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Thread: Dumb Amy outs herself on vacation

  1. #1
    Member AmyJordan's Avatar
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    Dumb Amy outs herself on vacation

    Hi Girls

    Hope that you are all well.

    So we have just celebrated our wedding anniversary and to mark the occasion spent it in glorious Florida.
    Rented a beautiful villa on a lovely quiet gated community and also my wife Rented for me my dream car a Shelby Mustang both of which were to play in Amys downfall.

    The rules for the stay were pretty much as at home, outings were agreed to be in male mode so we could make the most of our time but once through the door of the villa I was expected to be Amy at all times.

    Upon arrival late in the evening at the gatehouse and registering our stay we were issued our passes, now being friendly souls we had a long chat with the lovely lady on duty and every evening after that she would clearly recognise the car on approach and she would come out and ask about our day, yes I know you are probably smarter than me and can see what is going to happen.

    The time was going great, we were doing all the usual things you'd expect visiting NASA, crocodile tours, and a concert but we also spent a few full days at the villa by the pool and I got very comfortable walking around as Amy.

    So first 'out' was by the pool, my wife was taking pictures and after making me pose for some time she casually informed me that the guy in the next door pool had been standing staring over the entire time probably 25 minutes, after that he appeared every time we were out again

    'Out 2' was one evening I took the rubbish out, it was late and dark and as I dropped in the bags at the side of the house the other neighbours door opened and he came out with his rubbish, this was panic stations and I probably done the worst thing possible and instead of straightening up and casually walking back in I bent over as if I was looking in the bin hoping he would go past so when he turned the corner he was confronted by the sight of a short skirt and 2 nylon clad legs standing beside the bin and my head in the bin, seems funny now but after him saying hi I stood up gave him a wave and tottered back in my heels up the path and indoors.

    'Out 3' one evening my wife wanted something from the store and said let's just go for a drive it's dark so no need to change and promised me I wouldn't have to get out of the car, fair enough I thought what could go wrong, well it seems quite alot, firstly as you may know although the roads are huge and several lanes wide they are very busy and slow down quite alot, next I had not anticipated the attention a Shelby Mustang attracts at times and this was the case that evening, whilst crawling along in the space of about 10 minutes near a busy junction 5 vehicles and a motorcycle pulled up beside us and wanted to talk about the car and hear me rev the engine I was literally like a deer caught in headlights nowhere to hide but luckily no one appeared to clock us as anything but 2 girls out and about, my wife said it was the short skirt and pantyhosed legs that were attracting them as we hadn't seen any other women wearing pantyhose alI the time we had been there, I suggested we put the roof up and hide them but she wouldn't let me.

    I was super relieved as we headed back but just as we were approaching the complex it hit me, the gatehouse!! I had to get through the gatehouse!! I asked, I pleaded with my wife to take over so I could sit over the other side of the car in the shadow but she just laughed.
    We pulled up and I kept inching forward hoping whoever was on duty would just open the gates and I could just keep driving but No it was the lovely lady we had made friends with and out she came her usual " Hi Guys" trailed off into a "Hi Gu... Gurls well look at you, you don't get too many ladies dressed like that in this heat" after a few minutes of my wife and her laughing and joking another car pulled up and thankfully she had to let us in.

    So that was a quick rundown of Amys adventure I will post the outfit I was wearing on that last drive in the photos section and later some other pics from our time there if anybodys interested.

    Thanks for reading

    Amy x
    Last edited by DAVIDA; 03-21-2025 at 01:56 AM. Reason: The topic you mentioned is not allowed to be discussed on this forum.

  2. #2
    Member Keremy's Avatar
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    First of all your wife is awesome. Sounds like a great anniversary vacation.

  3. #3
    Platinum Member alwayshave's Avatar
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    Amy, sounds like a great holiday. You'll never see these people again, so really no issues.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  4. #4
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    Hi Amy,
    Sounds like you had great fun on your vacation, I'm sure you looked fabulous, did you get any tanlines? I think you're wife is easing Amy into the public, tbh I'm surprised she didn't insist on you staying as Amy for the whole vacation as you weren't going to meet anyone you know and will never see those people again.

  5. #5
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    Sounds like you two ladies had a wonderful time celebrating your anniversary. Amy I think your wife likes showing off her girl toy! Great story.

  6. #6
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    ARE WE INTERESTED??????????????????? You KNOW we are!!!!!
    POST 'em!!!

    We love you!

  7. #7
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    You have an Awesome wife, and sounds like you had a great vacation. I wonder how much longer you get to keep your male clothes.

  8. #8
    Silver Member Sandi Beech's Avatar
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    Nice Amy,

    I am looking forward to seeing your picture posts. I assume you were on the east coast if visiting NASA.

