Getting Started with Dressing (and What I Wish I’d Done)

One of the common mistakes about crossdressing that I made when I was young was thinking that I had to find someone to help me buy clothes and do my makeup. It is indeed easier if you know someone, but there’s still a lot you can do on your own when you’re just starting out. I definitely waited longer than I should have, but frankly I was just scared and lacked confidence in pretty much everything. At the same time, though, growing up in the 70s it really was a different world before the internet came along. I never even knowingly met another CD until well into my thirties! Now there are so many opportunities to talk to people online, and maybe even meet some of them. And there are tons of free makeup videos on YouTube. One of my regrets is that I never dressed seriously in my twenties. OMG, I would kill to have been taking pictures at that age! But it just wasn’t in the cards. I was so confused and moody when I was young, just kind of drifting through life. Looking back I wasted a lot of time and missed a lot of opportunities. So in a way this blog post is written to that confused kid all those years ago and what I wish I’d done back when I was getting out of high school.

Of course I don’t want to come off like the old fart dispensing wisdom, BUT if I were to give any advice to those starting out it would be not to wait, but to start playing around with makeup and getting some outfits together even if you have to do it on your own. It doesn’t have to be fancy. In fact simple is better when you’re just starting out. I wrote a little thing on dressing tips several years ago here (which probably needs to be updated), but knowing what I know now here’s the simplified version of what I’d do:

To start out I’d shave my legs and my whole body, or as much as I could get away with. Of course I didn’t have much body hair back then so it wouldn’t be a big deal. Then I’d get some inexpensive makeup from Target or the dollar store to practice with while watching YouTube videos. Then I’d slowly acquire some simple outfits, starting out with tight-fitting shapewear and pantyhose – Legg’s pantyhose has a nice sheen and are pretty inexpensive. For a bra I’d probably just stuff it with panties or birdseed in used pantyhose legs till I had the money for breast forms (I was broke back then). And finally I’d look for some cute outfits again at Target or the thrift store or on Ebay, maybe even something like leggings with a houndstooth pattern, for example, or tight skinny jeans, which can be a sexy casual look if you can pull it off. And of course I’d also get a wig or two on Ebay, definitely with bangs, or from discount wig stores online.

None of this has to be very expensive. The main thing that’s required is to just sit down and practice with the makeup and the clothes until you start to put together a “look” for yourself. And then the next step is to eventually work up the courage to go out dressed, maybe to a munch if you’re in a decent-sized city, or going to clubs with friends, or just going out alone if you have to (and trying to be safe). If I’d had the sense to do all this when I was young I would have been on top of the world and not even known it. But like I say, I didn’t have a clue back then and didn’t know where to start. In any case, that’s my take on what I should have done all those years ago – it seems really obvious to me now! If you’re closer to my age and grew up before the internet, let me know what your experiences were like starting out and at what age you became more active with dressing. I hope this maybe helps someone out there a little bit…Hugs, Sandra

photos by Delilah Knotty

17 thoughts on “Getting Started with Dressing (and What I Wish I’d Done)”

  1. I agree – cross dressing life is so much easier with the Internet. I started dressing in the early 70’s, and if I knew then . . .
    Your advice is spot on, Sandra. I would only add that you should really try to find a friend to confide in, preferably a female, that is what I truly missed out on in my younger days.

  2. Amazing how many parallels I find when I read about the early experiences of others. My first venture was back in 1971. I thought I was the only one. It came and went over the next 42 years, then exploded in 2013. It took me those 42 years to realise that I wasn’t the only one.

  3. I perfectly understand your comments Sandra, I began crossdressing to practice DID scenarios 15 years ago and make up never was a priority. When I joined social media (FB) someone suggested me how good I could look on make up, I need to congratulate him, began make up almost three years ago, was hard at the beginning and it’s a journey never finish, but I am so glad to have started and move forward, I see myself in the mirror after make up and can’t believe I am the person in the mirror.

  4. well….internet def has a part in everything …so glad you did start….wonderful job always…and still…the best legs on the net!

  5. Great advice! Thank you. I started when i was very young, in the 60’s. Quit in late 70’s. Wish i wouldn’t have. Started back 10 years ago and now the feeling are so much stronger. My advice to the younger folks is to push your limits now as much as you can. You will most likely never look better. As you get older, things start to sag and fall apart.

  6. Hi Sandra. Been following you for a while. Never really wrote in.I’m like you and a few others, I’m in my 70’s. I was 10 when I first thought about cross dressing. Dreamed of being a DID tied up and gagged being rescued by my hero.Movies, TV or detective mags that was my in the picture. When I hit 18 and moved out, it was late 60’s, started to buy my own clothes and makeup. I was a secretary type, no flash plain ordinary woman. went out every chance I got. Guess it was easier for me because I wanted to be a real woman. I learned as I went. There were ups, downs and total disasters Don’t know how I met other C/D’s. Early 70’s I was pure and innocent. Went to a party. Thought it was a regular party. There was some guys there. One came up to me and said “I want to fuck you” I’m like what. I was a virgin. Pushes me face first over a chair, hikes up my dress slams hi hard cock up my ass. I t was Slam Bam Thank You Madam. 30 secs it was over, I’m like what as that. Same person invited me out again, of coarse dumb and stupid I went. Bad move.Should have listen to my gut. All I was was a piece of meat. Got gang raped. I was bent over and was being screwed up the as and another guy is shoving his cock down my throat forcing me to swallow his cum This was 7 guys doing this. I was sore and could hardly walk. Never went out for 2 months. Started to go out with different group, better group. We learn off of each other. Some had same story as me. We were into a little bondage which was fun. It was light. Found a few people and had sex. It was great. We took are time and enjoyed ourselves. I when out shopping and to the hairdresser and was myself. I never felt so alive as when I dressed. I don’t go out any more, bodies falling aprt. I miss the days of 4 in heels and pencil skirts, being tied up or have great sex. I’ve gone on too long with the story. Never told anyone this. No one wants to hear anyway.With the stories women come out with today I can relate. I’ve been there. My piece of advice, be yourself. Don’t be glam. It’s all right at home or parties but not on the street. Listen to your gut. If it says no don’t do it. There are a lot of good people out there that will help you. If your dressed and go out and what to buy a dress or shoes they will treat you like a woman with no problem. I never had problems when I went out. Got called sir a few times just let it go. Having read your site Sandra I really like it. Little stories come to mind over the years sort of jars the memory.One last piece of advice if you go out DON”T BE AN ASS. It really turns people off. Thanks again Sandra for listening I feel a little better just telling this to someone like myself.

