The Parking Lot Experience

I've been known to take chances in life that haven't worked out so well, but the events of a recent warm summer evening remind me that when things do work out, they can be amazing.

While I've spent the past 10 years experimenting with my sexuality and never quite being able to comprehend how a man who loves the female body can still be obsessed with the feel of a nice hard cock. It's this obsession that had me cruising Grindr in hopes of finding someone in my area to fool around with. It had been a couple of years since my last experience while away on vacation and I was getting that urge again.

I live in a relatively small city, so I knew most of the Grindr regulars and had no problem identifying the ones that I was going to ignore either because they were habitual no shows or because I had chatted with them before and knew we weren't going to be a good match.

I wasn't having much luck and decided to go for a run to wear off a little energy and enjoy some alone time away from the family. I left the house wearing my usual running gear with no thoughts that I was about to embark on a life changing adventure. I was only a mile or so into my run when my watch showed that I had received a message on Grindr. Normally I would just keep going and check my messages after the run, but I decided to take a quick break and see if anything good had come in.

I retrieved my phone from the running sleeve I keep it in and saw the message was from someone I had never chatted with and hadn't seen on the app before. It was an innocent message, asking how my day was and what was I looking for. Nothing out of the ordinary, but enough to pique my interest. I replied and said I was married and looking for someone to fool around with, but not looking for any kind of long-term relationship. I said I had a bit of experience but hadn't been with another guy for a couple of years. I also told him that ideally, I wanted to find a regular sex buddy to meet with every once in a while but wasn't looking for any kind of relationship.

We chatted back and forth and in 15-20 minutes of conversation I was sitting in the parking lot of my kid's school enticed by what the other guy had to say. He was in the same position as me at my stage of life, but his marriage had broken up and he was now exclusively into dating men (which he said hadn't been successful as of late and he really needed to hookup). I was a few year's out of a regular hookup with a fully gay man that didn't end well because he wanted more than a casual hookup, so I was a little reluctant to pursue this adventure, but as we chatted I began to feel like I really needed to meet this guy.

I told him that I was out for a run and if he wanted to meet up and chat some more, I could run around the track at the high school until he showed up. He only lived a few minutes away, so he said he would come over and we could meet. I ended the conversation and started to jog towards the track which at that time of night was usually empty. Unfortunately, I didn't realize that a men's soccer league had just wrapped up and there were a dozen guys sitting in the parking lot adjacent to the track enjoying a few post game beverages. I wasn't sure how this was going to play out and whether the other guy (Andrew) would be frightened away by all the people there.

As I finished up the second mile around the track, I saw a truck pull into the parking lot and drive past the entrance to the track. I figured it was probably Andrew and all the extra people around the track had scared him off. Part of me was ok with it, as I didn't really want to be seen with this other guy and wouldn't have an explanation if I knew any of the guys (it's a small city) and they asked what I was doing there with Andrew.

I found out I was partially correct about Andrew driving past, however instead of being scared off, he decided to park his truck out of sight and walk over to the track.

As I was running around the track, I noticed a guy approaching from the back entrance and saw that he matched Andrew's description. Older (55 to my 38), a nicely trimmed beard, average height and a few extra pounds that come with age.

I continued to run around the track until he entered the running surface and said hi as I was passing him. I slowed up and introduced myself as we began to walk around the track and chat. The conversation flowed naturally and within a few laps of the track we had hashed out what each of us was looking for and agreed that we would like to meet in a more private setting next time, where we weren't in public and didn't have a dozen soccer players to deal with.

I had been out of the house for close to an hour at this point and my wife and kids would be expecting my home sooner than later, so I told Andrew I would walk him back to his truck and then I had to get going. As we walked around the truck, there was a storage shedding blocking the view of any of the soccer players and Andrew took advantage of the situation to pull me in close to him.

For the first time in my life, not in a private setting, I leaned in and kissed another man. It was a soft tender kiss to start. Just brushing our lips against one another as we got a feel for how far this was going to go. The heat was quickly turned up though and I found myself unwilling to pull away from this guy. I felt his lips open and took the chance to slide my tongue into his mouth, probing to find his tongue and drawing it into my open mouth. I put my hand on the back of his head and pulled him into me, I didn't want him to pull back and I wanted to feel his tongue probe my mouth as deep as it would go.

