This thing (whatever crossdressing is to me) has been nothing but a burden. When combined with the added stress from all of the years I’ve been avoiding it, I’ve reached a point where I finally need to deal with it.

I have read many articles on ways to stop the urge to dress, but mostly found them to be sexist and ridiculous. A few come from a more religious view, damning someone worse for their clothing choices than murder, which just seems ludicrous. After reading through countless articles, I can honestly say that those that dress regularly seem far saner to me than those in denial (or at the very least they are happier.)

So here I am, about a year into this journey, and I haven’t done much of anything but worry myself sick. I ask myself countless questions without even looking for answers. Although I’m fairly new to this site, and I haven’t really been active, I have decided to reach out to all of you, this community.

Unleash Your Inner Woman

I choose to remain anonymous and not explain my life, because that simply doesn’t matter… However, reaching out does matter in my personal search for answers (especially if the thought process I am sharing is relatable to anyone else in need of help.)

I have a few supportive friends (including my roommates). The way I told my roommates (a male and a female) was almost more like issuing a warning. I told them individually that I’m not sure how far I’ll go, but I can’t stress myself out worrying about hiding everything (from small stuff like mail to more obvious things such as deciding to shave my legs).

I was fortunate in that both of they were very supportive and chose to recognize me as the friend I’ve been. They supported me by claiming that this doesn’t change anything. When I told them I would get it if they moved out, he laughed and she expressed sadness that I didn’t feel comfortable talking to her sooner.

This has reduced so many worries; I recommend to anyone wanting to experiment with anything to share it with your more accepting friends! They remind you error is part of “trial and error,” and that it’s OK to have some bumps along the way. I feel very lucky, but I think that’s just kind of how friendship works.

With all of my friends’ support, and my own determination, I have a huge problem… I haven’t really accepted myself. This is why I’m even writing this article. I have so many fears, a lack of information, and I am stuck in this state of ambivalence. So I ask all of you, a community full of wisdom that shares such similar experiences all based around the same topic… How do I proceed? What does it take to accept this aspect of yourself?

To get over my fears I want to just dive right in! This is a challenge, though…

-I haven’t dressed in several years, although the urges never stopped.

-I am poor, and I’m not willing to shop offline (yet).

-I have no confidence; I am scared.

-I am not sure of any preferences (or my size… I need a cheap way to figure out what I like and how things fit).

-I know nothing about style/fashion.

I don’t know where to start, and I am much too stubborn to borrow anything. My goal can be broken down into two things:

  1. A better sense of understanding as to how important, or what, crossdressing is to me.
  2. To learn how to have fun with it and not be so ashamed…

I have finally learned that this is something that doesn’t just go away. I’m not sure what other goals I need at the moment, how far my interests will take me, or even why I’m doing this. And yet… I have decided that I am doing this and it’s time to figure it all out. I appreciate any tips, or advice, and the time you’ve taken to read this.

(Also, I get the whole “take as much time as you need” thing. Honestly, though, if I don’t just jump in, nothing will change… Something has to change, and with as much caution as I’ve been taking, I don’t think I will be doing anything I’m uncomfortable with.)

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20 Comments
  1. Stephanie 2 months ago

