What is Your Fondest Memory of Crossdressing?

[Katherine L.]

For me it was the first time my wife saw me wearing a bra. I was 27 years old at the time and we had only been married about 10 months. A few months before, my wife had discovered my only article of female clothing, a bra, that I had hidden among the male clothing in one of my drawers. Not surprisingly she reacted badly to the discovery, including tears, anger and all the normal questions. In the intervening months, she said little about the bra, but at least said I could keep it.

On this particular evening, we were watching television and cuddling together on the couch. She was caressing my chest and playing with my nipples, something she knew I loved. I made the comment that if she kept doing that I was going to want to wear my bra. To my amazement she said go ahead.

I went back to our bedroom and put on my bra, filled out the cups with some of her panties, and replaced my shirt. When I returned to the living room I was both terrified and excited, but mostly embarrassed. She quickly eased my fears and we began cuddling and caressing again. After a few minutes she took me to the bedroom where we completely undressed, except for my bra, and made love.

We have now been married 35 years and since then she had seen me countless times in bras and other items of lingerie. Still, that first time remains my fondest memory ever of crossdressing.

[Jenny22]

My first time out with sister friends and having dinner. Thanks, Sherry and Cindi!

[Steph_CD_62]

I would have to say my fondest crossdressing moment would be when my wife saw me dressed in my lingerie for the first time. She was very accepting of who I am.

[KimH]

Mine was very similar, my first positive "out" interaction.

In my 20s I spent a beach week in and out of sundresses, skirts and my first ever bikinibat the cabin I was staying at. One afternoon I was on the deck reading in my bikini and had been pulling up a sarong when people came by. I wasn't paying as much attention as I thought I was and the guy staying in the neighboring cabin came up. I assume I looked like a deer in the headlights but he was very casual and exchanged a little small talk before heading in. It was only a few moments but the fact that the world didn't end and there and no angry mob appeared was a beautiful eye opener!

[SassyRoberta]

So I have been closet dressing with lingerie since 10 or so. My first time to fully dress was just this weekend. I went to a well known transformation service and bought all I needed. The artist made me look super. I had always planned to go back to male before leaving. I was so embolden by her work that I left enfemme and went back to my hotel. I did run in quickly however. Still what a first experience.

[BrendaPDX]

The first time I met a fellow CD for coffee fully en femme, I was terrified! But the world didn't stop turning, and the coffee experience turned out to be "just no big deal to others" and a life changing moment for me.

[NancySue]

Me too...the first time my wife saw me fully dressed. She smiled, complimented me and gave me a hug. I tentatively asked her if she?d like to see my lingerie. She paused and said ?if you want to?. I was a little hesitant, but I took my skirt and blouse off. There I was...full makeup, wig, bra, forms, panties, pantyhose, a half slip and heels..all black. She smiled and so did I. She asked me if I was comfortable. I just smiled. It was also the first time she teased me about finding underwires, pantyhose and heels comfortable. She hates all three...interesting..I can?t wait to put on...what she can?t wait to take off.

[SassyRoberta]

What a wonderful moment between you two. LOVE LOVE LOVE!

[Bea_]

I'd have to say that it was the first time she reached up under my dress to explore without warning...

[jacques]

hello Katherine,
probably the fondest memory is when I came out to my wife and she said "Is that all. It's only clothes, I thought you were going to say something important!"
I am still trying to process that!
Stay healthy
luv J

[Micki_Finn]

Oh so many to choose from... first time in full drag? First time performing? First time asked to perform? Pretty much any year at DragCon? All pretty wonderful.

[Zoeytgtx]

Being out for dinner and accepted as ?one of the girls? with a group of GG?s.

[Pumped]

Every time my wife says, "I think we need to dress up this weekend!" Which happens fairly often. We have our girl's nights where we dress up in anything from dresses to just some skimpy lingerie and do out nails and sit and talk or watch a movie. Some evenings I get so touched that she has accepted this so well I get emotional and teary eyes. It was just a short few years ago I was afraid the marriage was over.

