Chapter 38

Tuesday morning had passed much like other days at Megan’s with Liam now doing leg lifts on the back patio, a thick shake to drink with plenty of time for him to practice his good girl mantra, that he could easily recite now while doing any number of activities. When it came time for the afternoon dildo practice, something Liam never looked forward to, he tried something new.

“Miss Megan, I was hoping, maybe.” He was feeling apprehensive about asking to not do this anymore, that maybe he would be punished for just bringing it up. He had been doing so well, he hadn’t had to write in his journal about strikes for a few days now, but the way she stared at him told him that now that he started, he needed to carry on. “We could stop doing this?”

Looking at the person sitting on the bed in front of her in the light blue dress that had little sunflowers all over it, white pantyhose and yellow high heels was the same person that **** his dick inside Bailey and more than likely others. She had been much harder on Liam than she had been on Bailey, yet she had more fun with Leah too. “I know you have fun playing with your dildo, don’t you?”

“Umm… yes of course Miss Megan, but…”

“You don’t have to feel embarrassed Leah, go ahead and tell me how much you love it.” Megan said, crossing her arms.

Having to say things like this out loud was not the direction Liam wanted to take this. “I get to play with it a few times a day and I love it, like really love it, but…” He didn’t get to finish before he was interrupted again.

“Of course you love it Leah, not everyone is a natural like you. So I don’t see the problem.”

“What, what if instead of pleasuring myself I could do something more umm productive with my time?” Tapping her finger to her chin Megan thought about what else she could have Liam do that would mess with him just as much. She was already considering starting anal practice with one of the next punishments, but Leah really had been so good as of late.

“What do you suggest Leah?” Liam blinked at her a few times, causing the long lashes to flutter. He hadn’t really thought of something else to do, he just figured he had been a good girl. What was the point of being a good girl if he was still going to be punished?

Looking down at the pink dildo he also could see the hint of his breasts with how low his dress went, making him think of a girl rubbing his dick between her breasts, but that was the wrong direction. He needed to focus on being productive and in the direction Miss Megan would want. “Maybe I could try different looks with make up and umm different hairstyles?”

“You know, I like that. We can move you playing with your toy to once a day, you don’t want to neglect your self care.” She smirked thinking of Charles and how he really did enjoy being sexually active with him, but he deffitly was a different creature the longer she kept him waiting and locked up. “Though, I think you should also write a letter to your boyfriend. It could be a love letter, it can be poetry, it can just be you telling him about your day, but I think it would be cute for him to get letters in the mail from you. Don’t you agree?”

“Yes, absolutely!” He was already getting good at doing his makeup, girls did their hair in so many different ways he figured it would give him plenty to try and he couldn’t imagine it would be difficult. The letters were cute he had to admit, he never had a girl ever do something like that for him, so he was positive they would have a big impact on the teen.

“How about we start with the letter so we can make sure we get it in the mail before pickup, then we can have you start working on different updos. It will be good practice for the pageant.

Sitting down in the living room Megan pushed the coffee table up to the couch, having Leah sit on the floor in front of it so that her feet could fit under the couch and hold them at a pointed angle. Why not do two things at once, she figured. She left the feminized man to himself for a while, making him start over with a new piece of paper when she decided Leah’s handwriting wasn’t girly enough. It did make her smile, seeing the poor grammar, there was obvious effort put into it. The little note made her heart swell.

Dearest Jeremy,

We talk on the phone often, it doesn’t matter what we speak of because I hang onto every word you say your voice brings a smile to my face and helps ease my troubles away you sang to me. you sang to me, YOU SANG TO ME!!! No one has ever done such a sweet thing to me before no one has made my legs weak with their voice Jeremy you are so amazing and I am so happy you chose me to be your girlfriend! <3

I don’t know if you will get this before our date tomorrow night, but I am like so excited to see you again! But I’m also so nervous! What if this, what if that… it all keeps running through my head because I want everything to be perfect for you. Worried or not, I keep thinking of you and your smile. I can’t wait to see it again!

“This is well done Leah, good job.” He knew he shouldn’t care what she thought so long as it was good enough to keep from putting the sex toy in his mouth, but her praise still made him smile. Considering the weight of her eire, her praise just seemed to mean more to him. “Now would you like to practice different looks with your hair and makeup next, or do something else?”

“Makeup next please, Miss Megan!” Liam quickly responded to her question happily. He had worked hard to figure out how contouring and things like that worked and if she wanted to do things like how Bailey had her makeup done on Sunday instead of jerking off then it would be an activity he would happily do.

When Bailey arrived he was highly amused seeing Leah sitting on the floor, a three way lighted mirror sitting on the coffee table with different brands and types of makeup covering the rest of the surface. “Hi Auntie!” He gave a quick hug to Megan before turning his full attention to Liam as he leaned forward sliding a dark liquid in a thin line across his eyelid just over his eyelashes. “Hi Leah! Looks like you are having fun, I always love playing with makeup too.”

