My story begins with me visiting my next door neighbor, Charlie. Charlie has been a friend since high school. He owns a 3 bedroom house with a pool/jacuzzi setup in the backyard. It's a small yard so the pool is the focal point. Charlie lives with his wife Karen and his young dog Othello. Often, Charlie will ask me to watch his dog. Since I live right next door with my parents(it's a long story), it's never an inconvenience to watch Othello. I actually very much enjoy spending time with him. We bonded early on when Charlie and Karen first got him as a puppy, which is why they prefer I watch him. The purpose for this visit was to show me what small changes they had made to his diet and orientation of his toys, and food and water bowls. They had a long weekend planned so I was going to be watching Othello once again.
Whenever Charlie and I get together we always end up talking about everything we did since we last saw each other, and we are quite loquacious. So we sat down and talked about work, about his in-laws, my relationships(or lack thereof), and our favorite video games. On this day I was feeling especially chatty, so I lost track of time and found myself still there when his Samoan friend, Tim, came by. Now, I had never met Tim before today, but he seemed very nice and pleasant to talk to. To give you a short description, this man was a 6' 4" chub. His legs were thick. Nice muscular calves topped by thighs as large as tree trunks with a pleasant layer of fat. His ass was wide with a nice bubble shape to it. Instead of having a large gut, like most chubs, his stomach was relatively flat despite having a generous, and evenly distributed layer of softness. His hair was black, long, and curly. His Face was handsome with the signature Polynesian nose, a strong chin with a nice 5 o'clock shadow forming, but not so thick a facial hair as to imply him a hairy man. I'll be honest, he was a pretty good looking guy.
In contrast, I am 5'9", average build, meaning I have muscle definition every where except my stomach. I'm a little out of shape. But, legs are slender and muscular, and my arms are well defined. I'm a generically handsome European white male. I've always felt average described my physique perfectly. Average height, weight, 175 by the way, cock. I think I'm you get the point.
Tim immediately joined Charlie and I in our inane conversation and soon we were all laughing and having a great time. As time passed and I got to get more familiar with Tim, I started picking up subtle hints implying he was gay. It seemed he really wanted to know more about me than talk to Charlie, which made me think he was attracted to me. He was slightly flirty with his comments and jokes. Admittedly, I was also feeling a little flirty ever since he showed up, something I tried to play close to the vest, but I'm sure it was a failure. I didn't make it known about my sexual orientation so he would keep giving me attention. I was definitely enjoying it, but I still wasn't confident he was gay nor if he was into me. I only had subtle clues that could easily be misunderstood and a growing desire to find out.
Finally, Charlie invited me to see his new outdoor patio lighting he had overlooked during our catching up. So we made our way to the sliding door to see the new lights he had hung above his patio. They were nice. Karen was especially happy with them since they allowed for wonderful night time lighting while entertaining guests. Karen, Tim and I opted to remain inside while Charlie explained his excitement and demonstrated the illumination his new lights provided. While I was peering out the door, Tim made his way behind me because Karen was beside me so we were blocking the way... no big deal since he was easily 6 inches taller than me and Karen. So, he had a good enough view. I thought nothing of it, but I was definitely aware of his presence and position directly behind me. As he approached me from behind he rested his hands on my shoulders, but he immediately tried to cover it up by drumming awkwardly on my shoulders before moving to Karen and doing the same. That was all the confirmation I needed. He had let his passion Control his actions and his curiosity get the better of him for just an instant, but that was enough time for me to figure out he was definitely intrigued by me. Since other people were around, I played it cool as if I didn't notice, just to help him save face. But I smiled to myself. I also kinda wished he would come back. I realized later that I missed an opportunity by not inviting him to touch me some more.
For the next hour I tried to keep my intrigue for him under wraps. Something you should know about me, I'm straight. I date women and only women, but after divorcing my ex-wife, I watched a lot of anal porn and was convinced it would be enjoyable. So, I tried it and found it thrilling, but I convinced myself I couldn't really experience anal sex without doing it right. So, I found myself aroused by watching gay porn. Not just any gay porn, but chubby gay porn. Something about those bellies and plump asses just turned me on. So, I accepted my fated identity as a chubby chaser, not just of women, but men too. I eventually got the courage to seek out other men who might be interested in having sex with me. It wasn't hard to find someone to have sex with, but it was difficult to find a chub. They weren't as prevalent on the internet as twinks and BBCs. So it took a little time, but I found one. He was very hot, but also very shy. It took me a few tries and a few guys to get there but eventually I got to try anal sex. My first couple of times were clumsy at best. But, I eventually had an encounter with a really hot chub that had the gift for making me feel comfortable and pounded my ass with multiple loads in one night. This experience made me feel more confident as I was learning how to enjoy anal sex. I saw something similar in Tim, therefore you can see why I was interested.
