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crossdressing

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Did your mother ever dress you up as a girl? For Halloween or punishment? What age?
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I wish my mom would dress me up for halloween
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Quote by Kayla2
Did your mother ever dress you up as a girl? For Halloween or punishment? What age?


My father used to occasionally "punish" us by having us wear my older sister's dresses - silly man, look what he got me into! Those "punishments" were SO harsh! Too bad Dad didn't also insist that I wear her panties and bra (I did that on my own).
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My mother made me wear a dress for an entire weekend because I pissed my pants . I didnt want to stop playing so I would wait as long as I could . My sister told her what I was doing so she made me wear a dress and panties to humiliate me . My sister started making sure that I didnt make it to the bathroom after that just to see me in a dress.

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No, but my Mother had said she expected to have girls instead of boys - no THAT led to some fantasies!

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My mom allowed me to play dress up. She was very supportive of it. For me it was not a punishment, rather a reward.

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First let me start by saying I am not a crossdresser I am a transgirl but you asked about Halloween so....

At 6 I said I wanted to be a princess for Halloween. My parents were reluctant but my sister said she'd help me with my hair and makeup before school that day and take me trick or treating with them in the evening. Like I said, my parents were really reluctant, my mom more so than my dad but they agreed to let me.

For the entire month of October I was thinking about how I might look and feel . When that day/night night came around it was magical (no pun intended). A few days before we got my costume, a lovely pink and white satin princess dress with a tiara. My sister bought me some matching shoes a little girl's clutch purse and clip on earrings. In another bag were some underthings. A little white nylon slip and a pack of girls panties. She asked me if I wanted to wear that stuff too and I nodded.

The clothes and outfit was so soft and so different than my boy clothes and i loved how i felt walking in it with the material caressing my legs.

I got up 2 hours early because I was so anxious that I couldn't sleep and I was told to be up an hour earlier than normal. My mom and my sister helped me get dressed then my mom went to work and my sister did my makeup and hair and showed me how to powder my face and reapply lipgloss then that stuff went into the clutch purse and she drove me to school.

A lot of kids made fun of me but not everyone, some girls thought i looked really good and didn't know who I was at first thinking i was a new girl in the school. That made me feel really good. They asked me questions about my hair and makeup and I told them my sister helped me. They asked me to sit with them at lunch (normally I sat alone). I felt accepted on some small level as another girl.

That night my family took me trick or treating and no one in the neighborhood knew who I was, they thought I might be one of my cousins.

After it trick or treating was over, my mom was like "well you had quite a day, let's get you out of that costume" and I asked if I could keep it on and she asked me why since Halloween was over and I said because I felt I was a girl inside and I liked how it felt and I wished I could wear dresses every day.

And kind of stunned she just walked out of the room, got my dad and asked me to tell him what I told her. I did and my dad kind of just nodded like he expected this and the two of them walked out of the room before coming back and saying I could keep it on until bedtime.

I began wearing those panties under my boy clothes and my parents asked if I'd like to see someone to talk about my feelings. I said yes.

The rest is history, I started seeing a child psychologist and she recommended i be allowed to play how i wanted and dress how i wanted at home after school and on weekends or vacation. A year later my room was repainted in all disney princess colors pink and lavender and i got a girl's bed and night stand set. I got clothes handed down from my sisters and some new things my mom bought towards the end of the year.

At 12 they realized it wasn't a phase and I started testosterone blockers and we got my name legally changed. I also went to school wearing a dress for the first time since that Halloween.

A year or so later I began estrogen hormones and 5 years ago I had surgery.

I'm 22 now and in college and no one knows I'm trans.

colin123
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My wife dresses me up for naughty sex sessions, check us both out in my picture gallery on my profile.

colin123
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I love to crossdress, use my wifes lingerie. Check us both out in my gallery.

Active Ink Slinger
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Neither my mom nor my dad dressed me. I dressed myself in my mom's lingerie. I fantasized about my mom. We never played. But I did get off many times using her panties, slips, stockings and negligees... From time to time I still enjoy wearing ...especially panties and stockings. My wife does not know, but I steal her panties. And finally, I enjoy playing with a man who is dressed.

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My Mom helped me to be who I am today.She feminized me and I'm forever grateful

Rookie Scribe
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I never had anyone to help me dress until I was in my 50s and went for a professional makeover. I really wish that I had an older sister that could have helped me. I started dressing around 10 when I have the house to myself. I had the pleasure of being told most of my early life that I was supposed to be a girl by my mother.

colin123
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My first crossdressing experience was when my wife asked me to wear her panties, I got so excited that she now gets me to crossdress for her pleasure. Check out my gallery pictures.

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My sister dressed up as her little doll when I was younger

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Quote by Kayla2
Did your mother ever dress you up as a girl? For Halloween or punishment? What age?

Yes, I remember when I was 5 her dressing me. I protested but secretly loved getting dressed and having lipstick put on my lips

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Quote by Yael_L

I never had anyone to help me dress until I was in my 50s and went for a professional makeover. I really wish that I had an older sister that could have helped me. I started dressing around 10 when I have the house to myself. I had the pleasure of being told most of my early life that I was supposed to be a girl by my mother.

Do you think your mom would have helped you if you told her you wanted to dress as a girl after she told you you were supposed to be a girl?

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Quote by nycdoc319

Yes, I remember when I was 5 her dressing me. I protested but secretly loved getting dressed and having lipstick put on my lips

did you ever tell her you liked it?

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My Mom did dress me as a girl as punishment for wearing my sisters clothes.This happened before I was in my teens.I have been dressing ever since.