Crossdressing is fun

Is it just me or do we, us girls, seem to focus on the negative aspects and emotions of crossdressing? I say crossdressing should be, no must, be fun..otherwise why do it?

Okay I know immediately I’ll get thirty posts saying ‘yes but I have to dress in secret’….’my wife/girlfriend/boyfriend will never accept it’….’I feel so alone/depressed/rejected…(add in your own words)’. …and yes if your circumstances conflict with your desire to express as a woman, I agree crossdressing can seem like anything but fun.

However consider these alternate views.

Crossdressing opens up new ways of appreciating the world allowing us to see the feminine perspectives that most men just cannot understand. We can empathise, sympathise and appreciate being a woman.

Crossdressing allows us to become somebody else, just for while, relieving the social stresses associated with being male. It can change and soften our posture, voice and behaviour….which are often appealing to our partners.

Crossdressing should be fun, enjoyable, satisfying and if possible shared. As adults we often lose the ability to play….crossdressing must incorporate that sense of play.

Women’s clothes are just so much more interesting than most men’s fashions. We, as women can change our character by changing our clothes, smart business woman, sexy temptress, pretty princess….all are just a dress away.

Crossdressing creates a sense of ‘event’ in our lives, introduces risk balanced by excitement, missing from many of the grey suited commuters drifting home of an evening.

Crossdressing excites me as much today as my first time staring into the mirror in my sisters bedroom in 1969….the pink frilly pants, little tasseled cow girl skirt….and so each time retains some of that innocent excitement.

The objection of many partners is not the crossdressing, which can actually allow them to live out their own fantasies but it is the dishonesty and lies that often accompany the secretive nature of crossdressing which is the underlying problem.

Crossdressing is more widely understood today then ever before…NO we are not there yet but that’s as much because we, ourselves retain the secrecy.

So girls…come on lets be positive….put on that little black dress, the highest heels that you can safely walk in (always do a risk assessment first) and lets be proud that we are crossdressers….men who just love to wear a dress.

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Profile photo of Catie Maye
I first dressed in my sisters cowgirl outfit at 9 yrs old and knew cross dressing would always be part of me. Now 46 yrs later I live in Milton Keynes, UK sharing my life ....and my clothes with a beautiful woman. I dress openly, have written a book on cross dressing and in 2015, appeared on TV as Catie. The journey is difficult, but if you can, embrace it.
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  1. Profile photo of
    Rosaliy Lynne 1 year ago

    I agree with you, Catie. Dressing can and should be fun. Of course we all start out thinking it is a bad thing based on how we were raised. Then there is the pressure to marry and raise a family and acquire all that society would have us believe makes for happiness and success.

    All that is just window dressing and helps us hide from ourselves. For me it started out one day when I knew “I had to dress as a girl” and set out to do so. Initially, as probably all of us did, in secret. And it was always fun to shift from boy to girl and back again. In the long run I felt RIGHT as a girl and dressing was part of my life through 3 marriages. Only one wife knew and, at first, enjoyed it with me but that changed and she didn’t even want me much less me dressed.

    I have grown into the woman I am today and happily dressing all the time. Even got my name changed and my gender as well (though without surgery).

    For those who dress part time, the majority of us, remember this is an important part of you and somewhere along the line, you need to out yourself to your partner, preferably before you spend years of marriage dressing in secret and get found out. The damage to trust can be a disaster and often is.

    Relationships are built on like, interests and mutual respect. Honesty and communication are also foundations of a lasting relationship. Ok, it can be scary to come out to that loved one, be it a family member or a perspective partner. There is a fear of loss and that makes us all wary. In many cases we do lose after. I have also learned that there are many whose relationships survive and grow with that knowledge.

    Dressing up, even part time, should be fun and can be with the proper support but it has to start with both of you knowing each other. Your femme side is as important as your masculine side and is part of the WHOLE you. If you can’t be whole in your relationship there could be problems ahead.