My mind began working. How could I get Tim alone but not make it seem suspicious. So I decided to pretend that there was going to be a lull of about 8 hours where I couldn't take care of Othello. 8 hours was a bit too long and risked an accident in the house so someone else would need to help cover that time. I didn't want to admit my parents could do it so I turned to Tim and asked if he would be able to help me out. I told him that I would be there when he arrives so he wouldn't need a key or the alarm code. I said my window was flexible so I could work around his schedule. My excuse was errands... an easy and vague excuse. Tim thought about it, obviously trying not to seem too eager. But Charlie said he had someone else he could ask before Tim's feigned hesitation was over. I gestured toward Tim and said to Charlie, "well he's right here and hasn't answered yet, so let's see what he says so you don't have to make another call." Thankfully, Tim said he could and even gave me a window of 4pm to midnight that he would be available. With that all ironed out and my plan in motion, Charlie approved and we called it a night.
Unfortunately, it was three days away. I was excited. I decided I would gradually build up to letting him know that I liked having sex with chubby men. But, I was going to have fun getting there. I made sure to wash all my clothes so I'd have everything at my disposal. I wanted to plan exactly what he would see and when. I had a loose plan in my head.... very loose. With all these plans going through my head and playing out scenarios, I was getting incredibly turned on. My hand was involuntarily rubbing my cock every time I thought about Tim. I eventually had to hide away in the bathroom at work to rub one out. I unzipped my pants, grabbed my cock and started stroking furiously. I tried to imagine Tim grabbing me from behind and plowing his hard shaft deep in my ass. The image and phantom sensation of a dick in my ass made my cock extra hard and I could feel that this wasn't going to take long. I continued my fantasy and jerking while imagining it was his hand stroking my cock and fucking my ass. I wondered what his breathe would feel like on my neck and how his hands would feel against my skin. I wanted desperately to know how it would feel having my ass cheeks press into his chubby pelvis and maybe feel his balls slap against my taint. The image was too much. With the desire to feel him inject my hole with his warm sperm, I began to cum... hard. I sprayed everywhere in the stall. It felt amazing, but was slightly ruined since I had to clean it all up. I'm not an asshole. Afterwards I was free of the tension for the rest of the day, but I knew it would come back with a vengeance tomorrow.
On Friday, Charlie and Karen went on vacation leaving me alone in their house. So, I prepared the space for our fun adventure. I vacuumed everything in sight. I wiped down all the dusty spaces, and swept all the floors. Othello was restricted to his bed while in the TV room, which is where I predicted everything would go down. I can't tell you how unattractive animal dander can be when you're trying to fool around. I made sure to have my favorite lube handy, that way there's minimal interruption to our play date. I had my bag of toys ready just in case we required a warm up... which sometimes was nice. Beside the couch, I placed a couple of towels and a sheet to protect Charlie's couch from any stray bodily fluids. I rummaged through all my favorite shirts, shorts, and pants. The only decision I actually made was to find a reason to change into some camouflage booty shorts I owned so I could show off my assets. I figured that would be easy to do because it's summer time and the heat was unbearable.
Saturday afternoon finally rolled around. At 1pm I began my prepping routine. Since most of you have had anal sex yourselves, you're aware of the necessary pre-game rituals so I won't go into those nasty details. Some things are better left a mystery. I decided to keep it casual and play it coy. I was in shorts and a t-shirt, and that's it. I figured a good pair of basketball shorts would show that I was just lounging all day so I didn't need to hurry, and going commando might give him a good look at the outline of the tip of my dick. I also wore one of the t-shirts that fit me perfectly, showing off the definition of my arms but still showing my tiny belly. With my outfit carefully crafted and selected, I watched TV while I waited... and waited. Time ticked by excruciatingly slowly.
4Pm Saturday afternoon. I started getting butterflies in my stomach from anticipation. Tim was due soon and with the anticipation taking over I was running scenarios in my head of how I would make up excuses to change my clothes or why I didn't actually need to leave. But, I figured I'd make it up on the spot.
The doorbell rang.
I answered the door to see Tim apparently freshly showered. He looked sexy with his baggy shirt covering his girth and his shorts emphasizing his round buttocks. I said hi and invited him in.
Tim asked "so what errands you gotta run today?"
I wasn't expecting that question so quickly, I hadn't anticipated his natural desire to inquire about someone's life. I had to think about my reply for a minute.
"I actually found some free time on Thursday to handle most of it. And I didn't have your number to let you know. I hope that isn't a major inconvenience. I'm sorry I didn't try harder to contact you and let you know I didn't need help after all."
That was good, some of it had been rehearsed. I was hoping he wouldn't be upset.
He turned to me and said, "Oh, that's ok. So you don't need me after all. Should I just head home?"
"I feel bad having you make this trip, why not just hang out for a bit so it isn't wasted?"
"Sure" he said eagerly. Maybe a bit too quickly, too.
