I agree with Mashie. I felt the same way about enemas, wanting to be given one, but terribly afraid of asking anyone to do it. After twenty years of no man asking about it first, I decided if I didn't ask for what I wanted, it would never happen. I was dating a man who enjoyed giving me anal sex and he didn't mind prostate massage so I thought he'd be open-minded enough to give it a whirl. Oh, boy, was I wrong. He screamed like a girl, said "No way! No how! Never!" Months later, we broke up for other reasons.
The next man I dated was also anally-adventurous and owned a copy of Nancy Friday's Women on Top, which is where I found the first erotic enema fantasy/story. One night, we were talking and I mentioned his library and that book. I asked him if he had any favorite stories and he mentioned a few. Not the one I was thinking about, though. So I told him I had a fantasy but was too shy to tell him which it was and asked if he'd try to guess it. He made a few guesses, to which I answered no. Finally, he said, "There is one in there about a woman who wants a bunch of enemas or something." I said, "That's the one." He started laughing in that hard-to-believe kind of way but didn't say no. However, we broke up soon after over something else.
So I endured a bit of embarrassment and rejection but by asking for what I want, I at least conquered my fear and have learned that I will not die of shame if I am rejected. I decided that before I ask someone, I give a little disclaimer first and explain that what I like is a little bit taboo and somewhat unusual but to let me tell them about it before they say no or make any judgments about it. That what they think it's about, isn't what it really is. (You know, the whole enema=scat thing.) I have found that men are receptive when you ask them to listen without judgment. Either that or I've just found the right men to ask.
So supernewguy, if you want a gal to use a strap-on on you, it might be a good idea to drop little hints. Maybe give her bottom a lot of attention and pleasure so she can see how good it feels. Once she realizes the pleasure involved, she might understand better why you would find it enjoyable. Tell her you'd like to feel some of the same sensations she does and let her explore with her fingers and toys before working her up to a strap-on. Assure her that you wash yourself really well (You do take enemas, yes?) and that it wouldn't be dirty or disgusting and that it would really turn you on for her to do that to you. Trust me, once a lady sees your anus spread open from her fingers and all that pink goodness inside, she'll totally be addicted to exploring you there. Tell her that it's exciting to make love to her anally and you love seeing her in that position and that you'd love her to do the same to you. If she has qualms about using a strap on, versus a dildo or anal plug she manipulates with her hand, gently inquire why she is opposed to it.
For me, I didn't want to use one because I've always hated the look of harnesses. They look like jock straps and not the least bit feminine and I hate the whole butch for me. Also, it's difficult, though not impossible, to find one that fits larger women like me. I also worried that due to my health issues, I wouldn't be able to get into many positions and be able to be on top. I was also concerned that I wouldn't know how to do it properly and just make a jackass out of myself. But Mike really wanted to try Feeldoe so I finally said "What the hell." and bought one for us to use. Actually, I purchased the Realdoe version of it because it looks and nearly feels like a real penis and it is a little bit longer and thicker than some of the Feeldoes available. A feeldoe, by the way, is a strapless strap-on. I has a bulb that is held in place by the woman's kegel muscles and the rest of the dildo part is just like others you see. It also has a bullet vibe in it that stimulates both partners. For creative men, the Feeldoe can be inserted into your anus so you can give your lady friend double penetration.
Whatever reason she gives for not wanting to use one, try to find an agreeable solution so you both get what you want.
I guess what I'm trying to say here is COMMUNICATE. If you don't speak up, it may never happen to you.
Dianne