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Thread: Biggest guilty pleasure of Crossdressing

  1. #1
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    Biggest guilty pleasure of Crossdressing

    What is your biggest guilty pleasure in crossdressing?

    SJ

  2. #2
    Sort of a n00b Pixie_94's Avatar
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    Simply wanting to do it.

  3. #3
    Platinum Member kimdl93's Avatar
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    I really, really have been trying to set-aside the guilty part . As far as pleasures go, what I enjoy most is comfortably being out in the real world

  4. #4
    Member Kris Burton's Avatar
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    Quote Originally Posted by Pixie_94 View Post
    Simply wanting to do it.
    That, and the erotic pleasure I would experience while dressing. I thought it so wrong so taboo. I have successfully put those things aside, and it feels even better. Now however, the outside world beckons...

  5. #5
    Silver Member franlee's Avatar
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    I haven't felt guilt in years. And I can't even remember exactly what is was based in other than using my wife and female friends or family's clothes and that really didn't bother me that much back then. Now if anything it's for not indulging more.
    [SIGPIC][/SIGPIC]Fran
    It's worth something just being around to Fuss!

  6. #6
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    I used to feel guilty wearing feminine dresses and wigs and makeup because I thought that was unnatural. I have since accepted the reality that my desire to dress totally as a woman is only a necessary part of my being.

  7. #7
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    Breast forms and painted nails...

  8. #8
    Miss Conception Karren Hutton's Avatar
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    The simple pleasure of wearing D cup bras and not needing breast forms!

  9. #9
    Member GenevieveF's Avatar
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    The feeling I get when I slip on a pair of stilettos.

  10. #10
    Member Debs's Avatar
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    Walking into my favourite bar, all looking at me and they smile, I know I'm safe dressed and feel a million dollars

  11. #11
    New Member CamillaH's Avatar
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    Talking to my wife on the phone while dressed

  12. #12
    Aspiring Member MonicaPVD's Avatar
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    Wearing a very tight and sexy outfit in public that is completely out of place for the occasion. Not something I do much at all, but a wonderfully guilty pleasure.

  13. #13
    Paula Paula_56's Avatar
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    Getting dressed to the nines in a business suit, and then slipping my stocking clad feet into a pair of pumps.

    The feeling you get when you put a dress on over your head and falls down around your breats and lingerie,

  14. #14
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    Well, it is definitely a thing in the past and definitely off the shelf in the future. When our daughter lived out of state my wife would visit her for seven to ten days. Now our daughter lives forty miles away. She would also visit her cousin in Arizona for a week. Now, her cousin lives in a care facility. No more trips. When she traveled I was able to hang a nice selection of dresses and slips in the walk-in closet; line up heels at the foot of the bed; stock panties and bras in my armoire. It was 24/7 and evening drives and strolls. Pre-Covid my wife did babysit overnight at our daughter's apartment. Covid has killed even that opportunity.

  15. #15
    Just finding my way.... StaceyJane's Avatar
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    Putting on a bra that fits without forms or stuffing.
    Stacey

    I'm not a doctor, I just play one on TV.

    http://www.youtube.com/watch?v=Wob7zmvVTb8

  16. #16
    Member Debs's Avatar
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    Stacey, Ive got one of them, amazing, and where the hell do i get another one ?

  17. #17
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    The fact the my wife seeing me in panties turns her on a much as she turns me on. We lounged around the house all weekend, just us , in our panties. It was splendid!

  18. #18
    Member Lori Ann Westlake's Avatar
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    I fortunately succeeded in dumping the "guilt"--or rather, the shame--decades ago. But... greatest pleasure? Today I'd say it's fantasizing while dressed as a woman.

    In years long past, especially in my teens when my dressing was more fetish-oriented than it is today, there was one supreme pleasure I remember. I would get completely dressed in a bra, garters, nylons and heels, slip, skirt and blouse--everything, in short, except the panties. Then, feeling "almost" dressed, I would delight in slipping the cool, silky panties up my nylon-clad legs, drawing them up underneath me and settling them around my waist. fully dressed now in women's clothing and women's underwear. I was "saving the best until last," as it were. It was always a delicious moment.

  19. #19
    Weirdest woman ever! docrobbysherry's Avatar
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    It USED to be the sex!

    But, since I'm 78 now? I consider ANY sex to be a good thing!
    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!

  20. #20
    Senior Member mbmeen12's Avatar
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    What is your biggest guilty pleasure in crossdressing?
    Impure thoughts.....
    Escapism isn't necessarily bad, but is definitely unhealthy in the long term. While helpful in the short term, things will degrade over time. At some point, the escapee will have to face the issue. Things simply blowing over isn't really going to happen in many situations.

  21. #21
    Member Kelli_cd's Avatar
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    It would be that I just feel "good" or "better" when I'm in bra and panties.
    Self confidence has never been an issue, but I seem to have more when I'm wearing.
    In earlier years, the sexual desires were a driving factor. Now, well, this is just me, and I'm happy with me.

  22. #22
    Gold Member alwayshave's Avatar
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    I have not felt guilty about my dressing in a long time. But my guilty pleasure would be open bottom girdles.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  23. #23
    Member Monique65's Avatar
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    Standing in front of a full length mirror admiring the reflection of a beautiful woman.
    Last edited by Monique65; 10-06-2021 at 08:09 AM.
    Honoring the woman within

  24. #24
    Aspiring Member josie_S's Avatar
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    I feel a little sheepish saying this, but the way my butt POPS when I put on heels, especially in skirts

  25. #25
    Senior Member NancySue's Avatar
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    I?ve been dressing for so long, I have absolutely no guilt feelings. Even after all this time, like Stacey Jane, I experience pleasure daily when I put on my bra that fits perfectly with no forms or padding. Slipping on my panties and thigh highs is very nice, too.

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