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Thread: A crossdresssing conundrum

  1. #26
    Member AvidFan's Avatar
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    My GF tried to do this many times. I feel stupid now for saying no all those times. Back then, I resisted all urges to dress.
    Now she gets mad if I dont let her do my makeup
    My GF calls me Sasha since being lost in the fog

  2. #27
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    So, this morning when I called her I told her I thought about it and changed my mind. Told her that the time before, it was due to a lost bet (and just for clarification, that never happened). Its going down Sunday afternoon.

  3. #28
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    OK, now Marissa please resist the temptation to disguise, hide or deny your interest. I know, its scarry, but with risk lies opportunity. Don't worry about presenting some fake masculine bravado...or somehow pretending it doesn't mean anything to you. Be honest and open.

    A while back I had my first pedicure with my wife - my initial instinct was to deny that it was fun, pretend that I was indifferent, and refuse to chose color. fortunately, I let the guy thing go, had a wonderful time and left with the cutest pink toenails.

  4. #29
    Platinum Member Eryn's Avatar
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    Quote Originally Posted by Matt2Marissa View Post
    So, this morning when I called her I told her I thought about it and changed my mind. Told her that the time before, it was due to a lost bet (and just for clarification, that never happened). Its going down Sunday afternoon.
    OK, we'll accept that little white lie to save face, but please, be honest with her about your true interest. Two things might happen.

    1) The relationship blows up in your face, which would have happened down the road anyway when she found out.

    2) The relationship blossoms and becomes a lifelong acceptance of the true you.

    I think that in this case honesty is well worth the risk!
    Eryn
    "These girls have the most beautiful dresses. And so do I! How about that!" [Kaylee, in Firefly] [SIGPIC][/SIGPIC]
    "What do you care what other people think?" [Arlene Feynman, to her husband Richard]
    "She's taller than all the women in my family, combined!" [Howard, in The Big Bang Theory]
    "Tall, tall girl. The woman could hunt geese with a rake!" [Mary Cooper, in The Big Bang Theory]

  5. #30
    A Silly Banana Haley Heather's Avatar
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    Quote Originally Posted by Matt2Marissa View Post
    So, this morning when I called her I told her I thought about it and changed my mind. Told her that the time before, it was due to a lost bet (and just for clarification, that never happened). Its going down Sunday afternoon.

    I hope you both have a great time.
    xoxo

  6. #31
    the happy camper
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    We'll be expecting a complete account, Penthouse letter style.

  7. #32
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    Quote Originally Posted by Sophie86 View Post
    We'll be expecting a complete account, Penthouse letter style.
    Will do, but not Penthouse letter style. I do not read, watch, or look at porn. I never have and never will.

  8. #33
    1st & 4th makeover pics Misti's Avatar
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    Save lots of $$$ in your first makeup

    Quote Originally Posted by BLUE ORCHID View Post
    Hi Marissa, Run don't walk back and say yes to a makeup.

    Orchid
    Besides, what the hey! It will save you lots of $$$ in your first makeup. So, what's to lose? Like everyone has said, "Do it!"

    BTW Afterwards, you'll be chomping at the bit for Amy at Glamour Boutique 2 (here in Vegas) to perform her artistry on you by the time you get here! What'a thrill! HeeHee!

  9. #34
    New Member Bree in Blossom's Avatar
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    It sounds like a wonderful offer, I say go for it. I'd love to find a partner who offered such encouragement -- you're lucky to have someone who sees the girl inside you. I understand your nervousness, but she seems like a supportive girlfriend. On a more practical note, she's offered a complete makeover for free -- I've been pricing transformation services online, and they're not cheap -- think of the money you'll save!
    Hugs & Hope,

    Bree in Blossom

  10. #35
    CDsteph cdsteph's Avatar
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    A dozen years ago, my SO asked the same question..... which made it easy to 'suddenly' enjoy crossdressing as The experience caught on..... didn't need to explain about my dressing for years previous ......

    Rush to the phone and accept the offer.... before every girl here beats you to it!

  11. #36
    naughty nurse Billie Jean's Avatar
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    The best I ever looked was when my ex wife did my makeup. I have always wishe she would do it for me again. I have the fashion sense to pick the right outfit but I haven't been able to get my makeup on as well as when she did it and I have tried to match everything she did. Billie Jean

  12. #37
    Super Moderator Raychel's Avatar
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    I think that you tell her about the real you. I would hope that she would accept you and then you can truely enjoy the makeup session.

