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

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.

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.

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!:brolleyes:

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.

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

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.

Not me but I would love for that to happen!

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.

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.

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.

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

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

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.

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.

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

Quote:

---

Originally Posted by 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)

.

---

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

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.

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. Attachment 283411

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.

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. :)

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.

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 :)

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

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

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.

Yes bliss! My GF loved when I would go out dressed in public and would hint to people that I enjoyed dressing up 'too much' ! We spent three Halloween's together, my favorite being a female flight attendant (she was a pilot with stick on beard). Navy Blue pencil skirt, hose and heels, white blouse, matching tight navy jacket and bobbed wig. It was the best !

After I was divorced after 23 years of marriage, a girlfriend wanted me to dress as The Church Lady because she wanted to go as Ross Perot. I had never dressed before that and never even considered it. I reluctantly agreed to it just because I thought I needed to shake myself out of my male oriented opinion not to dress as anything on Halloween. I had to purchase a pair of size 10 red high heels and she provided everything else. I agreed to shave my mustache, legs and under-arms. We had great fun with her helping me while drinking wine and getting ready for the parties we were going to. When she finished my make-up and placed a wig on my head, she stood back from the mirror and exclaimed, "My God! You really are Glenda". I just stared at myself in disbelief and realized that there had always been a female side of me that I never knew of. At the parties we went to that night, all of our friends told me how naturally I had adopted a female persona. I haven't grown a mustache since that day and have come out to almost everyone I know since then.

Had many offers, passed on them all. regretted them all too. The first time I decided I wanted to go out, I did. My SO didn't help with anything (she was working) but was amazed at how well I did everything. Many years later I told her and have been enjoying Halloween ever since.

Many years ago when I was 25, I had a girlfriend who did not know that I liked to crossdress. We went to a bar for Halloween one night, me as the Joker and her as a hula dancer.

Then on the weekend we hosted a costume party. My girlfriend suggested that we trade costumes. So she dressed me as the hula dancer with her grass skirt, stuffed bra, and halter top. I had a blast! My brother noticed and said I was having TOO much fun. I wonder if he really suspected. It was such a fun night for me.

I dressed myself once long, long ago and my wife dressed me once long ago. This was back before I was really into crossdressing although I did sometimes wear a stuffed bra when nobody was around. Both times it was a "joke" and I wasn't intending on passing.

I wouldn't want to do it now because I would want to do my best and friends and acquaintances would easily figure out that I didn't just dress as a woman once a year. Now if I found a party where nobody knew me or my wife, it would be a different story. Krisi would make a public appearance for sure.

Not for Halloween, but on a dinner cruise in Hawaii, of all the males, I was chosen to be a female hula dancer. We went below. After I took off my trousers and put on the grass skirt, two girls did the rest: stuffed bra, wig and lipstick. Back to the party, I hulaed as best I could, including tush wiggles, and butt bumps with the real hula girls. My wife took many photos. As a reward, our drinks were free. I stayed dressed until the cruise boat started back to port. I was a very closeted CD at the time and had a blast!!

No, never have . I believe I would thoroughly enjoy that experience.

As a youngster, I would pester my mother well in advance to help me create a Halloween costume. She knew I got a kick out of Halloween, and we both put a lot of time and energy into making my costume as good as it could be. At age 11, I found myself looking through a bunch of stuff in storage in preparation for Halloween. I came across boxes with some of my mother's clothes in them, and decided I would dress completely as a woman for Halloween. I bounced the idea off mom and she gave me a "let's see what we can do" reply. Her thinking at the time was once of doubt. "Really...you want to wear everything? she challenged. "Sure" I answered, "I want it right, don't want anyone to know who I am, that's the fun of it." As luck would have it a couple of her things didn't fit all that well and couldn't be easily altered. An aunt came to the rescue with those items. Between the two of them, I was given lessons in deportment, (keep your knees together when you sit, stoop don't bend over, etc.) and how to walk in somewhere between a 3 and 4 inch heel as I recall.

The following year was a first for me, I wore the same costume two years in a row. Well not exactly the same, we did make some changes as I had grown. At the end of that Halloween night however, my mother suggested that although I had great fun dressing like that, I was getting too old for Halloween, and that it would be best if I stopped dressing like that.


Karen

Quote:

---

Originally Posted by Jenny22

Not for Halloween, but on a dinner cruise in Hawaii, of all the males, I was chosen to be a female hula dancer. We went below. After I took off my trousers and put on the grass skirt, two girls did the rest: stuffed bra, wig and lipstick. Back to the party, I hulaed as best I could, including tush wiggles, and butt bumps with the real hula girls. My wife took many photos. As a reward, our drinks were free. I stayed dressed until the cruise boat started back to port. I was a very closeted CD at the time and had a blast!!

---

I think that would be every crossdresser's dream - to be "forced" to dress as a woman for a party.

Quote:

---

Originally Posted by Christina Page

My brother noticed and said I was having TOO much fun.

