Do you have Great Cross dressing Memories from Christmas's Past

Ever since I was young, Christmas always brought out so many fun Cross dressing urges.

Of course being born closely in the middle of 2 sisters was a recipe for disaster !

To start with was my mom taking my sisters shopping for their annual Holiday Party dresses. Early on I made the mistake about asking my mom about cloths for me and she teased that anytime I wanted to try on pretty dresses with my sisters I was welcome. later of course my sisters would model their new outfits for all to admire and compliment.

A few years later my sisters were given matching frilly pink babydoll nighties. I think at that point I started to realize I had a problem because I couldn't keep thinking about how fun it looked to be wearing a babydoll. Well of course at some point the opportunity came and once a boy steps into nylon panties with ruffles on the butt their is no going back ! LOL

After that For many years any Holiday party dress they ever got I at some point tried on! Only wish i had pictures !

Later in life it was all about the Holiday Frocks the ladies would wear to parties ! Yes I was Jealous !

Anyway hope this was always a fun time of year for all of you and that you have fun memories

I few years ago I got to decorate the tree wearing a black velour godet skirt, off black hose and a green cowl neck sweater.

Robbie,
My memory is a recent one from last Xmas when I played host and cooked the meal for my daughter and her family , I wore my Xmas dress the whole day .

Yes, I do! Fortunately, one of my daughters lives in Vegas. We usually go to her house for Xmas because she has 2 kids.

While I can't dress in her house because I'm a closet dresser and many in the family don't know about Sherry. But, it does allow me to dress away from her house. We usually stay for a few days and I stay in a nearby hotel.:battingeyelashes:

Attachment 308976
Attachment 308977

My very first crossdressing memories happened at Christmas. I must have been 4 or 5 and my baby sister had on a pretty holiday dress with white tights. I wanted to know what the tights felt like so she took them off and...yep, ever since☺ Later, as an adult every year my Christmas shopping would inclue a few pairs of pantyhose for you know who.😉
Merry Christmas everyone!

Somewhere in the early 1980's I bought myself a vivid red Vanity Fair bra and panty set. I remember getting somewhat of a sneering look from the guy behind me at the checkout line. I suspect that guy never bought his wife any lingerie. Years later our three year old daughter opened the bottom draw of my armoire, opened the small box of unmentionables I stored in it, and, yanked out that red bra. My wife found it and took it away from her. That incident precipitated "The Talk." She asked "Why would a guy wear a bra if he has nothing to pack into it!" Touche!

One year my wife got me this 1950's dress. with 2 petty-coats. It was a dream to wear.
I wore that dress on at least 3 Christmas.
Rader

A few years ago I went with my best friends family Christmas dinner.

I have been invited back every year since.

I can't express how much this means to me. It's not just their acceptance, it's more than that.

I was with my BFF yesterday , she asked if I was going this year? I said yes, now I have to find the right dress, hopefully I'll find it in my closest.

Well, my greatest Xmas memory in this vein was the first one that I came out to my wife.
She had a company party just before Xmas and when she left I spent the evening prepping. Complete body hair removal, bubble bath, lots of time on my makeup and a lovely holiday outfit.
I was nervous and anxious waiting for her to return and when she did it was so much better than I had hoped. She was calm, respectful, inquisitive and we spent hours discussing everything from my attire to my feelings and hers as well.
Since then it's been wonderful being able to be me whenever I desire and I remember that Xmas fondly every year.

This will be the first Christmas that I will be "dressed"! I have a Christmas nativity scene pin, wreath earrings and found my wife's Christmas ball necklace! I also want to attend my work Christmas party(no alcohol!) ! I have come out to all the staff but one in the kitchen and only one has seen Lana Mae in the flesh! Those at the Christmas party will see Lana Mae for the first time! Most have been totally accepting being shown my pics! So we will see how they like the real thing! Lot of firsts this year! Merry Christmas everyone! Hugs Lana Mae

Christmas time 1980 i will never forget.Back in those days i used to suppress for a while then let the pink fog hit over and over again thru the year.
So in 1980 Christmas was very close and i happened to be watching a Laurel and Hardy movie(march of the wooden soldiers)when i suddenly started noticing how lovely and feminine the one playing Little Bo Peep was and the PF rolled in really thick.And just had had had to get in girly mode.Felt so heavenly that whole week.

