Two of my favorite MTF girls Diane and Janie joined forces for the first time in February 2019 and they blew me away! I did their makeup and then took these sensual images.
After, I asked them a few questions. I'm sure you will find their answers interesting.
Here are Janie's answers. (Janie is the sexy dark-haired beauty in the pics)
1. What's your earliest memory of crossdressing and how old were you?
There are two “phases” of my dressing (but a lot in between)—an Oreo cookie is the way to picture it. When I was 4 or 5 years old, my grandmother dressed me up in white tights for a photo and I loved the feeling of the tights!
When I was 21, I was living on my own having landed my first “real” job and that was when I tried going 100% en-femme and that’s when I fell in love with trying to be as passable as possible with clothing and makeup. I probably looked ridiculous but it was like hitting puberty for the second time—the feeling of femininity and exploration of parts of me that were considered socially taboo was a tremendous learning experience.
The irony is that all of these “feminine” labels in terms of lingerie and makeup are all social constructions of the modern age. If you look at nature, it’s many times that the male can be considered “beautiful” and alluring (peacocks, lions, etc.), but I digress…
2. You are both Family Men, married to biological women and each have a small child. Did you tell your wife about your crossdressing before or after you got married?
I had neither a great deal of dating nor sexual experience before I was married. My girlfriend at the time, who happens to be my spouse, knew this. We were making out heavily for the first time and she became flustered and commented that she was very skeptical about my claims of lack of experience and she asked where I learned to kiss. I told her that my secret was that I had some help and that it was the fact that I enjoyed wearing women’s lingerie on occasion and, while dressed, I often imagined how to make out to a beautiful woman. I think she was amused and also took pity on me—common themes in our relationship to this day.
It was much later on in our marriage and after we had a child that I came out to her about Janie and all that it entails. She didn’t bat an eye and asked, “Are you gay?” The inquisitiveness and open-mindedness of my spouse turned that one question into a series of positive dialogue where we both explored and learned about each other and our marriage. It’s still a work in progress.
3. Does your family, friends, and coworkers know of your crossdressing?
My spouse knows about Janie. I go to a transgender group a handful of times per year and have made some friends, I’ve gone out in public a few times, and of course, Adrian and Diane know about Janie.
4. Have the folks who know about this side of you expressed how they feel about your crossdressing?
My spouse thinks I still look ridiculous yet has given me pointers and comportment tips and has refined how I present as Janie. Is it a covert ploy to get me to buy her more handbags? She’s smarter than me so I would never know.
5. Was this the first time you've ever done a dual crossdressing makeover/photoshoot?
Yes!
6. How did you feel before, during, and after the shoot?
This was my third photoshoot with Adrian who is so welcoming and awesome that I felt totally comfortable. Also, when you’re shooting with someone so pretty like Diane it was so much fun!
7. What is your favorite memory of the shoot?
The improvisation and great chemistry between all three of us. It was so organic, sensual, and time flew by.
8. Why do you think so many folks who crossdress are in the closet?
Humans are pack animals and it’s much easier to survive as a “male” in our labeled society by wearing jeans and a t-shirt than express oneself the “wrong” way with stockings and pair of 4” stilettos.
Also, until fairly recently, it was much harder to get information, share ideas, and connect with similar people so individuals who crossdressed were much more isolated, confused, and repressed.
We’re living in amazing times and hopefully society gets its head out of its ass. I’m an optimist and I’m confident it will.
9. There are numerous Gay, Lesbian, and Transgender popular figures today yet very few popular Crossdressers why do you think that is?
Crossdressing is a super-broad, multi-faceted label which blows people’s minds. When you go to the store, people have trouble picking out which olive oil to buy even though the choices are determined by someone who probably doesn’t wear a pair of Wolford and Stuart Weitzman thigh-highs (this is a subtle birthday wish list). A way to speed things up in terms of progress is for Marc Jacobs to design the Pope’s ordinary dress and for the Pope to totally rock it.
10. If you could give someone who crossdresses one piece of advice what would it be?
Don’t live vicariously through others; be inspired to go on your own journey because life is very precious and it’s your chance to make it exciting for yourself and those around you.
