Appropriate or not: Can you ask someone if their friend is a tranny?

I recently came across some photos that include a friend of mine, and one of the other subjects included in the series of photos may or may not be a transvestite. Now, if you know me at all, you will know this is a question that will bother me for weeks on end unless I get an answer. Tranny? No tranny? Vajayjay or junk? Ack! I'm already unable to sleep!

Now here is my question: Can you ask someone that is somewhat of a friend if THEIR friend pictured is a tranny? What if this person is their love interest? What if the tranny/not tranny in question is their best friend? How do you begin a conversation that could lead to this question coming up naturally? Here are some of my ideas:

1. "I realized today that I'm so tired of having to sit down to pee. It just seems like an extra step. You know what I mean? Of course you don't - you're a dude. But...what about your friend so and so? What are he/she's thoughts on the subject...?"

2. "I ran into an old pal of mine and he's a tranny now! He does a mean Barbara Walters impression. Know anyone that might be interested? What about so and so?"

3. "Man, chicks with dicks are so admirable. I don't know how your friend so and so does it! Wait...I meant so and so...oh my, I've had WAY much to drink!"

I think all three give me a way out if I get no response because, as the case may be, the he/she at hand might actually be just a she. An unfortunately looking manly she, but a she none the less.

Feel free to leave suggestions on how to bridge this topic. The best one wins a prize (as yet to be determined by author).