What do you do to help your crossdressing?

What do you do to help your crossdressing?

Your typical male crossdresser will occasionally wear woman’s clothes. Perhaps a single article of clothing, such as pantyhose or a bra. Or perhaps he’ll go all out and get dressed up, even wearing makeup and a wig. Some of us go to the next level in our quest to…

Pass as a genetic woman

I felt I had to write that in large font. In my mind I hear those words echoing like the booming voice of a fake god on a cheesy television show. As if passing is a judgement we must face, a test we must pass or face the crossdressing shame of ridicule.

Okay, enough melodrama for one post. I was thinking about some woman who go further, perhaps permanently or semi-permanently altering their appearance. To put forth a more convincing feminine appearance, or perhaps to feel the luscious covering of feminine silkiness throughout the day.

Personally, I have pierced my ears, and have had laser hair removal on my face and most of my body. I used to wear my hair long, before my wife lovingly convinced me that she preferred to see me as a man every once in a while :) Same story with my nails, though to tell you the truth once they got much longer than a quarter inch it became tough to do everything things as easily. I get my eyebrows waxed on a fairly regular basis in a high arching feminine style, and make sure to moisturize regularly.

That’s a few of the things I do to go ‘above and beyond’. I don’t take hormones, which would probably help my femininity even more. I try to incorporate feminine movement and voice tips, such as those in this crossdressing how to, though I’m not as diligent as I could be.

What permanent or semi-permanent changes have you made to your body, voice or mannerisms to appear more feminine?

Which change were you most apprehensive about?

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  1. angie 3 years ago

    I just feel at ease wearing something feminine

  2. Rita 4 years ago

    Hi, I have an addiction to wear women’s clothes for as long as I can remember, I am now in my 30’s and married. Here is a brief description of my life, apologies if it is a little too details but it’s as it happened.
    I started off wearing my sister and mums clothes to fulfil my fantasies. Always ending up ejaculating into a nylon stocking, then stripping off after ejaculating because I felt ashamed and disgusted!
    Then When I went to college I moved away from home and started to buy my own stilettos, nylons, skirts etc especially pencil skirts, again each time ending up cuming and the same shame to follow.
    Later when I got a job I moved again but this time as luck would have it I moved into a house with 4 female house mates.
    At work I was in an office with 7 women so now I was always in the company of wemen all of the time. This also took its toll as it drove me further into my feminine side. To the point I began going for late night secret walks to near by estates all dressed up in heel skirts ect but not tarty just classy look. At the start I wore make up and a wig but later I got more brave I left the wig at home. Then arrived back at the house and climaxed, but in this case I developed a full on fetish ejaculate into each of my house mates shoes and and boots only stilettos in each case :-(. Between the four of then the had 157 pairs of stilettos boots, shoes and sandals. I am totally ashamed to say that I actually deposited into both lefts and rights of each in the time frame of just under 6 months.. I used to get do turned on when I would see them going out at night wearing the shoes the I came into, yea sick and perverted and I am so ashamed of that!
    I was dress size 14-16 and the four of them were 10-12 so I lost weight so I could wear their clothes, then I began to wear their clothes for my late night walks. On my return I would again get relief followed by the shame, disgust , regret and sorrow. Unfortunately as time went on the anti climax feeling began to last for shorter periods of time.
    Then I decided there maybe a way to ditch this addiction, I decided if I was to cum it had to be during my late nights walks and I had to be a minimum of 1/2mmile from the house. So my next walk I popped one of the girls stilettos into my handbag and headed off. At the turning point of my walk almost a mile from the house I found a nice quiet corner I descretly took out the shoe and began I was sooooo turned on just a few strokes I experienced the most intense orgasm ever my legs went weak my head went so light.
    Then the reality hit me s@&t I was so far from the house and dressed like this!! I began the walk of shame I was do disgusted! After that each time I had to cum this is what I made myself do, needless to say in the next year and a half I didnt cum very often.
    I returned home but 6 weeks before then i dedicated a night to each of the girls clothes tried on loads of different outfits, shoes, skirts, nylons, lingire, tops the works, but I took loads of photos with their own cameras, even photos of me depositing in their shoes. I also to a photo of a note the basically said I was sooo sorry for invading their privacy, and that this is what I have done with their stuff over the past two years, and that my fate is in their hands to do what they wish with these photos as i had invaded their privacy.
    Then left the cameras back where I got them, at the end of the 6 weeks I heard nothing so I deleted the photos, but if they ever deleted one of their own photos by mistake and use recovery software the will also find mine.
    I miss wearing their clothes I really do need help!

