Let Him Be "The Tutor"

I happened to come across your blog page and I have a question for you. I am 18 and have had sex numerous times but I have never given a guy head. It's not that I don't want to I just haven't yet and now I shy away from it because I feel like I'll be bad and guys will expect more. I would really like to please my boyfriend and surprise him and give me a blow job but I'm kinda scared because I don't know what to do exactly. I was wondering if you could give me some personal tips or advice.

I think I would approach this a slightly different way. Surprises are nice and all, but giving head isn't a paint-by-numbers activity. I don't really have a technique, per se, other than having been trained into a relaxed gag-reflex which makes deep-throating easier. Mainly, I try to make adaptability the theme when it comes to giving head, to either gender. Everyone likes it a little different.

If I were you, I would wait until I was making out with him sometime, pick a good moment and say something like "I want to try something ... I've never felt comfortable enough with a guy to suck his cock before, but I do with you. I don't want to disappoint you though. Will you let me suck yours, and tell me what you like and want me to do while I do it?"

That specific language may be a little too much for you, but I think you get what I mean. A lot of guys like the idea of boldly going where no other guy has been before. I think this explains the stereotypical heterosexual male's fascination with lesbians. So let him know he's the first, be enthusiastic when you're blowing him, and let him guide you*

I really don't think you'll go wrong with that approach.

A few mostly universal things:
-Watch your teeth (some guys like teeth. In my experience, the majority do not)
-Ball licking/sucking is usually appreciated
-If you can't deep-throat and his cock is too long for you to take all the way in comfortably, use a hand, or both, on the base of his cock to supplement what your mouth cannot do
-making eye contact with him when his cock is in your mouth is really hot







*guide you verbally. A lot of guys like to hold your head and fuck your mouth. Some women like that, but many do not. I would reserve that level of cocksucking until I was a little more comfortable with the activity itself if I were you.

Myth of the Simultaneous O

I am unable to allow myself to orgasm with any man I have ever been with. I am able to orgasm with myself using a clitoral vibrator. I think this is because I was the victim of incest. This hasn't been a problem until now, I have found the love of my life who brings me closer than anyone else. I desperately want to come when he comes. What is the best small unobtrusive toy for me to use (I do need powerful stimulation) during sex to make this happen? Thanks so much in advance.

Let's not put the cart before the horse here, darlin'. Not being able to get off from penetrative penis-vagina sex is a completely separate issue from not being able to get off with your partner there at all! I'm not quite sure which camp you fall into, but I'm going to address this as though you can't come in his presence, because if it's just that you don't come when his cock is fucking your pussy, I have some potentially bad news for you: It is entirely possible you never will. Do some googling and you'll find that a good deal of women only come from clit stimulation, and often times, the friction from penis-vagina sex isn't enough, even if she's on top. So, we need to stop you right here thinking that you are somehow deficient because intercourse doesn't get you off, it that is what you're saying.

So, before we get you to have simultaneous orgasms with your man, assuming that is even possible for you, we need to get you comfortable having an orgasm when he's there. You come from clit stim with a vibe on your own. YAY! But have you ever come from fucking yourself with an insertible, sans clit stim? If you've tried but it hasn't worked, it makes perfect sense to me that you can't come from traditional male-female intercourse. If you haven't tried ... buy yourself a dildo or insertible vibe and get to it, Missy!

Your next step is going to be to masturbate in front of him with the vibrator and/or insertible, or let him use it on you, until you orgasm. I'm going to suggest you need something more than a "discreet" vibe for this task. I want you to try something that is almost guaranteed to make you come: one of the vibrators I discussed here. He should not be fucking you with his cock during this exploration (though you can certainly finish off with that, if you like). This is about both of you exploring your body and you getting more comfortable with him. You're going to have to be patient and it's possible it won't work right away. But if you do this, you're going to become more comfortable, which will relax you, which is most likely the barrier you're having, and this most certainly has something to do with the incest in your past. I hope you're already doing this, but if not ... you should be seeing a therapist to deal with the issues molestation can cause.

