Happy memories...

[Nichola]

Lets hear some of your happiest memories as a crossdresser.
Anything you like, whether it be the first time you dressed, an outing, or maybe an interaction or moment of acceptance.

Whatever really, whether you're in the closet, out & about or have transitioned. No matter how big or small, just those things you'll never forget. The things you can look back on that make you smile.

What will stay with you that you'll remember fondly for the rest of your days?

[Gypsy Sam]

Rediscovering the urge to cross dress in my late 20's are my happiest memories crossdressing. Dabbling with Mom's things in the puberty without getting discovered was my orientation. When living on my own and having a girl friend who lived with her parents , leaving articles of clothing behind for a variety of reasons gave opportunity to dress when left alone. The image reflected in the mirror while dressed stirred the imagination and became the hobby I turn to for enjoyment and on-line friendship. Juliet Prowse was a favorite back then, and trying to imitate her look was a very happy time.

[Beverley Sims]

The time when I was 20 and I was asked to drive 4 girls to a beach shack 50 miles away.
I was expected to leave them and pick them up the following week.
We arrived late at night and I stayed over. With neighbors that knew a couple of the girls I could not stay as I was not supposed to stay.
I was kept under cover and as they knew of my dressing ability I was invited to stay.
We got away with it for a whole week and I had to cancel engagements back in the city to stay there.
There were five girls that stayed a whole week and when the parents questioned who the fifth girl was it was revealed that she was a local friend.
Indeed.

[AndreaS]

For me, it would be the time that I got my first makeover and then went shopping. I enjoyed the makeover that this very friendly lady does at her home, but it was the shopping experience after that really floored me. After the makeover, I felt more confident to venture out to the mall and see if I could pass well enough to do some shopping. When I got there, it was a little unnerving to get out of the car and take those first few steps inside. Even though I was very nervous, I noticed that no one around me gave me a second glance at all. I couldn't believe that I was walking around in a crowded mall totally enfemme and I was treated just as another random female shopper. It was such a liberating experience and one that I used to help build my confidence to go other places and do other things (I've since flown pretty among other things).

It took me a while to build up my own makeup skills to get back to that same level as the makeover, but at at least I knew it was possible. I'd highly recommend for girls that are "on the fence" to go get that makeover and see what's possible with respect to your feminine look.

And as for you, Nichola, you have no excuse not to get out there and enjoy yourself totally enfemme. I always enjoy seeing your pics and think your sense of style is excellent.

[Cheryl T]

Mine would be just after I came out to my wife.
She was going to her company Xmas party and I was going to fully dress for her for the first time and be waiting there when she arrived home.
I was so nervous as I got ready...full body shave, hands shaking as I did my makeup, knees quaking as I sat there waiting for her to get home, near heart attack as she came up the stairs hoping she wouldn't make fun of me, laugh or just run away.

She didn't do any of those and she complimented me on my appearance as she "inspected" the lady in front of her. We talked and talked for hours and it was so wonderful to finally have someone to share my secret self with.

[kimdl93]

For me, it was spending Christmas and New Years Eve with my wife, en femme. I am dressed pretty much every day, when I'm home, but most of our holidays are spent with family members who don't know. But this year, we spent the holidays largely by ourselves, so we made the best of it. It was really wonderful to spend Christmas Eve, for example, preparing our meal together, sipping wine by our fireplace, then after dinner, opening each others gifts while kneeling by the tree. It was a remarkable experience...and the greatest gift we chould share.

[StaceyJane]

For me the best moment was when I found a letter my daughter had written to me telling me she knew about Stacey and encouraged me to be happy. It was a shock but the acceptance meant so much to me.
As far as crossdressing adventures go, there is the time I took the tour of Cowboy's Stadium en femme. I even have a picture of me standing on the star in the middle of the field.

[JenniferR771]

I loved my makeover at MAC and...the shopping afterwards. So nervous, but so fun, and fulfilling! I stopped at the mall salon--the girls offered to give me a haircut--I declined as I was wearing a synthetic wig.

