Mistake

[sophie p]

Hey girls.
What is the biggest mistake or regret you done while dressing or getting ready. I got my eyebrows waxed yesterday and they are way ott feminine I am trying to hide myself

[emma30]

Hi Sophie
When i was in my early 20's i wore masscara that was hard to remove. A girlfriend noticed and a whole load of bs came out of my mouth with excuses. I did get away with it though.

[Elizabeth1980]

I once put a woman’s ring on my finger that was too small. I couldn’t get it off, and the finger started to go purple after a few minutes, due to lack of circulation. I tried getting it off with soap and easing it off past the knuckle, but that didn’t work. Eventually I told my mother about what I had done (I was at home at the time), who helped me cut it off, I think I used pliers or a screwdriver. It was only a cheap ring, so it didn't matter. Now I am much more careful when putting on rings, not to get them stuck on my finger :)

[MonicaPVD]

Using high quality eye makeup when I knew that I had to change back into drab look for a work related meeting. That stuff is nearly impossible to remove entirely when you're in a hurry.

[emma30]

Monica i always think ahead after my incident its made me paranoid about no traces. Ive turned into a csi investigator over the years lol.

[NancySue]

At the last minute, we decided to go out for dinner, so I quickly changed clothes, wiped off my makeup and we went to the restaurant. My wife whispered that I hadn?t gotten all the mascara off and my lips still looked a little pink. I went to the men?s room to see if I could rub both off. I did and returned to the table. My wife smiled and nodded, then frowned...she pointed to her finger nails. I looked down. I?d forgotten to take off my nail polish which was a very light pink. I?m pretty sure the waitress noticed, but didn?t say anything. Lesson learned...never more.

[Rhonda Jean]

Sophie,
25+ years of brow waxing/threading/tinting I've had a few that were too much. Time to start wearing glasses! Big frames that come up to your eyebrows. The do seem to kind of relax after a few days for some reason. Probably also has something to do with getting used to seeing yourself in the mirror, too.

After you take the plunge to start waxing, you should probably keep it up. Once you've had your brows a certain shape and people get used to it, it's no longer an issue. About every 6-8 weeks for me. A little tweezing and trimming between appointments. Tinting can be as stark of a contrast as waxing. Seems like the tendency is for them to go too dark. Here again, after you get used to it it would be noticed if you quit. Once you find somebody who does your brows to your liking, stick with them.

[BTWimRobin]

Hi Emma,


Hi Sophie
When i was in my early 20's i wore masscara that was hard to remove. A girlfriend noticed and a whole load of bs came out of my mouth with excuses. I did get away with it though.

Oh I can so relate. Early 20's girlfriend thought I looked different. She couldn't figure it out then all of a sudden she blurted out "are you wearing mascara?" I remember it like it was yesterday.

[Teresa]

Sophie,
I can't think of any one mistake because I'me made many .

Just a comment about eyebrows, I do find them more work than I expected and gradually kept thinning them to look more femme over a period of time . I then went to have my haircut , the female stylist cut my male hair very well but before I could stop her she trimmed and shaped my eyebrows before I could stop her but no way could I hide away . I'm so glad all that is behind me now , I trim and sahpe my brows as I choose .

[Joyce Swindell]

My wife and I were out to a "girls night out" with the local crossdressing group. We always start early and go out shopping or Mani/pedi's. I decided when the tech asked regular or acrylic polish. I thought... I've never had the acrylics so ok ... acrylics it is! Talk about time spent getting ready for Monday work in man mode! Holy crap was it tough to get off!

[AngelaYVR]

Hmmm, brows seem to be mentioned a lot! I always pluck mine (and they seem to have become permanently thin now) but I also trim them with a shaver using a 1/8 inch guard. Last December I went to trim them and after doing the right side I realized that I had forgotten the guard! No eyebrow at all!

