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Thread: The Biggest Leap

  1. #1
    Senior Member JocelynJames's Avatar
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    The Biggest Leap

    Tonight , I took what I consider to be the biggest leap during my crossdressing years besides telling my wife. I was getting a haircut and have talked(mostly to myself) forever about getting my wigs pro styled. I previous texted my barber with ? hey, I have a friends that wears a lot of wigs. Do you also cut those?? To which he replied ?yes?. That was probably six months ago?.I know, snails pace. Anyways , I asked him if he remembered that convo , he did?.to which I replied? I?m the friend?.I?m a part time Crossdresser ? his jaw hit the floor. He said he NEVER would have guessed. Then I said it was in my truck to which he replied? you better get that thing in here!? I always felt I could trust him. He worked on it a bit while I was there, but had another appointment coming soon, so he?s going to finish it up tonight and tomorrow. I told him to take all the time he needs. I?m so excited. Besides people here and my wife, I’ve never told another soul. Thanks for reading
    Last edited by JocelynJames; 07-10-2025 at 07:10 PM.
    ~Joss
    ?To become the queen, I first honored the princess within?curious, delicate, and brave. Every step I take, every thread of silk I wrap around me, is a coronation of my truth.?

  2. #2
    Moderator Crissy 107's Avatar
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    Joss, Good for you girl, you know him and you trust him, so far everything is good. Let us know what if anything he says when you get it back.
    One question, were there other barbers or customers present?
    Crissy

  3. #3
    Silver Member Sandi Beech's Avatar
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    Good for you. It is a big step, but it does get a lot easier opening up to others over time. It can actually start up some fun conversations.

    Sandi

  4. #4
    Senior Member JocelynJames's Avatar
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    Crissy,
    He runs out of his house, was previously at a ?big chain? and has his own shop in another city
    Last edited by JocelynJames; 07-11-2025 at 05:06 AM.

  5. #5
    New "old" girl Suzie Petersen's Avatar
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    That is exciting, Jocelyn!
    Telling someone else about your dressing is probably the biggest deal, I would think, but having your wig professionally done is definitely exciting too.
    What did you ask him to do with it?

  6. #6
    Member Charlotte Sparkle's Avatar
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    Good one Joss. I hope he does a good job of styling it for you and you are happy with the end result.

  7. #7
    Gold Member Helen_Highwater's Avatar
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    From my own experience I would say getting a wig styled needs it to be on your head when taking place. Earlier in the year I had a fringe cut into a neck length Bob style wig. The stylist insisted that I was wearing it while she did the cutting which is how I thought it would be done anyway.

    It was the usual sort of encounter you get at the hairdressers. General chitchat, how long do you want it, holidays etc. She did emphasise that she'd do the work but at my risk. Unlike real hair, it won't grow back so if at the end I didn't like it, that was a risk I'd be taking.

    She charged me 5 pounds but as she'd seen me as a walk-in with no appointment and been lovely to me throughout I gave her 10 which I think made, if not her day, her afternoon.
    Who dares wears Get in, get out without being noticed

  8. #8
    Connie Connie D50's Avatar
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    Wow good for you taking that big leap.

  9. #9
    Platinum Member alwayshave's Avatar
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    Joss, That was gutsy. Good on you.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  10. #10
    Member susann_gardener's Avatar
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    Big leap, Jos. And you thought I was getting out!
    My wig really needs a trim to compliment my face, not hide it. However, as my wife is my hairdresser (there's not a lot to cut), that won't happen.
    Susann_Gardener

  11. #11
    Exploring NEPA now Cheryl T's Avatar
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    Good for you. Nerve wracking I'm sure.
    I remember when I decided to go to a wig shop and buy a nice wig. The lady at the counter was about my age and she asked how she could help. I just said "I'm a crossdresser and I want a nice wig". What a relief after getting those words out.
    I don't wear women's clothes, I wear MY clothes !

  12. #12
    Just can't help myself! Brenda456's Avatar
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    Nerves of steel! Nice job. Enjoy the wig!

  13. #13
    Life is more fun in heels Genifer Teal's Avatar
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    Always awkward expanding the closet. The more people that know, the more people that can find out. Seems like you made a wise choice.Seeking the right person for help. Styling a wig is so important and so overlooked. It will make a huge difference.

  14. #14
    Member Meg's Avatar
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    Good for you girl! Definitely a leap of faith. Not sure I would have been able to do the same thing. Perhaps with a stranger out of town who doesn't know me, but not sure I could have pulled that off with someone I interact with on a regular basis. I am proud of you. Hugs, Meg

  15. #15
    Seasoned Member Rhonda Darling's Avatar
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    I admire you courage having a male barber style a female wig. I would have gone to a salon and had a female stylist do it. But that is just me.

  16. #16
    Senior Member JocelynJames's Avatar
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    Not revealing too much, but this guy worked at a chain(I said that) and does male and female cut/style. Just my guy self referring to him as my ?barber?.
    ~Joss
    ?To become the queen, I first honored the princess within?curious, delicate, and brave. Every step I take, every thread of silk I wrap around me, is a coronation of my truth.?

  17. #17
    Happy 2 B Here Mercedes's Avatar
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    Well done on the leap! And so happy to hear there was complete acceptance. I hope your next conversation with the stylist is even more positive.

  18. #18
    Senior Member Fiona_44's Avatar
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    Felt good telling someone about the real you, didn't it?
    "Care about what other people think of you and you will always be their prisoner" - Lao Tzu

  19. #19
    Platinum Member kimdl93's Avatar
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    After a lifetime of hiding oneself, it takes a certain amount of courage to trust anyone with the information.
    O wad some Pow'r the giftie gie us
    To see oursels as ithers see us!

  20. #20
    Senior Member Debbie Denier's Avatar
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    Thats brilliant Joss. You must feel like you are walking on the moon.

  21. #21
    Senior Member Heather76's Avatar
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    WOW!!! What nerve. I cannot imagine having that conversation with my barber. I envy you feeling comfortable enough to come out to others.
    It's never too late to enjoy a happy childhood.
    Live each day as though it's your last 'cause one day you'll be right.
    I'm finding the more feminine side of me...and I ❤️ this adventure.

  22. #22
    Hot Geezer Girl docrobbysherry's Avatar
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    Indiana Jones would be prouidv of u, Joss. Leap of faith and all!

    My daughter was hair dresser for 10 years. She knows about my dressing. But I haven't even asked her to style/trim my wigs.

    Instead, when I want a different style, etc? I just change wigs!
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

    Challenge yourself and pursue your passions! When your life clock runs out, you'll have few or NO REGRETS!

  23. #23
    Aspiring Member LelaK's Avatar
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    Did you also mention that you're not gay? My exGF thought I was gay or bi because of my crossdressing. I think people generally assume you're gay if you crossdress.
    Last edited by LelaK; 07-13-2025 at 07:42 PM.
    T-shirt says: "Hi, I Crossdress!"

  24. #24
    Senior Member JocelynJames's Avatar
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    Lela: good point. I feel like it?s been heavily inferred, as he?s cut my hair for 6 or 7 years now, knows of my kids , wife, X wife, but it hasn?t been explicitly stated. Probably at some point I?ll have to set the record straight, as people not in the know don?t realize the spectrum cd/TG covers. He did text me last night and say it was just about ready . I had shared the pics from my Saturday meetup and he liked the whole look.
    ~Joss
    ?To become the queen, I first honored the princess within?curious, delicate, and brave. Every step I take, every thread of silk I wrap around me, is a coronation of my truth.?

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