My Crossdressing Experience

Coming out part way

I am a closet cross-dresser, 47 years old. I’ve always had an interest in cross-dressing since I was little. I first tried on my mother’s bra when I was 8, but I didn’t know how to hook the back at the time. A couple of years later I tried on pantyhose. That was really a nice feeling.

A couple of years later I was over at a friend of my mother’s house with my brother and friends, a boy and a girl. I allowed the girl to put make up on me. She then went to both her older brother and my brother and told them what she done and to take a look. They saw me and laughed hysterically! I was majorly embarrassed! Yet my desire to cross-dress remained.

As the years went on, my mom would get hand-me-downs. I would try on dresses and other clothing. I had two favorite dresses: a maroon with ruffled front and zipped in the back. The other a floral dress that had a stretch to it so that it fit different sizes. I also loved wearing a leotard with pantyhose as well.

As I grew into my adult years and living on my own, I had no women’s clothes. I went to the drug store and bought a pair of white cotton laced pantyhose. They were hard to put on and were tight.

As the years went by I started discovering that I could buy clothes off of Ebay. My first win was a blue silk pajamas complete with a tank top and button up night shirt. I loved it! Through the years I would buy and purge. I bought a lot of clothes over the years, none of which I have now.

I have also considered cross-dressing services such as My Changing Room and Jamie Austin. Money is a factor though.

I desire to make fellow cross-dressing friends both male and female to share a common bond with. I have looked at sites such as Craigslist, but they all seem to be looking for something other than friendship. My ideal situation would be to get to know someone and casually dress in their presence so that they could give me advice, help with make-up, etc.

So that is pretty much my story. I hope that you enjoyed reading it.

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Victoria-Rose

Hi, I am a 47 year old closet Crossdresser. I've been interested in Crossdressing almost all my life. I am quiet, have a sense of humor and a real lot of knowledge about music. I was born and raised in Boston where I still live now.

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Julie Carson
Lady

Victoria Rose what a wonderful story. You must feel so lberated telling it. I too am beginning to make friends like ourselves outside the home. It is truly such a feminine thing to do. Hugs. Julie carson

Ashleigh
Lady

Thanks for sharing your story. The more you read here, the more you realize how common a theme it is.
I have pretty good luck buying clothes at thrift stores such as Goodwil. You can get some really nice things reasonably priced. We have all purged to some degree at one time or another. Although, I still have the very first skirt I bought specifically for me. It doesn’t fit that well (too big smile and is no longer my style, but the nostalgia of it wont let me toss it.

Julie Carson
Lady

Oh Ashleigh a fried just turned me on to a place called Savers. She bought a $350 dress for $60

Guess where Julie is going?

janedon
Lady

I go around to all the charity shop(salvation army ect) & other used clothing stores & over time have built an impressive wardrobe–From shoes to wigs & everything in between—&–I try everything on at the stores so no need to Return things-
Jane–London Ontario

chloe
Lady

Thanks for your story. Closet here also with no desire to go public but would love to have a dress up friend. Had one experience but I am straight and she was not so didn’t work out. We have a lot in common girl.

April (Pacific Princess)
Ambassador
Member

Victoria-Rose, I think a lot of us can relate to your story. You are a little younger than me, but there was no internet in your youth either. Kind of makes you feel alone in your desires. Glad you are here on CDH. Hope you can find the friendship you’re looking for.

April

Sallysim
Member

Victoria Rose , that’s a lovely story and one I’m sure we can all relate to in one way or another. CDH is a warm friendly safe place for us all. I’m sure you will enjoy being here and meeting new friends. I’m sure you will build in confidence as I have being here. Try popping into a chat some time the girls are amazing
Hugs
Sally

Stephanie Green
Member

Victoria Rose, let me follow up the comments from Sally by saying that CDH is a marvelous safe and loving support group. The girls at this site gave me the courage to come out to my wife just recently after being closeted for 50 years. Continue to post and chat here my dear. Hopefully the many stories about the struggles of other girls will give you the confidence to move ahead with your journey as Victoria-Rose.

