Well-Endowed: My Tale of Woe

Pain, humiliation, and compression shorts: Being well-endowed ain’t as pretty as it looks.

I’ve got a big penis. This is my tale of woe.

I lost my virginity to my high school girlfriend, Claire. She had amazing skin and wild blonde hair. She also had a friend, Anna, who had a problem with us dating and made it her mission to harass me. I don’t remember how sex felt that first time, whether I came, or how long it lasted. I do remember being made fun of for the size of my penis a few days later.

Only a teenage girl could turn that revelation into a source of shame and embarrassment. Anna sauntered up to my lunch table where I sat, witless and surrounded by friends. “So, Charlie,” Anna announced to the table, “Claire was just telling us you’ve got a big cock!”

Our culture is built on the notion that bigger is better, and (depending on who your analyst is) the male reproductive organ is the root of it all. There are very few negative stereotypes associated with a sizable schlong. A large cock confers unflappable confidence in life. Sexual prowess is no problem for the well-endowed man; just a glimpse of his tumescence will send women everywhere into orgasmic fits.

Of course, the reality’s very different.


The most immediate problems are anatomical. On a personal level, the circumference of my head while erect slightly exceeds the comfortable limits of my foreskin. That’s most inconvenient when masturbating, as the skin gets pulled up and down on the head to varying degrees. During colder months, when my skin is dryer, I’ve masturbated my way to tiny lacerations around the edge of my foreskin.

During sexytime, I need to be on guard. A misdirected thrust can end congress for the night. Even just easing my entire penis into a vagina has caused the not-sexy kind of pain. I’ve also been told, without any preamble, that anal sex would never be on the menu. It wasn’t a huge blow. But to my hung brothers with posterior proclivities, I sympathize.

Then there are the accessories. If compression shorts cost as little as cotton briefs, I’d be wrapping up tight every day. Bouncy bouncy, fellas! Speaking of wraps, condoms pinch like Houdini’s handcuffs. Sure, normal-sized guys also complain about them, but I’m guessing that putting them on and taking them off isn’t supposed to actually hurt like it does. I also suspect that the pain and constriction contributes to my tendency to … overstay my welcome at times.

So: Magnums. Two hang-ups consistently prevent me from picking them up. A girlfriend suggested them numerous times when I complained about the pinch, but I was afraid Magnums would be too big—and that she’d be disappointed and/or turned off to find that her man wasn’t as big as she thought.

The second reason is that I simply do not want to be That Guy.


That Guy is my biggest problem with my biggest digit. All of those wonderful huge-dick stereotypes don’t apply unless everyone knows your big secret—and that’s just not going to happen. There is no casual way to spread the word that you’ve got a plus-size penis. Any attempt to disseminate information regarding your Richard will—nay, must—be met with skepticism, pity, and annoyance. At best people will assume you’re lying; at worst they’ll believe you and think you’re bragging. You look like a tool either way.

So, of course, I’m constantly tempted to be naked at inappropriate moments. I’ll convince myself that whipping it out is the end-all-be-all answer to certain problems. When my self-esteem takes a hit, it hides between my legs. Get turned down for coffee? If only she’d known about the stir-stick. How impressive is that guy’s six-pack? I bet he’s only got a six-inch.

Denying my atavistic urges creates a lot of stress. Even if someone finds out in the most ideal way—having sex with me—I get weirded out if she says anything about my cock outside of coitus. At my craziest, I fear that hearing it too many times will subconsciously turn me into a man content to let his fairer attributes wither away, left with the unearned sense of entitlement a titanic trouser trunk bestows.

In my day-to-day, I get by pretty well. I take time to get to know my partners inside and out before going Dirk Diggler on them. My underpants are supportive and affordable. I’ve learned to limit my onanism. I have even learned to accept compliments gracefully.

Looking at it this way I can appreciate how my penis has helped me. I’m more self-aware than I’d be if I’d been graced with an average member. In all honesty, I don’t hate my big penis. I just hate what having a big penis means to everyone else.

(Photo via K0P)


More from Sex Week at the Good Men Project:

Amanda Marcotte: What Women Don’t Tell You

Ed Fell: 10 Secrets to Satisfying Sex

Emily Heist Moss: Does Size Matter?

John DeVore: Multiple Inches of Love

Joshua Matacotta: Do Gay Men Fear Intimacy?

Hugo Schwyzer: Mythbusting Bisexual Men


  1. Sandra Kelly says:

    For me I don’t really enjoy a larger penis. I will say it’s nice to look at but when it comes to getting down to business give me mr. average who knows how to use it. There area couple things I found with my boyfriends who had bigger penises. They tended to think their size made up for a lack of trying to please me, as if just being penetrated by their large member should be enough. They also tended to be less willing to perform cunnilingus. I am not saying this is the case with every well hung male, just my experience with them. The average men all seemed to think they had to go above and beyond to prove themselves in bed. So maybe this whole large penis thing really works out for us women in the end.
    I did recently read a article about this that is worth a read for you men out there who think you have less to offer due to an average or below average penis.

