Apartment Sitting- Part 1

Apartment Sitting- Part 1
by RogerGirl

  Tyler and his sister Jennifer were always very close, despite their six year age difference.  Growing up they had confided in each other for everything and shared their closest guarded secrets with each other.  Many of these secrets they had not even shared with their parents or closest friends, but felt comfortable sharing with each other.  As a teenager, Tyler had shared two big secrets with Jennifer.  First, Tyler was gay.  He hadn't told anyone else this and would often go out with girls at his school to avoid suspicion.  He had a few short-term girlfriends and had even had sex with a few girls, but he secretly longed for the day when he would no longer have to hide behind a facade.  His other secret was that he enjoyed crossdressing.  Whenever his parents were away for a day or more his sister would help transform him into a girl.  While he did not want to become a girl, he enjoyed learning how to put on makeup and trying on sexy clothes.  Unfortunately, he was unable to remove his body hair since he was afraid of how his parents or people at school would react.    

  While Jennifer lived close to home throughout the time she went to college, when she graduated she moved to the city.  This was both good and bad for Tyler.  It was bad because Tyler no longer had any clothes or makeup to put on and because he lost his closest confidant.  It was good, however, because on those occasions when he would make the four hour drive to his sister's apartment, he was able to do things he could never do back in his home town.  Jennifer often helped him meet guys and he would go out on a few dates with the guys she introduced him too.  He was also able to crossdress for longer periods of time, although he still couldn't remove his body hair until he finished high school.  Jennifer taught him everything he needed to know about acting and appearing as a girl, and he eventually picked the name Tiffany for his female persona.  

  Things went on this way for a while until the summer after he had turned 18.  Tyler's sister, Jennifer, was spending a week in New York over the summer and he had just graduated high school.  Before going on her trip, Jennifer got her parents' permission to let Tyler apartment sit for her while she was away. Their parents thought it was a good idea since it would teach him some responsibility and prepare him for his move to the city when he started college in the fall.  On the day it was time to leave, Tyler packed a small suitcase and said goodbye to his parents.  He didn't need much clothes since he was planning on spending most of the week as Tiffany.  He made the drive to the city and buzzed his sister when he arrived.  She let him up and he took the elevator up to her floor.  When he got to her door she opened the door and he saw a guy coming out of the apartment across the way.   

"Oh, hey you must be Tyler," the guy said, "your sister told me you'd be watching her apartment while she was gone."

"Yes," Tyler said as he shook his hand, "I just finished high school and will be starting college here soon.  She thought it'd be a good idea if I got used to living here before the big move in the fall."

"Oh, sweet," the guy said, "my old alma mater.  I'm Scott Silvers by the way, if you need anything while you're here, just let me know.  I help your sister out around the apartment all the time."

"Yes," Jennifer said, "he made my first few weeks here a lot less stressful."

"OK," Scott said, "I got to go to work.  See you around."

  Scott left and Tyler watched him as he went down the hall.  Jennifer smiled when she realized her brother had a crush on him.

"You like him don't you?" she asked as they went into her apartment.

"Yeah, he's cute," Tyler said, "too bad he isn't gay though."

  Before leaving, Jennifer told Tyler to make himself at home and that he was free to try on anything in her room, except for her underwear, which he had his own. As she left, she told Tiffany to have a good time.  Tyler smiled after she left and anticipated an entire week as Tiffany. He went to the bathroom and removed all his body hair, washed his shoulder length hair, and put on the prosthetic breasts his sister had got him. He put on a new bra and bikini panty set, tucked his manhood back, and put on one of Jennifer's casual dresses. He walked over to the closet and began looking through all her clothes. He put his hands on his hips and wondered to himself what he would try on first.

  He put on a black skirt and blue blouse and a pair of heels.  He climbed onto Jennifer's bed and rubbed his soft legs and thighs together.  He had never been able to remove his body hair before, and was enjoying the feeling of his soft hairless skin.  As the day went on he began to get hungry, so he went to the kitchen to find something to eat.  In her hurry to pack for the trip, Jennifer had forgotten to buy groceries so the fridge and cabinets were pretty much empty.  Tyler went back to Jennifer's room to change and go to the market.  He didn't want to go back to his male clothes, but was not yet ready to go out in public in such a short skirt.  He put on a t-shirt and a pair of flared jeans with a pair of tennis shoes.  He packed his money, cell phone, keys, and a few other things in a purse and cautiously went to the door.  After making sure the hallway was empty, he took the elevator downstairs.  

  He drove a few blocks until he found a small grocery store.  Not really feeling comfortable going out as a woman, he wanted to make sure he had enough groceries to last the week.  He bought snacks, vegetables, meat, deli items, bread, cheese, milk, juice, water bottles, and soda.  He also bought laundry detergent, softener, makeup wipes, toilet paper, and anything else he might need for the week.  After paying for his items, he went to his car and loaded the groceries.  As he drove home, he thought about his experience.  No one at the market noticed he was really a guy and a he caught a few guys checking him out.  Even when he spoke in the female voice he'd been practicing no one gave him any weird looks.  He began to feel more confident and decided he might make some more short trips out as Tiffany.

  He got back to the apartment garage and began unloading the groceries from the car.  He had a lot of bags and began to realize he would probably have to make more than one trip to get everything.  He was about to close the trunk when he heard a man's voice behind him.

"Oh, let me help you with that," a man said.

"It's OK I've got it," Tyler said hoping the man wouldn't see him.

"No, let me help," the man said coming closer.

"Thanks," Tyler said trying to cover his face.

"You're welcome," the man said.

  The garage was dark, but Tyler recognized the man as Scott when they got toward the light near the elevator.  They entered the elevator and Tyler realized he couldn't hide any longer.  Scott would know it was him when they reached the apartment.  He slowly uncovered his face as the elevator doors closed.

"Tyler?" Scott asked in surprise.

"Yes, it's me," Tyler responded afraid of how Scott would react.

"Wow, you look just like your sister," Scott said, "Why are you dressed like that?"

  Tyler explained to him how he enjoyed crossdressing and how his sister had let him use her wardrobe for the week.  He decided not to tell him he was gay, since that might be too much to reveal to someone he just met.  They reached the apartment and carried all the bags inside.  

"Hey, don't worry," Scott said as he was about to leave, "I won't tell anyone about your crossdressing.  You do look pretty cute as a girl though.  Do you have a girl name?"

"It's Tiffany," Tyler responded shyly.

"Well, it's nice to meet you Tiffany," Scott said shaking her hand, "if you need anything I'm right across from you."

"Thanks," Tiffany said as she watched him walk into his apartment.

  She shut the door and smiled.  For the first time, she began to think of herself as a girl.  While in the past she had merely thought of herself as a boy in women's clothing, after realizing she could pass as a girl and that she was attractive as a girl, she decided that as long as she was Tiffany she would only refer to herself as a female.  She went to the bedroom and changed into a pair of sweat pants and a tank top from Victoria's Secret.  She went to the kitchen and fixed herself a quick dinner, then watched some TV.  That night, she fell asleep in front of the TV, exhausted from the day she had just had.