---

The party that my wife and I went to, I got this comment a lot. I found it personally very small minded and rude. It was accompanied by comments to my wife to "watch out, he might like this too much!" Really frosted me.

Other than a couple of small minds and a bunch of handsy guys, it was a spectacular evening though and I'd do it again in a heartbeat.

Quote:

---

Originally Posted by Christina Page

My brother noticed and said I was having TOO much fun.

---

"Too much fun,what's that mean,
It's like too much money, there's no such thing."
-Tracy Bird

yes my mother did whan I was 9 and a couple of people thought I was a girl

Not since I was 11 years old. Though the wife and I have talked about it Kids take priority on Halloween

My very first time out dressed was after college, I was living in Tennessee. A volleyball playing girl friend of mine, Nita, wanted me to go to her Halloween work party with her as a Playboy Bunny. That's when I was young and skinny, and with a little beer, could be foolish.

She was tall, and her feet were pretty big, so she gave me a pair of blue Candies high heeled mule sandals that were on their way out. I cut the strap and laced some blue shoe laces through to make them a little wider, then wrapped the laces back around my ankles a few times before tying them. Having worn my mom's heels many times as a closeted high school cross dresser, they were actually very comfortable, and I was able to walk in them all night. (At one point later in the night, someone told me I could take off the shoes, but, NO WAY!) I've loved strappy heeled sandals ever since that night.

Nita bought me a blue leotard and tights and brought me a shoulder length brunette curly wig that matched the color of my hair perfectly. I cut up a white shirt to make my collar, cuffs, and bunny ears. The ears were made out of a coat hanger and other miscellaneous stuff to give the fit and strength. I bought a lacy apron to cover my other parts. I can't remember what I used for my puffy tail. (?)

I have such fond memories of sitting in her apartment dressed in my bunny outfit while she painted my nails and did my make up. Naturally, Nita went as Hugh Heffner (RIP) in jammies and a robe and slippers.

Why is the first time always the best? That was a great night. I spent much of it serving drinks, getting leering looks from the guys and jealous comments from the girls about my legs. Oh, and getting my ass pinched!

Years ago my then wife and I were invited to a neighborhood Halloween party. I was certainly a CD but early in my journey--owning no femme clothes and not out in the least. Brain storming ideas on the way home from a second unsuccessful costume hunting mall trip she, out-of-the-blue, suggested that I could dress as a woman. She saw a couple guys do this at a party a few years earlier (pre-marriage).

She worked Saturdays and I didn’t so that was my time to put together an outfit. Under the cover of Halloween I haunted the local thrift stores for the perfect “costume” trying on many looks in their terrifyingly not-so-private changing rooms. Thinking back, I had an amazing time and don’t remember any problems with the clerks or other shoppers. I finally settled on a red and white skirted, sleeveless majorette style uniform (yes a cliché by today’s standards) and red vinyl knee boots that were just out of style, so thrift store plentiful. I also purchased needed accessories—bra, panties, pantyhose and a thrift wig. I did all this with no previews and naively not expecting any problems.

The Saturday before the party I did the big reveal when she got home from work. I had even shaved my hairy legs and arms. I though I had made great choices and put in 100% effort but she just stood there in stunned silence. When she recovered she made it clear that I would not be wearing this costume as everyone (including her probably) would think I was gay. She didn’t consider for a second that I was just a crossdresser. Her idea of a man-in-a-dress costume was a flowered granny dress, rolled up shorts, hairy legs, red lips and tennis shoes. Not my look.

In order to make peace, I didn’t go as a majorette that year.

Not for Halloween but my sister had a Halloween themed wedding. My wife went as Charlie Sheen and I was the hooker. The girl that had been helping me with my makeup came over and worked her magic. As my wife looked on. she doesn't wear much makeup her self. I had a few people ask if my feet hurt in my boots? Being new they did so I did say yes. They would respond with oh good if they didn't I would have thought of you differently. :eek: All the clothes were mine since I have been on this journey for a long time. I loved being dressed but my wife wasn't thrilled with her costume. I would do it again in a hot min!!:daydreaming:

Yes. My wife, who knows and supports my dressing. For several years, I off and on, dressed as a extravagant drag queen. A couple years ago, I/we decided to go for realism. Even though I have-an extensive wardrobe, we bought a beautiful black cocktail dress. We went the whole nine yards. Perfect makeup including false eyelashes, shaved legs, chest, armpits, hip pads, D cup bra, waist cincher, etc. I decided to wear my 3 inch heels...am still working on 4 “ 👠. I went in first and no one knew who I was. Loved it. Later, the wife of one of my friends told me how great I looked. I think (ESP) she sensed I didn’t get this way overnight. We’d all had cocktails and wine. She asked me if I’d chat with her....red light !!! I gave my wife all the credit...she didn’t buy it. Ha.
It was fun chatting with her about girly things. A week later, i bumped into her at the grocery store. She remarked again how pretty I looked. I just thanked her. As she left, she smiled and winked at me. I’m convinced she knows or highly suspects. I told my wife....no problem. Yes, I’ve worn the dress several times.