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Thread: What was your Jackpot Crossdressing Day where you Modeled the most fun outfits

  1. #1
    Aspiring Member Robbiegirl's Avatar
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    What was your Jackpot Crossdressing Day where you Modeled the most fun outfits

    Only a CD will understand how much fun it is for us to try on the variety of dresses and gowns women get to wear !! So Its fun to hear of everyones best and funnest moments !

    Were you ever lucky enough to have a gal pal or girlfriend that just opened up her closet to you and had you model many of her fun dresses for her ?

    Or

    Were you ever lucky enought to be in a situation where you were house sitting and found a whole closet full of fun dresses that you were able to fit in ?

    I think most of us want to experience at some point being in a situation where we could experience wearing a prom dress and or Bridesmaids dress

  2. #2
    Female Illusionist! docrobbysherry's Avatar
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    Too many such days to pick out just one--------
    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!

  3. #3
    Heisthebride Heisthebride's Avatar
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    My most fun day, single day. Could be any of my professional photoshoots, I've had three. Professional hair and makeup. Multiple clothing options, from bikini by the pool, to formal wear, to sexy lingerie boudior style photographs. The whole works. It took about 5 hours for everything from start to finish. I am waiting on the final touchups and album from my last one in October.

    If I get to count more than a single day it would be my girl only vacation. 5 days in Las Vegas, with no boy clothes whatsoever. From the moment I left my house en femme, to the moment I arrived back home, it was girl mode only. Public transportation, airport security, on the plane, going shopping, to restaurants, to casinos, to bars, everywhere. I made sure I didn't pack any boy clothes so I had no other option.
    Rebecca Bas

  4. #4
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    Thrift

    Went to hell with myself during a thrift store session ABSURD number of outfits, but a very happy night.

  5. #5
    Aspiring Member Brenda Freeman's Avatar
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    My favorite was at a Hotel where I was attending a Tgirl convention. I had my make up professionally done one morning. I loved it so much I spent the rest of the morning in my room trying on different dresses and various lingerie for a fun photo shoot. I could not believe how I looked, did not want the day to end.
    Attached Images Attached Images

  6. #6
    VSJ Victoria StJohn's Avatar
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    Beautiful photos Brenda. I see why you were so excited for your photo shoot. Did you not go out in the world to show the beautiful looking lady?

  7. #7
    Aspiring Member Brenda Freeman's Avatar
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    I did Victoria, this was at Esprit a tgirl event, went to lunch with friends, shopping, dinner and dancing the evening away. It was like Cinderella at Midnight the make up came off.

  8. #8
    Senior Member TheHiddenMe's Avatar
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    Hard to pick one.

    1. My first real days out. Arranged a Sephora makeover, then had a dressing room ready at Nordstrom filled with dresses and sales angel Falon eager to make me happy. Spent time the next two days trying on more at Nordstrom and bought two dresses (thread in photo section).

    2. Multiple shopping trips with my GG friend Michelle.

    3. A bathing suit photoshoot wearing many of Michelle's suits at her private pool.

    4. Trying on Hand-Dee-Downs from Michelle; she gives me the clothes she's tired of, so I get to try them on.
    I'm Sun-Dee at Kandi's Land; read about my outings here:

    https://www.kandis-land.com/author/dee/

    Author Sagelllini (with three lower case "Ls") at Literotica.com

  9. #9
    Gold Member alwayshave's Avatar
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    The only time I every made several wardrobe charges in a day is when I had a makeover at True Colors. I did enjoy it.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  10. #10
    I love being a girl
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    I remember spending the best part of two weeks enfemme in my mothers clothes when I was about 17yo. Mum and dad went away for a holiday and left me in charge of the house and animals. I only dressed inside, never ventured outside, and tried on nearly everything mum owned. It was a gloriously happy couple of weeks.
    I love being a girl

  11. #11
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    Went on a big lingerie shopping spree one day years ago and spent what seemed like hours modeling all of it when I got home. Loved every second of it!

