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Chapter 81 by Nicegent42
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Bailey Got Birthday Shoes
Placing one hand under Bailey's jaw Megan tilted the feminized man's head up as she took a closer look at the thick swollen lips. "Bailey, now that she is gone tell me why you got your lips done." They had done a wonderful job in Bailey, her lashes were now long with natural looking curl. Her lips came out well enough that just looking at them would give men ideas and they went wonderful with her pearly white smile. "I like told Heather to make sure everything was right and it wasn't…" Megan jerked Bailey's chin up more forcing his jaw to close. "You look right to me, and I think you look your best. Isn't that what you want?" Bailey wanted to tell her how everything went wrong, but still couldn't manage to get to worked up, but the mention of looking her best made Bailey nod his head just a little as she still held him. Megan let go of Bailey, amused at the fortunate turn of events, and how Bailey had kept himself rather calm.
"Are you telling me the salon made a mistake and did you lips?" Bailey nodded, not saying a word. Aunt Megan had cut him off before and mentioned his motto. He didn't want her to **** his mouth closed again, that hurt a little. A good girl is seen and not heard. "And you didn't want it to be done." Bailey shook his head no. "But you want to look your best?" Bailey nodded yes, and remembered to smile. "I would say with your lips looking like that if we add your lipstick, you will look your best. So go ahead and fix your lips and then tell me what you think of them." Bailey pulled his phone out from his purse and some red lipstick. Turning the camera on to use it as a mirror he rolled the red over the slightly tender lips. Pressing his lips together to make sure it was evenly applied he took another glance at how he looked. Thick fluttering lashes framing his large green eyes and those large kissable lips. She looked kissable, fuckable, beautiful, and it was him. A good girl always looks her best, and the girl on the screen looked her best. If he wanted jeans, he had to be a good girl, if he wanted to stay on Aunt Megan's good side he needed to be a good girl. "I like do look my best, so how could I be anything but happy!" Megan smiled at the response, she was learning her lessons, though Bailey did still seem a little off. "Great then let's go look at shoes." She said linking arms with Bailey. "Oh I love shoes." Bailey chimed in as they went off to their next destination.
Jeremy's heart started to beat quicker as he saw Bailey coming into the store with a taller and more mature woman in the best possible ways. He thought it had to be her and Candi's mom. The girls hadn't texted him but once or twice and he was too afraid to start a conversation and look ****, but maybe if he made a good impression with their mom. He put the box he was holding on the shelves and glanced over at his own mom. She almost always seemed disappointed in him, or afraid he would get hurt, but if he got a girlfriend like Bailey or Candi she would be proud. He tucked his black polo work shirt that read Shoeholoc back into his pants and told himself he could do this a few times before making his way to the two beautiful blonde women. As he got closer he noticed Bailey looked a little different.
"Hey Bailey, wow you look incredible!" Jeremy said with a little wave as he got closer. "This must be your mom. Hi I'm Jeremy." He looked between the two of them and **** himself to say a little more. Girls like compliments, you can do this. "I can see where your daughters get their looks from. You both look very, ahh pret.. beautiful today." Megan took the young man in and if he kept growing and his shoulders filled in he be handsome. For now he could be described as cute. "A pleasure to meet you Jeremy, always nice to meet a young man with manners. Bailey your friend gave us a compliment, what do you say?" Bailey remembered Candi talking about him having a self-esteem problem, and how they both gave him a kiss on the cheek for a photo. Stepping closer to him Bailey pressed his newly plump lips to his cheek. Giving him a kiss, and leaving a red lipstick mark when he pulled away. "Thank you Jeremy." Bailey said, smiling and twisting his hips a little to make it look like he was happy to have received the compliment.