  2. THIS COLUM IS TOTALLY BOGUS!! In fact , I think it was actually written by a woman pretending to be a man. Look, my best friend in my late teens and early twenties was “Hung”. In high school he had more girls wanting to “check him out” (a couple of teachers too!). When we graduated school and went out into the world, it got even crazier for him. While the rest of us tried every gimmick that was” Gaurented to get you girls”, he’d “hook up” with one, she’d tell all her friends,and the next thing you know, he”d have all these women stalking him. Not that it did the rest of us any good (they didn’t want a ride in a Honda, they wanted to ride the “stretch limo”). I guess you could say the only “curse of his endowment” is that with all these women chasing him, he really couldn’ be faithful to his girl. Although, she did keep forgiving him and taking him back. I mean after all, how was she going to replace that cannon.

  3. MrBiggerThanBig says:

    I can understand some of what this guys is saying. I too am well hung. In high school it was a bit of an embarrassment. Only because I was hard all the time! I remember guys on the swim team would stare at my wiener when I was dressing and that was embarrassing. However, no one said anything out loud. Plus, I was too afraid to check out their package so I did not even know how well hung I was. I also caught a student teacher staring at my bone while I was taking a test.

    Bottom line though…there isn’t a guy on the planet that doesn’t want an even bigger dick. So his BS about not wanting to try on a Magnum…come on. That was the first thing I did, hoping it would be tight…and it was.

    I hear all the time: “oh, I couldn’t possibly take you.” With enough oral stimulation everyone is willing to give it a shot and I have never had anyone make me stop because I was too big. You just have to go slow and make sure they are enjoying themselves. You also never slam a huge cock into someone unless you like damaging them internally.

    The only downside to being really well endowed is that often it feels like the only thing anyone wants you for is your cock. The question I had to ask myself was if it was my fault. At first my size was the most important thing. As I grew older I learned to really get to know someone before dipping my wick. It doesn’t mean that the first few dates were not because of the stories of how hung I am. However, I have learned that once I get to know someone, often times I do not want to sleep with them.

    It’s the male version of the girl with big tits.

  4. @MrBiggerThanBig said: “It’s the male version of the girl with big tits.”
    Yep, yours is the best comment so far. 😀
    Most men love big tits, and most women would like having them… but that doesn’t mean that having huge boobs comes without issues.
    I’m well endowed as well, and I’m grateful! 😀
    It has never got me any more girlfriends (as Charlie said, how could you “spread the gospel”? 😉 ), though, and sometimes it’s a limit (anal, no letting go and thrust wildly…).
    But I’m not complaining, honest. :-)

  5. I can’t believe they recycled this BOGUS colum with a new title. What is this supposed to make all us “average/normal” sized guys feel better about ourselves? You just don’t get it. It’s not the fact that we’re not the “biggest” guy on the block that bothers us. It’s all the double talk and outright lies that do it. To all you women with “average/normal” size guys I purpose a hypotheticial event. Let’s say that a cosmic event occurs and it causes all “average/normal” size men(oh hell, let’s include some below”normal average size guys too) to gain 1-2″ in length and lets say 25% or so in girth. Now, all you women that would be upset and angered by this event, please raise your hands. Anyone? Anyone at all? Somehow I didn’t think so.

    • Haha. Yes, I would be, actually. At the moment, my husband can go wild and it hurts in the good way. It hurts, but it isn’t incredibly painful. If he added another inch or two it would go to the point of not being pleasurable pain anymore. I’d choose 5.5″ over 7″ any day. But that’s just me.

  6. hey

    i actually kinda stumbled upon this site. i’m glad i did though. I really like the content here, and i will also bookmark it and add your RSS feed so i can keep in touch.

    thanks, Eric

  7. Size matters!! I need a big one that fills me up!!!

  8. You guys are whiny. You should give them to more deserving girls!

  9. Heinz Scheiße says:

    Mein ding dong ist only 8 cm but she loves to me when I poop der big 24 cm on her tits. Das ist doch alles Scheiße!

  10. If you want to see the final word on this, goggle “Womens Preferred Penis Size Chart”. Guys, just a warning, you might be bummed out

  11. I haven’t read through all of the comments here and if I’m the first to break it to you, I’m sorry, Charles, but if you can wear regular condoms, you don’t have a very large penis. It sounds like you’re probably a little longer and thicker than average. I know what it’s like to be the guy who buys Magnums. I’m the guy who has to buy Magnum XLs because the extra 1/8th (I believe that’s how much wider they are than regular Magnums) makes a real difference to me. Even the Magnum XLs are too constricting.

    While anal sex is usually off the table for me (not really my thing anyway), I’ve never had size be a huge issue when it comes to sex. I’ve also never had sex with a woman who I haven’t cause some amount of discomfort, and there’s usually some mix of discomfort and pain. This tends to go away if you’re in a relationship and having sex regularly.

  12. Everyone has different preferences. For most of my life, I had issues with painful sex, especially “doggie style”, because of my retroflex uterus (Google it). My current partner has a smallish-average penis (about 5.5 inches erect) and sex doesn’t hurt at all! In fact, doggie style is now one of my favorite positions. so, this just proves there is someone for everyone.