    Think about that and then try to start conversations to see what your family, spouse, whomever, think about cross dressing in general. If you feel positive, move a little closer to revealing that side of you.

    When my last marriage dissolved I resolved that any future relationship would include knowing all about me or else I would keep quiet and enjoy what friendship could bring.

    Look at it this way – if there is no room for ALL of you in someone’s life, half of you probably won’t fit either.

    • Profile photo of stacey  s
      stacey s 1 year ago

      Hi Girls, Yes crossdressing is fun and exciting and should always be !

      Stacey S

  2. Profile photo of Grace
    Grace 1 year ago

    I agree, cross dressing for me is fun and still very exciting. I simply try not to think too much, just enjoy!

  3. Profile photo of Monika Sweet
    Monika Sweet 1 year ago

    Today, I plan to take a day off just to enjoy my crossdressing. My wife will be away with friends and it will allow me to dress up more freely and maybe I will be able to sneak out just for a short walk in the parking lot in my new heels and dress.

    The thought itself has excited me enuff and got already started by waxing my legs and body… I already have a dress in my mind and I am just too restless to get going. My heart beats faster even of thinking to apply the makeup and lipstick and the new lingerie… How would it feel against my bare skin… All these thoughts just makes me so anxious… In a good way.

    I will post photos later and let you know if it went well.

    Hugs.. XOXO

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

    Well said Catie! I can speak from personal experience that NOT telling your spouse does indeed lead to a lack of trust-even if the reason for not telling was because you honestly believed he desires would disappear after getting married!

  5. Sara Thomas 1 year ago

    I love the article very much and so very true. We need to be the pioneers pave the road For are Sisters in the future.
    People are always judgemental something new and different.
    But the more we go out as a woman we would be more accepted.
    I’ve been out many times dressed up all the way heels makeup nice dress but a lot of times from doing housework and I need something at the corner store I will go casual.
    Most of the time people really don’t care.
    Be yourself be happy doing it the more you do the more your acceptance

  6. Jamie 1 year ago

    I agree with you so much I have more fun and excitement just dressing up and doing makeup and going shopping in girl mode.So get out and enjoy life.

  7. Profile photo of JENNIFER
    JENNIFER 1 year ago

    I definitely agree that crossdressing is So Great!! Women ‘won’ their Sexual Freedom’ back in the 1970’s, but as men we’ve NEVER gotten those same freedoms. And now, when anyone mentions the word ‘Cross Dresser’, the term refers to males, period. You never hear of female ‘cross dressers’ because it is ‘acceptable’ that females can wear any article of clothing, male or female, without anyone giving them a second glance. I’ve loved ladies lingerie since my early teens. I had 6 brothers, one 8 years older and the rest all younger before getting a sister(10 years younger than me). So I loved looing at Mom’s mail-order catalogs that she got regularly, Sears, Montgomery Wards, etc. I always wanted to see the sections with pretty lingerie, teen girl’s panties, bras, slips, gartered panties, nighties & foundation wear, as well as all the lingerie for young adult girls & women. I was especially interested in the nylon panties, which from the mid 40’s to the mid 60’s, was primarily “High Waist Full Brief Nylon Panties”, often with lace trim. When I had to babysit my younger bros & sister, when I put them to bed, I’d go into my mother’s bedroom and open her lingerie drawer and get out a pair of her silky white nylon briefs, at first to feel, then to wear. And after that, I WAS HOOKED, the silky feel of all her underwear, most with lovely lace trim…I wanted to wear those kinds of underwear, not all the scratchy briefs that boys wore. See, I was born in 1950 when all the girls and ladies wore gorgeous silky lingerie and that’s what I’ve always wanted to wear and now at 66 yrs. old, I do. Since 2008, I’ve gotten my wife to ‘accept, barely’ me wearing lingerie around the house, 24/7. (Also, since 2002, she doesn’t want anymore sex, which is very hard cause I still quite horny with masturbation as my only ‘relief’, but it’s Still Not The Same!~!!!! So I enjoy wearing lingerie all my myself, having no friends or a car(totaled 2014), and going ‘online’ for comfort from others…