  3. Daphbryn 4 years ago

    For me it is all in the mind since the body I was born with doesn’t match who I am inside (445 COGIATI) so I dress when I can and dream about maybe coming back as the bi woman I am in the next life ( if reincarnation is a fact). Until then I do all I can to live as the woman I really am with the means available to me. I even find my self with crushes on lesbian women and have major vagina and breast envy.  Best wishes to all of my sisters on this wonderful website. I love you all, Daphne

  4. Daphbryn 4 years ago

    For me it is all in the mind since the body I was born with doesn’t match who I am inside (445 COGIATI) so I dress when I can and dream about maybe coming back as the bi woman I am in the next life ( if reincarnation is a fact). Until then I do all I can to live as the woman I really am with the means available to me. I even find my self with crushes on lesbian women and have major vagina and breast envy.  Best wishes to all of my sisters on this wonderful website. I love you all, Daphne

  5. Racquel Lynn 6 years ago

    I had my ears pierced when I was 18. It was the 80’s and I was into the rock scene, so I started out under the cover that they earrings and eyeliner (and yes, even some of the clothing) was all part of the rock and roll thing, but the underliing truth is that I knew I wanted to be a girl and adopted a very feminine, yet still rock and roll appearance.
    (that was the wonderful thing about the 80’s was that I could somewhat crossdress right in front of people without any of them knowing I was crossdressed. aside from actually wearing a dress or skirt, pretty much any other female clothing was fairly acceptable and cool.)

    Since coming out, I have had some permanent hair removal done and also had permanent make-up. Black eyeliner and Full Magenta Lips. So I wake up every day with that much make up on already. I plan to do some other permanent make up and also some more hair removal.
    I have also had long hair every since I was about 11 or12 years old.
    Once I have some dental work done this June and finish the hair removal on my face, my next hurdle will be breast implants and tracheal shave.

  6. Elizabeth 6 years ago

    As I have often said, I do not even try to “pass”., I am simply a man who likes the feel of women’s clothing. OTOH, I grow my hair long, but that is because, once every two years or so, I have it cut, and send it to locks o love, to be made into wigs for children undergoing chemotherapy. I feel it is an inexpensive and painless way to give back to society, as I feel we all should whenever we can. So right now, my hair is at that disgusting lenth where it is too short to tie back with any real success, but so long it is constantly in my eyes. LOL When I have to do things that require me to use both hands, like playing in theater pit orchestras, I simply hold it back on both sides with bobbie pins. I usually get a little ribbing about it, but I am comfortable in my sexuality, (both the masculine and the feminine sides) and just laugh along with them.

  7. Kelly 6 years ago

    I am growing my hair long as I have straight hair and will look really good when its longer.I will have it combed back during the day and let it down at night when I dress up.I have ALWAYS wanted real long hair and now I am gonna let it grow as i love the feeling of hair running down the sides of my face.By this time next year it will be near the length I want it and may get blonde highlights as I am a brunette.Since I have been using conditioner more often it has been growing like crazy 3/4 an inch a month, a bit more than the average growth of 1/2″ a month.

    • Profile photo of Vanessa Law
      Vanessa Law 6 years ago

      Nice Kelly! I’m growing out my hair as well – blonde highlights are tremendous fun!

