Dear Em & Lo: My Boyfriend Is Too Big for Me

Dear Em & Lo,

My current guy and I get along great, but we may not be sexually compatible. He has a really thick penis (think large cucumber), and I seem to be too small! We have not had successful intercourse because it hurts me way too much. Have you ever heard of this problem before? Are there exercises I can do to stretch myself so he fits? I’ve already had two children, so this is a real mystery!

— Between a Rock and a Hard Place

Dear BaRaaHP,

Sure, we’ve heard this before! Sometimes everything else fits perfectly — your personalities, your taste in movies, your complimentary immune systems that would ensure fit offspring. Everything except your naughty bits. All is not lost, however. There are some things you can try to help improve the situation.

First and foremost, use lube — and lots of it. You two should never go without when it comes to intercourse: keep a pump dispenser of water-based or silicone lubricant by the bed and apply generously and often; it can really help ease friction.

Next, really work on strengthening your 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. You could even try getting a series of increasingly large dildos or vibrators to help you work your way up to his cuke.

Finally, we’d recommend trying different intercourse styles — contrary to popular belief, it doesn’t always have to be deep pelvic thrusting, a.k.a. jackhammering. Try shallow penetration: the outer third of the vagina tends to be more senstive, anyway. Plus, that way he’ll have a greater chance of stimulating your G-spot (if you’re into that).

And remember, there are plenty of ways to have sex besides intercourse: try frottage, manual sex (i.e. handwork), mutual masturbation, oral…though, in your case, that may be a whole ‘nother column dedicated to lock jaw.

To quote Tim Gunn, make it work!

— Em & Lo


  1. I have the same problem with my boyfriend and I find that these columns are really unhelpful. Lube only helps temporarily but it doesn’t help the psychological effects. It is hugely frustrating for both parties and not only this but it ruins ones confidence and self esteem. For my partner and I enjoying a good sex life is very important, it has got to the point where we are discussing having a threesome so we can experience and enjoy ‘normal sex’. We love eachother so much and everything else in our relationship is great but this has been ruining everything. I am starting to think there may be something wrong with my vaginal entrance as it only hurts around the outside – but doctors are unhelpful and use the ‘relax and use lube’ line every time. If only someone would take me seriously because it may result in us ending the relationship now.

    1. Get thee to a sexual specialist (since you regular doc isn’t listening) asap to make sure nothing is organically malfunctioning; but really, we push babies thru this thing (and, yes, I’ve done the “mandingo” penis thing and I’ve NOT given birth. My issue is actually depth, not girth). Cowgirl is a great position for jumbo peen-i, we control the motion and depth. And, lube is essential. Just when you think you have enough? Use another handful, no such thing as too much lube.

    2. I sooo hear you. This has been an issue for me a few times in the past. Sometimes women are just.. well smaller. I’m a smaller framed person (not skinny, but.. my body type) so maybe that’s it? I have to second talking to a Dr though because a lot of my problem was chronic dryness. I make sure to stay hydrated now, added some things to my diet, made sure my pH is in balance, and also getting a copper IUD added a lot of uh… natural moisture. Sorry for the overshare lol. The other thing is it’s possible you may have vaginismus. I had one partner who wasn’t treating me well (long long term relationship gone wrong) my body would literally clench shut, this is after a nearly 9lb baby. Also due to some experiences in my past. Now my current partner is just wonderful and that isn’t the problem but size differences are.

      This is graphic but here goes. When I was pregnant, a midwife recommended I use Evening Primrose oil (break open capsule) to massage the opening to help tone/soften that tissue. It may be worth a try. I *think* its totally safe but might want to look it up. The other thing is that I’ve had “hidden” yeast problems that don’t have discharge but cause pain/dryness. Probiotics have helped that a lot.

      It’s possible you may have hymenal remnants as well that are being pulled or torn. Supposedly some doctors will remove them if they are hurting you.

  2. I’m having th same issue. My new boyfriend and I finally got to the point of attempting intercourse and I found it to be extremely painful. On top of this, he takes a very long time to climax, requiring a lot of foreplay and intercourse. I tried to hurry him along to no avail. It just didn’t work. I felt like a failure because I couldn’t satisfy him. He was understanding, but I want to find a method that works to satisfy both of us. Any suggestions would be great. We did use a lot of lube, but still each thrust was very painful for me. Help!!

  3. More foreplay, more lubrication, and start slow and shallow. Consciously relax yourself as he enters you (Kegels, as Em & Lo said, help this enormously). Have him penetrate you with 2-3 fingers leading up to sex (or do it yourself – I’m sure he’d love it!) to get yourself loosened up a bit.

    Also, a large part of it is mind over matter.

  4. I did go to a naughty lady party once and the very young woman next to me had this problem, she was in heaven when the Penis Sleeve was shown. You can use it for hand jobs, oral or penetration. The sleeve was soft silicone and she was running to the lady to buy hers. 😉 I haven’t had this problem, but I ran to buy mine too, never used it for intercourse, as I don’t have that issue, but it’s a great addition to a blowie or handie! Easy to use and I’ve had nothing but positive feedback. LMAO

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