Have you ever experienced a time during your crossdressing where you just stop? If you are like me I usually can’t wait to get home from work and open that closet and pick out some pretty things to wear. The past few days I have arrived home, gone to the closet, and felt nothing. I slowly closed the door, and kept my male clothes on, and got really depressed. Why? I don’t know. Two days went by, still the same result. Did Jesse leave? Did she abandon her life and move on? This has happened only twice in the 17 years I have been crossdressing. I began to get scared that  the thrill, the feeling, the female inside me was dying.  The more I mulled it over, the worse I felt. I guess the point I’m trying to make is I think sometimes you go as far as you can go in your personal life with your Fem side, and then you hit That Brick Wall as I have. I have all the pretty things I need to dress, have been out in public several times, SO… what’s next?

I guess I will have to wait for that answer. Life has it’s ups and downs, and I guess this just one of those hurdles I must jump over.  Thank goodness Jesse has returned in my heart for now, and we will continue the journey.


Transgender Heaven - Gender Journey


  1. Monika Sweet 3 years ago

    You are not hitting a wall about being a woman… But you have been doing something so much as a routine that you have lost the excitement of it.

    I went thru this once when my wife was gone for a month. I would come back home every evening and doll myself up with the clothes and dressed that I did not use for long time or the new ones. After 14-15 days, I exhausted all the available options… Then wearing the same look again was less rewarding (law of diminishing returns)… So, one day when I was all dressed up and felt very comfy, I needed to go down to buy some items. Without realizing that I am dressed up, I just grabbed the key and my wallet and went out. Only when I entered the elevator and I saw a reflection of myself in the mirror, I realized that WTF… I am still dressed and there were people in the elevator… I was flush and confused and nervous not knowing what to do.. But the elevator reached the ground floor and I was out in open in daylight. So I just went ahead and picked up the stuff quickly that I wanted to buy and came back home panting… When I got my nerve back, I realized what have I just done.

    The whole episode was so thrilling and exciting that it immediately gave me a motivation to dress up and walk around a bit instead of just lying on couch and watch TV.

    Sweetie, it’s the new things, those small changes that you may need to bring in to keep your motivation to be the woman. Just pick up the laptop, turn on the webcam and talk to people… You will long for the those moments gain the next day you are in the office.

    • Jillian Simpson 3 years ago

      Monika I love that story. One morning I was working out in yoga pants and sports bra and I head the doorbell ring. I was the only one at home so without thinking I run out of the gym in my basement and answer the door and it was the UPS delivery man. He just smiled and had me sign for the package. As I shut the door, I realized what had just happened and felt like I was going to faint. I just sat there wondering what he was thinking as he made more deliveries that day.

  2. facily 3 years ago

    i like this site very much i hope i have sweet things from your site every day

  3. Ashleigh 3 years ago

    Thanks for sharing and for your honesty. I have also come to those “brick walls” with Ashleigh. I learned long ago not to purge, as this too shall pass. The apathetic feeling has always gone away. During those times I have always felt Ashleigh’s presence, even if not as strong. She is a part of me as much as her male counterpart is.
    We allow society to determine right from wrong when it comes to clothes, and as such we experience feelings of guilt that can hamper what is supposed to be, and is, a fun experience.

  4. Lyta 3 years ago

    I hit that darned wall again a couple of months ago and currently I am very depressed and frustrated. For almost a year before I was seriously stretching my comfort zone, telling two people, mixing in parts of Lyta in my daily appearance… And then, suddenly, it all just felt awkward, being “different” all the time was taking its toll, I stopped it all just needing to be “normal” again. I hope I will get out of this low again, like you all say we do — but right now it feels kind of hopeless.

  5. Amanda Patrick 3 years ago

    Hi Jesse

    This definitely ebbs & flows I will under dress for a couple of weeks swearing to at least keep under dressing. I have purchased things for my self in stores and enjoyed dressing time in private and then suddenly out of no where my mood changes about it all and I stop for awhile even though I have plenty of time and opportunity to dress. Jane S is right when she says moods effect every thing in our lives but one thing is for sure those desires will return usually stronger than the last time .don’t worry it wont be gone for long I can feel mine wanted to be satisfied again already.


  6. Sylvia 3 years ago

    Isn’t it perfectly normal to loose the feeling of excitement when dressing up? I asked myself that question when I experienced it myself. The further I go with my crossdressing the more ‘normal’ it becomes. I can hardly imagine that a girl is filled with excitement every day when she puts her clothes on to go to work. It’s just part of everyday routine. Now that I go out in public more and more it becomes more and more normal to me. I guess once you’ve reached the point that your crossdressing no longer restricts you in what your doing you actually arrived at a point where it’s no longer special but became normal. Just like every women we will still feel excitement when we dress up for a party or special event at which we can celebrate our femininity. But when you’ve reached the point that putting your clothes on for a ordinary day of work or doing groceries is just as exciting as it sounds, well, congratulations, you’ve become a women!

  7. Sylvia Schmidt 2 years ago

    Jesse, thank you for that very honest account. As others have said, feelings come and go. What I’m still trying to learn is that I am Sylvia, regardless of whether I feel Sylvia or the need to express herself at a moment. Your description and the many replies underscore my conclusion that I am not just dealing with a fetish or an acquired habit, but with something that is real within me.
    Wishing you well,
    with a hug and a quick peck on your cheek,

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