Date prep!

Opening the front door Amanda made it home an hour early wanting to make sure she was able to help Bailey get ready for her date, knowing she would be nervous for multiple reasons. Coming inside she could tell right away that the carpets had been vacuumed and smiled that Bailey was doing the chores she set out. Putting down her purse she started walking toward Bailey’s room, but stopped when she saw the sight in the hallway. Sitting still out was the ironing board with the apron across it. Changing course, she picked up the apron and put away the board noticing some wash had been done, but nothing made it to the dryer. “Baby steps, she at least did some of the chores.” initial reaction would be too angry at Bailey for not doing as she was told, she had been the sole one cleaning up the place for a while and this was going to be a good opportunity to change that, but it was also to try and distract Bailey from tonight.

Knocking once on the door and opening it Amanda stepped into Bailey’s room. “Did something more important come up today?” she said to what appeared to be a teen girl sitting up on her bed in her stockinged feet looking at her phone. “Oh umm, hi mommy, umm. Yes, no.. Not really, sorry I just got like distracted.” Bailey said honestly forgetting about the what he was supposed to do after his encounter with the police officer. Sitting down next to Bailey on the bed Amanda leaned back on the pillows and put her own around Bailey and started to slowly run her fingers through the long blonde hair. “If this is going to work sweetie, you have to do what I say. I do so much around the house and work late, do you think it is fair I do everything?” not saying a word Bailey just leaned into his girlfriend as she ran her fingers in his hair. The feeling was pleasant and this is the first time in a while they had just cuddled, he tried to enjoy it ignoring how he was dressed and the memory of Officer S. Cooper, in the end he shook his head knowing she wanted an answer to the question. “No, that is right, it isn’t fair. From now on you are going to help around here, wearing a dress or no. But when this is all over if you give me any of that macho attitude of it being woman’s work, I now know I can get you in a skirt.” she said smiling teasing the disguised man. Bailey still didn’t respond with words, just leaned more into her and put his arm over her waist. “I can tell this is hard on you, but you know if you focused on the chores today you would have been too busy to think about it. Now come on princess let us get you ready for tonight, we have a lot of work ahead to make you look perfect for your first date with a boy.” this time Bailey did respond verbally, still no words though, he only groaned.

Amanda made bailey strip in front of her back down to his panties while she went through the drawers and closet to pick out the perfect outfit. Looking back at him in just the black thong panties it was difficult to ever imagine this person as anything other than a teen girl. “Now dear the first thing we are going to put on is this corset, it is an over bust corset and it will pull in your waist and help give you an hour glass shape that men just love.”

“Mandy, I don’t want to wear that and look better for any man let alone August.” he said with disgust in his voice, hoping he could reason with his girlfriend. Her goal wasn’t to **** him like Megan who had bought the thing for him to wear. “Bailey, rule number one.” she said sternly looking down at Bailey who was already three inches shorter than her before she had on her three-inch heels she wore to work. “You are going to wear this, because it will make you look more feminine for someone who will being paying more attention to your curves or lack of. Not only that, but it might give you some appreciation for what woman go through for a date, like I have done for you many times. Now let us try that again as mother and daughter. Princess you will just love what this does to your figure, it will help you keep your man’s attention on you.”

“I can like only hope August’s attention stays on me.” the pretend girl giggled. Bailey hated her calling him princess with a fiery passion of his soul, but she seemed to like it and how reminded her of being called that herself when she was younger. Bailey was grunting as she started to pull the laces in constricting his waist while he held his arms above his head holding onto the door frame. He thought it was over before she pulled one last time pressing her knee to his back. The act reminded Bailey of what he was taught to do when saddling a horse to make sure they were not puffing themselves up so the saddle would be loose. “Oh, that is just perfect Bailey! Now sit on the bed and I will show you how-to put-on stockings and attached them to the garters.” she said with glee.

Looking in the mirror Bailey had to admit it truly did give him an hour glass figure and pushed the fake breasts in a way to make them look bigger. “This thing makes my tits look as big as yours.” he said taking multiple shallow breaths to try and fill his lungs. “Breasts dear, and yes it does do a good job of making my little girl look more grown up. Careful with the breathing honey, we do not want to have you passing out.” she said taking Bailey’s hand moving him to the bed, showing him how to roll up the nude stockings with a black lace top and attaching them to the garters of the corset.

The stocking covered legs were something Bailey loved to see on a woman, the last one he saw it on was the escort, Candy. If only Megan hadn’t come in then he wouldn’t now be wearing a pair of his own.

