First time
 

In the last year or so, I have started to seriously entertain the notion of having sex with men. I am primarily interested in anonymous, safe encounters with older men. Recently through craigslist, I found a man named John who is 52 (I'm 25), D&D free, single, and apparently very well versed in the gay casual sex scene. I've since contacted him via email and phone, and he seems sane. This would be my first gay encounter, and, as you might imagine, I am having some doubts.

John is adamant about making out, while I'm not sure that I'd be able to do it. The thought does not revolt me but does not especially appeal to me either. Am I making too much out of this?

As to my interests, I would like to be fucked aggressively while I lay on my stomach. John is 7" and thick. How feasible would it be for my virgin butthole to take him?

I want to do this but guess I am looking for a bit of reassurance. What, in your opinion, would be the most awkward part of this encounter?

I was the same
 

As you can read by my previous post in " am I gay ?" I had a tough time having sex with a man for the first time but I was so horny that it was easier than I thought.

If you don't want to kiss just let him know ahead of time. I was VERY uncomfortable kissing and it took me a very long time to do it. Most of my encounters were very understanding.

If you have not had anal sex ( I have not ) I would suggest that you tell him that you are interested but afraid. Try it out with a finger then a small dildo until you are comfortable. If you tell him he should have no problem.

Hell, I wish you and I could hook up so that i could mentor teach you.

My wife introduced a dildo into our sex life and now I sort of enjoy it although I need to make sure I don't enjoy it too much.

Never been fucked, I usually do the fucking. Just let " John " know how you feel and relax. He will probably enjoy teaching you as much as you'll enjoy learning.

Re: First time
 

Welcome to CFS.

Make sure you meet up with John in a public place first. There is a great deal of virtue in verifying that all or at least, most of what is usually claimed on Craigs and the web, in general, also holds some water in real life.

There are guys, who are actually 75 and trying to pass as 52 year olds. (Nothing wrong with being 75. You just may want to know first.)

Be prepared that 7-web based inches are actually 4 - 5 inchers in real life. Nothing against that either, but you just may want to know first.

There are guys, who seem to be perfectly OK, when it comes to exchanging mails and pix but are totally different from being OK, once you meet them up in real life. Yeah, you wanna know that, don't you?

Make sure that John understands that every consenting sex really means that all of everybody's limits must be respected. You do not want to make out? Fine. Say that and make it sure that he understands you. If this is a major turn off for him, move on. There are tons of other Johns around.

Use your actual meet up to let him know that you want to have it 'safe' and that you are not into BB-ing.

Make sure that he understands that you may be new to M2M sex but that you have very clear ideas as to what you want to do as opposed to what is it that you do not want to do.

There are plenty of web resources that might be helpful when it comes to bottoming for the first time. You want to spend some time reading that stuff and making sure that you know, what's ahead of you.

Finally, IMHE, first time penetrations tend to be painful. (The operative word here being: tend to...) So, be prepared to take some pain and be prepared to understand that every top has his limits when it comes to understanding and patience with his bottoms.

Limits work both ways and ought to be respected.

Stay safe and have fun.

KD

nsanick: You can do way, WAY better than a 52-year-old who is pressuring you to kiss when you aren't ready.

Anytime somebody chases after people less than half their age, chances are the person is a creep. The fact John is pressuring you in some ways fleshes that picture out, so to speak.

Pass on this John. Go back to craigslist. Find someone closer to your age (20s / 30s), hotter, more compatible to your needs and frankly, nicer.

As someone said: meet the guy in public, in any case. Always be willing to say no / walk away. Never let yourself feel pressured or guilted into anything.

BTW, I am 7" and thick and I had an anal virgin take me with no problem. Partly because I was VERY sensitive to his needs and took a long time prepping him and working with him. I'm only saying, that's key.

Take charge of the situation ...
 

no one should be pressured to do something he/she does not want to do, particularly in a sexual encounter. There are many guys looking for sex who don't enjoy or who don't want to kiss another guy. If you think you're that type, communicate this. If you're the poster, put this in your post; if you're replying to a post, make this clear in your reply. If a guy you're interested in does not acknowledge and accept your likes and dislikes, keep looking.

GornyHuy's right
 

The red flag here is that he's adamant about a certain kind of contact. That suggests that he has a predetermined agenda to which he expects you to conform. You don't know him well enough to know how he reacts if and when you don't want to go along with his agenda - enforced kissing may be the tip of the iceberg.
--Best to find someone with whom you can totally relax and be yourself, someone in whom you develop trust so that the sex is not fraught with constant worries about safety (of all kinds).
--As for someone else's comment (above) that you can do better than a 52-YO man... I once had occasion to spend an afternoon in a gay adult cinema frequented by a lot of college basketball playeres. During a dark scene, a tall, slim, handsome blond-looking guy stood at the end of my row - I had NO objection, he sat next to me, in no time his muscular hand was on my knee, and things proceeded most interestingly. When the lights came on, I realized he was not a college kid; his hair was white, and he was probably in his 70s. I freaked for 2 seconds, then realized that the hot sex we just had was not affected by age, but by interest. Learned me a lesson: --- Go for the guys that attract you, not just for the cookie-cutter matches to your "type."

Run for the hills. its just not worth it and on your first time especially.

Hey! Older guy here that hooks up with younger guys.

I am fortunate not to look as old as I am and I get along with younger guys anyway. I never pressure any of the younger guys to do anything they dont want to do. If this guy is trying to make you fit some mold, keep lookin. If you are into older guys , there are those out there that are more easy goin than that.

As for fuckin. The first guy that had me was 8" and very thick. It went well because he took the time to strech me before he stuck that monster in my hole! He started with 1 finger , then 2 then a bigger dildo then the real thing!

Look for somebody that is willing to go easy....this guy doesnt seem to be it