Chapter 15

Accepting the baby wipe from Megan, Liam cleaned off his cum from his hand. He couldn’t even look the woman in the eye after what she had just made him do, what she had just watched him do. The dildo was still slick with his saliva, a reminder of where it just was. For not following the rules she set forward he had earned eleven strikes and for that he was going to have to suck on a dildo three times a day. He really needed to stop getting these bullshit strikes before he could figure a way out of this or weather the storm.

Holding out a small waste wicker basket for the disposable baby wipe, Megan couldn’t help but smile. Knowing one of the next punishments that Liam was going to get was cleaning up his mess with his tongue going forward. Who knows, maybe he will even grow to like the taste, but at the very least she was going to make sure he got used to it. “You go ahead and take off your shirt and panties Leah, I have something else for you to put on. I will be right back.”

Things still didn’t feel right, and Liam sure had heck knew why. His body had been inflated like a balloon today, his teeth have been pulled together tightly by wire, pills for the pain had his mind feeling foggy, on top of all that he was coming down with something that was making him feel weak. Getting up from the bed he looked back towards the dildo, he didn’t even get to finish the bullshit meager meal, instead he got that thing in his mouth. Liam rubbed his jaw for a few seconds before deciding to hurry up with what he was told before she came back and counting it as a strike for not following orders.

Pulling off the panties with cartoon characters on them and the pink t-shirt, Liam couldn’t help looking in the mirror over the dresser. Seeing a petite girl that was stacked, that looked to be a in a foul mood. Looking away from the mirror Liam saw a large worn softball with writing all around it, names it looked like and a picture in a frame sitting next to it. Inside the image were two girls, the one on the left he figured was Megan’s daughter. She was pale of skin, dark raven black hair and the same large blue eyes as her mother. The other was a hispanic girl with short curly hair with a rather large chest. The two held each other by the waist smiling for the photo. The frame itself said best friends on it. “I don’t know what your name was, but I have a pretty good idea why you didn’t stick around here considering who your mom is.” Liam said looking at the pretty, but pale girl inthe photo.

“Leah, I brought you some vitamins I had ordered, the ones you helped carry in. They will help makeup for what you are missing with your diet and considering I wanted to get more done with you today I also have a shot of B twelve to give you a boost in your energy.” Megan said walking into the room holding a few things in her hands, a small cup with pills in it, a glass of cold water and a syringe full of a red liquid. The pills were vitamins to make sure Liam stayed healthy with the diet, but she had also found some supplements sold overseas that promised to help a girl get that feminine figure she dreamed of. The same pills she had given Bailey, she had even ordered enough to make sure Bailey got the refill she had asked for, course she still thought they were to help keep her libedo in check. She had been unsure about ordering more for Bailey with the medication the doctors were already giving, but she figured the professionals could even all that out.

Looking at the items she carried Liam was suspicious, but it wasn’t like it would matter much if she injected him with something or he took a pill to knock him out. There was little more she could do to him besides cut off his dick and considering the punishment she wanted him to keep doing that wasn’t an option. He tried to think of what else she could be up to, but it was incredibly hard to think, so he reached out and took the pills. Swallowing them all at once with a gulp of water.

“A bit of a pill popper I see.” He didn’t respond, just drank down the rest of the water, hoping it would solve his hunger pains.

“Do you think I could finish my umm.” He stopped and started again with a smile on his face. “Miss Megan, do you think I could finish my dinner?”

“Dinner time is over Leah, you shouldn’t have thrown a tantrum like a little girl. I am tempted still to diaper you and send you to bed early like a little girl should, but I really would like to go shopping with you tomorrow. So how about I let you decide. Would you like to be put in a diaper, given a bottle of milk and sent to bed? I will come change you in the morning to get you out of your wet diaper, or would you like to stay up like a big girl and learn what it means to be one?”

“Big girl…” Liam said looking over at the package of baby wipes she had brought into the room, knowing the rest that would go with it had to be close at hand. Men smiled at the fully naked person in front of her, Liam had the presence of mind to hide junk behind his hand, but had yet to learn the modesty of a girl to cover her chest. Still he was trying to make himself as small as possible while naked, like it would make him less noticeable.

“Okay then, come over here and put our hands on the end of the bed and put your rear out for me.” She waited for the much more feminine looking Liam to comply.

“No girl, when I say put your rear out, I want you to stick it out like you are trying to ask someone to use you. Stand further back from the bed, bend more over, feet together… yes just like that, dear.” Megan said as she pinched some of the fat on his hip before injecting the B twelve. It has been a long day for her too and had given herself a dose, figuring she was going to be up late teaching this newly minted girl a thing or two.