    • Jun Kafiotties says:

      5.5inchs isn’t smallish, that’s normal/average. Even 5 inchs is not small, porn has warped the views of many.

  13. The Bad Man says:

    I never encountered any foreskin problems but I’m kinda glad that I’m not circumcised. I don’t understand the dry skin thing, don’t you use lube?

    Doggy style is risky for going too deep, anal has never been an option or an interest. I had a short term GF in college that was a bit too tight and we had a hard time having enjoyable sex. A few years later I read the kama sutra and understood that some men and women aren’t made for each other. Many of my GFs have commented about big hands and feet being characteristic of a big member. They already know, you don’t have to tell them. If you want to tease them, wear tight jeans.

    Magnums are awesome, regular condoms are too restrictive and they’re hard to put on. Just buy them and smile at the clerk, it’s no big deal.

    I’ll wear boxers or briefs for support depending on my mood. Sometimes the boys get sore or it falls down one leg in tight jeans, it’s manageable.

    “I just hate what having a big penis means to everyone else.”…exactly!

  14. So. In the imortal words of Detective Bunk: “I’m just a humble brother with a big swingin’ dick”…?

  15. Are You Serious? says:

    Seriously dude? And yer crying about this? I’m sorry but I’d love to have your problem.

  16. I have a 1 and a half inch penis. While erect. I feel so sorry for you with your problem. I shed a tear while reading your post. Must be tough.

  17. Buy the magnums. That’s what they’re made for. There is NO good reason for you to be uncomfortable while using a condom. Sex is supposed to bring pleasure to both of the people involved.

    Take a deep breath, pick up the package of magnums, and go thru the line thinking matter-of-fact. THis is the size you wear. You’re not the only guy who needs them. Other guys genuinely need them too. You are not bragging or showing off, you’re buying something you need. It really is that simple – not easy perhaps, but simple.

  18. John Sheperd says:

    look dude….., Im 24 now and just graduated from college. I have always been big downstairs. I never had to worry about anything in bed. Just get the magnums for christ sake. I played sports in high school and when we went to take the showers after practice, it was nice having the biggest penis in the lockeroom. The girls always asked the boys if it was really as big as it was and they told them so I lost my virginity when I was 13. It gets people curious and then you wont ever have to worry about keeping a girl in your bed. And if they dont like it, then slap them upside the face with it lol

  19. I understand what you are saying about being extremely well endowed, but it is not a curse. Go ahead and buy the “Magnum” sized rubbers, that is why they make them. If only a few guys had big cocks they (the companies that make them) would not be spending the money that it takes to market them. I can’t get a regular sized condom on mine and was glad when they started marketing the bigger ones.I do get a chuckle out of the expression on the face of a sweet young checkout girl when she looks at them and turns a bit red in the face. When that happens, you know that she is wondering how it would feel to try a really big one.While it is true that every woman does not like a larger one, most of them want to try one at least once and many to of them, bigger is better.

  20. I would actually be more impressed by your casual use of the word “onanism.” Impressive…vocabulary.

    • Screw you dude... says:

      Waaa waaa waaa…Women are coming forward these days with their preference for the larger sized man (even if only occasionally). I’m sick of hearing you blessed guys whining about how having a large wang isn’t all it’s cracked up to be. When you’re the guy who is with the girl who has had men larger than you and admits that big is good now and then, then complain. When the thought that you can never satisfy her like those larger men constantly pervades your thoughts, then complain. When you feel like less than a man because you are the perpetual “joke”, the non-well-endowed Black man, then complain.
      Until then, STFU about how your large penis causes YOU problems when in fact, your large schlong causes ME problems.
      (P.S. props on the “onanism” usage though LOL)

  21. The comments are so unsympathetic…

  22. You’re just fishing for sympathy. I would KILL for what you have, just because of the confidence and the fact that I know that I could please a woman. That is if I could get one without them judging the size of my member!!!!!!!!!!!!!!!!!!!!!!!

  23. I read this article because i am one of the women that do not look at over 7 inches being a good thing. i can offer some tips. First use lube! by yourself and with a partner. esp since it is causing foreskin pain for you. also look up condom sizing charts online. PLEASE! using a condom that does not fit properly, whether too big or too small, can significantly decrease its effectiveness.

    obviously choose positions carefully and try out some positioning pillows. If full penetration is out of the question with someone you can actually use a penis sleeve to make sure that you do not go all the way in.
    so please…lube and proper fitting condoms.

  24. Lol a big dick complaining no one cares man we feel so sorry for your big dick problem it’s such a problem what you have is a gift not a curse stop crying and use what was given to you there’s millions who would kill to have one never I actually thought I would hear a man complain about that it’s quite funny me and my girl can’t stop laughing at your problem the rest of us enjoy it you think it’s kinda bad cheer up like I said it’s a gift you should think that too

  25. Very descriptive blog, I loved thaat bit. Willl there be a part 2?

  26. Spot on with this write-up, I really think this amazing
    site needs much more attention. I’ll probably be back again to
    read more, thanks for the advice!


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