Glancing in the mirror over at the happy blonde girl, Liam gave her a smile. Of course she does, she is the girliest girl ever. He may be **** to stop and inspect himself whenever he saw his reflection, but she was the type of ditz that did it naturally. “I’m trying new looks and it is super fun. Oh I know when Miss Megan leaves do you want to try new looks too!” Getting her in front of a mirror with a mascara wand would be his ticket to the girl being distracted while he did what he needed to do.

Turning from Liam, Bailey gave a big smile to his aunt. “I love that you have her playing with makeup like this!” Bailey let out a few giggles at how deliciously feminine the activity was. “That sounds like so fun and we can totally watch a few makeup videos on things we want to try. Candi has like… a ton of them that you are going to love.” Bailey said, turning his head in that direction before being shocked at what Megan had to say.

“That was all her idea, that and to send her boyfriend a love letter in the mail.”

“It was not, like shut up!” Liam had his back to them and he hoped they couldn’t see the blush on his cheeks through the mirrors. It was not his idea to write Jeremy and it wasn’t like he confessed his love for the young man.

“You want me to shut up?” Bailey quickly moved his head in tens of tiny shakes of his head.

“Sorry Aunt Megan, like didn’t mean it like that.”

“It is okay pumpkin, I know you just say whatever pops into your mind especially when you are excited at the idea of makeovers with Leah.” Bailey looked between Megan and Liam with a small smile, trying to conceal the big one he felt.

“I’m like… kinda am.”

“I know pumpkin.” Megan gave Bailey a hug reflecting on how much their relationship had changed after Leah came into the picture. “The two of you have fun tonight, I have an uber on the way to pick me up, but Charles and I will be back before ten.”

“We totally will.” Bailey said, almost salivating at the idea of making Liam do more and more girly things. “But like do you think we could use your jewelry for our makeovers?”

“Only if you promise things will not end up going home with you. Your mother and I have never had a problem sharing things, but the giving back always tends to take longer than it should.”

Soon enough Bailey was sitting on the floor next to Leah, talking the other feminized man into trying a more dramatic look. Liam found himself with dramatic makeup, his eyelids having a few different colors, but the main part was a glittery orange. He had heard from a teacher he was with how glitter was like an std and he really hoped that wasn’t close to being true. “Girl, you look fab!” Liam smiled at the girl, wishing the praise didn’t feel so good. As a boy he hardly ever got compliments, making the girls that gave them stand out more, but as Leah, people were constantly giving them. It was hard for him to not appreciate them, even if they were for things he didn’t like. “Like thank you, but umm… I really don’t think that look works.”

She looked pretty as can be, he would happily tackle her right now and show the girl how much he appreciated the way she looked, but that wouldn't help his goal. Bailey looked from Leah and then into the three way mirror, frowning. “Shoot, I think I see what you mean.” He was surprised she saw any flaw, he didn’t, but she was a vain girl so the ruse worked the way he wanted. As she started to wipe off her makeup he pulled his feet from under the couch, wiggling he toes and stretching before standing.

“I will be like right back, I gotta go potty.” Liam didn’t wait for her to respond before moving off to the restroom, stopping at both the mirror in the hallway and checking out his new look in the bathroom mirror. He didn’t spare a thought for how he kept talking like Bailey when he was around her as he fluttered his lashes at himself in the mirror, seeing the light practically dance off his eyeshadow. He giggled at how fascinating it was and how girls just had so many more options to change how they look. He told himself that he of course would be happy to not have to spend all this time getting ready, but a few weeks ago he never even considered the options girls had.

Standing there he waited another forty seconds before slowly opening the bathroom door so that it wouldn’t make as much sound. Sticking his head out he could see Bailey still had her back to him as she worked on her face. With a smile he crept out of the bathroom, moving more down the hallway till he was at the end. On the left was Miss Megan’s bedroom, the door open from when Bailey went in to see her jewelry and grab a few things, like the large metal button earrings hanging from his ears now. On the right was her home office, touching the doorknob Liam held his breath as he turned it and stepped in.

Inside the room, the only room in the house anyone could consider a mess with how many files folders took up space on the floor. The small old leather beat up couch had a single cushion free to sit, but he had seen it much fuller before. He didn’t dare turn on the light to alert the bimbo out in the living room, but he had **** in turning on the monitor and just hope it didn’t give off enough light that she would be distracted from making herself up. He liked the girl, he really did, but he did not enjoy how she practically dragged him down the path of being girlier to be more like her and all he could do is act like he was happy about it.

When the computer screen showed the login page he frowned, wishing she didn’t have a password. The woman lived alone, there was no need for such things and a quick look around showed him that Miss Megan did not write down her password on a sticky note under the keyboard or anywhere else. He tried her daughter's name to see if that would let him in, but Rebecca, Becky or even Beckie didn’t let him in. Three failed attempts made him worried if it was going to lock him out or alert her in some way. He knew there were other ways to shorten the girls name, but those are the only two ways he heard referred to as. Before he could consider something else or even if he should attempt something else he heard the familiar sound of high heels on the wooden floor coming down the hallway. He quickly jumped to his feet, his instincts telling him to hide. The only option would be the room's closet or opening the window to jump out, but the house wasn’t so big he had enough time for either as he panicked.

