I think most of us have heard this before from women, “Men just wouldn’t be able to handle one day of a woman’s life.”

I believe they’re right; at least when talking about crossdressers in general. Let’s imagine this scenario… You get a windfall of, say, $100,000. After using $80,000 to pay off any debt, home improvement, etc, you end up with $20,000 that you can use for anything you want.

Your wife -who is aware of your crossdressing – and kids are going to be out of the country for one month, and one day after they’re gone your company announces that your place of work is going to be remodeled; you get four weeks of paid leave.

Makeup Magic

All of your friends and relatives are mostly out of the picture. I think you get where I’m going. You’re all by yourself, no worries about money, no stresses about work or family, and you can finally take some time all for yourself. You’ve always wondered what it would be like to spend several days living full time as a woman; now is the chance! You even clear your plans with your wife so there aren’t any feelings of guilt.

You pack your bags and go to a large city where you’ve leased a furnished apartment for the occasion. You do your shopping, lots of it, and you have everything you need! Clothes, shoes, makeup, shoes, hair, shoes, accessories, shoes, etc. And now… it’s time to enjoy and experience living almost three weeks fulltime as a woman!

Or is it?

It’s time to be real and honest: What did you picture yourself doing those weeks? More shopping? Clubbing? Just dressing up and staying in? Taking long perfumed hot baths? Taking lots and lots of photographs? Finding a support group?

You have your bag of men’s clothes, which you will need to change into so you can pick up takeout food, or buy wine and cigarettes; you know you will be carded, or you’ll need them in case you have to change a tire or go visit your aunt who lives in the area. Maybe your team will be playing over the weekend and you have tickets to the game!

All those girly activities and the safety net of knowing that you can always “Jump back into drab” as needed. If any of the previous ideas crossed your mind, honey, you’re not even close to experiencing what it would be like spending full time as a woman. You would be spending those weeks as a lucky crossdresser at best, living in fantasyland.

I think it would be a magnificent educational opportunity for everybody to have a chance to experience a real woman’s life. So… let’s change things up a bit, shall we?

For starters, you wouldn’t have any single item of men’s clothing. On a weekday, you wake up early enough so that you are ready to go out, either driving your own car or catching public transportation for a trek downtown or to the suburbs to look for a job. You interview at a store, the mall, something; congrats, you’ve got a job! Now spend all day long out there, with few breaks, dealing with others, so that when you get home you’ll be able to relate as to why your wife kicks off her heels and takes off her bra, swearing how she’ll never wear hose again.

You had plans to go clubbing almost daily—oh the excitement! But…there are still womanly things to do. A day or two before the big night, you realize you need some sleep to be able to keep up with your daily duties at work. When you get home from work, how about dressing up nicely so you can get started on cleaning up the place? You always liked doing your laundry, and household chores in your French maid’s uniform. Bring them on; you’ll have them done in no time flat, all the while you’re wearing your sexy lingerie and those killer 6″ stilettos, right? Ah yes, you need groceries, too. You downgrade to 4″ heels because you refuse to look all frumpy like most women when you go to the market. You jump in the shower and take your time to get your makeup done, pick a nice outfit to wear, add jewelry and accessories only to realize that it’s now too late to go shopping for groceries. Having fun yet?

The weekend is coming, and you can’t wait! Party time! Your boss calls and you have to work on Saturday afternoon. Finally, on Saturday evening you are ready to go clubbing! You get ready, (no less than 3 hours even when trying to hurry) and get to the LGBT friendly bar that you’ve been to before, only to out find that it’s closed. Will you dare going to a mainstream place?

