales of a gay man At The Airport
During one of my recent trips, I visited one of the airport lounges. As I walked in, I saw this guy staring at me. He was good looking and looked lean from what I could tell through his clothes (he was wearing a slim fit t-shirt).I found a seat just across from him, got settled down, and went to get something to eat. I looked up occasionally and would see him just staring. Normally, it would have felt creepy, but I was actually quite excited that he was checking me out. Note: I am bi and, for whatever reason, seem to attract men more than women.Anyway, I decided to say hi and he said hi back. We ended up having a good conversation around our workout routines and I told him that he looked good. He thanked me and said, “I bet you look great too, although I can’t really tell since you are wearing a hoodie. Can you take it off?”I told him I wasn’t wearing anything underneath (yes, I know people have opinions about that, but I do wear my hoodies with nothing under). He’s like, “well, we
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Tales of a gay man Soccer Player Slut
During my sophomore year hoe phase, a lot of crazy times happened. This one was probably one of my top 3 faves tho.I met Evan in psych that year. We were paired together for a group project early on and he and I would meet regularly to work on it. Once the end of the semester came, we finished the project, and also became decent friends. Evan (19) was my year and played soccer for our school. He was pretty lean and toned with blonde hair and blue eyes, just taller than me. While we were working on the project together that first semester, I’d see him working out in the gym a few times. We’d say hi and do our own thing. Towards the end of October, we started talking a bit more and complaining about classes or whatever. As we were finishing our project, we started meeting twice a week to get it done. One night we just stayed up till 3 am watching YouTube videos, the Try Guys I think lol. We started seeing we had similar interests and would grab lunch after psych together. The more
Tales of a gay man Blown By Straight Classmate
I sat next to Charlie every physics lesson, we'd never interact outside of these lessons but when we had them we'd get along swimmingly. Our sixth form was part of our high school, and I'd been out since year 7, so everyone knew I was gay and no one really had a problem with it. And by the time we'd gotten to sixth form as much as we were all horny teenage boys everyone was a lot more mature and accepting, including Charlie. In fact, Charlie loved asking me about the ins and outs of gay sex, everyone in my school did so I never really questioned it - that was until the day things escalated a bit further than normal.Charlie was about 6 foot tall, broad but slim with an olive complexion and dark, straight hair. He was a very stereotypically attractive lad, but I'd never thought about him that way. I was skinny with fair skin and dark hair, nothing particularly amazing but I've been told I have a handsome face and a girthy dick, but we'll get to that later. One thing that made everyone
Tales of a gay man Best Friends Slut
It was last December, when I once again downloaded Grindr to search for a guy to have my first time with. To see, if I really like what these urges I had for 3 years planted into my head. I took pictures from my always shaved ass in the bathroom to show these Tops on Grindr what I had to offer. On the next day, I met with my best friend to watch some football at his home. I have to tell that I was super excited about that, of course I knew nothing would happen, but since I'm 15, since these thoughts started, I wanted to have sex with him. I like the imagination of him and his big dick pounding me. So we took some snacks and watched the Bundesliga games. It was a fun time until that one mistake, I showed him a picture of my cat sleeping in a funny position. He wanted to phone to zoom in, so I handed it to him. He zoomed and afterwards scrolled to the right, where his eyes saw my naked body, posing to get the attention to my ass. I saw it and immediately began to take my phone back and
Tales of a gay man Fucked The Cum Out Of Me
My husband/Alpha and I love to have kinky fun in the bedroom, which usually means that he teases and edges me, plays with my nipples, pushes my head down onto his cock so that it goes all the way back into my throat, then bends me over and fucks me until he cums. The catch is that I’m never allowed to cum, no matter what. He likes that I get sluttier and more desperate for cock as I get hornier. About a year or two ago, we decided that it would be fun to add other guys to our sexual play, which usually results in me sucking everyone’s cocks until everyone blows their loads in my face. With one friend in particular, it was a little different though. We had hung out with this friend a few times, so we knew him somewhat well. When he came over, my husband set the scene and let him know that I was going to be their sex toy for the night. We started with them laying on their backs and me sucking their cocks while I straddled them, but after about 20 minutes of that, they got bored. My hus