“There you are Leah, what are you doing in here?” Bailey tilted his head to the side with the question, smiling at Liam who looked like he had been caught. He never thought his old protege was stupid, but constantly acting like an airheaded girl could have gotten to Liam if he didn’t have the same mental fortitude he had if Liam thought hiding in aunt Megan’s office was going to get him out of more time practicing with makeup. Then Bailey giggled a little thinking about how Leah was the protege now.

The sudden giggle from the girl made Liam do the same out of nervousness, trying to rack his brain what to tell her, and then when he saw her eyes move over to the computer he blurted out the first thing he could think of. “I was trying to get some of the video’s we were watching on a bigger screen. It is hard to see everything just on your phone.”

“That is a great idea!” Bailey said stepping toward the computer, before frowning. “Do you know the password I don’t?” Playing the videos on the computer also saves battery life, Bailey figured.

“Umm no, so umm that isn’t going to work.” Liam wished he had more time to try and figure out the password to the computer, but he was happy at least the girl bought his story. Though considering who it was, the use of the word makeup with any excuse could have probably worked. He was too busy congratulating himself to notice that same girl making a phone call that he would have very much liked to intervene before it happened.

“Hi Auntie! Leah and I were doing our makeup and wanted to watch some videos of it online. No, no like nothing is wrong with your internet, but we wanted to watch them on your computer. Oh, yeah, but like my phone only has half power and… no I didn’t bring my laptop. Yeah that would be like a big help! Thank you, see you later.”

Watching Bailey point her phone at him like it was a gun, Liam felt his heart beating, faster and faster. Him wondering if Miss Megan was about to come back to punish him in some new way or even have Bailey herself take him over her knees and spank him for trying this.

“So like she said we can’t play on her computer, but told me she has an extra cable for my phone in the junk drawer in the kitchen. I was going to say we would be stuck using our phones, but I totally remembered Candi sending a video from her phone to the tv in her hotel’s living room.” What felt like a lifetime ago Bailey remembered being able to plug a usb stick into a tv at his parents store in order to play a video clip on repeat, but he wasn’t sure how Candi sent her phone up to one. “I will call and ask her.”

“Hey sis! Yeah we are having a blast and… no Auggy and Jeremy aren’t here. So hey listen, we were working on some makeovers and… yeah we were using some glitter eyeshadow… Orange for her and pink for me. Yes it looks great, sure I can, no wait I wanted to ask you how you sent that video from your phone to your tv the other day.” Liam watched the girl stop talking to giggle at something Candi said, a side of the conversation he couldn’t really hear.

“Yes I know you have like lots of videos about makeup, yeah because we were like watching you! No, you don’t like need to come over to help in person. I totally got this. No, like I can babysit on my own. No you are not a better babysitter… Okay, sure like I will totally take that bet. Yeah Leah can decide, see you soon.” Bailey hung up the phone call, letting out a long sigh.

“So like Candi is going to come over to help.” Liam nodded his head, moving over to the computer and turning the screen off. His plan having a big setback now, but maybe the two girls could keep themselves occupied and forget about him. They sometimes seemed off in their own little world when they talked, though something about the conversation nagged at him.

“What was that about a bet and a better babysitter?”

“Oh, like Candi and I make bets all the time and it is totally unfair how she wins most of them, but she said she would show me how to be the best babysitter so we bet on it. All you have to do is tell her I’m better.”

Liam considered that he could ask for something in return, like some alone time in the office, but the ditz might tell Miss Megan. So instead he went for covering his tracks. “Umm I can do that, but maybe we don’t tell Miss Megan we were in her office?” Waving his hand at the comment, Bailey was about to dismiss it like it was no big deal, they were just going to use it for videos she would have no problem with them watching, when it dawned on him how Liam came in here on his own when not being watched. “Aunt Megan wouldn’t care, but we don’t have to tell her anything.” Bailey lied as he walked out of the home office.

The rest of the night Bailey was going to get to see Liam doing the most girly of activities while pretending to love them, he was going to win a bet with Candi and then go to sleep happily knowing Aunt Megan was going to set the pretend girl straight. Bailey had no real idea why Liam wanted to get on the computer, but it didn’t matter. It was the oddest thing, Bailey thought. When he first went into the room thinking about catching Liam up to no good it was Liam he thought of, but then it was Leah and now that he was thinking of what was in store for him it was Liam again. Heck he was thinking of the person he was watching over as Leah earlier when they were sitting together. The idea amused him that even knowing the truth of who Leah was, still his mind was often telling him they were nothing more than just another teen girl.