  12. #12
    Miss Conception Karren Hutton's Avatar
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    One of my favorite days was when I visited a local CD friend and we tried on her beaded wedding dress and some of her other clothes.

    wedding dress.jpg
    Come over to the dark side - We have cookies!

  13. #13
    Connie Connie D50's Avatar
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    My daughter went shopping with me, had a wonderful time. Then after we got home she asked me if I wanted to try on the black dress we had bought again. That led to me modeling about 6 more dresses I had that she had never seen. I'm lucky both my daughters are accepting.

  14. #14
    🌺T🌸R🌼A🌺N🌸S🌼V🌺E🌸S🌼T 🌺I🌸T🌼E🌺 Patience's Avatar
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    Quote Originally Posted by Robbiegirl
    Were you ever lucky enought to be in a situation where you were house sitting and found a whole closet full of fun dresses that you were able to fit in?
    Being 6'2", I think that occurrence would be highly unlikely. Anyway, going through people's things and putting on their clothes in their absence seems like violating someone's trust. I would not want someone else doing that to me.

    Quote Originally Posted by Robbiegirl
    I think most of us want to experience at some point being in a situation where we could experience wearing a prom dress and or Bridesmaids dress
    No prom dresses for me, but I'd love to wear any wedding regalia.

    My best photoshoots happen at the end of the days when I had a makeover and have the house entirely to myself. I'll pose and take pictures for hours - in my own clothes.
    ...throw off those chains of Reason and your prison disappears...

  15. #15
    Silver Member NancyTO's Avatar
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    I went to Fantasia Fair in Provincetown MA back in the late 80's. I got picked to be in the Fashion show. It was a surprise, and you had to wear your own outfits, but as a good CD'er, I had brought more than enough outfits to wear for the event.

    A friend supplied just a couple of photo of my "business girl" look.

    You can spot Transgendered Pioneer Virginia Prince in the audience. York University (Toronto) Professor, Miqqi Gilbert is MC'ing the fashion show.
    Attached Images Attached Images
    If your not living on the edge, you're taking up too much room.

  16. #16
    Once upon a time... Veronica Lacey's Avatar
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    Have had a couple opportunities when the Missus is out of town for a few days (she knows of my dressing and that I have an extensive wardrobe.) I have done some photo shoots with me trying on a range of blouses, skirts, shoes, dresses and lingerie. Truly relaxing to enjoy slowing it down and savouring much of my wardrobe, the colours, styles, fabrics and how they fit.
    Each time a Jackpot CD Day indeed.

  17. #17
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    Never hit the jackpot in CD or the lottery .

  18. #18
    Silver Member Maria 60's Avatar
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    I enjoy when my wife does her spring and fall wardrobe cleaning and she wants me to model for her so she could select what she wants to keep. My most memorable and not memorable moment was when my sister in law asked me to model some dresses but I got an anxiety attack and I thought I was having a heart attack. I had the attack on the very first item I tried on, I believe if I would have controlled myself that would have probably have been the most amazing and memorable day.

  19. #19
    Member 1Ladyjade's Avatar
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    Yesterday. I went full dress yesterday. I did full makeup with my stockings garter miniskirt and bralette. I still don't have a proper blouse/top to wear so I wore a lace robe over the top. Wish I could post a picture. My friend that has given me a place to be Jade thought I did a great job on my make-up.

  20. #20
    Silver Member CynthiaD's Avatar
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    Yesterday. I wore a mid-thigh black alligator-skin (fake) dress. Mock turtleneck with long sleeves. The dress was tight and I wore a corset underneath, which gave me a perfect hour-glass figure. Black pantyhose and black heels at the bottom a long blond wig with dark roots on the top. Medium sized breast forms, red lipstick and jewelry went on last. I looked fabulous, all day. No makeup or nail polish though. Maybe next time.
    What do I do on days when I don't crossdress? I have no idea.

