All Chapters of Tales Of A Gay Man 2: Chapter 31 - Chapter 40

50 Chapters

Rugby Players First Ass

My boyfriend has been away for a few days, and I’ve been taking advantage. Last night I invited over this 19yo curious college guy I’ve sucked off before. He’s a rugby player, beefy, blonde, fat 7” cock. I was just expecting to suck off another big load.About 10 minutes into the blowjob, he starts spreading his legs wider and leaning back so I can see more of his hairy hole. I’d never eaten his ass before, but decided to give it a shot. Slid my tongue down his dick, down his balls, down into his hole. His moans told me right away he was into it, so I dove in.He was so into it, I finally decided to go for it and slide in a finger. He tensed up for a second but then relaxed and told me to keep going. Fingered and sucked him for 10-15 minutes before he asked me to fuck him.Took him back to our bedroom. Positioned him face down in my boyfriend’s pillow with his thick ass up. I ate him out some more before I mounted him. Fucked him in that position and 3 more for an hour before I shot m

Last Updated : 2023-10-19

Sus Straight Friend

Hey, I’m your typical sad closeted high school senior. I live in North Carolina, but since I’m from a city it is a bit more progressive than the rest of the state. Sometimes I wish that it wasn’t though.There are a few businesses downtown that have pride flags in their windows and quite a few people at my school claim to be allies. But that doesn’t make it any easier to come out. I’ve thought about it for the past few years. In fact, I almost told one of my friends that I was into guys when we were freshman but chickened out.As the lies about liking girls started to pile up, it just became easier to stay in the closet. At least that’s what I’ve been telling myself. In all honesty, the reason I’m still in the closet is because I have no idea how any of my friends or family will react.I suspect that my mom might be okay with it. And by okay, I mean she won’t freak out and disown me. She won’t be flying a pride flag or anything though. My dad and step-mom are a different story altoget

Last Updated : 2023-10-20

Sus Straight Friend Isn’t Straight

So after Kevin sent me the sus snaps, everything seemed to go back to normal. We acted the same way that we always did towards one another in school. He didn’t mention anything and I sure as hell didn’t bring it up. A few times at school I caught him glancing at me. It was probably nothing, but I couldn’t help but wonder if he was checking me out. My mind kept going back to the snaps that he sent me. He had practically shown me his dick. Well, I guess technically he had shown it to me, just not the tip. I couldn’t stop wondering if he was ever going to do something like that again. Maybe I could casually mention something about it tonight? How the hell does someone casually bring up showing them your dick? “Hey Kevin, mind showing me that monster in your pants again?” Yeah, real suave. After school I was a nervous wreck. I could hardly concentrate enough to do my homework. Once I finished I sat on my bed glancing at my phone every few seconds. I kept trying to start a message to Ke

Last Updated : 2023-10-22

Friends Dad Part 1

My best friend's mom passed away when we were kids. His dad never remarried or even dated anyone for about ten years. I spent a lot of time at their house and it took a while for his dad to come out of his room to sit with my best friend and I. As time went by he started to socialize with us more and more. We had sleep overs at his house, and occaisionally at mine. Eventually we graduated highschool and my friend joined the military. His dad told me not to be a stranger and to visit him once in a while. And I did. We had some good talks and joked around. I also helped him do projects around the house. One evening after helping him, we sat and talked. He told me how lonely he was and he missed his wife. We talked for a while longer before he mentioned he missed having sexual contact. At this point I had already done a lot sexually (with guys) and was willing to help him out. I asked him if he had anybody in mind and he said, "no" he just needs to do something other than jacking off.

Last Updated : 2023-10-23

Friends Dad Part 2

So after blowing my friend's dad a few times I asked him what he thought about doing more with me. He said he did and that I have a nice ass. He asked if I had ever been butt fucked, I told him I have, then we talked about with how many guys (3) at the time and all three were seperate, 1 was just once, the other two were repeated times and I knew all 3 very well. Most of the time protected. And I am clean. He invited me to spend a night with him on the upcoming weekend and I gladly accepted. When that night came I went to his house "prepared". I showed up at around 10pm. Wearing sweat pants and t shirt no undies. He was wearing just his bathrobe. We made small talk for a few minutes, he looked nervous and to be honest I was a little nervous myself. He was anxious to get started. We still havent kissed at this point. We stripped down and laid on his bed. I knelt next to him and rubbed his chest and his little beer belly, then I stroked his cock a little before sucking it. Once h

