My Man's Junk Is Just Too Big. Help!


Dear Willie D:

I have been with my boyfriend for six months and we still have not officially had sex. The reason being is he is too well-endowed. I have tried to be understanding of his issue and he has been patient with me, but it is very frustrating for both of us. Normally he is able to get the tip in but that is it. We have oral sex but I do not enjoy it as much as I do penetration.

I have really been trying to please him, and myself for that matter, but I do not know what else to do. His birthday is in a few weeks, so hopefully I can get an answer from you by then. Thanks in advance.

Trying to Please:

It could be because you know what's coming you're tightening your vaginal muscles making it more difficult for your boyfriend to penetrate. So try to relax. You don't need tampons, cucumbers, dildos, or any other pulseless, silly objects to loosen up. Trust me, everything you need is attached to your man's body. He just needs to know how to use it. He needs to slowly and gently insert one figure inside of you to the first knuckle, which is located at the base of the finger.

Once he gets it all the way in he needs to move his finger in every direction to stretch you. If it hurts tell him to stop but try to continue. After he pleasures you for a few minutes with one finger tell him to repeat step one adding another finger each time until he thinks the width of his collective fingers equals the girth of his penis. Apply lubricant as needed. Because the vagina is designed to stretch, this is something you should be able to get through within a few days.

Remember, practice makes perfect, and in the words of that '70s funk band B.T. Express, do it 'til you're satisfied.


Dear Willie D:

I'm a 30-year-old woman who is crazy in love with a guy who has been my best friend since I was a freshman in college. But I don't know how to communicate my desires to him. He is wonderful to talk to. Anytime I'm having a rough day I can always call him, and even if he's busy he'll make himself available to accommodate me. I'm not dating anyone at the time but he is; I just don't know how serious it is because he is clandestine in regards to his dating life.

I have seen two girls he's dated and they are absolutely gorgeous. Although I don't think I'm gorgeous, I have been told that I'm pretty quite often so I feel as though I have a decent chance with him. I really like him; no, I'm in love with him. But I fear that if I reveal my true feelings, even if they're reciprocated, it will eventually destroy our friendship. What should I do?

Crazy In Love:

Never give up on pursuing a goal before the outcome is decided. Since he's in a relationship, you need to gather intel on how serious it is before you advance. Next time you speak to him casually ask him how things are going with her. If it's serious, you should give yourself a timetable as to how long you're willing to wait to see how it plays out before you disclose your feelings. If it's not serious, just talk to him like you always do and tell him how you feel.

Relationships don't come with crystal balls. What makes them appealing is excitement and unpredictability. It would be horrible if you guys forged an intimate relationship, broke up and ended up hating each other like many couples do. But that's not the worst thing that could happen. The worst thing that can happen in life is an opportunity unpursued because of fear.


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Ask Willie D anything at, and come back next Thursday for more of his best answers.


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Stuck In The Friend Zone: Assuming you were 18 when you started college and you're now 30, you've been pining for this guy for 12 years.  If he hasn't shown anything other than platonic interest in 12 years, he NEVER will.  Trust me, I've been where you are. Cut the ties and move on.

Rhonda Hare
Rhonda Hare

~ Excellent as always! Agreed all-around, but to add to 'Junk Too Big'... No need to wait; START with lubricant! That will make everything glide easier and help prevent vaginal tearing & friction pain/irritation. I'd recommend one that's silicone-based (unless she's sensitive/prone to infections, in which case it should be water-based). ^ Professional suggestion


Too Big (Not Big Enough)?: You don't say anything about your own history so this might not even apply, but go to your gyno and ask about vaginismus.  If this is an issue you've had before, it might be more than anxiety and finger-wiggling might not help.

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