A few weeks later

Tanya out her briefcase under her arm as she slid her keys into the lock. As she entered her modest home she placed her work things on the kitchen island and gazed upon her boyfriend who was sunbathing. It had been a few weeks since their last big fight. He left and she didn't hear from him for a few days. Eventually he called her. He apologized for being rude and inconsiderate. He gave her some line how him not being able to provide for her hurt his male pride and he exploded. She smiled to herself as she thought about what his “male pride” would think about the photos she made of him with the sexy feminine body of one of his favorite pornstars. That sense of power over her boyfriend made her vagina start to tingle with warmth and her cheeks began to feel flush.

Simon looked over from his lounger and saw his girlfriend had gotten home from work. He smiled and gave her a wave. After their most recent fight he was nervous that it was going to be the end of them. He had said a few harsh things. He thought they were true but he did deliver them in not the kindest ways. After he gave her some space he crashed at his buddy Calvin’s apartment. It was nice to have a few days away. He drank and he partied. He even tamed a little strange. “We were on a break right?” He thought to himself as he remembered that cougar with the nice cans that blew him that first night. He did enjoy his brief venture into single life but he also knew he didn't want to end a good thing. Tanya had gotten hot since high school but she still had the confidence of the fat girl she was. All he had to do was sweet talk her and he could pretty much crash at her house, eat her food and try to make it as an actor. Plus the regular sex was pretty great. When he saw that her dad produced that Heart Fire movie and that his production company was becoming one of the biggest in Hollywood he looked her up on Facebook. His awkward chubby friend had now become pretty hot. Not a 10 of course but a solid 8. He just so happened to reach out to her before their reunion and the rest was easy. He just wished that she would introduce him to her dad but that was only a matter of time. He needed to get to know her dad and get the inside track to star in one of his next productions. He smiled thinking about his future as the next Hollywood Heartthrob. Then it didn't matter what Tanya thought of him. He would have women throwing themselves at him. Thinking about all those women made Simon start to feel a little horny and he knew just the pics to look at. He quickly got up and entered the house. Tanya was talking on the phone so Simon gave her a loving peck on the cheek before he entered their bedroom and closed the door.

Tanya smiled as Simon snuck up behind him and gave her a quick peck on the cheek before heading into their room. She looked at him as her dad chatted with her on the phone. She noticed that his back was getting a little wrinkled from all that time in the sun. She should mention to him to wear moisturizer and that tanning can age his skin a few years.

“I am sorry to put this all on you sweetie. It isn’t.” Her dad pleaded from the other line breaking her from thinking about Simon's back.

“Oh no daddy it’s fine. I get it you loved mom and now you don't know what to do. You hate how lonely you are but it's hard to trust again.” She comforted her dad. He had called to check in and during their chat she could tell how sad he was and began probing for more information.

“Thanks hun. I just never thought that I would be dating at this stage in my life. I mean I am almost 50 for crying out loud. I just don't even know what to do. The women around here are pros. I am just an amateur.”

“Dad don't say that! You are a catch! You have a great job, you're in great shape, you're sweet, most women would jump at the chance to be with you if you let them.” All of this was true. Her dad looked great for his age, his company was producing hits and he was a good man. “Have you ever thought about online dating?”

“No...gosh that's a little weird right?”

“Of course not. Everyone is doing it now. You get to know someone before you even date them and if it doesn't work you just end it. No stress, just fun.”

“I don't know sweetie…..” an idea struck her. It was crazy but it may help her dad get confidence.

“Just try it. And if it doesn't work just delete it. I will even build your profile. What do you have to lose? And besides maybe we could double date one day!” Was this crazy enough to work?

“Fine, I will try it. Thank you sweetie...Wait are you dating someone?” Tanya had not mentioned to her over protective dad anything about Simon. She knew he wouldn't approve and was hoping that he would get a job first before she introduced him.

“No problem dad! And don't worry about that. This is about you! I will build it now and then email you the log info! This is exciting! I love you daddy!”

“Love you too sweetie.”

Tanya hung up the phone and sat down for a second as a plan started to form. Her dad just needed some confidence to get back out there. She knew that if a beautiful woman reached out to him and talked him up he would begin to believe in himself and have no trouble finding love. She would just need Simon’s help. She was never good at flirting; he could bring a male perspective and help her dad. She quickly entered her bedroom to ask Simon for help. As the door opened she saw her boyfriend sitting in their computer chair with his legs spread grasping hold of his not so impressive manhood. On the screen was what appeared to be the picture of a Latin milf in a green bikini with an oddly familiar face.

“I am so sorry!” Tanya cried out as she turned and closed the door. She almost couldn't control her laughter. Usually Simon masturbating would have made her self esteem plummet but this was different. Watching her boyfriend jerk off to an erotic picture of himself as women caused her pussy to feel warm again. Only this time the feeling was more intense. She went and sat back at the dining room table and in walked Simon, who was clearly embarrassed.

As Simon entered the room he began to feel nervous. They had talked about his masturbating. He knew it made Tanya self conscious and she didn't like it but he couldn't help it. There were just so many hot women out there. “I mean Baskin Robbin’s has 31 flavors for a reason” he thought to himself. But oddly Tanya didn't seem upset. She actually kind of seemed…...happy.

“I am so sorry babe! I just didn't know how long you were going to be on the phone, and I was feeling horny. So I just………”

“It's ok babe,,, I get it. “

“You do?”

“Yeah of course…” She knew this would be a big ask, so she thought it would be best to not start it with a fight. “ Actually I need a favor…”

“Ummm….ok….How can I help?”

“Well I just off the phone with my dad and you know how he has been struggling with getting back out there after mom left”

“Yeah?” Simon began to feel hopeful. This could be his opportunity to meet her dad and it almost sounded like she wanted him to help her dad pick up chicks. Thats a win, win.

“ Well I have a plan. What if a beautiful woman started flirting with my dad online. That would build up his confidence right?”

“Yeah, sure, but you can't guarantee that a beautiful woman is going to flirt with him. I mean what are you going to do, post his bank statement in his profile?” Simon said with a laugh that was just met by a glare from Tanya. "Sorry not funny.”

“Yeah….. But what I was thinking is what if we build a profile and talk to my dad on their. I know what he would be interested in and you know what guys like to hear it would be perfect. We build my dad's confidence and then the woman has to move and my dad doesn't get heart broken.”

Well that wasn't exactly what he had in mind and sure it was a little weird but it sounded easy enough. He could earn some more brownie points with Tanya, and get to know her dad a little more so when they finally met he could get on his good side. That actually gave him an idea.

“Sure, just on one condition.”

“What's that?” Tanya asked skeptically.

“At the end of this I get to meet your dad.” A smile crept across Tanya’s face.

“Of course!”