[Kandi Robbins]

This will probably be viewed as a cop out, but my fondest memory is the last time. After 50+ years of hating myself for this, finally embracing it six years ago, I find complete joy each and every time I do so (I only do so with the intention to either go out in public or take photographs to share on my blog and Flickr page). I have been out well over 500 times, never a negative experience, almost always blissful. I have received hugs from total strangers (no more, these days, sadly), thousands of complements, had drinks and meals purchased for me, shared meals or cocktails with people I did not previously know, etc.... Every time out, a treat, especially now!

[DianaW]

I'm very new to crossdressing but I don't think I will ever forget how it felt trying on a dress for the first time. I actually let out a soft moan as I felt the dress encase my skin for the first time. And I knew in that moment that my life will never be the same.

[dominique]

For me it's got to be when I plucked up the courage to go out dressed for the first time. It was a feeling that I will never forget.

[Angela Marie]

After a makeover. I was relatively new to dressing and drove about 100 miles away to get a makeover. I have to admit I loved the look. Anyway I drove home and went to my bathroom to change. I looked in the mirror and thought "I really do look good. I should finally go out" I had never been out in public during the day completely dressed. Even at night I only rode in the car. I decided to take the plunge. I went to a market away from my home. As I got out of the car my stomach was in knots. I passed a man on the way in. He gave me a look that I guess can best be described as a flirt. I did some shopping and went home. No problems. From that point on I never had a problem going out dressed.

[MonicaPVD]

A few years back, I was traveling on business and had a day and a half to myself at the tail end of the trip. I spent that entire time dressed. Went shopping, sightseeing, and even met someone on line who I had drinks with later on. That was the first time that I actually spent more than a couple of hours as Monica and it was just amazing.

[Karine]

Mine is pretty simple. It was the first time my SO and I were fully comfortable while I was fully dressing up.
We were watching TV and cuddling on the sofa as usual.

[Stephanie Julianna]

Hard to pick just one. But they are all the same theme when I am passing well in public. Back in the '90's my then boyfriend and I were clubbing in NYC and we went to a new club we heard about called The Monster. (I think). Crossdressers got in free with their dates and single guys paid a cover charge. When we approached the guy with the velvet rope he politely told me "Sorry Miss, this is for Queens only." With my deepest voice I thanked him for his compliment and he smiled and held the rope open for us to enter and said something like "Looking Fine, Honey." So any time someone asks me when I transitioned or the general public totally accepts me as Stephanie is a fond memory in the making.

[DanniBell]

Two stand out: The first time I received attention from a man (a construction worker in a pickup) when dressed. He gave me a wolf whistle when I was in my family's backyard, wearing a short blue skating skirt and a loose red Mexican blouse, as he drove by. Just because I realized I was passing. I was only 14. But, still. The road across from our house was under construction forever, and the only vehicles that went down it were construction. I was far enough away that I felt safe enough to be seen by them after that, and I definitely was.

And then a couple of years later the first time my friend Kim took me to a party on the West side of town after really helping me put things together. Spent a couple of hours comfortably being her friend as far as anyone knew, feeling safe and confident and not running from attention....

-D

[Lucy Long Legs]

It has to be the first time I went out in public. I thought: there's no point in half measures so I went to a dressing service who did my makeup and I dressed to kill. At first I was scared but I realised I was doing nobody any harm and I had a great evening looking and feeling feminine and sexy. I've done it many times since and it's always great!

[Sheren Kelly]

My fondest memory was going to an alumni event as Sheren. I was the only trans person there and felt completely comfortable in my own skin, so much so that I now have an alumni (picture) ID card that recognizes me as a female alumni. https://www.crossdressers.com/forums/showthread.php?219518-Alumni-Association-Diversity-Dinner&highlight=

[Leslie Mary S]

The first time I went out fully dressed.
I know, I was cheating because it was for a charity and I had entered into the woman-less Beauty Pageant. Back stage the other contestants where asking me for tip and hint, and help. Some of them didn't realize I was a contestant and thought I was a woman there to help them.
I didn't win. The winner rightly so, was the person who had raised the most money (a real fireman). But after the show my two of my GG model friends and I went to several places about the small rural red-neck town and had a lovely night.
I found the batch of photos from that night.

