Did it all start at Halloween for anyone?

[caitlyn louisa]

I'm curious if a life long cross dressing habit was started at Halloween for some? The first public outing perhaps in feminine finery and a chance to bring together clothing, makeup, shoes, ratings, wig and maybe lingerie? The thrill of showing a soft feminine version of yourself that felt wonderful? I know that my first Halloween experience meant that I could never go back to a life without dressing up.

[bridget thronton]

Halloween was my first public outing (Nurse) but not my first cross dressing experience

[Cheryl T]

Not my beginning, but my first venture out in public.
Went to a friend's party and wasn't recognized for like half an hour. What a great feeling that was.

[Shiny]

It was kind of my end actually. I never dated much and was pretty much a loner and showing up dressed once seemed to give others questions or at least raise eyebrows and whispered voices that took months to abate. Only did it a couple times but that was enough for me.

[Stephanie47]

My crossdressing did not start at Halloween. Although I had gotten totally en femme for evening drives and strolls, Halloween was the first time I intentionally mingled with other humans. It was not much of an interaction, but it was my first. I wore a below the knee jade floral print dress, black heels and hosiery, and a blond wig with full makeup and nail polish. I interacted with a woman who was the counter person at a Winchell's Donut House. She complimented me. It felt great even though I was full of apprehension doing it.

[oh to be rachel]

A couple of Halloweens, once dressed in wedding dress and once in a dress, in public settings told me emphatically "I Like Doing This!"

[docrobbysherry]

I had been dressing in the closet for about a year. But, I was about ready to give it up. Because I could present a pretty decent female figure. But, with my ugly, old man face I looked hideous!:doh:

Then, Halloween came and I tried on a female mask and Sherry was born. That was 25 years ago and I've never looked back!:battingeyelashes::devil:

[kimdl93]

You know, I have never gone out dressed on Halloween, not counting child-hood trips in cowboy mode, or more often a parka with a plastic mask. Halloween tended not to be great weather where I grew up.

[MarinaTwelve200]

Back in the 60s, after moving from North Carolina to the gulf coast , I discovered that Teen and younger Boys dressing as girls on Halloween was a really big thing. (Perhaps the Mardi Gras Influence) Many, if not most of my friends did it when we went on our Halloween Trick or treating. Looking back, I can see it was an excellent opportunity to dress in public and no one think anything of it, but I was very "Closeted" and never went out dressed.----Missed opportunity. I bet my mother would have cheerfully helped, but I was too scared to ask.
HOWEVER, just a few years ago I DID finally dress and go out---And it WAS to our Adult Sunday class Halloween party. I did it as a ploy to Shock and inspire our group to get back into COSTUMING for these events---as Costuming was beginning to trail off. I first thought of simply doing "A woman", but that was plain and uninspired, but then I got it! I went as a "GYPSY FORTUNE TELLER" it worked well as both a FEMALE and Something Halloween themed. I got to wear an exotic costume and makeup. Needless to say , I was a HIT. All the ladies lined up and wanted me to read their cards. (Great way to meet chicks!---if not unconventional) I WON first place in the Costume contest.

My ploy worked even better than I hoped, We had great costumes the next year--so good that my dead-on MARK TWAIN costume only won SECOND place.--I got beat out by an 80 year old "Pregnant Nun". ;)

[docrobbysherry]

Marina, u found out early on how to CD on Halloween and get away with it. :battingeyelashes:

Don't dress up as a woman. Dress up as a costumed woman and u may not be nailed as a CD!:thumbsup:

[VtVicky]

I'm not sure if this really counts as "crossdressing", but it felt pretty good to me at the time.

Some of you may remember a famous football player named Joe Namath. At one point he was featured in a pantyhose advertisement wearing the product.

Well, I was a young USAF officer with a wife and kids, living in base housing, with zero opportunity to dress. At some point I figured that I could go to a party dressed as Namath in his advertisement wearing pantyhose, a football jersey, and carrying a football.

I loved it. But, I am sure no one had a clue what was going on in my head.

Hey. It was a start.

[Jillcder]

Great question not necessarily the start of my dressing but it was definitely more than just a costume to me.

[April Rose]

I only did it fully once, and it was an awkward and unsatisfying turn of events. It turned me away from trying it again.

[Taylor186]

Like others here, Halloween was my first en femme public experience (age 31), but it was not my first time crossdressing.