[Jocelyn Quivers]

1. When I came out of the closet to my wife while were still dating and she accepted it, and did not brake up with me.
2. The first night I actually dressed completely as "Jocelyn" in front of my wife and fixed her dinner and we had a very romantic evening. Amazing how over time she and I take for granted me being in girl mode and it's become more of the routine now.
3. The first night I actually accepted I am a crossdresser and finally quit trying to be all male. Brought tears to my eyes.
4. The first person I actually told (family member) I was a crossdresser and her response was "that's it?" "I thought you were going to tell me your dying! What a relief! Of course I'll take you shopping!"
5. My first laser treatment. Good Grief that hurt, was painful, had me in tears, and I almost considered telling the tech to stop and forget it, luckily I stuck through it, including the several weeks of blisters which occured after.
6. The first time I had lost enough wait to actually fit in my Hooter's Girl Uniform with splitting the pantyhose.
7. My first pics in which I actually considered myself as attractive.
8. My first trip to an endocrinologist and getting approval for HRT. (Currently on hold for the time being, a very long story as to why)
9. First time I shaved my legs completely, followed by everywhere else.

Most important thing- Somehow stumbling across this forum it was the biggest influence in helping all of the above to take place.

[UNDERDRESSER]

I think it's one of two incidents. The first was when i told my GF, who was not my GF at the time, but I really wanted her, and i knew i couldn't NOT tell her. Her reaction? "OH Cool!" and then we carried on our conversation, with the added aspect of underwear choices...surreal at the time, but such a relief! The second was after we hooked up, and I came over to stay the night, went into the bedroom, changed into a skirt and stockings, male clothes otherwise, and came in and sat down by her. She slid her foot up my leg, under the skirt, smiled at me,.....and carried on reading her book. She just lets me be myself, she is a treasure beyond price.

[Christinedreamer]

My wedding night in 1975. I kept complimenting my wife on how beautiful she was and her incredible long hair and how it looked so good with her snow white beautiful bridal peignoir. After a while, she just looked at me and asked "Do you want to wear this?" I stammered a bit and said "yes I do". That was the start of a beautiful but all too short marriage (NOT due to CDing). She loved my dressing so much she wanted me in square dance dresses with soft petticoats and peignoirs all the time . She also wanted us to have matching outfits, We did, too. Several.

[carhill2mn]

I have many happy memories related to my crossdressing. There is one that makes me smile when I think about it. It happened one night in December. I had just attended a meeting of fellow trans psople and as I was walking toward my car I could hear my heels clicking on the sidewalk and feel the breeze blow my skirt. For some reason this experience has really stuck with me.

[Kelley]

I have quite few memorable moments. I think the best so far is when I bought my most recent wig. The lady who owns the shop I went to does wigs for a lot of the TG community in Atlanta. It was a wonderful experience and the wig made such a profound difference in my presentation and confidence. It's the one in my avatar.

[Rachael Jones]

Some wonderful memories for me:

Realising that cross-dressing gave me a massive boost in self-esteem. Although hidden (at the moment), I feel at home when dressed up.
The first time I bought hold-up stockings, used veet on my legs and put the stockings on.
First time I shaved my legs. They itched like crazy when I let them grow back afterwards, but I loved the look at the time.

[AllieSF]

I get out a lot and have so many great adventures that it is hard to pick the best ones. That being said, I would say it would be those little moments during or right after a very successful and fun evening out, when I ask whomever I am with, or myself if alone, "Can you believe we are doing this?".

[Lorileah]

First photo shoot
First dinner dressed (after photo shoot)
More recently

First time being taken to dinner and a movie
First time having someone ask me out without ulterior motives
Performing (singing) in front of a crowd who had not heard me before and watching their faces when the voice didn't match the image (and they realized I wasn't going to lipsync)- and later (weeks) meeting Frankie Avalon at the same venue

[michellecd9999]

My first makeover and photo shoot with Phoebe and a more recent makeover and photo shoot and I got to spend the night en fem at Phoebe's!

