[MM] My semi awkward experience with a chubby gay male | 2016

Warning This is a long post

This is my first time writing a story about an sexual event in my life with such detail so bear with me if it's bad. The story was longer than I expected it to be so i just made a bolded not where the sex talks place. I apologize if the writing is bad.

I consider myself to be quite an attractive male at times but my confidence is my kind of my weak point. To describe myself, I am a skinny (around 140 lbs) black male. I am average sized in terms of my cock but I still kind of think it's small (around 6 inches). Anyway at the time, I was 19 years old and still a virgin. I considered myself straight but I had a lingering curiosity towards certain types of men. Due to this curiosity, I found myself on porn sites like Xhamster looking up porn videos of really chubby males bottoming for slim tops and I'd be lying if I said it didn't turn me on quite a bit. I never masturbated so I'd always be leaving myself frustrated at the end of the days with my balls hurting. After a couple of weeks of this, I decided to go to craigslist after reading up on craigslist hookup stories on reddit to see my options. Me being a straight male, I naturally went to the w4m section and I made several ads for the section looking for a hook-up. I was flooded with a lot of bots and some gay men trying to seduce me but no women whatsoever.

As time went on I got more desperate and more lustful so I lowered my standards a lot and went down to the t4m section. I figured why the hell not since technically it would still be the image/appearance of a girl I was getting off to. That also didn't work out as a lot of them were prostitutes asking for money and I couldn't afford it so exhausting all of my options, I went to the m4m section but I wasn't going to settle for any guy. I wanted to find one that specifically fit my needs. Ideally I wanted a dude who had a really big soft ass and some semblance of tits. There were plenty of reposters who would post multiple time so I avoided those types as I felt they were the ones who were more likely to have an STD. I eventually found a guy who was pretty much as close as I was going to get for what I was looking for. He was a bald dude who was really chubby, his ass was really huge and enticing so I messaging him figuring that there was no harm. He responded back almost immediately and we kind of hit it off. At first we started feeling each other out to see if we liked what the other looked like. This involved a lot of sexting. I'd email him body and cock picks and he'd send me full body and ass pics. From there we began to plan out when we would meet.

Since I lived with my parents still at the time, it was kind of hard to find a day where I could be absolutely free to meet up. Fortunately I caught a break and I found out a day in advance where my mom and dad would be working for most of the day and my sister would be on a trip out of state so I had the house to myself on that day. I told the guy about it and he was excited that we had a day planned to meet. Leading to the day, there was a lot of sex talk about what I wanted to do to him and how he would please me in any way I want. It was at that point I let him know that I was a virgin and honestly he took it pretty well. I pretty much stated that I didn't really want anything more than to get a blowjob and fuck him. I didn't want to do anything intimate like foreplay or kissing as I felt that would really be crossing the line into an uncomfortable level. He was pretty fine with it and his only request was that I fucked him slow as he was really tight and couldn't handle a pounding. I wouldn't be able to provide a condom so I told him that and he said that he would bring one for me along with lube.

Finally the day came and my heart was pumping. So many thoughts were running through my mind and none of them were really about the sexy times to come. I was more worried about my parents coming home really early or someone else coming to the house uninvited and catching me red handed. The thought that this dude may be a murder or someone with an STD also came in my mind but I pushed those thoughts aside. I messaged him that I was ready to meet up and I gave him my address (I prolonged it until the last minute just in case I wanted to back out). It was around 12 and he said he would be there in an hour which was good. I spent the time by taking a shower and making sure I was clean. I had no idea what one wears for such an event so I just opted for a white t-shirt and grey cargo pants. After that I started to prepare my room before realizing that I really didn't want this to happen on my bed since I sleep there all the time. I was running out of time and I doubt he would have been fine with the couch so I opted to use my sisters room (it's despicable, I know). I took the covers off the bed and just put them away so I could put them back later when I was done. I had about 15-20 minutes to spare so I just sat down and browsed the internet on my phone until he came. I heard a door knock around 12:59 and I went to look out the window. There he was standing in a gray workers shirt, short cargo pants and beat up sneakers. He also had a bag in his hand which I assume had the condoms and lube. I quickly open the door and let him in. We quickly exchange hellos and I lead him to the room where we would be having our fun times.

The Sexual Part:

So we walk in the room and I close the door to make sure. Once the door close he immediately told me to take my pants of and he pulled his pants off and took off his shoes. I listened and I pulled my shorts down and my dick sprung out. He immediately groans once seeing it, he grasps it and gave it a little jerk before taking me in his mouth. I remember thinking "so this is what a blowjob feels like". I don't know what I was expecting but it wasn't that. I can't say it wasn't enjoyable but for some reason I wasn't feeling it. Even though I wasn't really feeling it, I felt like cumming right there but I tried my best to hold it back. After a couple of seconds of blowing me, he signals for me to lay on the bed and I do that. He takes his shirt off and he goes back to sucking. He ends up pausing and when I look down to see why I notice that he started to kiss up my body from my stomach to my nipples where he gave me a little bite. I also didn't enjoy that (which is weird because this is something I'd very well like a woman to do for me even to this day).