Tales of a gay man New Year Orgy
I'm not a noob. I'm versatile, insatiable, but shy...ish. My best friend is a great big ho! He finally convinced me to come with him to a New Year's Eve party - a nude one. We've been hanging out at the nude beach forever, so getting nekked with guys is nothing.Getting an erection? Yeah, not used to that. There must have been forty or fifty guys - and every single one of them was a gym rat, which I am definitely not. Seeing those guys, I told my friend I was out of there. It was so intimidating! He didn't want me to go and started enlisting help. Oh my gosh! I was mortified - and then guys began touching me, kissing me, and slathering ....things on me.I was about to scream and run when my friend grabbed my face and began kissing me. He also whispered calming statements. A mouth engulfed my ...self and it didn't take long before I was harder than a diamond. My friend and I have been besties for over fifteen years but we never did much together sexually. I'd secretly wanted to for yea
Tales of a gay man Dicked By Straight Roommate
Junior year of college I was roommates with this guy named Andy. He was a really nice guy, and quickly became one of my best friends. He knew I was bi and it didn’t seem to phase him at all. We had always maintained a fairly platonic relationship. He was a bigger guy, 6’2 with an athletic build, probably 200lb. Dark curly hair and piercing green eyes. He had recently broken up with his long time girlfriend, and we had been going out together drinking often. He would usually try, unsuccessfully, to pick up chicks. One night we were at a bar just off campus and he had had several drinks. It was getting a little late, but it was down pouring outside so we had been trying to wait it out. Unfortunately, the rain wasn’t letting up and the bar was closing down, so we began the 10 minute walk back to our dormitory. Luckily it was really warm that night. He was pretty drunk, and stumped through the rain, jumping in puddles laughing it up. By the time we got back to our room, we were both abso
Tales of a gay man Cousin & Me
I was in my juñior year of highschool and had a gf, when I experienced my first dick of my life. Me and my cousin were hanging out at a parks bench, on an evening summer day, when all of the sudden he started asking me questions about fuckin girls. I told him my experiences with girls. He than suddenly asked me a random question "what would you do if a guy tells me he wants to suck my dick?". Being a young horny guy , I answered him that I would probably let him suck me up. He fallow up with another question " what if he wants you to fuck him?" . I told him that i would also fuck him, a hole is a hole.. He smiled and saids that's cool. I asked him "how about you?". He said "I would too". All of the sudden he reached for my dick and starting rubbing it. I instantly got rock hard and didn't stop him. I also reached out and started stroking him. We continue jerking each other's cock , as he got harder and harder I realized he had a bigger, thicker cock than me and curved. It felt so good
Tales of a gay man PA (part 2)
A week had passed since I had been ruined by Mr Duncan's cock. My hole still throbbed whenever I thought about it. When I think about how I fished his used condom out of me or how I think about how his cum leaked out of me for the next 2 days - reminding me of what I had allowed him to do to me. It was like the thought of it was haunting me, whenever I closed my eyes to sleep I could hear the sound of him slamming himself into me and I cried. How pathetic I'd become.True enough to his word, after I sent him all the documents he asked for, I heard a loud knock at my door."*UPS!*." Came the voice.Stepping over the pile of past-due and threatening letters from the landlord, I opened the door. The man behind the door was holding a massive box which obscured him behind it."Isaac Walker?" The man asked from the behind the box, the strain in his voice clear."That's me.""Oh great mate, you have no idea how heavy this thing it." He put the box on the floor, it impacted with a slam. "Oh s
Tales of a gay man PA (Part 1)
I would tell you my name, but it doesn't matter. The fact is I was 19, broke, and desperate. I lost my job at a tech start-up a few months ago and after the pandemic I couldn't find another to save myself, I was ready to do just about anything. I applied to everything I could, it was on one of my 2am manic job hunts that I saw this advert:"Wanted: Personal Assistant (full time) - Cambro, Harper and AssociatesApplicant must be between the ages of 18-24. Ideal candidate will have a level of physical fitness as job role may require moving and handling. No experience required, training will be provided.Pay negotiable."I had no better options, so when I got invited to interview I leaped at the chance. I showed up to a tall glass tower building in the city. *Do I really want to be a cog in a corporate machine?,* I thought. Walking into the sleek lobby, I was ushered up to the top floor of the impressive building. The elevator doors open to reveal another reception desk. I walked up
