In the bisexual sense one can assume that he is simply trying to recreate the sexual act performed between two men (anal sex). I could be completely wrong but that is what came to my mind first.
A man might ask a woman to wear a "strap on" if he wished for her to penetrate him anally, or perhaps he would like to suck or fondle it? Personally I've no real idea as it isn't something that interests me.
EDIT:-
Its a fantasy. Each person has different turn ons. Each male that wants a woman to wear a strap on have different fetishes to fulfill. They may enjoy the dominance of being penetrated in the anus. They may also have a fetish for what is termed as a Shemale. A male that has transformed his body into a female equivalent except for his penis. He may not even enjoy the concept of being penetrated but the concept of the penis.
If there are more than just him and her he may wish to enjoy watching two females having intercourse. So for her to use the strap-on on the female.
But as stated there are various reasons for this but each male is different. But generally it is for being submissive towards a dominant female.
EDIT
My Husband also likes for me to ware a strap on. I don't necessarily like it. But i do it out of love. I think it has to do with hitting the prostate. The way I deal with it is I just Hold my breath close my eyes and while I am doing that I just have a fantasy or imagine something different in my head. Try it it may help if you are uncomfortable doing it like I am. None wants to disappoint the ones they are in love with. As a matter of fact, my husband told me he had a thing for she males, so I don't think that person was to far off, he also has a weird thing for body building women that look like men. I don't get it. Sometimes it will make you feel like you are not good enough but you just learn to deal with it. Or, if you can't your gonna have to get out of this relationship.
EDIT:
There are many reasons a man will find strap-on's arousing.
It is just a sexual preference. Everyone has them. Some women want to show power play over their husband, or dominate him. This is just another way of doing it.
Just as a man wants to be feminine some men want to be taken by their wife or SO and this is a good way to do it. Gives pleasure to both so is a win-win situation.
sandle
The woman wear hijab and abaya and the men wear thobe
the Men were type of things they Meant to wear to war same with woman
The same thing men wear: shorts and a jersey.
the woman wear flapper dresses and the men were hipis
the woman wear cheong-sams a skirt and the men wear suits
men want you as an option, and women have men as their priority Answer cuz their stupid!!!!!!!!!!!!!!!!!!!
If you wear an 11 in women's shoes, then that is equal to a 10 in mens.
well you shouldn't be wearing men jeans if you are a woman!
Prehistoric men/woman wore the animal skins from the animals they killed for food.
not all woman and men do. Also because we are made differently!
Men should wear speedos and woman should wear bikinis and bras