Three minutes of panic later and I decided to completely shave the left one as well, have to be symmetrical you know. Pencilled them in and went out. But making it presentable on Monday morning? Oh what a head ache! Took three weeks to fully grow back in.

[Robertacd]

Hmm... This is a tough one because I learned my lesson by the time I was like 12 from getting into my mother's things.

So probably my biggest mistake was not putting my mother's things back exactly as I found them. So she knew that I was in her stuff, again and I would be in trouble...

After growing up in hiding, my adult life has been uneventful as a far as getting caught by my mistakes.

[Meghan4now]

Hmmm, brows seem to be mentioned a lot! I always pluck mine (and they seem to have become permanently thin now) but I also trim them with a shaver using a 1/8 inch guard. Last December I went to trim them and after doing the right side I realized that I had forgotten the guard! No eyebrow at all!

Three minutes of panic later and I decided to completely shave the left one as well, have to be symmetrical you know. Pencilled them in and went out. But making it presentable on Monday morning? Oh what a head ache! Took three weeks to fully grow back in.

Hey, wasn't that a scene from The Wall?

Is there anybody out there?

[Alice Torn]

Purging dozens of great dressers and skirts and tops, and all my heels. I could have sold some a consignment store and made money, and kept some.

[CrossKimmy]

Oh my gosh honey there are so many when I was younger and figuring this whole thing out. We all do foolish things when we first start our journeys.

Lots of times when I swore I could fit into a dress or skirt from my mother then I?d hear the heart stopping sound of a tear or rip. One time when I was younger, I tried on a pair of her panties that had these plastic sides on them. They were really cute but as soon as I got them on, one side ripped off!!!! OH MY GOSH!!! I was in trouble. I actually walked to the local store and bought some glue and fastened it back together. I buried the panties deep in her drawer and hoped she wouldn?t find them. I never heard about it. But I?m thinking she knew something was different.

[mattea]

I wear glasses, very bad eyesight, so I have my lady glasses and my drab glasses. the other day I get up go to work and realize I am wearing my lady glasses about halfway into my hour commute, I keep spares in my vehicle so I got lucky. Once I got to work I went to the bathroom after being there for about 20 minutes and realized I still had all four pink jewel earrings in! I got lucky that I beat everyone into the office, and didn't get caught! It was one of those mornings that I just wasn't thinking!

[Kelly-o]

Painted my toe nails and learned how observant my doctor was and how poor of a job I did at removing the polish completely. Oops. Well she did like the shade at least.

[Janine cd]

I once was totally dressed and had to respond to a call for help from my teenage daughter who was experiencing car trouble. I was able to change my clothes and remove my makeup, but was not able to remove all of the foundation. When I arrived at the scene to help, she noticed the remaining makeup and asked if I was O.K. My skin appeared pale and sickly. I tol her that it was only the beginning of a bad cold.

[Michelle43]

That happened to me so many times also, with her shoes specially.

[Lacey86]

I once took the whole day off of work to wait at home to sign for a package. Didn't have kids yet, so of course I got bored waiting and got dolled up. So pink fog took over and I lost track of time. Here I was with panties, skirt, heels, big old pushup bra, and a tight t shirt, when I hear a knock at the door.
I tore off everything as fast as I could and jumped into a pair of shorts. By the time I got to the door the delivery man was crossing the street back to his truck. I yelled and got him to come back, signed for my package, and apologized that I had been "asleep". In my rush I didn't have time to put on a shirt, but I was reasonably fit and I thought it wouldn't be a big deal. After I got my package and went inside only then did I realize I had super clearly defined lines on my chest in the shape of my pushup bra. I was mortified. I'm just glad I never saw that delivery guy again.

[Ericka_d]

I got lucky in the brow department. I have very fair color brows, and not super thick. First time I had them shaped. It looked more or less like a groomed male brow, as time as went on. They became more feminine. A few weeks ago they became they became feminine completely. I couldn't be happier, and no one has said a thing.

