Dear Em & Lo,

I will cut to the chase: I’m not bragging here but I have a much larger than average penis (it’s almost 11 inches) and it’s ruining my sex life. Every ex-girlfriend I have had has said it hurts them and one even just turned around and said no way and broke up with me a couple of days later.  I have yet to have sex with my current girlfriend due to fear she will do the same or I will end up hurting her.  Is surgery an option? Or is there any thing I can do to make her more  ‘accommodating.’ I really need some advice!

The Jolly Peen Giant

Hi JP,

We suppose if you complained to your straight guy friends about this, you’d probably get a lot of responses along the lines of “Cry me a river,” and “I wish I had your problems” and “Oh, poor wittle baby with a big probwem, boo hoo” and so on. But just as a particularly small penis can cause a lot of sexual difficulties, insecurities and/or fears, so can a particularly large member. We’re not medical experts and cannot speak to any surgical possibilities (if there are any), but we can give you a few tricks and techniques to try before you talk to your doctor about medical intervention: 

1. Insist on foreplay. And lots of it. Think extended erotic buildup. In other words: tease, tease, tease. The more turned on she is, the more room there is in the back two-thirds of her vagina, the better penetration will feel to her, and the greater chance for her own natural lubrication to supplement all the man-made lube you’ll be using (see next point). Also, if perineal massage by doulas works for women in labor, it just might work for you, too! 
2. Use lube!  Do you know what we like to say about lube in the sex biz? Too much lube is almost enough. And in your case, we’d say, double it. A water-based or silicone lubricant can really help ease friction. Keep reapplying it throughout the sesh (a pump dispenser is great for one-handed reapplication). And don’t be a cheapskate — K-Y might seem like a bargain, and it might be the closest at hand in your corner drugstore, but it can’t compete with the higher-end, longer-lasting, heartier lubes available at sex toy outlets like Goodvibes.com. There you can get sampler packs to experiment with until you find the one that helps you fit together the most comfortably. Or treat yourself to a nice bottle of love that’s glycerine free, paraben free, and fragrance free like Lelo’s Personal Moisturizer. We’re guessing that something sturdy like Maximus – popular with anal sex fans — will help get the job done. (Though let it be stated for the record that we don’t see a lot of anal sex in your future!)
3. Try condoms (if you’re not using them already). Not only will it help protect you against STDs and pregnancy (duh), it may also help facilitate a smoother entry and less internal tissue tearing, especially if it’s lubricated (just avoid the ones with Non-oxynol 9.) And make sure the added lube you’re using is compatible with latex. Invest in high quality, super-thin condoms with added sensitivity for you — you don’t want some thick, cheap rubber desensitizing you, resulting in the urge/need for you to thrust harder/faster/deeper to get to your own happy place. In fact, you should come to terms with the fact that hard/fast/deep thrusting is just not in the cards for you. But not to worry — see our next two points! 
4. Do it differently. Jackhammering is not the only way to get busy — in fact, for most women, it’s a terrible and unsatisfying way to have intercourse. With penile penetration, focus on shallow penetration and slow, gentle thrusting. Remember, the outer third of the vagina tends to be more sensitive, anyway. Plus, shallower penetration givers you a greater chance of stimulating her G-spot (if she’s into that).  Think of the missionary position as your friend — if you think it’s boring, then experiment with the Coital Alignment Technique.  Or hold still so your partner can control the motion (rather than vice versa). Or let her get on top so that she can set the pace (rather than vice versa). Play around with other positions until you find the most comfortable ones — for example, if regular doggie style feels too deep for her (which we’re sure it will), have her try lying flat on her stomach and keeping her legs fairly close together. Call it Sleeping Doggie.  Try sex on your sides, to limit the depth of penetration as much as possible. You could also try having her put her hand on the base of your shaft to keep you from entering her up to the hilt. 
5. Stop thinking of intercourse as sex. Those two things are not the necessarily the same. Intercourse isn’t the be-all end-all of sex, despite wide reports to the contrary (gross exaggerations, if you ask us). Spend lots of time on naked grinding, massage, “titty fucks” (just please, for the love of god, don’t call it that), handwork, oral sex, sex toys, mutual masturbation, etc. In two words: reconceptualize sex. As long as you’re having fun and getting off, those things can be just as good (if not better, especially in your case) than the old in-out.  Instead of thinking of intercourse as the main course, think of it as the occasional side dish or dessert of an already satisfying meal. 
6. Encourage your girlfriend to work on strengthening her pelvic floor muscles. Many natural birth advocates encourage preggos to do their Kegels religiously, since having toned PC muscles not only means you can contract them at will, but you can also relax them when it’s time to make way for a baby to come out — and we don’t see why this wouldn’t work in the opposite direction in your case. 
7. Experiment with sex toys  first. This would require some time, effort, cash, and an enthusiasm for experimentation, but you could try getting a series of increasingly large dildos or vibrators to help her work her way up to your level. The idea isn’t to stretch anything (the myth of the literally loose woman still endures), the idea is to just condition her pelvic muscles. 
8. Try it at different times of the month. She may find that it’s more or less comfortable at different times during her cycle. For example, you may find you have to abstain from penile penetration the week before and during her period.  
9. Try to date tall women. We know, we know, you can’t really help who you fall for. But it would be way better to team up with a woman who’s your height and plays in an adult women’s rugby league rather than going for a 5-foot, 100-pound yoga instructor. 
10. If all else fails, you can always become a porn star. Just kidding. 

Good luck to you…and even more luck to your girlfriend! 

Em & Lo