Thursday morning

Slowly waking up Bailey looked down to the stuffed bear he was holding with a bit of disgust, he didn’t remember it being in bed with him last night. Dropping it to the floor he got up and stretched his arms and popped his back. Seeing the bedroom door slightly ajar he was sure Mandy had come into the room and was the source of the bear’s migration to the bed. Stepping out of the room he didn’t hear anyone about and a glance at the time told him that he missed seeing Mandy before work. With a yawn Bailey headed to the kitchen to enjoy some coffee, but saw the pot empty. “Mommy must have woken up late today.” Bailey snapped his mouth shut and made a sour face as if he could taste the word ‘Mommy’ and hated the flavour. While the coffee pot percolated Bailey turned around and leaned on the counter crossing his arms across his chest and looked down at his fake tits. “Two more days and the only tits I will be seeing are on my girlfriend and my laptop.” smiling to himself something out of place caught his eye when he looked up. On the table was a piece of paper with some writing on it. Stepping around the kitchen counter Bailey sat at the table picking it up.

Good morning sweetie,

You looked like sleeping beauty this morning, so I did not wish to wake you. Tonight we are going to be having guests over, so the two of us will be making dinner for the Connors so they can have a home cooked meal while in town. While I am at work, you are going to do some chores to make sure everything looks nice for them. Today sweep, mop the floors, wash/dry/iron one load of laundry, dust and make sure your bedroom looks presentable.

Have a good day princess, love you!

“Arg..” Bailey complained as he tossed the note back to the table. “Fucking Megan, it is her fault she is treating me like some teenager.” Pushing his untidy hair from his face Bailey got up to get some office when the front door opened and in stepped Megan. Bailey turned and just glared at her. “Do you just show up to ruin my day when you hear me say your name?” he said grumpily to the older woman. “Good morning my darling niece, is that any way to speak to your favorite Aunt? Now come here and give Auntie a hug hello.” Bailey could tell she wasn’t asking so with a sigh he shuffled over and gave Megan a hug. Pulling back after the hug Megan held Bailey at arms length. “Sweetheart, have you not showered yet?” Glowering at Megan as she held his shoulders he considered a few choice words. “Not yet, and what are you doing here?”

Letting go of Bailey and walking past him Megan placed a bag on the counter and smiled over at the coffee brewing and got out a mug, not answering Bailey till she was ready to pour herself a mug. “Well, I was going to see about removing those prosthetics on your chest. But you haven't exactly made me feel welcome. Maybe I should leave.” The idea of getting these things off earlier than expected gave Bailey a spike of joy, but he knew what the bitch was angling for. “Like, I’m sorry I am being grumpy, Auntie. You know I love you, and didn’t mean to be rude.” Taking a sip of the black coffee Megan smiled at Bailey having to act like the sweet innocent girl. “Aww, I understand sweetheart. Why don’t you make one of your breakfast shakes and then we can work on getting you all clean. How does that sound?” she said taking another sip of the coffee she knew he made for himself. “I was like just going to do that before you came.” Bailey said in a happy voice as he took a few steps over to the fridge to pull out the horrible diet shake he now had to consume. Outwardly Bailey gave the impression he was happy his favorite Aunt was here, but inwardly he was cussing up a storm as he sat down and drank what amounted to a slightly fruity flavored kale juice.

When Bailey finished off his shake he pulled a mug down to get some coffee when Megan looked up from her phone and stopped him. “Bailey sweetie, you are far too young to need coffee, too much caffeine can stunt your growth. Now off to your bathroom so we can get those off your chest.” clenching his teeth Bailey put the mug back where he found, but bit his tongue and moved along to where she indicated.

Coming in the bathroom behind Bailey, Megan put a bag on the bathroom sink. “You are such a pretty girl Bailey, stop that scowling and smile. There, yes like that.” Megan thought back to the first time she met Bailey, when he told her that she was just as beautiful as her sister if she just smiled more. Once his top was removed Megan pulled out a bottle from her bag and applied the liquid contents to a cloth and wiped around the edges of the prosthetics. As the edges came loose she worked it more and more till each one fell away free of the skin. What Megan saw when they were removed;surprised her. Bailey’s chest had seen some changes this past week. It looked like his nipples were a little enlarged and the fat had built up to maybe some A cup breasts. “Look at you Bailey finally hitting puberty and growing your own breasts.” she teased. The pills she had been giving Bailey shouldn’t have caused this much change so quickly, she wondered if maybe Bailey already had a hormonal imbalance, it could be the reason why he was so small.