    • esther22 1 year ago

      I had a similar experience as you in that my wife no longer wanted sex, so in searching the net, I found that I needed to suppress my male hormones to quench my sex desire. So in taking the natural female hormones, I found that the 1st thing that happened was a desire to wear womens clothes. So when she was gone, I tried on her slips & skirts which IMMEDIATELY made me not want to wear pants again. I did wear pants again but only because I HAD to. As I refused to take off the slip, my wife found out about it, but when I told her how comfortable it was, she not only gave me that slip, but bought me another one. But she did make me promise not to wear skirts in our hometown in public. So the door is open for me to wear skirts sometime. What I REALLY like about skirts is that I can wear several on top of each other in the winter. I cant do that with pants. Esther

  8. Profile photo of Catie Maye Author
    Catie Maye 1 year ago

    Hi …thank you for all the positive feedback…I write what I feel….I know that sometimes its hard for others who have a much tougher life…but if this is how we are born…accept it, enjoy it and try to find as much peace and happiness as you can.

    We are a community…. sisters and we must find the time to help those who struggle with the challenges of a cross dressing life. …let them know that they are not alone…cross dressing can and should be embraced…sorry got a bit carried away….but you know what I mean….thank you for your support. Catie xx

  9. Profile photo of Lauren P.
    Lauren P. 1 year ago

    Wonderfully written article Catie! I absolutely LOVE the positive spin you put on it all! It’s so refreshing to read something like this and be reminded of all the good that surrounds life as a crossdresser. The advice from Grace is also spot on … try not to think too much and just enjoy!!

    <3 Lauren

  10. Jeanette 1 year ago

    Yes yes yes , it should be fun, there are some who take Crossdressing so serious that all enjoyment seems to be stripped away. As well as day wear, evening wear and varieties of under wear (never enough)
    I have several dresses/costumes just for fun, Saloon Girl, Square Dance outfit, Nurse dress and apron (60s style) and of course the French Maid all bought on the internet just for fun, love it.
    Rosaliy Lynne you make a lot of good points. Your letter is the kind of advice that should be read and re-read then passed on to others who are struggling in the dark places we sometimes find ourselves in life.

  11. Profile photo of Alicia Roxxx
    Alicia Roxxx 1 year ago

    i love it

  12. Profile photo of Patty Phose
    Patty Phose 1 year ago

    I began wearing stockings and pantyhose at 4. Then at 17 I wore pantyhose out openly with short denim. At 18 I dressed fully fem for a college Halloween party.I got a lot of looks, compliments and questions about my outfit.

    To top it off I won “sexiest costume” and “best legs”. I loved being a girl and feeling girl power. It was more fun than I could have imagined. I bought a lot more clothes, went out dressed at every opportunity and pantyhose, heels, dress, skirt or lingerie became my everyday attire at home.

    I love being a cross dresser. The clothes are so wonderful and fun to wear.

    • Profile photo of
      Kim Cummings 6 months ago

      Ohhh, YES! I’M SO MUCH INTO MY WEARING MY PANTYHOSE AND HIGH HEELS! Initially, I started with my mother’s pantyhose and panties. My older sister also. We have all probably have started this way. The first time I tryed the pantyhose on ,I KNEW I would be wearing them always. The smooth and silky pantyhose over my freshly shaved legs were so sensuously sexy and absolutely lovely! I love the way they look and feel. I prefer Wolford’s tights, neon 40’s. They shimmer and are so sexy and absolutely lovely!

  13. Profile photo of Joanne
    Joanne 1 year ago

    Hi Girls, Embrace, enjoy and live every opportunity you have even, if it is only a short one.


