Apartment Sitting- Part 4

Apartment Sitting- Part 4
by RogerGirl

  Tyler woke up the next morning in Scott's apartment.  While he was disappointed that he wasn't going to be able to dress as Tiffany today, he was really looking forward to the date.  He wanted to find out if Scott liked him as Tyler and not just as Tiffany.  He didn't want to become Tiffany full-time and wanted to find a guy who liked both sides of him.  He knew Scott would feel uncomfortable going out on a date with him as two guys, so he wanted to try taking him out as a girl to work him up to a date as Scott and Tyler.  As he went to the kitchen to have some breakfast, he wondered how Sylvia was doing next door.  

  Back in Tyler's sister's apartment, Sylvia had woken up and was looking at herself in the mirror.  She brushed out her wig and looked at her body.  She was wearing a short night dress that came to mid-thigh.  She had known for a long time that she was bisexual, but had always been afraid to tell anyone or to act on it.  When she met Tyler she had found him attractive, but was afraid to make any move.  When she finally met him as Tiffany though, she knew she had her opportunity to take Tyler out.  She decided that since Tyler had been a good girlfriend for her when they went out as Scott and Tiffany, she would be a good girlfriend for him now that she was the girl.  She took off the wig and got undressed to take a shower and start getting ready for their date.

  Around six in the evening, Tyler put on a pair of socks and boxers and one of Scott's best suits.  He tied his hair back in a ponytail and went across the hall to pick up his date.  He wanted to make the date special, so he made reservations at a nice French restaurant he had found.  He knocked on the door and when the door opened Sylvia was standing before him wearing a short blue dress and 5" heels.  Her brown wig perfectly framed her expertly made up face and she was carrying a blue purse that matched her dress.  While Tyler had no interest in women, seeing the guy he liked looking so hot as a female was definitely turning him on.  

"You look amazing," Tyler said.

"Thanks," Sylvia said nervously.

  Tyler took her arm and they went to the elevator.  He drove them to the restaurant and made sure he was the perfect gentleman.  Like himself the night before, he noticed Sylvia was a little uncomfortable in the female role.  As the night went on, however, she began to loosen up and have a good time.  After dinner they walked around the outdoor shops for a while then drove back to the apartment.  Sylvia invited Tyler inside and they sat on the couch and talked.  After the night she just had, she knew she was finally ready to tell Tyler her secret.  

"There's something I need to tell you," she said, "I've known for a while that I'm bisexual, but before I met you I've been afraid to act on it or tell anyone.  When I met you as Tyler I thought you were cute, but was afraid to do anything since I thought you were straight.  When I saw you as Tiffany the next day I decided I would finally make a move.  I had a good time taking you out that day and was excited when you told me you were gay.  Now that our roles are reversed, I'd like to get to know you better as Tyler."

  She leaned in kissed him.  It was her first kiss with a guy and she began to kiss him more passionately.  Tyler was also enjoying the kiss.  One thing he did like about women was how soft their bodies were and he was always turned off when he tried to get intimate with a guy and found he had a hairy body.  He ran his hands over her soft legs as they continued making out.  Soon they began removing each other's clothes as they made their way to the bedroom.  Soon they were naked and this time they weren't interrupted.

  For the rest of the week, they had sex as Tiffany and Scott, Tyler and Sylvia, Tiffany and Sylvia, and on the last day they finally went out as Scott and Tyler for the first time.  When the week was over, Tyler's sister returned and they told her all about their week.  They both trusted her and were glad to share their new relationship with someone.  Tyler kissed his new boyfriend goodbye and returned home.  When Tyler started college in the fall, they resumed their relationship in secret.  Whenever one of their parents came to visit, the other would become a woman and spend the day as the other's girlfriend.  When Tyler was in his third year of college he moved out of the dorms and into Scott's apartment.  Scott had recently told his parents he was bisexual and introduced Tyler as his boyfriend, which meant Tyler would no longer have to dress as Tiffany when they came to visit.  Scott's parents were more liberal than Tyler's and quickly accepted their son's relationship with Tyler.  They were a little angry though that he had waited so long to tell them.

  One day Tyler's parents came to visit and he decided to finally tell them.  He was planning to propose to Scott soon and didn't want to force him to dress as Sylvia every time he was around the family.  Tyler had stopped dressing as Tiffany after Scott had come out to his parents and no longer had long hair.  He would dress on occasion, but since he started working he had less and less time to dress as Tiffany.  He had returned to the Tyler he had been back in high school.  He wasn't sure how his parents would take it, but he was tired of pretending to be something he wasn't.  He had a nice job and was seen as the cool guy with the hot girlfriend by his friends, family, and co-workers.  While he could easily continue with this life, he knew it wasn't fair to Scott.  Scott had been dedicated to his job and didn't have a lot of friends other than Tyler and Tyler's sister.  Although he hadn't come out to anyone other than his parents to protect Tyler's secret, he had lost his job recently and was stuck as Sylvia the entire week Tyler's parents stayed with them.  After losing his job, he had grown his hair out and no longer wore a wig.  One day while Tyler's parents were out, Tyler overheard Sylvia talking to his sister as he was returning home from work.

"I know this is important to Tyler," she said, "but I need to start going on job interviews soon and I can't do that as a woman.  All I have is Tyler, but I don't know if I can continue this relationship.  I have to dress as a woman around all of Tyler's friends, co-workers, and family.  The only people I can be open with are you and my parents.  I just want to live a normal life as a guy.  Maybe even find a girlfriend and just make some of my own friends."

  Tyler watched from behind the door as his sister hugged her and saw tears on Sylvia's face.  He went out for a while and took a walk.  He knew Sylvia was right.  Scott had given up his life to be with him and he was forcing him to be a woman to avoid coming out to his parents and everyone else around him.  He returned home and found Sylvia helping his mom make dinner.  

"Hi babe," Sylvia said as she went over to kiss him, "your mom was teaching me her pot roast recipe."

"You're a lucky man," Tyler's dad said from the couch, "I hope you hold onto that one."

  Tyler grabbed a beer for him and his dad and went over to the couch.  His sister came in a little while later and greeted them all, but her attitude toward Tyler was a little cold.  At one point she asked Tyler if he could help her get the dessert from her apartment and when they got there she shut the door.

"I know I've promised to keep your secret," she said forcefully, "but it has been six years.  Scott has given up everything to be with you and you owe it to him to make a little sacrifice.  I will never say anything to anyone, but if you don't want to lose him I suggest you make a decision.  You always tell me how you hate living a lie, but as nice a couple as you and Sylvia make, you know it's all a lie.  You owe it to Scott and yourself to start living the truth."

"You're right, sis" Tyler said, "Tonight is the night I end this.  Mom and dad leave tomorrow and I'm not going to keep putting it off any longer."

  They grabbed the pies and returned to join the others.  They all sat down for dinner and were talking about the usual subjects when Tyler interrupted everyone.  

"There's something I need to say," he said nervously as they all watched him, "I've been putting this off for too long and I can't put this off any longer."

  His parents smiled at each other and he assumed they thought he was going to propose to Sylvia.  They had been dating several years now and his parents had been wondering when he would propose to her.  While Tyler did plan to propose, that wasn't the announcement he was about to make.  Nervously he searched for the right way to tell them that he was gay and that Sylvia was really his boyfriend Scott.