A
female
age
51-59,
anonymous
writes:My husband of 2 yrs asked me who I'd slept with in the past had the biggest penis. Now, I know he's not insecure cause he's well endowed himself. My response was to laugh and asked him why the hell he wanted to know! he said he was just curious. He's not pervy in any way, therefore I was shocked. I guess I wouldn't want to know about his sexual past, therefore, I was disappointed that he asked. I'm a little insecure when talking about past sexual experiences so is that why I'm disappointed at his question? is there anything wrong with him asking this? Weird or not?
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male
reader, anonymous, writes (21 October 2009): As a man, the only way I would ever ask that question is if I was packing a five dollar footlong in my shorts. For him to have the courage to ask that question he is doing one of two things:
1 - he really thinks he's huge and likes to hear it
or
2 - he wants you to lie to him (as most men would expect that in that situation) because it turns him on to hear things like that in bed.
My girlfriend didn't realize the fragile male ego thing and in the midst of telling me that I was the perfect size for her managed to tell me about a past partner that was "freakishly huge". I know that she was making the point that she has had big and small and because of this she can say that mine is just right for her, but I think about her getting railed by this monster almost daily.
A
male
reader, jc2008 +, writes (28 September 2009):
This is funny. I'd tell him "well dear, its not the size of the boat but the motion of the ocean that matters!" Why do you want to talk about our sexual past and look back at things that didn't get us anywhere. Just tell him hes the biggest (which sounds like he is) and remind him that size can sometimes hurt!
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A
male
reader, Illithid  +, writes (28 September 2009):
 k_c100 is right, sadly. We men are still cavemen at heart, and that need to be the best affects most of what we do. Either we want to be the biggest or best in bed, or the strongest guy on the beach, or the richest guy in the boardroom, or the smartest guy in class, or we feel like failures. But in body image in particular, we all hear about women discussing men, or comparing. I myself once found an old girlfriend's blog where she was publicly describing how long and wide I am compared to two other boyfriends of hers (seriously).
The cliché is that women think their butts are too big, or pad their bras (or even get surgery to enlarge them), or get botox for wrinkles, or wear three coats of makeup, then still think they aren't attractive enough, even though most men I know are perfectly happy with a full A-cup or bigger and no need for huge melons. Men want to have a big package, because women are notoriously hard to bring to orgasm (through penetration anyway) and every man wants to feel like he's good enough to make her happy. Knowing that some other guy was bigger makes the man wonder "When she's with me, is she thinking about him?"
Men are insecure, but really, aren't women insecure too? Both of my last two girlfriends asked me if they were tight enough / as tight as other girls. They both needed streams of compliments on their attractiveness, both clothed and naked. The most recent even wanted to know my opinion on whether her breasts were firm enough.
I think that basically, while naked, all people on some level feel vulnerable and want to know they're good enough.
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A
male
reader, CaringGuy +, writes (28 September 2009):
When it comes to his penis, a man has the most fragile ego in the world. You girls think you worry?!!? He's normal all right. Probably just looking for some reassurance.
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A
female
reader, k_c100 +, writes (28 September 2009):
 There isnt anything wrong with him asking this - it is a typical male sort of thing to say! Take my boyfriend for example, he actually said the following whilst he was still inside me after having sex "Am I the biggest you have ever had?"!
I was so shocked he asked, and also shocked at the complete innapropriateness of the moment! Basically men base a lot of their self esteem on the size of their penis and their ability in bed - you must have heard of the "fragile male ego". Men love to feel superior to any of your previous sexual partners, it gives their ego the biggest boost possible! All men are like this - I imagine it stems from prehistoric times where the caveman had to be the strongest and most masculine in order to attract a mate. When thinking about men - most of their behaviour can be explained by these prehistoric principles and yes, it is stupid as you would have thought modern man would have evolved past such things but no, they are still cavemen at heart!
The irony when my boyfriend asked that question was in fact no he is in no way the biggest, but when I laughed and said "what sort of question is that" he replied with "well I am pretty big arent I?" (more stifling of laughter follows). He is a decent size and he is great in bed, but at the end of the day I have had bigger on a couple of occasions.
But the worst thing to do in this case would be to be honest - if he ever asks you questions about past sexual partners or the size of his penis or his ability in bed there is only one answer - you are the biggest I've ever had and the best in bed I've ever had, no-one makes me orgasm like you. Yes it might be a lie but as long as he is actually good in bed and satisfies you then there is no need to make him insecure about his penis/ability in bed.
Just remember - men are fragile creatures when it comes to sex and their bodies, just like we are. They have slightly prehistoric brains where they think "man must please woman and be bigger & better than other man". It is silly and unjustified but that is just the bizarre way men work I'm afraid!
I hope this helps!
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A
reader, anonymous, writes (28 September 2009): sweetie its a guy thing. They all want to know, he just got brave enough to ask. Beats me why, but it is what they obsess about. I have a husband and 4 sons...and i'd bet money they've all measured...and they compare among themselves, and every one they are around much at all. (and i hear them and know too even tho i would rather not) my husband doesnt but says it was just like that when he was in high school. (30 years ago) i dont get it either, and the only answer they are happy with is "wow, sweetie, you are by far the biggest!" we tell them on here every week that size doesnt matter. (unless its an extreme either way) But it does. To the guy. Hope this helps.
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A
male
reader, Illithid +, writes (28 September 2009):
Men are paranoid creatures, even the ones that are well endowed. He likely was fishing for a compliment (even though women aren't so obsessed with penis size as men are) and wanted to know how he compared, or who was the previously best lover. In his mind, if you say John was the biggest, but he never hears anything about you missing John or happy memories of John, then he can feel good. But if he hears that Bill was biggest and you've occasionally mentioned that you really liked him, and thought it was going to last forever with Bill, or if you ever mentioned long/good sex sessions with Bill, your husband would feel like he didn't measure up.
It's likely one of those risky questions to either help or hurt his self esteem. We men are insecure creatures, even when we look secure on the outside.
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