The Orphan Part 5

Henry woke up the next morning alone. His aunt was already up, and let him sleep in. He took off his pajamas, put on his robe and slippers, and walked downstairs.

"Are you ok Henry?"

"Ya. I just had a bad dream."

"Well," she said, giving him one of her strong but comforting hugs, "its all better now baby." she kissed him on the forehead and smiled.




Henry and his aunt hung out around the house for the rest of the day. After dinner that night, Aunt Rebecca turned to him.

"Well, it's almost seven. The party starts at seven thirty. Let me get ready, and then I'll help you."

Henry went up to his aunt's room ten minutes later when she called him. She was wearing a teal blue dress and matching heels, her attractive blonde hair was curled like always, and she had a vibrant red lipstick on.

"What do you think Haley?" she said to him.

He recognized the emphasis on her last word, and answered accordingly. "So pretty Aunt Rebecca!"

"Very good! You'll do fine tonight. Now, let's get you ready."

His aunt sat him down in front of the mirror again, and went to work. She styled his hair into a pixie fashion again. Then she applied the face and eye makeup, ending with a faint pink lipstick. After the makeup was done, Aunt Rebecca went and found him his outfit for the evening. It was a short green dress, and matching high heels.

"This is New Years Haley." his aunt said, in response to the look on his face. "You must look presentable. Now strip."

He took off his robe and slippers, standing there in his diaper and bra.

"Oh right. I forgot about the diaper. Are you a big girl? Tonight is your test. If you stay dry for the whole night, you may wear big girl underwear again."

"I can handle it." he said firmly.

"Ok. Here you go." she handed him a pair of black lacy panties and a matching bra. "Your pink bra won't go well with the dress," she explained.

Henry put on the black bra and fastened it. Again it produced two perky little A cups. He slipped on the panties. He had forgotten how good they feel. The soft lacy material caressed his legs as he pulled them up, finally letting them snugly fit themselves around his waist, cradling his genitals in black lace.

"Much better," his aunt said approvingly. "I added some material to the panties on the inside. There's a small pocket that runs down the front. You can fit your male parts in there, and they'll hide them even if you get excited."    

Henry fished around in the panties until he found the pocket. He slid his penis into it and pushed it down all the way, causing his membrane to slide down and wrap around to his butt. His front was now completely smooth, showing no trace of his manhood.

"Here," Aunt Rebecca said, handing him the dress.

Henry stepped into the dress and pulled it up. It was snug around his waist. He put his arms through the straps and adjusted the front to fit nicely around his breasts. Then he stepped into the shoes and almost fell over. They were really steep.

"Careful," his aunt said. "They're a little taller than usual. I don't want you snapping them. Practice walking in them while I get the finishing touches. "

Henry practiced walking in the heels. He found it easier to keep his balance when he swung his hips and moves his arms. His aunt came back and handed him a green handbag and a black cardigan. She was also wearing her own cardigan over her teal blue dress.

"Hold out your arms," she instructed, holding the cardigan out for him. Henry slipped his arms through the soft sweater, and he shuddered with the sensual feeling. Boys never got to wear clothes this comfortable.

"I like it," he said, as his aunt buttoned up the front.

"I'm glad," she said. "It looks very cute."

Henry blushed a little. His aunt noticed, and kissed him softly on the cheek. "Here," she handed him the green handbag. "A good girl always has her handbag when she goes out."

Henry looked inside the bag. There was pepper spray, extra makeup, a small mirror, and…

"Tampons?" he asked.

"Yes."

"But I don't have -"

"Oh I know that. But it helps seal the image. If someone sees those, they won't question your disguise. Now come on Haley. We're going to be late."

His aunt grabbed his hand and led him downstairs and out to the car. It was chilly out, and he was even more grateful for his soft sweater, but his legs were completely exposed. He shivered as he got into the passenger seat of the car. His aunt turned to him.

"You smeared your lipstick? Honestly how did you manage that? Use the mirror in the visor and fix it."

Henry pulled down the visor and took the lipstick out of his handbag. He carefully applied it to his lips, puckering as he did so. He looked very feminine, concentrating on making sure his makeup was perfect. Aunt Rebecca smiled to herself.

The roads were still very icy, but they weren't going very far. As they pulled into the drive, they heard women chatting and giggling from inside the house. They got out of the car and walked to the front door. It was windy, and Henry had trouble keeping his panties from showing. His aunt rang the doorbell, and Sharon came to greet them. She was wearing an adorable maroon dress and her blonde hair was bouncing with volume. She smiled brightly when she saw them.

"Becky! I'm glad you could make it!" she hugged Aunt Rebecca once she got inside. "Hello Haley. How are you?"

"I'm well thanks." Henry smiled back at Sharon.

