When Does Size Matter?

Size Matters When You’re Hung like Donkey Kong

Not surprisingly, the most popular dating advice video I have on WingmamTV is about penis size and does size matter. Most guys want to know if their dick is big enough. But what happens when your dick is too big?

Wait, Anna, did you just suggest that there’s such a thing as too big?

Yes, Hun. Yes, I did.

I got an inquiry from a guy who’s hung like a large circus animal. Though it may sound silly to most of you reading this, for him it’s serious and seriously affecting his love life.

First of all, when you wonder does size matter, you’re probably either a guy with a small penis or an average-sized penis. So, your primary concern is whether or not you can please a woman with what you’ve got. Right?

Well, imagine if you’ve got an appendage that can’t please a woman — at least physically — because it simply won’t fit. Just stop and think about that for a minute.

So, for example, you’ve got a small dick, but it fits in most any vagina. Great. Learn how to use it and get good at going down on chicks. Here’s an amazing article on eating pussy that’s AJ-approved!

The good news: she feels your penis and you feel her va-jay-jay.

If your phalange (that being your dick) is too big, get good at eating pussy. But the bad news is that she’ll never feel your penis inside her and neither will you, because it just doesn’t fit.

That sucks. (And on that note, she probably can’t give you a proper blow job either, so you’ll have to be okay with her going down on you like an ice cream cone.)

When Does Size Matter? A True Story

This is the actual email I received from a man with a big problem and my reply therein. I edited out a few bits irrelevant to you, my reader. (Published with permission.)

Donkey Kong: To be quite blunt. As far as the issue goes with my size, I have had issues, since I was in high school, finding women who can accommodate my size. Fitting [in the woman] is a significant issue at the beginning of every sexual encounter I have had. To the extent that it takes more sessions than you’d think to fit.

I’ve done research on the topic, so I get my partner ready and in the mood to pursue to the next steps if I fit.

Most of the women I have been with have had trouble adapting to my size during intercourse. I have been in multiple relationships where they truly never adapt to it.

In the end, the situation truly affects not only the lack of pleasure on my end (which over time becomes very much of a pain in the ass), but tends to draw an issue and gap between my partner and I emotionally.


AJ: Totally understandable. Sexual intercourse is the one of the most intimate acts we can share with a partner, so when we can’t share that experience in a way that is pleasurable to both partners, it stands to reason that we start to pull away emotionally.

So, does size matter? Yes, though the situation isn’t insurmountable, unlike your large appendage, but it can definitely affect the closeness of a relationship, especially if you’re under the age of 50 before testosterone — the sex drive hormone — noticeably decreases.

When testosterone decreases in men, oxytocin —the bonding hormone — becomes more pronounced in men’s feelings and behaviours. In other words, they’re less horny and more lovey-dovey cuddly.

Men under the age of 50 who also experience lower testosterone (for whatever reason) might also be okay with the ice cream cone BJ and a cuddle session, because a lick and a promise of sexless intimacy is more appealing to men with lower testosterone than in men with high testosterone.

What to do When You Have a Huge Cock

DK: I’m not sure if I view this topic as shallow, but I’ve tried many times to work with what I know — be sure I please the woman and learn to work with alternative methods — but it feels like problems start with my penis size.

In the end, we drift and then things end. This has been an issue I have dealt with off and on even into adult hood. I’m not sure what to do anymore.

I would like to have a satisfying sexual relationship, but also an emotionally satisfying one as well. I’ve pondered informing my partners early on about some of the issues (penis size) I’ve had with partners, but it’s hard to gauge when to bring up such a topic, which has me pretty guarded about the issue.

AJ: We (society) joke about being hung like a tree trunk because society tells us bigger is better. Even young boys in locker rooms razz each other about their dicks. And of course, porn sites need an audience so anything unusual, such as a big penis, gets viewers.

It’s no wonder men are obsessed with their Johnsons their whole lives. And it’s no wonder that we think having a penis that’s too big couldn’t possibly be an issue and keeping Googling “does size matter”.

When to Talk About Penis Size

AJ: This topic is something guys with particularly small dicks also think about. It’s a relevant concern. You don’t want to wait too long and get overly invested if the size of your penis is going to be a deal breaker for either of you.

If you’re simply looking for sex this is the wrong website for you, go to and put your penis size in your profile, Hun. But if you’re looking for a committed, long-term love, well then, when to talk about the size of your penis is a rather sensitive issue.

My advice would be to definitely discuss it before you whip out your big (or tiny) surprise in the bedroom. In other words, this convo must happen before you get naked together. 

If you’re looking for a serious, long-term, monogamous relationship, in most cases you’ll find that you’ll be getting to know the girl at least a little bit before you bump nasties.

