One reason I joined this site was that I feel I need to write about some things. There are things that my wife really can’t fully underdstand. Granted she has known that I am a crossdresser since day 1, and that was 8 years ago, when it really comes down to it only another crossdresser could possibly understand.

I am not looking for answers really but just kinda “talking out loud” and if someone reads it and/or replies than great.

I started working from home about 2 years ago as a web developer so that has given me the opportunity to dress every day. I will get out of the shower and go pick out my outfit. I will then wear that outfit until no less than 6pm. In the past I would try to only buy womens clothing that would be considered sexy… not something you would wear to work. And I think I did that as a way of dealing with crossdressing by telling myself that I was dressing purely for the sexual thrill and not because dressing was a part of me. But in the last 2 years i find that i am buying clothing that even my mother would wear… like long dresses and skirts, 2″ heels instead of 3″+.

Added to my changing attitude about what I should wear is the fact that not long ago I told my mother that i am a crossdresser. It wasnt that I could go either way, tell her or not tell her, it was that I have to do it… she must know. After, I thought to myself “why did I tell her?”… “what did I gain from doing so?” I couldnt and still cant find in myself any reason for telling her but I had to do it. To my suprise, it was no suprise to her… she told me although she had never seen me in womens clothes, she knew.

What does all this mean.. I dont really know…

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Profile photo of Paula Ann Wilson

Paula Ann Wilson

40 Something non-passable crossdresser. I have an amazing women as my partner who has known that I dress since day !
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  1. Profile photo of JaneS
    JaneS 1 year ago

    Those who’ve never experienced it can rarely understand how deep the need to cross dress is. In essence, it’s more a choice of what to wear rather than to wear or not.

    Having the support of loved ones is also invaluable and thankfully becoming more common and society becomes more exposed to transgender people.

    Thank you for finding that ‘something’ to write about.

    • Profile photo of Paula Ann Wilson Author
      Paula Ann Wilson 1 year ago

      ” In essence, it’s more a choice of what to wear rather than to wear or not.”

      WOW… your statement is so incredibly true for me… probably for most I bet.

  2. Profile photo of MacKenzie Alexandra
    MacKenzie Alexandra 1 year ago

    Thanx for sharing. I have similar feelings. Whether I am dressing as a man or a woman, I prefer to be comfortable. That being said, most of my feminine wardrobe are everyday and casual wear. For me, it is about being true to who I am, and not meeting the definition of others. I too have a supportive spouse which has made this journey much easier, but I also wish I could disclose to my family. I do not like keeping such a secret from those for whom I care and love.

  3. Profile photo of Jessica Hiver
    Jessica Hiver 1 year ago

    Thanks for sharing, Paula. It sounds like you feel pretty comfortable with things as they are. Good for you. I am not able to share my cd with my SO at this point but it seems that must be quite liberating. Jessica

  4. Profile photo of Tammy
    Tammy 1 year ago

    Thanks for posting, Paula. I work at home too, and I am so glad to be able to wear what I want. Sort of like Mackenzie, though, my fashion style is so casual that I don’t think people notice when I’m wearing in public.

  5. Profile photo of skippy1965(Cynthia)
    skippy1965(Cynthia) 1 year ago

    Agree with Jane-I can’t NOT wear my femme clothes-it literally gives me severe anxiety when I can’t for any extended period of time. Love your story Paula!

  6. Profile photo of MaryJo
    MaryJo 1 year ago

    “In the past I would try to only buy womens clothing that would be considered sexy… not something you would wear to work.”

    I know what you mean. The majority of what I have is…well, kind of on the short side. I’m not so sure at this point i could feel comfortable going out in many of them. But they’re not so short that I haven’t seen other women out in similar ones; I guess it’s a matter of confidence.) I also have some long skirts and dresses that I love too.

    “I thought to myself “why did I tell her?”… “what did I gain from doing so?” I couldnt and still cant find in myself any reason for telling her but I had to do it.”

    It is wise to question why you should talk about something as sensitive, as not well-accepted by general society. Time goes in only one direction. Once something is revealed, it can’t really be taken back. So it’s safer to think a while before saying so, like you were saying, what the benefit is. If there really isn’t one, maybe it’s better to withold. But, as you have seen, it doesn’t have to be bad at all.

