I Don't Think He Knows!

[Alana]

You are just a big softie, letting her win and wear the dress.
 You look so cute in that petticoat - and you definitely have the egde on looks over your sister - you definitely have a much sweeter, delicate face.

Thank you. We fight a lot, but we love each other. I remember the time she got so angry at me she pulled my dress down in front of everyone! She was just a schoolgirl back then.

[Alana]

Gosh, she has quite a scary look on her face there - I wouldn't want to meet her in a dark alley.
 Cool action shot though - who took the snap? As much as it is cool to see you in your petticoat again, I couldn't take my eyes of your legs in that shot.
 Do you mind if I ask if you are married, and if so, is your husband OK with you sharing these photos with me?


No, I'm not married. I'd like to go on talking with you and basking in your wonderful compliments, but I have things to do. Here's a little picture of me playing secretary to remember me by. I hope you add a few comments to some of my photos sometime.

[Alana]

I was actually just going to write and say that I really need to get on with some work - I've been too distracted by you this morning.
 I'll have a look at the picture when I get home.
 ps. Amazed, but pleased, you aren't married :-)

I didn't know what to think after all this. Could he really not know? I thought I'd better set him straight. I sent one last email for the day, directing him to my profile page, where it stated I was a heterosexual crossdresser living in Northern California. I waited patiently for his response the next day. And it was a very strange response.

Hello Alana,
 I've been wondering all evening whether to email. I read your profile when I got home and didn't know what to say.
 I've never heard of someone transitioning to male, all the popular media is of men becoming female. That must make life very difficult for you. Thank you for letting me know about that part of your life. I assume you have another anonymous Flickr profile for when you get the chance to be the guy you are inside.
 I really hope things work out for you and that one day you are able to live as a man full time (even though that means we will lose an incredibly beautiful woman).
 Best wishes,
 Simon

Wow! At that point I was really starting to think, I don't think he knows! I really don't think he knows! What woman refers to herself as a crossdresser, anyway? A woman who occasionally dresses as a man would be called a woman. Women can wear whatever they want, as we all know. He was clearly confusing crossdressers with transsexuals. Well, I hated to bust his illusions, but I had to tell him the truth, even if it meant the end of our flirting. I emailed:

You have it backwards. I'm a man, and I like to dress like a woman, sometimes. I'm not transitioning, I'm just an occasional crossdresser. I kind of thought you knew and were just playing along. Anyway, I don't want to make you uncomfortable. I enjoyed flirting with you, but it was just playing around, and that's all.

And then I didn't hear from him for two days. I felt bad about the whole thing, so I sent him another email, changing the subject line to "I hope you're not upset":

I haven't heard from you since I had to tell you that I'm not a woman. I hope you're not angry or embarrassed. If you are, I want to apologize. I'm sorry. I should've told you sooner. I honestly thought you knew, and you were just kidding me and playing along. So I played along, too. I'm sorry. Please email me back and tell me that I'm forgiven.

And he replied:

I'm sorry for not replying sooner - it was just a lot to take in. I've just woken in the night and realized it was very rude of me not to reply. I don't blame you, I just feel very foolish (though I guess there was no way I could guess).
 I have to say that for someone who says they are an occasional crossdresser, you do it very well - you certainly have a better sense of style than most women. You should run courses for women!
 Best wishes,
 Simon

I thought it over and sent him back one last email. I have never been so complimented in my life, and I thought of him looking at my photos and probably pleasuring himself, and I couldn't help but think of him fondly. He never responded. I think of him sometimes, and I wish him well. Here was the final email between us:

Well, I don't want to be some kind of stalker, so this will be my last email to you, unless you respond. I just want to tell you that you are so sweet! I've never received so many wonderful compliments in my life! If I were a real woman, I would be yours, because you've just about charmed the pantyhose right off me. I can just imagine looking in my closet and picking out a dress to wear on a date with you, looking forward to you seeing me in it, looking forward to you taking it off me later. But I'm not gay and you're not gay, so there it is.
 So before I go, possibly for the last time, I just want to ask you one question.
 Do you think I look cute in this dress?