I may be losing my virginity sometime soon (with the person I’m dating, who’s also a virgin – we’re 19, if that helps). Basically, we trust each other (we’ve been best friends for months before dating), like each others bodies, and have done more or less everything except penetrative sex (manual, oral). I wanted to know if there’s anything we can do to make it hurt the least possible and for both of us to enjoy our first time as much as we can?

Also, he told me he would like to skip the condom during the first thrust, but obviously use it in the following – if I wouldn’t mind so -; and I actually find that right, as in the “official loss of virginity”, that first act. That’s why we’re thinking about holding on for a while as we are, doing the other stuff we have been doing; he’s going away to see his family during the summer, anyway; and do it, eventually, once he comes back.

That way I’ll have time to start taking the pill and everything (I’m not planning to skip using condoms, I would rather just feel twice as protected – and he’s supportive of that). What do you think about this? Good idea, bad idea? Any more advice you find relevant? Sorry for this being so long, and thanks in advance. XX 🙂

I do not advise that you skip using a condom, ever, but especially for the first time. Condoms desensitize the guy a little bit and if it’s his first time, he’s going to need all the help he can get to last as long as possible for you. So less sensitivity will really benefit you both in the long run.

Even if he enters you without a condom and then backtracks and puts one on, you’ve already exposed yourself to precum (which often has semen left over in it from previous ejaculations) and STI’s. So you’re already risking everything you’re trying to prevent. Also, it’s just not a good idea because once he’s in, then you’re tempted to keep going. Your mind makes all sorts of excuses as to why it’ll be okay or that he’ll only do it a few more times and then he’ll put one on. Then you might end up convincing yourself that if you use the “pull out” method, you’ll be fine, you’ll think it’s no big deal, and so on…

Point is, it’s a slippery slope and you don’t need the temptation to practice unsafe sex. Believe me, pretty much all rationality goes out the door when you’re having sex and people make a lot of really stupid decisions that they never would have made if they were thinking with a clear head.

And, yes, definitely have a back up plan. Condoms are only about 85% effective in preventing pregnancy and STI’s. So using a condom and being on the pill, NuvaRing, etc. is (in my opinion) the most effective and safe way to have sex.

Read this post I made about the importance of foreplay and how to make your first time as enjoyable as possible. 🙂