As the make out session escalated I began to worry about the fact I was so sweaty after having been running and hoped that my current state wasn't enough to turn him off, but luckily it seemed like the sexual attraction was enough to overcome any issues he might have had.

We continued to make out and both of our hands started exploring, first with grabbing each other's asses and pulling ourselves in to each other. I could feel his hard cock pressing against by stomach and knew that I had to feel it and see if it was as big as it felt. I reached in between us and discovered that like myself he wasn't wearing any underwear under his shorts, making it easy to access his big meaty cock. He was about the same length as me 6 inches or so, but so thick that I couldn't get my hand fully around his shaft.

As I reached into his shorts and started stroking him, I could feel his body give into me and vibrate as I pulled longingly at his thick member. We were still kissing and he couldn't stop moaning as I worked my hand up and down his pole. After a couple minutes of stroking him, he suddenly grabbed my hand and said I had to stop that he was going to cum. At this point, I really wanted to make him cum, but he had other ideas.

He took a step back from me, then said it was his turn to discover my cock. He reached into my easily accessible athletic shorts and I just about fell as my knees went weak from his incredible touch. He was stroking me in a soft rhythm, bringing me close to orgasm, but never quite getting me over the edge. This guy knew exactly how to work my organ and I was putty in his hand as he repeatedly brought me close to cumming but wouldn't let me go over the edge. After a few minutes of this, reality of where we were suddenly kicked in as a set of headlights passed by us from one of the soccer players leaving. I could have taken this as an opportunity to shut things down and get home, but I just couldn't pull away and let him keep playing with my dick while taking a chance of getting caught by the rest of the soccer players whose vehicles seemed to all be passing now.

After the last car pulled out and we had the parking lot to ourselves, Andrew made a bold move. He pulled the tailgate down on his truck and turned me so that my stomach was up against it. Then he pulled my shorts down and bent me over the tailgate as he started rimming my asshole. I wasn't expecting it, but pleasantly delighted as his tongue worked itself around my rosebud. Then his mouth pulled away and was replaced by a finger slowly gliding into my puckered hole. At first it was a little tight, but as I relaxed he was able to glide smoothly in and out and after adding some more spit increased it to a couple of fingers. I was panting like a dog as he worked away at my ass, almost making me cum without touching my cock. I had only experienced anal a couple of times in my life and it wasn't something that I normally needed, but at this point I was really hoping he would stick his swollen cock deep into my ass.

I'm sure he could feel my willingness, and as he pulled his fingers out of me, I could feel them being replaced with his much larger cock. He started just rubbing it up and down my slit, essentially asking my permission to continue. Without any spoken words he knew I was giving permission when I pushed back against him and then I made it real clear as I grabbed hold of his shaft and guided the head of his cock into my opening. I'd love to say it slid right in, but it was a bit of a process to take his thickness, so he worked slowly and gently, adding lots of spit until he was able to bottom out with his entire length inside me. As he gently started thrusting into me, I started pushing back and getting him to increase his pace. I was in love with this cock, as it hit all the right spots inside of me and started sending me into a different atmosphere. It felt so good I was close to blacking out and knew that I would cum with just a couple strokes of my cock. I wanted to feel him deposit his seed in me and asked him to fuck me harder and fill me up. I could feel his orgasm building as the pace of his thrusts slowed but became much harder. He was balls deep inside me when I felt the warm gush of cum start filling me up. As his load hit me, I reached down and with just a couple of strokes I blew streams of my own cum all over the pavement below me.

With both of us attaining our release, I jumped back to reality and realized that I really needed to get home before my family started wondering why I wasn't back from my run. As much as I wanted to stay and play a little more, I knew it wasn't going to happen, so made a quick exit, pulling up my shorts and starting to run home. As I ran I could feel his cum leaking down my leg and knew it was a good thing that my wife would expect me to jump into the shower as soon as I got home.