Ever since he was young, Jamie had known deep down that he had always been different to the other boys at school.
Growing up, he would continue to explore his fantasies further and further until one day his sister Sydney caught on and everything wou...
(Jamie POV) It was 7am on Saturday morning and mom had already left to see her sister across the country over an hour ago. All of a sudden, Sydney burst through my bedroom door in only her underwear and an open robe, sat down and took a picture of herself in my mirror.
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She then jumped on top of me and whispered in my ear
"Are you ready for our day sweetheart" before yet again seductively kissing me full on the lips.
I was throbbing ferociously and I am certain she noticed it through my thin bed covers as my hard penis pressed against her. "Yes Sydney" I replied, now feeling a little bit excited about the prospects ahead. I hardly even noticed any sort of pain as she plucked my eyebrows into feminine arches, I was very much distracted.
She got up and went back to her room before returning with an outfit and told me to put it on. Feeling encouraged, I took the slim fitting black top and tight jean mini skirt and proceeded to slide them on over a matching black bra and panties set along with a pair of thigh high socks.
"Ok put on your wig, today I will be styling it for you and doing your makeup" she said , which sounded sounded like all good news to me. Sydney spent the next few minutes working her magic and after what felt like forever, she was finished and led me to the mirror.
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(Jamie dressed as a girl, above) I barely recognised the beautiful girl staring back at me and I caught Sydney smiling at her work behind me.
"Aww don't you feel pretty Jamie" she teased, which only got my penis harder underneath the skirt.
"Yes I do thank you for this" I responded gratefully.
"Now you are ready for the next part of our day" she told me "I would like you to invite little Sammy over".
"Huh? Why? I can't let him see me like this Sydney please" I begged but I knew what the other outcome would be if I didn't do as she said.
"I'm afraid orders are orders Jamie, unless you want the whole school to find out how pretty a girl you are" she said softly.
"But why Sam?" I questioned to which she responded " everybody knows that he's been cumming over me in class, I think it's time he's put in his place too".
I had no choice but to invite Sam over and, within two texts, he was on his way.
