—O-Less In DC

If your lovemaking is as vague as your letter-writing, it's no wonder she's peakless. When you say she doesn't "O" when you "make love," are you referring to intercourse exclusively? And when you report she "never has," do you mean she's never cum during intercourse or never at all? These are quite distinct scenarios. What would Mistress Rowena do? RTFM, i.e., get a book. Oh, you've already done that. Change boyfriends? Well, the fact that you're concerned about her pleasure already puts you above 95% of the men she could be dating. But, unless the books you've read were printed by the Vatican press, nothing I say here should be news to you. Most basic How-To-O manuals will first point out that the musician practices in private before performing in front of an audience, even an audience of one. In other words, Ms O-Less should be spending some quality time with her vibrator. Once she has let her fingers do the walking and explored what gets her off, she can show you. If she is unable to give herself an orgasm manually, tell her not to give up. The idea of not being able to jerk yourself off many seem mystifying to a male, but female plumbing is more quirky and individual. Suggest she check out "Sex for One" by Betty Dodson, particularly useful if she needs to increase her comfort level with masturbation.

If her solo flights soar just fine and the issue is that she can't cum during intercourse, then you need to refine both your technique and your expectations. Women, as you have doubtless read by now, usually need clitoral stimulation to orgasm. So, for her to cum from intercourse, get the clit involved. Now, there's more than one way to stimulate a clit. You could take the direct approach, if you both want her to cum with your cock inside her, by fucking in a position that allows you or her to stimulate her clit manually. One position I would recommend to start with would be on her knees, you plowing from behind. She's got free access to her clit to stroke herself to o-ooh,-ooooh. Another good option is her on top. You can reach her clit too in that position, or at least watch.

A little more effort with the ol' bump 'n' grind may reward you both with hands-free orgasming. Two options to play with here: When you're on top, slide up higher than you'd ordinarily go so that your pubic bone, as well as the base of your boner, rub her clit. Instead of thrusting, undulate, slide your body back and forth over hers, maintaining that pube/clit contact. Get feedback; adjust accordingly. Don't despair if you don't hit pay dirt w/this technique; it depends on your individual anatomies and how your bodies fit together. Instead, flip over. She rides you like you're a stallion and leans forward like she's approaching a big jump. She finds the angle that makes optimum pube/clit contact and grinds against you in whatever rhythm does it for her. Bonus if it gets you off too. If it doesn't, enjoy the ride: Pay attention to her expressions, her moans, her muscles clenching on you. Damn, I'm getting hot just thinking about it.

Finally, don't let your quest for the Big O become the dominant theme of your lovemaking. If you're more concerned about her cumming than she is, it may be a sign that, rather genuinely caring about her pleasure, you're egotistically preoccupied with your performance. To rate yourself as a lover, use criteria beyond "did she cum?" Ask her what she likes about getting it on with you and what you can do to please her more. And let her know what you like that she does and what other delicious things she can do to get you off too. Because I can guarantee that the amount of pressure she feels to cum is in inverse proportion to the likelihood of her cumming. I can't beat it into your head enough that female O's resist a goal-oriented approach. They need to be coaxed out of hiding with enough time, patience, arousal and, above all, relaxation.

My question is the age old one: Does size matter? Mine is 7 inches long, but not as thick as many I have seen in locker rooms. Of course, it may be that size really just matters in locker rooms, but I can't help but think that being entered by a huge penis would feel different than a small one. Or maybe it is just the initial entry. Also, I have observed that when my penis does penetrate deeply, women seem to respond, so why wouldn't they respond even more if I could penetrate even more deeply...or is it really just about the clitoris?

—An Above-Average Joe

Seven inches, is that all? And thin to boot? Might as well use my pinky.

That's what you're afraid women are thinking. And, just to put your mind at unease, they are. But I don't think you're writing for reassurance that size doesn't matter; I think you're writing for praise. You want to hear that your cock is beautiful, irresistible, delicious and driving your partner wild. But I can't tell you that. In fact, your partner would probably be pretty upset if I were in a position to do so. I could remind you of the basic fact that size at Lake Flaccid has little bearing on size on Mount Everest.

