Dear Dr. Olson,
I’m in my sixties and really enjoy giving blow jobs.
I have a friend I have known for years that crossdresses. His wife is very aware and helps him dress.
I would really like to suck him off. Should I ask him? His wife? Both together? My feeling is that I should ask his wife first.
Be careful, or you could lose this man’s friendship.
Just because your friend crossdresses does not mean he’s looking for someone to give him oral sex. In fact, as I wrote in “What to Do with a Husband Who Crossdresses,” the majority of men who crossdress are heterosexual. Many of them are married to women and are sexually active only with their spouses.
I have spoken with several men who enjoy wearing women’s panties and sometimes other lingerie. They give many different explanations for this. Many heterosexual men wear them under their clothes every day because they enjoy the way they feel.
For others, it is a fetish. Fetishes are a preferential interest in body parts or objects associated with that body part. They are used to enhance a sexual experience but are not a necessity. Fetishes are not necessarily a problem if they don’t harm anyone.
Some who crossdress feel sexy and seductive when dressed as a woman, while others do not connect this behavior to an invitation to sex. Many can’t even explain why they do it.
I would not presume to know why your friend crossdresses and what it means for him.
Some wives (most crossdressers are men) are supportive of their husbands’ behavior, although many are not. This situation is often very private. In your situation, his wife appears supportive of his behavior, but that also does not mean she would be supportive of him having a sexual relationship outside of their relationship. I would not recommend talking with his wife.
If you know him well enough, you could ask him to tell you more about why he crossdresses. But even this should be approached cautiously because it might provoke in him some feelings of shame or guilt. If you do discuss it with him, you must be prepared to answer some of his questions too.
In general, I would say that having casual sex with a friend, especially one who has a committed partner, is not a good idea. It often shifts the dynamics of the relationship and can easily destroy it. You can satisfy this desire you have with plenty of other men.
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