With the injection done she had Liam go fetch the bag near the table of what she bought earlier. She smirked knowing he couldn’t be happy moving through the house naked, a much different naked than he was used to. She was sure the hairless skin caused the house to feel much colder than he once would have thought, and with every step he was going to feel the sway of his new pretty assets. When he returned she fished around inside the bag for the package of plain cotton panties with a lace band and tiny bow in front.

“I got you some basic panties to start, tomorrow we can get some more in your style. If you would like to put these on you will have to ask me for them.” Megan waited for him to look over, since the masterbation he seemed **** to look at her, making her think he was finally learning his place.

She shook the package as she looked him in the eye. “Well do you not want these? The diaper is still an option.”

“Miss Megan, Can I please have them.” Megan pointed to the package of six panties in her hand.

“These? If you want them you should ask for your panties. I am happy to hear you asking so nicely, but you really need to use complete sentences Leah.”

“Miss Megan, can I please have my new panties?”

“Of course Leah, here you go. Take out one and put the rest in the left top drawer there, you will find it empty. Tomorrow we can split some between here and your house so that you have some in both locations.” Waiting, Megan watched the blushing Liam pull a single pair of panties from the package and slipped them on before putting them away in the drawer. “Yes, Miss Megan.”

He hadn’t bothered or probably think about tucking his manhood away, but she figured that can come tomorrow. “Those look rather cute on you Leah, can you look in the mirror and thank me for getting you such cute panties?”

She had worded it as a question, even with his sluggish mind he knew she was trying to embarrass him some more and maybe make him react so she could just punish more. Looking in the mirror he saw what he did before, but this time the girl was wearing panties. She had a little bulge in them, and looked much happier than before, thanks to the smile he now wore.

“Thank you for buying me panties Miss Megan, they are the cutest.”

“I am so glad you think so Leah, but tomorrow I promise we will get you ones you will like much better.” Joy, joy, joy down in my heart… Liam said mentally mocking the religious song as it pertained to being happy.

“Now here is your new dress!” Megan didn’t make him beg or ask for it this time. “Raise your hands up dear.” The dress was as simple white cotton number, with slightly puffy short scrapped sleeves. Turning Liam around to face her she tied the fabric at the bust into a simple knot like was intended for the dress. Though anyone looking at Leah would be able to tell the girl wasn’t wearing a bra.

“That looks just so pretty on you, I could just eat you up. Now sit on the bed so I can put on your shoes. I am so excited to see you wear your first pair of heels.” The pair in question were navy blue, with half an inch platform in front colored a light brown. The heel itself was about three and half inches the same color as the platform, and a thick leather strap the same color went across the inside of Liam’s foot before being buckled.

“Take a good look at those heels, don’t you think they are just the cutest? I think they look perfect on you Leah. What do you think?” Liam was almost grinding his teeth together when she had slid the white cotton dress over his body. The light material felt so strange on his hairless skin and it didn’t go nearly low enough, stopping mid thigh. If he had to wear a dress why couldn’t it be something that showed much, much less skin. The heels were anything, but a contrast to the dress and something he would rather see on a date. So he said something close to that to make the crazy woman happy.

“These would look good on a girl going on a date, they are cute.”

“I’m glad you think so, but we aren’t done sweetie. You are going to need to learn to walk in them, I will be here at your side for a little bit, but then you will be on your own. Here let me get something to help.” Megan left the room, coming back a few minutes later, seeing Liam still just starring down at his now heeled feet.

“I am just going to wrap this belt around your thighs to help keep them together, I don’t want you walking around like some tomboy. Just remember heel, toe, heel toe. One foot in front of the other, move your his, back straight, chest out, head held high.” Megan said that knowing it way way more than he was going to be able to retain at the second, but he was going to learn.

Walking with him up and down the hall she had to keep him from falling a handful of times, but she had to give the little creation credit, he kept a smile on his face the entire time, or something close enough to it that she wasn’t going to ding him on it right now. Now she wanted him to focus on the walking, everything would come together over time.

“Miss Megan, the belt…”

“Isn’t it great to have to help you have the perfect walk you want? In no time you will be strutting out on sage with a sexy walk winning one beauty pageant after another. I’m so happy you appreciate how thoughtful I am Leah. If you weren’t I would hate to give you a strike.” She said cutting him off before he could complain.

Liam swallowed the saliva in his mouth, afraid of the next punishment if he got up to three strikes again. Today had been hell, he did not want it to get worse. “The belt is helpful, thank you Miss Megan.”

After moving up and down the hallway for another fifteen minutes Megan broke away to watch instead of being a helping hand. “You got this Leah, every girl is unsteady in her heels when she first starts out, but you are a natural.” He was not a natural, but she thought the compliment would bother the feminized boy more than telling him he walked like a boy.

