My Sister Dressed Me Up As A Girl

Jamie and his Secrets

(Narrator's POV)
Jamie and Sydney grew up living with their parents, however their dad had passed away when they were both just 7 years old and so it had just been them and their mom ever since. Maybe it was partly due to the lack of a father figure at home Jamie had found himself becoming more and more curious the older he got and ever since the age of 11, he had been stealing clothes from his sister Sydney's room whenever he could.

It had started off as pure curiosity as he couldn't stop thinking about what it would be like to try on a dress. By the time he was 13, he was digging through his sisters clothes every other week just to check himself out in the mirror in her small selection of different summery dresses, always managing to make use of any time he could get the house to himself with his mom busy working and his sister out for whatever reason.

It wasn't until he was 15 years old and in year 10 that it became sexual for him and he would find himself trying more different types of clothing as Sydney's wardrobe gradually got older and more mature. By this stage just simply putting on a dress wasn't enough for him, he was accompanying every dressing session with masturbation and found that he got off to himself in the mirror. He had studied the different ways that the girls his age had put together their outfits and he tried his best to copy them. He had tried on almost everything in his sisters wardrobe, from short shorts, short skirts , tank tops and even had began experimenting with her bras just to give the illusion that he had his own pair of boobs.

In recent months Jamie was taking things even further and had begun trying out his sisters makeup, as well as discreetly ordering a wig online to further fulfil his fantasies. However even then, it was never enough for him as their was always something missing. He was being held back by the fact that he had to maintain his boyish appearance for when he's not dressing up in order to avoid causing any suspicion, meaning he never got the chance to properly shape his eyebrows or shave his legs like he so desperately wanted to.

This routine had always been a pretty safe one for Jamie as he would always wait for the house to be empty before he dressed up and was always extremely careful in making sure he put everything back exactly where he had found it . The moment he heard anyone coming home, he would always grab his boy clothes and lock himself inside his room so that he could get undressed and change back to his normal self, as well as wipe away any of Sydney's makeup that he had used with the makeup wipes he had purchased along with his faithful black wig. He would hide his wig and wipes underneath his bed and spend the next ten minutes or so sneaking around the house in his attempt to put back any clothing he had stolen back where he had found it without being caught, whether that was in his sisters room, the dirty laundry or even straight from the washing machine.

It was all part of a faultless routine that he had followed for years by the time he was 16 and he had never even come close to being caught, whilst as far as he was aware he had never even raised any suspicion on what he really got up to in his spare time. If any of his friends saw him when he was dressed up as a girl , he was convinced that they would probably find him attractive because he pretty much had a crush on himself .

He was beginning to feel like he could keep his secret forever and he would never be found out...