  14. Profile photo of
    Breeann Jacobs 1 year ago

    I cant agree more girl, it’s a thrill to dress and do makeup hair etc I love the feeling of being a woman stay positive girls and don’t be hard on yourself life is too short


  15. Profile photo of Jamies time
    Jamies time 1 year ago

    It will always be fun for me I enjoy buying clothes at stores and going to beauty salons.I have found what makes me happy when I shave just like a woman.

  16. Profile photo of Leonara
    Leonara 12 months ago

    I am so glad that I am part of this community…reading about what makes us feel like ladies is truly an inspiration. Thank you all for sharing.

  17. Profile photo of debbie
    debbie 11 months ago

    thanks catie for a wonderful post. I cant imagine my life without debbie my alter ego

  18. Profile photo of Corey Parker
    Corey Parker 11 months ago

    I completely agree with everything you said.

    But as a long time CD, who’s in a committed, 25 year relationship with another guy, who’s gay, here’s my question:

    Everyone says one should share their secret with their SO. It’s not the crossdressing that bothers our SO, it’s the lying and covering up.

    But what if…what if it IS the crossdressing? In my case, my husband knows I dress up when he’s not home. But the unspoken rule is “Do what you want when I’m not home. But when I am home, I don’t want to see it. You cannot wear lingerie, nightgowns, silk, satin, especially panties in my presence.” Remember, that’s an unspoken rule.

    When I try to bring it up, he sighs, looks away, stops paying attention and says he doesn’t want to talk about it.

    If he knew the truth, that I’ve discovered I’m really a woman. I have no desire to surgically alter my body. I like my boy parts. But on the inside, I am woman, hear me cry.

    Don’t say “Leave him.” or “you should do what you want. Damn the consequences. HE is the one who needs to get comfortable with it.

    Don’t say that; he won’t ever be okay with it. And even so, I don’t want him to “tolerate” my femme self. I want him to “accept”, maybe even one day “celebrate!”

    It’s not that easy to throw away a 25 year relationship. But it isn’t the hiding and lying. He’s fine with that. It’s the truth… he does not want to hear.

  19. Profile photo of Catie Maye Author
    Catie Maye 11 months ago

    Hi Corey…thank you for taking the time to comment.

    Invariably each one of us lives a different life, with our different partners…different hopes and expectations…and I’m afraid there is no one magic answer.

    My personal opinion is that the strongest relationships survive primarily on love….but also on honesty, respect and usually a good deal of compromise.

    You say he’s the one that must get ‘comfortable with it’ but how will the situation change if the subject is never discussed. You say it yourself …its the truth he cannot accept but unfortunately the truth never changes…….. it remains a truth.

    It would be fantastic if you can find a way to engage him in discussing why he is so against what you want to be but if this is not possible then I guess its about finding a way for you to be who you want to be……separate to and remote from your relationship with him….in effect two parallel lives.

    I hope you two can find a way to make it work.

    Catie x

  20. Profile photo of Marilee
    Marilee 9 months ago

    IREPLYING love to crossdress and be all that is feminine . Makeup, nails, being a woman. Feels so good to be a girl. Wish I could do it full time. I would if I could that’s for sure.

  21. Profile photo of Jackieruss
    Jackieruss 8 months ago

    Hi all I’m jackie. New here or anywhere for that matter. Only sent one other post so I never told anyone but my xwife new an bought me lot of sexy stuff. And my wife now knows and buys me lot of fun stuff. She knows my taste in lingerie. She helps me in it, and have hot sexy sex . It turns her on to. I sometimes wear something under my male clotheslave when I’m out in public.
    Today I got a sexy teddy at a thrift store and rushed home to dressup. Now I have my bra,pantie, nylons, and new black w/white lace trim on . Shave my self clean. Mmm nice I took pictures and hide em . Now I’ve got a big lump in my panties. So better go tend to it. YES crossdressing is so much FUN. Bye all.

