05/12/2010 11:34 am ET Updated May 25, 2011

Ask Michael Cohen: When Size Matters

I didn't think having a well endowed boyfriend would become an issue over the past year but it has. The problem is not so much behind closed doors, it's what happens when we go out. For example, the other evening we went to a friends cocktail party and he was wearing fitted (not skinny) jeans and a t-shirt. It literally looked like he had a tube sock stuffed in his pants. I'm already getting anxious with summer coming up -you can't imagine all the stares he gets in a bathing suit. Not to mention he is really good looking and in great shape. He has had some animosity towards me for asking him to wear dark colored suit pants to work and I don't want to nag him about his penis size during his free time. What should I do? Carrie, K. Venice Beach

Hello, I'm not sure why this is a problem? Your man has a job and a big penis? You've got everything Samantha Jones and a million other girls are looking for (not to mention a couple million gays). But I am relating to your woos and I will confess why. I once dated someone with an above average-sized penis and I put an end to show and tell real fast. Since you have already had some success with changing his work attire that is a good sign that he is amenable to change.

First, explain that you understand that he doesn't care what people see or look at because this will surely be his first line of defense - it's his free time in life and you get it. Empathy goes far. But also explain that the equivalent would be if you wore very low cut tops and very short skirts...everyday. If everywhere he went, there were men ogling his girlfriend, chances are he'd have an issue with that.  And so, rightfully, do you. So if he is committed to this relationship he should make some changes besides learning to put the seat down. I would start with these reasonable wardrobe suggestions, but if that doesn't work, try showing too much T & A--just a few tricks of the trade that may make a huge, pardon the pun, difference.

A few easy ways: Don't do the shirt tucked in, keep it out so that his member is not on full display below the belt buckle. Stay away from khakis and stick with dark washed jeans or black pants so you don't get that 'shadow' effect and no pleats which severely add to the bulge. Also, make sure that the pants he is wearing have a longer front and are not purchased at a tightly appearing size. Underneath, always wear high quality briefs (not boxers or boxer briefs) that will have a little spandex and will keep everything neatly packaged. 

I recently had an affair with my trainer. I know it's the biggest cliche in the world but it happened and there is a reason why. My fiance and I have been together nearly three years.  He is a surgeon, brilliant, sweet, caring and our families love each other. The problem is I am not really that turned on by him anymore and with out being too graphic, he doesn't satisfy me that way. Am I being foolish for thinking of letting my fiance go over his 'size' or is this something I should just deal with because he has so many other great qualities? My girlfriends wouldn't understand, he is everything they would want and I really don't have that feeling. Help. Anonymous, New York 

You're in trouble but it's all going to be alright. First, I do not condone this affair. I can understand how it happened, sexual attraction, especially when someone is extra hungry, can feed into a situation, but that doesn't make it excusable.
Secondly, who cares about what your girlfriends like, they obviously don't know the other side of the story, and even if they did, what bothers you may not bother them. Although I would tend to disagree. This is about what works for you and what you can and can not live with. 

Instead of having affairs, you should be open and honest with your fiance and try to find ways to enjoy sex--with him. There's a lot of literature out there on this topic. You can try different positions (I believe the kama sutra alone illustrates 64 of them!) or introduce toys into the act to make it more fulfilling. I'm not saying shock your man and come home with a 12 inch dildo, I'm just saying go to the playground (and I don't mean have another affair).

While I may dish out this advice, I would head towards something all together different and that is not to use fantasy, positions or sex toys to masque what you are missing. Something is not right in your relationship or you wouldn't have strayed. So get to the real root of the issue now. Honey you've been engaged for three years, maybe it's time to call the whole thing off.

I don't know how I got myself in this situation but I am a boob guy and my current girlfriend is pretty flat chested. Every time she asks me how she looks, I am thinking, "dam i wish she had bigger boobs." We've talked about  the T-job and she keeps asking me if she should get it and I'm saying no but the truth is I want her to. How do I do this without ruining my relationship? Mario A, Miami

First, I really hope this isn't a Miami thing because you live in a city where every girl seems to have huge knockers! Okay so lets get honest here. You need to get over yourself for thinking that your girlfriend should get a boob job for your own pleasure. You also seem to have ignited an insecurity issue.  

Let's do some reverse damage. First, discuss it in the open. Do not tell her she should get surgery. This must totally be a decision of her own that she does for herself. In fact, you need to tell her that you love her body exactly as it is (and if you're lying, and big boobs are that important to you, find a new girlfriend).

What you can do is suggest that you both head out to a proper bra fitting at a company such as where she can be fit with a bra that enhances what she already has. I have a feeling a lot of the girls you think have big fluffy pillows may be wearing all sorts of push-ups. 

This new type of bra will certainly build her outward confidence and together you should work on the inner confidence because I equate it to this.  If she took you to a penis doctor to give you more girth, as nice as it would be, it would certainly create some kind of insecurity that would need repairing. 

You can submit your questions on my website or in the comments section here.

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