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Thread: Wife gave me a "challenge"

  1. #1
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    Wife gave me a "challenge"

    So last night, I got all dressed up, hoping to go to the movies with my wife. She wasn't feeling well, and didn't seem like she was up for it, so rather than getting mad, I just decided to run to the post office. It's not the movies, but it was at least out of the house. On my way out of the door, I jokingly asked if she needed anything while I was out, she said that we needed milk for breakfast. I said is that a challenge? She just smiled. I was highly overdressed for the grocery store...knee high boots, black leather mini skirt, and sequined top, but decided to go see if I could muster up the courage. My first attempt, I decided to go to the post office first, only to realize that in the excitement of my challenge, I had left the mail on the counter. Since I was out, I figured I would see how busy the store was. Way too busy for me to attempt, so I decided to return home and wait a few hours. So 9:30 comes around, and I decided to go for it. Went to the post office, and remembered how hard it was to walk in the boots I was wearing, but decided to proceed to the grocery store. When I got to the grocery store, it was fairly empty, so I decided to go for it. As I was walking in to the store, I was thinking "what are you doing?", but kept going. I know it has to do with marketing, but why do they have to put the milk at the far corner of the store? By the time I got to the milk, my legs were burning from walking in my boots, but it was too late to turn around now. When I finally got to the checkout area, I was relieved to see that there was a self checkout lane open, only to panic when i discovered that it wouldn't let me ring up my item without the store loyalty card. So I proceeded to the next open lane, only to find that the clerk was having trouble ringing up the lady's cucumbers. It seemed like forever standing there in front of the customer, the cashier and the cashier's manager, but it was probably only a minute. But nobody was rude, and I didn't even hear a snicker. So finally, I got home and as I was putting the milk in the fridge, my wife says "So you really went into the grocery store?" And I said, "Challenge Accomplished!"
    This morning, out of the clear blue, she tells me "I still can't believe you went out!"

  2. #2
    Aspiring Artist Kelly DeWinter's Avatar
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    If there is ever a bet a spouse will loose, it's to challenge a crossdresser to go anywhere dressed, it's like throwing away money. LOL
    Kelly DeWinter
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  3. #3
    Lady in Being (7/20/17) AmyGaleRT's Avatar
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    That's the first place I went when I actually got out of the car, Flowergirl...to a grocery store. I've been to a number of them since, including one time when I got there a little late and one of the clerks looked up and said, "Ma'am, we're closed."

    - Amy
    Amy Gale Ruth Bowersox (nee Tapie) - "Be who you are, and be it in style!"
    Member, Board of Trustees, Gender Identity Center of Colorado
    aka Amelia Storm - Ms. Majestic Hearts of All Colorado 2018-2019, Miss Majestic Hearts of All Colorado 2015-2016

  4. #4
    Senior Member mikiSJ's Avatar
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    About 20 years ago I was standing in line at the local supermarket when a maid (the kind you see in kinky movies) walks up behind me. I think it was a similar 'challenge' as I could see the blushing under the very overly applied makeup. I simply said hello, slight smile and no smirk.

    So, flowergirl, I am glad you took up the challenge.
    When writing the next chapter in your life, start with a pencil and eraser - my first page as Miki is full of eraser marks.

  5. #5
    Gold Member Alice Torn's Avatar
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    Wow. That went well, but,i would have bee anzious, too. Good thing i was not dressed up, at Walmart tonight! The computer system there suddenly had glitches, and the lights went out for a while. I was stranded at the cashier for at least 15 mintutes, then had to cancel my transaction, wait in line again, and try again, which took about 7 minutes. All the time, holding up a long line. Tempers were getting raw. If i had been prettied up, it would have been a real scene!

  6. #6
    There's that smile! CarlaWestin's Avatar
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    Oh, I've been thinking about a personal grocery shopping in the sexy maid's outfit challenge. Again!
    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!

  7. #7
    Gold Member Jaylyn's Avatar
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    I would have been a nervous wreck... I would have probably just went out and milked a wild cow at the barn rather than go out.... Lol I am proud of you though for staying and getting the milk and finishing the task. Good job.

  8. #8
    The non-GG next door.... Candice Mae's Avatar
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    I will give you props for having the courage, but I think you were over dressed for the movies to being with. But that's just me.
    Last edited by DAVIDA; 12-06-2013 at 06:31 AM. Reason: Correcting grammar, spelling, or puntuation is not allowed.