  8. PTCDRachel 7 years ago

    Hi Wendy,

    I remember “coming out” to my wife – it was very hard on both parties and, to be honest, still is. I love her, she loves me, the bit that’s hard for her is that the me she loves incorporates the “female” part of me, without that I wouldn’t be the me she loves (hope you got that bit!!). Once the cat is out of the bag, it can never go back in and I do sometimes “assume” she’s more ok with it than she is – I realise when the caustic comments come out followed by “I’m joking” when I know she isn’t. It will be a hard slog for both of you, I know it’s a shock, to him it will be a relief as hiding it is very hard work – very stressful – I’ve regularly thought I was losing it and there were 2 people in my head – now I accept it’s all just me. All the best to you both and please, I understand it is hard, very hard, but do try to understand – don’t let him run roughshod over you, but don’t try to force him to give it up – it’s part of him, and forever will be……it’s like asking him to rip his heart out (well, that’s how it feels to me). It’s only society’s prejudice that causes the problems, how long was it before women in trousers were accepted ? I know it’s probably a pipe dream but the old adage of “clothes do not maketh the man” really is true.

    Good luck and I sincerely hope you get a good outcome for both of you.

    • Profile photo of Vanessa Law
      Vanessa Law 7 years ago

      Rachel, you bring up a good point on assuming that sometimes she’s more okay with it than she actually is. I find this sometimes myself, and I need to be careful not to assume it’s okay. Sometimes wearing makeup or women’s clothes in public will make my wife upset. If I’m not paying attention she’ll get upset because I didn’t notice she’s upset. I guess she has the right to expect woman’s intuition if we’re dressed as women, huh? :)

      • Racquel Lynn 6 years ago

        My wife was the first person I came out to, other than a couple of friends in high school. She was amazing and very supportive and actually loved it. I told her before we got married that I was a crossdresser and I also wanted to have a sex change and she still married me. We divorced after almost 10 years because of financial problems, not anything to do with my gender issues. I really did not think I would find anyone else like her that would want to be with me and accept me, much less support me and encourage me and love me more for being the real me, but I have been very lucky that I have been able to find women that do support me, but there have been a couple that said they were supportive, but it was obvious that they were not as comfortable and accepting as they said they were. I let them know up front that I like to crossdress and that I will eventually be living full time as a female and that I fully intend to pursue surgery to become a female, and they said they were fine with that, and also fine with me dressing up, but not so fine with me being out in public or around their friends. I tell them that this is what I told them up front and they better get used to the idea, because going full time as a female means full time and once I start full time, I cannot only be a female when it is convenient for them or to please their friends.
        So some will say they are okay with it, thinking you would never go out in public like that or whatever and then when they see that you are serious and it hits them that what you said is for real, they don’t know how to handle it.
        Although most of the girls I have dated since my divorce already knew about me before we started dating and have already been supportive, but for those who did not know before, I am honest and straight up front with them and I am more assertive when I tell them that I will be living full time as female and going for surgery as soon as I can afford it. I let them know what happened with the two previous girlfriends who knew up front, but then only had a problem with it when they actually had to deal with the fact that I was going out in public or going to hang out with her friends wearing a dress or something feminine.
        I make it more of a point to get accross the reality that “Yes, it will happen, this is where my life is headed so don’t tell me now that you can accept it and then give me a problem about it when it actually happens”.
        Overall, I have gotten acceptance and support from the girls I have dated. It pays to be open and honest up front.

  9. wendy 7 years ago

    I’m freaked out by my cross dressing bf. I’m ready to leave him
    but I love him too much! help me.

    • Profile photo of Vanessa Law
      Vanessa Law 7 years ago

      Hi Wendy,

      Can you tell me a bit more about you boyfriend? When did he first tell you he was a crossdresser, what does he share with you?
      It’s only natural to feel a bit shocked and overwhelmed the first time you find out that the one you love is a crossdresser. For many crossdressers it is one of the first times they’ve told someone else, and they’re feeling both vulnerable and elated at the same time. This may mean that he will go a bit faster than you would like, perhaps showing you more of his crossdressing side than he would otherwise.