  7. While I grew up in the 70’s / 80’s and I had a thing from bondage from as far back as I can recall, dressing was never part of that equation. I was in my late 30’s before dressing became a thing for me and into my early 40’s before I took it seriously. As others have said having a good female friend really does help, also coming to terms and accepting yourself for who you are is really important, over the past few years I have spoken to several people who are in a continuous cycle of denial and purging all things female from their lives and wardrobes, only to be unable to resist the urges and start from scratch again. Make up you just have to keep practicing, like any skill it can be learned it just takes a little time, but do not go mad and by expensive make up at first, save that for when you have gotten to a competent level. If you can pluck up the courage, getting a foundation match and a professional make up lesson are well worth the effort and despite what you think inside the folk providing these sorts of services are more than happy to do it for girls like us, I only managed these this year and I am like a lot of you wishing I had done them earlier.

  8. Hi Samantha, I was in a mall, when I first started out, and a woman at a Carol Baker booth in the mall approached me and ask if she could do my make up. It wasn’t that bad. She knew what I was and showed me eyeliner and shadow, lips and foundation tricks. She was very nice, Like I said above there are a lot of good people out there, Just treat them with respect and you have no problems. I had more friends on my fem side than my male side.I was one that purged a few times early and one day I said this is who I am live with it and I did.Was a female every chance I got and was happier for it.

  9. Sandra has gone off to visit family.I was wondering if she would go as a female. I ask this because I was into dressing and going out since mid 70’s. In the mid 80’s I met a guy and we both liked each other And I moved in with him. It lasted about a year and then splitsville for some unknown reason only he knew. Any way about 4 months in it was thanksgiving and we were going to have a small turkey and dinner. we were out shopping and he said you should get a bigger turkey. Like why. He want to invite my mom and 2 sisters to dinner. Like WHAT. I said no way. My mom has never seen me dressed ever.The more I fought with him they more he wanted them to come so I gave in. He has never seen me as a male and my mom has never seen me as a female. So I bite the bullet ans was a female. Day came got up did my make up and dressed.. I wore a mid blue sheath dress with pleats down the lower left side and black pat t-strap pumps with the sling back plus the other stuff. I cooked the turkey and other stuff. He went to pick up my mom. I had to wear a pad I was so nervous and leaking all day. I heard the door open. I was so petrified I almost pissed myself. My mom saw me and hugged me and said I looked nice. We talked and had dinner and a little chit chat and she was ready to go home. She hugged me again and said “if any thing happens you can always come home. I will support you what ever decision you make.” It took every thing I had not to cry. He drove her home and I cleaned up. He came back and I looked at him, sat down and started to cry. He said whats wrong, it went OK. My mom accepted me for what I was a female. I was more happy tears than any thing. I was wondering if any one has had the same experience and how they handled it. It may help other people to come out to their parents.

  10. Thanks, everyone, for all the comments! As Tracy said, I so agree about pushing one’s limits when young. I wish I’d known but, well, we move forward from where we are.

    Hope everyone had a nice New Year’s Eve!

  11. I have not been into the CD scene very long & I’m using most of the things that you did at first Sandra. Main thing I’m currently struggling with is a simple yet effective way to get made up woke make-up. Can you possibly please help me out & what to use?

  12. Hi Lily, I’m not sure what you mean by “woke make-up.” There are a lot of tutorials on YouTube for all kinds of makeup questions though. I would just check there…Thanks for posting! ~Sandra

  13. Hi Sandra,

    I got started VERY early in life…when 3 of my 17 aunts (ALL 17 afraid of men!) dressed me on weekends when I was supposed to be attending church with them. Grandpa was a mean drunk in his cups and tried to kill them many times (according to my mother, one of the 17). This continued until high school graduation when I left the area via the military route and discovered fetish dressing when in Amsterdam, Holland. There followed over 30 years of marriage to a bi-polar and suicidal wife when I had to hide my interests (she would use ANY excuse to try suicide!). After she passed away (of spinal cancer), I married again to a woman who had been in show business, loved costumes, heavy makeup and “more” who would dress with and for me in the bedroom – IFF (if and only if – there are always consequences – grins). She passed away years ago too (DAMMIT – She is the one I will miss!).
    Knowing what I do now, and wanting what I need now, I would have not married the first wife, but waited until I could have found someone accepting or tolerating my interests, I’m still trying to meet those others (Mature Women of all genders – wicked grins) who have an interest and a need to be who and what we are.

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