Preparations for the mall

Bailey slowly woke up, feeling someone sit at the edge of the bed making it move a bit, and then a gentle hand pushed some stray hairs out of his face that came loose from the braid overnight. “Sweetie, it is time to get up. Aunt Megan is almost here to help you get ready for your day.” looking down at Bailey curled up in a ball atop the blankets in her peach night shirt, breasts pushing on the fabric, braid coming undone, it was easy pretend this was her daughter. After last night she really did think it for the best to try and keep it that way the best she could till the end of the week when she could have her boyfriend back. A man that was willing to sacrifice his pride and masculinity just for her sake.

“Come on dear, I know you are not a fan of mornings, but it is time to get ready for your day out shopping with your friend and Aunt.”

The smile that was creeping into his face seeing the woman he loved above him slid away morphing into a frown and then scowl thinking about what was to come. “Do I have to do this?” he said in a small voice still laden with grogginess from just waking up. Amanda stood up and started for the door looking back before crossing into the next room. “Enough of grumpy girl, get up for the day.”

She heard the response of “Augg.” as she went back to her room to prepare for her Sunday at the office.

She didn’t always work six or seven day a week, the late nights at the office were always a normal thing for her or most of the lady's at the office if they wanted to get a head in the male driven world of Mega Corp, but these last few months she had really pushed herself to get things just right. To impress the correct people, to shake the right hands at the right time. Some woman at the office used their feminine wiles and bodies to get ahead, she didn’t like it but understood it. Though she had never been one of those girls that got down on her knees for a man to get ahead. For her it was always hard work, dedication, watching the numbers and critical thinking. She had earned her place as a department head in the branch office for Mega Corp, and wanted to get this promotion to lead a district. With it should could have more influence to help others like she had done for April and other woman in her department.

Padding out of the spare bedroom Bailey went into the kitchen pulling out a bottle of his favorite beer and popped the lid off on the counter. Taking a small pull to just roll the flavor around his mouth before taking a longer one thinking about how his girlfriend was treating him like a child and calling him girl. Each time she treated him like that he felt smaller and he knew that wasn’t going away anytime soon that’s to Megan. He didn’t blame Candi for the way the ditzy girl acted, that was her nature and her and her dad were the marks in all of this. It was all Megan, she could have gotten her co-ed daughter to come do this, but no she fucked up that relationship just like he was certain she drove her ex-husband to cheat and then leave her. Becky had left home to stay with some boyfriend in the city and even when that didn’t work out, she refused to go home to Megan. Bailey heard a key in the lock and as it opened to saw the woman he was thinking about as if thinking about her too much invited her to appear to make his life worse. Closing the door behind her Megan dropped a tote bag on the table and looked Bailey up and down.

“Is Victoria’s secret that Bailey likes cock?” she said with a sarcastic tone to her voice.

“What? Fuck you.” he so cleverly quipped back, before she walked forward and pointed to the dried cum over some of the letters of the word secret on the shirt.

“Don’t you worry sweetie, we will have plenty of time today to go to your favorite store, but for now why don’t you go take a shower and use these. This one is for your body in the shower, this one is for your hair in the shower, this one here is for your face in shower, that will get you properly clean and smelling correctly. Then when you get out this bottle here is lotion for your face, and this one is for your legs and body.” she said pulling bottle after bottle from the bag.

“Great, is that it?”

“It would be, if we didn’t have problem the second, I walked in. You gave me an attitude using language I would say is not fit for a young lady like yourself, that would be strike one missy, then strike to is this.” she said snatching the beer from his hands and then yelling toward the master bedroom.

“Amanda get out here!” glaring at the bitch as if it would change the reality of what was happening when she did that was not helping the events as they played out.

A few moments Amanda came out of the room wearing a smart woman’s pants suit with fitted blazer. “Good morning Megan, something wrong?”

Holding up the beer in her hands she shook it from side-to-side sloshing around the half full bottle. “We had a talk about staying in character. It was Bailey’s idea and you agreed to it and yet I find your underage daughter drinking beer. I swear if I’m the only one going to take this seriously, I am just going to go home. I love you Amanda, I sure as heck am not doing this for myself.”