I think that you are getting the point. This is what both cis and trans-women see in us. Many of them are of the opinion that crossdressers are just pretending. And in many cases, they’re right. We “dress-up” only when we want and wear the pretty new clothes just purchased. Oh and how we love heels, the higher the better. In our world all we have to do is kick them off when we’re tired or our feet hurt. Most of our crossdressing activities are fun; such as shopping, going out with friends or to clubs, movies, etc. We don’t really participate in the daily responsibilities our wives and SOs have to. And we dare ask them how come they aren’t wearing a nice dress when they go pick up the kids up from school! They live in reality, not in a world of fantasy where every day is a party and there is both fun in staying home or going out with friends.

I didn’t have those exact circumstances (I wish!), but I did have two weeks for myself; a few days were going to be at home and the other days traveling to meet with friends. I made the compromise not to pack any single item of men’s clothes. Yes, I had a great time. Yes, I enjoyed spending time with friends, going shopping, going to the nail salon, and clubbing. But also, there were many times when dressing up felt more like a chore. Spending one hour or even only 30 minutes getting ready just so to go get a cup of coffee, when I could have done it in 30 seconds flat in guy mode, was exhausting!

At the end, on the 12th day, I decided to go back home earlier than planned. I had to drive back to my home town and I was tired… I was outside of a convenience store, sitting next to my car smoking a cigarette, wearing shorts, a simple top, sandals, and almost no makeup when a nice woman walking past engaged me in conversation. She asks if I’m ok; I told her I was on my way home and was only tired. She wished me luck. It was one of my nicest interactions with people, and one where I believe that she just saw me as another woman wishing to be done with her day.

Many here wonder at times if they could live full time as females. Sometimes, I ask myself if I could get away with it; living full time/ transitioning. I think I could. But you see; that is the thing. People shouldn’t transition because they can, but only because they must! I don’t have to! I enjoy my life as it is. I like being a husband and a dad, a project lead at work, a good son, etc.

Being able to have some chances to dress up and present as a woman is good enough for me. Notice I didn’t say “chances to be me.” I am me all the time, regardless of the clothes I’m wearing.

I wish everybody could live a similar experience as I did. I would expect that for many they would discover that they don’t need more than what they currently have. Maybe they’ll find out that the grass isn’t greener for all, and hopefully gain new appreciation for their everyday life…and that of their spouses and partners. It’s ok to pretend and to just be who we are, just as it’s ok to want to live authentically. There’s plenty of room for all.

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The clothes I wear do not define who I am. I am the same person regardless if I present as a man in jeans and a plaid shirt or as a woman in a gorgeous gown. That may have been the most important moment in my self awareness. I don’t have a girl side or a guy side competing in one body. When I get to present as a woman I’m being myself as much as I am myself in my every day life. Being able to realize that I don't have to separate my personality in a "Feminine side" and a "masculine side", but that every aspect in me should be integrated into a well balanced persona was very liberating.

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Bettylou CoxSofiCoral WentworthGabriela RomaniSara Styles Recent comment authors
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Gabriela! Girl you said it exactly like it is for me 🙂 Gender is a made-up social construct and flitting between a male/female isn’t what it is about for me either – I love to be able to go out in nice, girly clothes and not even worry about my balding grey hair. (hey – just so I don’t look completely stupid I have a nice little beanie to hide that hair issue, but it usually gets taken off once I’m relaxed in a situation – guess it’s my safety/comfort blanket) My bod looks fit and hot in the right… Read more »

skippy1965 Cynthia
Active Member

Sofi-if you haven’t already, scroll back through the older articles from Vanessa (2007-2014) and others from the early days of 2015-17-there’s lots of great stuff out there that our newer members haven’t seen. Also the forum archives ( https://www.crossdresserheaven.com/forums/forum/archives/ ). And if you find an author you like and want to read more by them, you can go to their profile page and click on articles or forums beneath their cover photo to see what else they have written. Be sure to leave comments if you like something (like you did here) -they are lifeblood for writers .


