Dear Dr. Betty,
I found out that my boyfriend has an attraction to transgender women and also likes to cross-dress sometimes to heighten his sexual arousal. He was very embarrassed when I accidentally discovered his attraction. I initially freaked out but have begun to accept his desire especially since I did not want him to feel any additional shame.
He has been open about not knowing what his attraction meant, and has done some soul-searching and says he is not gay or attracted to masculine or gay men. I understand this. I myself am incredibly attracted to boobs but identify as straight because my relationship preference is with men. In an effort to incorporate his fantasy he has dressed up for me a few times and I've strapped it on for him. I have encouraged him to explore his desires by seeking an encounter with a transgender woman.
I so want him to explore his fantasy so that we know where it will bring our relationship in the future. Truth be told I'm scared shitless. For a few reasons. 1) How can he find a way to explore his desire safely (STD-free, etc.) and 2) I'm nervous about losing him to a sexual experience he might be drawn to exclusively. On the other hand I don't want him to repress his desires. Also I need to find a way to be more genuinely comfortable with it. I am turned on by his masculinity and I don't want this to "taint" him in my eyes.
Without knowing your age, I can say you are a very wise woman! Congratulations on dealing with your boyfriends interests that would undo the average person. Sexual identity is still in the dark ages with our very limited ideas of being straight, gay or bi. Back in the seventies I was told I had to chose a sexual preference but I refused. When I'd say "I'm a heterosexul-bisexual-lesbian." the conversation ended. Today I'd have to add a few more labels until it becomes exhausting. Truth is that we are all simply sexual. And that can take numerous forms that are constantly changing if we're fortunate enough to grow.
By the way, if I'm not scared "shitless" on a regular basis I don't feel alive.
So to answer your questions:
1) How can he find a way to explore his desire safely (STD-free, etc.)
This is just a matter of asking a few direct questions and using good sense. Also we have functioning Immune systems that the medical professionals want us to ignore so they can remain the High Priests(esses) who have all the answers. You know the drill: Organic food, exercise and orgasms.
2) I'm nervous about losing him to a sexual experience he might be drawn to exclusively.
Yes, that is a possibility. But it's best to find that out sooner rather than later. He is not the only fabulous lover for you in our big wonderful world. Stay strong and continue on the path you've chosen to help him and you to discover the multitude of gender roles that have endless possibilities.
I just watched Buck Angels' documentary on NetFlix. He's a transgendered female to male. He has a massive muscular body all covered in tats with a shaved head. But he didn't get bottom surgery, so Mr. Angel has a magnificent clitoris and he loves his vagina! His wife who wrote the bible on tattoo artistry love his big clit and vagina too. Ain't love grand?