314896
Here is one.

[Brenda Freeman]

I have many but two stand out. 1st the first time I had make up professionally done put on my wig and I looked in the mirror. I could not believe how feminine I looked and new this was only the beginning. 2nd my wife is okay with my dressing but prefers not to see my when dressed. I had put on a french maid costume with petticoats and dark hosiery to go to a Halloween party at a LGBT friendly bar, thought I looked good and asked her if she would mind taking a picture. She said okay and when she saw me she looked me over took the picture and as I walked away to go she said nice legs. Loved that so much.

[CharlotteCD]

The first time I dressed with makeup. I had gone from a man in a dress to a passable at a glance lady with a makeup bag of tricks and my first wig.

Oh how special I felt at that moment, and how truly at home.

[HollyGreene]

Many years ago I had a girlfriend who was accepting of my being a CD to the point of us buying sets of sexy underwear together, and then wearing it while having sex.
Rather than putting up with it, she actively encouraged it by offering some of her own panties for me to wear.
Mind you, she knew that it was a big turn on for me and benefitted from my state of arousal.
All the same, it brought us very close together, which is why it's such a fond memory for me.
Sadly that relationship came to an end for totally unrelated reasons.

Oddly enough, she contacted me out of the blue on Facebook just a few weeks ago, which was very strange as it is 30 years since we last had any contact.

[Stephanie47]

Definitely the first time I ventured out on Halloween and interacted with fellow humanoids. I wore a jade and black long sleeve floral print dress, black hosiery, black heels, all the proper undergarments; blond curly wig, full makeup, nail polish. I felt great. I was also in my mid thirties, so I still had some youthful look to my face and had not added some pounds. I got compliments. Forty years later I'd do better as an old haggard witch.

[JennasPanties]

It has to be the first time I got waxed. Immediately ran home so I could change in to the outfit I had already picked out before I left. Thigh high stockings, cute mini skirt, corset. I have never felt as pretty and sexy before. Love the thought

[Bruce64]

I am of a Panty wearer, one time I bought a Warner Panty, it had the perfect nylon and spandex material, I always keep looking for something like that.

[Katherine L.]

Oddly enough, she contacted me out of the blue on Facebook just a few weeks ago, which was very strange as it is 30 years since we last had any contact.

Maybe her memories are as fond as yours.

[phili]

The one that comes to mind as extra extra special was just a few minutes out of a day in a dress- As I got out of my car one fine day last fall to go to my ceramics class, one of my friends, another women in the class, was just ahead of me, wearing a skirt and blouse and jauntily walking to class. I skipped up along side her and we greeted each other, and chatted happily as we walked to class. There was something about our steps falling in sync, our skirts waving in time, our shared lightheartedness....I felt so at peace, and joyful, and that I had crossed over. There were no more barriers to girlhood.

The next one that pops in memory is one morning going downtown, crossing a busy street in a very cute short dress and white linen short heels. As I stepped into the street, I heard a man I didn't see calling out for everyone around- 'There goes my next girlfriend!'

[Angie G]

the day she gave my a skirt and accepted my dressing. That was 14 years ago I'm still dressing and is still accepting it. :hugs:
Angie

[Leslie Mary S]

You are a lucky person.

[Lacey New]

My fondest memory was the first time I tried on and bought a dress in a Dress Barn. The sales associate was so polite, helpful and completely non-judgmental. I was underdressed and pulling that tress on over my slip was just heavenly. My wife was away and I took advantage of the situation to shop and wear my new wardrobe every day.

[lingerieLiz]

Going shopping and to lunch with a friends mom she told me to wear a nice dress and heels. His parents were hosting a formal party and he wanted me to come as a girl. She treated me as if I was her daughter. She came into the dressing room while I tried on dresses and after we picked one out she picked out the lingerie I needed to wear under it. The store staff told me how pretty I was.