      A good place to start is to have an open conversation with your boyfriend. Let him know about your fears, but also let him know how much you love him.

      Good luck hon.

    • Racquel Lynn 6 years ago

      If you truely love him, then you shouldn’t leave him over this. At least give it a try. It may take some or alot of getting used to, but if you love him, and you take the time to get to know his feminine side, chances are that you will wind up loving him even more.
      Rejection is common for crossdressers and others in the many facets of the transgendered community, but what is also very commonly found is that most people, even if they are turned off by it at first or have a hard time accepting it (Friends, family, coworkers, spouses, girlfriends, etc.) if they do stick around and give it a chance, they not only learn that it is the same person they have always known, but they wind up liking/loving them more when they are able to come out and be themselves because they are not having to hide their true selves and become happier and even more pleasant to be around.
      It is possible that you may never be able to accept it, but if you care for him, he deserves the chance. Take the time and get to know your bf for who he really is. If he can share this with you, then chances are he will always be honest with you about everything and never feel like he has to hide anything. That is a rare thing these days.
      And please do not be worried about what other people will think if they see him in a dress. It doesn’t matter what they think. It is about what makes him happy and you happy. Do not let other people decide your happiness. A lot of times people are more worried wondering “what will people think of me if they see my ___________ (husband/boyfriend/son, etc.) wearing a dress? It is not so much that the crossdressing itself bothers them, but what other people will think about it. Or they are fearful of it because they have been taught their whole life that it is wrong or a sickness and all kinds of other things. But take the time to make that decision for yourself. Many people who say things like that have never known a crossdresser or taken the time to get to know one and just repeating what they have been taught by others who also do not know any out of their fear for the unknown.
      I was dating a girl once who said she had no problems with me dressing up or even going out in public as a female, but she freaked out if I was leaving the house with her to go visit her friends wearing anything that was the least bit feminine. Her parents knew about me and supported me greatly, and she also did not give her friends enough credit, because most of them knew and also were supportive. She was the only one that had any problem with it because she was the one who was worried about what her friends would think, but she never had a problem with me dressing at home or anywhere her friends were not at.
      Not saying that this is the case with you, but chances are that if you really sit and think about it, you will find that being worried about what others would think if they found out, or negative things you have heard others say, is likely a bigger part of the problem than his crossdressing itself. Really, if it makes him happy, who is it hurting?
      Good luck to you both, whatever you decide.

      • prashad 4 years ago

        addresses same woman those help of crossdresser their ph.no.

  10. Claire 8 years ago


    I usually try to help loved ones and friends. For example, shopping can be a major issue and it’s hard to find small boutiques that feel comfortable helping “us.” So, i’ve found a few sites that are welcoming and if you call their offices they are very sweet, compassionate and understanding to the taller cross dresser.
    kathrynkerrigan.com for shoes
    katclothing for clothes

  11. Vanessa Law 8 years ago

    Hehe, indeed :)
    When I got my ears pierced a few years back I thought everyone would a. notice and b.freak out. Neither actually happened, and while it was a moment of courage to go into the local Claire’s and get them pierced it opened up the “world of earrings” to me :)


    P.S. I did figure out how to type with longer nails (~ 1/4 inch) by keeping my fingers nearly horizontal to the keyboard, it made a pleasant clack, clack sound as I typed.

  12. Lynn Jones 8 years ago

    I’ve moisturised for as long as I’ve been shaving. I think I tried after-shave the once, but as Golumn once said: “Aaah, it burns! It burns!” So never again :)

    I have very short hair now although in my teenage years it was very long (it was the 80s). I’ve never had my ears done and while I think it would be a change to wear different styles of earrings, I’m in bloke mode more than not, so I don’t bother.

    I don’t like my nails to be too long because, as you say, they get in the way of doing things. I remember trying false nails one weekend (I think most TG people do) and even after shortening them to a more reasonable length, I was surprised how difficult everyday tasks became. Typing was a complete pain!

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