Before there was Grindr, meeting a guy for sex was not so accessible. Especially for an 18 year old boy like myself. Before getting into the encounter, let's take you back to how I started with anal play.
When I was a young man, I would get so horny it was hard to control myself. I would jerk off (alot) almost every chance I got. I would ditch class and find alley ways, abandon houses, orchards and pretty much anywhere I could free my cock and finger my ass because, honestly I felt it was the only way to make myself cum. I would always hope for someone to come along and catch me in the act while I was on all fours, completely exposed and fingering my hole. At this time, I started to use a carrot and worked my ass up to a cucumber a few times. My favorite spot I to play was a clearing in an orchard near my house. I liked this spot because there were apartments that overlooked the area and there was just enough light during the evening so others could see exactly what I was doing. So, one night I brought along a homemade dildo that I created. It was clay molded around a brush handle about 3 inches thick and 4 inches long. I would just put a condom on It and pound away. I took my clothes off and was completely naked. Slowly playing with my dick until it got nice and hard. I got down on all fours and began sliding "my little assistant" into my tight little hole, when I heard deep voice... "Hey, please don't get scared, I'm just admiring what I see" but, believe me, I was terrified!
I turned to see an older man (late 40s) with his pants around his ankles working his long thick cock. I guess because I was well into my enjoyment I didnt hear anyone approach. The light shined on the clearing so I knew for sure, that I was fully exposed. My clothes were on a tree nearby so I couldn't just pull up my pants or cover myself... I thought to turn and run away, but something just felt like I should see where this goes. I said in a soft voice "do you like boys" he said, "FUCK YEAH" and I knew this was going to get wild.
I had never been with a guy before this and had never even seen a dick in person (other than my own) he was fully erect and from what I could tell his dick was much bigger and thicker than my own and much bigger than the toy I made. The length and width of his shaft really turned me on. I felt my erection grow stronger just from the sight. I was scared but I knew deep down this is what I wanted. In a very apprehensive voice he asked if I had ever touched a cock before. I hesitated to reply but again, for some reason I felt like I needed to just grab hold and see what it felt like.
I walked closer and before I even knew it I found myself stroking and rubbing his cock, it was smooth and thick and my fingers could barely wrap around it. My heart was about to fly out of my chest from the fear and he seemed to feel my nervousness because he pulled me closer and just hugged me gently as I was working his hard pole in between my fingers. I felt a sense of ease as he slowly massaged my back. At this moment I dropped to me knees and slowly started to lick his penis and nibbling gently on the head and shaft. When I finally put my mouth around it I could taste the saltiness of his skin. I started to suck harder in hopes I would finally taste cum (I had been curious about this for some time) I could hear him start to moan and I definitely thought this was it, and I was going to get a mouth full! Instead of getting my mouth filled with cum he suddenly pulled back. I thought I was doing it wrong, but he said "that's good, for now" he gently grabbed me by the shoulders and stood me up. He pulled me close again and began to softly kiss me and lick my neck. My cock was as hard as it could be and I was just hoping he would return the favor I just performed on him, but instead he whispered "you ever had a dick inside you" and before my brain could even catch up to the feelings going through my body... I whimpered "no, daddy" I used the word "daddy" because I heard it in porn and in sex stories. I did feel like I was one of those whores in a porno trying to please their "Daddy" at this point. Now for some reason I felt the whole world around me go dark and the only thing that mattered was just me and this random man in front of me. I felt his hands slide down the small of my back as he began caressing my butt, holding my firm cheeks in his hand and squeezing my soft curves. His hands inching closer and closer to my virgin hole. Just then, I felt it! His finger, it pressed firmly against my puckered little hole. My whole body shuttered as his finger, softly swirling around by ass. My body began to quake and I started feeling my back arch as if it knew what was going to happen next. As my body started to assume the position, this stranger must have been waiting for it because he turned my body around and there I was... bent over, back arched, and my ass high in the