Chapter 5: Wednesday and Thurday

32.5K 65 4
                                    

It was late on the Tuesday night. Jacob couldn't sleep. All he could think about was the party and having to grind against someone's cock. Not just once but at least ten times. Jacob felt his silky smooth legs and his penis became hard. Girly thoughts flushed through his mind. Amelia was out and Jacob sneaked into her bedroom and locked the door behind him. Jacob was searching around in all of her drawers looking at all the stuff he could be wearing until his eyes fixed upon one thing. It was a dildo. 6 inches. Jacob stared at it. "It's only 6 inches. I am gonna be grinding against bigger on Thursday." Jacob thought to himself, "Everyone thinks I am a girl. Girls use dildos." He took the dildo out of the draw and stuck it to the wall. He managed to clasp a bra without any help and stuffed it with his breastforms. He put on one of his sisters thongs and got on all fours. He pulled his thong to one side and gently pushed back against the tip. It was gonna hurt. All of a sudden Jacob had an urge to push back all the way. Jacob felt the balls of the dildo against his ass. All 6 inches were in. Jacobs ass was hurting. He pulled the dildo out and put it away. He took off the bra and thong and put his breastforms away. But one thing caught his eye. A buttplug. Jacob heard the front door open. Amelia was home. Quickly Jacob took the buttplug and pushed it fully up his ass. It hurt but he had no time to stop. He unlocked the door and left his sisters room without a trace of him being in there. Jacob jumped into bed which he suddenly realised wasn't a good idea. One thing Jacob didn't realise was also that it was a vibrating buttplug that went off every half hour for 15 seconds. Jacob fell into a deep sleep before he noticed.

*TIMEJUMP TIL MORNING*

Jacob woke up to vibrating in his ass. He instantly gained pleasure. The buttplug was right next to his g-spot. He had to have in his ass in school as it would be embarrassing if he had to give his sister back her buttplug to her face. Jacob slipped on his dress and heels and got his makeup and hair done by Amelia. He was ready for the second day of school as a girl.

 He was ready for the second day of school as a girl

Oops! This image does not follow our content guidelines. To continue publishing, please remove it or upload a different image.

The dress clung tightly to his femme body. There was nothing Jacob could have done to prevent this. Jacob just embraced it as if he always wanted to be a girl. At the entrance to the school, Reuben gave his wink of approval. Jacob strutted into school and started going over to the girls until he was stopped by Jordan. "You didn't call me last night."he said.
"Oh shit, sorry!"Jacob exclaimed blushing.
"It's okay, wanna meet at lunch?"he asked.
"If that will make it up to you then sure."Jacob replied. Jacob naturally winked at him as he walked away. Jacob strutted over to the girls but before he could get there the bell had rang. First period was a nightmare for Jacob. His vibrating buttplug kept going off and he started to enjoy it and get used to it. Jacob thought this was a bad thing to start with but it was good as it didn't affect him for the rest of the day. Bell rang. Lunch had arrived. Jacob saw Jordan and Jordan had locked eyes with him. "This is my time to shine"Jacob thought,"Sexy time." Jacob walked with one foot infront of the other and swayed his hips from side to side. Jordan's eyes lit up.
"Heyy Jordan!"Jacob squealed as he hugged him.
"Hiya"Jordan spurted out. Jordan really did like Jacob. Not just liked, loved. "The way you walk is so hot"Jordan complimented.
"Thanks, I had been practicing that for you!"Jacob lied, "So what you wanna do?"
*buzz*
"Umm, whats that buzzing?"Jordan asked concerned.
"It's nothing."Jacob said now glowing red, "I wanna say that you are so fit."
Jacob leant into Jordan. Jordan put one hand on Jacobs ass and the other behind his head. Jacob wrapped his arms around Jordan and looked up at him. It all came so naturally. Jacob puckered his lips and Jordan leant into it. They started to kiss, tongue and all. Their romantic snog was rudely interrupted by the bell ringing. Jacob kissed Jordan on the cheek and strutted away, hips swaying goodbye.
The final period had began.
"Hey Jess, didn't think you knew Jordan?"said Ellie.
"Well, we get on okay."Jacob blushed.
"Did you know he is on the soccer team that we will be cheerleading for tonight?"asked Holly,"If you want, we can rig the system and make him the best player of the match for you. But you have to let us join in too."
"Yes please!!"Jacob spurted out.
"Well thats sorted then."said Holly.

Not Your Average Teen BoyWhere stories live. Discover now