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Teens Were The Best Years

While I had started dressing as a girl when I was 5 by my 2 older sisters and then my mother. To me dressing up just meant putting on clothes. I was too young to know or understand what crossdressing was. As I entered my teens I became aware of crossdressing and being born a boy. I still loved every opportunity to be a girl. But my greatest fun and memories were when I turned 18. Now I knew everything to do regarding crossdressing, hair, makeup, clothes, how to act and gestures. But when I turned 18 my mother would dress me herself and take me out. She would dress me in her clothes to make me look like a woman in her 20s. She would wash and set my hair. Do my makeup, lips and nails always bright red for that older look. Panties and bra were followed by a garter and stockings. (No pantyhose) The dress was always one that zipper up the back and was a solid color. Usually a lavender color, blk stocking and 3 in. matching shoes. Jewelry was always big earrings, necklace and bracelet with the occasional ring. When she was done I looked like a 25 yr old woman. She would dress to the 9s and out we would go. A mother and her older daughter going out to eat. Do some shopping for clothes or catch a movie. We would stay out to midnight walking and talking everywhere we went. It was always a long night but it was my mothers night. I enjoyed every minute of it and I know she did to. Today I'm older and wiser,when we go out I'm dressed just the way she likes me to be. And I'll never lose that feeling of how happy she is when I'm her daughter.
femboy4u femboy4u 22-25 8 Responses May 12, 2011

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I think you show a lot of sensitivity in this

Those of us who began at an early age had no concept of sex in connection with crossdressing. We just wanted to be like the women in our lives: Mothers, aunts, grandmothers, sisters, and cousins. Sex entered the equation at the same time it did for our non-crossdressing peers. And for those of us who had accepting and encouraging females in our lives, they were the best of times.

what a wonderful story you are so lucky all the very very best for the future

Great story, so happy you had a wonderful experience with your dressing growing up :)

What a sweet, sweet story. You are very lucky, honey.

Your mom and sisters really helped you.I had to learn on my own.My wife did help with somethiings. I didn't know what a crossdresser was until i was 17 . I just thought i was the only boy who like girls clothing.

I felt like i was the only boy who liked girls clothes too Cindy. So sad thay so many of us had to feel Isolated and freakish. Fortunately the internet is available for the younger generations.

that's an awesome story...would love to meet sometime

a young man should do just as his Mother says and I think yours is a mighty fine lady! I hope she continues to dress you and make you a sissy!