It’s the thrill of the hunt, the anonymity, the exposure, the wild nature that is cruising. Some call it cottaging or dogging, I call it a good time.
This is a story about my first time and this series will be my real life stories of the best and craziest cruising experiences I’ve had. I hope you enjoy.
My introduction to cruising was when I was really young, I was in my early teens when I had been talking to this guy online. I had set up a profile on manhunt . com (before apps existed). I knew I was gay from a really young age so I was ready to explore. His name was Mark and he was forty something, yeah I liked older men (I have daddy issues but that’s another story for a different time). He was a stocky guy with a thick cock. Even though my profile said I was eighteen he knew from photos I had sent him that I was younger. I was not slim but not overweight either. Tiny belly and plump ass with barely any hair on my body.
He would always ask when can we meet and I was always too scared so would make excuses and then go offline.
One day I came home from school and I was so horny. I jumped online and sent a message to Mark saying I would like to meet and I’ll be at deepwater park at 8pm. I showered and cleaned my ass thoroughly. Being so young I didn’t have any sexy jock straps yet so I put on tight black briefs that I had a feeling Mark will want to rip off, I had footy shorts and a tank top on. The most revealing clothes I could find. I snuck out after dinner which I didn’t eat to keep myself empty and ready. The park was a couple of mins walk, I was nervous and jittery but couldn’t stop rubbing my dick in my shorts
I finally got to the park, it was a spring weeknight and it was eerily quiet. There was a playground in the middle and trees all around with picnic tables and bbq areas. I found a picnic table that was covered by a lot of trees and sat on the table. I checked the time on my watch, it said 7:57pm, I waited. At 8:15 I thought he wasn’t going to come and then a cars headlights pulled up in the empty car park, they went dark and a man got out, I could only see his silhouette, he looked much bigger than me. I moved down onto the bench seat as he began walking into the middle of the park he was looking for a glimpse of life, I coughed and he moved in my direction. As he came into view I could see he was wearing cargo shorts and a polo shirt. “Hello boy” he said with a cheeky grin. “Hey” was all I could make out.
He told me to stand as he moved his strong hand over my body and I quivered. He grabbed my cock through my shorts and squeezed, he told me not to touch my cock until he told me to. I nodded and he pushed me down to my knees and he grabbed my face and pushed it into his crotch, rubbing it all over. He then reached into his shorts and pulled out his thick slab and tight balls, he had a shiny metal ring around the base of his cock that cupped his balls, I came to learn this was a cock ring. It was dark but I could see the veins popping and the bulbous mushroom head shiny with pre cum. I looked up at him, he had a devilish grin and he smacked his heavy cock against my cheek and then told me to open my mouth. He pushed his cock head into my wet mouth, the texture and taste was incredible. He pulled out and my lips made a pop sound as they let go.
He told me to open wide and take a deep breath, within seconds he had pushed half of his 7 inch thick cock into my mouth. My instant reflex was to gag and pull back but he held my head in place, he slowly pulled out and I took long deep breaths. He told me to breathe through my nose and open up again. I did as he asked, his pace slowly quickened as I got more accustomed to the size and speed. With every thrust he pushed further into my throat, my gag reflex was holding but every so often I would splutter with mouth juices coating his cock. He pulled out and his heavy cock dropped and then stood straight out. He slapped my cheek which I was not expecting and he said good boy. Wow I liked that.
He stood me up and began kissing me hard, I had kissed guys before but not like this. It was hot and heavy and he had a small moustache and stubble, he started squeezing my ass as his tongue was exploring my mouth which was wet and dripping. He took off my tank top then took his shirt off, revealing a hairy chest and a thick frame with a bit of a belly. He gave my ass a couple of smacks and squeezes then spun me around and pushed me to bend over the bench seat and lean over the table. He pulled the footy shorts down and took them right off and shoved them into my mouth and said to keep my voice down. Then he spread my legs as far wide as he could get them. My black underwear were straining with my cock hard as a rock and had a soaking front wet patch from precum. He gave a few more spanks as I moaned into my footy shorts. I don’t know how he accomplished it but I felt his finger poke through the cotton of my underwear under the waistband and then with both hands he tore a large hole and I felt the crisp air on my smooth hole, Three more smacks then a large spit ball landed on my hole. He got down on his knees and pushed his tongue onto my ass.
I’ve never had a rim job before and he was working his tongue like he did in my mouth. My footy shorts were soaked with the drool from my mouth and my moans felt like they were echoing through the park.
My hole was now wet and pulsing, Mark entered a finger into my hole which made me wince slightly. “Boy you are tight” he said. I spat out the shorts and told Mark that he was my first. I was scared to look at him thinking he was no longer going to be interested. I was dead wrong. With glee in his voice he said “boy you’re a virgin?” “Yes sir” I responded. He bent down to his shorts and pulled out a tube of lube and coated his cock and my hole with it. He continued fingering my virgin hole. I was moaning louder that Mark had to reach around and shove the shorts back into my mouth. He had two fingers in my hole and he was stroking his own cock, I think he was edging so much he couldn’t wait any longer.
He stood up and placed his cock on my hole . “Are you ready?” He asked, I nodded and with that he pushed the head of his cock against my hole. The pressure was intense and I felt my hole open and envelop his cock head, I let out the biggest moan yet and he quickly told me to “shhh” and followed with “good boy”. He held there while I regained my breathing and he pushed in further very slowly. I winced and told him to stop, but to my surprise he didn’t stop, “it’s alright boy, you’re doing good” he would continue to say as he got deeper into my ass. He stopped and said “you’ve got all of me inside you”. The pain was intense I exclaimed “I don’t think I can do this, it hurts!” He shoved the shorts back into my mouth and put his hands on my back pushing me down onto the table and he began to pull out but he would thrust back in and I moaned again. He continued for a few more strokes and then the pain eased and pleasure took over, he was hitting my prostate (I didn’t know what that was but it felt fucking incredible) and my moaning was getting louder as was his and his pace quickened.
I hadn’t even noticed my cock was still trapped in my underwear and I had been told not to touch it but I couldn’t control myself and I pulled my cock out of its precum soaked prison and stroked. I felt a whack across my arm and Mark said “don’t fucking touch it!” He reached around and gripped my cock and then put it back in its wet prison. He grabbed my arms and put them across my back. I almost wanted to cry. The dominance was such a surprise and I didn’t know how to take it but I began to like it. He was fucking me hard now, his balls were slapping my cheeks and then I felt him release. He let out a huge moan that I think he had forgotten for a second where he was and I felt a warmth inside of hot cum coating my guts. He pulled out and rubbed his cum covered cock all over my hole. My hole was gaping and dripping, he helped me stand up as my legs were wobbly and began kissing me and fingering my hole then put his two fingers in my mouth as I sucked then clean. He released my cock and pushed me down to my knees. He put his cock against my lips and instructed me to clean it up. I opened my mouth and tasted the juices and cum that covered his cock I began thrashing my cock as I swallowed his. He told me to breathe through my nose as he pushed deep down my throat as his cock ring hit my lips. I was gagging and spluttering but he held me there. My balls tightened and the biggest load of cum I’d ever seen exploded from my cock. He released my head and I slid off his cock and took long deep breaths as cum kept spilling out of my cock.
Our feeling of relief was short lived as a pair of headlights pulled into the car park next to Marks car…