How to help a shy/inexperienced guy feel comfortable?

I've know this guy who is, for lack of a better word, passive, shy, non go-getter, etc. I don't know him extremely well as we usually keep our conversations pretty light and humorous. We've talked for over a year on and off. He is not very social with...

those he doesn't know that well... but the few times we have hung out alone he is talkative and funny. I am the one to usually initiate conversation through texts and what not, sometimes it strike conversation, other times my efforts are wasted. He admits that he has never been able to make things happen when it comes to girls but he sometimes is flirty and semi-perverted (jokingly bringing up my ta-ta's and such) but not as much when we're face to face. He even sent me this random text once where he said he was pretty drunk and wished he had someone to cuddle with. My gut tells me that if he wasn't attracted to me he wouldn't say some of the things he says. Well, a couple weekends ago I was camping with friends and invited him to come out, I was the only person he knew out there but he surprisingly came and brought a friend. I was pretty drunk and initiated kissing and messing around and he got pretty into it once I started. We all had to pack up in the morning to leave so I didn't get to talk to him much that next day. I did get a text message from him a day later though and I was relieved because I was a little worried that maybe we did too much. Trouble is, now everything went back to the way it was before the messing around. I would have thought that maybe that would have broken the ice. Now I'm wondering if it was a mistake and I'm second guessing myself. Is there something I could be doing to make him more comfortable and put himself out there?

we have been talking in spurts on and off for over 3 years. Well, in the last couple months, we've hung out a hand full of times and text (sometimes semi-pervertedly) but it seems like I have to initiate a lot of all the communication because he admits that he isn't one to make things happen. So I invited him to go camping over this past weekend with me and some of my friends. He surprisingly came and brought a friends but they both seem to be a little anti-social, not in a rude way, just like maybe they don't really know how to mingle, which is fine. Well, I got pretty trashed and we all decided to call it a night... once we laid down, I playfully initiated messing around and then he got into it... pretty much everything but sex happened and then we passed out. He knows I don't mess around etc... I have purposely been sex free for almost three years and he is the first person I have wanted to go farther with. He and his friend had to leave the next morning so I didn't really talk to him much, just enough to really say thanks for coming out and bye. he sent me a funny text the next day which to me meant that everything was cool... but when I text him today it seems like nothing ever happened, the conversation went back to normal and he still seems timid. I kinda hoped saturday night would have broken the ice. I guess I'm kind of at a loss of what I should do, if anything, from this point to still encourage progress... the boy seems to need someone to lead him. I just can't figure out how to do it without giving off the impression that I'm trying to be his girlfriend right off the bat now, cause I'm not, I just want to enjoy the ride and see how things go. WHAT IS GOING THROUGH HIS HEAD NOW? Is it possible I scared him off by making this whole thing a little more real? Texts, emails and phone calls are one thing... this took it to a new level I would think.

Sorry, I forgot to earse the first part, the second part has a little more detail. lol, my fault.

hey, I just came across this post, I realize that you may not be reading this since you posted your question about 6months ago but ill answer anyway. I can almost assure you that since he answered your physical initiative that he does like you both sexually and mentally, thus the only reason why he has hard time expressing himself is because he's probably inexperienced around the opposite sex, and thus needs your comfort in the sense that you're ok w/ him being inexperienced; once that's settled between the two of you, everything will progress rapidly as long as you show him the ropes...all the best to you, good luck

hey, I just came across this post, I realize that you might not read this since you posted your question about 6months ago but ill answer anyway. I can almost assure you that since he answered your physical initiative that he does like you both sexually and mentally, thus the only reason why he has hard time expressing himself is because he's probably inexperienced around the opposite sex, and thus needs your comfort in the sense that you're ok w/ him being inexperienced; once that's settled between the two of you, everything will progress rapidly as long as you show him the ropes...all the best to you, good luck