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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 too old to dress up and have fun you have a costume in mind? I said no Ivenot 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 us. 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 duno 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 showed 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,
Brandy,
That sounds like a ton of fun. I could never have done that as a kid, and now if I tried it, my wife would probably have a cow. 😁
Much love,
Raquel
That brings back memories of when I used to sneak some dressing up time, as many of us did. The joy when, in fun, I was dressed as a girl and went out. Did mother know? She swears to this day that she never had any idea. It matters not as they were joyous occasions and my mother is quite at ease with me as I am now.
Thanks for sharing this great story. So cute and fun.
Jessica 🙂
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Great story. I bet your mom never knew what effect it would have on you but she sounds like a great mother.
I always wanted to dress as some version of a female on Halloween but the wife never would allow it even though I asked each year. When I came out to her she said “Now I understand some things about you”…. lol
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