I’m writing from New Zealand.

I’m a 24-year-old man, average build and height. I am financially stable and independent and have a respectable job. I’m very introverted and almost never venture out and have a small friend circle to show for it, though I do love traveling.

I have never actually had a long conversation with a girl, let alone dated any. Needless to say, I’m a virgin, and paid sex is just too risky for me. I have been very shy about sexuality since early days and have never really opened up to anyone about it. As time passes by, I’m getting even less hopeful of ever finding a soulmate, or even a passing girlfriend. Each Valentine's is a cruel reminder of how I am alone and have made no progress in the year that went by too.

But these are not the problems. The real problem is that because I keep my sexual frustration so bottled up in real life, I have to resort to alternative means to release myself. I’m masturbating up to 8 times a day in front of a camera where numerous men and women are watching me on the other side. At an age when men find emotional stability and control, I’m turning into an uncontrolled teenager and this is affecting my work, my personality and even my understanding of my own being. I’m asking questions about who I am and what I really want.

I don’t know how to break out of this cycle of porn, excessive self-abuse, and then guilt. Please help me.

Sincerely, R

There’s nothing inherently wrong with masturbation or sexual exhibitionism — as long as the people on the other side of that video stream have agreed to watch you masturbate. But if something is affecting your work and your personality, it is definitely a problem.

And it’s the kind of problem that needs long-term work. If your respectable job gives you enough income to afford one, you should seek out the help of a professional therapist who has a neutral or positive attitude towards sex.

You might want to consider why you're feeling guiltyTry to get introspective about the details of what sexual buttons this behavior is pushing for you. Sometimes being able to really name our desires helps us understand them, and that process might help you figure out what’s pushing your sex drive into the "excessive" zone and interfering with the rest of your life.

Look for patterns in your behavior: are there spikes in the frequency of your masturbation shows? Or was the increase steady? When you get the urge to fire up your webcam, look for motivations. Is that desire fueled by libido or something else?

You might also want to consider why you’re feeling guilty and why you describe masturbation as something to "resort" to. I wonder if you’ve set up an either/or situation in your head, as though you have to choose either your masturbatory habits or a romantic relationship with a woman. This isn’t true, and you spell that out in your own letter: "…numerous men and women are watching me…"

Not only are there plenty of women who won’t think your videos are gross, there are some who you’ve already seen get into it.Most women are sexual creatures to some extent, just like most men are. Just like you are. Not only are there plenty of women who won’t think your videos are gross, there are some who you’ve already seen get into it.

So when you see that therapist you might also want work on getting more comfortable talking to women. You’ve already masturbated in front of strangers — something many men find absolutely terrifying. You’ve got more than enough courage to get through talking to some girls, and you might find that easier to do online at first.

In the meantime, the best I’ve got is a very sloppy band-aid. Get out of the house. Go hang out with your close friends, or do some traveling and pack your schedule with outside activities. Just stay in public, where you can’t have your hands in your pants. This won’t solve your problem, but it’ll slow it down for a couple of weeks until you can find a therapist.

And remember, the first session is when you decide whether the therapist is a good fit for you. If they don’t feel right you can always find another one.

My penis isn’t straight (I guess think of a typical banana). Will this cause discomfort during sex?

-J

Since you don’t indicate whose discomfort you’re concerned about, let’s cover both. Starting with you:

Did your curve developed over time? If so, see a doctor who you feel comfortable showing your penis to.

Does your penis hurt when you have an erection? Does it hurt when you squeeze and/or stroke it with reasonable pressure? Does it hurt in a resting state? If the answer to any of these questions is yes, take your penis to a doctor.

If the answer to all of those questions was no, you might want to consider finding a willing partner and giving penetrative sex a try. You can always stop if it does turn out to be uncomfortable — because of the curve in your cock or for any other reason.

There doesn't seem to be any rhyme or reason to who experiences pain from what shape of penisBut is your penis going to cause discomfort for your partners? That will vary.

A brief search of the literature on Peyronie’s disease (a disorder that causes scar-like tissue to develop in response to penis wounds, which then causes the penis to bend, reshape, or shorten) turned up no indication of a correlation between penis shape (or the degree of curve) and discomfort experienced by partners during sex. I did find something pertinent to your problem, though: there doesn’t seem to be any rhyme or reason to who experiences pain from what shape of penis.

I’ve personally been penetrated with a wide variety of phallic objects, including penises that I would describe as banana-shaped. I’ve never found a curve to be a reliable indicator of discomfort in penetrative sex.

See, there’s a reason tampon instructions say to aim for the small of your back: internal genitalia tend to tilt toward the spine. Meanwhile, to stimulate a lot of the most sensitive bits — the g-spot, prostate, and clitoral sponge —the instructions in sex guides say to press towards the front of the body.

Between the angle you want to approach insertion from and the locations of the best places to rub, you’re basically playing a lubed up cross between tetris and billiards. And that’s whether the appendage you’re penetrating someone with has a 90 degree bend, is exactly 180 degrees flat, or has multiple joints. Like a finger. Or a few fingers.

And every single person’s body is different. And sometimes, depending on the day or what level of sexual arousal they’re at, they like different kinds of stimulation.

So, just like everyone else, you’re going to have to experiment to figure out how your bodies fit together best, and how they fit together best in different positions. Pay attention to your partner — their words, nonverbal sounds, and physical feedback like pulling you closer or tensing up. Ease off if they tense up, and ask whether they’d like to stop or continue at a slower pace.

Pay attention to your own body, too. What feels good, what feels great, and what feels like it isn’t lining up. Apply the last four steps of the engineering method: test, if it works only partially or not at all then make changes and test again, and communicate the results whether it works or not.