Chapter 26

Holding the small pink book in his hand, Liam slid it into his purse after having to make another mark when he refused to get in Miss Megan’s SUV when she had told him who would be babysitting him, like him a twenty-three-year-old man needed a babysitter, but his life was vastly different than any other now. Last night he had stood in the corner saying how he loved his Daddy and how his name was Leah Megan Summers, and had to do it for about an hour. That was the punishment, but having to put on tight yoga pants that seemed to enhance his rear, a sports bra and the wedge heeled sneakers for exercise, following along to a yoga video seemed worse.

Daddy… his brother had mentioned that if he didn’t think she… it was so annoying to be referred to constantly as a female when they knew the difference. He thought, his brain getting off track of the threat he had been given. If he didn’t do his best at yoga, he would enroll his daughter in the heartbreak heels classes online. It was billed as a women empowerment class for dancing in heels, but both of them had watched the videos online. Showing women dancing sexily, flipping their hair as they moved around in a way made to entice men. Then Chuck had made him go to bed wearing the heels he had been in most of the day.

He had laid there wearing lingerie and heels to bed, thinking he at least got out of touching the dildo when he came back into the room, flipped the light on and set up his phone to video the oral practice. He hadn’t escaped anything he had thought, but now sitting in Miss Megan’s SUV he thought a little differently. Liam knew he got out of one big thing, his brother never actually saw him sucking on a dildo, moaning and acting like he loved doing it. Dad… Chuck never saw him jerking off, and then wiping his cum on that same dildo and putting it back in his mouth. He had the video, but considering he didn’t say anything, he hoped that he didn’t watch it and never would.

The day with Miss Megan was similar to other days, he did his oral practice in the morning and then in the afternoon. It had not gotten any easier, his jaw was still sore after, as was his will to ego. Doing that was by far the worst activity he had to endure, next to that the walking practice to make sure he had the gait of a girl on a catwalk was nothing. She still made sure he stopped to inspect his reflection in the hallway mirrors, now two were hung. Miss Megan had even put a makeup mirror on the kitchen table as he sat there drinking his shake.

Liam had done his best to ignore it, but anytime he caught his reflection he had to primp. It was ridiculous, but he played along eagerly. Miss Megan had even complimented him on how well he was behaving, letting him spend a good part of the afternoon practicing the saxophone in the backyard. He felt ready to break; it had been less than twenty four hours since he promised himself he would act happy and eager to foil her plans, but hearing the compliment made a genuine smile come to his face. By now he had lost his job, without a cell phone he had no way to confirm that, but he was positive. Miss Megan, on the other hand, had to keep running off for a meeting or doing work while watching him. So when she sent him off to do something he actually liked doing he knew she wasn’t getting what she wanted out of him anymore.

Or so he thought till she told him to pick up his purse so that they could go to the doctors office for a refill. He wasn’t sure what she meant by that, but when they pulled up to the same clinic where he was inflated like a balloon he didn’t want to get out of the vehicle. “No, no, no way. Miss Megan these fucking things are big enough!” He said gripping the girly growths on his chest.

“You were doing so well Leah. How many strikes was that outburst?”

He considered getting out of the car and running, or moving as fast as he could in heels. Taking them off and running on the hot concrete wouldn’t be a real option, but running wasn’t really one either. Stay and have the inflation thing happen again and be punished, or run and have nowhere to go. If he chose option two he couldn’t hit up Lucus looking the way he did, he couldn’t trust daddy to not turn him over to Miss Megan. He would just end up back here, still having this done and punished worse. So hung his head, pulling out the book, seeing he already had one strike pending. “A good girl is always obedient. A good girl is seen and not heard. A good girl never argues or complains. A good girl never uses foul language. So four strikes.”

“I would also say talking to me that way was not polite. We are here to make sure the doctor's hard work doesn’t go away Leah, saline is temporary. I think that falls under always looking your best. In fact you weren’t smiling or acting happy and proud. It seems you broke every part of your motto.”

“Oh no…” He said looking into the blonde woman’s blue eyes as she looked at him sternly. He went from not trying to give her a reason to giving her all the reasons.

“Eight and one that you already have means three punishments.” Megan let out a long sigh like having to punish him was a trial for her too. “We could go down to the brothel after this and have two men double team you, that could count for two, but what to do with the last punishment. What do you think Leah, what should your other punishment be?”

