Craig's List Finally Cums Through! - Part One

Happy Sunday, everyone. It was a pretty big weekend, so let me get on into it. This is part one of two parts, concerning the lead-up to Friday night. I'll try to get part two up later tonight, detailing Saturday (and filling in the rest of the weekend, which will serve as my weekend update.)

Last Wednesday I was doing my usual morning pre-work routine; getting the computer up, checking email, using my phone to look at Reddit and other naughty things, etc. I decided to check Craig's List just in the off chance that there might be something work responding to. As it happens, there was.

First of all, the picture of his dick that he put in his ad caught my attention. (Posted with his permission; he knows I have a blog but I haven't told him where it is.)

Now I'm not turned on by dicks like I am by pussy and tits, as I've explained before, and it's not that this one got me all hot and bothered, but come on! How can you not want to read the ad that's associated with that?! And the ad hit all the right notes for me, so I responded with a little bit about me (married, curious, might be interested, etc.) and included one of my many dick pictures.

Now at first I was a little put off by his responses; they were curt and abrupt, and he quickly wanted a face picture. It's not that I minded sending one, I just was looking for a little more discussion I guess. I almost dropped it there, and even wrote an email to James asking him his advice on it (and of course he came through as usual.) The long and short of that was after the guy and I exchanged face pictures, the conversation picked up and I started feeling more at ease.

Thursday we continued talking, now via text, and decided to get together Friday night for a meet and greet at a local establishment. He agreed that it would be meet and greet only for this first time, though he said many times how horny he was and couldn't wait until we were naked together. I got the feeling that he was trying to turn me on with compliments and sexy talk (like how I hope to turn on a woman I want to get with) but it really just made me feel a little uncomfortable. I just want to suck your cock, dude, not be seduced!

But in all other respects, he seemed like the kind of guy that I can be friends with; intelligent, good sense of humor (or at least could laugh at my jokes), well spoken. By Friday, as we continued the conversation, I knew that unless he really screwed up the meeting that night, this would probably be a comfortable situation. (And I think he picked up on my discomfort because, without me saying anything about it, he did back off from that.)

My big concern came after I sent the above picture to Simplicity and she mentioned how thick he looked. I really didn't think he was all that thick from the picture, but I must have gotten the perspective wrong. I asked him how thick he was at the widest and he said "Like, 6.5 inches." Oh, fuck. Well, one step at a time, right?

We met out in the parking lot of the establishment about 6:30 (the wife was at a game, of course) and went inside. The trick is finding a place that's not so loud that you can't have a comfortable conversation, but not so quiet that your conversation carries to everyone. We got a table a little ways away from the other groups, and the volume level seemed about right. Still, I just had the paranoid feeling that everyone looking at us knew exactly what we were up to!

Craig (we'll call him that because I met him on Craig's List) had already told me he's been with women before but is definitely gay. Honestly I was a little worried that he'd be effeminate (even though he's a bigger guy), kind of like Cam on Modern Family. Fortunately he wasn't, and I don't think most people would really know he's gay unless he told them (or, you know, grabbed some guys junk and kissed him.)

(No, he didn't do that to me.)

(Until later.)

Anyway, we ordered a pitcher and some nachos and started talking. Well, mostly I talked for the next two hours and he listened. I just meant to give a little more background on me, but one thing led to another and I wound up telling him all about the L, B and S drama over the past three years. I didn't tell him about L's and my shenanigans (though I came close a couple of times) but he was enthralled by the story. Near the end of it he asked who L was with now, and I told him she's with B and will definitely not be going back to S. He asked how I could possibly know that and his jaw dropped when I told him that S had killed himself last October. After a bit of stunned silence he said "You know how to tell a hell of a story!"

I also told him about my past experiences with Brent from last year and T a few weeks ago (it turns out he knows T!) and really tried to emphasize how each time I froze up when it came to the time to do anything. By then he'd paid up our bill and we'd moved outside to the parking lot, and it was getting close to my cut off time to be comfortably on the way home before the wife left the game. I had a cover story for being out (meeting some guys from work) but didn't want to be coming in later than her. I told Craig that I felt comfortable and I thought that, if he agreed (he did), that we could get together Saturday or Sunday while the wife was at another game.

He asked if I wanted to follow him home (assuring me he understood that nothing would happen) just so I'd know how to get there. I'd been thinking along the same lines, and because he said he was only about five minutes away, I figured I'd have time to get there and still get home within my margin of error. As we went through the twists and turns to get to his place (he's renting the downstairs apartment of a friend of his house in a really nice neighborhood) the beer I drank started calling for attention, so when we got there I asked if I could use his bathroom.

As I took care of business I read an email from Simplicity asking how things had gone. I quickly responded that nothing was going to tonight but that we were going to meet up probably the next day. I finished up, washed my hands and went back into his room. I'd thought about asking to see his dick, or asking if he'd want to see mine, but once again I was frozen and just couldn't make that move. (I've really got to work on that.) So I stood awkwardly, hemming and hawing while we made small talk, and finally said "well, I guess I should probably be going." He laughed and said okay, and that he'd walk with me to my car.

As we stepped outside the basement entrance, which is kind of hidden from the rest of the neighborhood (it was at the end of a cul-de-sac), he said "Stop a minute." I did and turned towards him and he stepped closer, and I thought he was going to try to kiss me. He'd asked in our text exchanges about kissing, and I said it wasn't something that turned me on (with guys, anyway) but it didn't gross me out either and if he wanted to that would be fine. He didn't kiss me (I don't know if I was more relieved or disappointed), but he stood close and reach down to fondle me through my pants. I knew I wasn't presenting much at that time (I'd told him I'm a grower, not a show-er) but I could feel myself starting to respond. I reached over and fondled him as well, and though he didn't have a hard-on either I could tell he was getting there.

I mentioned that I had thought to ask if he wanted to see my dick and he immediately pulled me back into the house and to his room. I started to freeze up again when he asked if I wanted to see him, and I said yes, so he unzipped and pulled his shorts and underwear down. That broke the ice so I unzipped and pulled myself out as well. We stood closer and stroked each other for a few seconds before I said "Ah, hell, I better try it out a little while we're here, right?" He sat down on his bed and lay back while I kneeled there and licked his shaft and then took it into my mouth.

Again, he wasn't fully erect at this time so it didn't seem to difficult to get around that swell in the middle. He moaned and groaned while I sucked him, and he was starting to grow a bit more. I wanted to continue, but it really was getting late so I stopped and told him that would have to do for now. I stood up in front of him as he sat up on the bed, and he grabbed me and pulled me towards him. He said something about wanting a taste too, and took me into his mouth. It felt good and I was starting to respond, but the clock was ticking in the back of my head. After about a minute he stopped and I zipped back up.

We walked out to my car (he had me stop again to fondle me some more) and talked a few more minutes, solidifying the plans for the next day. I did warn him that it entirely depended on the weather, and whether or not the wife went to the game. She almost certainly would if they were playing, but it has happened on the rare occasion before that she would decide at the last minute to stay home and spend time with me.