    Eithetr that or tell her taht you were talking to a friend about this and he wants to give it a try. PMme for my ophone number, I will volunteer
    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"

  13. #38
    The Girl Next Door Sally24's Avatar
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    Tell her you didn't like the first time because you looked like an ugly girl. That will challenge her to make you look as pretty as she can!
    Sally

  14. #39
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    I had this happen to me at least a couple of times--once in childhood, when a girl wanted to put me, my little brother and her little brother all in her dresses and parade us in front of our mothers, and I declined because I already knew my secret and feared I would enjoy it too much and give it away, and a time or two in college, when another girl suggested I'd look cute dressed as a girl and I declined because my then-GF, who was aware of at least my underdressing and a few other girly things I'd been trying (e.g., painting my toenails) did know my secret. During part of my college years I also had longish hair that I wore in a ponytail (a small rebellion on a conservative campus), and lived in a coed dorm--some of my female friends would occasionally French-braid it for me, which I loved because it was girlish and because I loved the attention.

    Make no mistake, girls have a way of knowing when you have a feminine side you're trying to hide, so if she's willing to be playful about it and dress you up or make you up, go along with it.

  15. #40
    Skinny Bitch Comet's Avatar
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    If you're into the idea ... do it! Don't let the chance pass you by.

  16. #41
    Skinny Bitch Comet's Avatar
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    Quote Originally Posted by Sally24 View Post
    Tell her you didn't like the first time because you looked like an ugly girl. That will challenge her to make you look as pretty as she can!
    And this is a brilliant way to phrase it!

  17. #42
    Silver Member darla_g's Avatar
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    Quote Originally Posted by Stephanie Miller View Post
    Well, I think you should put on yur big girl shorts on
    shouldn't that be big girl panties?

  18. #43
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    Quote Originally Posted by Sally24 View Post
    Tell her you didn't like the first time because you looked like an ugly girl. That will challenge her to make you look as pretty as she can!
    Oh that's good!

    And don't forget to dress pretty too.

  19. #44
    sissy maid
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    the worst thing a person can do, is not take advantage of opportunity. You have to remember that this is supposed to be fun, and the best way to have some, is plug your nose, and jump right into the pool.

    If you do not, your mind will wonder what could have been for years to come. She obviously noticed, and is hoping you will take her up on the offer, or she would not have asked. I would have been ready on the spot...lol.

  20. #45
    Just another 'Gurl'
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    No, no,

    I say you made a fantastic choice. We all know how wonderful life is living alone, and feeling ashamed, in each of our proverbial closets. I look back on those missed, wonderful and exciting opportunities in my life and give myself 'an atta boy, well done' each and every day.

    Quick as you can now, call her again. Tell her that you where drunk when you said you wanted a makeover. Stay afraid, in the closet. Please, don't leave me. Oh bother.
    Last edited by Kitty Sue; 03-22-2011 at 02:53 PM.
    Just another man in a dress

  21. #46
    Senior Member Stephanie Miller's Avatar
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    Originally Posted by darla_g
    shouldn't that be big girl panties?"


    "You say tomato, I say tomahto"

    http://www.thelingeriezone.com/shorts.html

    ( I know what you meant though. I just didn't want to say it that way. )

  22. #47
    What is normal anyway? Rianna Humble's Avatar
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    Quote Originally Posted by Matt2Marissa View Post
    So, I've been dating this girl for almost a month now, who I've been friends with since high school. She asked me if she could give me a complete feminine makeover (I have a sort of feminine body shape and a not so masculine face, which she told me made her always want to ask). I wanted to say yes, but I'm rather paranoid by nature, so I said "no"
    Then you wonder why SO's who discover that their partner cross-dresses get upset about the deception?

    You like each other, she is wiling to accept your feminine side and offers to let you take it to another level, so what do you do? You LIE to her. Why are you dating someone you are unwilling to trust after all this time?
    Last edited by Rianna Humble; 03-23-2011 at 10:52 AM. Reason: sp
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  23. #48
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    Tell her you had a thought that it would be HILLARIOUS to have her take PHOTOS of you as a girl, out at the mall, etc
    and for them to be good enough that you could fool people into believing they are your cousin or sister ... so lets do it!

  24. #49
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    Or just tell her you're up for it again without giving a reason. Might not work for everyone, but some of us just say, we want to do it, just because. You can divulge more after you're more comfortable.

  25. #50
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    Ohhh Marissa...please take her up on her offer and let us know how it goes! I would love to have a female allow me to dress in front of her and then have her do my makeup...it would be a dream come true. It sure sounds like it doesn't bother her at all! Go for it!

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