Thanks Cynthia, Ahhh – ‘The Early Days’, I’m sure I’ll find loads of interesting, illuminating and heart-rending stuff back there but… I am sorry but life is too short for all that searching! Unless you have some sort of “Classic Posts and Articles” section then I am afraid I’m gonna pass 🙂 If you’ve got any recommendations/links though I’d definitely check those out my Girly Friend 😉 [I can't help but mention, dunno why - for atmosphere/context i s'pose - but I am having a Joan Armatrading binge on Spotify and feeling very nostalgic and .... very much at peace,… Read more »


Gabriella what a great article. Thank you for writing it. The longest i have been dressed enfemme is 3 days. Prior to that was 2 days at Ptown and the poconos. When I retired at 62 I drove cross country by myself to camp with friends of mine in Arizona. I took along some femme clothes and went to Las Vegas. I booked a room for 3 nights and went to the Glamour Boutique and got a makeover. I had a awesome time those 3 days. Now every year I go to the Keystone conference and First Event for 3… Read more »

Dame Veronica Graunwolf
Active Member

Gabriella….howdy girl. Holy cow………….you were so….busy! I had to go for a nap after all this activity. Whew!
Sounds like fun though. Thanks for sharing.

Dame Veronica

skippy1965 Cynthia
Active Member

Gaby-great article and excellent points. Like April, I’ve spent as long as 11 days in full Cyn mode or Esprit-including flying cross country both ways. At work, I dress in “stealth Cyn mode” where all my clothes are ladies clothes just not obviously so. Ladies polo shirts, trouser socks, penny loafers, undies and cami and skinny jeans or ladies khaki slacks. I got my ears pierced two years ago and ear colored cubic zirconia or turquoise studs at work and my hair (which is my own and down to mid back) is up in a middle/high ponytail and I wear… Read more »


Cheers m’dear – brought me tears… Good for you 🙂 Very honest and moving , real, authentic, beautiful… I get you darlin’… i’m gonna do that ‘go to work in a skirt’ thing ‘real soon now’ Like, hell – I told them already what I am and yeah, we had a laugh at our now traditional Friday ‘Pub Lunch’ [yeah yeah – I am so English, no, no, shit, I’m Welsh now dammit….] and they totally accepted it, plus, tbh, I’m more of man than any of them… luckily 🙂 …your ‘work situation’ may be less favourable… but hey –… Read more »


Money does’nt buy Happiness–However—Gay/straight/trans or whatever–money buys you Freedom to pursue happiness If you choose—No life is perfect in Every way– The further down the economic ladder you are the harder life is for anyone—Esp. when our sole purpose becomes Impressing others with The things we own like the corporations Teach us from a young age–Chasing material goods (beyond basic needs) erodes our Freedom to Not fit in–(be ourselves)

Diane McG

You really hit the nail on the head with this post. no, I wouldn’t want to be a woman, for all the reasons you talk about. I once though I did, because then I could wear all the pretty clothes without any excuse. But now I know I can enjoy that part of me, and enjoy the drab part of me, and all the in-between parts of me. I’m having a blast.

T.J. Byron

Gaby…love you and all your writing. You are an inspiration to anyone who has similar feelings we do.
I understand your frustration with folks who use the wrong spelling, for words they use to make a point. I present the words ” further ” & ” farther ” as an example.
At 73( October) I ‘ ve through a lot. Out in public since the 1960’s. Blazing the trail over the years.
Always good to hear from you.
I have an article coming out in a week or two. Watch for it.
Dr. T.J.

Coral Wentworth

Gabriela, Thank you, I so enjoyed this and I have read so many of the replies and it is nice to hear such honesty among so many. I have been raising my youngest as a single father and mother if I can say that, It has been just her and I . I have raised her from the time she was 9 months old I, I am so bless for this has helped me develop into the person I am today. Although I always thought I was born in the wrong body it was having to be a mother that… Read more »

Sara Styles

I wasnt sure where you were going at first, but wow that puts it in perspective. For me it is fun, and I would love the challenge of living full time for 2 weeks. However, I don’t have to, or I don’t feel like I have to.

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