The Diary & Stories of a Girly-Boy-In-Boots…
Jamie-Lynn & Miss Sasha - Introduction:
My name is Jamie - but I like being called Jamie Lynn.
I am a 25 year old girlish boy with a slim, smooth, delicate, hairless feminine body who loves girls clothing.
I was often mistaken as a girl in my teens and was inspired by the pretty girly-girls in my high-school. I started to explore and liked dressing like a girl. I never thought it would be so fun.
My parents divorced when I was 10 years old. I was 12 when my father met Sasha who became his second wife and my new step-mother when I was 13. It took me some time to get used to the idea of a step-mother, but began to appreciate and like her. Now, I absolutely adore her.
She is a beautiful woman with long dark brown hair, a gorgeous fit body with firm smooth 35B cup sized breasts; an elegant pretty face with full lips and a sexy, daring, provocative style of dressing. When puberty started for me, her sexy outfits and sweet smelling perfume caused me to start getting erections.
Her tight form-fitting outfits like jeans, leggings, spandex exercise shorts and bras, dresses, skirts and tops made me wonder how sexy she must feel. Especially when she wore her knee-high leather heeled boots or shiny rubber rain boots with tight jeans. I now have a strong fetish for wearing boots.
I know now she loved to tease me by unexpectedly giving me tight hugs telling me how much of a “cutie” I was, and that I would probably grow up to break a few hearts someday.
With the side of my face pressed against her firm breasts inhaling her sweet smelling perfume feeling the smooth skin of her arms wrapped tightly around me was wonderful. I quickly developed a crush for her and understood why my father was attracted to her.
My father died in a car accident when I was 14, making Sasha my legal guardian. My birth mother re-married and is estranged to me; we don’t communicate anymore.
When I was about 15, with my father gone and just myself and Miss Sasha, I started to wonder what wearing pantyhose felt like and started to experiment. I loved the look and feel of Sasha's skin-tight glossy pantyhose on my smooth legs wearing her leather knee-high boots that fit my legs so well.
She eventually discovered I was trying her sexy clothes and boots on when I was alone at home. I am twenty-five now - she now accepts, allows and enjoys to play dress-up together and be her pretty girly-boy around our apartment.
My name is Jamie - but I like being called Jamie Lynn.
I am a 25 year old girlish boy with a slim, smooth, delicate, hairless feminine body who loves girls clothing.
I was often mistaken as a girl in my teens and was inspired by the pretty girly-girls in my high-school. I started to explore and liked dressing like a girl. I never thought it would be so fun.
My parents divorced when I was 10 years old. I was 12 when my father met Sasha who became his second wife and my new step-mother when I was 13. It took me some time to get used to the idea of a step-mother, but began to appreciate and like her. Now, I absolutely adore her.
She is a beautiful woman with long dark brown hair, a gorgeous fit body with firm smooth 35B cup sized breasts; an elegant pretty face with full lips and a sexy, daring, provocative style of dressing. When puberty started for me, her sexy outfits and sweet smelling perfume caused me to start getting erections.
Her tight form-fitting outfits like jeans, leggings, spandex exercise shorts and bras, dresses, skirts and tops made me wonder how sexy she must feel. Especially when she wore her knee-high leather heeled boots or shiny rubber rain boots with tight jeans. I now have a strong fetish for wearing boots.
I know now she loved to tease me by unexpectedly giving me tight hugs telling me how much of a “cutie” I was, and that I would probably grow up to break a few hearts someday.
With the side of my face pressed against her firm breasts inhaling her sweet smelling perfume feeling the smooth skin of her arms wrapped tightly around me was wonderful. I quickly developed a crush for her and understood why my father was attracted to her.
My father died in a car accident when I was 14, making Sasha my legal guardian. My birth mother re-married and is estranged to me; we don’t communicate anymore.
When I was about 15, with my father gone and just myself and Miss Sasha, I started to wonder what wearing pantyhose felt like and started to experiment. I loved the look and feel of Sasha's skin-tight glossy pantyhose on my smooth legs wearing her leather knee-high boots that fit my legs so well.
She eventually discovered I was trying her sexy clothes and boots on when I was alone at home. I am twenty-five now - she now accepts, allows and enjoys to play dress-up together and be her pretty girly-boy around our apartment.
4 years ago