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Chapter 82 by Nicegent42
What's next?
Reading Till Mommy Comes
As Bailey laid out Becky's old bed struggling to pull his new jeans on he knew one thing for sure. Aunt Megan was not slipping, not all. The jeans had a little give to them, but he was sure this was more akin to what it would be like to put on latex with how hard it was to get the low rise skinny jeans on. Bailey exhaled as he buttoned the pants he so desperately wanted, or thought he did. Standing up he slid his feet into his new heels and put on the shirt Aunt Megan told him to wear. It was the same light pink shirt with my little pony on it that he had to wear with the stupid children's overalls, but now it looked different with a C-cup bra instead of the A-cup. Now it no longer went all the way down, stopping just below his navel.
Bailey pursed his now thick lips as he looked himself over. How do I look like some teen bimbo, how did this even happen? He asked himself as he reached for a brush to fixed his now messy hair. Moving in his new pants felt odd, he had never worn pants that clung to him like a second skin and as he turned to look at himself from different angle he was pretty sure he had a better ass than the lady he was following earlier in the day. Sitting down on the edge of the bed he crossed his legs and rested his head in his palm as he braced his elbow on his now crossed leg as he just watched the feminine creature in the mirror over the dresser. The day wasn't over and it had been crazy and he wondered what Candi had been up to.
Leaning over to the nightstand Bailey hit dial on his phone to call the girl. He didn't really need to talk with her, but she was always this ball of sunshine and he was feeling a little down. "Hey sis! How are you feeling?" Bailey had actually forgotten he was supposed to be sick. Uncrossing his leg and crossing the other one as he watched himself in the mirror, no that girl didn't look sickly at all. "Better, but like everything that happened kinda ruined my weekend. Cheer me up?" Bailey could hear a door closing and assumed she closed her bedroom door. "Well I'm glad you are feeling better, and I do know exactly how to cheer you up. The new X-Men movie is coming out soon. Daddy said he would take me, but I told him my little sister would want to come." Bailey could hear the girls smile and the idea of seeing the new comic book movie did sound really good. That and knowing the girl thought of him when her Dad offered to spend quality time with her brought a smile to his face. That time was precious and she wanted to share it. Bailey wiped a few tears from his eyes, unable to keep his emotions fully in check.
"Candi… thank you, that means a lot." Candi must have heard in Bailey's voice that her friend was trying not to cry. "Of course, you are my best friend. I will always be here for you Bailey, just like you would for me." As moved as Bailey was, it also made him feel a bit like a heel. He needed to treat her better, he had been treating her like a chor, something he had to deal with, at least internally. While she had been nothing, but supportive and kind to him. Annoying at times, but she meant well and he needed to give some of that back. "Candi, I ahh got to go, but I… thank you for being you." Bailey looked at himself again as they said their goodbyes and realized one nice thing about the lashes. At least when he cried, he wouldn't ruin his mascara.
After adding two pink bangles on his left wrist and a white one on his right Bailey walked out into the living room to show his warden how he looked. "What do you think?"He asked, feeling the tightness of the jeans across his ass, the panties wedged between his cheeks, the straps of the stuffed bra pull on his shoulders and the architect of his feet held in an unnatural way. All to look like a girl, a very specific type of girl. "I think you could do better, go back into the hallway and come out with the excitement I know you feel for how you look." Bailey took a deep breath and as he did he was thankful he wasn't wearing a corset, and then walked into the hallway and halfway down before pivoting on the ball of one foot and spinning around to come back out. "Tada!" He said holding up one hand open straight above his head and the other in his hip and a big smile on his face. "You look lovely, now come, have a seat and let's have another chat."
Walking around the coffee table Bailey sat on the edge of the couch cushion, legs crossed at the knee, back straight, chest out like he had been taught. Bailey watched as Aunt Megan reached over to a small pile of paper and picked up the top one, and held up a photo of Mommy… Mandy. "Who is this to you and how do they make you feel?" She was back to that again, and this time printed off photos. "That's my Mommy, she makes me happy and I feel loved." Megan put the photo face down next to the pile and picked up another. "That is Charles, my Mommy's ex boyfriend and him are friends and like you are dating him now. Oh, oh do you think you will marry him?" Bailey added a giggle at the end, as he was able to stay in character and have a little fun at the same time. Megan narrowed her eyes at Bailey before smiling and turning the question back on the disguised man. "Maybe if things go right, would you like for that to happen? Him being around all the time, me bringing him around to see you often. You could be a bridesmaid at the wedding." Bailey did not like that, not one bit and wished he hadn't tried to tease her. "Awww I would like love to be a bridesmaid!"
"I bet you would." Megan said as she picked up another photo. "That's Mommy again, you already did that one." Megan turned the photl over to look at it and then turned it back. "Everyone is in here a few times, now you said who she is, but how does she make you feel?" Pursing his lips together Bailey understood how this was going to go and when they got through the stack she shuffled then together and did it again. "Now Bailey, you have a few options for what you will do until your Mom comes. Keep in mind I don't know when she is coming over, could be soon or it could be hours from now. You can sit and work on your math workbook, write out each of your mottos, look at yourself in the mirror and say them, or you can read one of my paperback novels. If you choose that one though you will have to finish it at home, and you will have to text me what you would so in the different situations the heroine gets into if you were her, and what men you would choose that are pursuing her, and of course why."
Do math, say or write about being a good girl and about being on his knees to please men, or just read a story and talk about it. He was sure the idea came to her when she was invited to the book club. She did look happy about that one, and he thought it could win him some points. "Ohhh yeah, let's totally read the book. You already read it, so it will be like we have our own little book club!" Megan nodded as she got up to go get the book. "Suppose you are right. I will be right back with Valley of the Dolls. I loved it and so did my Mom, I'm sure you will too."
