5 Ways to Make Sex with the Well-Endowed More Comfortable

Dear Em and Lo,

I have recently found that mythical man that every woman wants and movies portray. He’s financially stable, no ex drama, gorgeous (holy crap is he!), very sexy, and very tall (approx 6′ 3″-4″). The latter part of his good qualities is what’s the issue — he’s TALL. Meaning that everything else in his body is very much in proportion to his height. Catch my drift? We have been intimate recently (first time) and to put it lightly, I’m on a recovery status just short of doctor-prescribed bed rest. Everything else was mind-blowing, even the actual act was enjoyable. It’s after. I’ve tried taking Motrin and using warm compresses but it’s been 3 days and I’m still very sore and even have some light bleeding. I need to know how to lessen this happening again the next time we are together. Please help me!

–Saddle Sore

Dear S.S.,

Ouch! First of all, you probably should give your gynecologist a quick call. She may well tell you she doesn’t need to see you, but it never hurts to check in. We’re not doctors, and although we do ask Dr. Kate (who is a real doctor!) to look over our shoulders whenever questions veer toward the health-related, there’s only so much we can know from afar.

But here’s what we do know: five things you can try to make things more physically comfortable with the tree trunk:

  1. Lube it up! 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. Keep reapplying 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 Good Vibrations. They have a Lube Sampler Pack so you can experiment 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!)
  2. Use condoms. You did use a condom, right? We’re assuming so, given that it was your first time sleeping together; if he didn’t insist on one, then perhaps he’s not Mr. Wonderful after all. But on the off-chance that you didn’t — naughty, naughty — you definitely should next time around. 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.)
  3. Insist on foreplay. And lots of it. If Mr. Wonderful is all that, he won’t object. Especially when you tell him that the more turned on you are, the more room there is in the back two-thirds of your vagina, the better penetration will feel to you, and the greater chance for your own natural lubrication to supplement all the man-made lube you’ll be using.
  4. Do it differently. With penile penetration, encourage your Mythical Man to focus on shallow penetration and slow, gentle thrusting. The missionary position is your friend — if you think it’s boring, then experiment with the Coital Alignment Technique. Remind your boyf that jackhammering is not the only way to get busy. Ask him to hold still so you can control the motion (rather than vice versa). Get on top so that you 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, try lying flat on your stomach and closing your legs. Call it Sleeping Doggie.
  5. Re-conceptualize intercourse and sex in general. Nope, those two things are not 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, etc. 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.

And to all the wishful-thinking guys and size queens out there, take comfort in (and a lesson from) this letter: Bigger isn’t always better.

Big fun,
Em & Lo

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24 Comments on "5 Ways to Make Sex with the Well-Endowed More Comfortable"

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Lube and foreplay really helped me when we first became intimate. After I got used to him it felt wonderful.


Sorry for typos

Interesting article. I know women say size doesn’t matter but like you all state here it does. I asked my gf her preference and given a choice would take XL and X thick. I’m average. Very. When we met we had sex all the time because I chased her around. To make a long story short sex was good at times I felt she wanted a bigger dick. As a guy sometimes I can read her body inside and I know if I had say 2″ more she would cum. So I asked her one day and she said she… Read more »
I just met a well endowed man, been dating for a little over a month he is clearly very well endowed with 9 to 9.5 inches with a 2″ girth. We haven’t had sex yet but plan to soon. He hasn’t had sex in 6 months because of this very reason. I have only been with men 7″ or less my entire sex life. His fantasy is anal which I do enjoy but even with 6″ men, it can be painful. I’m not afraid of missionary style with him but want to please him. Is anal completely out of the… Read more »

2-inch girth? I think that you mean 2-inch DIAMETER. 2-inch girth would be incredibly thin!!

J Whiplash
I’m blessed to be a very well endowed man. Lube is the key. My wife is a obgyn doctor and when she first saw my size she said that she would need lube to handle me. I worried that maybe she wasn’t that into me. She assured me that was not the case, she wanted to be able to walk the next day. We use lube almost every time and it’s great. Not only is sex great but you can have more of it. I remember partners I have been with in the past, we didn’t use lube and would… Read more »

From personal experience i would say 90% of women like average length (which i would say is 6-7 inches) but love alot of girth!


I’ve recently hooked up with a well-endowed guy. The sex is amazing and my body craves him. I’d like to see him more often and probably will in the future, but as we’re a relatively new couple, we have a lot of mutual discovery ahead. It’s good to be able to read posts here by other people in the same boat.