“You do have a good collection of heels for someone that has been a girl for less than a week, but for tonight I think you should wear the pair you had on earlier today. I would not have picked them, but after seeing you walk around them earlier, I have no doubt you will be fine if you remember to take small steps and lean on August if you feel like you can fall. Men love it when we do that. Amanda helped Bailey with the strappy heels, him having trouble bending in the corset. “Just a few more things, dress, makeup, hair and accessories.” the makeup Amanda applied to Bailey while he sat down in the burgundy dress was a night time dramatic look like Candi had shown him for a video the previous day. Looking in the mirror as his girlfriend painted his face, he thought of how bad this all was. Him a twenty-five-year-old man, pretending to be an eighteen-year-old girl while his girlfriend who was pretending to be his mom was dressing him up to be an object of desire for a twenty-one-year-old man who knew each other, not as friends but they had met twice previously. All the while he saw as Mandy looked like she was just beside herself with happiness pretending to have a daughter to help getting ready for a date. The end result of the makeup was a dramatic dark smoky eye look, with long lashes and the matte lipstick he had worn previously. “Stay here, I will be right back, I know just what to do with your hair!” while she scampered off Bailey looked at his phone to see the last message from Candi saying how she was on the way.

When Amanda returned, she had a spray bottle with water in it, some different types of combs and a curling iron. Plugging in the iron she let it heat up while showing Bailey the jewelry she would be wearing that night. A gold bangle for his right wrist, a gold watch for his left, that was another gift he had once gotten for her and a set of large gold hoop earrings. “You seemed to like the larger hoops, so I thought these would be perfect for you.” she said beaming with pride looking in the mirror at Bailey. “Mommy.. You keep giving me things I.. your ex-boyfriend gave you.” he said noticing a pattern. She only chuckled. “He got me a lot of nice expensive things, and it is a mother prerogative to pass on the things she loves to her daughter.

By the time the Connors arrived Amanda had already taken over a dozen shots of Bailey, the teen vision had her hair handing down lightly curled with gold jewelry to of set the dark dress. Amanda opened the door giving Derrick a light hug and welcome them inside. “Candi, you are a vision of loveliness dear. Every boy that sees you two girls tonight is going to have their heartbeat quicken. Say is that the same lipstick Bailey has on?”

“OMG, like yes I had to get it when I tried Baileys at the mall the other day and oh my god... Bailey you are like so hot!” Candi said scampering past Amanda to stand in front of Bailey the two of them looking each other over, before standing next to the dressed-up man and holding his left hand. “So, like do we look good daddy? Do we look like real sisters like I said we would?” rubbing his jaw Derrick looked the girls over. “You two really do look like you could be sisters, don’t you agree Amanda? And sweetie, you know I don’t think it is too late to go back and change into some jeans.” Amanda placed her hand over her mouth as she saw the two-standing next to each other, they looked more than sisters. “The two of you really do look more a like then I thought, no one is going to confuse you for the other, but wow. Bailey sweetie, how do you feel about having a little sister?” Bailey rolled his mascara covered eyes knowing what was about to happen. It wasn’t Candi that spoke up it was Derrick.

“Actually, from what Bailey and Candace have decided Bailey is the younger sister. Right girls?” before they replied Amanda chimed in “Bailey, younger?” that was Candi’s turn to answer as Bailey only blushed and looked to the ground wanting it to swallow him up. “Oh yes, of course. Bailey like treats me as the big sister. I have been helping her come out of her like shell and she defers like to me for decisions, then like the other day she said she was the younger one and like I’m not going to correct her. She is like already a little shorter than me so who like wouldn’t believe it.” with a single nod Amanda looked to her disguised gussied up boyfriend who looked like a girl playing coy. “Bailey has always been young at heart; it is nice that she has best friend to help her like you dear. Derrick.. Your daughter looks lovely, and you have seen the way some girls dress. Now tell her she is beautiful and how proud you are her.” Derrick tilted his head looked at Amanda and then back to his daughter standing next to Bailey. “Mega Corp is better off for listening to you, I suppose I could be too. Candance my dear, you have an inner beauty that the world should strive to match, most days when I look at you, I still see my little girl, but tonight you have the look of a beautiful woman. I am proud of you more than you know, just seeing you like this makes me wonder how much longer I am going to be able to hear you call me daddy.” the tall man held a firm grin obviously trying to hold some of his emotions in.

Candi ran over to him like she was born to walk in heels and wrapped her arms around his neck jumping up, forcing him to catch her around the waist. “Oh daddy, I will always call you that. I love you!”