Girlfriend's Daughter, What if?

The story so far.

Bailey Andrew Smith had been coasting through life the last few years, he was enjoying much of it or at least that was what he told himself. The **** of both of his parents, and in connection to that his position running a store they owned had hit him hard. He was never one to be very open with his feelings, so while his girlfriend, Amanda Best, or Mandy as he enjoyed calling her, was willing to listen, he just wasn’t open to talking about it.

Bailey was a small man, standing at five foot six with a slight build. The height he had inherited from his father, but unlike the barrel-chested man, Bailey was slim much like his mother. Despite his small stature he had found himself hooking up with a tall blue eyed, blonde woman that was more than a few years his senior.

Amanda was a knockout and age didn’t matter to him in the slightest when he set his eyes on her. He was currently twenty-five to her, a young looking thirty-nine. Though at this point they had been together for a handful of years. Benign with his Mandy was akin to hitting the jackpot over in Vegas. Amanda was not just a pretty face; she held a position with Mega Corp, one of the largest companies on the planet and had worked her way up to being the head a department, with both accounts payable and receivable reporting to her at the Nevada branch. He thought they had a great relationship, and despite the age difference they were fucking constantly, her always saying how he made her feel so much younger.

Things changed when she started pushing for a promotion, Bailey was a hundred percent behind her, mostly because he wasn’t working or really looking for work. His girlfriend's salary meant the extra hours weren’t paying off monetarily in the present, but they thought it would in the future. Things got tight money wise and with her working so many extra hours the constant sex lost the word constant. He wouldn’t even consider the word consistent or regular to be an apt description.

In one of his less than moral decisions Bailey had told Mandy how he needed money for a job placement company that offered training. He in turn used that money to hire an escort or two to keep himself satisfied. Telling himself that Mandy knew he loved her, but she also knew he needed sex and if she wasn’t going to provide it, then he would find it elsewhere. It wasn’t like he was having a relationship with someone else, or so he reasoned.

A misunderstanding at Mandy’s office, where one of the company's executives mistook a picture of Bailey with his longer blonde hair and braces, something he only recently had removed, as her daughter. Amanda had worked so hard for the promotion and while she didn't know the executive Derrick Connors well, she was afraid correcting him after the mix up could cause problems. Talking to her older sister, Megan, they considered using Becky, Megan’s daughter for a stand in, but the plan quickly changed.

Back at home, in the apartment that Amanda and Bailey shared, the short man had been caught with a red headed escort he had used more than once by Megan when she had come by. The woman didn’t care much for Bailey and had almost used his traitorous act to get him out of her sister’s life. The thing was, Amanda was in a tough position seeing the scrawny man without his shirt on. She had an idea on how exactly the mix up with the picture of Bailey being a teen girl was going to become at least a temporary reality. A decision that meant his life was going to change drastically, though no one knew exactly how much till later. For him, being without a job, or really any place to go it was either do as the cruel and insane woman said or face the woman, he loved about what he had done. It wasn’t as big of a deal to him, but he knew Mandy wouldn’t agree, doubly so when she had Megan whispering poison into her ear about him.

Amanda thought the idea was crazy, but both her older sister and her boyfriend were on board with him pretending to be her teenage daughter for a company picnic. With Bailey’s stature and youthful appearance, some clothes and makeup the dolled up young man had been passing. Bailey had gone along with the insane idea only because Megan was blackmailing him, but the one day of pretending to be his girlfriend’s daughter at a company picnic soon turned into a week and then into a summer as the people they needed to fool stuck around.

Bailey Andrew Smith had gone from twenty-five-year-old man, unemployed boyfriend to Amanda Rose Best to Bailey Ann Best the eighteen-year-old daughter of the same woman and thanks to Megan he had gone from acting the part to acclimating to it.

One of the people and a big reason behind his disguise was Candace Ann Connors, the daughter of one of the high-end executives at Mega Corp. Bailey had started off needing to keep the teen company at the picnic while they were in town and over time that relationship had transformed. The extroverted girl had adopted who she believed to be a shyer girl as a friend and over the weeks they had been together had grown close enough that she loved Bailey like a sister, insisting that they really would be once their parents got married. Candace or Candi, as she liked to be called, had wanted to make plans like in the old parent trap movies to get their parents together. While Bailey tolerated her schemes, knowing his girlfriend was just playing a part like he was. Soon the Connors would be going back home, the sooner the better far as Bailey was concerned. He could appreciate Candi, she was kind in an innocent way that made him fell like he needed to be protective of the girl. She was pretty, though he put a mental line in the sand at that thought, knowing no good would come of it. Still the eighteen-year-old girl had grown on Bailey, she had shown him what real friendship was like and soon considered the teen girl who was a lot to handle not just a friend, but a best friend.

The Best family and the Connors had been on more than a few adventures, most of which Bailey was wishing Mandy, or Mommy as he was calling her now, wasn't so cozy with Derrick, the father to Candi. He had once tried talking to her about an open relationship, a conversation that happened long before he had ever put a skirt on. That conversation had not gone well, but now it was happening in a way he did not appreciate on any level. His girlfriend, the woman he loved, was sleeping with this other man, while he had to pretend to be some air headed boy crazy girl. Bailey had somehow even ended up the girlfriend to a boy and double dating with Candi. All of that was just the tip of the iceberg for how deep that horrible rabbit hole went far as Bailey was concerned.

Over the summer Candi was having something of a sexual awakening, she was more than a little naive about things in that realm but was having great fun with the fact that her best friend, while more than a little shy at times, had the experience she lacked, or so she believed. During her first week in Nevada their families had gone to a water park and it was in one of the changing rooms that she had learned something about herself. Candi had found herself in a situation right out of something she would expect to be in some rated R movie with Bailey, her and a handsome lifeguard. Topless Bailey had given the young man a boob job, rubbing his dick between her breasts.

The young twenty something year old had no idea the breasts were fake, the life-like quality doing their job. When the lifeguard had asked for her name Candi hadn’t thought about the answer really, just gave him her name. The man mistook the pretty blonde’s answer, taking it as if she was saying Candi was the girl pleasing him and when he had called out her own name while Bailey played with his cock it had turned her on more than she could have imagined. That had been just one new experience for her that summer and right now she was trying to convince her friend to participate in another.