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When I was 15 my mom was taking me to school. My older brother drove and we just got done dropping my sister off so it was just us in the car. My mom asked if I was going to do Halloween this year? I did the typical 15yr old answer no im to old for it. She said you never to old to dress up and have fun and get free candy, well think about it. The next day she asked hey you remember my Elvira costume? Do I remember it? Slinky figure hugging black dress, Stiletto heels, and hose hell yea I remember it. I said yea I think so she said you can wear that for Halloween. I said I dunno about being a woman she said oh thats nonsense its Halloween no one would care. When I was getting out of the car I said ok I will do it mom said good I will lay it on your bed. When I got home I tried not to run to my room on my bed was the dress, High heels, Pantyhose, Fishnets, Panties, and a Bra. My mom said all you need is a wig and some witch make up well try it on lets see how it looks put socks in your bra and the fishnets goes on over the pantyhose. I was shaking and nervous putting everything on. I was wobbly in my heels when I showed my mom she said how lovely I looked and no one will know you are a boy. When I walk away to change she noticed how wobly I was in heels and she recommended me to practice walking in heels everyday after school. One day I was in a local Big Lots looking threw Halloween stuff when I found a pair of black gloves and a witch hat with attaches wig and mask. Now with the gloves and witch hat and mask no one will know I was a boy.
Halloween day I shaved my legs and got ready we had a family get together at a church then we all went trick n treating. No one guessed I was a boy I was called miss and ma’am all night. I wore that out every year until it fell apart I took my younger brother out while I was wearing the outfit. What I had buried in me started coming out that first Halloween.
Thanks Brandie,
What a lovely tale, what a lovely mum.
If ever they create “Be me for a day” technology, can I book out that day to borrow from you for myself?
Marti xxx
Brandie, that is a wonderful story! I know when I was a kid, my parents would have freaked out at the mere idea of me wearing a costume of a different gender. This is my first Halloween as a CD as well, I haven’t dressed up in decades.
The last time I wore a costume for Halloween was back in my wild college days. That story best remains untold, but there may still be police records out there somewhere, journaling part of the night’s events. Don’t worry, I was on the right side of the law. 😉
Anyway, I am planning on meeting another CDH girl at a local bar on Halloween. We still need to finalize those plans. But, I am now drastically overthinking what I want to wear. I have something kind of sexy that I wanted to wear, but then my mind starts telling me that it’s wrong to sexualize an image of females. I also thought about a wholesome female role model, Wonder Woman (Gal Gadot, first movie WW costume). But, I have absolutely nothing for a costume like that, I’d be starting from nothing. And I’m also concerned that I’ll freeze my butt off out on Halloween night. So, I have no idea what I want to wear…
Birel
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Halloween is the crossdressers holiday! Yea for Halloween!
Great story and your mom must have known of your feelings. What a great mom.
Halloween was the first time I ventured out in public fully dressed to the nines. I was walking on air… such a rush of feelings. Had a great time with another CD friend and my public outing virginity was broken.
Hi!!!
Do you recall what you wore ; was it a character or were you man in woman’s clothes and that was the point of the custume?
Best Jaime-
Hi Jaime.
My first time out I felt like the hottest woman around and from all the attention I was getting maybe I was.. lol. A CD friend and I stayed at a hotel in the city and walked a couple blocks to a CD friendly bar. We got more attention from people on the sidewalks and in vehicles than we did at the bar.. lol. Seemed like everyone within sight was staring at us or so it felt that way but I was thrilled!
The outfit I wore I was going for a hot secretary look… maybe it was more hooker than secretary… lol… but it was so exciting.
I wore a shoulder length blonde wig with black roots, full makeup with big false lashes, gold earrings, a tight pink long sleeve turtle neck top, a long gold necklace, a 40 D cup bra with silicone forms, a wide black patent belt, a black short pencil skirt, a black garter belt, white satin panties, black nylon stockings, 4 inch black stilleto heels, three gold bangle bracelets, two rings, and a small cute black purse with a thin shoulder strap… Michelle was OUT in all her glory! Will never forget that night!
My kids knew I always got dressed for Halloween to take them out to get candy. One moment I will always remember, my son was returning from a track meet, I drove to pick him up at the school, the coach told him your Mom is here, he said no that is my Dad. As a very macho person as he got older he never liked to see dressed and I respected that.
