This happened to me back in my junior or senior year of high school around my 18th birthday. Although I had sucked dick before it been several years and I had never swallowed before. This is a completely true story and thinking about it still gets me hard. I might even have to stop and jerk it before I finish the story!
A few years ago when I was in high school I posted an ad on Craigslist looking to give a blow job. So I ditched school and began exchanging emails with a guy named Steve (I think, I don't really remember lol). So we agreed to meet on the corner of my street and drive somewhere more private where I could do the deed. We decided on a parking lot for a little league baseball diamond since it was November no one would be there and we were right. The only people were construction workers on the edge of the lot. So we park in the middle of the lot and get into the back seat of his suv (he had a big center console so I couldn't do it up front) and he undoes his belt and pants and pulls them down to his feet. So now I'm sitting here with an older guy in his 40s or 50s with his cock out and I couldn't stop myself from taking his whole soft dick into my mouth and enjoyed how it stretched as I moved from its base to the tip. I loved the feeling of his cock getting hard in my mouth although he wasn't very big so I managed to fit the whole thing in my mouth. I loved how his dick tasted so I moved down to balls and licked the whole sack before sucking each one into my mouth.
While his cock wasn't impressive his balls were magnificent and I could only fit one in my mouth at a time. After giving his balls a good going over I worked my way back to his dick. I licked up and down the shaft and swirled my tongue around head before taking into my mouth again. I bobbed my mouth on his cock for a few more minutes and I felt this hot wet sensation on my tongue and figured it was pre-cum. Then it happened. Those big balls filled my mouth with his hot thick load. I never took my mouth off of him and swallowed the first mouthful and he filled my mouth 2 more times. I swallowed it all down and only missed a single drop of his very tastey cum. I was in frenzy at this point and keept sucking him after he came til he literally begged me to stop. Then he did the hottest thing ever! He pulled his pants up got in the front seat and started the car and invited back to the front seat. I got out closed the door and he took off! He pulled around thanked me for my good work and sped off never to be seen or heard from again. I felt like a whore but I liked it. I quickly went home a masterbated like 3 times in a row because every time I thought about swallowing his cum I got a raging boner. Every time I came I ate it hoping it would be like his. But sadly his was much tastier.
I haven't had any more luck hooking since then sadly. I almost had one about a month ago but we had to call it off. Well since this isn't 5000 characters I guess this will be a two-fer.
This story is of my first experiences with another guy.
When I was fourteen I was like your typical teen, horny! I was always jacking off when I was alone or hell even with other people in the room. Unfortunately I wasn't attractive and was lacking in the dick department. So I got no pussy at all. My neighbor was similar too me in that he was always jacking off too even in front of me. He was a year younger but at least two inches longer than my meager three incher. One day while very horny I had a brilliant plan. I'd offer to suck his dick, which I secretly wanted to do for ages, and in exchange I'd get to fuck his ass. So he comes over to my house and I wait till were alone to set my plan in motion.
Just as I planned as soon as were alone he pulled his dick out and began stroking. I knew once he was stroking he would be to turned on to refuse. I got closer to him and grabbed his cock and started stroking it. He looked at me in shock but I kept my eyes on his dick. Without looking up I told him my proposal. He shook his head yes and I said good man and got on my knees in front of him. I looked him directly in the eye as I nervously placed his cock head in my mouth. I savored the taste of his big dick as I slowly slid more of it in my mouth. I managed to fit most of it my mouth but choked on near the base. He let out a moan and closed his eyes as my mouth worked his cock. He put his hand on the back of my head and forced his cock further in and gaged me several times before I pulled his spit covered dick out of my mouth to suck his balls. Luckily I could fit both of them in my mouth and greedily sucked them in and rolled them around with my tongue. I returned to sucking his member and started moaning louder and louder and started working his hips to fuck my mouth. Being younger than me he couldn't cum yet and had a dry orgasm in my mouth.
By this point I was rock hard and super horny. I bent him over the couch and dropped his pants. I played with and smacked his ass cheeks which were actually quite nice. I spit onto the tip of my dick for lube, I'd seen this in a porn online, and I pressed my dick into his hole. It was wonderful! Tight, warm, moist I couldn't help myself and started humping away. I thought he was enjoying it too and as I was ready to blow he asked if it was in. My mouth fell open as I squirted my small load in his ass crack. He says "oh I guess it was" and offers to do it again when ever I wanted. Even though that was a huge blow to my ego I took him up on his offer and did this several more times over that summer.