First time... Attempt

[jjourneyman]

Yep. @KDaddy23 is a great voice of reason and advice. For my own 2 cents, dont stress it. My first time just jerking off another guy was a mess, actually a literal mess on the guys suit. My first attempt at intercourse, no matter what we tried, we couldnt get that thing in me. It was only later I learned the tricks of how to get a cock in you. The poor guys boner was looking like it was in pain

He was cool about it and got himself off. A song I love has one of the best lines in it "Sometimes the rainbow is better than the pot of gold"
Yeah, the fantasy can be better than the actual thing, as, once you do it, you cant go back, Just relax, dont pur presure on yourself, and eventually another opportunity may come around. Hopefully with a decent guy who you can be honest with, and they will realize the long term benefits outweigh the short term work

You nailed it on that one Jazmine!

[jjourneyman]

It's probably not that your expectations are sky high but you seem to be going through something a lot of guys do. You're eager to do this but when it's go-time, you find "reasons" not to do what you want to do. Then there's an air of doubt; the moment you start thinking that you're gonna be let down or that you're gonna regret it, it makes it even harder to do. I always say that these things sound like a good idea on paper but to put it into practice isn't as easy as it sounded in your head.

Not all first times get off the ground and run smoothly. Methinks there are two questions you need to ask yourself: Is this something you really want to do and do you believe that you can do it? It's not a matter of suppression as it seems to me to be a matter of finding reasons not to pull the trigger. In the encounter you were gracious to share with us, you got to thinking about some stuff that you probably realize now you shouldn't have been thinking about. You probably realize now that you could have asked him to switch places with you because you're right-handed but you also got to thinking about how thick his cock was and whether or not it would fit in your mouth; you probably realize now that you could have gotten some of him in your mouth and how you could have done it comfortably.

For some, the thought of getting some dick is highly exciting and good stuff to masturbate to but to actually do it? Ugh. Ya don't feel like yourself or that "voice" in your head is telling it's something you're not supposed to do. A lot of guys feel this way the first time so that's pretty normal - and why there are two questions you have to ask yourself and answer without bullshitting yourself. Sometimes we overthink that first time and it seems to me that's what you did. It's not as easy to tell you to stop thinking but, yeah, you get to a point in this where you kinda stop thinking, say, "Fuck it!" to yourself and just go for it. I wouldn't think so much about "specializing" right out of the gate, like being a sub bottom or sub cock sucker; I'd take the baby steps to be able to get my hands on a guy's cock - and practice doing it left-handed when you masturbate - and work up to being able to get the cock in your mouth then consider your thoughts about specializing as a sub of some kind.

I totally agree with you KDaddy! My first time, I was young and didn't really think much about it before hand. I think a lot of guys fantasize about it, but when another man's penis is actually starring you in the face, it can be a little daunting. The other thing is that online hook-ups that stretch out for long periods tend to make people over-think the experience. I once exchanged e-mails and messages with this one guy for three months. Finally, he agreed to meet in person at my apartment. The plan was for him to experience sucking cock for the first time and I did my best to assure him he would enjoy it. The afternoon he was supposed to show up, he text me to say that his wife had come home early and that he wouldn't be able to make it. I knew it was a lie, but I was cool about it, mainly because I understood what he was going through. We re-scheduled for the following week. On that day, he did make it as far as my front door (I know because I watched him park and walk to my stairs and I could hear his footsteps on my landing). About 10 minutes after he left, he text me again to say that he was stuck in traffic and that we would have to re-schedule. I figured, okay, twice stood-up but I thought I'd give him one more shot. On the third try, he finally went through with it. I met him downstairs and we walked up the steps together. Once we got inside, I tried to make him feel comfortable. I had put some porn on TV and offered him a drink (a little liquid courage can go a long way).

After about 15 minutes of small talk and a couple of shots of vodka, I felt he was ready. I sat on the couch and removed my sweats revealing my hard-on. That was all it took. Within seconds he was on his knees in front of me, his face just inches from my throbbing cock. I gently placed my hand on the back of his head and guided him down. For a virgin cocksucker, he did a great job. I even warned him that I was getting close and he just kept sucking, so I gave him his first load, and like a champ, he managed to swallow most of it.

Afterward, I asked him if he'd enjoyed it? "Hell, yeah," he said. "That was hot! I'm sorry I waited so long try it!" I could tell he was on a mental high as he wiped his face and took one more shot for the road. A few minutes after leaving, he text "Thanks! I'd like to do this again sometime." We got together several times after that.