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My First Time I Crossed Dressed

The first time I crossed dressed I was 14 and it was for a costume party at church. There were 5 of us kids and money was tight. My mom said I would be going as a girl. First she had me put on a pair of her panties then one of her bras and stuffed it with kleenexes. I remember the panties and bra felt really good on my body. Then she had me put a pair of panty hose which also felt really good. I was a bit taller than her and about the same size she had me put on one of her dresses. I liked it too. Then we proceeded to put on make up. The rouge, eye shadow, eye liner, and best of all red lipstick. She did do some plucking on my eyebrows to give them a more female look. We used a new cloth mop head for my hair and one of her hats for my head to hid the seam in the mop head. As if that wasn't enough I wore a pair of shoes with 4 inch heels. Then for the next hour and a half I was parading around the house learning to walk in heels and like a lady. I also had to sit like a lady. I also wore white gloves. I had a complete feeling of satisfaction at that time. Now I know It was a turn-on for me. I was the first of the kids to get dressed. I don't remember how they were dressed. We all got into the car and went to the party. They went in first and I would come in later. As I came in people were asking "who is that" trying to figure out who I was. As they did I walked like a female and like I had worn heels for years. I went to an empty chair slid my hand down my butt and the back of my thighs as I sat in the chair and crossed my legs lady like and gave little flip to my dress to put it on top of my legs. Boy those hose felt good as my legs were crossed. Well they were able to guess who everyone was except the young lady who arrived alone. ME. So finally they gave up. I removed the hat and the hair and put my glasses on which mom had. They could not believe it was me. Some of them said I was a pretty girl.The rest of the evening we played games all this I was still dressed as a lady. All total I was a woman for about seven hours and loved it. Over the years from time to time I put on my wife's clothes for a little while she is out and still love it. I have my own bras now since I have developed breasts. I also do theather acting and one dream is to have a part as a male dressed as a woman so I can parade around in front of hundreds of people dressed as a woman.
What do you think?
Adam59 Adam59 56-60, M 14 Responses Feb 12, 2012

Your Response


I think you should do a production of Charlie's Aunt.

In a few months you will have an annual chance to crossdress & get away with it, even with a wife. I'm speaking of going to a LIVE Rocky Horror Show (or many RHS's) NOT the Movie but a real Play. Crossdressing is VERY welcome and women will at worst tolerate it and at best take you back home and roll around in bed all night. Read some of my stories and look at the photos of my 2/3rds of a Century Party last Oct. My Avitar is from that party. So just start getting your "Stuff" together and tell her you might need a little "help" and see what happens. I have a female friend (wife of a good friend) that loves to take me shopping and both of them are regulars with me at the shows (he's the Pimp in the purple hat on some photos with us). So let me know how it turns out, I think you will have a ball. TTFN
PS: You can find locations across the country & overseas of upcoming RHS by Goggleing it . Let me know if you need help.

If only she knew how much it meant to you! Dressing you up like that was just the start to your life!

Go for it!

Dreams sometimes do come true, Adam, and my wish for you it that you get a part as a male dressed as a woman.

Me too.

I think I hope you get your wish, Theater is fun, I've done a could of plays. Like you I was hoping for a female part. I even kept after my director to find out if he was going to do La Cage. That didn't happen before got into other things. Be well!

Thank you.

Do you remember what panties you received from mum? What appearance they have?

Plain white cotton panties

What an introduction to dressing and femininity. You so had to love those seven hours and it's clear that you did. I wish my mom had insisted that I dress as a girl rather than just suggesting that I do so, affording me the opportunity to say no when I wanted to scream yessss!

Yes and I wanted it more often.

Great story, my mum never dressed me up. I started much earlier, about 8 or 9. By the time I was 14 I was already trying to buy or steal(!) my own clothes. I did ask to be dressed up as a girl for carnivals, but mum said don't be silly. Sometimes I hoped I would be forced to wear girls clothes for the carnival and did often have wet dreams about it. <br />
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I was mistaken often though, as a girl that is! I sk t know why, it happened a few times. I was quite shy and immature for my age and maybe a bit effeminate. I even got put in a group of girls at a sport camp, which was great. I had a tight pair of running shorts on that were pink, they werent womans, just been acidently dyied in the wash. I did have not much of a willy at that age and also had my willy tucked underneth me, so must have looked quite fem and flat! I had a whole afternoon being a 'girl' no one knew any different. I was very strange, liberating and scary!

You go gurl. If you got it flaunt it.

I plan too.

I think you have had thrilling experiences.

Oh I have. It's even better now that my wife knows. I dress everyday at home. I even wear nighties to sleep in. When I'm at home I'm dressed as a girl all the time. It's great

Your very lucky. Enjoy it for all its worth.

You're lucky. My wife gave up on sex, also, years ago. However she barely tolerates my unisex clothing. I shudder to think what she would say if I tried staying dressed all day.

I have always wanted to dress up. I remember Halloween once when I was young and asked to dress up as a girl but for some reason did not let my mom or sister do alot of make up but I do remember asking to wear pantyhose under the dress. I have always had a fetish for pantyhose.

It's already been done. There will be others and I'll wait and hope. There are quite a few out there.

i think it would be a thrill .....try "charlies aunt" or a stage version of "some like it hot" you could be in womens clothes and tony curtis !!! haha just have a good time hon