Crossdressing Mistakes How Many Have YOU Made ??

[Mink]

just one:

becoming a crossdresser in the first place!

zing!

[CynthiaD]

There are no mistakes, only learning experiences! I sometimes regret not going full-time 24/7 in my teens. But when I think about the reasons I didn't, I'm sure they were good ones. (Actually, crossdressing was illegal most places when I was a teenager.)

[flatlander_48]

I've been fortunate not to have hit any of the above (yet). However, one that wasn't mentioned...

I now have a couple of shoulder bags and a couple of hand bags to choose from when I go out. However, I really have to work at remembering to take the bag with me when going to the restroom. You have to get a key to use the women's at the joint where the Rochester Grrlz hang out. A couple of times I've gone to get the key, entered the restroom, sat down and THEN remembered that my purse with car keys, house keys, credit cards, money, etc. was still sitting out where I left it. It's almost a Rosanne "Staple it to your butt..." moment...

DeeAnn

[irene9999]

There's been lots, cheap wig that doesn't blend with my face, poor makeup application,etc. I'm getting better though!

[kimdl93]

Your comment about heels and potholes reminds me of the longest 15-20 yards of my life, attempting to maintain my balance, composure and ankles as I crossed a cobblestone street.

Most of my mistakes have been wardrobe related....and have long since made it to Goodwill. Other than that, I've tried any number of eye shadows, but being blonde and blue eyed, the pallet that works seems to be fairly narrow...Browns, beige and rose. So much for the green, blue and metallics!

[TrishaTX]

Starting out a did a few professional makeup sessions, but I did not listen enough. I am still not great at makeup. Now I belly wear any because my wife does not seem interested. The hardest moment for me, was quite awhile back when I dressed to do to my first bar party in Manhattan on 14th street. I had a professional make up etc but i street parked a block or so away and had to walk. That was my first time doing that...those 1000 feet too two hours in my head, once in the near, I ordered vodka( i don't usually drink hard liqueer just to calm down). The night went well and I enjoyed the party but that walk was hard, and who knows how I looked walking lol

[Elisa Lace]

Insisting on zipping up dresses that used to fit perfectly 10 years ago and: 1) having the worst time of my life trying to unzip it and 2) actually breaking the zipper... Oh, the dress was my mom's. Now that happened 5 years ago... but I'll never force myself into someone else's clothing again...

[Diane Smith]

1) Long, skin-tight, sequined gowns are for prom and Vegas showgirls. You don't need 25 of them in your wardrobe.

2) No matter how many hours you have practiced around the house, going outside and walking real distances on city streets in heels will be much harder and more painful than you expect.

3) Buying clothes, shoes, wigs and makeup in real stores and trying them on is about five times more likely to get you something that actually fits and looks good on you, compared to online shopping.

- Diane

[MonicaMarie]

All of them! Well, except for white shoes with black stockings... At least I've always known about that! It's still a work in progress and I have many more mistakes to make, but hopefully they're getting less frequent!

[CutieJulie]

Agreed dont buy clothes that are smaller then your size Or you could get stuck in them lol

[Michelle789]

I'm TS, but I much of this applies to someone who is transitioning to live full-time as a woman. We make the same mistakes too.

Mistake Numero Uno. Buying a wig online without ever trying it on. This is the worst mistake I have ever made. The wig might look nice on the model who tries it on and in the photo, which was probably engineered to look really nice, but when I got the wig it looked absolutely horrific on me. I will never, ever, ever repeat that mistake again. I always try on a wig before I buy it, and see how good it looks on me. Preferably all made up so I don't see 5:00 shadow interfering with the look.


Buying clothes and shoes that don't fit, because I bought them online. Although I would always say to buy your wig in person and try it on, under some circumstances buying clothes or shoes online may be necessary. Maybe you live in a really secluded area and the nearest clothing stores are 100 miles away, or maybe you need an extra large size that you can buy only online. Maybe you want a specific shoe that is only available online. However, I have made mistakes buying clothes and shoes online. I now only buy clothes, shoes, makeup, and anything else I need, in person while trying everything on. I am lucky that my clothes and shoe size is available in most regular stores like Target, Sears, Nordstrom's, Ross Dress for Less, Steinmart, JC Penney, Macy's, so I don't have a need to buy online. I would say this, buy online only as a last resort. Otherwise, buy in person.

