Did a female ever dress you for Halloween as a Girl/Woman

[Robbiegirl]

Not knowing you were really into wearing women's clothes ?

I turned down way too many opportunities when I was young and would love to hear about those that accepted the offer.

What specifically did you wear ? Did the female involved offer underwear also and if so was it plain or very girly ?

How much fun did you have and how much fun did she have ?

Later did she suspect you liked it too much ? LOL

The only thing i did close to this was having to play girl parts at my boarding school in the East. The teachers wives fawned over us putting us in cute Bras and slips and making us try on numerous dresses. It was amazing how much true joy these women seem to get in turning Teen age boys into girls and women. They espcially liked watching us struggle with putting on stockings and walking in heels.

[Alice B]

In the early 70's my first wife dressed me as a pregent bride and herself as the groom. Went to a party and had a blast, but had no idea that I would become a dresser over 30 years later. Once I accepted the fact that I loved to dress I told her and even went to visit her as Alice. She was totally accepting.

[docrobbysherry]

Sorry, Robbie. I can't fulfill your fantasy. My experience was much like Alice's.

My ex dressed me for a big, public Halloween party. Balloon boobs, beard, $3 wig, etc. She went as my short boyfriend and nearly punched out a drunk who popped one of my boobs! This was many years before I began dressing.

The evening made such an impression on me, I forgot all about it until 10 years after I BEGAN DRESSING!

[Nikki A.]

I had three girls dress me as the ex office manager for Halloween. My "wife" supplied most of the clothing and wig the rest we picked up at the thrift store. They did my make-up and helped me get ready. That day I became one of the girls. I later told one of the girls of my dressing up and we've been out together on a few occasions.

[sometimes_miss]

Nope. And back then, I wouldn't dare suggest it.

[Jaylyn]

Not unless you count my wife telling me what to wear and not to wear most of the time. Quote " Honey your not wearing those jeans go change and hurry cause we're late as usual"
Really though my wife when I told her I enjoyed CDng actually did make me up and bought me my first bra, hose, heels and dress. I still have yet to attend a Halloween party.

[Fiona123]

Not me but I would love for that to happen!

[LilSissyStevie]

When I was little, we lived in a semi-rural area. There were no boys my age to play with. I didn't like playing with the boys that lived in the area because I was small and timid and they were big, stupid and violent. So I stayed near home and played house with my sisters and their friends. Sometimes I got to be the Mommy and would wear one of my sisters' dresses or at least a pinafore. It was all pretty innocent. They got a kick out of dressing me up as a girl. I didn't really think too much about it other than I preferred the company of girls. My grandmother would occasionally smack me upside the head and shame me for being a sissy and playing with girls. She would then make me go out and play with the cretins down the road. I would take my dog and disappear into the woods instead.

Edit:

It never happened on Halloween though, but my sister would have been up for it if I wasn't too chicken. I went to a Halloween party once and there was this person dressed in either a Snow White or Alice in Wonderland costume. I don't remember which. I do remember thinking she was very pretty. When we had a best costume contest at the end of the party she won the contest and it was revealed that "she" was actually a boy. I do remember feeling very envious.

[JocelynJames]

Years ago my first wife was going to have me do the cheerleader thing for Halloween. I was over enthusiastic and she responded with a " oh God, you're not going to start cross dressing are you?!" Start... starting was about 12 years or so prior. I ended up going as Tom Cruise from Jerry McGuire. Some other guy was Marv Albert-headphones and suit up top, garter belt, stockings, heels and panties below. He won ,the contest and my envy. The ex never knew the real me.

[michelleg]

As close as I've come was seeing a commercial for the Rocky Horror Picture show playing in a nearby cinema. I said we should go watch it and my wife's first question was what did I plan on wearing? We didn't go, but I would like to be a French Maid for Halloween one day.

[oh to be rachel]

We've gone out to a couple of halloween parties. It is always fun.

[audreyinalbany]

unfortunately, dressing for Halloween is to 'jokey' for me...you've got to camp it up too much for my taste.

[Jayne44C]

A former friend and ex bartender told me I have a feminine look and I should go out in drag. She even went as far to tell, prematurely so, a few of our mutual female friends she had convinced me to. They were all going into NYC for some underground Halloween party. She offered to "do me", make up, wig, chose an outfit, etc...I turned her down for two reasons. I am closeted and have been pretty much all my life. As such going out and looking 'too real' might have given my secret away. I would have to quit that bar, as a patron and probably gotten a new set of friends. In retrospect I wish I had done it but, it's water under the bridge.

[SaraLin]

Growing up, we were too poor to afford real costumes. Most years it was one of those cheap plastic masks (You know the ones.)
But - one year, my mom decided to just put me in one of my sister's dresses, slap a (clean) mop head over my hair and send me out. No undies, sadly - but hey you can't always have everything.

