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...
(Back to narrator POV) Just as he did every other Thursday, Jamie ditched his friends and sprinted home as fast as he could with a large grin on his face. As soon as he unbolted the door, he made his way upstairs and stripped from his school uniform until he was just in his boxers , before dashing directly to his sisters closet. After a reasonably short browsing session, he picked out a bra,a long sleeve brown knitted top and some short black shorts.
(Jamie's POV) After staring at Sydney's smooth legs earlier, I simply couldn't get them out of my mind even though I knew how wrong it was. "Fuck it" I said to myself, and ventured into the bathroom to grab a razor. This was the day I had decided, thinking little about the consequences and just convincing myself I can cover them with trousers. I pumped out a handful of shaving foam and proceeded to smear it into my legs, covering every hair on my body. Once I had finished, I grabbed the razor and just started shaving. I could feel my breathes getting heavier as I revealed my smooth skin with every stroke of the razor. I carefully glided it around my slight, but impressive for a boy, curves until my legs looked more feminine than ever before. I stared at them in awe and couldn't stop caressing them, they felt amazing. I slid my boxers back on and went back to the pile of clothes I'd picked out and left on Sydney's bed.
Just as I had entered, I spotted a pair of Sydney's panties sat in the corner of the room. They were white just as the ones I had seen her wearing today were and I couldn't help but feel my blood slowly flowing to my penis. Since I was taking risks and trying new things, again I said "Fuck it" and grabbed them. I had never worn her panties before as I felt it was crossing a privacy line and I had a genuine respect for my sister. But today I don't know what was coming over me. I threw my boxers to the other side of the room and slid her panties up my legs. They felt amazing and I was worried about ejaculating there and then. I just about kept my composure and put on the shorts, the bra and the top. Next up I went back to my room and grabbed my black wig form under my bed and fitted it on to my head before heading back to Sydney's room and doing my makeup. After all the practice I'd had, I had actually managed to get quite good at it and could make my face look quite convincing and feminine.
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(Jamie dressed up as a girl, above)
(Narrator POV) The rest of the day was not too different from any other Thursday for Jamie, he'd taken a look at himself in the mirror, took some pictures and jacked off to them as he usually would, before getting dressed back into his boy clothes, wiping off his makeup and putting everything back where he found it. "Another day, another slay" he said to himself, before welcoming back his mom and sister and acting as if he'd done nothing out of the ordinary for a teenage boy.
However one thing Jamie didn't realise that day is that he had seriously fucked up, and today was the beginning of the end for his secret crossdressing journey...
