What do you think?

Jake had been discreet the whole day at school. His sister and her friend Sally had been on a school trip, so he received no further torment from the two younger girls. His bra was well hidden underneath his jumper and blazer, luckily the curves were not to easy to spot! He did have to steal a second of his sister's blouses however, the one he had been wearing for the past two days have developed quite the stench due to all of his nervous sweating. Raiding his younger sister's wardrobe was not something that he was proud to do, but he found himself doing it nonetheless.

Yet again after school, he made his excuses to his mother and headed off to the mall. Jake didn't want to acquire any more girls items from Sadie, but the brisk pace that he ventured at seemed to defy that sentiment. It was as if his body was far too excited for the experience, despite the fact his mind found it daunting. Reaching the mall, he put his hand down his trousers to pull his panties from his arse, he still couldn't get used to them being up there! Entering, he approached the boutique, approaching his certain humiliation.

"Hi Jake! Glad you could make it!" Sadie beamed over to him, aware of the mysterious power she seemed to have over the boy. "How is your new bra, do you like it!"
"Yes," Jake replied, even though he actually hated. Was he just saying it to be polite?
"Brilliant! Well, if you could just pay for it now that would be cracking! My boss has been on my back about it all day long! Its just £12.99!" she held her hand out expectantly. Jake obliged, handing over a £20 note. "Oh Jake, for another £7 you can take a five pack of these white ankle socks, they're perfect for wearing too school." He looked over at the socks on the counter, they had thrills along the top and were extremely girly.
"Okay, yeah please," Jake responded. Again, he couldn't work out why he had wanted the socks.
"Lovely, and here's your penny change," Sadie said as the till popped open with a jingle.

"Well Jake, I brought my old stuff in for you, it seemed a waste to leave it in the back of the closet. I think you should take it home and go through it all. There's a lot of stuff in there, my old jumpers, blazer, a couple of pairs of trousers...." Sadie continued. "I think it should all fit you, regardless, you'll look super cute in it anyway. I reckon you should just wear it whatever!" Jake didn't know it, but that command sealed his fate.
"Thanks," the boy replied, slightly helpless.

"Oh, there's also a couple of skirts in there too, although, if your going to wear them you should get some tights as well, its rather cold at the moment. You should pop back into here when you decide to wear them and I'll help get you a pair that fits properly!" Sadie smiled some more at Jake who was mortified at the prospect of wearing a skirt. "They say that we're going to have a mini-heatwave at the start of next week so you should probably start wearing them then! Show those lovely legs of yours off!" He couldn't believe, but Jake found himself mulling over the prospect of wearing a skirt to school next week, it may have only been for a split second, but he thought about it nonetheless.

"Anyways, I'll see you later Jake!" Sadie beamed.

Jake left to go home, and prepare his outfit for the following day.