[JoanneNY]

Years ago when I had a real day job, I had to work at a exhibition in the Boston area, I boldly took from my wife's closet a red gown that I loved along with a bra, pantihose and some makeup and stashed it in my suitcase. It was the first time I had ever dressed and in a hotel away from home. Not much to add to that but it was the big, first time, and I drove home underdressed.

[Jennylace]

the first time is a magic moment it's like the first thing a wife buys you completely unexpected and is the norm from that point on.

[franlee]

The 1st time my 2nd wife and I discussed my desire to crossdress. We had been married about 3weeks. She listened to what I said and was exceptionally excepting. I had explained that I had CDed on occasion with my 1st wife and it was fun but not fulfilling and left me wanting to indulge in a more realistic presentation. She understood without any hesitation and she dressed me from the skin out as she would for church. I remember each piece of lingerie and the fillers she used then the makeup and hair. She was amazing in her abilities. I was in very good physical shape then and we were both the same height and shoe size. She dressed me in a white button-down L/S blouse under a 3 piece black with gray pinstripes suit. The suit was snug but fit and was filled out with the aid of some well-placed socks. The skirt was knee length. And black heels finished the outfit. But then the real emotional part was when she took her necklace that she always wore and placed it around my neck. We then went into the bedroom where the full-length mirror revealed the finished product. I was far better looking than I had ever been while CDed and was very near if not passable thanks to her skills and taste. She handed me a pocketbook and we went for a long drive. That was the 1st time I had ever really ventured out far from home. But with her next to me I felt like I could be her sister or best friend with no problems. Itt was a feeling I will never forget and always cherish.

[Felicia M]

There are two that really stand out.

The 1st is the very first memory I have of wearing my mother's stockings. I must have been four or five years old. I was seated at a desk in the living room by myself and I had removed all of the cushions from the sofa and stood them up on end around the outside of the desk legs so that no one in the house could see under the desk and see my legs. I remember the feeling of sheer joy. I absolutely adored wearing them, I remember my mother eventually seeing me in them somehow and helping me close the gaps in the cushions so no one else would see me. I really had no idea how blessed I was in that moment.

The 2nd time was when I became accomplished at doing makeup and saw Felicia for the first time. This was only in the last couple of years and I had worked so hard to get better for a few months. I remember finishing up and looking in the mirror and having my breath taken away. I felt much like that younger self when I put on the stockings. Just a complete sense of sheer joy and happiness. It also changed me within forever. ❤️

FM

[DTelia]

Heres one....

Ive shared many times that I dont dress much...didnt dress for the first time in my life until 10 years after marriage. My wife knew from the beginning, but we just never tried it, even though she knew I wanted to. She isn’t great at gift giving or surprises...just not her thing.

Anyway, about 18 years into our marriage she planned a weekend getaway, and had made all necessary purchases to complete the look. She knew what I liked, what I wanted, and surprised me. It’s the only time shes done that. Our drive to the location was a good five hours away, and I could tell something was up, because she was so excited by something. It was a great trip. Since then she has encouraged me to dress more...it did pick up to maybe 10 times a year but has settled down again.

Maybe she’ll surprise me again ;-)

Ultimately, she does it, because she wants me to be happy and she knows that I care more about her happiness than I do about mine.

[CDJamie2000]

Went to my friend's house where I changed into Jamie wearing my new blouse and skirt. He drove us to Biloxi and went to a couple of the casinos At one of them we had lunch(I was still Jamie) and I was a little nervous but the staff there treated me well. Enjoyed the lunch and then went to the mall and and a park and finally to our motel room. This was the first time I spent the entire day as Jamie and I enjoyed it. Of course I did love wearing the new outfit. I was now confident going out in public dressed as a woman.

[rian]

my favorite memory was when i completed confession of my crossdressing to my wife ,,,,then she asked if she can see me wearing some in front of her ,,,,i then wore my favorite lingerie outfit with a baby doll as a crown and high heels .... had a small walk infront of her ...she giggled and had the most beautiful sex that night ...