  22. Holly 7 months ago

    I just love looking beautiful and feeling sexy when I dress nothing else matters when I put my bra and pantys on

  23. Profile photo of
    becca 7 months ago

    It is always fun for me. Really it is very exciting. As has been mentioned, we become someone other than ourselves. We step out of our own persona. I love the transformation. Yesterday, I put on my panties, tights, leotard, a lingerie top, pearls, a gold necklace, and some lipstick. Becca can have bling. 🙂

  24. Profile photo of carrie
    carrie 7 months ago

    I love wearing my sexy little niteys panties and stockings,i feel so femme,and naughty

  25. Profile photo of Jackieruss
    Jackieruss 6 months ago

    Its me again. Im sitting here reading the post an articles on site and became aroused. I think ill go get into something more comfortable. I like to dress up in lingerie. Gets me so hot.
    Just have fun an enjoy the sexy things in life

  26. Profile photo of
    Paula Antoinette 6 months ago

    Hi!!!!I started off young too…just loved trying on my sisters underwear,putting on her sexiest little dresses and sliding into her really comfortable bed,lucky I never fell asleep in it!I always wonder though,if she knew..noticed her sheets weren’t quite perfect and a little dirtier I haven’t done a great deal since..purchased the occasional pair of hold ups,charity shop dresses etc just need more confidence x

  27. Profile photo of
    Kim Cummings 6 months ago

    Cross dressing is a very erotic sensuously sexy fun and exciting time. The transformation of my personal look to the new feminine looking me is a experience one has to try to get the best results. The makeup is difficult but it takes time. Hair removal is easy once you have removed the ugly hair from your legs. Depilitorys especially keep the hair from growing back so quickly. Shaving my face is the most difficult thing to do. I can recommend laser hair removal, but it is costly. No matter what, I am always nicking my face.

  28. Profile photo of
    Kim Cummings 6 months ago

    Makeup is a very nice touch if you are amenable to try to master the art. It is quite time consuming and removing your makeup completely is a issue. Mascara is difficult to remove so I use a clear kind. Lip gloss is probably the best way to go. Your lips will be too dark if you use a darker shade.

  29. Profile photo of
    Stefanie 5 months ago

    When the guilt and shame is removed
    It is fun
    If yiu can share it and it is accepted then even more fun
    Its very erotic
    Creates incredible fantasies and can lead to great sex
    Yes lots of Fun!

  30. Profile photo of
    Kim Cummings 5 months ago

    The eroticism and exciting times in the world of wearing my own pretty feminine outfits is a great way to express your inner feelings of the tactile sensational fabrics that before weren’t for men. The inner workings of the psychology of the person who you are is the way your ideas and suggestions periodically come to the fruition that we are together and can be open about this topic. The wearing of these things are not abnormal, but it is a issue of the identity of the sensuous feminine looking person who is not uncomfortable with the new relationship between you and your pleasure of the sensuous feminine outfits and the smooth feeling of our sexy lingerie.

  31. Kim Cummings 5 months ago

    Unisex apparel is upon us. We have a difference in the glitter, and the glamor the universally accepted “norms”.
    For example : Is the color of the garment too loud or too garish? Does it fit too tight? Is the fabric synthetic? -nylon, is used in a number of ways. And if it is pink, well maybe your necktie,
    Remember velour? I do. It was very popular with many different folks. Soft, comfy, much like velvet. Other features include your size, your tastes, and the proportions of the idea that the look of your occasion is suited for. Why do men’s pants require only black, khaki, navy, and little else?

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

    My first dress was my older sister’s Girl Scout uniform. Back when they actually had a uniform dress. When I added pantyhose to the outfit I was hooked from then on. It is a great source of stress and stress relief all at the same time.

    I look forward to the day I find an understanding woman with whom I can share this side of me.

    • Profile photo of Catie Maye Author
      Catie Maye 2 months ago

      Hi Terry

      Partners are difficult to find typically because of a lack of understanding about what cross dressing means….and more importantly most partners including mine fear where it will lead. As difficult as it is….be open, be honest, explain….if its the right person for you they will understand.

      Catie xx

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