A good crossdressing memory of mine

[LisaJ1]

I still remember a good crossdressing memory of mine,went to the prom as a girl my senior year of high school.Started with a dare by a couple friends of mine handing me $100.00 if nothing went wrong.The principal told me I would of been escorted out if I was caught doing this and figured out to not that happen myself.It worked and never got caught.A good friend of my mom's did my hair and make up including my nails.I wore a nice pink dress with a pair of wedges making through it.Principal looked a few times and walked away.I thought I was going to get caught and did not,.Great thing was I made it through and got the $100.00.Principal and I did not get along a few times,said I probally got away with it.He does not know it was me that night and won't tell him this to this day.Told this to my fiancé Alexandra 5 weeks ago and she thought it was cool I did this.Shown her a coupe pictures and said I looked great in that pink dress.

[Sarah Doepner]

I can understand how that would be a great memory. Nothing quite that good for me but I do have a few.

Possibly the best was after my wife became aware of my crossdressing and she had done her research she came to me and said "You should take your things out of that gym bag in the basement and hang them in the closet."

[bridget thronton]

Sounds like quite an interesting memory

[ChristinaK]

Sounds like your prom was a lot more fun than mine! Something that can never be taken away from you, cool.

Took an amazing amount of courage too! Fantastic. How long ago was it?

[Tabitha_Sinn]

Lisa, I don't really want to take this off topic from your good memory, but I'll share the funniest crossdressing memory I have with you ( and actually a *good* memory).

When I was 18 and had just started crossdressing, I was over at my girlfriends house, in her bedroom with me, her and a gay male we both knew. I hadn't come out to anyone at that time except for my girlfriend and some other gay males we knew. Her Mom knocked on the bedroom door, and out of panic ( being fully dressed, makeup on, etc), I quickly rushed into the closet ( ha! No pun intended) and the gay male that was with us, jumped into the closet with me. LOL! He was the first male that ever kissed me while dressed ( in the closet!)

There's no more literal definition of being 'in the closet' than that!

[LisaJ1]

Sounds like your prom was a lot more fun than mine! Something that can never be taken away from you, cool.

Took an amazing amount of courage too! Fantastic. How long ago was it?

In 1997,it will be 20 years next year

[shayleetv]

My best memory was the summer just before my 12th birthday. I think I was too stupid to be cautious so I got dressed in a summer frock of my sisters and went down town and bought some shoes because the old ones were getting to small. I was a growing so fast it was incredible. When school let out for the summer(1953) I was 5'6" and by September I broke 6 feet. My sister was well developed and I had one of her bras on and padded with nylons to fill her cups. By the time I was all set I looked like a 15 year old girl. The salesman was a guy in his fifties and he kept looking up my skirt as he put the shoes on me. He had no clue I wasn't a real girl, after all nobody would suspect a cross dresser back then. I left home before my parents got home from work and they went to a professional organization dinner so I arrived home after they left. What a fun afternoon. I came home with three pair of shoes.

[daviolin]

Would love to see the picture of your prom. You go girl. Daviolin

[Desiree2bababe]

So lucky to have that memory, it remains an unfilled fantasy of mine to be a prom girl, that would have been so much fun.

[Petra1]

You've lived the dream of so many. Were you already dressing at that point was this the instigation to dress?

[lingerieLiz]

Shaylee, I can relate that back in the 50s so few of us ever ventured out. After high school I moved to the city. Back then cruising the drive-ins were the thing. Got to talking with a new friend who joked about going to one of the beach movies. Couples got in free if they were dressed like the actors. He said he would be the guy and I could go as Sandra Dee. Kept pushing it and I said sure, thinking he would back off. Things got crazy with the dares. My landlady knew about me and agreed to do a wig for me. I already had the clothes. He showed to pick me up came in and couldn't believe what I looked like. Sundress with petticoats, blond wig. Went to the movie and dance. It really blew him away that I could dance backwards like a girl. We remained friends and went out as a couple often, but we kept it platonic he liked guys and I liked girls.

[Dianna_ericka]

I really like the stories posted here.
I never have the courage to try going out dressed, maybe the main thing is the fear to be punished by a bunch of gangsters and the fair of be discovered by somebody from my job, which consecuences would be very bad for me and my family. My children do not know about Dianna and is also part of the reasons.
The idea of being in a public place like a restaurant or a Mall is in my buket list, maybe i will try while retired in a far away city, but I recognize the brave hart for your adventures.
Regards,

[Dora]

The best crossdressing memory I had was when after my sisters wedding she brought over all the bridesmaid dresses to my parents house after she got married and then everyone went on vacation, I was home alone for a whole week watching my parents house and trying on the bridesmaid dresses.