Thinking about what she said made him look at the door handle, but he had already been over that thought process and he wasn’t sure if the child safety lock was on. “Please Miss Megan, please it was one mistake. It was a big one, I shouldn’t have said any of that!”

“One… mistake…” She said, drawing out the words like she was tasting them. “So you think you should just have one strike? Or just one punishment?” Liam’s eyes lit up, she wasn’t talking to him with contempt in her voice. The question seemed real, it could be a trap or it could be the witch actually was going easy thanks to him playing his role.

“One punishment?” He phrased it like a question, not wanting to push for the just one strike option, if anything was a trap it was certainly that.

“Hmm, they do have a longer lasting option they can do here, but I didn’t want to choose it because of the price. It still isn’t permanent on its own, but if you want to go with that option we could consider this matter closed, but it is pricy so I’m not sure.” Megan acted hesitant about the option she was giving the feminized young man, but in truth it was already what she had signed up for. What they were going to do today wasn’t saline, but a saline like solution that would work well with hormone treatment for people wanting to look feminine. When mixed with high doses of estrogen it would help guide the body to keep the dimensions from the injections. Doing this and making Liam think it was his choice, just seemed like such a better way to handle it.

“Umm ahhh, what about the money I had in my bank account Miss Megan? Could we use that?” It wouldn’t matter if what they were going to do lasted longer, she was just going to keep him coming back to get the saline or whatever. Nether was permanent so he could still look like himself after all of this torment was over.

“No, that was also used to help get you a new wardrobe and I doubt your father has enough money. Did you have something in your room that was worth anything? Maybe I could send Charles down to the storage unit to pick it up and sell it.”

“No, the only thing I have that is worth anything is my bike.”

“Excellent, we can sell that to pay me back for the procedure you want.”

“Please no, I love that bike!” Megan shrugged and took off her seatbelt.

“That is fine, let's head inside and get you your saline refill and then we can head down to a brothel.” Liam balled his hands into fists, his longer nails pressing hard into the flesh, causing a little pain. He would like to think she was bluffing, but consider the first thing she did was tie him up to give a blowjob to his friend and almost his brother he knew better.

“You… you can sell my Suzuki Thunder.” He said feeling just as defeated as he had since Lucus slid his cock into his mouth.

“We could sell your uncle's bike, are you sure though? I wouldn’t want him to be upset when he came back into town.” She hadn’t planned this, but the outcome was just delicious.

“He won't be mad. Miss Megan I promise. He would do anything to keep his favorite niece from getting into trouble.

“I will get on that right now and try to get a good price for it, but for now let’s head inside.”

The process was much the same, but took a little longer and in the end Liam felt sore all over once again, like he had been stung by bees and swollen, but he looked much the same with a girly figure that he shouldn’t have. The choice to get this done was his, making the choice to do this felt incredibly wrong he thought as he looked in the mirror at his naked body. So long as he put a hand over his groin or moved in a way to cover it all he could see was a girl with a smoking body, his body. If he hadn’t made this choice this still would have happened, but it would be more temporary, that and he would now be on the way to a brothel to be fucked. He knew he made the right call with the options he had, still though it was wrong. No man should have large perky breasts or a rear end that someone could bounce a quarter off of. With a large sigh Liam put on his bra, only struggling a little bit before his tits were cradled supportively in the cups.

He had finished getting dressed, paid little attention to what the doctor was saying, just nodded along before being escorted back to the vehicle. That was when he had been told where they are going next, to pick up his babysitter for the night. Where he once again had to take out the little pink book to write down another strike, when he was told they were on the way to pick up Bailey to babysit. The name Bailey felt like a bucket full of hammers had slammed into his head. Her niece Bailey was the girl that had gotten him into this mess. She had overreacted and blamed him for things so that she wouldn’t get in trouble. The slutty girl had teased him and flirted all night, was into the sex just as much as him, but now he was looking like a large breasted teen girl.

Liam didn’t want to get in the SUV, but when Miss Megan told him he wasn’t being obedient, he quickly got inside and wrote down in the little book. Hoping his quick action meant she didn’t go into the other ways, he wasn't being a good girl. They drove in silence, the seatbelt along with his bra felt like a vice around his chest after what he just went through, but he dared not complain. Not with the constant smirk Miss Megan had on her face.