    I thought I could quit crossdress also. And I did many many times. I got caught by my wife and told her I wouldn’t do it anymore. Time after time after time. So the last time I got caught I just said to her, honey, I love you and I’m the same person I was yesterday and the day before that and even the day we got married. Of course, she wasn’t aware I was underdressed until a little later that night. Her maid of honor knew I was a “little different” as I was growing up. (She lived next door and knew my sisters as well) As you stated you are poor, I grew up rich! Had no money, but had clothes from 3 sisters to choose from! Bras, panties, nylons and garter belts. Plain dresses, fancy dresses, and the best were the prom dresses. As I get older and was caught numerous times by my sisters, it was easier and easier to dress to my hearts content. Until middle school. Had to wear ugly BVD’s and ugly white socks. Especially on Phy Ed days. Couldn’t get home fast enough after school. And then my sisters were going off to college and taking their clothes with them. I then discovered that resale shops don’t care if you are buying a pair of used football cleats, of a frilly little light blue bra. As long as you bought something, it didn’t matter. Fast forward a few years, had my drivers license, a part time job, a car and a girlfriend. And access to the finer stores. J C Penny, Boston Store……..I loved to shop at Penny’s because I befriended an older sales lady who helped me find things I never knew I wanted. Until she showed me them. All through this time, I quit dressing. Like I said, again and again and again. I finally got my wife to accept my dressing after we had been married for 15 years. She gave me 45 years of her life, and even though she wasn’t happy with me at first, we had no major problems after that. She could even tell when I was underdressed because she could see it in my face. I was always more calm whenever I underdressed. I sort of rambled on a little, but what I’m trying to say is, if you can quit dressing, good for you! And if you can’t, good for you! Embrace it. Let people know, but slowly. Different hair style, a little eye make up. Maybe a pretty little blouse with just a touch of lace. Enjoy it, because it so hard to quit, over and over and over again.

  2. Brandy Chatte 2 months ago

    I have tried quiting countless times, the last time I purged all my clothes shoes, toys makeup everything… It lasted nearly a year and then the temptation just became to big, sad and angry and excited at the same time, now i miss my shoes and clothes and makeup, and battling to replace the items, especially the shoes, Oh how I miss my shoes….. What have I learned, it costs money to replace all the stuff every time you have a spate of feeling bad or whatever it is…. so now, where to, no idea, time will tell, maybe I find some local friends, who knows…

  3. Missie Fem 2 months ago

    If your female roommate is accepting ask her about helping you determine clothing size. Could be a lot of girl friends time. If your uncomfortable with that then go to amazon do a search for female clothes. Generally there will be a chart that uses body measurements to determine sizes. Pick a brand name product and not an Asian site. The later is not as reliable in US sizing ( runs a lot smaller). Once you have sizes try shopping at a second hand store to get clothes in you size. Point is to get a small select to see if sizes fit. Then you can go after the things you really want to wear! Hope this helps!
    Luv
    Missie

  4. Author
    Nameless One 2 months ago

    I appreciate all of the responses to this. It seems clear that the general response has been, “go shopping!” Sometimes the simple answers are overlooked? I think I should take all of your advice, and do just that. However, (since I am in the limelight) I was wondering if I could get more advice on self acceptance? I feel like a majority of this site had to deal with this issue, regardless of the acceptance of others… and I could really use some advice.

    • Berta 2 months ago

      Nameless One,
      Like you I am relatively new to this site and how it works. Unlike you I am approaching the “sunset” of my life at age, as of April, 2019, 79. I have been a closeted crossdresser for the last 40 years of my life! I know just what you’re asking as the unjust guilt and shame we put on ourselves is hard to live with. How and why I resumed my feminine needs and passions is a story for another time and I’ve shared it many times around the web already. (I only use 2 femme names, Berta and Berta_Gal.) My wife hates the idea of my feminine love of “dressing” which is mostly satin lingerie and nightgowns. I wear satin hi cut briefs or boxer style tap panties every day.

      Now here’s how I reached this point of dressing. Years ago there were some excellent chat rooms on the web, Microsoft’s Crossdresser chat room was my favorite and I had many, all now lost to me, helpful “sisters” in that chat room. I will always remember the night we were joined by a Minister/Preacher and a MD, Medical Doctor, who both were finding there way in the crossdressing life. When both these professionals shared with all who were in the chat room that there was no reason for us to be dragged down by guilt feelings, we were shocked. The MD explained that we are what we are and there is absolutely NOTHING that can be done to change that!! When we are in our mother’s womb we are all female at first, as we are developing some get the proper amount of testosterone from their mother and become a male child. Normally those who don’t remain female gender and are born girls. But, there is always a but, through some processes known only to God some get short changed while in the womb. Some of these births result in the child having the looks of one gender but the “plumbing” of either both genders or the opposite gender. Lastly is our category where we are born males but are, in my opinion, wonderfully blessed with stronger feminine genes than masculine. While I can’t speak for the others in that chat I can share that it was like a 1,000 pound weight had left my body!! I’ve used the comment the MD shared over and over again; “we are what we are and that can NEVER BE CHANGED!!!”