[Dana44]

The second time I put on makeup. put way too much concealer around the bottom of my eyes and upper cheeks. It looked like a mask on my face. LOL. A GG had her eyeballs bulging out looking at me at a restaurant foyer. Yeah, I learned from that. Getting way better on my makeup. My SO got me some fine pencils for my eye liner. Blue and brown. Much easier to put on.

[Teresa]

As far as the wife is concerned is my big mistake is that I CD ! Can't do much about that one !

[Rhonda Darling]

Visited my dad's gravesite at Arlington Cemetery in full Rhonda mode. No problem getting in or parking. But the walk across the soft grass in 4" spike heels, not so much. I learned a cheap way to aerate the lawn, but walking upright in a dignified, "nothing to see here, folks" manner eluded me. Standing only on the ball of your feet, unable to put your heel down, is a challenge best left unmet.

[Donnagirl]

Check the addressee before you press send on an SMS picture of you all frocked up and pretty... Check it then check it again!!!

[XemmaX]

tits too high, bad eye make up, wig stuff. the list goes on crossdressing does feel like a constant learning experience.

[Sarah-RT]

The biggest mistake I've ever made was "making do" with clothing I bought that didn't fit because I was too nervous to return it or try and figure out my size.

Also, not getting breast forms sooner

[hope springs]

For some reason I forget to check the sleeve hole size. The part of the blouse/shirt that fits under your armpit. The shirts fit perfect and after I wash them they get real snug under the armpit. So even if it fits everywhere else check the pit area, it may be too tight. I guess the the distance from the top of shoulder to armpit is shorter on women.
Also echoing what someone else said.... Take your time and try lots of stuff on. Early on I had a " don't press your luck" attitude and if something kinda fit I bought it and left. I'm learning shopping is an epic event, patience is required. Also learning to mix and match outfits is key. So grab stuff from one store and try it on with stuff from another store. Women must have astounding memories. My wife can recall the locations of various outfits from multiple stores

[Bridget Ann Gilbert]

My biggest mistake is evident in my profile pic. I never should have pinned my wig up. I looked so much better with it down, but it seemed a good idea at the time.

[CherylFlint]

My biggest mistake by far is so much ahead of any of the others it’s like none of the others even count.
So, my biggest mistake of all is not asking for help early on.
One time, when I was around 13 years old, I finally worked up enough nerve to walk into a lingerie store. I just wanted to “look around” and maybe buy a garter belt and stockings but as soon as I walked in this bell rang and this gorgeous young woman, 22 or so, said “May I help you?”
So I freaked and said “Just looking” and turned around and left, in a hurry.
I’ve regretted that moment all of my life. I wanted to say that I want to dress like a girl and need help but I was too afraid and, face it, embarrassed. I was embarrassed that the saleslady would be able to “see through me”.
Stupid me.
And that mistake has cost me a lot of money but, even more important, time. I’ve wasted a LOT of time doing the wrong things when I could’ve saved myself a lot of time and money.
So, my biggest mistake? Not asking for help early on.

[CarlaWestin]

Hands down the biggest crossdressing mistake was getting married the second time, thinking she was telling the truth about acceptance.

Second, thinking that there is actually a kimono that is labeled L that will fit. Evidently L in japanese means size 0.

[Brandy Mathews]

I use Roamans alot too, really like their clothes.
Bree

[NicoleScott]

Crossdressing, like most other aspects of life: if you're not making mistakes, you're not trying hard enough.
Where do I begin.....?

[Sarah Doepner]

How many crossdressing mistakes have I made? How many are there? I'm sure there are a few that I haven't gotten around to, but I'm working on them.

[Megan b]

My most resent mistake happened just the other day. I decided that I going out for the day as Megan, so I showered and shaved extra close, did my makeup. I pick out a navy blue tank and white capris and I was gone for the afternoon. Had a very enjoyable day, felt pretty good about myself. But when I came home and cleaned up, I realized I forgot to shave my chest. Thank goodness that my top was not low cut. (lol) I shave it regularly thankfully but I wish I had not forgot. Still had a good day enjoyed seeing and chatting with all my SA friends.
But my biggest mistake ever was thinking that my (ex) wife would get use to this side of me and just see it as part of me.