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Thread: Biggest guilty pleasure of Crossdressing

  1. #26
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    As others have stated, I've tried to get over the guilt / shame of the crossing. Now I would say the guilty pleasure would be shopping and spending too much money on some nice clothes.

  2. #27
    Member Charlotte Haynes's Avatar
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    Mine is ABBA

  3. #28
    Member Monique65's Avatar
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    Shaving my face while wearing matching bra and panties.
    Honoring the woman within

  4. #29
    Member XemmaX's Avatar
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    learning to really not care what strangers think!

  5. #30
    Junior Member Alana Westenra's Avatar
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    Quote Originally Posted by Charlotte Haynes View Post
    Mine is ABBA
    Same! My biggest GP is the music I put on while dressed; stuff I'd never listen to otherwise!

  6. #31
    Super Moderator Raychel's Avatar
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    Biggest guilt pleasure for me would be the fact that I truly enjoy to be dressed in a dress and forms.
    And When I look in the mirror, I think I look better in a dress, then dressed as Ray
    my sister's reply when I told her how I prefer to dress

    "Everyone has there thing, all that matters is that you are happy, love what you do and who you do it with"

  7. #32
    Member Denice's Avatar
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    Quote Originally Posted by XemmaX View Post
    learning to really not care what strangers think!
    ^^^^^^This!!^^^^^^^^
    I'm a man. I like being a man. I also love wearing women's clothing. It's my way to show honor, respect and solidarity with them.

  8. #33
    Member falcongts's Avatar
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    meeting a guy while dressed was wearing this had a great time but he moved away would like to try again sometime
    IMG_1977.jpg

  9. #34
    Aspiring Member April Rose's Avatar
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    Even though I dress practically every day at home I am not out to more than a few people. If there weren't a degree of embarrassment or shame still surrounding it, why am I not out to everyone? So I think my guilty pleasure is crossdressing itself.
    I am a vessel of the goddess. Let me express my calling to a feminine life through nurturing love and relatedness.

  10. #35
    Member KatieV's Avatar
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    Being hit on by Black men. It happens quite often, I do not know why. Walking down the street, driving in my car. They compliment me, ask me if I?d like to join them for a drink, try to pick me up. I have always said no ? but I am flattered!

  11. #36
    Junior Member Just Dana's Avatar
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    Mirrors.
    The avatar? Yeah, that's definitely FaceApp. Incognito, right?

  12. #37
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    Having way too many options of cute clothes to shop and spend money on. Guy's clothes are so boring in comparison.

  13. #38
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    I'm not out to my wife, so everything crossdressing is a guilty pleasure for me. That said, my greatest guilty pleasure is shopping for womens clothing and makeup and CD accessories online. I love looking at all the options and colors and styles.

  14. #39
    Aspiring Member DanielleDubois's Avatar
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    My guilty pleasure is looking into the mirror on one my Danielle boudoir/lingerie days and seeing a woman staring back at me... well, if I squint my eyes a lot

  15. #40
    Member MiniRock's Avatar
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    Quote Originally Posted by alwayshave View Post
    I have not felt guilty about my dressing in a long time. But my guilty pleasure would be open bottom girdles.
    Ooh yes please!

  16. #41
    Aspiring Member SaraLin's Avatar
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    Probably my biggest GUILTY pleasure - is this forum.
    My wife doesn't want me "talking" to others about this part of me, but I know that if I don't vent somehow, I'll have a melt down.

    Being among friends - even if only virtually - really helps me maintain balance.

  17. #42
    Senior Member Davina2833's Avatar
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    Hi Minirock and alwayshave,

    We could always start a club...

    Davina

  18. #43
    Junior Member Erin Lafleur's Avatar
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    Quote Originally Posted by MiniRock View Post
    Ooh yes please!
    Just ordered my first vintage open bottomed girdle today, can't wait! I love pretty, lacey garter belts but they're just not up to the task (even with stayups).
    Lace top nylons are one of my favorite items to wear but also my nemesis and I refuse to give up without a fight!
    Kindness is the language which the deaf can hear and the blind can see.

  19. #44
    Junior Member JustJennifer's Avatar
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    Quote Originally Posted by Charlotte Haynes View Post
    Mine is ABBA
    Their new single "Don't Shut Me Down" has been playing in a loop in my head for weeks now...

    And now you see another me, I've been reloaded!
    I'm fired up, don't shut me down!

  20. #45
    Aspiring Member MonicaPVD's Avatar
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    Happens a lot. I have a theory, and it is a combination of two factors. First, the fact that crossdressers and transwomen are endlessly fetishized in the media and degraded by porn tropes. Second, the fact that urban black men tend to be a lot more at ease with exploring their sexuality ON THE DOWN LOW. What does this mean? Many guys see a crossdresser and instantly think, "easy sex". Black men, in my experience, are more likely to verbalize that thought than white men.

    Quote Originally Posted by KatieV View Post
    Being hit on by Black men. It happens quite often, I do not know why. Walking down the street, driving in my car. They compliment me, ask me if I?d like to join them for a drink, try to pick me up. I have always said no ? but I am flattered!

  21. #46
    There's that smile! CarlaWestin's Avatar
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    Being in the company of a sexy hot woman that know's what I'm thinking.
    And she's within reach and doesn't mind.
    I've waited so long for this time. Makeup is so frustrating. Shaking hands and I look so old. This was a mistake.
    My new maid's outfit is cute. Sure fits tight.
    And then I step into the bedroom and in the mirror, I see a beautiful woman looking back at me.
    Smile, Honey! You look fabulous!

  22. #47
    Life is more fun in heels Genifer Teal's Avatar
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    I do not believe the title is meant to suggest the same kind of guilt we often associate with dressing. For me an answer might be regular mani - pedi appointments.

  23. #48
    Member Alexis00's Avatar
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    Biggest? Big (D) boobs!

    And obsessed with bras. First bought unwired bras. Then padded cup bras. Then sports bras. Then underwire lace bras. Then lace cup bras without wires with small cups for underdressing. Then lace cup bras with wires with small cups to try and give me some shape without forms for underdressing.

    Now Obsessed with matching bra and panty sets.
    Last edited by Alexis00; 11-04-2021 at 11:36 AM.

  24. #49
    Member MiniRock's Avatar
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    Quote Originally Posted by Davina2833 View Post
    Hi Minirock and alwayshave,

    We could always start a club...

    Davina
    Let's start a picture thread Davina. Erin can be first because she already has one. And of course Jamie. I'll have to get one and it'll have to wait until I get back to Vienna at Christmas where all my things are. But I'll definitely post in due course.

  25. #50
    Sarah Adams Vintage4sarah's Avatar
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    There are so many guilty pleasures that all of you wonderful ladies are sharing that so many of us can relate to while enfemme. I certainly can share with many of you. But, my greatest pleasures are based around doing my best to create my female image and then be out and about in public settings or other venues with other Tgirls, real woman or those special gentlemen admirers. Having dinner with a special gentleman, chatting, strolling arm and arm, and having the sensation of being treated like a woman would be at the top of the list.
    Sarah Adams, mature girl from NH. My photos are on Flickr under vintage4sarah !

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