For Halloween did a Female or your Mother ever offer to dress you as a Girl

[Robbiegirl]

Do you ever recall a female or your mother offering to dress you as a Girl for Halloween ?

Did you accept and if so do you remember what you wore ?

If you didn't do you remember any details of the outfit you sadly turned down.

My mother twice tried to talk me into girl costumes ! I was probably around 10 when she and my older sister excitedly wanted me to put on her old Brownie uniform and beret ! I of course was too scared and had tried on the dress before, so knew it would fit.

Then about 2 years later my girl cousin brought over her junior high cheer leading uniform for my sister. When it didn't fit her they all tried to get me to try it on complete with the panties that came with it and my sisters training bra ! What was I thinking ? I never got to try it on !

So funny how vivid my memories are of some crossdressing opportunties missed ! LOL

[Raychel]

Sadly no, No one ever tried to get me to dress as a girl for Halloween.
Not sure what I would have done if that had happened,
I probably would have been too embarrassed to try it at the time

There was one time when I was a kid, I was at a friends house.
And his mother and his sisters wanted to dress me up.
A missed opportunity for sure. The 2 sisters and the mother were all VERY good looking.
That could have been so much fun.

Then one time my wife was going to a Halloween party and she went as an old man, she dressed me up as an old woman
That was just awkward.
We ended up sitting with a group of loud obnoxious people.
Definitely not the crowd I would choose to hang around with.
I would not do that again.

[Crissy 107]

I had two girl cousins that wanted to dress me up as a girl. I was too embarrassed to do it. That was a missed opportunity that I still remember like it was yesterday.
It was not Halloween but looking back I still regret it.

[GracieRose]

I never had the opportunity. Although I often dreamed about it happening. If anyone would have suggested it, I would have probably vehemently refused. I was too afraid that it would be so obvious how happy I was.

[JocelynJames]

My X was going to dress me as a cheerleader one year , but I was ?too into it? and she thought I would become a CD. Little did she know that ship had already sailed and I was the captain !

[Brenda Freeman]

My mom wanted to dress me up as a girl when I was about 11 for Halloween. I wanted to so bad but said no. I was scared as I new how much I loved girls clothes. I always have regretted that. I would love to know what she had in mind. Funny looking back what that might have led too. Took me decades to finally dress up. My mom had wanted me to be a girl. It might have been interesting after that!

[Diane P]

I posted pictures in the Picture and Video forum of a half boy half girl halloween costume that my mother made for me when I was about 3 or 4. I don't remember it at all.

[Jenn A116]

No, not for me. As much as I might have enjoyed that, it just didn't happen.

[Karren H]

Oh yeah! My mother used to tell me all the time I was supposed to have been born a girl. And on a number of occasions she volunteered to make me a cute dress to go trick or treating in. Of coarse I turned her down on all occasions which were a couple years before I started experimenting with her clothes and lingerie. Looking back I so which I had said yes!

[Becky Bloodstone]

My wife and daughter wanted me to go out as day of the dead girls with them. I did my make up and everything and did not like the way I looked, more like a male long haired zombie, and quickly abandoned the idea.

[DianeT]

My now wife and her best girlfriend did it for Mardi Gras carnival when we were in high school (Halloween didn't exist in France back then). I was paralyzed by the fear of ridicule at first since the outfit was made of old clothes of my wife (a plaid skirt, opaque wool tights), my boy shoes, no wig or makeup. Went to school for an hour like this, and there the girls suddenly dressed a friend in a much worse attire (a shapeless dress brought by one of them for whatever reason) and made him up even worse, so I felt like I couldn't complain after all. Took me a good part of the day before being comfortable with the costume. An odd experience, and my only outing in my life, and it didn't really feel like crossdressing (I felt like a dude oddly dressed in vaguely female stuff), more like drag, which after all was in line with the spirit of carnival.

[EmilyShy]

This would be a real dream lol. Never happened not even close.

Only way this would happen is if my male self dares my female self to do it lol

[SaraLin]

Once. I must have been around 8 at the time.
We were poor and didn't have money for costumes, so my mom suggested I just put on one of my sister's dresses and go that way. I was secretly thrilled, but tried to not show it too much.

It was JUST her dress - and a (new) string mop head for hair. I still had my boy undies on, maybe even shorts - I don't remember that well.
What I DO remember is that one of the neighbor ladies' response that I was "the cat's pajamas." She was smiling ear to ear. I still carry that memory in my heart.

I'm pretty sure that I had already been secretly "borrowing" my sister's things for some time. I just hadn't been caught - yet.

[BLUE ORCHID]

Unfortunately That never happened to Me,

[CDMargret]

My peoples were just to leave it to beaver to offer dressing me up. And your missed chances to dress like that. OMG that could have been amazing. Just having that offered must have felt amazing and fun. Halloween is upon us so get out there and work it. Maybe a cheer leader outfit...

[Connie D50]

Yes my mom dressed me up twice once in my sisters baton outfit. The second time was for a female part in a skit for a cub scout play.

[oh to be rachel]

My wife and I have done several Halloweens with me in a dress. She was all in dressing me, doing my makeup and nails. On the first occasion, I went with her to her nail salon to get my nails and toes done. (Awesome experience!)

[Beano980]

Yes! This brings back a very good memory. I was mesmerized by female clothing already at that age (9) and a bit jealous I suppose of how cute the girl clothes were. I often thought about how it would feel to dress up like a pretty girl but there were really no outlets for me to explore. Halloween was a few weeks away, I had not really thought much about what I wanted to dress up as yet. On day my mother asked me what I wanted to be for Halloween, I blurted out that I wanted to dress up like a girl! I couldn't believe I had said that. She smiled, and said ok!. I wore a nice dress and white tights. No hair or make up, but hat was fine. I loved it. My guy friends gave me a tough time at first, but soon it was just another costume and we all ran thru the neighborhood collecting candy.

