Jocelyn’s First Wig Adventure

By Jocelyn Johnson

This post means quite a bit to me. It is the reason I keep doing this blog. I have recently considered shutting it all down, I do that often. The truth of the matter is, this is work. And it is work that I get paid nothing for. I get no direct human feedback, from real people in the real world. E-mails, comments, all wonderful, but they are virtual. But this is a labor of love. This place also apparently means something to some beautiful people. Jocelyn is one of them. She reached out to me through the “Contact” page on November 28 and here she is, sharing with out little community. She is a genuinely beautiful person and I am privileged to run this post.

Since getting back into crossdressing, after decades since a mid-thirties purge, I was contemplating the order of restocking my closet. Should it be shoes and a dress first, or get a wig and then go shopping for a wardrobe? I do not like shopping online since I prefer to see the item, try it on, and then purchase it if it all fits and the price is right. But a girl shopping for shoes and clothes with short grey hair is not good, but wig shopping in a dress isn’t a good look either. I also thought I could not go in a skirt, nor in regular jeans or slacks. So a few days before, I went to Walmart to look for some leggings; which I thought would be more feminine looking. I tried on various styles and sizes and eventually settled on maroon Jordache leggings. They look good on my legs, but I don’t have the hips and derrière to fill them out appropriately. Oh well.

I made an appointment at a wig store in a nearby Town that specializes in serving cancer patients and cosmetic customers. They do wig fittings by appointment only. So, Monday Jocelyn was to see a lady at the shop.

On Monday I got dressed in the leggings, a bralette, a sweater, flats, and a simple gold colored chain necklace. I only had foundation makeup on. I drove to Town, and because it wasn’t a cold day, I walked up the street like that carrying a pink wallet.

I was nervous when I approached the shop and went in. There were no other customers there and the shop owner was very welcoming and friendly. She asked if I was Jocelyn, and I was! My short grey hair was a dead giveaway that I was an “old man” looking for a wig.

We went to the back room and for the next 45 minutes I had a marvelous time trying different styles and colors of hair. The sales lady was quite helpful and she offered a few makeup tips as well. Her best advice was to color my eyebrows to match the color of the hair. When I looked in the mirror with the brunette hair, the grey eyebrows made the whole face look odd.

It cost quite a bit more than I hoped, but the quality is good. Of course I had to get a wig stand, shampoo, cleaner, and brush. And paying for it all on a credit card with a different name didn’t seem to matter.

This experience was my first, spending so much time with a stranger, and just being Jocelyn.

A few days later I took a number of pictures with my new hairdo. I’m not sure I made the right choice. Maybe the look will grow on me.

How lucky am I to make these connections, get to know beautiful people like Jocelyn?


I also received the following message this past Saturday on one of the forums I monitor (I made some edits to respect her privacy):

Hi Kandi. Thank you first off for accepting my friend request! Thank you also for your blog. It’s wonderful! I just found it a few days ago and have been enjoying it immensely. (Except the part where the Browns beat the Eagles-but hey, not YOUR fault-everyone beats the Eagles these days).

I surmise from your one post that you’re a practicing Catholic? Me too. I would LOVE someday to attend Mass as Jennifer. Unfortunately right now I’m struggling even to get out of my closet. My wife is not very accepting yet. Perhaps that’s why I’ve so enjoyed your blog. You show me that maybe someday I can embrace my femme side more fully and more meaningfully than is possible now. Thank you for that most of all.

And this is what we do and why we’re here!

7 thoughts on “Jocelyn’s First Wig Adventure

  1. Great purchase Jocelyn. That wig looks great on you. I recently purchased my 1st wig in 20 years. I use my own hair and bought it for a change. I went in male mode and had no problem. I wear it when I don’t have time to see my hairdresser or style my hair.


    1. Terri,
      Thank you for the wonderful comment. I do need opinions on what works and where improvements can be made.


      1. Jocelyn, my advice is just enjoy the experience. Life is not a beauty pageant. Look in the mirror and if you like what u see , then go out and have a good time. I have sometimes looked at pics of me and thought I didn’t look good. But I remembered the time it was taken and remembered how good a time I had.
        Huggs Terri


  2. Jocelyn Your new wig looks good a great choice My only comment on your looks and I think you look perfect great choice in style for blending, which is what I strive for, is get some hips. I like Classic curves for their ease of wear but there are many out there. Amazon or others They all do the job. Glad to see your getting out and about and enjoying yourself. I need to do it more often and above all HAVE FUN thats what I think its all about


    1. Sallies,
      Thank you so much for your thoughts and support.
      I cherish the comments and suggestions I receive.
      Us ladies have to stick together.


  3. Kandi-if you ever visit out of Ohio and let others know I’m sure you will be able to achieve some human interaction
    (written from SW Florida)


    1. Thank Em, but finding human interaction has not been a problem for me. You will soon see on the blog a good 7,000 people I got to interact with last week!!

      By the way Em, I just realized, this post is a repeat from back in the heart of the pandemic. I should probably have stated that. We are really only rerunning old posts by my contributors here right now as all the new content is on the new site. Thanks dear!!


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