Have you Ever had chances to Be Dolled up by Women for Halloween

[Robbiegirl]

That you either accepted and had an experience to remember or that you turned down for reasons you maybe now regret ?

I was right between two sisters but oddly enough never had my mom suggest I wear one of their cute costumes ! Damn


I can certainly remember women when I was single joking about it but never really seriously approaching the subject in full detail. Once a group of gals in my office all decided to dress as Bridesmaids. I so hopped they might drag me into it but didn't . I hinted but I guess not enough

Anyone have any fun experiences or opportunities they wish they had taken, or did take.

[Nikki A.]

I had 3 coworkers do their magic on me one Halloween. When they first brought up the idea, I kept saying no, so I wouldn't seem to anxious. Had a great time that day, and I could blame it on them. I later confessed to one of them and she's been very accepting and been out with me quite a few times.

[fun4metoo2004]

I have a make up and hair artist doing me the night of a party. I am going to get waxed on 19th, and my nails done on the day of the party. This will shock all the people that know me at the party, but that is what I was going for.

Pencil skirt, wine colored blouse, black stocking, and 3 in heels.

[connie johnson]

Yes I have. My wife helped me and did my makeup one time for a big Halloween party downtown. I dressed sexy and she was a cop. I had a great time walking around downtown. It's the only time I've been out dressed and would love to do it again. Apparently I looked good enough that when I ordered a drink At one of the bars and used my male voice the bartender said nicely " damn. You're a guy". Either that or he was just being nice.

Hmm. Halloween is coming soon. Maybe I'll do it again ��

Connie

[sometimes_miss]

I used to dream about it when I was young, but the opportunity never came.

[docrobbysherry]

After 10 years of dressing alone in a vacuum, I came out online. A woman living nearby on a T dating site was a makeup artist and offered to help me dress, too.
At the time, 20+ years ago, I was looking for someone to date. So, I turned her down because she wasn't my type!:straightface:

[Shely]

I too dream of such a Halloween party, but my wife won't hear of me going as Shely. Dang!

[NjJamie]

Robbie, the first time I ever dressed was for a church Halloween contest at about 8 years old. My mom borrowed a few things from the girl next door, I didn't win anything but the seed was planted. Five or so years later I found myself in a spare bedroom with a closet full of women's clothing and for the first time felt that "need".

I'm still trying to recreate the excitement of that first time, going as far as I can and enjoying the adventure. I'd love to do a big Halloween night but my wife knows what is really behind it and rightfully knows I might enjoy it so much that whoever is at the event will see it's more than just a costume.

{As I read this post over all I got out of it was that I need to try to make it happen!}

[Beverley Sims]

I have lived the dream a number of times, not at Halloween though.

There have been themed parties and costume balls I have attended all dressed and helped by my girlfriends.

Some of the costumes were lovely but I had to give them back to their owners.

[MarinaTwelve200]

Not Halloween, but at a Womanless Beauty Contest at church a few years ago---- However I could have done a better job myself

[evadan]

Seventh Grade in the '70's. I don't remember whose idea it was? My girlfriend and her friend dressed me in a plaid skirt, white blouse and boots. They tied up my long hair into pony tails and made me wear make-up. I protested the whole time but i was really enjoying it. Then we went trick or treating for what seemed like hours. I didn't want it to end. And the rest is history...

Cheers,

Eva D.

[Maria in heels]

I had my receptionist as well as one fo the women in the office help me dress and do makeup and nails at work in my office area one Halloween a few years ago. Then a couple of poses and i was off to go back home under the guise that i was going straight to a party for my kids, who they all knew as well. Some of the guys tried to get their hands on my photo as well as one co worker was caught staring at me from behind as i walked past, because he didn't realize who i was and was on the phone and turned around when he heard my heels on the tile floor....

[Maria 60]

A few years back my in-laws and myself dressed up at Halloween and went house hopping. We made one stop at my brother in-laws in-laws house, his mother in-law couldn't get over how I looked and for years later she was always telling me she wanted to see me dressed again.
A few years later we were at my brother in-laws for New Years and his mother in-law called me upstairs that she wanted to ask me something. She lead me to my brother in-laws room and she asked me if she could dress me up, she pointed to the bed and there a was my sister In-laws dress, pantyhose and bra on the bed. Her daughter came in and told me that her mother wants to dress me up and if I liked the selection of the dress she chose and they would both dress me and do my hair and make-up. I think I got a instant hard on just thinking of both of them dressing me up. I could kick myself in the head for refusing, telling them that they are both crazy and asking why they want to see me dressed again. They just answered to have some fun. Still today she still ask me that she wants to see me dressed again, maybe one day I make a special visit to her house.

[Crissy 107]

Maria, That would be a dream come true for me, too bad on the missed opportunity but then again there is still that chance. Next time I would say something like, let me think about it, and that could lead to a very positive and fun outcome.
Crissy

[NancySue]

I’ve had two. One was for Halloween as a drag queen. The other was a fund raiser vaudeville show with six of us dressed strutting around the stage like models. I think I was the only one completely dressed. My wife did my complete makeup including false eyelashes for both. I received several nice compliments from several of the women. One guy thought I was enjoying this a little too much...little did he know...I did!

[Stephanie47]

Having my wife makeup me up is a dream that will never come to fruition. I have gone out twice on Halloween in full makeup, including nails. I wore knee length dresses. I did not go to a party, but, I did make human contact in several stores. What irks me a little about getting dolled up on Halloween is my wife and I encountering my father-in-law in dress and wig with his then girl friend on his arm. He was having a blast, and, said nobody at the Eagle's recognized him. They must have been blind because he was not the least passable. Anyway, my wife does not recall that event while it is etched into my memory. I suspect she has blocked it out of her mind as too traumatic. Or she does not want to approach the issue and fears encouraging me.

[Dena]

I visited a friend out of town when I was 23, for a Halloween party. When we were discussing costumes she suggested dressing me as a woman, saying she had a dress I could wear. I laughed it off and didn't do it. I've been kicking myself ever since! I still wonder what the dress looked like.

My wife and I dressed as s***s for our first Halloween. Went to a club and saw Bo Diddley!

...or ladies of the evening?!

[Pixie_94]

Halloween is not celebrated in my country, so you can easily get the image.

[nikkiwindsor]

Nope...had to do all the work myself!

[alwayshave]

No I have always done my own makeup for halloween.

[BarbraAnne]

One Halloween (1976) my neighbors had me dress as a pregnant woman. One did my makeup and loaned me shoes and a wig. The other provided the clothes. We had a block party, so all my neighbors saw me. My first time in public and I had a great time. Later I changed to a regular dress and we (the ladies and me) went to McDonalds.296608

[Connie D50]

My mom dressed me twice once for Halloween (baton twirler) sister outfit. The second time was for a boy scout skit where I played a girl fan of a rock group. I of course had fun for both events.

[Krisi]

Once, many years ago. My wife did it to me for a Halloween event. Back before I really considered myself a crossdresser. It was really just a dress, bra and stuffing, makeup and pantyhose. No wig (I had pretty long hair at the time), no women's shoes. No way I would have been mistaken for a woman.

If I did it today, I would look far better and I suspect people would figure out that this wasn't my first time.

[Robbiegirl]

My mom dressed me twice once for Halloween (baton twirler) sister outfit. The second time was for a boy scout skit where I played a girl fan of a rock group. I of course had fun for both events.

Baton Twirler ! Wow

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