“I’m a long time viewer, first time poster. I need some advice really badly. You see, I finally met this boy that I really like and I want to get… more involved with him. I don’t think I’m ready for vaginal sex just yet but I want to maybe try some other things like anal and/or oral. Although I’m a virgin, I know that he isn’t and I want everything to be perfect for us so that when we do work our way up to vaginal sex I’ll be ready and it’ll be fun for both of us. Can you give me any tips on starting out with oral/anal sex and when it’s the right time to have vaginal sex or not? I also want to know if you think that there is any way I can make it fun for him so he isn’t bored with me because I’m not experienced and he is.“
I have to say that your e-mail really threw me for a loop – you don’t feel ready for vaginal sex, but you feel ready for anal?! Usually anal sex is what people work their way up to, since it requires so much more trust and care. It’s a fun orifice, but it’s not really designed to be treated as roughly as a vagina can be; which is why most (straight) people experiment with vaginal first and save anal for later.
Anyway, that’s neither here nor there, and isn’t want you wanted to know.
So, first of all, don’t stress out about this stuff. Don’t worry that your boyfriend if going to dump you if you don’t move fast enough for him – a guy that would isn’t worth your time (or your virginity). Take things slow and wait until you’re ready, wait until the mood is right and you really want to feel this stuff for yourself. I promise that you’ll be much happier and enjoy it a whole lot more.
So how do you know when it’s the right time to try oral? When you are turned on and can’t stop thinking about how he might feel in your mouth and when want- no, need - him to use his mouth on you. Pretty much ditto for vaginal sex: when you’re ready, you’ll know it and you’ll want it (and you’ll have condom’s handy).
Since anal is a little more delicate of a procedure, you might want to wait a little while: until you know that you can trust him to be careful (and not just pound away). Actually, you should read my post on anal HERE well before you get going.
Sex (be it manual, oral, vaginal, or anal) is intrinsically fun, so don’t worry about him being bored with you. Unless you’re just laying there (in which case you probably aren’t ready), you’re going to be a blast, I’m sure.