Ask Debby Herbenick | Women who "squirt" and a different angle to the size question

Q Is it possible to get pregnant from pre-ejaculation while on the contraceptive pill?
A Getting pregnant from pre-ejaculate while you’re taking the birth-control pill as prescribed is only slightly more likely than Jeff Tweedy leaving Wilco to start a Christian smooth-jazz band. The fluids that make up pre-ejaculate are actually sperm-free. It only gets problematic when these fluids, which are made by the Cowper’s glands, carry any leftover sperm in the urethra out of the body with them. If a man peed (thus flushing out his urethra) and then put his penis inside a partner’s vagina a short time later, without ejaculating in between peeing and sex, then there should be no sperm available in the urethra to get swept along, and thus his pre-ejaculate shouldn’t pose a pregnancy risk to his female partner. On the other hand, let’s say a man and woman have sex and he ejaculates, then they sit around and make out a little and start having sex again. In that case, there are likely sperm hanging out inside his urethra and his pre-ejaculate could indeed sweep the sperm through the urethra and into his partner’s vagina during round two of sex. However, if his partner was taking the birth-control pill as prescribed, then she shouldn’t be ovulating (birth-control pills prevent pregnancy by preventing ovulation). If she’s not ovulating (which means her body isn’t releasing an egg), then all the sperm in the world could be inside her vagina and she still wouldn’t get pregnant. All that said, it’s better to be safe than sorry and keep pre-ejaculate outside of a woman’s vagina, in that rare chance that sperm are waiting inside a man’s urethra and also because unprotected sex—with ejaculate or not—carries the risk of sexually transmissible infections. Please consider using condoms if you’re hoping to reduce your risk of pregnancy and STI.

Q I’m sure you must be so over the size question, but I’m in a peculiar situation. I’m a bisexual man in my early thirties. I had several girlfriends before I was ever with a man, and each of those relationships involved pretty good sex. Then I was single for a while and hooked up with several men. I noticed that almost all the men I was with were better-endowed than me. I’m five inches long and four inches around but never felt uncomfortable or inadequate when I was hooking up with these men. However, now I’m in a relationship with a woman I really love and who I could see spending the rest of my life with. But when we try to have sex, I feel insecure and nervous thinking about her past boyfriends and how they were probably bigger than me. I’m so nervous, in fact, that I can’t stay erect. I’m hard while we make out, but the minute the clothes come off, I freak and it’s gone. I’ve been honest with her and told her about my past, how I feel, etc. She says size doesn’t matter to her in the least. But that only made me more insecure because all I heard was “Yes, your dick is small, but it’s okay.” I feel like now that I know how I measure compared to other dudes, I can’t possibly please her. Any advice how I can get over this?
A Look, the fact is that a five-inch-long penis—while well within the normal range—is on the somewhat smaller side, and you know that from being with other men. You may also have noticed that there are plenty of men who are shorter or slimmer than you. But being slightly on the short size of average doesn’t mean you can’t be a great—check that, amazing—lover and partner. There are guys with eight- or ten-inch penises who are cool people, but there are also guys with huge penises who are dishonest, disrespectful, condescending or so entirely into themselves in bed that they could care less what their partner feels. Plus, big penises are uncomfortable for many women. You need much more than a big penis in order to please someone for longer than a few nights; ask anyone who’s been there and they will tell you that they’d rather have a smaller penis attached to an attentive, sexy lover than a throatful of penis attached to a jerk. When your girlfriend tells you size doesn’t matter, she’s trying to reassure you that things are good and she’s happy. But your self-defeating inner critic is saying you’re not good enough because you’re not bigger. I can give you all the penis information in the world (e.g., you’re within the average range, most vaginal nerve endings are in the first two to three inches, etc.), but unless you kick a little inner-critic booty, there’s only so much help that common sense and statistics can offer. Next time the evil voices sneak up on you, try replacing them with positive words such as “She thinks I’m hot, she loves my penis, we have amazing sex,” and so on. Time and again, it has been shown that you can boost confidence—and even enhance sexual arousal (including erections)—by focusing on telling yourself positive, exciting stories. Try it and see if it works for you.

Q A few years ago I had a girlfriend who “squirted” quite profusely when she had an orgasm. This really turned me on. No other woman who I’ve been with has done this. Now that I am newly unattached, how could I try to find a woman who squirts when she comes? This is not something I can bring up in casual conversation. Short of trying to find my ex-girlfriend, wherever she is, how can I try to hook up with a woman who has this quality that excites me so much?
A Sometimes I wish I could set up a sex matchmaking service. After all, I sometimes hear from women who squirt female ejaculate and feel embarrassed about it and wish they could be accepted by sexual partners. Other times, I hear from people like you who are itching to find a woman who squirts. There are also people who are interested in finding partners of certain penis, breast or labia sizes or who like certain types of fetish play. The thing is, though, that finding someone who does a certain sex-related thing completes such a small piece of the puzzle. People don’t really write to me saying that everything about their relationship sucks, but they’re staying because they think their partner’s areolas are just the right shade. More often, people choose relationship partners for a whole cluster of reasons, and the sex is just one part of the package. But if all you’re looking for is a hookup or friends-with-squirting-benefits situation, then that may not be impossible. Female ejaculation is certainly not uncommon or unheard of, and many women would love to find a guy who appreciates this quality. If all you want is a hookup, then it’s not that far-fetched or unimaginable to get into a racy conversation with a woman at a bar and somehow lead the conversation to sharing things that you find hot about sex. Maybe you could suggest a game of Truth or Dare, or “hottest sex moments” (where you take turns sharing anecdotes) and see where that leads you. It may take a few tries, but eventually you may find the right sex match. In the process you might scare a few potential hookups away, which is why I’d encourage you to be aware of your intentions and kind in your delivery. Finally, websites like adultfriendfinder.com may provide avenues in which you can be more explicit about your soggy-bed hopes.