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.
Now that I had him I decided I’d begin my slow and clumsy seduction.
“I was watching some TV, would you like to join me?” I asked.
“Sure.” he replied
We sat and started watching TV. We watched for an episode, chatting about what we liked and didn’t like about the show. We sat on opposite ends of the couch, obviously because of unfamiliarity with each other. Throughout the episode I got up a couple of times for water and snacks and every time sat a little closer, but not too close as to draw suspicion. He got up and came back and was noticeably closer too.
Eventually, I asked him if he was hot. I had closed the register to prevent the a/c from getting directly in the room and said I didn’t know how to use the fan so I couldn’t turn it on. He said he was a little warm and I agreed. I said, I’m gonna go put something cooler on and see if I could find a fan. I excused myself to the bathroom and stripped down to nothing. I had a tiny pair of shorts hiding in there and slipped them on. I walked out in my short shorts and no shirt, and watched for his reaction. His eyes got a little wide at seeing me in basically underwear and the search for a fan was completely forgotten.
He said, “wow, those are short… and tight. Are you even wearing underwear under those?”
I could see the eagerness for a specific reply which he tried to cover up with nonchalance. I obliged.
“Well, I wasn’t wearing any before so I didn’t think to put any on. Besides, they’re over at my house”.
So began my tease. I walked like I was on a cat walk, strutting my stuff joking around with him like I would with any other guy. He eventually decided to remove his shirt since it was warm. He was nice and smooth, with great curves. His pudgy frame was so attractive. A hairless stomach that looked nice and jiggly. His skin looked soft and inviting. I wanted to rub my moderately furry chest against his. His chest was graced with small mounds peaked by brown nipples that were perfectly proportioned to his size. My mouth began to drool. In all my wanderings and teasing I came across the fan controls and couldn’t feign ignorance anymore.
“I found the fan controls,” I said.
He laughed and said “aww, does that mean we have to put our clothes back on? I was just beginning to enjoy seeing you in those shorts.”