Your top five CD moments

[Lea]

David Letterman has his top ten. So lets starts a top five list of the best CD moments in your life.

For me the top five are:

1: After I told my future wife of my crossdressing she brought over an outfit and makeup to my house. I dressed she did my makeup and we spent the evening together.

2. After we were married she gave me a wedding ring with three connected circles. She told me the circles represent us. Her and my male and female side.

3. When we went out of town for Halloween dressed alike. To enjoy being able to go out together dressed was wonderful.

4. When she brings me flowers when I am home dressed. I do this for her and she started returning the favor.

5. Except for Halloween I do not go out but when I dress my style is business attire. Skirts, dresses heels etc. One time while dressing for a five day stretch we put new flooring in, painted the room etc.. It was enjoyable to be in the proper undergarments, still wear my nails, and wear blue jeans and a t shirt while working in the room. Working together was enjoyable.

[DonnaT]

Don't know if I have a top 5. Hmm,:thinking: in no particular order:

Finding some old clothes of my Mom's while cleaning out the basement, trying them on, and the journey began.

My wife shaving my legs because they itched her in bed. Newlyweds. Then daring me to wear pantyhose over my newly shaved legs, which led to her giving me a dress to try on, and then an old wig and makeup of hers.

My wife telling me how pretty I looked the first time I was fully dressed.

The first time my wife and I went out together. This led to more times out.

My wife's current acceptance, knowing this is a part of me that won't go away, and, wanting me to be happy, being open to my dressing at home whenever I desire.

[lynnef]

Hmm, top 5?


not sure I have 5... but here goes (un-ordered) :)


Being at a halloween party and several GGs coming up on their own to talk with me (*never* happens in guymode)

an Ex-girlfriend telling me how the pictures she'd seen were no comparison to real life (she's also the one I picked my femme name from, with her permission)


One time when I dressed up for work on halloween, a male co-worker (who was/is rather conservative), said he was amazed how well the dress fit me :)

When I told my mom and she was accepting (not embracing, but better than expected :)

wow... These are harder than I thought... :| (maybe because there's so few for me)

last one....

Doing a resident's nails during clinicals and no one believing i'd done 'em (except those who saw me :)

[JerseyGirlDonna]

Let me think.... Again, no particular order:
My first MAC makeover
The time a man in Kohl's called me sexy (he could have been senile or blind, but it felt good anyway).:o
Discovering this site, knowing I'm not alone
Having lunch out with a friend I met through this site
My glamour photo shoot

[Miss Trudy]

Boy this a toughie, picking only 5! Let me see ...

5. Discovering an old friend who is not only a good friend but also that special guy for me

4. Actually meeting another girl face to face and having a lovely lunch discussing what is it like to be "different."

3. Going out in the world as Trudy and finding out that at least some people were nice and accepting of us girls.

2. Discovering I was not the only one in the world who had this "hobby."

And last but not least (drum roll please)

1. Having my mother and sister accept me as Trudy. At first not truly welcoming but that has grown to total acceptance over time.

[BLUE ORCHID]

Hi Lea, :daydreaming:I don't know the top about 5. , But here are 5.:daydreaming:

1. Dressing for 67yrs.
2. Wearing Hi-Heels
3. Wearing a Wig
4. Wearing a Bra & Forms
5. Wearing Pantyhose

[Confucius]

Just to go through them chronologically:
- When I was 4 years old I used to rummage through my mom's closet and play dress-up. She couldn't stop me, so she made me a dress of my own. Initially I was thrilled, until my older brother teased me mercilessly. It was a form of aversion therapy. The dress was then given to a neighbor.

- When I was 12 years old my mother was making some room in her closet and moved some of her old vintage dresses into my closet.

- When I was 14 my school held a womanless beauty pageant. I was NOT a contestant but the whole thing was thrilling to me anyway.

- My first job after college was in an office where I was the only man. The women in the office decided to celebrate Halloween with costumes and they all encouraged me to come to work dressed as a woman.

- The first time I talked to my wife about cross-dressing and she was against it, but later allowed for some limited cross-dressing. She sets the boundaries, but she is a great person.

[RenneB]

Great topic. Here's my five....

1. Finding this site and then the awesome feeling that I was not the only one in the world born like this.

2. Meeting up with a group of other girls at a bar and as I walked to get a drink for the first time, overhearing one of them saying "she's one of us".

3. Ground Hog day prom. Look it up. Totally wild.

4. Four of us girls going to a restaurant for a late night snack. Me dressed as a prom queen, one dressed up in Star Trek outfit, another in a piece of cake costume and the fourth dressed in a full bloomer wedding dress. Yea, it was a wild night.

5. Having a GG lady at the thrift store turn to me while we were looking at dresses and say "this would look great on you hun"....

Renne.....