“Stop, stop Megan I see what you are doing and the guilt trip is not going to work. Though I admit both of us have slipped.”

“Slipped is right little sister, look here.” she said pulling up the shirt Bailey was wearing revealing his dark green boxers. “Bailey here is wearing your old boyfriend's clothes” letting out a long breath Amanda looked to Bailey who didn’t look to be appreciating Megan holding up her night shirt. The other night she thought the two of them might be getting along better with coming to agreements for her sake and Megan taking the time to help him learn to walk in heels even if was exaggerating the walk to much.

“You are right, we need to buckle down and I do appreciate you. You know I do Megan, this is all new to me. You have more experience raising a teenage girl, and you got to raise her from a little one to grow into the role, it is just being thrust upon me. Could you, maybe help me more with how to raise Bailey right?”

“Raise me right?!, I’m twenty-five, an adult!” letting go of the shirt Megan met his eyes daring him to continue. “What was rule number one?” clenching his jaw he mumbled the answer.

“What was that dear niece?”

“Megan she is just grumpy, you know Bailey has never been a morning person. Sweetie, this was your idea and this is for the best so that we do not mess up in front of the wrong people. Just imagine what would happen if you got caught and what that would do to the two of us.” Bailey eyed the other half the beer he didn’t get to drink as he listened to Mandy.

“Rule one is, I’m a eighteen-year-old girl, not an adult.” Megan smiled and patted Bailey’s cheek.

“Mornings can be tough sometimes, and we all know how moody teenagers can be. Not to worry Amanda, I promise to help you have the best daughter you can while this charade goes on. I will make it so that if mom were around to see you and Bailey, she would be jealous. Now you go finish getting ready while Bailey takes a shower in the hall bathroom.”

When Amanda went back into her bedroom Megan followed Bailey into the guest bath. Turning around to close the door behind him Megan shoved him back a step and closed the door behind her.

“Why are you following me bitch.”

“Bitch.. Okay. I mentioned strike one, strike two. Last night I made perfectly clear what would happen if you got to strike three.” Bailey swallowed hard regretting insulting her, he was just so angry and seemed to have no power, losing all agency in his life.

“Here is the thing missy, strike three was when you declared you were some twenty-five-year-old male, when we both know you are just a teenage girl. Strike four... that’s right four you just did by opening your mouth and saying something you shouldn’t ever let alone to an adult or your Aunt.” Bailey was making quick short shakes of his head looking to Megan.

“No, you can’t. Please, she will throw me out, I don’t even have my bike anymore.” he said with panic in his voice.

“I tell you what, I’m going to punish you like I would any foul-mouthed teenager after your mother leaves for work. If you submit to it and remember the simple fact, I am your favorite Aunt that you love, then I am willing to bring you back to strike one. What do you say Bailey dear, do you want to be punished like the girl you are?”

“What.. What are you going to do?” he said with trepidation.

“Whatever I want, and going forward whenever I think you deserve it. You of course don’t have to, my sweet sister loves and trusts you, but will it be enough when she finds out the truth?”

“Fine...You win.” Bailey said his eyes downcast.

Patting the side of Bailey’s cheek Megan said. “I know sweetie, I know. Now tell me honestly do you need anything to help you pull this off?”

Megan was left her hand on Bailey’s cheek and tiled his head up to look at her. The caring tone of voice was different and a bit disturbing. “Yeah, kind of. The thing Amanda did for me with my umm my dick yesterday I need to know how to do that and figure out how to well not get hard being around a girl who is constantly touching me.”

“Hmmm, I think I can do both of those for you. Now you get in the shower and use the bottles I told you about, when you come back to your room. Not your mom’s room dear, your room. I will have some clothes laid out for you and some videos for you to watch so you can learn how to take care of yourself.

