Jeep Guy - My First JO With A Man

I was a virgin when I got married to my wife over 20 years ago. This was something I worked hard to achieve as, like most young men, I had (and have!) a strong sex drive but valued maintaining our virginity.  Although I was a virgin and attracted to my wife sexually, I also had a strong sexual attraction to other guys growing up and this remained true into adulthood. In fact, 95% of my jerk off fantasies while growing up included males (real and imagined). 

After being married for a couple years I completed grad school and my wife and I moved to a new state where I would begin my first real job. We had sex at least daily for the first year and multiple times a week thereafter. However, when able I would still watch gay porn and masturbate between times with her. She would occasionally leave for a weekend to go visit her parents out of town and I would stay home, having ample time to watch porn and jerk off, typically 3-5 times a day!  

My first sexual encounter with another man happened one weekend when she was away. I was bored and super horny that Friday night and recalled that I would often see some “intriguing” activity at the park nearby when my wife and I would take walks. I would occasionally notice men driving back and forth through the park, alone in their cars. I also noticed some of these men would tap their brakes when passing each other but unsure why they did so. Over time I put together this was some kind of signal of interest to one another. I would see men pull into parking spaces and then shortly after another car with a single man in it would pull into parking spaces next to the first, or two cars would follow each other out of the park. I’m pretty good at piecing things together and quickly figured these were either drug deals or hookup for sex. That Friday evening I was so horny that curiosity won and I drove down to the park, heart pounding and shaky throughout. I made several passes through the park and noticed I had several cars pass me and tap their brakes, seeing their brake lights in my rear view mirror. I got up the courage to return this signal a couple times when the guy during the oncoming car looked decent. I was so nervous but horny as hell resulting in a raging hardon that I was rubbing through my shorts. I’m a heavy pre-cummer and could feel the wetness leaking down my inner thigh. 

After a few opportunities of men pulling up next to me when I would stop and then chickening out and driving away, I finally rolled down my window when a decent looking guy about my age driving a Jeep Wrangler pulled up next to me. His Jeep had no doors so I could look straight in and see his full side view. Nice looking. Average but attractive build. I am thin and have a runner's build but have always been into thicker athletic guys with muscular arms, chests and legs. This guy, I could see, had nice legs as his shorts were hiked up a bit from sitting. We made eye contact and his hand went to his crotch. This was clearly not an attempt to sell me drugs. My hand went to my hard dick inside my shorts. He gestured with his head to follow him. I paused and almost panicked but decided to see what would happen. He was staring at my hand working my cock but when he looked back at me I nodded and smiled. He backed out and I followed him out of the park. I followed him to a nearby remote part of a store parking lot. It had gotten dark by now. We parked and he immediately got out of his Jeep and climbed in my car, not leaving me a chance to chicken out!  We talked little. He reached over and began massaging my dick through my shorts. My precum was flowing. I put my hand onto his thigh and caressed his thigh and then slid my shaking fingers under the hem of his loose athletic shorts. I remember how exhilarating this was. His legs were strong and thick. I recall how his hairy thighs felt and then brushing his balls as I explored further. He then abruptly tugged his shorts and underwear down to his ankles, sitting bare-assed in my car. He started to go for unbuttoning my shorts but I intervened and opened them for him, sliding them down low on my hips. This allowed my raging hard 7inch cut dick to spring free, precum dripping down my shaft.

I was so horny and nervous and excited. He grasped my slippery cock and started stroking slowly. I reached over and slid my fingers into his pubic hair at the base of his cock. I have always loved the coarse feel of a man’s bush.  His was trimmed pretty short but thick. I slid my hand understand his balls which were warm and a bit sweaty as it was a summer evening. They hung loose under his hard dick that pointed straight up. I cupped and caressed his balls as he continued to stroke my cock and fondle my balls, neither of us speaking or even making eye contact. I worked up the courage to slide my hand around his cock. This was the first time touching another man’s penis and I was so turned on by this encounter.

I was disappointed that rather than the monster dicks that I enjoyed masturbating to in porn, this guy’s tool will was quite small but rigid as iron. I began stroking it nonetheless and completely enamored by the feel of a man’s dick in my hand, the sounds and movements he was making in response, as well as the electrifying sensations coming from his strong masculine hand sliding firmly up and down my shaft. I took breaks from stroking to run my hand up his stomach and chest, once up to his jaw and neck, feeling his rough stubble and noticing that he was quite good-looking. Then groping his balls and inner hairy thighs before returning my hand to his raging, but slight penis which was now dripping and throbbing in unison with our pounding heartbeats. 

We continued this silent, anonymous pleasuring of each others’ manhoods for only a few more minutes before we both began breathing faster and increasing the tempo of our strokes. It was clear this stranger was going to make me cum and I wanted to experience his orgasm first in case I came first and then chickened out with post-cum clarity.

I focused on working his small slippery cockhead which he clearly liked. He began fucking my hand, lifted his ass off my car seat and trembling.  While holding the base of my cock in his hand he started to cum. Gasping and swearing, his cum flowed from his piss slit  in waves down over my stroking fist and over his tight balls. The feel of his hot jizz on me was so arousing. I held on to his cock as he resumed fisting my cock with a clear goal now.

Feeling his softening dick in my hand and his sticky cum coating my fingers and the sound of his hand sliding up and down my precum soaked dick sent me over the edge. “I’m gonna cum,” I whispered. “Don’t stop. Keep going.” And I began erupting several ropes of thick milky cum into the air and onto my stomach, pubes and down his pounding fist. “Keep stroking,” I begged as my orgasms tend to last quite awhile and I like to keep stroking until the pulsing ends and the last drop of cum is released.

We let go of each others’ cum-coated dicks and sighed. He pulled restaurant napkins from his pocket, clearly prepared for what he set out to accomplish. We wiped ourselves clean and pulled our shorts back up. We muttered awkward pleasantries and he got out of my car and climbed into his Jeep. I drove home overwhelmed by guilt about what I had just done. I took a thorough shower and vowed I would never do that again.  A couple hours later I was getting ready to climb into our empty bed and noticed how horny I was already feeling again. The events of my first encounter with another man replayed and I could not help getting hard. In bed, I began stroking my cock and cumming to the replay of my time with the Jeep Guy.