I'm curious if a life long cross dressing habit was started at Halloween for some? The first public outing perhaps in feminine finery and a chance to bring together clothing, makeup, shoes, ratings,...
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I'm curious if a life long cross dressing habit was started at Halloween for some? The first public outing perhaps in feminine finery and a chance to bring together clothing, makeup, shoes, ratings,...
Like many on here I have worn many ladies clothes in such situations whenever the opportunity presented itself. I probably still would, depending on the clothing. I never worried much about dresses...
I joined a video conference call with my financial planner on a link that she sent. She is a lovely lady whom I have known for years. I didn't realize that the default setting of the camera was on...
I've dressed up as a woman and went out to parties at Halloween lots of times. Many of these times in the company of people who don't know that I'm a cross dresser and that I have no intentions of...
I have come out to lots of women but have never ever admitted to a man that I'm a crossdresser. It's easier and more fun. You can talk about lipstick and shoes!
Is it just me or do any of you other girls out there love dressing up in a Wonder Woman costume? Any good stories?
My Mom used to drop me at my Aunt's house during holidays. My Aunt worked at a department store in the cosmetics department. Every day she wore dresses, pantyhose, heels and make-up. I think that...
What a great idea! Mrs Maisel's outfits are so fantastic! She has the best collection of clothes ever!
My realtor saw me dressed up before. I made an excuse that I was practising for a fancy dress party. I don't think she believed me as she just emailed me to invite me to her Halloween party and said...
Dressing up is still a big thrill for me. I also really enjoy when female sales assistants suspect that I'm buying clothes and make up for myself while shopping in drab. That's fun and always makes...
Halloween. I was as convincing as possible and loved it when girls made comments about me enjoying it too much or looking like I had some experience with dressing up!
When I was a student, I lived in an apparent above a lady who worked at the college. One day I passed her in the parking lot and she said "You know that I can hear you walking around upstairs when...
I don'r think of my dressing up as being a fetish thing except when I get the urge to wear certain outfits. If i'm at an airport and see cabin crew in their smart uniforms with tight skirts,...
Make it their idea for you to get dressed up for some reason. I once said to a girlfriend "I wonder what i'd look like as a girl" when Wong Foo was on tv (not by accident). An hour later I was all...
True story Diane. I was trying so hard to back on halloween the next year but she had plans. She did wink at me and say "and don't think I don't know why you want to come back this year!"
The question that i'm asking myself nos is if I had stuck to the fancy dress for a dare story would she have believed me? Or would she have pretended to believe me but know fine that I was a...
Yes I did enjoy outing myself. I don't do it often but when the circumstances are right its a thrill. This time it wasn't planned, the planets just aligned. I was honestly going to stick with the...
Thats a good question. I'd like to be dressed up in her company again for sure. I wouldn't want her to tell everyone that she knows that i'm a crossdresser. I doubt that she knows anyone that I know...
Fair enough. It felt a bit like being busted though because it wasnt my plan to out myself as a crossdresser to the realtor. It was a spur of the moment thing.
How fantastic! I got started when I was staying at an aunties house at Haloween as a 14 year old and my aunt and female cousin (2 years older) crossdressed me. The whole shebang - panties the lot....
At halloween i dressed up as Harley Quinn. I was getting complements on my makeup and legs from a young lady who asked me why i chose that costume. I told her that I really just wanted to wear the...
Yes I was wearing wig, makeup, jewellry, painted nails the lot. I knew that when I agreed that she could stop by that she would know that my costume was more than just fancy dress. It gave me a bit...
Thats so cool! I love leaving size 13 heels around when I know that ladies are coming to the house to see if they say anything. I figure that if they don't say anything, they know that they are mines!
Live in GF was asleep one night and I went into bathroom and put on all clothes that she was wearing that evening. Tight black dress, lingerie, heels. Then i put on her makeup and hung out for an...
Yesterday I was all dolled up and I took a phone call from my realtor. I thought that it would be fun to be dressed up as Caitlyn and my realtor would have no idea that the guy she was talking to on...