As for mistakes. I have bought clothes that just didn't look good on me, and had to get rid of them. I also spent a lot of money on foundation. Intil I found the right shade.

[Ressie]

Buying clothes that were too small (or too large). Did that mistake repeatedly!

Putting on rings before putting on nylons caused me to put a run in one of the stockings.

Answering the door in my bare feet. Forgot I had polish on my toenails and it was my uncle at the door.

[Crissy 107]

I once went to my Dr for a hip problem and never expected him to ask me to take my sneakers and socks off. I’m thinking damn, but I just did it and the Dr and his assistant, a female got to see my pretty pink toes. The Doc did not blink an eye but the assistant was smiling.

[CarlaWestin]

A couple do come to mind although, I've had plenty.

I work with a uniformed group in a facility and we enjoy breaks at large communal round tables.
After lunch one time a female coworker asked me why I was wearing clear nail polish.
Employing my natural rapier wit I said, "It keeps my nails from splitting. Besides, you're the only one who noticed!"
She replied, "Well, actually, I'm just the first person to ask you about it."

And then there was the time I had a quick appointment with the urologist. Pretty routine.
In the exam room it was the usual confirmation of the test results and no change in medication.
And then he said, "A quick prostate check and we're all done."
As I pulled down my pink and violet lace panties I swear I heard him snicker.

[emma30]

Kelly i painted my toe nails once with really cheap products and i worried so much cus it wouldnt come off 😢 i kept them covered for ages until it came off scary lol

[Dannigirl]

Tried using a Sharpie for eyeliner once, that was the stupidest thing I ever did (while dressing anyway) Rubbed my eyes raw getting it off.
Eyeliner seems to be my nemesis ... thought I had removed all of a beautiful dark blue eye liner once but apparently I hadn't and my GF at the time discovered the traces. That was the beginning of the end of that relationship. But the Sharpie eyeliner routine really was the dumbest thing I ever tried.

[Robertacd]

LOL, I am sorry Danni I just have to laugh at the Sharpie eye liner thing.

What was going through your head?

BTW: Eye liner is my nemesis too. So I just use black eye shadow instead. It's way more forgiving I can't get a precision line with my shadow brush, but I think it looks better because I can't get a precision line anyway using eye liner pencils, liquid, or marker types.

[Stephanie47]

When I was a teenager I was going to a physical for a summer job with United Parcel Service. I was home alone that day. The physical was in the afternoon. In the morning I was dabbling in my mother's lingerie draw and tried on and wore for some time her pull on open bottom girdle. It was very snug which left lines on my body from the seams on the girdle. I tried like heck to get rid of them by kneading my skin. I don't think I got all of the lines "erased" by the time I got to the physical. Obviously, the lines did not match the BVD's I was wearing. I didn't get the job.

[Cheryl T]

Biggest mistake...buying a cheap wig online and thinking it was good enough to wear out.
Now it's salon visits only. I want to feel it, see it, wear it and know it's right before I spend my money. Yeah, it can be scary the first time, but the people in the salons understand. They work with Cancer patients and others with special needs and they always have private rooms for people that want that security.

[Asew]

Nothing really sticks out to me as a mistake. When I first started buying stuff I would buy things that didn't fit well and such but I see that as a learning opportunity (luckily most of those mistakes were at thrift store prices so not too bad on the bank). But overall regarding my dressing my biggest mistake is not accepting this side of me but I feel like that is outside of the scope of the original question.

[Maria 60]

Had dressed a night before and it was late and didn't wash off my make-up, the next day at work I was sweating and I wiped my face with a white towel and the towel had all biege foundation all over it. I was wonder why everyone was asking if I went to a tanning bed.

[Jennifer in CO]

I'll add an agreement that picking one thing is almost impossible. One that sticks out however was I had been working on the car and ran to the parts store to pick up a part. Wife had braided my hair that morning as usual but in a French braid (this is before I transitioned). I'm standing at the parts counter getting what I need and noticed the counter guy kept looking at me kinda funny. I just thought the braid might have been too much. Got back in the car and glanced up in the rear view mirror. I was still wearing my 2" pink drop pearl earrings from the night before. They were so light I forgot about them...oops...

