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Its Halloween season so time to tell my first crossdressing experience

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Posts: 293
Lady
Topic starter
(@brandie)
Honorable Member     Lenoir, Tennessee, United States of America
Joined: 4 years ago

 When I was 15 I was riding home from school and my mother asked did I have any Halloween plans. I told her no. I never really thought about it I thought I was getting too old for it anyways. She said no you will never be to old to dress up and have fun you have a costume in mind? I said no I not even thought about halloween or costumes. Then she said something that will change my life. Do you remember my Elvira costume? The tight fitting witch costume with a split up to the hip stiletto heels and fishnet stockings hell yea I remember it. I said yea I remember it a little. MOM said Well you can wear it for halloween if you want and come out with. My heart skipped a beat did she know I was sneaking into her closet when I was home sick or when I was home alone. I played it cool I told her I dunn mom about dressing like a girl that sounds gay. She said no its Halloween no one will care besides you will look cute and no one will know its you. I said ok I will try it on and see she told me ok I will dig it out when we get home. That was the last I heard about it for a few days I thought she forgot about it. One day I came home and laying on the bed was the costume mom said she gave me black tights so I dont have to shave and ankle boots because they will be easier to walk in than heels. I then tried it on and it fit like a glove Mom said I looked cute but we need to get a fake nose and witch make up. Then I was told dont change yet you need to practice walking in those boots. I wore that outfit for a few hours loving all the new sensations I was having. The next day I was at Big lots and found a witch mask with wig and face mask attached. Now I have my costume complete for halloween, when the night rolled around mom gave me a leotard. She said put this on over your tights it's going to be cold and it will keep you warm and hide your manhood. When I stepped outside I was amazed how I had thin clothes on but still warm. My family met up with my aunt and her inlaws and we all went trick or treating and everyone thought I was a teenage girl. Even when I shoed my face as a boy they loved it more. At the end of the night I did not want to change because I knew it would be a year before I got to crossdress again and I was going to I was hooked right then and there,

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4 Replies
Posts: 934
Lady
(@ashleigh)
Noble Member     Ocala, Florida, United States of America
Joined: 9 years ago

Great story! Thanks for sharing it. It seems you have a very astute, understanding Mom. Waiting a year between CD sessions would be unbearable. I go crazy when I can’t dress over a weekend. Lol.

Emily

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Posts: 102
Lady
(@sabinewren1388)
Estimable Member     Lakeside, California, United States of America
Joined: 4 years ago

I think that was a very clever way your mom could broach the subject and show that she was accepting of you. She rocks!!!

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Posts: 25
Lady
(@peterlinda5170)
Eminent Member     Hamilton, Ontario, Canada
Joined: 4 years ago

What a great mom it was nice for her to open the door for you I bet you didn't  have to wait a year to dress in front of her again

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Posts: 1508
(@debbiedd)
Noble Member     los angeles, California, United States of America
Joined: 5 years ago

How sweet of your mom to open the door and let you experience something that would be with you the rest of your life.

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