“My own what!” Bailey yelled as he pushed Megan out of the way to look in the mirror over the sink. “What the fuck is this! How do I have tits!” Bailey had no idea how, but he was sure Megan had something to do with this and turned to her glowering. “What the fuck did you do to me you bitch!?” The smile on Megan’s face disappeared and her mood darkened. Bailey felt something hit his cheek hard as the sound of the slap echo slightly in the tiled bathroom. The unexpected blow causing him to fall to his ass. “You little shit, how dare you speak to me that way. What is going on there is just irritation from having weight attached to your chest for a week without having a chance to breathe. The prosthetics are supposed to be removed dailey. I came here to help you, how dare you turn on me like that.” Holding his hand to his reddened cheek Bailey felt some of the fire leave him. This was still her fault and she still fucking hit him, but she didn’t have the power to suddenly make him start really turning into a girl. “I’m… I’m sorry, I shouldn’t have said that.”

“No you fucking shouldn’t have! You know Bailey, I like you a lot more when you are acting like my sweet niece, and don’t think you got away with trying to access one of your porn sites again last night. The parent lock tells me every time you try and where you are trying to go. Not a place for my niece at all. You Bailey have forgotten yourself and I will have to come up with a suitable punishment. Unless you want me to take you over my knee right here in the bathroom and spank you?” Still sitting on the floor as Megan loomed over him, Bailey pulled his feet to his chest, feeling small as she yelled down to him and he remembered the pain and humiliation of the act. “No.. not that, please!” His voice was one of pleading as tears started to come to his eyes. “I will think of something suitable, for now stand up dear.” she said, helping Bailey stand up. “You need to get yourself clean, it will make you feel better and I have just the thing to make sure you are nice and clean inside too.” pulling a rubber bladder with a hose attached from her bag she put it in Bailey’s hands. “Bailey my dear, you are going to get your first douching.”

A few minutes later and with much complaining Bailey was naked on his knees and bent over the rim of the tub with his ass in the air as a hose was inserted in his anus. He could feel the warm soapy water flow into him. It was an odd feeling at first, and after the water just kept coming it became uncomfortable. “Megan.. Stop it, I'm full!” he complained, but dared not move. “Not yet dear, and that is Aunt or Auntie. I put up with your mom for years, I earned my title. Just think of this as you learning what a woman’s cramps can feel like.” she said giving the rubber bladder a little squeeze. Once it was all inside him Megan left him where he was as she answered a few more work emails on her phone and enjoyed the sound of him being uncomfortable. A few minutes later she pulled the lubed hose from his ass and had him sit on the toilet to expel its contents. “There that wasn’t so bad was it?” with the feeling of relief of emptying himself out Bailey just nodded to her. “Glad you think so, because we are going to do it one more time. I want you nice and clean, and from that horrible smell coming from you, that is not something you are right now.”

When Bailey was done with the douching he ended up having to do it three times before he could get in the shower and left alone, but not before Megan reminded him to shave his legs. As the hot water ran over him Bailey touched his budding breasts and felt how sensitive they were and concluded they would only feel this way if they were irritated like a rash would. Megan told him they would be putting them back on after the shower and seemed sad that she would remove them Saturday morning for the last time. He wanted to complain about her not leaving the remover for him to take them off tonight, but didn’t want to push his luck. If she wanted to be in control and play her power game it was fine, he only had to hold out till the Connors left. Pulling the shower curtain back Bailey grabbed the towel waiting for him and patted himself dry before wrapping it around him and another smaller towel around his hair like he had been shown. Wiping his hand across the misted over mirror Bailey looked at himself with the towel wrapped around his chest and the towel turban and frowned. “Just a few more days, we can do this.” he said to pump himself up, but then a thought of dread hit him. What if Megan went back on her word and showed Mandy the video after all of this anyways, or she kept it looming over his head. He hated having to trust that man hater, but what else could he do now other than just run away.