“You know I think we can do better, hold on.” Megan moved past Laim into her own bedroom, he wasn’t sure what she was doing, but after a minute of just standing there in the heels he wished she would have let him sit down while she did whatever it was. Turning his head he looked over at the couch and recliner in the living room, considering moving over there to rest his sore feet, the heels were anything but comfortable and he wasn’t sure how girls wore them for a few minutes let alone all day. Though he considered the crazy woman might have found the most uncomfortable pair on purpose.

“I found it!” Megan yelled from her bedroom before coming out with a cream color handbag and a small leather strap. “This type of purse is held in your elbow. You need to learn how to carry your purse, and I think I will get something to right around your upper arms, you keep moving them around. Remember dear, keep your elbows in.” She put the purse on his arm like he was a manikin and left again for a minute before coming back with a ball of twine.

“Best I could find for now dear, but a few wrappings of this will do exactly what we need.” She said wrapping the twine around him a dozen times before tying it off, forcing his upper arms to stay tightly to his side and not move.

“Now Leah, inside the purse you will find a tube of lip gloss, a small purple book and a pen. As you walk down the hallway you will need to stop at the mirror at the end of the hallway and the one in the middle to check your makeup. If you fail to walk with grace, or fail to check your makeup you are going to open that book of yours and write down you have one strike. From now on you are going to keep track of your own strikes, and let me know when you have earned enough to be punished. If I think you are fibbing though you will earn an extra punishment. Oh and one more thing, I think it would be best if you recited your good girl motto while you walked. Try not to mess up, I don’t think you want the strikes.”

Liam started walking down the hallway hearing the click, clack, click, clack of his, his… heels on the hardwood floor. He loved that sound when he was with a girl, he did not like the idea that it came from his footsteps, but still his mind was fond of the sound. Just something else to be bothered by, his own mind rebelling as his legs and arms were tied together as he walked down a hallway talking about how he was proud to be a good girl and leaning close to a mirror to check the makeup that was put on him. The fluttering eyelashes, the thick pouty lips were all his and it was all so wrong. When he had started it was almost eight at night and the little book was blank. When Megan had finally called an end to the **** it was just past eleven thirty and the book had two tally marks in it. Both times when he had neglected to stop to check out reflection in the mirror as he concentrated on trying to keep his body just right while reciting what he needed to do to be a good girl.

“You did good tonight Leah, before bed we need you to use your new toy again and then I will show you your nightly routine with removing your makeup and applying the right creams and powders. I bet you just can’t wait to tell your Daddy tomorrow how much fun you had with your sleepover can you?”

“Miss Megan, I have had the time of my life, but I am very tired.” None of that was a lie, though the smile on his face was very much so.

“That is exactly what I wanted to hear, now run along like I taught you to your room for the night, I will be right there.” Moving down the hallway Liam moved with his eyes closed, happy this **** would be over, but he was still being marched to a different type that she made him experience earlier.

“Stop right there Leah!” Liam halted in the hallway opening his eyes unsure why she was using the strict voice.

“You forgot to check your makeup again as you went past a mirror. I told you earlier that so long as you are wearing heels you need to always make sure your makeup is perfect, didn’t I?”

“Yes Miss Megan.”

“What is the last line of your motto?” Megan snapped her fingers at the question.

“I am a good girl and proud.” Liam answered automatically without having to think about the answer.

“Well it doesn’t seem like it to me, so for strike three I think whenever you are doing your practice with your fake dildo you are going to show me or anyone who is watching how much you are enjoying it. Plenty of moaning and enthusiasm, the first time I see or hear you aren’t doing just that, then I will consider that three strikes by itself. Not just because you aren’t being an obedient girl, but because you aren’t following your punishments. Is that clean Leah?!”

“Yes ma’am!” I hate her, I hate Miss Megan so much… fuck I mean, stupid brain! Liam went back to the mirror checking out his reflection and for the first time saw his lip gloss really had rubbed off from something he had done with his lips at some point. She was about to show him how to take off makeup, but he didn’t dare think she wouldn’t penalize him for not fixing something she clearly knew he saw. So with his upper arms still pinned to his sides he pulled out the lip gloss and slid the little wand over his lips, knowing those pillowy soft looking things were about to be wrapped around a dildo. If he was just able to look at those lips and pretend they belonged to someone else it wouldn’t be so bad, but they were his, even if his actions were ****. Those lips would be wrapped around a dildo, sucking on it in a matter of minutes.

Megan went off to get her phone to snap a few pictures of Leah or maybe a video. Everything she put into today had left her exhausted, when she gave Liam this punishment she had lost track of the previous one she was going to do. She mentally kicked herself for slipping up at first, but the idea of Leah acting enthusiastic when it was time to make her clean up the cum seemed so much better. Her misstep would work in her favor, but she had to be careful. Liam still acted much more resistant than she thought he would, and that made her wonder about Chuck and how he was doing at the bar drinking with his cage keeping his dick locked away. Handling Bailey was one thing, but now she had a lot of plates in the air and needed to be more careful.