Last Updated : 2023-10-25

Forced In The Bathroom

This story takes place when I was 19. At this point in my life I had slept with 2 men but wasn’t overly adventurous with my sex life. This Event was traumatic for me but also was kind of a sexual awakening. I hope you enjoy.One night at the beginning of summer I was driving home from college to my hometown. At this point I had been driving for over 6 hours and it was around 2am. I had desperately needed to pee for the last 20 minutes so when I saw the sign for a rest stop I turned off immediately. I found a placed to park and quickly looked around the area. Mine was one of two cars in the parking lot. The other car was on and I could see the faint silhouette of a person. I assumed they must just be waiting for someone, so I hopped out of my car and ran for the bathroom. It had been a hot day, so I was only wearing shorts and a tank top, but now the heat from the day was gone and the cold air caused me to shiver as I ran to the building. Once inside the bathroom I looked around but i

Last Updated : 2023-11-08

Jerking “Straight” Friend

I had just started my first year of college. Prior to this, I had only been with girls but I was definitely eager to try something with a guy. I quickly became close friends with this guy from my orientation Adam (18). He’s about 5’10, has curly ginger hair, wears glasses, and has the most dreamy blue/green eyes I’ve ever seen. Whenever we got drunk, he’d start asking me and my friends questions like how big our dicks were, how we lost our virginities, etc. All my other friends were weirded out by it but I was lowkey turned on. One night after drinking, we ended up alone in his room. He goes to lay down and I ask him to snuggle, and he responds “uh sure?” I climb onto his bed and spoon him, putting my head on his shoulder as I watch him scroll through TikTok. Eventually, I get hard and decide to put my leg on top of his, pressing my boner against his ass. He flinched and his heart started beating faster, but said nothing. A couple of minutes later, I put my hand on top of his shorts

Last Updated : 2023-11-21

My English Teacher

I am 24, while he is 37 and still teaches English at my old high school. He was always my favorite teacher he was always very nice, not strict and just a chill teacher I always did find him hot, he is 5'8 black hair and I am 6'6 brunette. It all started last month where I found him on Facebook and I friended him and he friended me back and we started talking about life and other stuff, he is divorced with his ex wife, while I am single he told me about how he is secretly bisexual, and I told him i was too. One day he invited me to watch some football, I had a big crush on him since high school and now he's right next to me, I started to get a boner and I tried to hide it but I'll call him Mike, Mike noticed it and he giggled saying "Is that for me?" I admitted to him that I had a crush on him since high school and he said "omg" and I said "I am sorry I always had dreams about us having sex and being together" and he hugged me and said "it's okay" and he grabs my ass, and says "let'

Last Updated : 2023-11-22

The Young Neighbour Part 1

I was hanging outside in my backyard one day bbqing myself a burger (I live alone). And the neighbor came over and starting talking with me, hanging out a bit. He lives with his parents in a duplex attached to mine. He's pretty cute, he's not like a femboy but definitely could be if he wanted, he's got messy light brown hair that's kinda long, short, skinny and an amazing ass. I offered him food, he said no he's gotta go home.Anyway, last Friday he came over like right after I got off work. He asked if he could hang out, I said yeah I was gonna have a beer and play some starfield. I offered him one and he just sat next to me on the couch drinking while I played, and we talked about the game blah etc. This is when it started to change, about an hour later and a few more beers in for each of us he started asking me about my job, if I have a girlfriend. Questions like that. Then he's like would you try anything with a guy? It was a weird question, I never even considered it before but

Last Updated : 2023-11-23

The Young Neighbour Part 2

He blew my phone up this morning and came over for sex before I went to work and had a shower, I invited him to stay while I was at work and we texted on and off all day, he sent me a pic of his butt at one point. Damn sexy. I came home to him naked on my couch and we sucked each other's dicks, I played with his balls alot. I've found I'm really into touching and sucking on them, I don't know how to explain it but they just turn me on a lot.We cuddled for awhile and we got into talking about where we want to take the relationship and he had a confession that his parents don't know he's gay and they can't know, I was honestly really surprised cause he's clearly been doing things with guys awhile, he's experienced af. Yet he did say he wants to be a couple, just to hide it in public, I did agree and I'm hoping that's the real reason. We made out for awhile and ordered some Doordash.We discussed plans for tomorrow (I'm taking a half day to boost start the weekend) that we would get so

Last Updated : 2023-11-25

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