Walking into the girly room Bailey stopped when he saw Megan sitting on his bed, just tapping away on her cell phone. She looked up at him and gave a genuine smile, liking the sight she saw before her. “Hold on just a second dear, I need to finish this email and I will help you get ready for the day. Enjoy being young and carefree while you can, soon you will have to get a job like every other adult.” With that she went back to what she was doing. Bailey was going to start getting dressed, but wasn’t sure if the bitch had something more instore for him other than insulting comments to try and emasculate him. So instead he just sat on the cushioned bench at the vanity and waited. After about three minutes he saw her look up from her phone at him and go back to it. With a sigh he picked up his phone off the charger and flicked the screen on to see about twelve missed texts. Two of them were from August, with him saying he was thinking of her and a follow up of a picture of a rose, and how he can’t wait to see her again. Bailey glowered at the texts and then glanced up to Megan then back to the phone and started to respond.

Bailey: Aww, thank you. Thinking of you too! But like I have been super busy.

Bailey: IDK like when we can date again. Mommy has been like super demanding. :(

August: I get it and don’t worry. I can have my sister totally help us out and get you free, they are best friends.

Bailey: No.. we like shouldn’t get your sister involved.

August: its no problem babe, but if you are worried about it, I can just swing by her office and talk to her about when I can steal you away for an evening.

Bailey: Talk to her next week, she like has a lot of important meetings this week and I don’t want her stressed out.

August: Next week, will do. I can’t wait to kiss you again. It is all I can think about.

Bailey: <3

Flipping the message over to what Candi had sent, Bailey just couldn’t believe that exchange. He was trying to just let the guy down easy, but he sure as hell didn’t want him opening his mouth to his sister or Mandy. What if he mentioned them kissing or heaven forbid what he did in the theater. By next week this will all be over and Mandy can just make something up about her daughter having to go off to summer camp or some other bullshit. The messages from Candi were her just looking for Bailey to help out with her own boredom or so it looked like.

Candi: Good morning little sis!

Candi: Yesterday was so much fun, I mean not all of it.

Candi: Time with like your mom and all of us was great, and OMG we totes need to talk about about the fun with the lifeguard!

Candi: Do you think your mom would let us take a uber to the park Friday morning? We do like have summer passes.

Candi: NM it like says minors need to be escorted with an adult.

Candi: Are you like still a sleep!?

Candi: I did like a super fun quiz, here is the link. Tell me what you get!

Candi: Daddy texted called me and said we are coming over for dinner tonight!

Candi: What are you wearing tonight?

Candi: Wake up!

With a heavy sigh Bailey replied to his bestie. Saying he was up, but couldn’t talk as his Aunt had come over and they were spending time together and would catch up later. The wish was that it would never happen, but it was a wish he knew would not come true. Putting down the phone Bailey looked to Megan who was still typing on her screen. “Are you like going to help me or not?” The comment sounded much like an irritated teenage girl, the irritation was real, while the rest came out from days of having to stay in character. Megan put her phone in her purse and smiled at Bailey. “Sorry honey, I tried taking a half day at work to help you. But sometimes things have to be done. Now I know how much you want to be full chested again so take off your towel and lay on your back on the bed.” Doing as he was told Bailey removed the towel, but as he did he realized he was still completely naked under and went to cover his privates. “No, none of that. I have seen everything you have, and I can promise you I’m not interested in it. Now get your skinny ass on the bed.”

Laying down on the bed Bailey tried to cover his privates when Megan slapped his hand away. “Stop that, can’t have you messing this up. I doubt you want me to have to do this more than once.” Bailey felt mortified, as he lay there naked before Megan as she glued breast forms onto him. The **** feeling only seemed to increase after she had him hold them in place as she just looked down at him appraising him. “Okay, we are going to use this tattoo concealer on the edges like we did before and you should be good to go.” When Bailey went to sit up Megan pushed him back down. “Stay where you are, no need to get up.” she said leaning over him once again sponging the concealer over the edges. “Okay now, time for you to get dressed.” When Bailey sat up he could see a set of clothes laid out on the dresser for him. The first thing Bailey did was slip on the white thong panties and look down at his bulge. Turning to face Megan, Bailey could feel the pull of the breasts he moved and moved his arm up to cover and support them. “I need the tuck kit.” he said motioning to his dick causing a bulge in the panties. “No just tuck yourself back, we can do that later. I bet you would rather not use it till you need to right?”

