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Reader Question – The Right Time

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.

Congratulations on finding someone that you feel close enough with to get physically intimate!

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.

8 comments to Reader Question – The Right Time

  • cuntstorm

    i’m with shay on the “whoa! anal but not vaginal?” thing. a lot of people i’ve known who have gone that route have chosen it mostly because they’d been led to believe (through sex ed, media, etc.) that vaginal sex was some kind of pure holy grail, which it definitely feels like, but its also (at least for me) not really a biggie, something to be preserved. so whatever you choose to do, good luck! and have LOTS of fun! ;)

  • Nitin

    well thats kinda.. nice.. i mean if hes gonna get it hes gonna do the anal first .. oral is the safe route.. but anal is the one.. i could say he lucky in some way to get some of that anal action that soon..

  • Yvette

    My progression went from oral to anal to vaginal.

    Why anal before vaginal? Well, I was paranoid that condoms wouldn’t be ‘good enough’ birth control.

    Of course, oral was with one dude, but I wasn’t ready for more penetrative with him anyway. Anal with the next guy I got involved with, which was a fuck-buddy deal. Vaginal with a third guy I got involved with (when I finally got on The Pill).

    My first anal experience was wonderful! The second go-around, not so much. Though with my current partner, anal is once again bliss.

  • Anonymous

    Something I don’t believe anyone (including you Shay… naughty girl) has mentioned is that condoms should be on hand FOR EVERY SEXUAL ACT not just vaginal sex…

    Trust me – the STD’s you can catch by kissing alone are scary. After having to provide “second opinions” on std checks in a brothel I cannot recommend condoms highly enough for EVERYTHING!!!

    Sorry to kill the mood but it had to be said.

    (PS: I’m still here Shay – I’ve just been lurking for the last couple of years xox)

  • Shay

    Cuntstorm – maybe we’re just old fashioned, kids today seem to be all over this anal thing (mostly worried about “preserving” their “virginity” though), but for me it was always something even more intimate that you saved for when things were really serious: doing anal with a guy meant that you were practically ready to marry him lol.

    Nitin – see, I really don’t get this obsession with anal, maybe it’s because I’ve never been with a guy who was more interested in anal than vaginal. It’s fun, yeah, but LOTS of stuff is fun.

    Yvette – ahh so anal as extra birth control; when I was younger and more paranoid, I just used spermicidal foam along with condoms. haha

    Thanks Cuddlestlut – good to see you around again ^_~ – you’re completely right, even with oral it’s important to use condoms and dental dams, because there is unfortunately more to worry about in the world than just getting pregnant.

  • Randi

    I think you’re right in that it is all in a girls mind – she feels more innocent and “pure” if she can say that she is still technically a virgin. However, I haven’t been a virgin for a LONG time, and I still feel as though I’m more dirty when we talk about trying anal again! (Yeah, wasn’t a very good try the last few times…)

  • Anonymous

    Anyone who has anal sex and still calls themself a virgin is fooling themselves. Also, I am amazed that she is worried about boring her man!? I hope he realizes what a wonderful woman he is getting a chance to be with.

  • Anonymous

    Anal sex puts you at the MOST risk for disease. The tissues are thin and easily torn so your bloodstream can easily be exposed to diseased fluids.

    In comparison the vagina can safely take much more powerful activity, and with proper condom use, is much more comfortable and safer from STDs.

    It could be that this girl is religious and misinformed. I have heard that some virgins are lead to believe that anal sex is a good way to avoid having “premarital sex” (vaginal).

    Trust me, it’s sex either way.

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