    Sandi

  9. #9
    Gold Member bridget thronton's Avatar
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    Happy anniversary - a wonderful post summarizing your adventures

  10. #10
    Gold Member Helen_Highwater's Avatar
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    Amy,

    I'll take issue, you didn't out yourself. You appeared in public to people who don't know you and who you'll never see again. Outing is being seen by those who know you, and people you'd rather not know your secret.

    I've just spent a week in a holiday rental. Came and went as I pleased enfemme. Perhaps you need to realise you can do the same and no-one cares.
    Who dares wears Get in, get out without being noticed

  11. #11
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    Thanks for sharing your adventure. I think our biggest fear of "outing" oneself is have it occur too close to home and seen by a nosy neighbor with loose lips that sink slips. I will be looking forward for any picture postings.

  12. #12
    Hot Geezer Girl docrobbysherry's Avatar
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    Sounds like you're easily rattled, Amy? I hope you'll get used to strangers seeing Amy. That's one of the great joys of dressing out. Seeing various folks different reactions to u dressed!

    I consider myself a closet dresser. Because no one I know except my immediate family knows I dress. I don't dress near where I live!

    Yet, 1000's of people have seen me and Sherry dressed! In other cities, states, and countries. Not one of those many folks has outed me to anyone who knows the drab me yet!
    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!

  13. #13
    Silver Member Natalie5004's Avatar
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    Amy, who cares what strangers think. If anyone gave me a second look, I would flash them. Stay cool, calm and collected.

  14. #14
    Member AmyJordan's Avatar
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    I stand corrected Helen and consider my backside severely slapped

    Amy x

  15. #15
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    ~~~~~ TOTAL EYE CANDY ~~~~~

    Hi Amy , Beautiful Ladies always get Noticed, >Orchid**OO**
    Having my ears triple pierced is AWESOME, ~~......

    I can explain it to you, But I can't comprehend it for you !

    If at first you don't succeed, Then Skydiving isn't for you.

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  16. #16
    Senior Member Lacey New's Avatar
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    Great story and you have a great wife!

  17. #17
    Aspiring Member CDMargret's Avatar
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    Well this sound like the best time ever. Wonderful trip.

  18. #18
    Member cd300's Avatar
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    Sounds like a lot of fun and excitement
    Glad you had a great trip
    You do you !
    Xoxoxo
    Hugs
    Jessica Rose

  19. #19
    Aspiring Member Marketa's Avatar
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    I can read your heartbeat from the post, Amy.

    Well, sheet happens, but the important part is to have fun, which it seems you had. And I think it's the 2 girls in Mustang what cought attention, not the car by itself.

    And as others said: your wife's amazing.

  20. #20
    Member osteph's Avatar
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    Thank you !!!

    Thank you for sharing your amazing relationship!
    Looking forward to seeing the photographs and, perhaps, hearing a little about your feelings during the experience.
    Last edited by osteph; 03-22-2025 at 05:36 AM. Reason: Correction
    Osteph

  21. #21
    Soccer Mom in Training MsEva's Avatar
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    so glad you have an awesome relationship. That is the key. Glad you had fun. Thanks for sharing.

  22. #22
    its important mykell's Avatar
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    hello amy....first let me offer congratulations and happy anniversary.

    also i want to offer you kudos for your new steps into the 'wild"....seems you found an admirer .
    it appears your wife has had you making baby steps into the outside world and you have experienced what those of us that wander face when entering the wilds, no matter how carefully you plan your outings sometimes you have to girl up and wing it....'life is like a box of chocolate....you never know what you might get" (forest gump)

    im excited for you and the mrs. i would love to meet you and your rascally wife and her sister....i just got back from the keystone conference Sunday and so many attend with theyre spouses and meeting folks and hearing and sharing stories with everyone and how different we all are was fascinating....maybe you could come to keystone for your anniversary next year

    also i dont think dumb is a good word for amy....perhaps a little naive
    Last edited by mykell; 03-25-2025 at 05:48 PM.
    ....Mykell
    i dressed like a girl and i liked it! crossdressing...theirs an app for that

  23. #23
    Aspiring Member Philipa Jane's Avatar
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    Oh my word Amy you gorgeous girl.
    Like Jamie Lyn said "ARE WE INTERESTED." You bet your life we are. So much so that I am going there next to view the pictures.


    Philippa Jane

  24. #24
    Member AmyJordan's Avatar
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    Hi Girls

    Thank you all for your amazing and encouraging comments.

    Mykell you are absolutely right these may seem like small steps too much braver members here, and I accept their argument that I was far from home and will never see these people again but to me it felt like a giant leap ( yes I know I have stolen that phrase ).
    My wife has been exceptionally patient but certainly enjoys it when I'm caught in awkward situations.

    Maybe next time

    Amy x

    ps Philipa I will post the pool pics soon thanks for the interest.

  25. #25
    Junior Member
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    Honestly. I would love that kind of self acceptance. To go out for a drive and wear pantyhose and a short skirt. Driving around town. Talking with people. So exciting.

    Couldn?t imagine this in my future. But I very much hope so.

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