[alwayshave]

No major mistakes, though I have nor removed all my eyeliner in the past. Now I use eye makeup remover in addition to makeup wipes.

[Bobbi46]

Life is full of mistakes but also it is an ever lasting learning curve.

[BrendaPDX]

Using eyeliner and not having makeup remover to get it all off. I went to a party and the host spotted me right off from across the room.

[Amy Lynn3]

Makeup is my downfall also. I have been ask so many times....do you have lipstick on ? Do you have makeup on ? However, what burst my crossdressing bubble was I was getting out of the shower and the doorbell rang. I put on a pair of pants and ran to the door and opened it. There stood my grown son and he looked down and said...."nice nails. Dad". UGH !!

[Ameli]

My biggest mistake is not owning it earlier. I wish I would have owned it with my wife years earlier and I wish I would have owned it with myself decades earlier

[Judy-Somthing]

I went to pick up a girl I was dating and on the why I remembered I had a girdle on. I pulled into a parking lot and in the car had to remove my shoes and pants to get it off, close call.

One time I used Spirit Gum around the edges of my breast forms. Well they left two red circles on my chest then realized I had a physical exam the next day.
They were still somewhat noticeable when my female doctor examined me. I wonder what she thought.

[Amanda77]

There is a few of opportunities that i wish I would have taken with my mom, she knew i was crossdressing. First time was the neighbor sent over boxes of used clothes from her daughters and had the boxes sitting in the hallway bye my bedroom she told me to have a look and see if there was anything i liked i could have, i said not likely.
Another time just her and i (in my teens)whent shopping in the city, an hour and a half away i was getting some new boys underwear she asked if thats what i wanted or if i would prefer alternative kind indicating in the direction of the lady's department, i chickened out and said no they would be fine.
The last significant time i could have been more open to her was i was just out of school living at home and working for a landscaping company it was a rainy morning and boss called not to bother coming to work to wet, just my mom and i at home. I was in my room dressed up and someone was calling me about something and called three times. I would undress and get my drab clothes to go talk to them, which took a couple of minutes after the third call my mom said just come out dresses as i was and i won't say anything. Didn't get another call though, but likely would not have came out crossdressed anyway.
I often wondered what the outcome would have been like if i had not been scared out of my skin and took those opportunities.

[Jin Xer]

Hey girls.
What is the biggest mistake or regret you done while dressing or getting ready. I got my eyebrows waxed yesterday and they are way ott feminine I am trying to hide myself

LOL!! All the replies took me down memory lane, too many to count. But I'll go with the time I trimmed my eyebrows just a 'little' too much. I immediately regretted it, but thought 'I might as well enjoy it'. Shaved my arms that night too. At least I wore glasses to hide the obvious at work. And yeah, I captured my experience for posterity. :)

And a word of caution, to whom it may concern: Never mix vodka and scotch. I does not end well the next day.


My biggest mistake is not owning it earlier. I wish I would have owned it with my wife years earlier and I wish I would have owned it with myself decades earlier

'Nuf said.

[Princess Chantal]

My biggest mistake was following the advice from a transitioning friend early on in my crossdressing life. Her words and actions led me to stray away from what I enjoy wearing the most (hosiery and heels), stress over “passing” and have crossdressing overwhelm my life. The fun and enjoyment I had prior to accepting her “helping” hand had declined severely during that period.

[Jasmine Jones NZ]

My biggest regret was not making sure my wife knew sooner. I thought she kind of knew but didn’t want to discuss it or participate so I kept it hidden. As I found out last year when I made sure she knew and we dressed up together the reality was that she didn’t know. But she did mention there were a few times when she thought I had the remnant of makeup on.

There have been a few occasions that I’ve struggled with getting eyeliner off and had to use excuses such as wiping my eyes while working on the car.