  9. #9
    Member JenniferYager's Avatar
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    Last edited by DAVIDA; 12-06-2013 at 06:34 AM. Reason: Removed IMG tags. Pictures do not comply to forum size limits.

  10. #10
    Aspiring Artist Kelly DeWinter's Avatar
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    I did the sexy maid to a Highs for a Halloween Party. Jeannie and I were going to a local TG/CD party when we realized we did not bring a snack, she was dressed as the Queen of hearts and did not want to go inside, so shee looked at me and said "Fifi, be a good servant and fetch the Queen some chips and dip" I laughed so hard. It was also the first time I ever drove in Stilletos (Not reccomended)
    Kelly DeWinter
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  11. #11
    Lady in Being (7/20/17) AmyGaleRT's Avatar
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    Actually, I've done that for my fiancee in both modes. As Amy, it's easier on me; in fact, it can be an effective boost to one's image.

    - Amy
    Last edited by Shelly Preston; 01-02-2014 at 02:23 PM. Reason: some subjects are not allowed
    Amy Gale Ruth Bowersox (nee Tapie) - "Be who you are, and be it in style!"
    Member, Board of Trustees, Gender Identity Center of Colorado
    aka Amelia Storm - Ms. Majestic Hearts of All Colorado 2018-2019, Miss Majestic Hearts of All Colorado 2015-2016

  12. #12
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    Awesome outing sounds like!!

  13. #13
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    sounds scary but fun x

  14. #14
    Platinum Member Beverley Sims's Avatar
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    Yes definitely overdressed, but a good experience.
    Now to do it again, it will be easier, I assure you.

    Candice,
    Every sentence is a paragraph for me.

    Some spacing does help in the readability stakes Flowergirl.
    Work on your elegance,
    and beauty will follow.

  15. #15
    Gold Member Maria in heels's Avatar
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    You did great Flowergirl!

  16. #16
    Silver Member linda allen's Avatar
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    If you were overdressed for the grocery store, why didn't you just change into something more appropriate? That's what most women would have done.

    I think you were overdressed for the movie theater as well. Do people really get dressed up to go to a dark movie theater?
    [SIGPIC]http://www.crossdressers.com/forums/image.php?type=sigpic&userid=82706&dateline=137762 0356[/SIGPIC]Linda

  17. #17
    Aspiring Member vallerie lacy's Avatar
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    I applaud you for going to the store overdressed. The sign of a real CD.
    After searching my lingerie drawers, I have come to the conclusion that they lied. Ruffles don't have ridges. At least mine don't.

  18. #18
    There's that smile! CarlaWestin's Avatar
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    Hmm? Is there a challenge thread lurking about? So far I've been writing all of these down. I just need someone to call me Fifi! Nothing like a little adventure to get the heart rate elevated. And there's nothing wrong with that!

    Has anyone ever gone bra shopping while beautiful?
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    Last edited by CarlaWestin; 12-06-2013 at 10:58 AM.
    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!

  19. #19
    Senior Member 5150 Girl's Avatar
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    Now that you've ventured out for the first time, it will get easier and easier every time you do it!

  20. #20
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    Good for you Flowergirl.
    Dana M

  21. #21
    Carole carhill2mn's Avatar
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    One of the great things about going to a grocery store is that people stop there before going out somewhere or after having been out to some place. Thus, they are dressed in all sorts of ways. My exeperience has been that almost no one pays any attention to you as they all have things that they are looking for. Believe me when I say that it will get easier each time.
    Hugs, Carole

  22. #22
    @--}----- Sissy_Michelle's Avatar
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    Awesome Flowwrgirl! Not bragging but I probably would have gone when it was busier so I wouldn't get noticed as much. Thinking that if there are less folks there that would give the people there more time to spend looking at me. Rather than the rush of get my stuff and get out.

    I will have to try it...

  23. #23
    Silver Member linda allen's Avatar
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    So exactly what is a "real CD"?
    [SIGPIC]http://www.crossdressers.com/forums/image.php?type=sigpic&userid=82706&dateline=137762 0356[/SIGPIC]Linda

  24. #24
    Chickie Chickhe's Avatar
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    The grocery store is one of those places that has very good lighting and very slippery floors. For that reason, it can be a pretty scary place if you are not comfortable. It is a great accomplishment to do that....it is a real test of whether you can actually go beyond fantasy and experience what real life would be like as a woman.
    Chickie

  25. #25
    Aspiring Artist Kelly DeWinter's Avatar
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    Quote Originally Posted by linda allen View Post
    So exactly what is a "real CD"?
    Real CD's
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    Kelly DeWinter
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