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When I Was A Kid
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Straight Male / 19
My Older Step Sister
When I was three Mom got a divorce and I never saw my Dad again. Mom gets child support from him and got a house, car and a ton of money but I guess he sees me as a burden or mistake because not so much as a Christmas card.
When I was four Mom met a guy and I had to call him "Uncle Salvatore." He looks and talks like a mobster straight out of a movie but he's about the nicest guy you ever met which I am sure factored into them getting married when the divorce was final which was when I was five.
At first I was upset. Despite Mom having lots of money, we only had a two bedroom condo. That meant sharing my small bedroom with my new 12 year old step sister. Salvatore didn't make as much money as Mom had but he worked a lot to earn it while Mom didn't but that meant Mom had a lot of time to spend with me, at least until they started dating.
After the wedding it was announced that Margaret was going to be baby sitting me for the whole two weeks of their honeymoon which was a week in Hawaii and a week in Paris. To me she was practically a woman but looking back I can see how most people would say she isn't nearly old enough for that kind of responsibility. At least we had Mom's sister check in with us every evening and our neighbor Mrs. Sanchez came over almost every day and was always home so it wasn't complete independence from adult supervision.
First night I suggested Margaret should sleep in our parent's room and let me have my room back if only for two weeks. Margaret had a different idea. That evening around 9 pm, an hour or two after my bed time she announced it was time for my bath. I had been bathing myself for a few months with only my Mom peeking in on me to make sure I was doing it right. Margaret didn't think that doing that was anywhere near sufficient participation on her part. She decided she was going to bathe me. I was having none of that and started to scream until she began tickling my back with her soapy hand at which point my entire opinion on whether I was old enough to bathe myself was given a complete rethink.
Margaret's hands were magical. The pleasure they radiated was excruciating. No point on my body was safe from the ten fingered tingle monster. While I am not 100% certain, I think I had my first ever orgasm in that bathtub. I believe with boys it's called a dry cum but being in the bathtub with that part of me under a foot of warm tingly water, I'm not sure the word "dry" best describes it.
From that point on I was like a loyal puppy dog following her around mesmerized by her dominance over me, a dominance I eagerly consented to. I was so smitten by her charms that if she suggested we take a leap off the roof of our 20 story building naked and set ourselves on fire on the way down I'd have done so eagerly and with glee as long as her hands were holding onto me on the way down.
One day when I was 7 we were all at the dinner table and Margaret started talking about how pretty I would have been if I had been a girl instead of a boy. I was mildly uncomfortable with the topic but since it was Margaret who was suggesting it I didn't protest. I wasn't just wrapped around her pinkie, I was grafted on. She suggested Mom stop taking me to the barber just for a couple of years to see what I looked like with long hair. She said "I bet he'd make an adorable girl with his long blond hair in pigtails." It had just never occurred to me to grow my hair long. I'd never had hair longer than an inch or so on top and always tapered around the edges.
When I was 9 Margaret was 16 and got her driver's license. by then my hair was down to the middle of my back and in a pony tail most of the time but the day after she got her license her Dad took her to buy her first car, It was old and used but he bought it off his sister whose husband was a mechanic and it was big and comfortable but not a luxury vehicle. So what does she do first day she has it? She decides to take me clothes shopping and then off to my first trip at the beauty salon. Dresses, and skirts and blouses and nighties and girl's shoes and other girly stuff later we're in the salon and she introduces me to the woman as her little sister. The woman gave me a perm, then I got a manicure, acrylic nails, even some make-up. Later she took me to the mall to get my ears pierced.
And that is how I became Madison.
When I was four Mom met a guy and I had to call him "Uncle Salvatore." He looks and talks like a mobster straight out of a movie but he's about the nicest guy you ever met which I am sure factored into them getting married when the divorce was final which was when I was five.
At first I was upset. Despite Mom having lots of money, we only had a two bedroom condo. That meant sharing my small bedroom with my new 12 year old step sister. Salvatore didn't make as much money as Mom had but he worked a lot to earn it while Mom didn't but that meant Mom had a lot of time to spend with me, at least until they started dating.
After the wedding it was announced that Margaret was going to be baby sitting me for the whole two weeks of their honeymoon which was a week in Hawaii and a week in Paris. To me she was practically a woman but looking back I can see how most people would say she isn't nearly old enough for that kind of responsibility. At least we had Mom's sister check in with us every evening and our neighbor Mrs. Sanchez came over almost every day and was always home so it wasn't complete independence from adult supervision.
First night I suggested Margaret should sleep in our parent's room and let me have my room back if only for two weeks. Margaret had a different idea. That evening around 9 pm, an hour or two after my bed time she announced it was time for my bath. I had been bathing myself for a few months with only my Mom peeking in on me to make sure I was doing it right. Margaret didn't think that doing that was anywhere near sufficient participation on her part. She decided she was going to bathe me. I was having none of that and started to scream until she began tickling my back with her soapy hand at which point my entire opinion on whether I was old enough to bathe myself was given a complete rethink.
Margaret's hands were magical. The pleasure they radiated was excruciating. No point on my body was safe from the ten fingered tingle monster. While I am not 100% certain, I think I had my first ever orgasm in that bathtub. I believe with boys it's called a dry cum but being in the bathtub with that part of me under a foot of warm tingly water, I'm not sure the word "dry" best describes it.
From that point on I was like a loyal puppy dog following her around mesmerized by her dominance over me, a dominance I eagerly consented to. I was so smitten by her charms that if she suggested we take a leap off the roof of our 20 story building naked and set ourselves on fire on the way down I'd have done so eagerly and with glee as long as her hands were holding onto me on the way down.
One day when I was 7 we were all at the dinner table and Margaret started talking about how pretty I would have been if I had been a girl instead of a boy. I was mildly uncomfortable with the topic but since it was Margaret who was suggesting it I didn't protest. I wasn't just wrapped around her pinkie, I was grafted on. She suggested Mom stop taking me to the barber just for a couple of years to see what I looked like with long hair. She said "I bet he'd make an adorable girl with his long blond hair in pigtails." It had just never occurred to me to grow my hair long. I'd never had hair longer than an inch or so on top and always tapered around the edges.
When I was 9 Margaret was 16 and got her driver's license. by then my hair was down to the middle of my back and in a pony tail most of the time but the day after she got her license her Dad took her to buy her first car, It was old and used but he bought it off his sister whose husband was a mechanic and it was big and comfortable but not a luxury vehicle. So what does she do first day she has it? She decides to take me clothes shopping and then off to my first trip at the beauty salon. Dresses, and skirts and blouses and nighties and girl's shoes and other girly stuff later we're in the salon and she introduces me to the woman as her little sister. The woman gave me a perm, then I got a manicure, acrylic nails, even some make-up. Later she took me to the mall to get my ears pierced.
And that is how I became Madison.
