Apartment Sitting- Part 3

Apartment Sitting- Part 3
by RogerGirl

  Tiffany spent the rest of the afternoon getting ready for her date.  She had never been on a date as a girl and wanted to look good.  She was a little nervous because she was unsure how to act.  Having been on dates with both guys and girls as a guy was one thing, but she had no experience in taking the female role on a date.  She went to the closet and found a sexy black dress that came to mid-thigh.  She took a shower and spent extra time removing any body hair that may have grown back.  She got out and dried off, then brushed her teeth.  She returned to the bedroom and put on a strapless bra and matching thong.  She put on the dress then went to the bathroom to do her makeup.  She glanced over at some of the wigs her sister had bought for her before she grew her hair out, but decided to use her natural hair.  She put on a pair of 5" heels and grabbed a few things to put in her purse.  She went to the living room and watched some TV while she waited for Scott.

  Around six, she heard a knock on the door.  She opened it and saw Scott smiling at her.  He was wearing a suit and looked very handsome.  He told her how beautiful she looked and took her arm.  They took the elevator down to the garage and he drove them to a nice Italian restaurant.  Tiffany found herself enjoying the female role and found Scott to be quite the gentleman.  In the past, when out on a date as Tyler, even when with a guy, he would always be the more dominant one.  It felt nice being the one who was being treated and she decided this might not be her last date as Tiffany.

  After dinner Scott took her back to her apartment and since it was only nine, she invited him in for some dessert.  They sat talking and laughing on the couch for a while and soon Scott leaned in and kissed her.  Their kissing became more passionate and soon they were moving towards the bedroom.  As they made the way to the bedroom, she removed her dress and heels and let them fall in the hallway.  They reached the bedroom and Tiffany got in bed while Scott began to undress.  They were soon naked in bed and Scott's hands were all over her as he kissed her body.  He was about to penetrate her when they were interrupted by the buzzer.  Tiffany went to the buzzer to see who it was.

"Hi, Tyler," a familiar voice said, "it's mom.  Your dad and I were in the city for some business and we wanted to surprise you."

"Just a minute," Tiffany said as Tyler.

  She began to panic, but Scott told her to calm down.  He helped her removed the breasts with adhesive remover, while she took off the vagina and used some wipes to remove all her makeup.  She tied her hair back in a ponytail and put on Scott's clothes, since they were the same size.  He buzzed them up and hurried to the living room while Scott hid in the bedroom.  He noticed the dress and heels and tossed them behind the couch.  

"Knock, knock," his mom said as they walked in.

"Mom, Dad," Tyler said as he greeted them, "I wasn't expecting you to visit."

"Oh, this wasn't planned," his dad said, "but we knew this was your first time living on your own and we wanted to see how you were doing."

  They talked for quite a while about how his week was going and how he was spending his time.  Soon it was almost midnight and his parents were about to leave.  As he got up to say goodbye, he noticed his mom looking at him strangely.

"Is that lipstick on your face?" she asked.

"Huh, no probably just sauce," Tyler answered hesitantly, "I had spaghetti tonight."

"No it looks like lipstick," she said moving closer to him and noticing the dress and heels behind the couch, "and what are these doing here?"

"I think I know what's going on here," his dad said.

"You do?" Tyler asked nervously.

"Yes," his dad said, "our son is on a date."

"Oh no," his mother apologized, "I'm sorry, we didn't mean to intrude."

"It's OK," Tyler said relaxing.

"Where is she?" his dad asked, "Is she as hot as that last girl you dated?"

"Oh, I don't know if she wants to meet anyone right now," Tyler said, "she might be a little embarrassed."

"Don't worry," his mom said, "I just want to apologize to the poor girl and give her her clothes back."

  She got up and went to the bedroom door as Tyler tried to stop her.  His mom knocked on the door and the door opened slightly.  A hand reached out and took the dress and heels.  The door shut again and a few minutes later it opened again.  Out stepped a sexy girl wearing the dress and heels.  Her long brown hair and makeup was messed up, but everything else seemed perfect.  Her nails were painted in a french tip, her breasts were large and firm, and her long legs were smooth and hairless, as was her entire body.  

"You must be Tyler's parents," she said in a naturally feminine voice, "I'm Sylvia Scott."

"It's nice to meet you," Tyler's dad said.

"Yes it is," Tyler's mom said, "Oh your makeup is a little smudged, dear."

"Thanks," Sylvia said as she picked up the purse on the table and went to the mirror to fix her makeup.

"Well, we'll let you finish your date," Tyler's mom said, "It was nice to meet you dear."

"Nice job son," Tyler's dad whispered to Tyler as they both left.

  Tyler watched as they went down the elevator, then shut and locked the door.  He turned to Sylvia, who was standing by the couch.

"Wow," Tyler said looking her over, "how did this happen?"

"Well, that's one of my secrets," Sylvia said, "back in school I used to get stuck playing girls in a lot of the school plays since I was generally the smallest and it was an all-boy's school.  I got pretty good at doing makeup, talking like a girl, and all that.  When I was stuck in the bedroom for three hours I transformed myself into Sylvia just in case your parents found the clothes.  I know you'll come out to them when your ready, but I didn't want to force the conversation by them finding a naked man in the bedroom.  It did suck having to remove my body hair though, but hair will grow back."

"Thanks," Tyler said hugging her, "someday I'll tell them, but I definitely wasn't ready to have that conversation tonight."

"Well, I'm gonna get out of these clothes," Sylvia said.

"Wait," Tyler said grabbing her hand, "I know I'm gay, but seeing you as a woman is kind of hot.  Do you think I could get to know Sylvia a little better?"

"I don't know," Sylvia said, "I may have dressed as a girl in school, but I never kissed or dated any guys.  I like women, but was drawn to you because you look hot as a girl."

"Please," Tyler said, "I let you take me out as a girl."

"Fine," Sylvia said, "I'll try it."

"OK, can I take you out as Sylvia tomorrow night?" Tyler asked, "Since you have the day off you can spend the day getting ready here while I hang out at your place."

  Sylvia agreed and Tyler grabbed some boxers and stuff from his suitcase.  He kissed her on the cheek before leaving to go to the apartment across the hall.  Sylvia stood alone in the apartment wondering what she had gotten herself into.