“I write now to you in a somewhat desperate situation in need of your guidance. I have a gf and we have recently talked of getting “more serious” in our relationship. While it is something I want, I am a bit nervous because I am a virgin and she(while certainly not experienced) is not. Also, even though we have never done anything real serious I did ask her about whether or not she would be interested in any anal play. She said she would like to try anal sex. So my question to you is three-fold: 1. Do you have any advice for a first timer? I know all the basic stuff but im worried about positions/penetration (i.e how hard to you have to push to “penetrate” the vagina) as I don’t want to hurt her. 2. Also, I have read a lot about anal sex (including some fine research on your site) and I know that you need a trusting partner, patience, and lube. But as with the above question, I am unsure as to how much pressure I should exert. Can you help at all? 3. Lastly, I just want you to know that I appreciate all you have done for me in the past as well as the rest of your internet community. Thanks so much!”
Firstly, congrats on finding someone with whom you can explore and enjoy the wonder and good-feeling-ness of sex!
Now, I don’t want to embarrass you, but your first question is really cute. Actually, I’m not really sure precisely how many pounds of pressure it takes to penetrate a vagina – I’ve never found a way to measure it myself. But if you are worried, just make sure everything is well lubricated, go slow, and press steadily harder and harder until you are inside; that should do the trick. You’re not going to hurt her by pressing hard, but you might if you go too deep (but let’s not worry too much about that right now).
I’m sure that once you’re in the situation everything will come fairly naturally for you both – try not to over-think things in advance; it sucks to get stressed out just before having sex (especially your first time).
As for anal sex, I am again not sure exactly how much pressure you should exert – but once again, lots of lubrication and take things slow.
In both situations, you might want to let her be on top so that she can control how fast and hard and deep things go. That way you can ease you mind and be relatively sure that she’s not going to be injured.