Now as for the simultaneous orgasm thing: I really wish people wouldn't make this a goal. For some people, it happens by chance. I frequently come when my male partner comes in my pussy or ass, but that's because I've got a hair-trigger ograsmic response. This isn't the case for most women. In fact, some women spend most of their lives never coming with a partner. Have you read my ex's blog? In a recent entry, she describes the first time she ever came with a partner (or in this case, two) ... at 44. Some couples are in-tune enough to come at the same time. But this requires being able to recognize sensations in your body that are pre-cursor to the orgasm, the ability of one of you to hold off until the other gets there, or to come on command, and LOTS of communication. Even if you do get to the point where you come while he's fucking you, coming simultaneously will just be a stroke (pun intended) of luck.

He Keeps On Going - But Never Cumming

I have just become a fan of your blog - and I have a question that I hope you can help with......

Simply said - my boyfriend can't cum. Though he can stay hard forever, and make me have orgasms like I never have had - he can't get there. Nor can he get there through oral sex.

He warned me about it before we ever had sex - saying that he has NEVER cum with a woman (we're both in our 30's). It seems he was scared by the first girl he was ever with, she told him he was "dirty and gross" right before he was about to get off.

How do I get him to be able to cum with me????


My first question is, can he cum, ever? Does he come when he masturbates on his own? If it is only that he can't cum from sex with a partner, then I would suggest always having him finish himself off after he's fucked you to your satisfaction. Get into watching it. Talk dirty to him while he's stroking his cock, or let him talk dirty to you. Or talk dirty to each other. Let him cum on you if you're into it: your tits, your stomach, your neck, and your face are all good targets. From there, see if he can teach you to jerk him off the way he likes. If he can get off from your hand, he may be able to train himself to cum with you otherwise. Give it a shot! Even if it doesn't solve the problem, watching him jack off will be hot!

It is possible it is a psychological thing, stemming from his early experience with the woman calling him dirty & gross. (Small aside: we hate her! Humiliation like that is only cool if both parties are consenting. Otherwise, it can be truly damaging). Just as it is one of the major causes of impotence, performance anxiety is a leading factor in inhibited male orgasm. It would be best for him to work through these issues with a therapist. That might not be something he wants or thinks he needs to do, and you can't push him into it. Tread lightly if you discuss this option with him.

If it is all in his head, the masturbating himself to completion after fucking you senseless may or may not work, but is definitely an option to try. In the meantime, just be loving and reassuring to him that he is good, and sexy, and not dirty (some of us like being called dirty, but your man is clearly not someone who has eroticized that kind of humiliation), and try not to add to his anxiety by pressuring him. It is wonderful if you want him to experience that kind of pleasure with you. But if you want it because it makes you feel like less of a woman, he's going to know that and that added pressure is only going to make the situation worse.

If he truly never cums, even alone, is it possible your boyfriend is on an anti-depressant or some other prescription medication that inhibits orgasm? If he is on any medications, research them for sexual side-effects. Depending on what the medication is for, there might be alternatives that have different side effects that don't inhibit orgasm. It is also possible that whatever the medication is for, the sexual side-effect is less detrimental to him than not taking it. In that case, it may just be something you have to live with. As long as you are satisfied, and he is happy with your sex life, I wouldn't let it bother me very much.

It is also possible he has a physiolgocial problem, that he may well be unaware of. A number of physiological conditions inhibit orgasm. Low testosterone, elevated prolactin levels, any neurological disease that reduces peripheral sensation or impairs functioning of the sympathetic nervous system, injuries to the spinal cord, following surgical interventions, etc. He will know if he's had any injuries or surgeries that might have an affect. But having his hormone levels tested might reveal that it is a physical problem that can be regulated through medication or horomone treatments. This is probably the easiest of all of the possible issues to remedy.

Quick Sex Tip of the Day - Anal sex is not effective birth control

From our good friends at Wikipedia, comes the following:

"Anal intercourse, however, is not a reliable method of birth control, as it is still possible for semen to spill into the vagina, although very rarely, and result in pregnancy."

Birth control and STI-prevention aside, I for one always advocate the use of condoms for anal sex, even between fluid-bonded partners, simply because it makes clean up easier, and decreases the risk of spreading bacteria.

All The Cool Kids Are Doing It

As the The Assturbatrix™ it seems incumbent opon me to post a picture of my ass on my blog, given my hot ex has done it and she isn't reviewing anal sex toys.

In some weird way, I feel I must keep the chain going.



I'd apologize for the bruises for those of you who are squicked by such things, but the person who gave them to me might be offended. And I happen to think they're pretty.