Jeremy put his hand over where he had been kissed and blushed hard, while Megan raised an eyebrow at Bailey. "How, ahh umm, I um. How can I help you both today?" Megan smiled at the young man, seeing him so completely flustered from a kiss on the cheek was beyond cute. "My niece needs to see a a variety of heels today. We don't need to bother you and can help ourselves." After giving him a peck on the cheek Bailey was sure Aunt Megan would draw this out, and was pleasantly surprised when she told him they didn't need him. "Oh it is no bother! Your ahhh niece and I are friends and I was hoping to umm…" Jeremy **** himself to make eye contact with Bailey. "Was hoping we could get to know each other better. So you just tell me what you need and I will find it!" The **** must have been wearing off, because Bailey sure felt the rise of his panic levels. Oh God! Another boy is into me. I'm a man not some dick craving bimbo! As he thought the word dick the lines he had said over and over again in the mirror bubbles forward. Her name was Bailey, she liked to tease, she liked to show the boys she knew how to please and sometimes did it on her knees. "Well if you insist, we both would love to hear more about you."
Sitting in one of the chairs, Bailey twirled his hair around one of his fingers as Jeremy brought more and more shoes for him to try on. Each time he helped put them on and take them off, while Megan would ask him questions. Like where he went to school, how long he worked here and the most often question. What was his opinion on the current pair Bailey was wearing. She would show him the photos of the last pair and ask him what was better, leaving Bailey out of it mostly. Except when she asked "it is nice to get a man's opinion, isn't it?" Bailey felt **** to agree, as he felt one of the boy's hands on the back of his calf and the other slipping another heeled shoe on. "It is like so hard for me to decide what I like best, knowing what you like Jeremy, like really helps." The boy's hand lingered a little longer than was needed as he smiled up at Bailey. "You know Jeremy, I don't think we are going to go with any of these. If you had to pick one shoe here in the store for Bailey, what one do you think just fits her?" Jeremy bounced to his feet and pointed at Megan for just half a second in his excitement. "I know just the ones, be right back!" He said running off down one of the isles.
"Bailey I want you to show that cute boy how much you love what he picks out, okay?" Bailey automatically nodded his head. But wondered what she meant, like was he to give him a hug and kiss him on the cheek or did she want him to fully kiss the boy. My name is Bailey and I like to tease… No, no she wouldn't, would she? "Umm like how much?" Megan looked at Bailey dumbfounded, tilted her head and squinted just a little. Trying to figure out what she meant, before her eyes went wide. "No, you little slut, just tell him you love whatever he picks." She said in a whispered voice. A blush came to Bailey's face, that wasn't what he meant, did she know that and was messing with him? Feeling embarrassed Bailey looked down at his painted toes, sitting next to box after box of heels. When Jeremy returned he opened a SK box that contained pink stiletto pointed toe heels. "This line is called Barbie stiletto, we have them in a few colors, but I just thought these…" Jeremy's voice trailed off as his confidence at his pick started to leave him. Bailey could feel the woman's gaze bore into him. "Oh my God! These are so cute! I love just love them, can you help me put them on?" Bailey hadn't meant to also flutter his lashes as he held out his foot, but the damn things made blinking look like an invitation. "I just love them, Jeremy, but like a hundred and thirty dollars is too much for me right now. Otherwise I would totally buy them."

A mischievous grin came to Megan's face. "Don't be silly Bailey, tomorrow is your birthday party. I can put it in my credit card as a gift." Jeremy looked to Megan and then back to Bailey. "You are having a party tomorrow?" He sounded hurt to Megan, but knew he wouldn't be for long. "That's right. We are celebrating both Candi and Bailey's eighteenth at the local park. It was a last minute thing, Bailey said she was going to ask you to come, but my niece would forget her head if it wasn't attached. It starts at six pm, do you think you can make it?" The boy's face lit up and he looked across the room to the register. "I have to ask my mom if it is okay, but I really want to!" Standing up from her chair Megan put a hand on his shoulder. "Is that your mom over there at the register?" He quickly nodded, but looked a little embarrassed. "I would love to talk to her and find out for you, and maybe get to know the woman that raised such a find young man. You two stay here for a few minutes before following."
