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Hey all! It’s been awhile since my last story. Life, you know? Anyway, I thought I’d share another great story of mine. As usual, names have been changed but these are all true stories of my adventures.
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It started a few months after getting robbed by my neighbor. I’d been trying online dating for awhile, but nothing really took off. There were a lot of flakes, and a lot of guys who just didn’t catch my eye very well. One day, not long after I’d discovered craigslist, I decided to post a personal ad. I got a few responses, but none that really seemed to work out. We’d exchange emails and chat, and I had dates with a couple of them, but as usual, nothing seemed to work out. Then I got an email that definitely had my attention. His name was Daniel, and he’d just turned 18. I was 23 at the time, but disinterested think the age difference was that big. His email made him seem nice enough, and we seemed to have a few things in common. So, after a few days of emails, I suggested we meet up for coffee and talking.
There was this coffee shop in town that was not like your typical Starbucks. They were a multistory building that had space in the basement for bands and art exhibits. I felt like this was good neutral ground to meet at. I was incredibly nervous, as I hadn’t been on a first date in a long time at that point. I got there extra early, mainly because of nerves, but also because I didn’t want to end up being late. But I guess Daniel must’ve had the same idea, because he arrived not long after I did. We met and exchanged a hug at his insistence, and it felt really nice. I remember taking a quick sniff of him. He smelled like he’d just showered, all pine scented but not in an antiseptic way. He was about 5’8”, slim, smooth shaven, with short, dark blonde hair, a graphic t-shirt and skinny jeans. His smile nearly took my breath away.
We ended up chatting in that coffee shop for a couple of hours, and we only parted ways that day because he had a gig in the next town that night. He was a singer and hoping to move out to Los Angeles in the next couple of years to try and break into the music industry. I did ask him to sing me something, but he demurred and instead invited me to check out one of his shows. He was scheduled to do a show the next week at an outdoor shopping center not too far from where we’d met. I told him I’d love to see his act. We exchanged numbers and said our goodbyes. It took every ounce of willpower I had not to kiss him right then and there.
The next week, I was at the shopping center early and ended up walking around the bookstore for about an hour before Daniel’s scheduled set time. As the time approached, I went out to the main courtyard and found a good seat. I saw him setting up with some of his friends, but didn’t go over. I was way too nervous. What if he sucked? What if he wasn’t a good live performer?? He was cute and we got along great when we’d call or text each other, so please God don’t let him suck!
I had nothing to worry about, as I soon discovered that he was an excellent singer and piano player. He played a few covers like Hallelujah, but he also performed a few of his own songs. His voice was amazing, so light and airy, like an angel. I was ecstatic. He was cute and talented?? Not fair!!! After he finished, I went over and congratulated him on a heat performance. We couldn’t chat for very long as he had to pack up, but we set up a date for the following week.
Over the next couple of months, we had quite a few dates, usually meeting up at a new spot downtown, or after one of his shows. I even dragged my roommate Calvin along to one of Daniel’s shows, partly because I had to make sure that I wasn’t just imagining this guy. Calvin approved, of course, because how could he not?
Up until then, we hadn’t really been intimate. Sure, we’d had epic make out sessions, or cuddling at the movies, but we hadn’t done much more than that. Before Daniel, I’d hooked up with a few guys, and any dates I’d gone on that ended in sex, usually ended up fizzling out right away, so I wanted to take things slow with Daniel. He wasn’t a virgin either, as we’d talked about our first times during the course of our relationship. Still, we were a couple of months in, and I was getting anxious.
So, like any guy with ulterior motives, I scheduled a date night at my place. I convinced Calvin to give us the house for the night by letting him borrow my car. I cooked dinner. Nothing fancy, just a simple pasta dish and some wine. Daniel came over at 8pm sharp, just as he’d said he would. We ate dinner at the dining room table, then went over to the living room to watch a movie. We mostly turned it out as we got into an epic session of cuddling and then making out. Eventually, I asked Daniel I’d he’d like to see my room.
I led him up the stairs, up to my sparely decorated room. Really there was just the bed, a dresser, my desk, a bookcase, and the TV. Nothing fancy, really. As we entered, I led Daniel over to the bed and we both sat down. We resumed our make out session, with me now slowly but surely working my hands up his shirt. This seemed to do the trick, and I felt him lean in to my caresses. Eventually I managed to get his shirt off, and started kissing my way down from his lips. First sucking at his neck, then down to his nipples. I sucked each of them in turns which made him moan in almost a whisper. He was returning my touch, and eventually he had my shirt off as well. I kept making my way down his chest and torso, slowly lowering him back onto the bed. I went back up to kiss him again, putting my hand lightly on his crotch. I could feel him under his jeans, hard as a rock. I asked him if that was okay, and he gave a breathless reply that it was.
As I continued kissing him, I slowly undid his belt, and started taking his jeans off of him. Daniel moves his hands from my chest and helped me to get his jeans and boxer briefs off. I broke away just in time to see his cock release from his underwear. He was about 7” long. Not too girthy, but it was as perfect a clock as I’d seen in a long time. I grabbed him, squeezing gently. He bucked his hips up in time to my strokes. Precum started to ooze out of his dick. I moved my head down to meet him, and started licking around the head. He tasted sweet, and soon I had his cock in my mouth. I started going up and down slowly, gradually picking up speed.
As I worked his dick with my Kitt, my hands were playing with his bells, and eventually my fingers found their way to his ass. I teased his hole gently, slowly swirling around the outside of his tight pink pucker. I pulled off of him for just a moment so that I could suck my finger. Then I slowly reached back down, teasing some more, before slowly entering him and my mouth went back to work. He moaned in ecstasy, and I saw him grab onto the blankets tightly. He was loving every minute, and so was I. I managed to get another finger in, and was now fingering him in time to my sucking.
After a few minutes, Daniel’s breath started to quicken and he was bucking his hips harder and harder so that my fingers went deeper and deeper into his ass and his cock went deeper into my mouth. After another couple of minutes of this, he shouted that he was going to cum. I quickened my pace on his cock and ass, and finally got my reward. He shot straight down my throat, and it felt like he was cumming buckets. His orgasm didn’t stop for a long time, and I had a hard time trying to swallow it all down.
As he came down from his orgasm, I slowly came off and out of him. It took another few minutes for his breathing to return to normal, and we just laid there side by side for awhile. We kissed a little bit more, but not as deeply as before. I think he may have been a little out of by me having recently had his load in my mouth.
By this time, it was late and he had to go. We made our way back downstairs and I walked him to his car. I told him I’d enjoyed the night, and he said he had too. We scheduled another date for a week later, and he drove off.
Sadly, I didn’t seem him again. The night we were supposed to have our next date night, he called me about a half hour late and said there’d been an emergency and we’d have to reschedule. He didn’t call that time, though, and I never heard from him again. I minorly stalked him for a while after that. A couple of years later, I discovered his album on iTunes and bought it, and I found out that he had ended up moving to LA. I moved to LA a few years after that (NOT to stalk him, seriously), and considered looking him up just to see how he was doing, but I managed to come to my senses and eventually stopped looking him up. It was fun while it lasted, but I guess it just wasn’t meant to be. Oh, well.
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