Jessica's Forced Sissy Boyfriend Taylor

An Unexpected Makeover

"Take them off" Jessica demanded, and with no hesitation Taylor did as he was told, revealing his rather average looking penis.
Unfazed, Jessica turned around to dig through her wardrobe before pulling out some clothes and handing them to Taylor.
"What do you want me to do with these" he questioned
"Put them on Taylor"
"But these ar-"
"Just put them on".
He thought for a moment about whether this was going to be worth it, before yet again coming to the conclusion that he had no choice; he could not risk losing out on this opportunity. Reluctantly , Taylor slid firstly a white pair of panties up his freshly shaved legs and immediately felt a cloud of shame looming over him as he picked up the matching bra. He slid his arms through the straps and allowed Jessica to fasten up the back.
"I'm not sure about thi-"
"SSHHHHH"
Next she picked up a tiny black skirt that was for sure going to show off more skin then Taylor ever normally would want to.
"Jess please, this is barely going to fit me" he pleaded, but she was having none of it.
"Do as I say, or I will make sure you regret it" Jess smiled in a an evil manner, which somewhat turned Taylor on.
He slid the tight fitting skirt up to his waist and sighed hopelessly in defeat.
"Ok now sit down and put these on, I'm going to get some makeup!" Jess exclaimed, handing him a pair of black thigh-high socks
"WHATT!?!?" Taylor shrieked back
"One second!" Jess replied as she collected up his old clothes and left the room.
Taylor could now feel himself going red with embarrassment but he was in too deep now, besides he didn't even know where jess had taken his clothes so leaving was hardly an option. Reluctantly, he slid the socks up to full length just above his knees and waited for Jess to return.
After 2 minutes she was back and carrying a smallish bag full of makeup, along with a long blonde wig.
"Jesssss this is going way to far now" Taylor panicked, but before he could fully stand, Jess slapped him across the face.
"Sit still and shut the fuck up" Jess ordered, fully aware of how helpless her little play toy really was. " I wasn't going to before but for that I'm painting your nails too".
Taylor immediately sat back down in silence and now accepted his defeat in its entirety. He held out his hands as Jess gently painted each of his nails with a darkish red polish. Once she was satisfied, it was time to deal with his face. Jess got to work and firstly plucked and trimmed his eyebrows into feminine arches. Next she covered his face in foundation, before adding concealer and hiding away his boy blemishes. She perfected his now thin, arched eyebrows and contoured his nose and cheeks. Then, she blushed and highlighted his face before applying a pair of false eyelashes , along with a thick coat of lipstick.
Lastly, she added the blonde wig and brushed it into shape.