I let him nibble since he seemed to be enjoying himself and then he stops and he asks me if I like to kiss to which I reply with a flat out no before apologizing. He was cool about it and he didn't push at all. He pretty much slides his huge chubby body over me to go back to my cock and I will admit that felt great. Something about the soft body contact since he was smooth all around made my cock twitch which he took as motivation to suck me more intensely. I start getting into it so I put my hand on his head as he was really sucking and licking on the head of my cock. I wanted to see if I could make it feel better so I ask if he could suck my balls and he responses with "oh yeah baby, ill suck your balls". He starts licking on my balls and sucking on them and surprise surprise I didn't like it because I felt he was doing to hard but either way it seemed to trigger something in me. A weird moan/grunt escaped from my throat and I immediately start cumming. He was surprised that I came so quick (it probably had to be like a max of 5 minutes since we started) but he went with the flow and started jacking me off faster until I let it all out.

I look down and I see that there is cum all over me. I know what cumming felt like since I used to be and still am at times prone to a lot of wet dreams. I couldn't help but feel disappointed because I thought it would feel much better. I started to think if it would be different with a girl I liked. My thoughts were quickly put away when I looked him lick my cum clean from my body and cock. I may have not enjoyed the blowjob as much as I thought I would but seeing that sight was something that made me feel really great. When he was finished cleaning me, he asks me if I think I will get hard and cum a second time to which I reply with an "I don't know but you are free to try and get me hard again". So he starts sucking me again and for a while it's just silence. To start conversation I assume, he says that I came so much and that he was shocked that I started to cum so much so quick since he was out of position sucking my balls. I didn't really know what to say so I just told him that it happened because he was a pro at oral and he smiled at me before going back to sucking my cock. I notice that I am not getting any harder and I start to think about whether this experience has been kind of lackluster because I wasn't really into the whole gay sex.

I'm once again pulled from my thoughts when he tells me he has an idea and I tell him to go for it. He then goes over my body again like he did earlier but instead he stays over me. Now we both were in the 69 position with his ass over me. Now I wasn't going to eat his ass or anything and I wasn't thrilled that his cock was pretty much resting on my chest area but the body contact was something that felt a bit nice so I started to get hard again. He immediately notices this and proceeds to start sucking he as best as he can. At this point I feel like I should be doing something so I start feeling his ass and I can feel him rubbing his stomach on my chest. I kind of got the feeling he was enjoying it so I took a chance and I slapped his ass and he moaned. The moan was kind of like a deep moan but I could hear that pitch that kind of sounded like he was moaning like a girl. So I slap his ass again to see if he will moan like that again and he starts moaning more feminine like which I really enjoyed. At this point he starts really getting into the blowjob and I squeeze his ass before I start rubbing my finger around the edge of his asshole. I asked him if it was ok for me to finger him and he said it was fine so I started to finger him slowly with my index finger. It felt weird but I kept doing it hoping that he'd like it. I remember feeling weird being silent while he was moaning so effeminate like so I tried my attempt at dirty talking. I say out while fingering him "You want me to fuck your tight hole hard" (I felt so weird and was internally cringing when I said this), He mumbles without pulling my cock out of his mouth with a firm no and that he was too tight. That put an end to the dirty talking haha.

We go on like this for a while longer and then he asks me if I am getting any closer to cumming. I wasn't (I actually was losing my hard-on) so I told him that I wasn't. He goes on to state that he really wants me to cum from his mouth again before we go to topping. At this point, my mind is racing not because I am getting excited but it's racing because I realize at that point of time that this is not really what I expected and I actually wanted it to end as soon as possible. So I make up a lie that I need to check my phone to see the time. I get up and he says that I could try jerking off over his ass to try to cum and that I could rub my ass over his crack. Me being the dumbass who's never jerked off tried doing it and I know it's not going to work so I just flat out make up a lie that time is running out and that he has to go. He looks at me once and he say ok. He puts his clothes back on and he takes his bag of condoms and lube (that we never used mind you) and he walks out of the room. He asks to wash his hands and I lead him to the sink. He washes his hand and he leaves after saying bye.

Sex ends

I still being naked immediately take my clothes and put it in the washing machine and I go straight into the bathroom to take a shower and pee. I remember spending an abnormal amount of time cleaning my penis and my finger that I penetrated him with. After that I had to set up my sisters room to what it was before I had sex in it. That wasn't much of a problem since I am ridiculously good at making a place I interacted look the exact same it was before I interacted with it. I ended up spending my day playing video games to which my parents come home about 5 hours later. I felt that I kind of disappointed him since I only ended up getting oral/fingering his ass and left him hanging but it really wasn't what I thought having sex would be like so I couldn't let it go further.

This was my first sex experience and it was the first of two experiences where I succumbed to my curious lust to engage in sex with a male. Although I didn't really like this time in the moment, this was the better of the two as the second one (happened months after this) was god awful. This experience did stay with me quite a bit and it kind of lead me to my second sexual experience with a male stranger. If people really like this post and/or want to hear about my other experience then I will post it as well but I am ending it here.