YesIWantOne saidWhat are some of the most important things u would want to remember if u did it again?
Would u spend the night the first time?
Will he expect anal sex?
How do u spend the first 20 mins?
You know he and u both are HIV and STD negative then what?
Do u think it should be long term or play it as u spend the day?
Does it matter if there is a huge age difference?
Is big good or does that matter?
How do u handle staying in the closet afterwards if u don't want your family knowing u r gay?
Do not set things in stone. Nothing is achieved by limiting your own options even before the actual thing starts.
He may or may not expect sex, or even anal sex for that matter. That's his good right. You can take your time, see if this may work for you, and call the shots when you feel comfortable with doing so.
Spend the first 20+ min figuring out if you like the guy, and more importantly if he is sane or not? Err on the side of safety.
There are many types of knowledge. (See Rumsfeld!) Assume that both of you are perfectly ignorant and use condoms.
Who knows? Take your time. Use common sense, and make decisions as you go.
Age difference is bad for some people. It is irrelevant to the others, and it works miracles for some. Only he and you can decide where both of you stand on this issue.
I'd venture to say that most guys like it BIG. You make up your own mind.
You are meeting another dude for whatever. You are NOT buying the front page of the NYT to advertise this event.
Point out to the dude that you'd like to keep your meeting/spending time together strictly private. You have your reasons, and it does not take a real rocket scientist to figure them out. Besides, even if you were out, and all... you still do not have any obligation to advertise every starting affair/date/hookup/whatever you may be having to the rest of your folks.