"Here, let me take your coats," she took their sweaters, and Henry felt a little sad. It was so soft and warm. "Come on in!"

They walked into the dining room, where at least a dozen women chatted and gossiped. Henry didn't know it was going to be an adult party filled with pretty women. His panties shifted a little as its contents changed size.

"Everyone, you know Becky, and this is her niece, Haley."

"Hello," he said, hoping no one would discover him.

The women said hello and some even complimented on his appearance.

"Such a pretty girl."

"I love your short hair."

"Are you single? My son is desperate."



The party continued through the night. He didn't talk much. He munched on a few crackers with cheese while all the other women drank red wine and progressively got louder as the evening progressed. Then, at about 10:30, two teenage boys came into the room and grabbed some food. Sharon shoo'd them away.

"Aw come on mom, we just wanted some crackers," one boy said.

"Go back upstairs, this is an adult party."

Sharon's son briefly glanced at Henry. He couldn't tell if it was because she was pretty or because she was allowed at the "adult party". Sharon noticed and looked at Henry.

"Haley have you met my son, Jason?"

Jason turned to her and said hello.

"Hi" Henry replied, smiling a little.

"Jason why don't you take Haley up to your room? I don't think she's enjoying herself down here."

It was true. He hadn't talked to anyone for a while, and was frankly getting quite bored.

"Ok," Jason said, a little sheepishly.

Henry followed Jason and his friend upstairs to his room. Once they all got inside, Jason shut the door.

"So… you're name is Haley?"

"Yes," he said, trying to put on his best baby doll voice. "I'm Rebecca's niece."

"And, which one is Rebecca?"

"The one in the teal dress with the curly blonde hair."

"Oh right. I've seen her before. She's friends with my mom. Are you staying with her or something?"

"Ya… my house burned down and I was the only one who made it out…"

"Oh…. I'm sorry…." Jason didn't know what to say.

"Its ok," Henry said. "May I use your bathroom?"

"Sure. Its out the door and to the right."

Henry walked into the bathroom and shut the door. Jason seemed nice. But he didn't really know what he was supposed to say. Henry could probably think of something that they had in common. But Haley couldn't. He unstrapped his dress and let it fall to his feet. He then slid off the panties and sat on the toilet. He couldn't wait until this night was over. After he was done, he pulled up his panties again, slipped his parts into the front pocket, and slid the dress back on. Henry looked at himself in the mirror. He did look kind of cute. The thought of it made his penis grow a little.

He walked back outside and was about to open the door to Jason's room when he realized they were talking about him. He stopped and listened at the door.

"Come on man you gotta get with her."

"I don't know… I think I'd feel guilty afterward."

"Her family is dead so she probably wants to live a little, she's living with her aunt who probably doesn't care what she does, she's shy, and totally hot. It'll be easy."

"Thats the problem Kyle. I feel like it wouldn't be real."

"You gotta do something Jason! Come on, its New Years. Make your move at midnight."

"I'll think about it. If we hit it off, I might do it. But I'm not gonna push it."

Henry took a deep breath, made a mental note to watch out for Kyle (who seemed like bad news) and opened the door.

"Oh hey…" Jason said suddenly.

"So… what do you guys wanna do?"

"I don't know…you?"

"Well," Henry said honestly. "I wanna get out of these heels."

"Ya, sure. Here sit on the bed." Jason stepped to the side to let Henry get to the bed. He started to move towards it, but he stepped in a shirt that was in a ball on the floor. His heel got caught, he spun around, something snapped, and he fell. Jason quickly caught him by his waist.

"Whoah are you ok?" he asked quickly.

"Ow. I think… I think I sprained my ankle."

"Sit on the bed, Kyle can you sneak downstairs and get some ice?"

Kyle left the room and Jason kneeled down next to the bed where Henry was sitting.

"Does it hurt?"

"A little," he said. "Can you help me get out of these shoes?"

"Ya," he took Henry's shoe off of his good foot, and slowly slid the other one off the sprained one.

"I like your nail polish," he said

"Oh thank you," Henry replied, looking down at his sparkly pink toes. "My hand nails are the same," he held out his arms and pointed his wrists down, extending his fingers and showing off his nails in a girly way. What was he doing? Showing off his nails? He wasn't actually a girl! But he felt the need to impress Jason...

"Pretty," Jason said, staring at the nails.

Kyle came back with the ice and a small towel. He helped Jason wrap the ice in the towel and press it against Henry's ankle.

"I got it," Henry said, moving towards the towel.

"Its ok," Jason said the words calmly, holding the ice in one hand firmly and holding Henry's leg gently in the other.

Henry pulled back, letting Jason hold the ice.

"Better?" he asked, looking up at Henry.

"Yes," he said, looking at his doctor and smiling.

Jason smiled back.