literature

The Orphan Part 7

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Henry walked into his first period class on the first day back from winter break. His new Mary Jane shoes clicked against the tile floor. He was nervous. His skirt felt shorter than it did when he tried it on for Aunt Rebecca, and he wasn't sure how good of a job it did of hiding his panties and boy parts. As he walked into the classroom, a few students who were already at their desks stared at him.

"New kid!" someone said.

Henry ignored the whispering students and made his way to the teacher's desk.

"Um... Hi. I'm Haley. I'm new."

"Oh yes. I heard I would be getting another. My name is Mr. Crenshaw, Ancient History." He extended an arm, and Henry's dainty hand shook it, his polished finger nails wrapping around Mr. Crenshaw's.

"You may sit over there," he instructed, pointing to a desk in the back of the room.

Henry made his way to his desk and plopped his new pink backpack (his aunt had surprised him the night before) next to his chair. He sat down and glanced at the other students, a few of which were looking back at him.

"Dude she's hot!" he heard one boy whisper to his friend. He suddenly felt very uncomfortable. Then he looked around the room and noticed something. He was the only person wearing a uniform. Everyone else dressed normally. Why was he the only one obeying school rules? Or was it not a rule? Then, much to Henry's horror, Jason walked into the classroom. He was groggy, having just woken up. He lumbered over to his desk, which was right in front of Henry, and sat down. He looked ahead for a moment, then realized someone was sitting behind him, and turned around.

Henry smiled, trying to look friendly. Jason's eyes lit up.

"Haley!?" he whispered.

"Um... Hi."

"What are you doing here?"

"I told you. My aunt enrolled me here."

"That's great!" he said. Clearly ecstatic that Henry was there.

"What's your schedule like?"

Henry pulled out his schedule and handed it to Jason.

"We.... we have every class together!"

Henry took the paper back. Could they possibly have every single class together? What were the odds of that?

"Are you mad at me?" Jason asked suddenly.

"What? No of course not!" Henry realized he was glaring at the paper. He didn't mean to offend Jason.

"Ever since we kissed, you've been acting a little weird. Did I do something wrong?"

"No it's just...."

"Do you not like me?"

"No of course I like you Jason. You're nice. It's just that I don't know if I can do this."

"Do what?" he asked.

Henry was trying to step around the issue.

"Be your... girlfriend."

The last word came with some difficulty.

"Ok," Jason said. "Well then lets take it slow," he grabbed Henry's hand and interlocked his fingers.

Henry blushed. Jason smiled.

"You're very pretty." he said looking straight into his eyes.

"Th-thank you." Henry stuttered. Was he actually getting feelings for Jason? He felt nervous all of a sudden. The need to make Jason happy. To impress him. His panties shifted.  

More students piled into the classroom, and class began. Mr. Crenshaw talked about the old Greek plays. Back then, women were not allowed in the theater, so men would dress up like women and play the part. Henry shifted a little in his seat. After first period, Jason showed Henry the way to their next class. He showed him an open seat that was next to his, and the school day continued. In every class there was a open seat around Jason. Henry was having difficulty figuring out a way to keep his distance from his supposed boyfriend. What if he just told Jason the truth? Then he might be able to go to school as a guy. Everything would be ok.

Before Henry got on the bus, Jason turned to him.

"So hows the new school?"

"Its ok I guess…" now seemed like the perfect time to tell him who he really was.

But before Henry knew what was happening, Jason hugged him passionately, his arms encasing Henry fully in a genuine hug. He instinctively put his own arms up and, to avoid looking awkward, put his hands flat against Jason's back. Jason finally started to pull away, after he slipped a piece of paper into Henry's hand.

"Text me," he whispered in his ear.

Jason left Henry standing there, breathing heavily. Why was Jason so good at arousing him? He walked onto his school bus with a shiver.




When he got home from school, he asked his aunt about the uniform situation.

"No one else wheres them. And Jason said that non of the faculty care if students wear them, so no one does. I totally stand out."

"Well," Aunt Rebecca began. "I guess its time to finally buy you some clothes. Come on. We're going to the mall."

They drove to the nearest mall and Aunt Rebecca immediately walked into the nearest female clothing store, which happened to be Victoria's Secret.

"I've made enough custom panties for you dear. You know, with the pocket. But you need some more bras."

She went all over the place, picking out bras and holding them up to Henry.

"Ok, you're a 32 A babe. Lets get you some variety."

After about thirty minutes of bra shopping, Henry had a brand new pink, black, white, baby blue, yellow, and red bra.

"Do I really need all these bras Aunt Rebecca?"

"Of course you do! If you're going to wear normal clothes to school, you're going to need all different types of bras to match those outfits."

"But we don't have the outfits yet."

"Exactly. So we just get a bunch of different kinds of bras."


After they paid for the new underwear, they continued to walk around the mall, popping in and out of various stores looking for clothes.

"Lets see. Its January, so it'll probably be cold for at least three more months. I think just getting the winter clothes will suffice for now. We can start with some jeans."

Henry walked into a dressing room with his aunt ten minutes later with an armful of jeans.

"Go ahead and try one of them on sweetie" his aunt instructed.

The first pair Henry put on were quite tight. The skinny jeans hugged his legs tightly, giving him a slightly claustrophobic feel.

"They're tight."

"Of course they are. They're supposed to show off your girlish body."

"I don't really have that much of a girlish body" he grunted, trying to put on the jeans.

"You're right. We might have to do something about that…"

"Huh?"

"Oh never mind. How do they fit honey?"



Henry eventually got five pairs of jeans, a new pair of cute sweatpants, a pair of yoga pants, numerous tops, sweaters, hoodies, and Aunt Rebecca had put in an order for a pair of chocolate colored uggs.

She declared that they were done shopping, having gotten Henry quite a number of new outfits.





The next morning Henry got up to see an outfit his aunt had laid out for him. He took off his pink footsie pajamas and shivered slightly. He stepped into the skinny jeans his aunt had brought him, shaking them gradually up his legs. He then put on one of his new bras, the pink one. It squished his chest into his tiny A cups again. Next he slipped into the tight yellow tank top that hugged his sides friendly, and finally put his arms through the warm sleeves of a baby blue hoodie.

Aunt Rebecca helped him with his makeup and teased his hair again. Then she brought him downstairs to the kitchen, where a banana and yogurt cup were waiting for him. Henry ate his breakfast carefully, trying hard not to spill on his new clothes. As he walked to the bus stop, his aunt stood in the doorway, wearing her pink bathrobe, sipping her coffee and smiling to herself. Henry hadn't seen the pill she had slipped inside the yogurt. But he would find out soon enough.
Henry goes to school and gets some new clothes.
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Finally the tg