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?
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.
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.
Work on your elegance,
and beauty will follow.
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.
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.
I don't wear women's clothes, I wear MY clothes !
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.
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.
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.
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
Be nice; It don't cost nothing.
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.
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.
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.
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
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