[Pixie_94]

Even trying anything, since I ended up liking it.

[Jennifer in CO]

Amanda77 hit on something that was quite prevalent in my life as well. I have written a short story about how "Mom's Know". Mine sure did, and although we never talked about it in any way shape or form, she did her best to pave the feminine pathway I was walking down. Someday I'll post it somewhere, but it was mainly written to get it all out of my head, and in an indirect way, say thank you to her for understanding as best she could.

[abbiedrake]

Just the trials of 'girl adolescence' for me. Some of those early outfits... Ugh!

[kelliboots]

some high quality glittery eye shadow left distictive glitter on my cheeks and my wife spotted in the sun right away. Wow thinking on my feet for that one...yikes. lol

[wendy]

My first regret :
When I was a teen, I wore my mom's pink dress (long sleeve). I thought if I wore a long sleeve PJ top and scrunched up the bottom dress into my PJ pants, my mom wouldn't notice. When I went to talk to my mom, I lifted my arm and lo and behold, she saw the pink sleeve. At that point she knew I was a CD and I was afraid she would tell my dad, but she never did.

My 2nd regret, again as a teen, I wore my aunt's wedding dress. In my early teens I could fit, but only do up the back zipper half way. As I got older and bigger, I tried it on and in my struggle to zip up the zipper, I broke the seam on the zipper.

[Nicole Bernard]

Ok. I hope I can fit this all in. Here goes!

2nd time wearing my mom's makeup and almost got caught.

"Borrowed" my mom's nail polish. I think she saw me but didn't say anything.

Visited mom, with painted toenails and socks with holes in them. Tried to hide them the whole time.

Stole bronzer from grocery store.

Wore stolen bronzer all over my face and went to sporting event with my brother.

Wore foundation when my aunt and uncle came over.

Borrowed, and returned, makeup from coworkers desk.

Used makeup from roommates girlfriend.

Didn't clean off all eyeliner before wife came home.

Wore lipstick that leaves a pink hue after wiping it off.

Biggest mistake. Not being honest with my wife about my crossdressing.

[Allison Chaynes]

I assumed at my last CT scan that I would only be removing my shirt. I arrived, two very gorgeous blondes were the techs, and they informed me my pants had to come off but I could leave my underwear on. I was wearing nylon briefs with lace waistband. I said, oh hell, and went with it. Not like I was ever gonna see them again anyway. If there was laughing, I didn't hear it, they were professional.

[Teri Ray]

I have tons of crossdressing mistakes. Among them include numerous times of leaving some kind of women's item out (that of course I believed I had meticulously looked for) loose false nails, panties, stockings lipstick ect. Always seemed to find them laying out at unfortunate times

I too had an eyebrow mishap and trimmed way too much off one eyebrow. Being creative I came up with the ol "put too much charcoal lighter fluid on the grill and experienced a flashback that burned my eyebrows off." Kinda worked.

As others have stated I wish I had had the big talk with my wife sooner.

[TerryWa]

After a dress-up session, I thought I had removed the blush from my cheeks along with all the other femme traces. I didn't. I went to a corner store to get some coke and the man at the counter said, 'You're one of them aren't you?' I just had this blank stare because I didn't know what he was talking about - until I got home and happened to look at my reflection in the mirror. Oh well. Lesson learned.

[sophie p]

So many of us had eyebrow malfunctions and there is no hiding from it. I have also forgotten to take out female earrings on a few occasions nothing was said only love your earrings. I was so embarrassed

[Palaina Nocturnus]

I used to wear a lace bra with push up inserts to fill them. For the most part it looked very passable. Then I took a bunch of selfies and saw myself from the side lol I'm very lucky and happy my girlfriend went shopping with me and helped pick out an already stuffed bra for me.

I wear that bra daily when possible. I still wear the lace one when I'm under dressing. Wearing a bra and panties is pretty much a security blanket for me