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


  1. 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 likes a big dick had a few but they aren’t everything.

    I got her a good looking nice guy. Massaged and they had sex I was like a director. It was fun in the moment. That being me giving direction and I guess living vicariously through his dick that night if you will. So after I said did it feel better and she said yea. She wasn’t being insensitive we are open and I also prefer honesty. So after that I admit it hurt my ego a bit. I never had a problem making a girl cum whether oral or whatever worked. With her it is 40% maybe. It in essence it made me question our past sex. Because if he felt better and could more spots it meant I was having a good time and her an average time.

    So, I bought a penis sleeve and massaged her for awhile out it on and we found she likes missionary better. So I held her ass drove deep and she came. I could of taken it off then done her and came but I felt awkward. Like would she feel it LOL. So… I didn’t cum. I asked did it feel good she said yea it still feels like a dildo but when I’m on too a bit more real. Change is hard for me. Any change. I also feel to be honest not as empowered. I would chase her around love sex but I need to transition into this and it will take time. I love her feeling good. Love her cunning. If I use a dildo and rub her clit she cums. So… It kinda sucks. Anytime I don’t wear it I’ll always be thinking she is getting average sex when as someone stayed her they get used to fuller feeling. Wearing it I feel less of a man. I never had to do that ever. I love her and I ain’t whining I’m being open. Part of me is like bring the other guy back who we both feel comfortable with here and there or wear it.

  2. 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 question? Has anyone successfully had anal sex with a man that size?

  3. 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 often have to wait days in between sex because of soreness for them and me. As an doctor in women’s health, she recommends lube to girls her are with a hung guy or for their first time. With the right amount if lube we can try almost any position without pain. Lube is the key.

  4. 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!

  5. 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.

  6. Even now at my age in a placid state it is over one hand and mouthful. A good eight point five erect so I have had this problem for a while on the giving side.
    Trust me ladies if you Ask for and give more foreplay and tell the man of your discomfort. If he wants to continue with you he will be gentle. The missionary and reverse missionary with your legs closed, the latter allows him to suckle your toes and you to stimulate his prostrate. Both restrict penis depth, if he is very gentle and restricts his thrusting with lubrication the legs act as an extension of your vaginal entrance. Any possible position that results in less inserted penis works good.
    No rear entry positions unless he can be trusted to limit himself to average depth. To the guy about to get a threesome remember your wife is not a porn star and it may not help your relationship in the long run.
    Gently and loving foreplay is the secret. If the man sits in the Centre of the bed the female can gently slide up his legs in a seated position, easing his penis inside and limiting the depth. Her legs spread on each side of him, a forward and separation of the bodies allows shallow depth and prolonged fulfilling feelings without climax. Allows you both to get acquainted with each other.

  7. We’ll be having our first threesome soon, and the guy (although short in height) has a 9″ cock. My wife has had a 7″ before we married but never a 9. Any suggestions will be appreciated.

  8. I agree with theattack, actually although I don’t like the word “size queen”. I have been seeing my own “mythical man” for several years now so have a few suggestions for “Saddle Sore”. I should give a little background though even if it opens me up (pun intended) to judgement by some like WTF.

    I had a lot of fun in college. The sex was fun, easy and my wild side came out, I guess. For me that included dating black guys. While I’ve read that it’s all a myth, for whatever reason for me it was quite true. They were definitely bigger and I found myself enjoying it a lot. One guy in particular was very well endowed and we got together at least several times a week for over a year. It was wonderful sex.

    We all graduated and moved on but, I totally missed it. I then found my future husband and fell totally in love. Wonderful guy, soul mate, etc with an average 5″ penis which he is pretty good with. Long story short (sorry, pun intended WTF), it turns out my new husband enjoyed fantasies and my past in particular. It turned him on! So, with fear and excitement he gave me permission to seek out the black lover I had been missing and to experiment within our marriage. And that’s what we’ve done. With much communication and honesty it is not only working but, has made our marriage better. Ok, I know some will be judgmental on that like I said.

    So, with the same regularity I had in college, several times a week I meet with my own “mythical man” of color and experience the joy of what I will say to Saddle Sore you “get used to.” The more you do it the easier (and better) it is. So, if you truly enjoyed him as it sounds like you did, with all the advice that they gave you about lube, etc just go slowly until it becomes as natural as with the average-sized men you’ve been with. Be careful though since it does become your “new normal” and you’ll miss him if it doesn’t work out or you don’t find a wonderful, understanding husband like I did.

