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...
(Narrator POV) The rest of Thursday went by as normal with neither Jamie nor Sydney leaving their rooms even once. But by the time Friday morning had come around, they were each filled with a new kind of energy. Jamie was silent all morning, with his hand shaking as he scooped cereal into his mouth at the breakfast table. He was visibly frightened of what was going to be happening to him and he knew that he didn't have much say in it, he truly couldn't risk anything from the video getting out otherwise his life was over.
(Jamie POV) As I was getting dressed I could feel a cold sweat coming over me, and each breathe I took was only making my head feel heavier. I'd hardly even slept last night after the conversation I'd had with my sister yesterday. All of a sudden, there was a knock at my door and I jumped back scared. It was Sydney.
"Hi Jamie princess, I've decided that since you liked them so much, your going to be wearing a pair of my panties to school today".
Jamie gulped but couldn't bring himself to muster up any sort of response and instead just accepted his fate. He slipped on the lacey pink panties that Sydney had thrown at him before putting on his uniform over the top. As he left his room and went to exit through the front door he saw his sister was waiting for him.
"Show" she barked, and Jamie did just that at her demand.
"Good girl" she said with a beaming smile.
"I'm not a girl" Jamie said back unconvincingly
"Yes you are darling your my sister" responded Sydney, before kissing him on the forehead
They both left the house and made their way to school. Jamie already knew this was going to be a long day, and this was just the beginning.
(Jamie POV) As I trotted up to the school gates I couldn't think about anything other than the bright pink thong that was currently tearing apart my ass cheeks. In the corner of my eye, I see the boys were all waiting for me and slowly approaching.
"Jamie are you good man? you don't look so good" Danny said. "Yeah whats happened to you" Matt laughed. "I'm fine let's just go" Jamie shot back, marching femininely towards the class. "Jamie why are you walking like a girl?" Sam piped up in rare fashion. "Fuck off" Jamie roared as he swayed his hips into class.
It wasn't until lunch time when Jamie saw Sydney again, and, despite his best efforts to avoid her, she approached him intently and whispered in his ear "How's the thong babes" with a cheeky smile. "It's fine" Jamie replied, scared to upset his now powerful sister. She grabbed the waistband of his trousers and pulled him to the side before reaching for his panties and giving him the hardest wedgie she possibly could.
"Ahhhhhhhhhhh" moaned Jamie, somewhat turned on by the altercation
"Good girl" whispered Sydney, who then proceeded to kiss him square on the lips before walking off
By this point Jamie had already came and was still brutally throbbing in a crumpled up mess in the corner. He couldn't believe his own sister had just kissed him like that on the lips. It was officially his first kiss, and he was not complaining one bit with how it went.
When they got home, Sydney wasted no time in following Jamie into his room.
"Strip. NOW" she ordered and I obeyed, taking of my trousers and shirt until I was left in just her pink thong.
"Makeup. Wig. Immediately". Again, terrified of the consequences, I followed her orders and slipped on my black wig before attending to my makeup.
In perfect timing, I finished my makeup and my door barged open and Sydney walked in wearing only her underwear, with her school uniform in hand.
My penis grew hard at the beautiful sight of her and I took the clothes and put them on without any words being exchanged as by now I knew what she wanted. As she got her phone ready I posed for the photo.
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"Oh wow Jamie aren't you a sexy little bitch" she exclaimed proudly, leaving me to only further imagine how far she could be planning to take this.