[Roxie]

1:Knowing I can now dress as much as I want

2:would have to be when my former girlfriend daughter had a talk on how she like to dress as a man ,and me a women .what a relief to have someone to talk to and still do
3: finding woman panties that not only fit ,but were comfortable ALL DAY
4:finding my love for bras
5: buying my first dress that fit

[AKADonna]

5. Being forced to dress up for the first time by a BDSM Mistress

4. Buying my first bra, forms and panties

3. Having 'the talk' with my wife and getting an acceptance (not supportive, but accepting!)

2. Having my first makeover by Phoebe Cross

1. Going "out" fully en femme for a whole day to a Tri-Ess meeting and since being able to shop for female clothes without fear or angst. I feel really Feminine!!!

[Adriana Moretti]

my top 5 constantly changes,,,,,,its always fun....either out in public, or at home hiding in the closet ...I can make the best of it .but my awkwrdness in public takes the cake

[mechamoose]

While I like guys, I'm annoyed at having that be the default view just because I'm wearing a skirt & heels. I love me a pretty & confident girl.

It is one thing to be accepting of that, its another to have that be the base assumption.

I guess it is the 'role' thing... if you assume a female persona, they expect you to do the rest. Expressing ourselves as female isn't the same as being 'sub'. While I *am* that way, I get pissed off that 'they' conflate clothing choices with our interests.

- MM

[ange_o]

Dressing (albeit in costume) for a function for a club I'm in with about 50 people there.

Getting complemented on my makeup at that function.

Buying and wearing my first pair of black patent mary jane heels (half a size too small but so cute I had to have them). Also was my first time ever trying on shoes in a store.

Taking photos of myself out dressed in a park the other evening and finding several that I love how my outfits look in them and if it wasnt for the face would be quite passable.

Talking my first walk in daylight along a (sparsely populated) beach enfemme and jusy sitting down and appreciating the moment.

Hoping for more moments to top these one day.
Ange

[Beverley Sims]

My first perm.
My first mock wedding.
Being a catwalk model.
Winning a drag talent night.
Being escorted to a debutante ball.

They must rate as amongst the best five for me.

[Ressie]

1. Trying on panties - age 8
2. Trying on a dress - age 13
3. Trying on more of mom's and sister's clothes (hose, slips, wigs, bras). that was a long moment!
4. First time putting on eye liner in the bathroom, age 21
5. First time buying fem clothes (bra and panty set) at a store, age 30

[Stephanie Julianna]

After 35 years out and about 5 is not easy but I'll try.
1) Meeting Lee Brewster and having him do my first makeover that allowed me to look good enough to leave the store dressed for the first time in NYC. (1980)
2) Being dressed at Lee's and meeting Sam who thought I was a GG until Lee introduced us. That started a life long friendship with many adventures. (1981)
3) When I went to work dressed as a female RN on a dare. Until I spoke no one knew who I was. They made me a name tag that Said "Miss Diagnosed". I did win best costume but oh how I wished I could wear it every day. (1995)
4) Being the Finale model at First Event in Boston in 1999. After the show, I was allowed to wear the wedding gown back to my room escorted by Sam. Every woman we met along the way, through the busy Hotel lobby, congratulated us on our nuptial and complimented my wedding gown. No one read us as anything but as happy newlyweds.
5) Going out dressed, after years in the closet, to a lingerie shop in CT that caters to CDers. After I shopped a little and finally introduced myself the owner and SA told me that they had commented to each other that it was nice to see a GG that also appreciated their store that day. There were a few CDers there and they hoped they would not be an issue for me until they found out I was no different. (2014)

[JamieG]

It's hard enough to pick 5, let alone order them. So I'll take a crack at 5 top moments in chronological order

2002 - About a month after coming out to my wife and an ugly aftermath, our relationship began to thaw. One night before going on a trip, she threw me a pair of sheer black pantyhose and said I could have them. She asked me to put them on, and then proceeded to put me in a black dress, heels and Halloween wig. It was cathartic to finally show my her myself in drag.

2003 - My wife and I went to a friend's Halloween party as two female pop stars. She bought most of my outfit and did my makeup for me. It was my first time outside the house en femme. I was super nervous, but everyone at the party loved my costume. Some still talk about it today.

2010 - Performed in a charity drag show with my wife. Shaved my arms for the first time to get the right look. Two young girls came up after the show and told us, "You were awesome!"

2012 - Went to the Keystone conference for two days. Stayed overnight and spent ~24 hours en femme including a fantastic evening gala. This was my second time at the conference, but I didn't get to stay very long when I went in 2011.

2013 - Went to the Miss'd America pageant in Atlantic City with some friends en femme. We walked around the casino, ate dinner, saw the show, and then hit the nightclubs. Everyone treated us fabulously. I didn't want the night to end.

There's a few other great moments I could have added, but I'll play by the rules and keep it to 5.