Sitting on the couch, legs crossed with his new pink stiletto heel dangling from his foot Bailey said reading the horrible chick lit about a girl named Anne in 1945, an innocent girl from a rural area moving to New York city and ends up getting a job as a secretary. In the story she starts to date one man, and then falls in love with another, but in a twist the first was a secret millionaire who said he was just testing her and he has fallen madly in love. Despite her protests he informs the media of his new relationship. She is stuck loving one man, while the one that loves her is **** to be her main focus. At one point Aunt Megan had put the backpack he had run away with next to him, but he didn't look up from his task. Every decision Anne made Bailey thought over, what would he do if he was Anne. If this was a story that not only Aunt Megan liked, but her mom… his now deceased grandmother he supposedly enjoyed then there was no telling what obscure question he might be asked.
In the story Anne had already started to date one man, but when the nephew of her boss's partner came back from the war she was smitten. Her boss and a few others warned her to stay away from the man as he was a heartbreaker, but she paid them no heed. Bailey glared at the words, wondering why she was so silly to run ahead despite the advice of people she trusted, while she had a dependable, but poor man already that seemed to like her. When it was revealed how he wasn't poor at all he felt dome vindication at his choice. That is where Amanda found Bailey when she walked into her older sister's house.

"Meg I'm here!" Amanda called out as she opened the door. Only just stepping in when she forgot herself, leaving the door open as she looked upon Bailey as the disguised man looked up at her in surprise. Putting the book face down on the couch Bailey put the largest smile he could on his face, an easy tast with how much he felt he missed the woman he loved, the woman that would take him away from here, his girlfriend, his Mommy. Once he was standing Bailey picked up his pace, throwing his arms wide to the side and cried out for her. "Mommy I missed you!" Amanda hadn't moved from the doorway, transfixed by how Bailey looked. When the beautiful teen girl called her Mommy and how she missed her it brought a large smile to her face as the two of them wrapped their arms around one another.
Bailey held her tight, missing embracing her. When she finally pulled away from him she just looked him up and down in wonder. "Look at you! Megan, what did you do to her?" Amanda said, looking over Bailey's shoulder at her sister who was leaning on the wall as she watched the reunion. "Don't look at me, I only facilitated Bailey's ideas. Now the photos and documents for your pretty daughter were all me. What did you do to your hair? And how long are you going to keep my door open?" Amanda touched the two thin braids on the side of her head, then turned to shut the door, looking a little embarrassed that she had been so distracted. "The braids are from Candace. I spent the afternoon with the Connors, planning for tomorrow and we ended up braiding each other's hair.
The two women continued to talk and catch up, with Bailey constantly watching how his pretend mother kept stealing glances at him. The excitement of seeing her again started to wane the second she referred to him as her, as a girl. He knew what he looked like, but how hard would it have been to say what did you do to him, not her. He was so busy feeling sorry for himself he hadn't noticed they were talking to him. "Earth to Bailey, ah now we have your attention. She has been like this all weekend, just spacing out like that girl we went to high-school with. What was her name… Kimberly I think. Afraid your Bailey is a ditzy girl just like her." Amanda looked into Bailey's green eyes "No Kimberly was a bimbo, who stole my prom date a week before by blowing him under the bleachers. You are not a bimbo, are you princess?" She asked the question, giving Bailey a wink. Having the woman he had, used to have regular sex with ask him if he was a bimbo girl who would go and give a guy a blow job under bleachers, was not something he ever expected to deal with, and it didn't feel good. "No, oh sugar no! I'm a good girl!"
Amanda tilted her head a little puzzled at her word choice. "She had been trying to keep from using foul language after I mentioned a lady doesn't curse" Amanda nodded and gave Bailey a small smile, finding that cute, but it changed into a sterner expression. "Mostly a good girl, you my daughter have not washed any of your clothes all week. Your hamper was overflowing and…" Amanda looked from Bailey to her sister. "You snuck off to your Aunt's house in the middle of the night. So when we get home, you are getting a spanking and you will have to figure out a way to earn your dirty clothes back, because they will be locked in my bathroom till you do." Punished… but… but, fu… fudge! Bailey wanted to yell, but he couldn't, a good girl was obedient and should be seen and not heard.
They stayed at Aunt Megan's house for two more hours catching up. Hecwas horrified to hear she knew about the good girl motto from Miss April, but while it apparently upset Miss April, M… Mandy thought it was funny Bailey had come up with something that would have been taught in a class years ago to forge a proper lady. She was beside herself with glee seeing all the photos that had been created. Like the photo of her holding baby Rebecca in her arms rocking her to sleep and all that had to do was change the hair color with her eyes closed. Each passing minute only made the anticipation for being spanked worse and he knew the only reason she was going to do it was because earlier in the week he had asked her too. He specifically said he used to be punished that way and wanted her to do it too, when in reality he couldn't remember a single time his parents raised a hand to him.
When the sun had long set they went home. Amanda held Bailey's hand for most of the ride. "You know Bailey. I'm really proud of you. I know April doesn't like what you chose as a personality, but if you choose to be sporty it would have been easier for you to fall back to who you were, and this way up and Candi have more in common. You did that, while making amends with my sister. I love you, and I'm not just proud of you, but I'm happy. Truly happy to have you as my daughter." There were many, many things Bailey wanted to say to that, but he said the only thing he could and be in character. "Like thank you. I love Aunt Megan, but I move you the best Mommy!"
What's next?
Girlfriend’s Daughter
Friday
A boyfriend finds himself to pretend he is his own girlfriends daughter so she can succeed at the office.
Updated on Aug 27, 2023
by Nicegent42
Created on Mar 6, 2021
by Nicegent42
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