Never had a Christmas like that before or since.Usually had get togethers with extended family at holidays but not that year,so had alone time.
That also marked the first time using pressed powder foundation and falls.

two - when I was very little, I wore Sis’ high-collared flannel nightgowns when it was really cold out or I was sick (which was quite often); even had one on for a Christmas morning when I was six.
Mom and Dad use to make movies of Christmas mornings as we entered the living room and then opened packages. It must have been a cold night or I was sick (or both which was fairly regular in the winter), as on this particular Christmas morning, the movie starts with Sis and I coming into the living room, both wearing long white ruffled flannel gowns. The movie runs for about 5 or 6 seconds then does a jerk stop and start. At the restart, I’m now wearing my long dark blue robe over the gown, and while the top/collar is now tucked in to the top of the robe, the ruffle is still plain as day out from the bottom for the rest of the movie.
The second was the Christmas after I transitioned. Its a long story, but suffice it to say my Wife and I wore matching gowns to the company Christmas party...in 1982

Sure I do! All throughout my middle school through high school years, everyone else in the house was off to work during the Christmas holiday break from school, so I got to spend every day at home, dressing up in my sister's clothes all day long.

Kim,
I was a nervous wreck.
Would she make fun of me, would she laugh, would she .... (fill in the blank).
Here I was completely hairless for the first time, completely dressed and made up and NOT peeking out the window ready to run and change and hide everything. I was about to actually allow someone else to see me for the very first time.
It was at once the worst day and the best day.

I do back in the days when my wife and I had just begun our relationship and she was accepting and involved with my support group in Denver back in the early 80's she gave me a very nice sweater and matching slacks for Christmas. I was quite surprised and pleased. She was way more accepting than I ever anticipated. UNfortunately she is no longer accepting as she was and my dressing as taken a step back. All the good times back in Denver were before children. Thirty plus years latter in So Cal. things aren't the same. She puts up with my dressing but wants nothing to do with it and so far thats fine because it forces me to keep cross dressing in perspective and not get carried away with it.
It works for both of us.
I still wish I had that sweater. I don't know what happened to it

I guess I don't have any special CDing memories but do remember gazing rather longingly at those few "special pages" of super feminine robes & nighties that appeared in both the Sears and Penney's Christmas catalogs.

Ummm... didn't they call them "wish books?" :)

Lacy PJs

My best memories were just after i started buying my own clothes as a teenager .My parents would go away and my brother would basically stay at his GF's .Had the house to myself with basically no worries .My favorite outfit was a black skirt with a white blouse and nylon camisole underneath .I would basically go all out with the makeup and try to do my hair and nails to the best of my ability

At family gatherings I'd wear panties and bra underneath skinny jeans and a loose t-shirt. It was a secret thrill for many years.

hello Robbiegirl,
every Christmas Santa forgets to bring me dress I requested.
luv J

Before we were married I told my wife that I dress.
The first Christmas together before we were married she came over to my house with wine and numerous packages. She had me dress and then she did my make up.
She then gave me the packages to open. She gave me several outfits, which I had to model, jewelry, make up and intimate apparel.

My fondest memory of a Christmas in fem was when we lived in Ft Lauderdale area and attended the local Tri Ess groups annual Christmas Party. We went to a nice place to eat that had a back room that they reserved for us. We had to walk through the restaurant to get there. With it being busy I worried that I would be discovered as male. Apparently I passed and was actually complimented by another patron that I looked nice! The party itself was a lot of fun as well. The organizer had us bring a wrapped $20 gift for a gift exchange game they played a game where you pick a gift or you can choose something that someone else had already opened.

I've had other Christmas' where I've received fem gifts but that was the most memorable...?.and that was 6-7 years ago. The local group here do ok with their parties too but I think the compliment kinda made my night for memorable.

Three years ago, my fiancee (now wife) bought me two new wigs. Around mid-Christmas Day, her best friend (effectively a sister), who knows about me, gave me my first doll, a Barbie. We immediately, um, posed her with GI Joes we'd bought at a thrift shop.

None whatsoever.

But this will be my second xmas since I decided to accept and act upon my desire to xdress.

This year was the big year. I finally admitted that I've wished for years that I'd have a couple of cute items under the tree (and on birthdays, anniversaries and valantine's day). She took it to heart and picked out some really nice sweaters, panties and pj's. A couple of items are almost stealth and I'd like to go out for a nice dinner wearing them. She's a little hesitant, but not totally negative about the prospect. Even if it doesn't happen, I've got some really nice new things. It feels good.

Before the tree comes down, I don my favorite outfit that I purchased within the last year and take a few pictures. Not exactly "great" but I do look forward to it all the same.

Not great memories, but I remember the last purges.