[wendylovescd]

I've only done it once (in the early 2000s), but it was pretty frightening and exhilirating all at once. My wife wanted us to go as Linda Tripp and Monica Lewinksky to a party she was invited to. She knew and was okay with me wearing pantyhose and I had shown her a picture of a crossdressed me somewhere along the way so she knew I had done it before. But at the time, I didn't really have anything (purged after a prior divorce) so she proceeded to find a dress, wig, and some short heels at a thrift store - (they were a squeeze!) as I'm a 15 heel. Like many have said I was terrified to be outed because of how easy it was to walk in tight heels and nice looking legs. My wife did my makeup and I think somewhere along the way she commented (and maybe was a little taken aback) at how comfortable all this was to me with the exception of having to "act" like it was difficult at the party. I've not done it since and I suppose if the opportunity presented itself, I'm not sure if I would do it again. As far as starting, it opened the door a little with my wife be okay with me being a CD although we've had ups and downs with it and perhaps gained clarity about each others needs and expectations.

[alwayshave]

Neither my first time dressing nor my first time out dressed in the wild.

[Brandie.n]

Yes for me i was a witch.

[TheHiddenMe]

No, but I was envious of the boys who got to dress for Halloween. I first wanted to dress when I was about 7, but my turn for Halloween didn't happen until I was 13 (and after that, it took almost another 50 years).

Below, Halloween 2021.

[NjJamie]

Caitlyn, the answer for me is a bit complicated. My mom dressed my brother and I as young girls for a church costume party, me in a skirt and sweater top borrowed from a neighbor and white go-go boots from her closet.

I was about 11 and while I remember quite a bit from the party, including a walk down the runway for judging, it wasn't until a few years later when I was alone in a spare bedroom when I felt some need to try that outfit again. I managed to put on the pantyhose and the boots when suddenly a new feeling/identity seemed to come out of nowhere and almost knock me over.

I now know it as the pink fog and have spent the last 50 years trying to recreate that feeling of "comfy newness". I've tried to get out for Halloween but as with many CD's, I knew I was likely to get so deep in the fog that it would've been too obvious, at least I believe so. From being able to walk well in heels, have too comfortable a walk or mannerisms, I would so love to but probably will not follow through on celebrating our greatest holiday!

[SaraLin]

Halloween certainly was NOT the cause, or the trigger for my attraction to all things feminine. That has always been there, stirring restlessly inside me, begging to be let out.

I'm not sure If Halloween was my first time out in public.
My memory isn't all that clear whether it was the Halloween that my mom allowed me to dress up like a girl and go trick-or-treating,
OR
if it was the Cub Scouts where I was in a play as the "damsel in distress."

Either way, whichever one was first - neither one was any sort of trigger or "starter" for me. I've always knows I should have been a girl.

[JamieG]

Halloween did not start my crossdressing, but did help me to become more comfortable with it. I first wore tights in public one Halloween: I wore a unisex jester costume: hat, tunic and two-toned tights to a party of a friend-of-a-friend. I knew practically no one there, but had a good time. Met several girls who normally wouldn't have given me the time of day, but liked my costume. Many years later, my wife and I went to a Halloween party dressed as female pop stars.

[Joyce Swindell]

Good question!!
It's weird but in all of my years I've only dressed up in FEM once for Halloween. It was a family gathering and I wore a white very lacy dress. Did my makeup poorly on purpose to not give myself up. Drove there separate from my wife in my dump truck!

[AllieBellema]

Halloween has always been my time of the year to come out and dress up. I did use it as an excuse to buy my first dresses, including my first southern belle dress. Every year up until the pandemic, a local friend of mine's familly would throw a Halloween party and I would use it to wear my princess cosplays or southern belle dresses. But since the pandemic started, they haven't really held those parties anymore so I don't have anywhere to dress up at right now.

[Jenn A116]

No, it didn't start with Halloween for Jennifer. In fact, she's never been out for Halloween.

[Sandi Beech]

It did not start with Halloween for me but I have surely had some wild and crazy Halloween outings over the past 5 years or so.

Sandi

[Karren H]

Not for me. I started at the age of 7. And never really associated crossdressing with Halloween until coming here.

[Monique65]

Reading this thread brought back fond memories of my first and only time out in public dressed en femme. I was in my mid teens and told my mother that I wanted to attend a Halloween activity in another town dressed as a girl. She gave me a skirt and blouse and tied a pretty scarf around my head. I wore my sister’s Bobby socks and tennis shoes. What she didn’t know was I had borrowed a pair of my sister’s panties and a bra in order to feel complete.

She dropped me off at the event, and I spent several glorious hours roaming around feeling very feminine. I wasn’t worried about seeing anyone I knew, just enjoying the chance to explore my surroundings. At the end of the evening, she picked me up and I had to relinquish my attire, but the feeling remained. Unfortunately I never had the opportunity to repeat it, and it has become one of my treasured memories.