With that Bailey climbed into the hot shower once it was warm enjoying the privacy because looking down at the fake breasts as he ran the body wash over them caused him to get another hard on. Seeing his rigid member, he mentally kicked himself and hoping Megan was pulling up those videos on her phone and not his laptop.

Getting out of the shower Bailey dried off and applied the lotions like he was told before wrapping the towel around his waist and exiting the wash room. Taking a step towards his bedroom he stopped remembering where he had to go, but not before Amanda saw him as she sat on the edge of the bed putting on her heels, now having her makeup done and wearing her jewelry.

Seeing the breasts bounce free with each step Amanda stood up and walked up to her shorter boyfriend, much more so when wearing her heels.

“Young lady, show some modesty and cover your breasts.” the comment like the ones before made him feel smaller. When Bailey pulled the towel up, she smiled and kissed his forehead.

“Much better dear, you have a fun day with your friend and Aunt Megan today.” she said walking past him to grab her purse that hung from a chair in the kitchen.

“Meg, I am off. Good luck today and thank you again for everything I owe you!” Amanda heard her sister yell from the other room. “Don’t work too hard!” then with that Amanda left the apartment leaving Bailey alone with Megan.

Stepping into the bedroom Bailey saw the clothes laid out on the bed, a knitted looking bare shoulders shirt, red bra, red lace thong panties, a black jean button up skirt and on the floor below them were the white heeled wedges with the white ribbon. Then his eyes went to his laptop and saw more tabs opened on the browser showing videos to watch, he knew there was no way she didn’t see what he was watching last night. “Okay dear, let's not waste any time with waiting for your punishment. Amanda is gone so you could back out and maybe buy yourself some time before you are thrown out on your ass.”

With a hard swallow he shook his head hard enough that it flung water from his still damp hair.

“Okay good, now follow me.” she said walking out of the room and pulling a chair from the table and turning it around before sitting on it. “Now come here dear and put this in your mouth.” she held up a bar of soap. “it will remind you to talk like a lady and respect your elders. Then you will lay down across my lap to get spanked.”

“SPANKED?!” his voice cracking as it went up an octave in shock.

“Yes dear, just like any young girl that needs to be taught a lesson, is that going to be a problem?”

Bailey didn’t answer and didn’t trust himself to, biting his tongue as he walked over taking the bar of soap. He made a disgusted face as he placed it in his mouth and laying across Megan’s lap.

“Good choice dear, I think ten swats per infringement should be good. Next time I might not be so lenient.” she said as she pushed up the towel exposing Bailey's rear end. By the fifth swat on his ass Bailey was biting into the bar of soap and trying to hold back tears, by the fifteenth he was opening crying and by the end he was making whimpering sounds and trying to contain sobs as tears opening went down his face. Letting him stand back up she looked at him not smugly or with anger but kindly. “Now going forward don’t give your Auntie any reason to do that to you again. Now go to your bathroom, not the master bathroom dear, yours. Then spit that soap out and brush your teeth, when you are done with that and not before you can rub the lotion onto your rear to help soothe the pain. Then come back into your room.

Following her instructions Bailey came back into what was supposed to be his bedroom and saw his now Aunt Megan sitting at the edge of the bed her legs crossed. “Before you watch your videos dear, I wanted to tell you have something to help you stay tucked, it is a product special girl like you use to hide what they have down there, it is called Unclockable, a tuck kit. I paid extra for a rush delivery so they should be here before end of day. I also have some pills for you that can help keep that growth you have from getting hard.” she said holding up the bottle of extra strength hormones she took from the box that once held Bailey’s mother’s things when she was sick, but now had no label.

“Now remember they only help when you take them, so make sure you take the vitamin every morning. Then lastly, I wanted to address this.” she said moving the laptop to her lap with the screen facing Bailey, who was still standing there in the towel. He wanted to ask where she got the pills, but the thought left his brain gone forever when she clicked over to his old tab on the browser hitting play on the video from last night it already half way though.

