Wise Guys – What Are Men’s Biggest Insecurities During Sex?

photo by Ecnerwal

Advice from three of our guy friends. This week they answer the following: What are guys’ biggest insecurities during sex?

Straight Committed Guy (Johnny): I think many guys are afraid of their own inexperience early on in their sex lives, or later on too if they don’t get laid as much as they’d like. This insecurity is exponentially magnified if the man’s lady partner is more experienced than he is, which can trigger the following:

  1. Comparison-Based Anxiety – “How can I possibly stack up against a slew of guys who had the game to get my girl in bed quicker than I could?”
  2. Irrational Resentment – “Why couldn’t she anticipate that I, Mr. Special-and-Different-from-the-Rest, would come along and be jealous of her numerous partners?”
  3. Madonna/Whore Complex – “I’M the man, I’M supposed to be the hornier and more promiscuous one! YOU’RE supposed to be a prim, chaste little lady! What the hell!?”
  4. And of course, The Size Issue (sorry to bring this up AGAIN) – “Is my dick big enough? Bigger than her last partners? What if it’s the smallest she’s ever seen!?”

In my opinion, these fears based on lack of experience (which at their most powerful can induce impotence) come from the widely held misconception that women see sex as dirty and gross, and that we guys have to be extra careful when broaching the subject, lest we be slapped with some kind of lawsuit. Thanks a lot for kicking THAT off, Clarence Thomas.

chris_diclericoStraight Single Guy (Chris): You might guess it’s penis size, but I think you’d be wrong. I can’t speak for everyone, but it seems to me that guys are much more preoccupied with stamina than size. Based on jokes I’ve heard women telling each other, it may also be a legitimate concern. I have no idea how long “long enough” is (duration, not size), but I would guess that longer is always better.

Gay Single Guy (Angelo Nikolopoulos): In junior high, I had what pubescent boys commonly refer to as bitch tits. It goes without saying that when summer reared its cheerful face into my cruel childhood, I was that unfortunate-looking child wading in the swimming pool with an oversized t-shirt on. Apart from the inherent difficulties in treading water in an oversized Billabong shirt, what tormented me more than bathing fully clothed—in stark contrast to my peers’ taut and sparklingly bare bodies—was finding a way to conspicuously dive in without causing alarm. Finding an exit strategy from the pool was similarly fraught with anxiety, as my sopping t-shirt had the unflattering effect of sticking to all my unsightly wobbly parts. However, once I managed to cannonball in, I was as happy and carefree as an otter.

This is a strange metaphor, I admit, in response to what a guy’s biggest sexual insecurities might be, but I’m willing to conclude that a straight man is as blissfully engrossed during sex as I was stupidly happy as a chubby thirteen year old floating about in the neighborhood community pool. Though the moments preceding and succeeding sex might be laden with anxiety (i.e., insecurities about penis size, female orgasm), I’d venture to guess that when a man’s hip-deep into a woman, it’s all tulips and sunshine and such (bitch tits or not).

Our “wise guys” are a rotating group of contributors, some of whom wish to remain anonymous and some of whom like the attention. This week’s Gay Guy is Angelo Nikolopoulos, host of an NYC queer reading series The White Swallow; Straight Single Guy is blogger Chris DiClerico; and our Straight Committed Guy is regular EMandLO.com commenter, Johnny. To ask the guys your own question, click here.


  1. Jay has written stuff in his piece that adds to mens securities,”some say its too big!”, everything these days seems to emphasise the bigger penis size,I believe God was a joker and instead of making man equal he made them so unequal that in a lot of cases a woman loves her man but loves anothers sexual actions.
    I know that the sex with a bad partner when its great sex! will win over a great partner and love in almost all cases,women will disagree of course they will,it makes them look a little cheap you see,I have an average size but i have lost women to guys who I assume are better on bed or have bigger penises,I have talked to my girl and she admitted she thought the other guy was a slob and treated her like an animal but she could not leave him.she loved me but loved his sex more,that cant be right! can it!

  2. I agree that longer isnt always better. Im a guy who sometimes doesnt cum and i take a while when i do. A lot depends on the woman. Some women love that i can go for hours, while some are happier with 20 or 30 minutes of intercourse. Same with foreplay ive found. My insecurity is definitely size. Im not small by any means but im not impressively large either (maybe about 7 inches but i didnt actually measure) and i think its avg width too. Ive had women (not many) who i could kinda tell were used to big diks and i simply couldnt satisfy them. Ive also had some who commented that they didnt think it was going to be as good as it was and seemed very satisfied. Ive had a few say i was a little too big for them. Its all just a matter of taste i guess.

  3. Absolutely agree with jenojeno and ToppHogg. Some of my worst sexual experiences have been of the montonous-rutting-for-what-seems-like-hours variety. It’s just uncomfortable in the end.

    For perspective, the best sex I’ve ever had was with a guy who was more or less unable to come from sex alone. Instead of just going and going at the sex, we just knew when enough felt like enough. No pressure on duration. More time spent on other things which was very, very satisfying.

  4. I have to pick up where Charlie left off. Foreplay is really where the action is with the women I’ve been with. Seeing to it that she has an orgasm before penetration tends to make penetration itself easier. Duration – despite the jokes that Straight Single Guy mentions- really isn’t what my partners seem to want, for they complain about soreness when we do go longer. It almost seems like they want to get off, get me off, and spend much more time cuddling.

  5. I would say that some of my biggest insecurities as a male are what to do during missionary style sex. Do you kiss, do you make eye contact, do you rub, etc? I find spooning and all other kinds of sex easier to manage expectations with.

    As for the longevity, I have never lasted long in the final act of the sex play. My partners have always commented on good foreplay manners. Start with the kissing, undress each other, do some massage or body kissing, move onto oral, and then before you know it by the time you get to penetration all parties are pretty happy about their position in the sex world so far.

  6. “I have no idea how long “long enough” is (duration, not size), but I would guess that longer is always better.”

    Longer isn’t always better — too long and you get chafing, boredom and diminished sensation. Common misconception among guys, and sort of tragic, with them working away to get to some magical number or minutes. Women get to “are you done yet” faster than many men believe.

  7. Interesting answers and, for Angelo, cool metaphor. But even as a straight female, I’d have been curious to know what his insecurities are during actual sex rather than what he thinks they are in a guy who is into women. But perhaps it’s hard to put them out here, which I can understand. But if not, why think straight? We’ve all been thinking straight for way too long and could do with other views.

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