Of course, occasionally there’s magic chemistry and the stars align, and she’ll want to jump your bone right away, but usually not. If she does, well, warn her first, anyway. At least you’ll find out pretty quick if what you’ve got between your legs will work with what she’s got betwixt hers.

Otherwise, tell her on Date Number 3. Yep, that soon. On a second date, she might still be deciding if you’re “a potential possible.” In other words, she might not be mentally walking down the aisle with you, but by Date 3, it’ll be pretty clear that she likes your company.

How to Bring Up Penis Size

AJ: The best way to bring up the conversation about the size of your penis is to forewarn her just before your third get-together. So, an hour or so before you meet, send her a text that says something like this:

There’s something I need to talk to you about, but I don’t want to freak you out. I’m not diseased or dying or anything, but it’s kinda serious to me. Can we talk about it today when I see you?

Now, be prepared because when she gets that text, she’s going to freak out. That’s what women do. She’ll either reply demanding an answer or maybe call you immediately. Because of biology —  we’re wired differently than guys —chicks are emotional, irrational creatures, so just be prepared for that.

If she freaks out by text, call her. Yep, call her immediately and just soothe her with the soft tone of your voice as though you were talking to your way younger sister (imagine how that would be if you don’t have a younger sister).

Say, “We’re going to see each other soon. I’d like to talk about it in person.”

If she persists, which she might, then you have the green light to tell her over the phone, “Look, I’ve got an unusually big penis, and it’s been an issue in the past. Can we please talk about it in person?”

What She’s Thinking …

Guaranteed she’s going to feel better because, in the three seconds after receiving your first text, she assumed you are (in order of least to greatest disaster):

  • are a criminal wanted by the law
  • are married with children
  • have an STD
  • going to dump her

Oh, you think I’m joking? (Insert: raucous laughter!)

If You’re Hung Like a Porn Star Should You Go into Porn? (Or Swinging.)

DK: After a discussion with a fellow friend, I’ve come away thinking about getting into the swinging lifestyle. Not that I have tried it, but I’ve been informed that I may be somewhat of a hit in the community. But morally, I’m not so sure that is something I could see myself attempting to do.

AJ: The answer to this question is as easy as all those swinging ladies who want to get a look at your schlong. Never do anything that doesn’t align with your values.

Physical Issues with Problematic Penis Size

DK: I also have an issue when I am erect that led to me becoming light headed and passing out when things were very heated in the moment. This is something that I can say has also caused some issues sexually, but not as much as you’d think. I’ve recently gone to the urologist and am seeing a specialist about the cause.

AJ: Yep, if you pass out on a girl when you’re mid-action in a girl, that’s no good. Seeing a specialist is all you can do. I’m leaving this question in here so all the guys with smaller peckers will realize just how much trouble a big dick can be.

DK: Relationships have become stagnant for me. I’ve found it tough to get past a certain point lately. I’ve dated and am pretty confident, but what I am afraid of is the potential of things failing once I’ve become involved with someone.

For it to just flutter away because of an issue most would typically think is a blessing but is far from the truth of being one. I hope none of this seems silly … but it has truly affected my life.

In Conclusion …

AJ: As I mentioned in my email: “Hang in there!” But all joking aside, I hope that this post has provided some answers to your questions and that it has helped any other guys out there with issues who want to know how to address them early on.

Incidentally, I know another guy with a very large penis. I didn’t date him because of it. I couldn’t. But I have dated guys — almost married one of ‘em — with smaller-than-average penises. So, for a guy with a huge penis, the struggle is real, fellas.

Maybe it’s time to get your head around that. 😉


What do you think … does size matter to you?

Anna Jorgensen

About the author

Vancouver dating coach for men who love women! ❤️
(Not PC and not a feminist.)

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  1. awesome article! I too hear from a lot of men who don’t realize that being larger than average can have many drawbacks as being smaller than average. I liked your point about eating pussy, I usually also tell men with smaller penises that they’re more anal friendly and should explore anal sex with interested partners! – Caitlin

    1. Thank you for commenting! Men need confirmation from women that bigger isn’t always better!! And, as you mention, there could be potential other benefits of smaller (for those who are more adventurous lol)

  2. I came across your lessons on dating, and wanted to tell you how amazing your videos are that you post.
    I am a 72 year old divorced male living alone and not dating anyone. I really would appreciate a very sweet Lady to spend quality time with and enjoy their company. I did talk to one very nice lady on a dating website, but all of a sudden, she went ghost on me. I have not been able to get in touch with her again. So I sit here.
    Any suggestions for me???

    1. Hi Ray, thanks so much for watching my channel! I answer short questions on my newest video published on Tuesdays at 3pm PST for an hour, where others may benefit from my answer. (Few see these comments.) Please post your question there this Tuesday. Advice for today: Go out and play! 🙂

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