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Thread: Biggest guilty pleasure of Crossdressing

  1. #51
    Silver Member Maria 60's Avatar
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    I believe mine would be sitting on the couch and watching TV with my wife. Turning to her and give her a smile and she smiles back and then I look down and see that I'm wearing a full slip nighty with thigh highs bra and breast forms and a silk pink robe. Still after all these years in great disbelief and guilty pleasures.

  2. #52
    Seasoned Member Rhonda Darling's Avatar
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    Inhaling that fresh air of heady expectation . . . and
    Exhaling that sweet sweet breath of sublime joy and satisfaction.
    There?s nothing else like it.
    ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
    Be all the woman that you can be!
    ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
    . . . and now, On With The Show!

  3. #53
    Silver Member prene's Avatar
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    My breast forms?
    I have some but not big enough.

    Prene

  4. #54
    Oh to be an English Rose Jane G's Avatar
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    Switching from plain Jane to sexy Jane. I'm very comfortable with my dressing it's just part of life, but every now and again there are special moments that still are guilty pleasures.

  5. #55
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    seeing toe nails with polish; shaved legs in nylon under a skirt or dress or shorts ; a nice top or blouse and know that I'm viewing MYSELF not somebody else.
    Pink is more than a color: its an attitude!

  6. #56
    Silver Member Natalie5004's Avatar
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    Your avatar shows that you are well endowed, Prene.

  7. #57
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    Beautiful/romantic/bridal lingerie & sleepwear. Nothing like it.

  8. #58
    You Can Call Me Christy G
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    Quote Originally Posted by Karren Hutton View Post
    The simple pleasure of wearing D cup bras and not needing breast forms!
    The brassiere I'm wearing at the moment has C cups that hold and shape very real breasts and the pleasure you feel is one I enjoy immensely. I love the look and the feel. I always thought of myself as a breast man... only half aware that I enjoyed putting on my own brassiere as much as I enjoyed taking my partner's brassiere off. What a strange world this is.
    We shall not cease from exploration, and the end of all our exploring will be to arrive where we started and know the place for the first time...
    T.S. Eliot Four Quartets

  9. #59
    Senior Member Linda K.'s Avatar
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    Being able to stay dressed for hours. I am most comfortable and relaxed when I am dressed.

  10. #60
    Member Christina89's Avatar
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    Being able to come home after a long g work day or regular work day and just putting on a look or pj's and feeling nice and relaxed. Feeling my issues and anxiety go away

  11. #61
    Senior Member DianeT's Avatar
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    Watching my legs with heels on the table while lounging and watching TV. So superficial, and yet it entertains me to no end.

  12. #62
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    Seeing the woman staring back at me in the mirror, the care and time my wife puts into making sure every part of my makeup, hair and outfit is just right, and the feeling when she makes me "feel like a woman"!
    Last edited by char GG; 10-31-2021 at 09:21 PM. Reason: Topic not allowed

  13. #63
    Junior Member denese's Avatar
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    would love to message or email . i am in copperas cove

  14. #64
    Once upon a time... Veronica Lacey's Avatar
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    The term "guilty pleasure" I read as not actually feeling guilty for doing so but more that if my wife or anyone else (hypothetically) said hey, you really like this I'd respond Yes, guilty as charged.

    So such guilty pleasures include when I have opportunity to put out all my wardrobe in the closet, armoire, dresser, heels on display; I really love that. Having a chat on the phone with people while fully dressed. Forgetting to change out of panties when going out in male mode.

    These are just everyday things that remind me that my dressing is normal and unnoticed.

  15. #65
    Platinum Member Beverley Sims's Avatar
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    There is no guilt in my dressing just pleasure.
    Work on your elegance,
    and beauty will follow.

  16. #66
    Aspiring Member kellyanne's Avatar
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    No guilt in my pleasures - I am what I am so I never feel guilt about dressing in panties or in full en femme.

    We had boozer's for parents so if I imbibe which I rarely do - that makes me feel very guilty.

  17. #67
    Member jamienoir's Avatar
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    Quote Originally Posted by MonicaPVD View Post
    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.

    Hey! Never had a black dude hit a me! What gives...

    It's usually white dudes lol.
    Last edited by char GG; 11-04-2021 at 02:08 PM. Reason: Duplicated comment

  18. #68
    Aspiring Member SarahLynn's Avatar
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    Jamienoir, "Hey! Never had a black dude hit a me! What gives... It's usually white dudes lol."

    Must be the reverse effect. White men thinking you are a loose woman. Not sure if that is a compliment. Have to admit, if I saw you out and about, and all by yourself, there is a very good chance I'd hit on you too.


    If I looked as good as many of you do in your avatars, that would be a pleasure for me. Not being the case, my guilt is my envy of your great looks.
    Last edited by SarahLynn; 11-04-2021 at 02:13 PM.
    Great leaders are not great because of their words or deeds but because of the greatness they inspire from others."
    (Legends of the StarDancer)

  19. #69
    Member Iris Tse's Avatar
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    Being propositioned by a hot bi-couple for a night of debauchery after a few drinks at my fave bar!

  20. #70
    Banned Read only
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    Quote Originally Posted by jamienoir View Post
    Hey! Never had a black dude hit a me! What gives...

    It's usually white dudes lol.
    Maybe you need to hang out in more diverse areas. 😂

  21. #71
    Member jamienoir's Avatar
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    Monica:

    I know right lol.
    Last edited by char GG; 11-04-2021 at 09:46 PM. Reason: No need to quote the post directly before yours.

  22. #72
    🙊🙈🙉 Patience's Avatar
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    1) Getting a makeover (had 3 so far),
    2) Shopping for a wig enfemme while made over, perhaps with the help of a friend,
    3) Walking around unapologetically, perhaps enjoying a public event, not giving a toss to what people may think.

    ...in that order.
    When haters hate, I celebrate!

  23. #73
    Member Mackem Sue's Avatar
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    Just the pure contentment I get from it.

    A specific pleasure?

    Taking a fresh pair of stocking out of their packaging, rolling them up to slide onto my legs, then slowly pulling them on, over my toes and ankles, up my calves, over my knees and finally up my thighs until they can go no further, followed by fastening to the clips of my suspenders and knowing that slight pleasant feeling as the suspenders occasionally tug on the stocking tops as I walk around in my heels.

    Sorry, couldn't resist being a tease. 😀

    Sue
    Last edited by Mackem Sue; 12-02-2021 at 05:08 AM.

  24. #74
    Gold Member Sometimes Steffi's Avatar
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    Sleeping in a bra with forms.
    Hi, I'm Steffi and I'm a crossdresser... And I accept and celebrate both sides of me. Or, maybe I'm gender fluid.

  25. #75
    Aspiring Member KymG's Avatar
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    Checking myself out in the mirror, and looking down to see the girls on display.

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