It was around age 5 when Pauline began to start playing soccer. While she wasn't good at it, being rough with the other boys in her neighborhood was the first thing to cause her true joy. Eventually, she started to get really good at it, since she was the first kid on her block to start practicing by herself. By age 6 she was able to outplay 9 year old boys, which made them all quite jealous. In an act of pure anger, some of the older boys on her block decided to cut her waist length hair down to a pixie cut during a sleepover. However, this had the opposite effect as Pauline began to really like having short hair.
Not long after that she started demanding to get action figures instead of dolls, then she wanted pants and t shirts instead of dresses. By age 7, Pauline could have easily been mistaken for a boy, which is why, a month before school started Pauline asked her parents if she could become a boy. While her parents were shocked and somewhat confused about what Pauline even wanted, she somehow managed to convince them to start going by Jack, and shockingly, the neighboring kids were actually extremely supportive of his transition, since that would mean they were no longer getting beat by a girl in sports.
A week before Jack's 8th birthday, he had his first period. Unsurprisingly, this caused Jack an immense amount of dysphoria in addition to the pain periods can have at the best of times. This prompted Jack's parents to look into puberty blockers, which Jack took, ensuring his first period would be his only one. While Jack's female classmates began to develop curves, Jack stayed the same as he always had, and on his 12th birthday he began taking testosterone. During this time Jack had become an accomplished soccer player, but the presence of T began to kick his performance into overdrive. Not only would he lead his middle school team to be state champions, he was also the first person in his highschool to make varsity soccer as a freshman in 30 years, and the only one to ever become captain by his sophomore year. At this point, he had been living as a guy for 8 years, so most of his classmates didnt even know he used to be a girl. This caused mild issues for his romantic exploits. You see, Jack was pansexual (something not at all changed from his cis self) but when your average 90s highschool student, guy or girl, pulls down a guy's pants and sees a pussy instead of a dick, they begin to ask questions. Thankfully, Jack also had a killer tongue which led to him bedding cheerleader and chad alike. He ultimately got signed to a prestegious school on a sports scholarship, but did surprisingly well in his biology classes (he didnt become any dumber when he lost his dick after all). Ultimately landing him a spot in both the championship game 3 of 4 years as well as an internship at one of the most accomplished medical firms in the United States. Over the next 10 years, through a combination of hard work and seduction, he would crawl his way into a senior position of reasearch and development by the age of 34, while still maintaining an active sex life.
Back to the present, after wakeing up in bed at 6pm sharp from his post work power nap, Jack immediately went to his date with the CEO of Buchannon Pharmasuticals, Johnson Q. Buchannon. Using his silver tounge and his regular tounge, he managed to persuade Johnson into having sex with him, and for a 60 year old medicine heir he managed to be surprisingly proficent. When Jack woke up in his bosses bed the following morning to find....