[ArleneRaquel]

My most recent happy moment was a recent outing where I was wearing my new tortoiseshell female cat's eye frames with my faux fur, heels, a relatively new dress, a perfect makeup. I felt that I looked so godd & attractive. Thank you for stsrting the thread darlin. Hugs & Kisses@Nichola !

[Rita58]

I will always remember my first outing, and having my wife join me. It was a cool fall day, perfect for dressing. We went to a nearby town, where it was unlikely we'd run into anyone we knew. The day had a magical quality about it, and even though I still get a similar thrill when I go out, it's not like that first time.

[Frédérique]

Lets hear some of your happiest memories as a crossdresser. What will stay with you that you'll remember fondly for the rest of your days?

I’ve written about my happy memories at length in the “Writer’s” section. I’d write about them at length in this section, but a lot of people hate having to read long things. I think it’s a traumatic flashback of some sort, like having to read required books during summer vacation, or doing homework. In any event, my happy crossdressing memories do NOT constitute a short story…

[Leah Lynn]

It's a tie. First was my first Girls' Night Out! The most liberating night of my life! Second, was the second GNO, when a new girl joined us.

Leah

[Carrie R]

I haven't done a whole lot, but I remember the first time I went into a chat room and appeared on cam, and so many private messages appeared that they went off the bottom of the screen. Sure, many were creeps that I didn't care to talk to and had to block.

[Emma Beth]

I have a couple to share.

The first one is when I was in the Navy. One of my best friends was getting Married and he made me the Best Man. It was my duty to plan the Bachelor Party. My girl friend at the time was a Kamikaze Girl at local strip club. She suggested that I do something dressed as a woman as the party gag. We ended up getting with the owner of the club, who paid for my costuming at a Hollywood special effects shop and we had prosthetic parts made that would make me look just like a woman, even while nude. She then paid for all the extra shopping to put the rest of my costume together. As we had a few months to prepare for the party, she even arranged for the dancers to teach me to put on a show on stage. Everyone loved the idea so much, it was hard for me and my girlfriend to get much time to ourselves, but we were having the time of our lives. On the night of the party, I did my show and made a good bit of extra money from the show itself. The real moment of the gag was when I came off the stage and did just one lap dance for the groom. At the end of the dance, I leaned in to speak into his ear and in my natural voice I said, "Gotcha." Suffice it to say, I was left standing there while he and the chair fell over. I stayed in costume the rest of the night as it was far too much trouble to get into to do otherwise. It was a lot of fun.

The second was coming out to my wife, being accepted by her, and getting back into cross dressing after so many years of repressing the urge to dress with small moments of almost getting caught by her with one of her bras on.

[BillieJoEllen]

Years ago I dressed to the nines and went out. It was probably the best I have ever looked. I felt so scrumptious and femmy that night. I had my makeup on almost perfectly, I had on just the right amount of scent. Went through a couple of drive-throughs that evening and no one batted an eye and treated me with respect. I was floating far above cloud nine. After I got home I poured myself a glass of sherry and turned on MTV. Fell asleep. I awoke to a Gloria Estefan song and to me life was never better than at that moment.

[Nichola]

Thanks for the responses, all nice to read. A lovely insight into what makes us tick on a personal level
As for me, despite the ups & downs of crossdressing, I have some nice memories too.

When I was at school around 14 to 15 years old, quite often I'd go home for lunch. If the house was empty, I'd take full advantage to get girly. I'd tie my school shirt round my midrift, slip into my sisters old school skirt & tights, style my hair a little girly, then put on a little eyeliner & lipstick. I know it sounds silly, but in my mind, just for those short times I got to be a girl.

Another nice memory was when I was around 17 or 18, my parents went away on holiday with my brother, leaving me home alone. By this time my sister had gone to university, but she'd left bags of her old clothing behind & even makeup. I had everything I could wish for & it was the first time I dressed fully. I'll never forget it, I'd been waiting for that day since I was six years old.
In more recent times, just actually getting through the door dressed a couple of times, is something that just felt amazing to me & left me longing for more. All happy memories for me that I'll never forget