In other words, dicks that appear large when limp don't always expand appreciably when hard and cocktail franks sometimes beef up considerably. I could tell you that most vaginal nerve endings reside in the outer third, or that too deep penetration can result in painful bumping against the cervix. I could dash your hopes by asserting this means width counts more than length. I could reiterate the old adage that it ain't how much of it there is but how it moves. I could point out that certain positions, such as her on top or from behind, can facilitate deeper penetration. I could enumerate what percentage of women in the latest survey said size matters to them (few). I could inform you that, when asked to rate the most important characteristics of a penis, women cite features like scent, taste, shape and curvature more than length and girth.

But the only way you're going to get the ego stroking (ahem) that you crave is by asking your woman, "What do you think of my cock?" Tell her you need to know if it pleases her and what it (and the life support system attached to it) can do to please her more. True, unless she is a callous bitch, she'll be carefully tactful if you ask her how you rate in the size dept. This is the male equivalent of "Does my ass look big in this?" and any woman who wants to get laid is going to tell her male that a) size doesn't matter and b) even if it did, you're hung like an elephant, big boy, now get in bed. Let's face it, a man who is worrying about his dick size in the sack is like a women obsessing over her tit size or cellulite: not fully present in the moment. So, instead of wasting your time comparing wienie size in the proverbial locker room, spend it noticing how much pleasure your dick brings to both of you.

The other night, my boyfriend and I were going at it—I mean really going at it. He was holding me down and fucking me while calling me his nasty, dirty slut—all of which really turns me on. I was so wet that the pussy juice was literally dribbling down my arched back, and his cock made schlorping sounds as he rammed it into me. Unfortunately, I was maybe a little TOO wet, since his (rather large) man-tool slipped out of my pussy and, with his next powerful thrust, buried itself to the hilt in my virgin ass. To say it ruined the mood would be an understatement; I felt like some medieval torturer had shoved a red-hot poker up my bum. It was half an hour before I could move out of the fetal position.

What can I do to ensure this never happens again? What are the chances of E. Coli infection, considering wounds received? And how can I get him back?

—Pain in the Ass

You know what's the real pain in the ass? Fake fucking questions. This isn't a forum for bragging about how wet she gets (in your dreams) and how humongous your cock is (in your fantasies)—try Penthouse. Since no real woman would get within 10 yards of you and your microscopic tool, you've just got to learn that when you squirt too much lube on, slip out and try to penetrate an orifice that is only available on the deluxe model you were too cheap to buy, yes, she will deflate. It's no less than you deserve, you odious bag of scum.

If there's another dickwad out there reading this and thinking, "Shit, man, that's the ticket: Slip it in the back door when I'm doing her doggy style and tell her it was an accident. 'Oh, baby, I'm sorry; you were so wet, it just happened, ungh, ungh.' " I wouldn't try it. At worst, you may not live to fuck another day. At best, you won't be entering any orifice of hers again. If you want some anal action, beg. Women respond to groveling. Once you get the green light (and you will if you ask nicely enough), proceed slooooowly. Start w/one finger (and lots of lubricant). When she's comfortable w/that (and this could take 5 minutes or 5 months), try two fingers (and lots of lubricant). Gradually add as many fingers as it takes (with lots of lubricant) to approximate your penile girth (I'm resisting the pinky jokes w/difficulty here). Then, and only then, free Willy. Pretend, for a moment, that you care if it hurts her, and enter just the tip (using lots of lubricant - did I mention that bit?). As the viselike grip of her sphincter muscles loosens, press on. Whenever she asks you to stop, stop. Wait, request permission to proceed. (This routine is greatly facilitated if she wraps a twitch around your balls and keeps a good hold on it.) Don't anticipate burying yourself "to the hilt" first time in. But if patience and consideration aren't totally foreign concepts to you, you'll get there.

Germs are an unsavoury but unavoidable issue. It should go without saying that you should wear a condom if you haven't both been tested for STDs -- not just for HIV, but herpes, hepatitis and all those other fun bugs. Soap up between anal and vaginal or oral contact to avoid spreading bacteria that reside in the ass to areas where they're not wanted.

Finally, let her reciprocate. Bend over and submit.

Confidential to Jake in OH whose woman likes the "rough stuff": If you had two brain cells to rub together, you would have already thought of the obvious: Ask her. Jesus, why are you men so reluctant to exchange words with the people you swap bodily fluids with?

* Initials erratically modified, to protect the definitely-not-innocent.

In and Out is for entertainment purposes only. We are not licensed sex therapists or certified psychological care providers in any way, shape, or form—not that you should believe those bozos, anyway. We are, however, much more amsuing.