“You looked panicked dear, don’t be. It is only natural for a girl your age to watch porn. This type you are watching with the what was it, the milf step mom being fucked by her step son while stuck. That is **** dear. No, no again it is okay, you look like you are ready to try and flee right now in your towel. We all have our kinks sweetie, I bet you picture yourself as the woman here all pretty and grown up being trapped and taken. I can understand my niece having a fantasy of being powerful as someone fucks her, if it was anything else though I might have to consider that another strike. So, tell me in your own words, why do you like this video that looks to be favorited.”

“Umm.. I umm.” he stopped himself to collect his thoughts to do this right and to prevent being spanked again, she had threatened that next time would be worse and his ass was already sore, the cream helped easing the redness and pain but it was still painful. “It is like embarrassing Auntie, the woman is just so pretty and the idea of that happening to me makes me want to be her.”

Megan smiled knowing the torment she was causing the piece of shit man. “Don’t even think twice about it dear, but we can’t have your mom catching you seeing stuff like that. So, I installed a parental block on any websites that is over PG-13. I know, I know you are eighteen and a girl like you has needs. I have added a folder to your desktop with some healthy porn videos for you. Here let me show you just a small part of one, I know you will just love it.” Megan opened a folder on the desktop hitting play to one of the many videos. The title showed on the screen ‘Female POV busty teen to fit boyfriend with big Dick’ and clicked through a few scenes, each one looked like it was filmed with a go pro the woman wore on her head as she jerked off and licked a man’s dick.

“See just for you my dear because I love you, now why don’t you thank me for looking out for you and letting you satisfy your urges.”

“I.. Thank you, Auntie Megan, for keeping me like safe and stuff and like giving me videos for when I’m feeling naughty.” the sentence gave rise to bile in Bailey’s stomach, but there was nothing he could do.

“No problem Bailey, now you watch the video on how to tuck that growth back and get ready. I have something else to take care of in your mother's room.”

With that Bailey was left to himself, the first thing he did was close the porn video she had left open then watched the video on how to tuck his member. It looked uncomfortable and he knew from yesterday it was, but at least you mostly get used to it. It took two tries but he was able to do it and put on the red lace thong panties and with a struggle the bra. What shocked him as that once he had it on it made him look like he was bigger. From his experience had his parents store he knew he was wearing a push up bra. “Bigger.. Just like every girl wants and every boy wants to see, just not on himself.”

Dragging his feet Bailey put on the rest of the outfit and went to go let Megan know, but figured he should close the video first. When he did, he noticed another one open he had forgotten about that she said to watch. It was a video on how to do a Dutch crown braid. With a sigh he watched it as instructed, but then went to find Megan for the next steps.

Walking into the master bedroom he saw Megan taping up some boxes on the bed. “Aunt Megan, how um like how do I look?” turning around Megan gave the biggest smile to Bailey.

“Just darling Bailey, just darling, but looks like you didn’t do your hair yet. Now go watch the other video so you can do it yourself. You are eighteen now, just because you were a tomboy doesn’t mean you can rely on others to help you every day be your new girly self.” about to leave he turned back and asked.

“Umm like what’s in the boxes?”

Megan had gone back to work taping the cardboard up and answered without turning around. “Just helping your mom clean out her room of her last boyfriends' clothes, since no one around here is going to where them. What would other people think if they happen to see them by chance.” she turned around then and made eye contact seeing Bailey looking sad. “Oh I know how much you like older men dear, but it isn’t healthy for you to be wearing your mom’s Ex boyfriend's clothes. Now run along and let me finish up.”

Comply dejected Bailey went back to his new room, but still walking how Megan had taught him the night before with the exaggerated wiggle in the female gait. Once back in he spent twenty minutes getting the hand of the hair style, one that the girl on the video did in six minutes with taking the time to explain as she went. “Got it.” he said when he noticed Megan standing in the doorway leaning on the doorframe. He wasn’t sure how long she had been standing there, but he wasn’t a fan of her watching him put his hair into this girly style.

