Jake's new clothes

Jake was thrilled during the ride home. He couldn't wait to try out his new Dildo and fuck himself silly. Little did he know how difficult the first time is. Jane however was frustrated at her mom for making her stop asking. She really wanted to know what it was. Couldn't have been anything good. Once they got home, Jake ran to his room and unboxed his new toy as quickly as possible.

'Jesus Christ' He thought to himself upon seeing it up close. 7 inches was as big as he was, and will never be again. The thought of his dick being permanently smaller than it was yesterday turned him on to his surprise. But the most arousing thing so far was getting this boy inside him.

Jane burst into Jake's bedroom yelling, "JAKE WHAT'D YOU GET!" She immediately saw him holding his new pink Dildo. "OH MY FUCKING GOD YOU BOUGHT YOURSELF A DILDO!!! AAAAAHAHAHAHAAAA! You're voluntarily becoming a sissy ass bitch now!"

Jake quickly put it away as she was talking, but the damage was done. She knew about his new toy. He became extremely frustrated at Jane for picking on him so hard

"You know what, it's a good thing. Because these are your new clothes!" Jane said, placing Jakes brand new clothing onto his bed.

"Holy fuck." Jake couldn't help but let out seeing the new clothes his sister presented him. She had fully replaced everything in Jake's wardrobe with brand new female clothes. Cute little pink panties, skirts, tank tops, new socks and everything. All of it reeked of a highschool femboy slut.

"What the fuck! Do you honestly expect me to wear all this?"

"Yes." Jane said earnestly.

"I'm not wearing fucking any of this. You're crazy. I don't care what you do."

"Ok one second." Jane quickly stepped out of Jake's room for a few minutes. The entire time Jake was getting only more and more anxious for what she'd do next. Jane stepped back in.

"Ok. Now you have ****."

"What did you do?" Jake asked now very concerned.

"Check your drawers." Jake looked at the clothes on his bed, then turned to his drawers. 'What the fuck did she do!'. Jake approached his drawers and carefully opened. Everything she just bought him and more had replaced all of his old clothes.

"What. The fuck." Jake said looking back at his sister. He looked back on his bed where the clothes were before only to find they were no longer there.

"Jake why are you naked!?" Jane pointed at Jake's exposed erect penis and he was suddenly naked. His phone and wallet were in his pocket, so they suddenly fell to the ground.

"Ah!" Jake tried to cover his hard dick, but it was difficult to cover it completely when his hands were only able to hover slightly above it."

"I'm gonna help you pick out an outfit. But only after this." Jane said approaching Jake and grabbing his cock. Jake let out a disconcertingly girly moan.

"Cum already." Jane said impatiently as she started jerking him off quickly.

"Ah! Jane! Slow down! I-" Jane took his cock into her mouth and he blew his load immediately. Shooting rope after rope of cum into his sisters mouth. She loved drinking her brothers cum. This load was even bigger than the last. By this point he was cumming a double shot worth of semen. His dick decreased by another CM as he blew, dwindling down to 14 CM / 5.5 Inches. He was now only barely average. As Jake started coming down from his powerful orgasm, Jane swallowed the rest of his cum and stood up. He felt his chest slightly swell, his ass mildly inflate, and his prostate suddenly felt more sensitive. He wouldn't know how to describe how it felt, but it was pleasurable. He wouldn't notice until later but his face had also grown softer and more feminine. Jane was shocked by how much he changed with the one orgasm.

"Tonight I'm gonna help you use that toy. You're going to be the biggest fucking sissy slut the world has ever seen. Wear these." Jane assembled a new outfit for Jake from his drawers. Panties with a small bow on the front, Thigh high socks, a small bra, and a large and loose hoodie. Everything she picked out for him was a matching hot pink.

"Ok." Jake said. Both defeated, but entirely ecstatic to get fucked as soon as possible.