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Thread: Mistake

  1. #26
    Member Dannigirl's Avatar
    Join Date
    Mar 2006
    Ontario, Canada
    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.

  2. #27
    Seňora Member
    Join Date
    Nov 2004
    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.

  3. #28
    Platinum Member
    Join Date
    Oct 2010
    Western Washington
    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.

  4. #29
    Exploring NEPA now Cheryl T's Avatar
    Join Date
    Feb 2006
    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.

  5. #30
    Senior Member Asew's Avatar
    Join Date
    Jan 2018
    Rochester, NY
    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.

  6. #31
    Silver Member Maria 60's Avatar
    Join Date
    Sep 2010
    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.

  7. #32
    Senior Member Jennifer in CO's Avatar
    Join Date
    Jun 2004
    Rocky Mountains
    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...

  8. #33
    Gold Member alwayshave's Avatar
    Join Date
    Dec 2011
    Washington, DC
    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.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  9. #34
    Silver Member Bobbi46's Avatar
    Join Date
    May 2015
    France, Villessot near St Christophe
    Life is full of mistakes but also it is an ever lasting learning curve.
    I started life a lost man now I am a found woman

  10. #35
    Senior Member BrendaPDX's Avatar
    Join Date
    May 2016
    Portland, Oregon
    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.

  11. #36
    Silver Member Amy Lynn3's Avatar
    Join Date
    Aug 2007
    North Carolina
    Makeup is my downfall also. I have been ask so many 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 !!

  12. #37
    Member Ameli's Avatar
    Join Date
    Jun 2010
    Saskatoon, Canada
    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

  13. #38
    Miss Judy Judy-Somthing's Avatar
    Join Date
    Dec 2015
    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.
    Last edited by Judy-Somthing; 09-26-2019 at 10:30 PM.
    "This is ME" I am not CRAZY, I'm just a GUY who likes dresses!
    Since allot of men dress up in woman's clothing that makes it a manly thing to do!
    Much more fun than fishing.
    I do construction like house building and I love CD-ing, what's the difference?

  14. #39
    Junior Member Amanda77's Avatar
    Join Date
    May 2015
    Small town south Central Manitoba Canada
    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.
    Last edited by Amanda77; 09-20-2019 at 06:27 PM.

  15. #40
    Colorado Country Girl Jin Xer's Avatar
    Join Date
    Jul 2009
    Quote Originally Posted by sophie p View Post
    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.

    Quote Originally Posted by Ameli View Post
    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.

  16. #41
    BEING YOUnique is AWESOME Princess Chantal's Avatar
    Join Date
    Jul 2008
    Winnipeg, MB, Canada
    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.

  17. #42
    Member Jasmine Jones NZ's Avatar
    Join Date
    Mar 2011
    New Zealand
    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.

  18. #43
    Sort of a n00b Pixie_94's Avatar
    Join Date
    Aug 2017
    Costa Rica
    Even trying anything, since I ended up liking it.

  19. #44
    Senior Member Jennifer in CO's Avatar
    Join Date
    Jun 2004
    Rocky Mountains
    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.

  20. #45
    Aspiring Member abbiedrake's Avatar
    Join Date
    Dec 2018
    Just the trials of 'girl adolescence' for me. Some of those early outfits... Ugh!

  21. #46
    Member kelliboots's Avatar
    Join Date
    Sep 2008
    Los Angeles
    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

  22. #47
    Aspiring Member
    Join Date
    Mar 2005
    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.

  23. #48
    Junior Member
    Join Date
    Jan 2019
    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.

  24. #49
    Senior Member Allison Chaynes's Avatar
    Join Date
    Oct 2012
    Knoxvegas, TN
    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.
    Life is too short to be boring.

  25. #50
    Rural T Girl Teri Ray's Avatar
    Join Date
    Jun 2008
    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.
    Teri Ray Rural Idaho Girl.

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