  21. #21
    Member susann_gardener's Avatar
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    I have a TG friend who used to live nearby. Spent many afternoons there dressing. Best was when her neighbor did my makeup and we went out to a mall. She had her ears pierced while I browsed the stores.
    Susann_Gardener

  22. #22
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    I am not lucky enough to have closet full of fun dresses to try on but I went to Victoria secret about 8 years back for bra fitting after gathering courage and 3-4 previous failed experiences. This one sales person was very nice to me and eventually I said I want to be fitted, and her face just glowed. She took me inside in last stall, asked me take off shirt, measured and brought 2-3 bras to initially try. From that point onwards, she just kept bringing all different sizes and kinds of bras and lingerie to try for next 1 and 1/2 hour . I was enjoying but at the same time she enjoying too and never pushed me to buy anything (did purchased 3). I must have tried atleast 30 different bras/lingerie that day and felt that I was in heaven .

    -Remee

  23. #23
    Silver Member Sometimes Steffi's Avatar
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    Quote Originally Posted by alwayshave View Post
    The only time I ever made several wardrobe charges in a day is when I had a makeover at True Colors. I did enjoy it.
    Been there, done that. Makeover and 4 outfits, including a wedding dress and ball gown. I got well over a hundred pics. One of them is my profile pic (not the Bugs Bunny avatar.

    Quote Originally Posted by Brenda Freeman View Post
    My favorite was at a Hotel where I was attending a Tgirl convention. I had my makeup professionally done one morning. I loved it so much I spent the rest of the morning in my room trying on different dresses and various lingerie for a fun photo shoot. I could not believe how I looked, did not want the day to end.
    At Keystone, about 10 times. At least 2 outfits worn out per day, one during the day, one at night. At least one makeover over the 4-day event. Sometimes 2 or 3 makeovers. Usually 1 photo session a day, plus I did a boudoir photo session once.

    Quote Originally Posted by Heisthebride View Post
    My most fun day, single day. Could be any of my professional photoshoots, I've had three. Professional hair and makeup. Multiple clothing options, from bikini by the pool, to formal wear, to sexy lingerie boudoir style photographs. The whole works. It took about 5 hours for everything from start to finish. I am waiting on the final touch ups and album from my last one in October.

    If I get to count more than a single day it would be my girl only vacation. 5 days in Las Vegas, with no boy clothes whatsoever. From the moment I left my house en femme, to the moment I arrived back home, it was girl mode only. Public transportation, airport security, on the plane, going shopping, to restaurants, to casinos, to bars, everywhere. I made sure I didn't pack any boy clothes so I had no other option.
    Keystone, 5 days, 4 nights, 10 times annually. A couple of times with no boy clothes. when I could meet a CD friend and change at her place. I usually I got 1 photo session a day at Keystone, plus I did a boudoir photo session once in my room once.
    Hi, I'm Steffi and I'm a crossdresser... And I accept and celebrate both sides of me. Or, maybe I'm gender fluid.

  24. #24
    AKA Lexi sometimes_miss's Avatar
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    It would have to go all the way back, to when I was a teen; parents and older sister all worked full time, and so I was left at home alone all day long, with full access to my sister's wardrobe. I tried on so many of her outfits, to find what fit me the best, and what looked the best 'on'. As she would stop wearing things when she felt they were out of style or no longer what she wanted to be seen in, and they were sent 'to the attic' for storage, they became mine to wear whenever I wanted to. My teen years were loaded with many days, wearing her outfits all day long, with a couple of close calls when someone came home early while I was completely dressed en femme.
    Some causes of crossdressing you've probably never even considered: My TG biography at:http://www.crossdressers.com/forums/...=1#post1490560
    There's an addendum at post # 82 on that thread, too. It's about a ten minute read.
    Why don't we understand our desire to dress, behave and feel like a girl? Because from childhood, boys are told that the worst possible thing we can be, is a sissy. This feeling is so ingrained into our psyche, that we will suppress any thoughts that connect us to being or wanting to be feminine, even to the point of creating separate personalities to assign those female feelings into.

  25. #25
    Fun Member Natalie5004's Avatar
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    I do remember the day I wore my first gown. If I could create a wish list....what a day I would have.

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