This will be the first of a multi part series. Much of it is based on fact. A big part of writing and reading is for the reader to decide which is fact and which is fiction. I will leave that all to your imagination. Please read my other stories and give me some feedback.
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Even at 18 years old I knew I was different from the other boys. I am 5-6, but very thin and hardly any body hair. When I am in the locker room I saw the size of the cocks and felt humiliated at how much smaller mine is.
At home I tend to get lost in my school work except for when my mother is out. When that happens, my older sister, Becca, loves to parade around in her underwear. At 21 she is 3 years older than me and has the reputation of being the town tramp. My mother hates that, but when she is out, Becca loves to walk around like a real slut teasing both my father and I.
Throughout most of the day, she was in red garters, stockings, red knickers and bra. I tried to concentrate on what I was doing, but I could not help but stare at her. She knew what she was doing and smiled at me as she wiggled her arse. After a while my father left for work and she went out with her friends.
I had planned to just do some school work and maybe jerk off, but for whatever reason I went into her bedroom. There on the bed I saw her red underwear, she must have changed before she left. I could not help myself, I went inside and I could still feel how warm they were. When I touched her knickers there were not only warm bit wet. I had always suspected that she got off on prancing around like that, and now I knew I was right.
Without a second thought, I took off my clothes and put her clothing on. First the garter belt and then I rolled up her stockings, being careful not to tear them. When I put her tight knickers on my tiny cock pressed into them and barely made a bulge. Since we were close in body size, when I put her bra on it fit nicely. I went into her hamper and found some dirty knickers and stuffed the bra and looked at myself in the mirror. I loved what I saw! All I needed was a wig and I might have passed for a woman.
At this point I was thinking of jerking off when in the mirror I saw the reflection of Becca. I knew there was no way of explaining this away and started to cry. Instead of yelling at me or slapping me in the face, she simply took me in her arms and held me tight.
Finally I looked up at her and said in a soft voice, "I am sorry."
She stroked my face and smiled. "Don't be sorry dear, I had suspected you might be a sissy for a long time. I was hoping by leaving my clothes out and sneaking back in that you would do this. I am glad you did!"