“Umm, yeah. Thank you…” Bailey appreciated the gesture, but it felt odd coming from the woman. The next thing he picked up from the dresser was an overbust corset and he held it up and looked back at Megan who was on her phone again. With a sigh he called out to her again. “Aunt Megan, could you please help me put this on?” he said adding a little pout to sell the act. Putting down her phone Megan took a few steps toward Bailey. “Of course dear, you know if you just stayed in character we could have a much better relationship. I have enjoyed spending time with my loving niece.” Bailey wanted to yell at the bitch that she didn’t have a niece, and she didn’t even have a daughter who loved her either, but instead he **** a smile. “I’m like really happy you like spending time with me, I like totally love spending time with you too.” With Megan’s help soon Bailey was dressed in the corset, garter belt with the tags coming under the panties like is proper he was told, some tan stockings and a pair of red heels with multiple thin straps at the ankle. Looking to Megan then back to himself Bailey asked the next question. “What am I wearing over this?”

Megan smiled and motioned to the vanity for Bailey to sit down. “First you are going to do your face and later we can do something with your hair, but for the rest of your outfit I think you will be borrowing an outfit from your mom. Isn’t that exciting? One of the joys of being a girl is how we share clothes. Your mom is what, three inches taller than you? That is a lot, but I’m sure we can find you something you will adore.” Bailey looked away from Megan and whispered “Bitch” under his breath before reaching for some makeup on the vanity. Megan left Bailey to do his own makeup, only interjecting when he went to get the matte red lipstick. “No dear, go with that glossy red, let's make sure your lips shine tonight.” without complaint Bailey did as he was told. With a shiver from the ac in the apartment Bailey looked to Megan. “Aunty can you please help me pick out an outfit for the night, I’m excited to see what we can come up with!” Megan motioned for Bailey to sit up and she smiled back looking at the feminized man up and down. “Let’s go to your mom's room then, you sound excited to dig through her closet.”

When they went into the other bedroom Megan looked over at Bailey. “Hmm.” Then walked around her pretend niece to the bed and moved some pillows around. “Why don’t you sit down up here on the bed and prop yourself up with these pillows.” it was phrased like a request, but Bailey knew it wasn’t, but had no idea why. Once he was up on the bed laying at its center Megan told him to stay put and she would be right back. Bailey didn’t have to wait long for Megan to walk back in with one hand behind her back. “Okay little Bailey, you have been a bit of a trouble maker. Trying to go to places on your computer that you shouldn’t, and if you keep that up I will have your mom ground you from it, but you also seem to have a trouble staying in character and saying things you shouldn’t to your sweet Aunt that you think she can’t hear.” Bailey’s green eyes went wide, realizing just now what he said earlier did not go unheard. “I.. I…” Megan made a cutting motion with her hand to stop the sniveling reply.

“You my dear have a few options for being punished. We can of course call all of this off, you no longer have to pretend to be a girl and we can let my loving sister know of your multiple indiscretions that she paid for through your deceit.” She paused just long enough to catch Bailey's eye, who quickly shook his head. “Didn’t think so, well with you always trying to look at porn I get that you are a sexually active young woman and have needs. So I will offer you some choices, you will be picking one of them, if you don’t I will choose two of them for you. The first is this.” she said tossing something to Bailey who reflexively caught it. Bailey quickly let go once he saw the life like dildo in his hands. “You will be practicing giving a blow job on that while you call out your imaginary lovers name and moan for him, and I’m not cruel so you can pleasure yourself with your other hand. I’m thinking a nice picture of Charles for you to look at, I know I promised to set you up with his little brother. But I think the man is just handsome and I know you would appreciate it.” Bailey was already shaking his head before Megan finished. “No, not that either? Well okay, Bailey my dear, here in Nevada prostitution is legal if you go to a brothel. So if say for example my sisters old boyfriend brought one into this apartment it would be a crime, but if I took my slut of a nice to a brothel to have her first sexual encounter that would be perfectly fine. Would you like to feel a real cock inside of you Bailey from a professional?” Megan laughed when Bailey cried out. “Please Megan, no don’t do that to me!” She walked around the bed and sat at the edge of it in front of Bailey patting his leg. “Then the last option is we get you in a nice dress and you can be in a more comfortable environment at my place. Once there we will invite Charles over, and see if he would be interested in a three way. Men love three ways from what I understand, and he already said we were both pretty. Would you like that better?”

Bailey’s jaw hung open, every option this horrible woman gave him was worse than the last. He would have gladly accepted to climb onto her lap and let her spank him over those options. Bailey looked past Megan to the door, wishing Mandy would just walk in that door right now and save him, but when he looked back to Megan he knew even that would only doom him as she would rather have Mandy cast him out than let him get away with anything. So slowly, he reached out and picked up the all to life like dildo and gave what was the most obviously uncomfortable smile. “I like think I could use some practice.”