Jeremy looked at Bailey with a small smile, and he could just feel the seventeen year Old's eyes running over his body. "You look like you changed. I mean, you look amazing Bailey. I hope I can come to your party." Repressing a shudder at how he was being looked at Bailey smiled and cocked his head to the side. "I don't like know what is planned, but having you there would make that night like so much more." Worse, horrible, depressing were the words he wanted to add, but instead Bailey just pretended to get distracted as he played with his long hair. A second or two later he met Jeremy's eyes with a wide smile. "I'm sorry, like what was I saying?" The stupid girl act just might be able to get him out of conversations and doing things he didn't want to do, Bailey thought of it like it was a strike of lightning, a moment of genius and how much he was sure some girls did the same thing. "You were talking about your party." Jeremy said helpfully. "Oh yeah, you should like totally come." Bailey giggled trying to play it up. The act only made Jeremy laugh, and Bailey wasn't sure of he was laughing with him or at his expense with acting dumb. "Oh like, let's head over to my Auntie." Bailey took two steps in the pink pumps when Jeremy put his hand on Bailey's arm. "Hold up, let's put your old shoes in the box do you don't forget them and you can wear those out."
"There you two are, I was just telling Christeen how small of a world it is. Her and Jeremy live just two blocks from my house. She even invited me to a book club she runs." None of that mattered to Bailey, except if she had less free time she might mess with him less. "That is like amazing Auntie." He tittered. "I have also given permission for Jeremy to go to your party and I wanted to thank you and your sister for inviting him." Seeing the skinny woman, he had expected a harsher voice with the way she looked at things, like the definition of resting bitch face, but it was light with a pleasant tone. "Oh like of course!" Bailey was **** to stand there for another twenty minutes as the adults talked. Yay, good for you. Now you have a friend, come let's go already. He wanted to say, but a good girl is seen and not heard. So Bailey stood there holding the box in both hands in front of him like a demure girl should, an outburst now would cost him a pair of jeans.
Finally leaving the store the headed to Macy’s for the sale Bailey dreamed about, not because of the reduced price, but the ability to wear pants. He started to think about maybe she would let him get a few pairs, a light pair and a dark pair. When Megan stepped in front of Bailey, just in front of the store he suddenly had a feeling of dread, like his hopes were too high. “We spent a good deal of money today pumpkin, those new heels you fell in love with were expensive. I’m not sure you need a pair of jeans, what do you say we get home and prepare for your mom to pick you up for tonight?” No, nooooo he needed this. “Auntie, but haven’t I been a good girl all day?” Megan took a moment to consider that and nodded. “You have been, but I also wasn’t expecting to buy you those shoes. How about we make a trade, you give me something and I will get you a pair of jeans. Jeans you can wear whenever you want all summer long, what can you give me of equal value?” This wasn’t fair, she promised! What could he give her that she couldn’t take or command him to do? “What.. what do you want?” Megan shook her head at the reply. “Come on, you can try harder than that.”
Bailey wracked his brain for something she would want him to give her, something that would make him suffer. He had given up real food, ****, his gender.. “Ahh, umm do you want my game system?” That made Megan laugh, not just because that wasn’t close to what she wanted, but also the idea of Bailey giving up all his video games for a single pair of girls jeans. “No, from what I understand you and Candi had fun playing that, I wouldn’t want to take away from your fun with your best friend.” She watched Bailey dart her thickly lashed eyes around the mall like the answer was somewhere around there. “How about this as an offer? You get a pair of jeans and you in addition to doing your exercises and workbook at home, you will say your mottos while looking in the mirror every day and of course you will video record it for me.” Jeans, pants.. Something remotely masculine for saying the phrases she was already making him do. If she wanted couldn’t she just tell him to say them whenever she wanted? No she doesn’t have that kind of time. Bailey hesitated wondering if it was worth saying those horrible lines everyday. “Don’t worry about it pumpkin, let’s just head home.” Megan said, putting both hands on his shoulders and gently turning him around. When Bailey was facing away from the store he looked down at his bare hairless legs under the khaki skirt that ended in the pink heels. “No… I really want the jeans.” He whined and at those words Megan stopped pushing on him, but instead leaned close over his shoulder. “Are you sure?” Bailey started to slowly nod and picked up pace with each consecutive move of his head. “Yes, I will say my mottos and I get some jeans.”
When Bailey left the store he owned a pair of jeans, not ones he loved at all. In fact he wasn’t sure they were going to fit, the pair she had him try on were tight and then she picked up the next size down and just bought them without him trying them on. It was not perfect, it was not great, but they were jeans and saying a few lines in front of a mirror was an easy price to pay. He held the two bags, one in each of his hands, head held high. Today things got out of control, but Aunt Megan was slipping to let him get pants in exchange for a few words.
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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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