[Christen]

Oh, OK ..
1. Having one of my best friends not clock me when I was dressed (I was 15, he thought I was my older sister)
2. First time I went for a drive dressed. Actually felt like I was going somewhere.
3. Buying a beautiful torsolette with matching briefs for me! (Lost in the great purge of '09)
4. Accepting myself for who and what I am (only happened reasonably recently)
5. Having a wonderful wife who despite all my weaknesses has said to me, 'Oh well, I'll just have to accept that my husband crossdresses.' Love her!

Christen x

[Farrah]

1. When I got my own apartment and was able to dress and leave my things out. (2000)
2. Finding out I wasn't the only one that dressed. (1997)
3. Taking drive while dress (went to drop a letter in letter off at the P.O.). 2008
4. Going out dressed for he first time (Payless, gas station, and Belk), even though it felt like a disaster (purged afterwards). 2009
5. My wife knowing about and accepting me for who I am. (2 months ago)

[AnneC]

I think my best time had a lot of moments. Due to a work situation I had an apartment away from my home and was able to dress for 30 weeks in a row. It was great but eventually I had to go back to reality. But it was great while it lasted.

[lynn.crossdresser]

Top 5, a tricky one to restrict to five but I will have a go.

1: My first pair of high heels, well not to high 3”s but made so special because not only my first pair of heels but given by my wife as a Valentines present.

2: My 50th Birthday treat from my wife, three nights away, a fully dressed evening with my wife bringing my fem clothes and with her and her doing my make up.

3: As above but also spending a whole day girly shopping together at the sales.

4: The day I accepted I like if not love cross-dressing and I finally came to terms with it.

5: Going to a New Years fancy dressed party as a lady of the night, ok I had two pairs of panties to hide my excitement.

Near misses, my first wig, trying on fem clothes in store, buying make up and oh so many more pleasurable experiences.

Lynn

[wanda66]

First time I underdressed
wearing panties to a doctor appointment.
traveling alot and being able to dress 4 or 5 days a week
the first dress I purchased
seeing myself in full make up

[Bryanne]

What a difficult list to make, but here goes:

5. First time trying on a dress, around age 7 or 8, perhaps. Loved the feeling.

4. First time fully dressed in underthings, nylons, stuffed bra and dress. Even tried my best with makeup, and stayed dressed for about four hours. Best night of my life to that point.

3. Telling my girlfriend about liking to dress, and seeing her all excited. We were around 14 years old, and this began a great relationship change.

2. Going out dressed for the first time at age 16, and being hit on by guys, and talked to be all sorts of girls. Without being too blunt, I lost my virginity that night to my girlfriend, and I've never felt sexier or more secure in who I was.

1. Rediscovering the joy of dressing after eight years of going without, and purchasing new makeup and underclothing. The girls at VS made me smile so much. It's a lot like riding a bike, only I feel much prettier!

[Renee Elise]

This will evolve over time :). As of now:

1) The first time I shaved my legs and wore nylons.
2) Completing my femme look with a beautiful wig for the first time.
3) Getting eyeliner and shadow perfect.
4) Finding peace with my femme persona and realizing how much fun it could be, and enjoying every part of getting dolled up when I can.
5) My first compliment after sharing femme pics - nothing like being called beautiful.

[Jennifer in CO]

just 5 is a toughie...

1: 1967 "becoming" Jennifer when I was 10

2: 1972 spending most of the summer I turned 15 with my grand parents - as Jennifer

3: 1975 meeting my future wife on the 1st day of college...she thought I was a girl!

4: 1976 proposing to my future wife - wearing a knit denim peasant top she made for me, linen slacks and earth shoes with a pink trousseau underneath she gave me to tell me she had no problem with me CD'ing (I flew so dressed to Denver to do so)

5: 1981 the first time my sundress stayed up because my breasts had grown large enough that they would hold it up

[Lux]

Awesome thread..

1) Sneaking out of my parent's house late night when I was 16 to walk past large storefront windows to see my reflection. This was my first time out 'in public'. I was dressed to the nines head to toe and the sound of my high heels clicking down the empty street combined with the cool evening air on my nylon encased legs was a memory never to be forgotten.

2) Same evening. I was halfway down the block when a car came down the street. Nowhere to run and hide, the car slowed down enough for me to hear my first wolf whistle and the words;"Hi beautiful". Sounds great now, but my heart was in my throat at the time!

3) After starting college, having the nerve to dress up and go into a brightly lit convenience store to buy a pack of gum. The 2 workers (a guy and girl) were blown away that I was a boy when I told them. Yes, of course I used the ol' 'doing this for a fraternity initiation, blah,blah, blah' line.

4) Recently going to Las Vegas this past spring with another fun married couple (who recently found out about my female side) who were 100% accepting. Probably one of the funnest nights of my life being able to dress in sexy clothes and high heels (Vegas baby!). It included going to the straight clubs to dance where we were invited to peoples' bottle service areas since we were dancing our booties off.

5) My biggest CD moment..easy..The pure loving acceptance and understanding of my wife with this somewhat often complicated aspect of my life. I do realize what a gift I have with her and try not to ever take her for granted.