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What's your favorite crossdressing experience you've had?


MadelineWilco

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i think for myself, my favoutite times, are when guys start chatting me up, not knowing my secret, such a confidence booster

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  • 2 weeks later...
On 3/19/2021 at 8:36 AM, Kiera said:

 

      I love flouncy, more 60's style "luv child" dresses has anyone here shopped "airydress . com" I cannot believe their flash sale pricing I placed an order just to see if "for real" or not . . they're based out of Hong Kong with warehouses in the US.

I wish I had the figure for a 60s outfit, black and white two tone dress and knee length boots, proper bob hairstyle, dancing away to Jacques Dutronc or Christie Laume.....

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  • 7 months later...

I drove my car out in my black dress, black wigs, black gloves, black pantyhose and black high heels, in our country, crossdressing is definitely a no-one-accepted attempt. To avoid been seen by others while I'm enjoying the clicking heels on the road, i chose midnight as my personal fun time. 

It is not fun anymore when I haven't even get out of my car, just stopped by roadside, intended to walk into the park, a police car drove by and speed towards me when they saw me. They requested me to get out of car, wanna check my car and see if I possess drugs. 

Awkward moment came when I stepped out of my car in my high heels, they were totally shocked and asked me why I did so. I lied to them that I am a youtuber (which I am literally one now), dressing like this for more view, more income for my family. They asked me if my parent know, the hell I would let them know! 

They checked my car, saw plenty of heels behind (I am heel addict, love to wear variety type of high heels), but nothing else after a 5 min checking (one checking, one waiting awkwardly with me, looking at my heels and ask if it hurts). 

After all done, I asked them if i can continue walking around here since I have no illegal intention and belongings, they just remind me to be careful...

Extreme awkward changes to extreme bravery, as they gone, I went all out, no longer care if any other car passing by, just enjoy my moment there, under light, walking along the street, with my favorite heels clicking in the midnight. That was my most fascinating part when I enjoy myself without thinking what others think. Luckily no cars drove by, it was real safe at that moment. Or else I could be regretting been taken photos (my car was there under street lights with clear plat numbers!) 

IMG20200315040100.jpg

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Wow.  Glad things went okay for you.

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  • 3 months later...
On 6/25/2020 at 12:40 PM, VickySGV said:

For me it was nearly 20 years ago when I treated myself to a full makeover at a CD boutique.  

Oh how I have longed for a place such as a CD boutique to get some assistance.. I'd love to spend a few hours getting made over, then ideally hang out for a while with some of the other girls who've also just had a make over, talking, a drink or 2 and maybe a bit of music and dancing.. sounds like heaven! 

Unfortunately there's nowhere like that where live :( 

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On 6/25/2020 at 8:15 AM, MadelineWilco said:

Hi all,

When I dress up, I "become" a girl. I go by she/her pronouns, and my name is Madeline. What's your favorite crossdressing experience you've had? Mine was my second time. The first time dressing up was just "meh," but the second time was amazing and just felt sooo good. I put on my brunette wig and full face of makeup, I put on my lacy bra, then, as I slipped on my lacy cheeky panties, my voice all the sudden became flowing, breathy, and extremely feminine, and I cutely and very girly said "Oh, yes, This feels so amazing, ohhh!!" I started finishing up my dress up with my mini dress, fingernail and toenail polish, high heeled sandals, and pantyhose, I looked at myself in the mirror and was amazed at how sexy I looked. I was gorgeous! I said very girly "what a very sexy girl you are, Madeline," and I giggled in an extremely girly way! Last time was not so great, but this time was so pleasing and I was so sexy! I enjoy it very much when I do it, but nothing will ever beat my second time as Madeline, EVER. Share some of your awesome crossdressing stories!

Thanks,

Madeline

Great Madeline you are a role model for people like us. I too wear lingeries but they belong to my wife and i crossdress only when at home or i go out of station for vacation.

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