I secretly loved it, but didn't say much. I was too Scared to speak up for myself back then about ANYthing, let alone my wanting to be a girl (long story and not for this forum)

One of the neighbor ladies loved my outfit and I can still remember the phrase she used. She said I was "The cat's pajamas." I'd never heard the phrase before, so it stuck in my memory.

[Michele14]

Last year I went as her and she went as me.
Michelle

[Sheila11]

Growing up, we were too poor to afford real costumes. Most years it was one of those cheap plastic masks (You know the ones.)
But - one year, my mom decided to just put me in one of my sister's dresses, slap a (clean) mop head over my hair and send me out. No undies, sadly - but hey you can't always have everything.
I secretly loved it, but didn't say much. I was too Scared to speak up for myself back then about ANYthing, let alone my wanting to be a girl (long story and not for this forum)

.

Exact thing for me at about age 10. No mop on my head but I think there was ribbons.

[Suzanne Blake]

Unfortunately no. I don't remember any boys dressing up as females for Halloween when I was young. And now that I'm older, I'm not really into Halloween.

[Majella St Gerard]

my 1st wife helped me dress as a woman on Halloween, I wasn't into cd-ing per se at the time, it's what hooked me, anyway, she went with me to pick out the panties, stockings and wig. I would wear her clothes to the party, I bought the shoes on my own, had to return them twice before I finally just tried them on in the store first, very quickly. 20161027_191353.jpg

[redtea]

I wore a wig to a pirate costume and had a older girl fix my hair for me. Looking back, I don't think I savored the experience enough, nor will I ever be able to wear a wig for Halloween again due to the context changing.


I do fantasize a lot about being dressed up for Halloween and having the girl use a lock on my dress so I can't run away.

[Karmen]

A woman friend I have for a long time and we go partying together sometimes, convinced me to dress as a "lady of the night" for a Halloween a few years ago. Of course, I didn't put up a lot of fight. Why would I?
We went shopping next day and I bought short sexy black dress, red underwear and red net pattern full body pantyhose and black sandals with 4 inch heels. I could all that and prettier stuff took out of my closet at home, but that would definitely rase suspicions, because she knows I was never before dressed as a lady for Halloween. And I paid for all of that less than 100€, so there was not a big deal anyway. She already had at home a wig with curly long blonde hair, so we luckily didn't have to buy one of those cheap Halloween wigs.
On the Halloween day she applied strong makeup to my face and beautiful red nail polish on my nails. We stuffed my new push up bra with napkins and on top put silicone breast forms women sometimes put in their bra, so their boobs appear one size bigger. She has small breasts and use them in her bra sometimes. I must say it looked quite cool and made an impressive cleavage. She had a pimp outfit in her closet already, because she used that before. One of her women friends also joined us (the second lady of the night, but I must say much prettier than me) and we were ready to go out. We had a great time and both women were really fascinated how well I walk and dance in those heels and I didn't have any problems wearing them the whole night. Ok, I got blisters, but that was expected because they were cheap new shoes.The one thing I didn't give any thought before when I agreed with this Halloween idea, was my walking. Both women were very suspicious about my walking skills and teased me for a while with that. They just knew I was walking much too confidently for someone who suppose to learn that in one day from looking youtube video tutorials and walking a little around the house in heels. I was for a moment even considering coming clean and admit I'm a cross dresser, but I knew if I tell them, everyone would know soon. They just can't keep a secret and I'm not ready to come out yet. We done the same setup a year later and it was a blast too and I didn't get blisters this time.

[Dana44]

Did not happen to me. However a male has told me to shave my legs and go out on Halloween in a dress. Yeah I wonder if he was a cross dresser.

[Dian077]

When I was in high school, my girl friend dressed me like a girl for Halloween one time. We were about the same size and she had some really neat stuff. I felt so sexy. It kinda turned her on too I loved it. She did not know my interest in dressing. Wish I would have done it more often though

[Rachael Leigh]

My wife didn't dress me but did allow me to go to a party as a French Maid.
Had fun with it too, answered the door a couple of times as guests arrived as if I were the maid lol

[RADER]

My Wife dressed me up as a French Maid for a few Halloween's.
I gave out the candy dressed that way; lots of fun.
All the "Mom's" thought I was cute, The "Dad's" just shook their head's.
The Kids showed no interest.
But I Had Fun.
Rader

[Cdkym]

A GF of mine 15 years ago suggested that I go to a costume party (not at Halloween) as a cheerleader. She helped me with the make up and I wore her old high school uniform. I had a blast that evening most of the people at the party did not know me and I got my butt pinched more than once by the guys at the party. She went dressed as a biker dude and on the way home after the party we stopped at a diner for desert. Five minutes after we sat down some cops showed up and came straight to our table to check on me, I guess someone with bad eyesight called about a biker Messing with a teenager. Lol we laughed about that for a long time. BTW the cops were cool once they saw our ids. They laughed about catching of parked in a dark make out spot and having to call my parents.