[Taylor186]

Forty-plus years ago, newly married in my twenties, we were invited to a neighborhood Halloween party. On the way home from a couple of unsuccessful mall costume-finding trips my new wife threw out the idea of me going dressed as a woman. She had seen a couple of guys do this at a costume party prior to our linking up, and thought it was good fun. I was stunned for a moment as I was deep, deep in the closet, and at that time owned no female clothing. I paused then said something like, "that's an idea . . . what are you thinking?" "Oh, just find something at Goodwill," she said.

She worked retail on Saturdays, so I went off solo to Goodwill to find the right "costume." And find it, I did. A skirted school majorette uniform with white stretch boots, that fit perfectly. I bought them and, on the way home, bought tan pantyhose to go with it. At home I tried on the pantyhose and decided I needed to shave my hairy legs to make the outfit work. (The pink fog was thick, even before I knew what pink fog was.) I then tried everything on and after a few adjustments, the mirror said it looked great.

I was still wearing the costume when she arrived home, and let's just say, she didn't share my enthusiasm. Interestingly, her number one concern was the likely negative reactions/assumptions regarding my shaved legs, given that everyone would notice as my legs are long and the skirt was short. Turns out her idea of a man-in-a-dress costume included a long flowered granny dress and tennis shoes with rolled up shorts underneath.

I didn't wear the majorette costume to the Halloween party, but I kept it. We parted a few years later.

her idea . . . . . . . . . . . . . . my costume (similar)

337786 . . . . . . . . 337785

[Monique65]

I have fond memories of the one and only time I was out in public en femme. I was in my early teens and told my mother I wanted to dress as a girl for Halloween. She put me in one of my sister’s dresses and tied a scarf around my head, then drove me to a Halloween festival in a neighboring town. It was exhilarating mingling with the crowd dressed as a girl, and I still cherish the memory.

[char GG]

Neighborhood play. When I was young, we always played en-mass (10 kids or more)! Play consisted of pretending like we were horses, circus, parade, anything with a crowd, etc. One day we played "wedding" and one of the little boys was the bride (I don't think it was his idea, he just fit the dress).

Now I wonder about that little guy: :daydreaming:

[Jillcder]

Yes, I was in elementary school my mother suggested dressing me like a girl for our school party I remember the dress and low heels she also gave me a quick very basic makeup lesson the one thing that stands out in my memory is my female teacher commented to me that I looked really nice as a girl.
When my wife and I were first married some friends suggested we all go out on Halloween with the husbands dressed as girls i was thrilled i envisioned wearing a cute dress and heels but instead I ended up wearing a cotton skirt and top not girly at all I was disappointed I actually talked her into letting me wear pantyhose that night.

[ShelbyDawn]

Sadly, no. I have three sisters and could have had so may options but, alas, it never came up.

And, OMG!!! You got offered a cheerleader uniform and passed on it??? Oh, the horror. LOL

[Raven Skyy]

I have to say I don't remember how many times my aunt who is a couple years older dressed me up. It was her desire to have a girl to play with. Living on a remote ranch I was that girl. Because of her I became aware of my love and desire for women's clothes and fashion . By the time I was ten I was totally in the closet hiding clothes , and dressing when I found myself alone. Now I probably have more girl clothes than male . I could probably donate 1/2 and still have more than most GG women. I know my closet dwarfed a few of my past girlfriends,

[Robbiegirl]

Sadly, no. I have three sisters and could have had so may options but, alas, it never came up.

And, OMG!!! You got offered a cheerleader uniform and passed on it??? Oh, the horror. LOL

Well it was the Bra and Panties that really scared me !!!

[MsEva]

Oh yeah! My mother used to tell me all the time I was supposed to have been born a girl. And on a number of occasions she volunteered to make me a cute dress to go trick or treating in. Of coarse I turned her down on all occasions which were a couple years before I started experimenting with her clothes and lingerie. Looking back I so which I had said yes!

Same with me. One year my Mom, God bless her soul, offered that to me. I too was supposed to be the girl, but I guess I let her down. I was the third of four boys! Anyhow I trying to find a good halloween costume and she offered to dress me as a girl. I kind of freaked out and had an outburst towards her. I wonder what she thought about that. I regret that, not the dressing but the way I responded. I guess it hit too close to home at age 7 or so even though I wasn't actually dressing then. I too wonder what it would be like. So that same year, a boy dressed as a girl for the school party. I was sort of amazed and could not keep my eyes off of him/her. She had a blonde wig, furry coat and go go boots.

[abby054]

Yes, at age nine, I hinted to my Mum that I would like to do Halloween dressed as a girl. She chose an outfit from some of the clothes she acquired from her much younger sister. It was a brown maxi skirt with some embroidery and a peasant style, off the shoulder white blouse with matching embroidery. She tied a matching brown scarf around my head and added clip on gold hoop earrings. I wore my own shoes because the long skirt eliminated the need for matching girl shoes. I was of slightly below average weight and height at that age. With some light makeup, I looked like a girl. I fit the part of a Bavarian dancer twirling in my long skirt. I wore the costume all day, to school, to march in a public Halloween parade, and to go trick or treating. The day was pleasantly warm. I needed no coat for the parade but by evening, it had turned chilly with a breeze. My Mum gave me a coat that her sister had handed down. I wore pants under the skirt for warmth as the girls my age did on cold days. I had a reputation at that age in a rather rough neighborhood for being energetic and feisty. I recall no one ever giving me any trouble about my costume, probably because wore it confidently like I owned it.