Author's note - The prologue to this story is true and happened almost exactly as it's written. The rest is a current fantasy I've been having that I hope might happen someday. Anyone want to sign up?
Prologue
I sit in my living room staring out at the large snow drifts that had piled up almost to the window. My wife has escaped the cold, choosing to spend January and February with her sister in Florida. In the weeks leading up to her trip I was excited by the prospect of being by myself for an extended period of time. Since I retired I spend each morning in my man cave watching porn and interacting on Skype with mostly male friends I've met online during the last few years. Hearing them comment on my body during group chats is always fun but if I'm being completely honest, the novelty is wearing off.
Many of these friends live within a couple hours of me and I often thought it would be fun if one of them could make a road trip so we could meet in person. I've only had one interaction like this around 10 years ago and it was ok but very risky. His name was Dave and we'd met on chaturbate where we'd watch each other jack off many times. He lived about two and a half hours from me and kept talking about meeting up someday. Since I couldn't just leave the house and hook up with the wife around I told him the timing wasn't right. The door opened when my wife made plans to visit her parents for a week without me.
I messaged Dave right away and we started making plans. Initially he suggested we meet at a rest area that was a halfway point for both of us but rain was in the forecast so he suggested a parking ramp at the casino just east of the rest area. I knew the road well since, ironically, it was the same highway I took to my in-laws. I told him that worked for me so we agreed to meet there Saturday at 11am. It was around midnight and I was pretty worked up so I messaged Dave and asked him to get on chaturbate so we could jack off together. At first he didn't want to because he worried that he wouldn't be able to cum on Saturday but I convinced him.
I was already naked and hard so I went online to meet Dave. He was rock hard as well and it didn't take long for both of us to cum as we talked about sucking each others cocks the next day. My entire body seemed to tingle in anticipation as I said goodnight and went to bed. I had a hard time falling to sleep with images of tomorrow running through my head but I eventually nodded off and woke up refreshed on Saturday.
I shaved and showered so I'd be nice and fresh for Dave then went downstairs naked to get a cup of coffee. My cock was beginning to be a problem because it was constantly hard now and I wanted to jack off really bad. I managed to resist the urge and went back upstairs to get dressed. Since it was the middle of summer I wore a white t-shirt and a pair of loose shorts with no underwear to ensure easy access to my cock.
After finishing my coffee it was time to head out for my first ever experience with another man. I figured it would take around an hour to get to the casino and this stretch of highway was pretty boring so I pushed my shorts down around my ankles so I could play with myself a little bit while I drove. My cock was rock hard for the entire trip which made it seem to go faster. The casino came into view ahead so I pulled my shorts up and took the exit.
Parking was free so I entered the ramp and made for level three which was where Dave said he'd be. I looked for his silver Camry but I couldn't find it so I pulled into an empty space away from other cars. Then I saw him walking up to my SUV.
He was a little younger than me, medium height and a thin frame with thinning hair and glasses. He had a mustache which didn't thrill me but I wasn't looking for a boyfriend, just someone to suck my dick.
"Hey man," he said, "I saw you drive by a couple times."
I said, "I was afraid you weren't here," as I pulled my shorts down, freeing my dick as he got in the car.
"Holy fuck your cock looks even bigger in person than I imagined it would," he said as he started stroking me. He pulled his shorts down and I started stroking his cock as well. When he was hard I realized his cock was no more than 4 or 5 inches. It always seemed a bit bigger on cam but that must have been due to the position of his cam. I was a little dissapointed but decided to make the most of it.
After stroking our cocks for a while Dave said, "I need to suck that big cock now Tony but I need you to wear a condom."
"Why?" I asked. "I've never been with anyone other than my wife."
"I can't take any chances Tony. I'm sorry but I'm gonna make you feel really good."
He tried putting a condom on my cock but it was too small. He had a bigger one that he slipped on then went down on my cock.
I always wondered if getting a blowjob from a guy would be better since we should know better than anyone how to please a man. Honestly it felt pretty good but I hated the condom. After a few minutes I leaned over and started to suck Dave's cock without letting him put a condom on. He tried to object but I held his cock firmly in my mouth until he gave in and moaned in pleasure.
"Mmmm that feels so good on my cock Tony," he said as I moved my mouth slowly up and down his little dick. I couldn't believe I was actually doing this and started sucking harder and faster. I can't really describe the feeling of having a hard cock in my mouth but it was certainly exciting.
Dave continued stroking my cock while I sucked his dick then he said, "Shit someone's coming."
I sat up and we both adjusted our shorts while an elderly couple made their way to their car without even looking at us.
I said, "So what do we do if security comes to check us out."
"Just tell them we're waiting for a buddy," he said. "Worst case we'll have to go play the slots for an hour. Right now I need that cock in my mouth again."
I pulled the condom off and said, "If you really want my cock then you need to suck it without a condom," as I pushed his head down and shoved my cock in his mouth. I started humping his face hard and cried out, "Oh fuck yes Dave. Now your mouth feels so good on my cock."
After several minutes of pounding Dave's face I took his cock back in my mouth. Each time one of us would suck each others cock we'd stroke the other one, making it a wave of constant pleasure. Now that the silliness of the condoms was gone I started to really enjoy myself. No-strings sex is a big turn on.
We continued on this way for close to an hour. I was sucking Dave's cock when he cried out, "Fuck I'm getting close Tony."
"We need to cum at the same time," I said as I got on my knees and shoved my cock in Dave's mouth. After pounding his face like this for a few minutes I could feel my own orgasm start to build so I sat back down. "Let's jack off together and get to the edge then we can stroke each others cock as we cum.
"That's just what I was thinking," Dave said. "Watch me stroke my cock Tony, mmmmm."