  9. Keep in mind you’ve only done it *once*. IMX, your body will adapt to some degree after a few more sessions. Lube, patience, and relaxing are key. Hopefully he knows he has a monster and isn’t just banging away on you.

    Wtf: if it makes you feel any better, I’ll probably never get the chance to enjoy anal, and have yet to experience getting deep throated. As much as my gf would love to, it’s just not in the cards. There are trade offs in everything. But the anger you’ve got going on is far more of a deal killer for you than the size of your cock.

  10. tisk,tisk its a shame how many women intentionally try to hurt men with these subjects,it is quite sad.So guess what ladies any woman over 115 lbs is FAT! Dig it?

  11. I’d just like to point out that someone held a survey awhile back and it was decided that henceforth the term to describe breast-penis action shall be known as “melon-balling”.

  12. I had the biggest surprise recently when I got together with a totally average sized guy, 5’10, slim build. Average nose, hands, feet, ears, whatever ‘indicators’ there are supposed to be. He had the biggest cock I have yet come across. Two fists and a mouthful…
    Anyways, to all men who think women are size queens. It all comes to naught if we are not compatible sexually. If we have differing ideas about what makes for great sex.
    I have had average dick sized lovers with great, sexy minds and a willingness to be wild and have fun. Best lovers ever. I have also slept with big dicked guys with poor bedroom skills and I didn’t stick around just because, o yay, a big cock. Not at all.
    Lucky for me, this last guy Mr. Average with the not-so-average schlong was not only the biggest but the best. Why? Because he was sweet and funny and raunchy when it mattered and not afraid of learning me and letting me learn him. That’s the real deal.

  13. Whatever a woman says, the truth is really the opposite.

    A man’s dick size does matter to most women, period. If she says it does not, then she is a liar.

    Yes, some guys can be too big for her, but she will always prefer a bigger one to an average.


  14. Thank you Dannie, Wtf please read better, and not because you ‘seem’ to be small downstairs means you should take such offense to their reply. Let it go, you’ll find a woman that does not mind your size. Someday.

  15. I have posted this here before, but I’ve gone some distance with a Penis Sleeve for this issue.

    Mainly for oral. A little lube, and “Jenny” helps me right along with it, she takes the shaft and I work her up and down while I do the rest. Squeezing, twisting and if I don’t want to, she swallows for me too! We both love that toy!

    For intercourse, not so awesome for him, not used that way very often, Jenny doesn’t move so he just misses all that action for the bottom half of his shaft. But if he want’s to do regular doggie, she’s a must.

    Hope this helps and WTF, easy guy. This so wasn’t posted to freak anyone out. It’s an honest PROBLEM some people learn to work around. No different than a short or wide or super crooked penis, okay? (I think I’d take 2 inches off if I could. I mean that, it would open up more options for us).

  16. Em and Lo you really need to stfu w/this stuff you only throw up these threads to try and bash avg and lesser endowed dudes you women make me f##king SICK! The “Bigger isn’t always better” response and w/that you imply that is usually is so you are pathetic.

  17. I’m a size queen with a well-endowed man as well. I still maintain that bigger is better despite the major adjustments we had to make. 1) Most importantly, start slowly. We call it “opening me up.” If you get in the missionary position and let him make slow, small thrusts into you slowly getting deeper, it helps infinitely and can almost solve your problem. You’ll feel yourself opening up for him after doing this for a few minutes. Girl on top is NOT a good way to start out with a bigger guy. 2) Try not to let him out of you for very long. When we switch positions, we do it as quickly as possible, because I tighten back up after a few seconds of not having him inside me, and then we have to do the “opening” process all over again. 3) Lube. I don’t use any because I naturally produce way more than is necessary for anyone, but if I didn’t have that issue, sex would be incredibly painful without it.

    Also, about the condom thing. What condoms should someone use with a well-endowed man? We’ve never used any together (tested, committed relationship, etc), because we could never find any that would fit him. None of the XL condoms were wide enough. They only get longer, which isn’t helpful when you can’t even get it on in the first place.

  18. “Sleeping doggie” is also a good one. Regular doggie is pretty much the worst position for partners with high penis-length to womb-depth ratios. Sleeping doggie also automatically knocks off a couple inches.

  19. When I’ve been with shallower-wombed women, my trick is to position myself differently. If a woman can take the whole thing, at full insertion, her clit comes in contact with the top base of my dong, where dong and torso meet. But if she can’t take the whole thing, I basically slide down a bit so that her clit is making contact with my body about half-way between the dong-base and my belly button. This allows for missionary clitoral stimulation, while knocking a couple inches off Johnny Junior.

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