He wasn’t sure how he was going to handle seeing Bailey. This could be his chance to get her to confess the truth, but to do that he would have to reveal who he really was. Thinking of exposing himself brought a new wave of panic, as he thought about the girl seeing right through his disguise. “Miss Megan, can I ask you a question please?”

“Of course you can, sweetheart.” Megan said without looking away from the road, still incredibly pleased how all of this worked out.

“What if Bailey knows who I am?”

“Well first off, you should be calling her Miss Bailey, she will be in charge of you after all.” She took the time to glance into the rearview mirror, seeing the grimace that appeared on Liam’s face briefly. “I also don’t expect she will so long as you play up being your new self. The happy girl that dreams of being Miss America. Bailey isn’t a bright girl, so I would imagine so long as you imitate her and do what she says she will have no reason to even think of something as outrageous that the pretty girl in front of her is really a boy.”

She made it sound so simple, but she really did have a point. Bailey wasn’t even smart enough to follow some of his simple jokes. While it would be boring, he bet if he asked her a few questions about makeup she would drone on all night on the topic. That thought gave him a little more confidence, till they pulled into the parking lot for Bailey’s apartment and he saw her standing there waiting.

The girl looked beautiful in her outfit, she was dressed in some sexy office wear. He eyed her up and down from the reddish, maybe salmon colored three quarter sleeve blouse that had little crystals at her neckline and seemed to flare out or have its own little skirt. She paired it with an off white or light gray pencil skirt that stopped just before her knees. He thought about running his hands on her bare legs as his eyes trailed down, seeing her feet end in a pair of brown leather heels with a thick buckle around her ankle. The heels themselves might have been five inches and the idea of her mincing around an office like that gave him dreams of how he bent her over and fucked her and how he would love to do it again at what ever job she must have come from.

His feelings of lust crashed like a wave on the rocky cliffside of his anxiety and feelings of doom. She smiled brightly, waving her hand in the air before picking up a black and pink backpack and heading their way. With each step of her heeled feet on the sidewalk instead of the normal click, clack, click clack he heard doom, doom, doom, doom. Liam’s brain shuddered as more of his life was going to be shattered the second she got a good look at him.

Bailey waited on the sidewalk outside his apartment, he had just enough time to run inside to tinkle and check his makeup before rushing back outside and down the stairs. He had been so excited with the idea of seeing Liam in person, dressed up like a girl and what he could do to mess with him that he hadn’t even considered how normal things were getting with Candi driving either Mommy’s car or her Daddy’s each day depending on who slept at whose house the previous night.

Aunt Megan had been giving him updates and photos of Leah that filled him with such glee. When she had asked him to babysit he felt like a kid being told they were going to Disney. All week he had been distracted at the office, thinking of things he could and couldn’t do to get back at the man who stuck his dick inside of him and now that moment had finally come.

Seeing Aunt Megan pull up he gave her a wave, picking up his backpack and trying to control his excitement to not gush too much over Leah. He could only see a little bit of her in the back seat, but she looked so cute! Bailey couldn’t contain the smile on his makeup enhanced face. Getting into the car she smiled at the older blonde woman who had made him live his life as a teenage girl, but she was also his chance to get out of the situation. “Hi Aunt Megan! So happy to see you!” Bailey said, reaching over to give her a hug, before turning his attention to the person buckled into the backseat.

“It always makes me happy to see you too Bailey, I love your outfit.” Bailey’s attention shifted from the blue eyed girl in the back seat and down to the outfit he picked out that morning. He had changed shoes three times before choosing the brown leather pair to contrast the outfit. “Oh my god, thank you, but what I’m like wearing is nothing compared to what Leah has on. Leah, I love that dress!”

“Leah this is my niece Bailey, she will be watching you tonight. Your father and I expect you to treat Miss Bailey with the same, if not more respect than you would show us. Now what do you say?”

“Thank you for the compliment.” Liam said in a small voice tugging slightly on his red dress with an under-pattern of black with white polka dots that peaked through in places on the skirt and his chest. He squeezed his legs together like that would help Bailey from seeing his manhood through the outfit and the tuck job. “You look very ahh pretty too.”

Liam was having a hard time looking the girl he had taken to bed in the eye. He was almost holding his breath waiting for her to ask why he was dressed up like a girl, every passing second she didn’t mention it bringing him more anxiety instead of peace.

“Awww thank you Leah, I think we are like going to get along super well!”