[Audrey34]

I've had many magical experiences dressing up. One of my faves was when I joined my support group, Pathways for the first time back in 2007. Still remember the thrill of walking fully dressed into the meeting room and getting a round of applause and many shouts of "welcome" as I was introduced to the group. Was such a lovely moment and I'll never forget it.

[Christina89]

I dont have a great memory for going out for the first time or doing things like make-up for the first time. It was mostly when I told my mother the truth. Yeah she didn't appreciate it. But truly it felt like a weight of lying was off my shoulders. I do have a plan come November for something else that will be memorable for me. But till then its a fantasy.

[Beverley Sims]

One time that stands out was Saturday morning dress shopping for something to wear that evening.

My girlfriends had just found a new girlfriend in me and they wanted me to look sharp.

Yep! A great weekend. :-)

[oh to be rachel]

if this was Facebook that story would definitely get a :thumbsup: or a heart!

[Natasha.k]

Going out En femme for the first time with my girlfriend as BFF. It was an amazing day. We had a great time.

[TillyCambiare]

Its heartwarming how many of these moments involve SOs

Tilly

[Katherine L.]

Its heartwarming how many of these moments involve SOs

So true!

[alwayshave]

When I had my makeover at True Colors, looking in the mirror was so mind blowing. I think about it all the time.

[sometimes_miss]

Freshman summer, not quite 15, still pre pubescent. But fit perfectly in my sister's clothes. Everyone else at work, so I spent the day dressed up in her things, trying make up, reading her magazines, and of course, already having long, pretty hair, could easily have passed. I remember that day as if it were yesterday, though it was half a century ago. Took a long time to acquire a look-a-like dress to that one, which that fit me as an adult.

[Maria 60]

As much as I did enjoy the first time wearing a slip and pantyhose in front of my wife but I seem to have another memory that sticks more. It was Halloween and my wife and in-laws and a few of there friends dressed up and we went house hopping. At one house of my inlaws freind we were leaving and I was waiting at the front door when the friend came up to me and told me how good I looked as a women. He then complemented my legs and lifted my dress exposing my panties and he reached down to my ankle and felt my leg all the way up. I didn't stop him from doing anything, I just stood there and let him touch me. Afterwards my wife told me she seen what happened from a distance and asked me if I enjoyed it. I told her it was something new and that I never had a man touch my pantyhose legs ever. I never told her but I felt that feeling for days later. I guess it was just like a feeling that I could pass one day.

[abby054]

I went to an Oktoberfest in a complete dirndl outfit two years ago. I had a wonderful time, so great that I repeated it last year, enjoying it just as much. I describe my adventure at https://www.crossdressers.com/forums/showthread.php?260502-Oktoberfest&highlight=Oktoberfest . I include a link to my photo in the same thread.

[Sometimes Steffi]

My fondest memory was the first time I tried on and bought a dress in a Dress Barn. The sales associate was so polite, helpful and completely non-judgmental. I was underdressed and pulling that tress on over my slip was just heavenly. My wife was away and I took advantage of the situation to shop and wear my new wardrobe every day.

I'm so glad that you found a time to go to DressBarn and get the full treatment. How I miss DressBarn.

[suzanne]

My best memory goes back to the first time i set foot in what is now my absolute favorite dress shop. I gathered up the courage and forced myself to walk in, armed only with my ATM card and my opening request. When the first SA (she actually turned out to be the store manager) asked "Can I help you?" I answered with my prepared line "Do you have any dresses in size 20?"

"Oh!" she said in a way that told me she knew right away I was shopping for myself, "They're in that corner over there. Just let me know when you want me to open a fitting room for you." I thanked her and went to pick out a few dresses to try on. After a few tries I found two dresses that looked nice on me, and I took them to the register.

Thus began my love affair with that store, where I met and made friends with the most wonderful sales staff who truly cares that I look good in my choices and love how it feels to be beautiful. Its a gift that keeps on giving. BTW, I am also a regular in a few other plus size dress shops in my area, where many of the staff know me by my nale name. The problem is only that not as many of their offerings works as well on me.