My adventure out

[DCChris]

TLDR; my makeover session went well, my first time out with a couple others in the community at a Long Island diner went well, and the evening with a gf in Philly, well ... [redacted due to self censorship ]

The Long Version
After a lifetime closeted, I've long wanted to take the next step to venture forth and subject myself to the unjust criticism of the cruel world -- I mean venture forth out en femme for the first time.

With plans set, I drove to New York long before the crack of dawn for a mani/pedi complete with acrylic nails and polish. The salon on Long Island I went to caters to the community and has some very nice private rooms. Although it took twice as long as I had expected, the result was what I sought. Went in drab, left in drab with nails on my feet and fingers looking stunning. I have now gained a HUGE new respect for women who wear longer than sport-length nails! And omg, driving with longer nails was also not easy, lol. Now how in the hell do I get my seat belt on with the cop eye balling me ..

I then left to my makeover session with Karen on Long Island (Femme Fever) who performed the miraculous, imo. She took a 50-something guy and turned him into something that wouldn't frighten the children (as my own make-up sessions at home have shown). She explained everything as she went along, and which I can't possibly remember all, but she gave me the confidence to keep at it. I walked away with a wig I liked, forms, a number of pictures in the two outfits I wore to venture out in, a few other things and a whole lot of great memories of my time with her. YMMV, but I highly recommend her from my experience.

Then it was off to a nearby restaurant/diner to meet a couple gurls who had offered to help me out for that first public experience; they thought they'd have to come pick me up, but I had no problem driving there with my new found confidence! We talked and talked, had a few people glance our way, but the entire staff knew the gurls I came in with and made it a very good experience. Before heading out to Philly, I had to do one more bold thing ... visit the ladies room, which wasn't as bad as I feared; no teenage girls or small children in there, lol. I then changed into my evening dress at one of the gurls home who lived nearby.

So, now off to Philly! Wasn't sure how all tolls stations would go, or passersby in cars. But, you know what, people seem to be focused on their own driving and just taking your money at the booths. Except one guy. I could swear he said, here's your change hon, and give me a sexy smile, to which I responded back, of course, "you're welcome" in my masculine voice. As I hit the accelerator, he looked confused

In the end, it was this gf, who visits a couple times a year from overseas who convinced me to do the makeover and go out. She is about 18 years younger than I, far more adventurous and bi. In the process of our play times together, she asked if I'd like to do some reverse role play and long story short I told her about my CD interests. She thought it was pretty cool, and has since pushed me to do more.

Anyway, we had arranged a 'fantasy' where I'd meet her at her hotel at the bar, strike up a conversation and then head to our room. When I walked up to her, she almost didn't recognize me (in a positive, good way, not the OMG! stranger danger kind of thing) and although I wanted to head upstairs right away (the bar was a little too crowded for me), she said: "the woman who did your makeover did a great job, you look sooo passable. Let's stay here for awhile." So, we ended up spending two hours at the bar, drinking, laughing and having a wonderful time.

Later, we headed back to our room for the night and had a lot more fun [redacted due to self censorship ]

Hopefully, a couple pics are attached (assuming I did this right). The brown skirt and blouse I wore to the restaurant, and the white and black dress I wore to Philly. The clothes are courtesy of Dress Barn, where I talked about that good experience in a recent thread.

And, hopefully, you will enjoy too.