If He Asks About Size, Can I Tell Him the Truth?

Advice from three of our guy friends. This week they answer the following: If a guy asks me how I think his penis ranks size-wise, and I honestly think it’s a little on the small side or perhaps too skinny, what do you think the best approach is?

Straight Married Guy (Fred): I’ll start answering this question with another question:  If I honestly think a woman is on the big side or perhaps a little chubby and she asks me if she’s fat, what do you think the best approach is? Of course I tell her that she looks great. But there’s a difference between these two situations: she can eat a healthier diet and exercise but he can’t do anything about his size. She may even be looking for a little motivation with the question, but it’s still polite to fib in this instance. Which means it’s imperative to fib in the other instance. Tell him that you think his size is great. You can add that you’ve seen bigger and, more importantly, you’ve seen smaller, and that he’s just right.  Adding that too big can be uncomfortable is always a good tidbit as well.  Being honest in this case will only serve to make him forever self-conscious or even more self-conscious than he already is (men hear all the time that “It’s not the size of the boat but the motion of the ocean,” but men also see the widening eyes and devilish smiles when women talk about sizable, girthy man-sausage). A finessed answer can give him the confidence that most women find attractive and will more than make up for his tiny dick.

Straight Single Guy (Chris): This is an easy one: Lie. If you tell the truth (“It’s kind of too skinny…”) his penis may never again work for you, ever. Put yourself in his shoes, “Are my boobs big enough for you? You seem to always look at girls with big boobs when they walk by…” Would you really want him to say “Well, honey, your boobs are cute, but they are much smaller than I prefer. If I could use magic to change you, I would give you natural 34DD’s.” So lie. But before you do, you need to know is that if his penis is small-ish, he already knows. He is already sensitive about it, and he is just hoping you haven’t been with any well-endowed men. So if you overcompensate with an outright fabrication such as, “It’s huge. It’s the biggest one I’ve ever seen,” he will know you are lying to spare his feelings and he will feel even worse. So just say, “Honestly, it’s not the biggest one I’ve ever seen, but it works great for me and you are fantastic in bed. Let’s do it right now!” Trust me, this is the only answer that can work.

Gay Married Guy (Jon Ross): Oooh. Awkward. You might just want to end the relationship right then and there rather than suffer through such an uncomfortable conversation, especially if you can’t bluff. It is never advisable to tell a man his tool is anything but a first-rate, thick cut orgasm factory. If a man is asking you if you think he’s small, he’s probably having some self confidence issues, and confirming his suspicions will only exacerbate problems. So if you don’t mind living with his teeny-tiny skinny-minny member, lie through your teeth. Nothing good can come of you admitting you think he’s small. If the size of his prize has been an issue for you, or you’ve been looking for an excuse to break it off anyway, you might want to begin with “It’s not your small penis, it’s me. . .”

Our “guys” are a rotating group of contributors, some of whom wish to remain anonymous and some of whom like the attention. This week’s Straight Single Guy is Chris DiClerico, and our Gay Married Guy is Jon Ross. To ask the guys your own question, click here.


  1. Be straight up. My ex had ten partners when I met her I was number 8 on the size chart (1 being her biggest). But I wasn’t bothered as I could make her cum from going down on her in minutes and after that conversation we come to realise she could orgasm through deep penetration which led us to getting a 9 inch realistic dildo and we introduced that into the bedroom and to see how it made her orgasm was amazing.

  2. When a guy asks this question, there’s a lot of reasons for asking.

    1. He might want to compete against other guys (“Am I better than other guys?”)
    This is him seeking a straight up ego-booster. Here, he is wanting to feel more manly. If your man is seeking this, you might need to pad the truth a little for him to receive this.

    2. He might need validation on his manliness (“Is my size attractive enough for you?”)
    This is him seeking comfort for his insecurity. He wants to know if he is desirable. He wants to feel sexy. Here the truth may hurt a little but if you speak the truth with love and address the deeper issue, he’ll feel a lot better. Sizing is not the only thing that can make him sexy. You may want the approach to give him the bad news, but telling him how he may be able to be sexy for you. This could be how he plays with your body in foreplay, or the way he looks into your eyes etc.

    3. He might want your judgement on it’s efficacy (“Can my tool satisfy you?”)
    This is him wanting to know how to please you. Size is an easy way to verbally summarise his performance to get you there. But we all know that there are so many variables to getting you to come. It could be the speed, the skin to skin contact, the sounds, your mood, how much you trust him, his attention to certain body parts etc. Here I would still be honest. But again, don’t leave it at a it’s too small/skinny/etc. Tell him why it’s important. It could be that you would like the depth of penetration or the stretch that it makes. This gives him more things to go on and helps him understand what you actually like.

  3. Even if you have an average to plus size penis, most women will have experienced a guy with an extra large cock, (7 to 9 inches). If she cares about you and is smart she will tell you that she loves your junk. Many women have told me that guys with extra large dicks don’t try hard enough to satisfy. They must think that all they have to do is show up for the party. If you treat her like the beautiful prize she is then she will treasure your junk whether it’s small or large. Just be a real man and be romantic!

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