San Francisco Sex Information

Q: I’m a 20-year-old woman who has abstained from most sexual activity up to now by choice, largely because of reservations about the guys I’ve dated. I don’t regret that at all, but now I’m pretty inexperienced and seeing an older more experienced person. I imagine I feel as weird asking basic sexual questions as he does answering them. It also doesn’t help that I’m entirely self-educated in just about everything sexual (seriously, no one has ever straight-up told me where babies come from. I mean, I figured it out eventually, but still. Come on.), so there could be holes in my knowledge.

So here’s the problem: I’m fine experience-wise with my own pleasure because of, you know, owning a vagina that’s at my disposal to experiment with, but I’m not sure of how to go about really basic manual and oral sex on the male side. My boyfriend is comfortable with (and very skilled at) giving both manual and oral stimulation, and I feel badly not properly reciprocating. I’ve given a couple hand jobs, but I feel uneasy about it, and not sure if I’m “doing it right,” which is one of those awkward questions I’d rather not ask my boyfriend while I’m trying to give him an orgasm. I haven’t attempted oral yet, and the thought of it makes me pretty nervous. I know people’s experiences differ, and that I’m just going to have to live and learn at some point, but I’d like some advice on how to go about things, especially on the oral side, and hopefully come close to giving as much as I’m getting.

A: The best advice we could give you on how to please your boyfriend is to ask him. Seriously, even really experienced people need to ask their partners what they like because every person is different. So as you are doing things, ask him questions like, “is this good?” “should I go harder?” “do you want it faster?” etc. Also, it could be that your partner likes answering your questions. It can be really hot for some people to get to “show you the ropes” and teach you the way they like things. Think about it- would you mind answering questions about how you like to be pleasured? Probably not, if it means your boyfriend is better at pleasing you!

That being said, we do have some general information on what many guys like for oral sex. First, be careful with your teeth- try not to scrape or bite him. Second, the head, specifically the underside of the penis towards the top, is the most sensitive part. Many guys like to have this area licked, massaged, or played with. For some, however, this part will be too sensitive, and too much stimulation could irritate your partner- which is why you have to ask him.

Another tip for oral sex is to not try to put his entire penis into your mouth. It probably won’t fit, and you’ll probably just end up choking on it (not so sexy). So use your lips, tongue, mouth to lick and suck a little along the sides or around the top and use your hands to stroke his shaft where your mouth is not.

For hand jobs, the general idea is just to stroke his penis, much like he would if he were masturbating. The best way for you to learn how to do this is probably to have him masturbate in front of you (try asking him to touch himself for you), then try to duplicate what he does. In general, though, you want to stroke him up and down, slowly at first then faster as he gets more turned on. Lube can be really helpful with hand jobs because less friction = more pleasure. Ask him if he wants it harder or softer, faster or slower.

You can also try playing with his balls, either by licking them or gently rubbing them with your fingers, either as part of a blow job or a hand job.

You might also try looking at Very Koi, which has some tutorials for masturbation and oral sex. It might have some ideas or tricks you could try.