    “What does all this mean.. I dont really know”

    I wish I could help you with that one. I don’t know myself precisely why I do what I do. If you figure something out, could you help me understand too?

  7. Profile photo of Paula Ann Wilson Author
    Paula Ann Wilson 1 year ago

    Heres an update… my mom sent me some pictures in the mail of me when i was little, somewhere between 2 and 4… and guess what I was wearing? A dress! She sent a note along with the pictures saying that I would cry at times if she didnt put me a dress… but somewhere around 4 years old I stopped.

  8. Profile photo of Brenda_an
    Brenda_an 12 months ago

    Well Paula Ann, your fortunate that you have a way to earn money, and maintain a partner in a relationship (your wife).

    I suppose, the fact, that you are able to have an activity on the side (crossdressing) is a fringe benefit.

    I know some folks that are self employed…are proud of the fact, that they can sneak away to the golf course, pretty much when ever they wish.
    I guess you sneak away, into a role, to which, you prefer to be.
    No harm done. Enjoy.

    • Profile photo of Paula Ann Wilson Author
      Paula Ann Wilson 12 months ago

      I am fortunate to work at home… in the last 10 years I have worked at home, for myself, about 8 years total. I love the fact I can slip away and do what I like to do which is fly model airplanes… my photo area has a few images of me holding one of my current models.

      Paul Ann

  9. Profile photo of Codille Benton
    Codille Benton 12 months ago

    Paula Ann,

    I like you over the last few years have come home to work. My wife has know forever but my kids really only since Christmas. Originally it was all sexy clothing and sorry only 2″ heels but now I wear whatever feels right that day. Skirt and Blouse, ok, Business dress, no problem, new this year sweaters, and then I like you made a change that was like an evolution, jeans and t-shirts….when did that happen? I think we all evolve, now like you I am a chameleon I never thought would exist. You know, I am really good with it.

    Thank you for sharing your story Paula!

    Codille Benton
    Managing Ambassador

  10. Adelle 12 months ago

    I find shopping for clothes as a larger man to be a pain in the ass so my hat is off to you that can shop both ways.

  11. Jeanette 12 months ago

    To tell or not to tell ? I told my grown up children about my other self , I felt I had to, I didn’t want anyone else to tell them, I wanted them to hear it from me first with my explanation. They took it well at the time but as for the long term ? the jury is still out.
    Dressing at home and being careful not to upset my SO , she understands my needs and I must not overstep our arrangement.
    She likes my company as Jeanette, and adds to my wardrobe now and again in encouragement.
    I have several hangers with a compleat outfits ! this includes all underwear Bra,Knicks,Slip and or Petticoat, Tights or Hold Up Stockings in a bag with the outfit , the outfits are day wear, season day wear, (winter /summer etc.) evening wear, Ball gown, Classy Dresses plus fun wear (Saloon Girl/Nurse/Rock and Roll 50s Chick etc.)
    With each outfit compleat I can change without hunting through drawers etc. Looking for the right co ordinating ensemble.
    Do any of you girls do this ?

  12. Profile photo of Stephenie0111
    Stephenie0111 11 months ago

    Great job Paula
    I find myself buying mor and more casual woman’s clothing. They are sooo comfortable. Maybe I’m just getting old but I find them as appealing as my sexy outfits.
    Stef

  13. Profile photo of Terrie
    Terrie 4 months ago

    Paula
    Just want to say you look awesome in the picture if I looked as good as you I would go public with it no one would know not that you would care but you look stunning the only reason I don’t is I have hard time finding the clothing to fit I can’t even find a bra to fit me I’m a buddy builder and have thick chest I already have a nice set of muscle boobs like a medium fifteen yr old has but I’m fifty two around so it’s hard to find one lol I already wear panties I love them I wear them all the time confy they are lol but great story

  14. Profile photo of Terry Wright
    Terry Wright 3 months ago

    It is an interesting situation. I have stopped for different lengths of time, but in the end I always come back. I work from home, but have a roommate who has no idea. It was not until he started working in an office that I have been able to pursue dressing again.

    Today I spent most of the day at my desk in my new grey pleated skirt. It was so comfortable to sit there and work while also looking out the window on a nice spring day. I am certain that my wardrobe will continue to grow as long as I have the house to myself during the day. Lunch time is now online shopping time… looking for that new dress and some nice strappy heels to go with it.

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