      Some seem to have forgotten that Jesus and his disciples all wore robes with flowing skirts and men still do in the old countries. Since that revelation I do my thing around our house. I’ve never been “out” as Berta and don’t ever expect to be. I hope this will be of some help to you and I wish you all the best as you begin your climb up your mountain of feminine discovery.

      Berta 6/13/2019 6:03 PM EDT

  5. Lucinda Hawkns 2 months ago

    great post, i have dealt with my x dressing for many years hiding it. now in my 50s my wife found out and lets me dress up when our last adult child is not home. she still does not know why i dress up, neither do i i gave up wondering y? its part of me and that’s all that matters to me. i feel happy when i am dressed up as a female for lots of reason, panic attacks, depression, anxiety, stress. being the person i should of been when born. for i have a feminine figure. i have more female cloths then wife and seem to wear them more then she does. i am medically retired so i have time on my hands to do the things i like to do besides ride motor cycle and ride with groups for a good cause, enjoy the county living in war saw N.Y soon. most of all is dressing up pretty and being happy and free

  6. Angela Kearney 2 months ago

    Nameless one; I hope this helps:

    First, realize that you are on a journey that you did not choose. I can tell you that I did not choose to be a cross dresser. Basically, it chose me. Understanding that you are in a situation not of your choosing is freeing when you come to terms that is the case. Also, spend some time identify what power this gives me that other people don’t have? It gives me a greater appreciation for what hard work really goes into making someone’s outward appearance beautiful. It also has provided me the realization that makeup and time can align the person who you envision in your mind to be who you see in the mirror. Many other gifts await you on your journey. As you progress through your journey you will find the ability to look at things much more completely with a vast wider perspective. You will find yourself more empowered in many situations because as you come to embrace your gift, you will begin to appreciate your ability to see the big picture in all you do. All of this cost time, introspection, and good friendships. Your lack of financial wealth is not a limiting factor you have communicated that you have all that need for the journey. You will find that your life will change, but change is inevitable. Just embrace the change and enjoy the ride. We all are on the journey with you. Some of us a farther down the road and some of us are just starting. The point is that we are together.

  7. Jessica Rabbit 2 months ago

    They say ‘change what you can and accept what you cant’ this would be one of the things that you can’t change, so embrace it. I tried fighting it for years and it didn’t work, glad you seem smarter then I was honey.
    I think most of our shame about this comes from old fashioned ideas and misunderstanding, but times are changing (at least it is here in the UK) . It wasn’t so long ago that homosexuality was a prisonable offence, and there was also a time that a woman who dressed in trousers would have been scandalous. Now both of these things are acceptable in public. I think the more of us that can be open about this the quicker change can come, also shows like Ru Paul’s drag race helps people warm up to the idea, it’s all going to be a matter of exposure. Not that I’m trying to enlist you into anything, this is your life and you should only go as far as you feel comfortable, and don’t let anyone tell you differently.
    As for clothing, it’s going to be a matter of personal taste, but I would go for just a few classic versatile items that you can mix & match and dress up with accessories. Maybe you can throw in the odd guy shirt/t-shirt as well, cis girls do.
    I don’t have much money to spend on this, so I used rice to make false boobs (check out ‘rice sizers’ to see how to do this), I soooo love the feel of the weight in my bra. I don’t have a wig yet, I may get one, I may not, its personal choice. Supermarket clothing is cheap, but any girly stuff I want, I just go in like I’m buying a present for my wife for her birthday. This was how I brought my first makeup, a complete set for doing eyes. The sales woman was so helpful and answered any questions that I had and made suggestions, but this sadly was lost in the last purge .
    Treat this like its something normal, because you know what honey, to us it is, and soon the rest of the world will catch up.
    Jessica x

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