air. I felt like I had been waiting for this moment my whole life. I didn't know if I should turn to greet him with a smile or pull my ass apart but all I knew was that I was fully exposed and eagerly anticipating whatever was next in this adventure. Just then I felt something warm and very soft, unlike anything I had ever felt before. I had finally got the nerve to look between my legs and at this point I realized he was licking my ass and with every breath I took, I felt his tongue push further inside me. His saliva run down my balls and legs as he kept getting wetter and wetter. I felt something push inside me. I couldn't help but moan, i already knew the feeling of something inside of me but not like this.... I felt his huge cock press against my ass as he brushed his dick up and down against my wet hole, I started to moan a little louder I felt his cock push into my tight wet hole and I felt like I was going to pass out from the pain. I never felt anything like it. It felt as if someone exploded a cannon full of glitter inside my ass. He must have felt my body try and reject what was being inserted inside me because He wispered "relax, that was only the tip, do you want me to stop?" I really did want him to stop, but again my body spoke before my brain and I muttered "fuck me daddy" as I reached back with both hands and spread my ass wider I could feel him spit and rub his warm saliva around as he continued to push slowly inside of me. All I could do was just brace myself for what was to come. I felt his cock enter my hole and I push back against him. The man struggled with every push forward but continued to slide further and deeper. I felt the tightness of butthole being opened more and more, as his cock drilled deeper and deeper inside of me. We both began to let out noises that felt like uncontrollable gasps and grunts as our bodies were getting closer and closer. With each and every forceful push, i felt my ass opening wider and wider. When my hole seemed to gobble up every inch of his thick monster and I felt his body press against my ass, all i could do was whimpered like a baby. He was no fully penetrated! My asshole was engulfed by a huge cock and he began to pump in and out of my ass. The pain I felt seemed to fade and the pleaser took over as he thrust his rock hard cock, harder and much more aggressively with every motion. I couldn't hold back the moaning or the uncontrollable tears that streamed down my face as his dick slid in and out of my body. The tears were from the overwhelming pleasure that I was feeling. I dont know how long he was pounding in and out of me, but it felt like we had been at it for a while and then he finally spoke, but just a faint whisper "do you like it?" but all I could do is answer "yes daddy" and "fuck me harder" as I gasped for air and let out moans that could surely be heard by more than just me and this bull having his way with me. Just then he said "you wanna feel my cum inside you" and I really did, but instead I just shouted "cum on my face" that must have been exactly what he wated to hear because he then released his enormous cock from my ass (and that was another feeling ill never forget) I felt his cock long hard cock slide slowly out of me and my body shivered as it popped out of my tight ass. He quickly moved around to my face and I dropped to my knees. I thought I was about to be sprayed by his enormous fire hose, but instead he grabbed the back of my head and pulled me on to his dick and said "Suck it" "bitch" or "slut" but I was so enamored with the many feelings I had at that point I really can't remember. I could feel my own dick getting harder he shoved his dick into my mouth. His thick shaft went right into the back of my throat as I tried to opening as wide as could trying take in every of his cock. I gagged and gulped as he began to fuck my mouth. I could feel my throat being opened up with every thrust and his balls bouncing on my chin. I could barely breath, but I needed to taste him! The eagerness and anticipation at this moment was consuming me. I knew that I would finally be able to taste him. I would feel his dick drain into my mouth. I needed it! I felt his body start to twitch and he stood up on his tiptoes as he began to release his soul into my mouth. I latched my lips around him and sucked and gobbled up every single drop as I worked my own dick furiously trying to cum along with him. The salty bitter taste of his cum sent my brain into a frenzy as I myself exploded in thick streams of cream. I came harder and more than I ever had before, i felt like it wouldn't stop. Finally, after we both caught our breath and I released his cock from my grasp. He just pulled up his pants said "Thanks, bud" and left into the darkness. I never saw him again and still wondered if he had been watching me from those apartments or just happened to stumble on to a horny young man getting off.