Hugs my dear,
Stephanie

*skippy1965(Cynthia)
Ambassador
Active Member

Victoria,

Welcome! and what a Lovely article . WE are so delighted you chose to become part of our community! AS others have noted, the chat room is a great place to get to know folks and he articles and forums are chock full of advice and tips and stories to give you inspiration and the realization that others are gong through the same things you are. WE look forward to getting to know you better!

Cyn

paulah
Lady

I’m getting out more often.It’s not as bad as we make it.I’ve gotten a lot of compliments from women.My ex girlfriend is really a great support to me.

seana evosevich
Lady

hi im a 53 yearold crossdresseristartedwheniwas 7itrydon momspantyhose and had a sexualexperiance

Lucinda Hawkns
Lady
Member

i am 53 years old and have been a cross dresser for many years. started when i was about 10 or so. school play, had to wear tights. that was all it took i was hooked from there on. i still dress up. wife knows and lets me dress up but only when 2 kids are in bed or out. i love dressing up and being feminine i feel more relaxed. i also looked on Craig’s list for a c.d friend to talk to and chat and get advice on make up. but i did find a cross dressing group… Read more »

stacy
Guest
stacy

Hi gurlfriends here’s my adventure into this fabulist lifestyle. I’ve been crossdressing since I was 8 as well, found a bag of my older sister clothes in the basement and tried on everything in that bag, I kept a few dresses and hide them down stairs, I’d try wearing the stuff when I got a chance….. When I was in my teens the house use to be empty, the car was gone so my friends thought I was out with my parents, I use to get dressed again in my older sisters clothes close all the curtains and play dressup… Read more »

Joseph C. Valaitis
Guest
Joseph C. Valaitis

when I was in my terns i would put on mu mom’s pantyhose and my sisters skikt and shoes. it felt good when i did itthen at the age of 55 aafter my wife passed away.i wore some.of her.clothes in private Now iny 60’s i want to try again

Josie
Guest
Josie

Plainly told and yet so true……

muskan
Guest
muskan

Hi i deel almost all cd come across such situation to try their mother sister or reletive brs panty or other clothing specially when ther are hanging in bath room slowly 2 one become habituated of it start driving pleasure of it and situation becomes such a grave when he is alone at home the urge og crossdressing become intolreble I am 70+ i also started from my child hood slowly 2 it became my passion of crossdressing when ever i am alone at home i am not able to control my self i dress up stands in front of… Read more »

Brandy timms
Lady

I have been a cross dresser like so many of you since I was young. The earliest I remember was about 15. As soon as my ex wife found out she divorced me. Then I found my current wife that is ten years younger than I am and right off she accepted and encouraged me to dress. She lays out my cloths daily. She even planned our wedding in Las Vegas with me wearing the wedding dress and she bought me a diamond engagement ring that I wear when dressed and a mans wedding band that I wear when I… Read more »

Randi Layne
Member

I hope that you have found a friend to help. My first experience of being completely dressed came about in a weird way. I was shopping at a thrift store, looking thru the rack of women’s underwear. Another customer, a young lady, complimented me on being a good husband by buying things for my wife. I was unusually bold and told her that the items were for myself and that I was a cross-dresser. Her reply? “I’ve always wanted to meet a cross-dresser”. The story ends with her getting permission from her husband to allow her to transform me –… Read more »

cdmelissalaquinta
Duchess
Member

So lucky to have met a person who would do this for you (and,presumably, for herself).

Indie
Lady

Wow, I thank that’s just about my ultimate dream. That must have been incredible.

Randi Layne
Member

It was incredible! Unfortunately she moved away and that ended our friendship. It was exactly what I would have wanted to continue. Plus, it was notv a sexual relationship, more like I was a doll that she liked to dress.

dizzylizzy lawson
Lady

Victoria I buy lots of clothes from the local goodwill they have no idea of who your buying them for or why your buying them also lots cheeper that way you might want to try that and you will be helping out a good cause also

Roberta Thomas
Lady

Hi Victoria Rose.May I say first of all what a lovely name.I started crossdressing when I was twelve years old.Started out wearing my mlthers pantyhose and progressed eventually to skirts and dresses.I was in the closet for years but since coming out to my wife a few years back she allows me to dress en femme every day.I akways think that wearing clothes appropriate for a woman of my age is the best way to go.Would love to be friends with you on here.If you need any advice send me a message.

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