My journey of self-discovery started so long ago that I can’t even remember its beginning. It could mean that my feminine feelings and desires were baked in at the start. The phases I’ve gone through parallelled what I’ve read and seen from other women like me. My interest in girls’ things goes back to childhood, the feminine feelings throughout my adolescent and teen years (in varying intensity,) thinking I had outgrown it, thinking I had “Married it away,” only to have it come back, to trying on my wife’s clothing, buying my own things, eventually to coming out to my wife and gaining her acceptance, and the end?

Well not so fast, it seems that with every milestone I reach, I immediately start thinking of what’s next and how to push the envelope a little further. In the beginning, I dressed at home alone, and then later with my wife’s help. She helped me with clothes, makeup, accessories, pretty much everything. I needed a lot of help because my instincts were so bad. Being a typical trans woman, I tended toward dresses or skirts that were too short, lips that were too red, my hair being too long, too curly, or too blonde.

Fortunately for me, my wife was there to correct and redirect me when needed. Over the next year, my clothes became more age-appropriate, my makeup more practiced, and my mannerisms more feminine. Dressing at home with my wife became comfortable; to the point that I knew it didn’t bother her. I could even tell she was enjoying it more and more until one day she told me, “I like you better this way.”

My wife has always been a little bossy or directive, so I went with the flow, at least while I was dressed. For example, if her clothes were in the dryer, and I needed to use it (or even if I didn’t,) I would hang, fold, and put her clothes away for her. If our room was a little messy, I would straighten everything up while she was out. Whenever I dressed, I would find something to do that I knew she would like and would also save her from having to do it.

Maybe this was a bit manipulative, but I wanted her to associate my feminine side with being something positive for her. This seemed to satisfy me for about a year until the urge to go out started to hit me. Like a lot of girls, my first outing was to the gas station to fill up (how brave?) The next outing was the Wendy’s drive-through. I finally worked up the courage to go into a Walgreens, making sure it was one in a different part of the city. It took place during the pandemic when I wore a mask along with my dress and heels. I remember walking through the front door, my purse slung over my shoulder just as I practiced many times at home. I expected the Earth to spin off its axis, but nothing happened. Nothing except me picking out some lipstick, and standing in line to pay for it, and then getting back in my car.

EnFemme

Over the following weeks and months, I took every opportunity to get out. Sometimes, I would go in, and other times I chickened out, leaving without even getting out of my car. I started choosing my spots, such as TJ Maxx or CVS, usually going in the evenings about 30 minutes before closing time when virtually no one were in the store. Gradually, I began to go earlier when there were more people. I made it a point to buy something (even if I didn’t need it) just to stand in line with the rest of the women and pay. It may seem like small steps, but to me they represented progress.

In August of 2021, I started attending an affirming church. To my amazement, there were several in my area (Jackson, Mississippi). From the moment I walked through the door, my life changed for the better. In addition to the membership, which is 95% LGBTQIA+, I became connected to PFLAG, Capital City Pride, The Trans Program, and an organization where I can volunteer as a woman.

During these “Outings” what stood out the most was how no one seemed to care, even that no one seemed to notice. Over the last couple of years, I’ve been going pretty much anywhere, any time of day. Recently, I went to our neighborhood grocery store at 9:00 in the morning. Also, I’ve started asking my wife to make shopping lists, so I don’t rush in and rush out. It takes me a while to find what she wants, giving me time to search up and down the aisles. Once I have everything on her list, I select the longest line so that it takes longer to check out.

Just this morning, I was dressed and running some errands when my wife texted to tell me she had a prescription at CVS to pick up. “Why not?” I marched in, went to the pharmacy, and walked out with her prescription.

Just remember girls, it takes time to undo a lifetime of conditioning. We’ve all been taught that boys don’t wear dresses or makeup or other typically female items. Well, yes they do, yes we do, and yes I do.

My most enjoyable times are spent as a woman, especially with my wife as two women. Everything feminine makes me so happy; it’s hard to explain. So I’ll keep dressing, and I hope all of you will, too. Please ask me anything, I always love chatting with my girlfriends.

EnFemme

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Jane Millane
Lady
Member
18 hours ago

Well that was a delightful read, l was smiling while reading it. I am still in the closet, my wife encourages me and buys me clothes make up etc. She puts my make-up on me and is going to teach me how to put make-up on. I am not ready yet to go out in public, l said to her the other day that l felt like l was weird and she told me that l was normal and she loved me. Every story l read helps me to get closer to going out in public, thankyou for the story,… Read more »

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