When I was a young boy somewhere around 10 my mother had the idea that my Halloween costume should be a hula dancer. My father had ben stationed in Hawaii so they had the necessary items. My first initial reaction was no way. My mother said I would be cute in the outfit. I eventually gave in and wore the complete outfit grass skirt and all. When I saw myself in the mirror I could not believe how much I liked what I saw. To this day I still have the picture of me in that costume. In subsequent years I chose feminine costumes and no one ever said anything about my choices.
Currently I wear a French Maid costume on Halloween and have done so for the past number of years. I always get a reaction which I am pleased to say have been positive from both males and females.
Great story!
When I was a boy, I always looked longingly at the girl costumes. I always wanted to be the naughty nurse, sexy witch, hot teacher, etc. 🙁
My very first purchase of girl clothing (that I didn’t borrow from my sister) was a Sexy Cheerleader costume for Halloween.
OMG I was so nervous walking in to buy it, I will never forget that. Like I thought there was a huge spotlight on me and that I had been outed haha. So silly and stupid in retrospect.
Anyway, got the costume, bought a wig. Ended up hooking up with a guy for Halloween while I was dressed. Trick or treat for me! 🙂
I missed out on trick or treating as a girl when a child but did attend a public party when I was 19. My friend and I went for the Elvira look with dark makeup and long straight wigs. I must have passed pretty well since I was getting hit on by straight guys and was asked for my phone number by one. Little did I know that it would kick start my career as a girl a year later..
Love your item, saying who loves to wear red heels. Red is my favorite color. My dream would to go out en fem wearing only red things. Wonder would I would I be called “a Scarlet woman”?😂😂❤️❤️
Thank you Brandie for sharing your story. How special is it that you had the support / encouragement of mom. I love her “mom to “daughter” advice, ” practice walking in your heels every day after school.”
I suspect for many of us Halloween is an important date in our femme journey.
Ah yes, Halloween, I learned something that day. Here is my lesson from 61 years ago.
https://www.crossdresserheaven.com/i-learned-something-that-halloween/
Kindly,
Charlene
Dear Charlene
Thanks for your memories! Halloween was not necessarily a CD moment that I recall but like you I am getting a bit long in the tooth and don’t share your memory. But I know that one of my sisters has all the photos of our family and many of the extended af least from the early 50s until we all graduated from college .
I might give her a call and see if she recalls or has photos or dates. I ll
Get back to this forum after memory jogs loose. She is 6 years older than me and was a self appointed general with in particular. She painstakingly taught me how to starch and iron a blouse or shirt. I digress but you girls who use a bit more hair color than a few years ago, know what it is like to iron ruffled trim each one at a time.
Anyways I ramble and I am sorry . It’s just one memory triggers something random I go down that rabbit hole,my bad girls with my Halloween story courtesy of my oldest sister. Love Jaime
now that I’m to old to run around in black tights and a skirt…I sit in the house on Halloween and dress like the bride of Frankenstein, or morticia from Addams family… all black and white skirt heels and tights…..my hair is long so I can tease any way I want…..but being able to walk back and forth in the apt without worries my heels are loud…is great…..and the reaction from moms and dads when I open the door its great…some want to take pics with me and their kids…..I always wonder where those pics end up…..any how wanna dress in pantyhose without a grey cloud….Halloween is the time…..it was made for pantyhose and skirts
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Great story, I had a mom that found out I was wearing her panties and she bought me my own and a bra that fit me. A couple of halloweens at work I dressed up as a woman and as Sleeping Beauty. Both times I had such fun, even had a few people say I walked in heels like a pro. One asked where I found all the clothing, I so wanted to say my closet but said Goodwill. Had they only known that I so love to wear girly things and go out.
Sandy
Hi brandie as for halloween havent been out since a little girl i was .. I have made mention of as a young kid young teen as mom helped with some clothes as i was the baby sister sitter growing up and mom was a big part in Stephanies life .. Mom knew dad and older brother were to be gone on a buisness trip over halloween so she called my aunt and got everything together for the transformation into Stephanie dressed me to the nines with all girly clothes heels wig and full makeup then we took sis and went trick or treating was a perfect time in my life so much fun..
Stephanie Bass
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