Turns out I finally got someone from Craigslist to come over to my house. Two older guys, to be specific.
And yes, tonight was not only my first time sucking dick, but my first time doing ANYTHING sexual. Here's what happened...
The first guy (referred to as Tall Guy from here on) showed up around 7:20, a little earlier than he had said because the drive didn't take quite as long as expected. We talked about stuff for a little while to pass the time while we waited for the other guy (referred to as Married Guy from here on) to show up. At around 8:00, we figured he wasn't going to come after all, so we went ahead and went upstairs to the extra bedroom.
I was kinda nervous about the whole thing at first and didn't really know how to start... so Tall Guy took his clothes off and got on the bed. I was a bit surprised about how big his dick was... I didn't have any problems with it, but it was just huge compared to mine (and it was the only time I've seen another guy's dick up close before.) He wanted to suck mine first, and he started grabbing it through my boxers, so I took them off and let him play with it. After a little bit of that, I started getting partially hard, and he told me to lay down on the bed. I did, and he leaned over and started sucking my dick. I wasn't quite sure what to expect, but it felt really good; very warm and kinda slippery, with some suction. I had no idea what it was going to be like before it happened, but I never expected it would feel that good. I just kinda laid back and let him suck me for a while, then I heard a car coming and went to check if it was Married Guy finally showing up (it wasn't.)
I came back up to the bedroom and he asked me about rimming; I told him I knew what it was but I wasn't sure about it (and I really didn't want to put my mouth on someone's asshole.) He wanted to do it to me, so I got on the bed and laid down on my stomach, and then he got behind me and basically stuck his face in my ass and started licking and sucking at it and sticking his tongue inside. This felt pretty good also, though I think I liked getting my dick sucked better. After a minute or so of that, I heard another car coming, and this time it was Married Guy's car pulling up. After he came in and came upstairs, he got naked and sat down on the bed along with Tall Guy.
I got kinda nervous again, but eventually I took my pants back off and laid back down on the bed. Married Guy started sucking my dick, while Tall Guy sucked and licked one of my nipples. After a while Tall Guy moved down to my belly button (which was kinda weird) and then to my balls and dick. Married Guy went down and licked my balls for a little while while Tall Guy sucked my dick again. After a little bit of this, Married Guy got up and walked over behind me, dangling his dick over my face. It was longer than Tall Guy's but not as thick, and it wasn't circumcised. I kind of grabbed it and stroked it a little, then licked at it and put the head a little ways into my mouth at first. He grabbed it and wiped it all over my face and lips for a little bit, then I reached around behind him and pushed him down so his dick went further into my mouth. He stayed in that position for a while, sticking his dick into my mouth and then pulling it out, and I'm pretty sure I managed to take it down into my throat at least once... but that position was kinda uncomfortable for me, so we had to stop. Tall Guy stopped sucking me, and then started sucking Married Guy's dick instead.
This left me by myself for a few seconds, so I decided to start something for once and got on my hands and knees on the bed next to where Tall Guy was. His dick wasn't hard anymore, and I grabbed it and kind of felt around on it a little bit before popping it into my mouth. It didn't take long for him to get hard again after that--it happened so fast that I actually felt his dick growing inside my mouth. I kind of bobbed up and down on his dick for about a minute or so, taking it almost completely into my mouth a few times (and I didn't really have any trouble doing that, even though it was 7 inches long and pretty thick o_o). He put his hand on my head and ran his fingers through my hair while I sucked him, and before long he was asking me where I wanted the cum. He wasn't sucking Married Guy anymore at this point, just lying back on the bed and watching me. Married Guy was standing next to me and reached in between my legs, grabbing and stroking my dick. I shrugged and mumbled something (with Tall Guy's dick still in my mouth, only popping it out for a second to look at him), then went back to what I was doing before. Not much later (maybe 20 or 30 seconds), he started moaning a little, and immediately afterward he shot his load into my mouth. He let out two or three squirts in there (grunting and moaning every time) but it didn't feel like there was a lot of it there... it had to be less than half of what I usually make when I masturbate. It tasted kinda weird; salty but also there was some other taste to it that I couldn't quite point out. I gagged a little and pulled away from him, letting a drop or two of cum fall out of my mouth but swallowing most of it.
After this, I got up off my hands and knees and sat on the edge of the bed instead. Married Guy came around in front of me, and I started sucking his dick again. Even though it was longer than Tall Guy's, I really didn't have trouble getting it pretty far in my mouth (though if I took it all the way in I started to gag a little.) After I sucked him for a little while, he put his hands on my head and pushed me down lightly. I let him kind of guide my head for a little bit, then started going a little faster and taking him further in every time I went down after he let go. He put his hands back on my head, and I let him push me down and pull me back up, almost like he was kind of lightly fucking my mouth. It didn't take long after that before he shot his load in my mouth as well; there was definitely more this time than there was when I sucked off Tall Guy, and it wasn't as salty (it almost had a doughy kind of taste to it.) I think it was still less than what I usually make, though. I gagged a little on the cum again, and pulled away. A little bit of cum dribbled out from my mouth and down onto my chin, and some more kind of made a "trail" from my mouth to the tip of his dick as I moved away, falling onto the bed after a moment of hanging in the air between us.
After this, Married Guy had to leave. Me, him, and Tall Guy talked a little bit, and both of them pretty much agreed that I give really good head, especially since this was my first time. Married Guy even said it was proof that guys give better head than girls, and said that I could take his cock deeper into my mouth than most of the guys he's gotten sucked off by before. He put his clothes back on and I showed him to the door; after that I came back upstairs, where Tall Guy was still there. We talked a little, and I told him I wanted him to finish sucking me off. I laid back down on the bed and watched as he got on his knees beside the bed and started sucking me again. It still felt really, really good. Maybe even better than the first time. He kept this up for quite a while, at least 5 minutes or so (probably more.) But for some reason, no matter what he tried or how much he sucked it, I just didn't cum. I even tried closing my eyes and imagining girls I liked doing it... still didn't work. Apparently that happens a lot the first time, and he said it was probably just because I was still a little too nervous about the whole thing. He got his clothes back on and left, asking if I still had his e-mail address (I do)... apparently he might want to make this a regular "sucking buddy" type of thing. It'd be a lot easier than trying to get guys from Craigslist to come over every time, that's for sure...
Unfortunately, I wasn't able to get pictures of any of this... never really got a chance to ask if it was okay or not, and by the time everything got started I didn't really think much about it! Heh.