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How I Became My Grandmother;s Special Granddaughter

My grandmother helped, and guided me into the world of femininity, that  I will never forget and will always be grateful to her for seeing the pretty girl that was insde me. She passed away many years ago, but is always with me,. She discovered my girlish desires when I was 11 years old. She was a sales clerk at Lord&Taylor's, a large department store here on Long Island, NY. She bought me the prettiest dresses, lovely petticoatss,patent leather mary janes, lace anklets, panties, blouses, and skirts that she taught me how to wear, and how to conduct myself as a young lady at all times when I visited her. All this started as I said when I was just turning 11, A little about myself, before I continue with this story. I was an only child, I lost my father when I was 3, he died in an car accident, so it was just my mother and I in our home. My grandmother who was a widdow, was my father's mother. My grandfather passed away before I was born. My dad was my grandmother's only child, and she grew up in a family of 4 brothers and no sisters. On weekends, my mother left me at grandma's because I loved to visit with her, and keep company with her. One day I discovered something in her clothes hamper which caught my attention. I took it out and held it iun my hands. It was a lady's nightgown, I knee it b, elonged to my grandmother, I stared at it for a few minutes while holding it, it felt so nice and soft, it was also very pretty, for some reason, I wanted to put it on me, maybe because it was my grandmother's, and I loved her very much, so I removed my shirt, pants, shoes and socks, and then slipped it over my head, and let it gently come down over my shoulders and it covered my body. What a delicious shudder I felt as it was on me, It was a wonderful feeling, I enjoyed it very much, I began to walk back and forth in her bathroom, lokking in the mirror and touching the nightgown  with my hands, rubbing it against my body, and loving how I felt. A few minutes later though, I began to worry that she might see me wearing her nightgown, what would she think! I quickly took it off got dressed in my clothes and put it back in the hamper and left the bathroom. Everytime I visited her after that, I would go to the bathroom first chance I had. close the door, and check out her clothes hamper to see if there was anything in there, hoping to see another nightgown . To my delight there was, it was a different one but jusy as pretty as the first one I had tried on. so I wore it too. This rountine went on for about a month, always there was a nightgown in the hamper I could wear. It had gotten to the point, where I needed to see my grandmother, in the hope that I could always in secret, wear her pretty nightgowns. One weekend after I had dressed up in her nightgown, she caught me, i had not locked the bathroom door, I was too excited about putting on her nightgown, I thought I was going to die, I was so frightened thinking she would be angry with me. But she just smiled and told me that she had known what I was doing for quite a while when i stayed with her. She knew after the first week, I had been wearing her nightgowns, because as careful as I thought I had been putting them back in the hamper, she knew they had been touched by me. She saw me start to cry and held me in her arms, gently rocking me, telling me not to worry, that she wouldn;t tell my mom or anyone about what I had been doing. I felt so grateful to her, told her I was sorry, I loved her, and would never dress up in her nightgowns again. She then surprised me, told me it was okay for me to feel pretty in her nightgowns. She then explained how I was just trying to enjoy myself, and if I liked wearing girls clothes, she would help to make me become the pretty girl I dreamed about being. She said that she would like to make my dreams and hers come true. I was confused, she explained that I could be the little girl she never had and always wanted. So I began my life as her pretty graanddaughter. From that moment on, she helped to feminize me from head to toe, changing me into the sissy  I was to become. I wore beautiful dresses all the time I visited her after that day. She taught me how to dress,lhow to walk,and how to sit like a girl, how to learn all the feminine mannerisms, I would need to learn to be a girl, over the years it was a grueling experience, but one I learned very well. I learned about how to apply makeup, how to do my nails, I had let my hair grow long, it was back in the 60's when long hair was popular with boys,, I learned how to do my hair in a feminine way,everything I needed tto know and learn about being a girl was taught to me by my grandmother. She is gone now, as I said in the beginning of this story, but i will always remember how she was the one who made me love to wear pretty dresses, and become the sissy I love to be , and will always be!

missprettypinktoes missprettypinktoes 61-65, M 6 Responses Jan 17, 2010

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Great read. Lucky you

Wonderful grandmother! What a girlish blessing for both of you it must have been. Am sure you are still missing her to this day.

This is so nice Priscella. If only there were more grandmothers like yours. Back in the early sixties, this was a No-no, even with the sixties hippy generation.

what a wonderful story. I too played with my grandmorthers things when I visited her. I mostly played in my mom's things though. Mom eventually found out like your grandmother did but didn't say anything about it. She never helped me with it, but never was opposed to me wearing her things. She would sometimes give me hand me down underwear of hers or ask me if I wanted it before she discarded it. Most if not all of it I took. She knew I prefered her used things ...

i also want like this grand mother

What a wonderful grandmother!!