“Great now dear, lets get your make up on.” she said sitting on the bed pulling out a traveling makeup case. Putting it down next to her she opened it up then reached into her pocket as she felt something buzzing. “Oh and darling I have been texting with your friend this morning, it seemed you left it in the other room and didn’t want her to think you rude.” Bailey took his phone still in the flowery phone case and looked at his text messages. One in particular stood out to him.

Bailey: “Candi, like oh my gosh I was just talking to Aunt Megan and oh wow you are going to love her, I know I do. But like when she heard that I was going to go on my first double date she was so excited for me and said you are like the best influence on me, if it like wasn’t for you mommy would never have let me after what happened last time.”

Candi: “That is like such great news! What happened last time, give me the 411”

Bailey: “A boy from my school like used to give me rides home and I would you know like thank him for the lift. Well mommy like home early one day to take me out to the movie, it was like super nice of her to leave work early, she works like so hard for us to like get this promotion. Like where was I? OH, yeah like she caught me you know going down on him. I was like so embarrassed and like at the same time I felt bad for him, he didn’t get to finish.”

Candi: “You did not, OMG shut up!

Bailey tossed the phone on the bed like it was a snake that was about to bite him. “YOU HAD ME GIVE A BLOW JOB TO A GUY IN YOUR MADE-UP LITTLE STORY!” calmly, ever so calmly Megan replied.

“Strike two. It seemed only fitting, I caught you with a girl named Candy giving you a blowjob. This story I think beats the real one. I could text both Candi and Amanda the real story, would you like that?”

“No.. I’ll be good I swear.”

“If you can make it through the mall trip without once back talking me, and giving me at least two hugs while are there and say telling me that you love me three times while Candi is around to here, I will move you down to strike one again. If not, I will give you twenty swats when get back here. I don’t care if mother is here, you will obey me young lady. Now that is settled come here and sit, it is time I cleaned up those eye brows, they are way to bushy. Something I boy would have not a cute girl like yourself.”

After some plucking and then makeup Megan smiled. “Last thing we need is a purse, but I forgot to get one for you to match, do you know if your mom has one?”

“Mommy has a Tory Burch white on that will like go with the shoes.”

“Bailey, since when do you know purses?” she said quizzically

“Catalogs and stuff from mom’s old boyfriend when he like was a manager at the store his parents owned. He like kept inventory and expensive things like a three-hundred-dollar purse were like important to know about.” he said doing his best to stay in character around the vile woman.

With the outfit complete Megan had Bailey assist her in loading the cardboard boxes into the back of her SUV before they headed off to the hotel to pick up Candi.

Almost there Bailey texted the teenager to meet them out front and as they pulled up Megan said. “Get in the back with your friend dear.” without argument Bailey got out, but as he did Candi came out of the building running up to him and gave him a big hug. Candi was wearing a black off the shoulder top with three quarter sleeves, a white skirt with polka dots on them, black three-inch chunky heeled booties with a black clutch purse. When both girls were in the back and buckled up Candi was the first to speak up.

“Thank you so much Miss Best, you and your sister are like the best, like lol. Daddy wanted me to also say thank you for him too and wanted to know I have gas money for you and have money to pay your lunch as a thank you.”

“That is sweet dear, but you keep it. I’m sure the extra money will come in hand at the mall today.”

“Awww you are like so amazing, daddy told me you were like the older sister, but I think no one could think of you ask old with how pretty you are.” the comment endeared the girl to Megan and watched in the rearview mirror as she turned to Bailey and talked about how cute she looked and Bailey did the same in return.

“Wait like OMG you look so much better, did you pluck your eye brows? They look so good, I wanted to like say something the other day, but like totes didn’t want to hurt your feelings.”

“Actually Candi, this morning Bailey begged me to help her get her eyebrows to look like yours. She said how she wanted to be like you. Now look at her, pretty as a picture.” Megan said while looking at Bailey in the mirror every so often to see the reaction as she drove to the mall.

What came out of Candi’s mouth was a high-pitched sound like only a teenage girl could make. “EEee! Like OMG, for reals you said that, Bailey?!” nodding the disguised boy replied. “Like of course, my last name is Best, but I like think you are the best.”