Friday, October 2, 2020

Your First Time Out

In my previous post, My First Time Out, I described my less than wonderful first time out en femme (not counting Halloween). That experience might have been better if I had some sage advice beforehand, but where was a poor girl to go to get that advice back in 1990? 

There was no how-to literature to read up on. I knew no other femulators to consult with. Online, all there were were bulletin boards, Compuserve and 110 baud (read: incredibly slow) modems. 

Can’t rememberers where online, but I did find a list of local support groups and finally got the nerve to phone the contact person for one of the groups and she gave me the time and place of the group’s meetings. I guess I could have asked her for advice, but it never crossed my mind and it was hard enough just making that call.

I don’t have to tell you that times have changed and today you can find loads of advice and how-to information on the blogs and websites that proliferate on the Internet... even here.  

With that in mind, I poked around the Internet to find advice for your first time out en femme and I believe I found a good article on the subject: “Crossdressing — Going out in public for the first time” by Fiona Dobson. Her suggestion about going to a drag club was something I actually tried successfully my first time out en femme in Dayton. 

If Fiona’s advice is not your cup of T, then Google “first time out crossdressed” to find something you are more comfortable with. Whatever advice you follow, just do it. Get out of the closet and experience life as a woman. I so regret hiding in the closet for so long and I don’t want you to wait until you are an old lady before you go out as a lady. Just do it!

Wearing Unique Vintage
Wearing Unique Vintage

James Charles
James Charles


  1. I like to tell people that’s it’s like jumping off the high diving board. It doesn’t seem to make sense so you just have to say “#%*$ it” and do it. Then you realise how much fun you had.

  2. It was Halloween, I had entered a contest held at at a night club. The theme was "Hell on Heels" I was trying to win a $500 top prize to help my daughter out! Sadly I didn't win, however I ran into someone from work who I didn't realize they were "not a civillian" So the following day was the company Halloween party! Talk about nervous! Came in 2nd place and gave the $50 to my daughter. I had been dressing for years, but that Halloween weekend was the 1st time "Sara" had seen the outside world!
    Just like Angela said, just suck it up buttercup and step ou the door and do it!

  3. i could say my first time out was when i could finally afford to rent a flat of my own whilst living in a suburb of london in the early 90's. as you may imagine i took advantage of my new-found freedom most evenings, and as such was quite content with only a packet of fags and a bottle of wine for company. although i had been aware for some time that i was not the "omega tran" thanks to various things i had read and seen in the media, it was only then i learned there were social events that catered for such clientele. they were advertised and sometimes even reported on in the city's "what's on" magazine, that liked to expose the more alternative/underground scenes to its readers. and there was once even a fantastic picture of one such punter posing in a ballgown on the front cover (that i wish i had kept for my scrapbook now ha ha). so after the novelty of dressing alone at home started to wear off, i found my curiosity in attending such an event being piqued. yet the fear of discovery and being condemned accordingly stopped me from doing so - even though unlike for most it was relatively convenient (the nearest i got was going to a soho drag cabaret nightclub called "madam jojo's" once or twice in mufti). so my "proper" first time out had to wait until i moved "oop north" several years later!

  4. I had gone out with members of the Trans*Quility group several times. It was amazing how free I felt. But it was about time I went out on my own. As it happened with many of us, Hallowe'en was coming up and I decided that would be the night. I had found a really good place to shop for tall clothing -- a JC Penney outlet store in West Baltimore. These stores were stocked from items from the Penney Catalog, which sold lots of tall and large sizes. I bought a long black evening dress with a square, low cut bodice.

    At that time my hair was down to my ass. I also bought an electric curler set at Penney's, which I used early in the afternoon and kept them on until after 6. I spent a couple hours doing my makeup. I glued on my black nails. I boosted up my boobies and put on a necklace with a black spider resting between "my girls". When I took out the curlers my hair was BIG! I hadn't any idea how it would turn out, but I loved it. So off I went to The Hippo, where I had gone to many drag shows as Mike and as Mikki with my group. I got lots of compliments and a few queens threatened to steal my hair! If anyone who knew Mike saw me I never found out. And I discovered that it was just fine to be Mikki and be out and about. I don't know those folks and they don't know me. and that's the case with pretty much wherever I
    might go. Mikki was free!

  5. My First Time . . . Out
    In 3 stanzas -------
    1968: a weekend during high school days, at home alone,
    at 11 pm on a Saturday night i finally got the courage after many outfit changes to walk around block in my grandmothers a-line skirt with a fancy lace blouse, no make up or wig.
    1970s: many trips to the Blue Ridge Parkway in femme.
    1979: first trip to a Halloween Party, after buying my first real wig in person, en femme - from a retail store, the shops owner could not have been nicer. @ 9 am.
    Followed by a cross state six hour drive to the gala in Norfolk, VA.
    Heart racing many times, including three stops to shop en femme for the first time; in Williamsburg outlet stores and a department store in Colonial Williamsburg's Market Square.
    Even a stop at the Black & Decker outlet, where the only female Clerk had a jolly time helping me, after the men just walked away.
    Traveling completely en femme
    Including tampons, to a party at the home of the Medical School's Dean. Wearing a red column skirt with a beige satin top and a Red lace bolero jacket, the first time the term Ma'am was ever used to me, my B cup breasts were saluting the world from a bare skin decolletage with the help of a Frederick's extreme bra - until my voice combined with a six - two frame in four inch heels gave the party goers a start.
    Ah what I would have given for six years of femulate posts from the future in a bound pamphlet before the trip! A Femulators Guide to Our Universe in time slip format, where oh where was that time machine phone booth: then-ly ???

    Roanoke, Va