Car ride with Miss April

Sliding into the car Bailey smoothed his white short skirt and moved his legs together as he shut the door to the little black sedan. With a bright smile that he in no way felt like giving he spoke to the woman only a few years older than him. “Hi Miss April!” April tilted her head a little watching how perfectly he mimicked a teen girl and couldn’t believe how he dressed in the off the shoulder white blouse that showed plenty of midriff, matching white skirt and heels. He was dressed more like a teen girl ready to entice some young man on a lunch date than a doctor's appointment. “Buckle up.” She said in response as she moved the vehicle into drive. As the car rounded the first corner in the apartment complex Bailey moved one hand, palm down under his chin and took a selfie, capturing both himself and April. The phone made a shutter sound as if it was a camera, indicating it took a photo. April raised one of her thin eyebrows as her dark eyes settled on the platinum blonde disguised man in her car. “Bailey.” She said to get his attention as he sent the selfie off to someone on her phone. April wondered briefly if it was sent off to her little brother, but considering how he kept talking about not having a chance to spend time with her or how she was playing hard to get, April doubted he was the receiver. “Yes, Miss April?” The response had April roll her eyes. “It is just the two of us, you can cut the sweet little bimbo act. Just talk like yourself, okay?” Looking down at the phone at what she just asked, what she just allowed was like a prison door being opened and the message on the screen a reminder of what he was getting away from even in the smallest way.

Bailey: Headed off with Miss April, don't know where we are going lol.
Bailey: Thought I like looked cute today.
Candi: OMG you totally do!
Candi: You look different...
Candi: WHAT DID YOU DO WITHOUT ME!
Candi: OMG you look so good I'm mad.

Bailey nodded his head and gave a thousand watt smile with how happy it made him to be able to stop pretending, even if it was just around her. The phone buzzed with more texts from Candi, but he ignored her to enjoy just this one moment not having to be Bailey Ann and just be himself. “Oh my God, you like have no idea how tired I am of all this Miss April.” Bailey said as he used both hands to tuck the loose hair behind his ears, showing off the earrings shaped like white daisies. Stopping at a stop sign April turned her head to glare at Bailey for answering the way he did. She took a deep breath before turning out into traffic, thinking about how much it bothered her that Bailey was adding the word like into the sentence and saying the phrase oh my god with the emphasis of a coed girl from a bad movie that pushed the stereotype. “I know Amanda really appreciates what you are doing for her, but tell me why you act and dress like that.” She said, taking her hand off the wheel and motioning to Bailey. It caused Bailey to look down at himself and give a small shrug. “I don’t like have a lot of clothes.” Bailey said thinking about how the majority of his clothes were locked away as punishment for not doing laundry. “Didn’t Megan buy you a bunch of clothes? You could have just worn some of your old jeans.” Thinking of his old clothes caused Bailey to frown and cross his arms under his breasts, the action pushing up his now natural if not small bosom. “Aunt Megan totally took away my old clothes and won't give them back and she makes me dress this way and act like I’m a good girl!”

From the corner of her eye April could see Bailey sulking like a child and still using that fake voice he had been using since that day in the park, though it sounded much better now. “So you need more clothes?” Bailey nodded his head, all his attention focused on the dark haired woman driving the car. He put both his hands together like he was praying as he spoke to her. “Oh my god yes! Could you please, please… help me get more clothes!” April clicked her tongue with disgust. “Why don’t you go ask your Aunt or Mommy to help you buy you things.” So focused on the words Bailey didn’t notice the tone of her voice that showed how she felt about his behaviour. Turning away from her and crossing his arms Bailey looked out the front window of the car, pouting a little. “Ick no, I like told you Aunt Megan is why I have to act like some bimbo that wants to get on her knees to please.” The turn of phrase caused April to raise an eyebrow. “And like Mommy.. I mean Mandy will just get more outfits like this, I can’t tell her how much I hate this. You said it yourself how happy this is making her. So I like have to be a good girl, happy and proud.” With that came a silence in the car, April didn’t respond to what Bailey said and when it went on long enough he opened his mouth to ask her if she was okay, but was cut off before a single word came. “No.. just stop. I’m not playing some fucking sharrade with you Bailey. You dress, talk and act like some air headed bimbo and blame it on others. For fucks sake you don’t even stop when I tell you that you can drop the act.” Bailey cut in, but only got a few words in. “I did stop!” April pulled off to the shoulder of the road and stopped the car so that she could turn and give the green eyed man, if you could call him that anymore her full attention.

“Did you now? Megan isn’t your Aunt, yet you keep calling her that and you are what two, three years younger than me but calling me Miss April like some elementary school child. Bailey worked his jaw a little like he was chewing on her words, not sure what to say. He wasn’t aware he was doing that, he caught himself calling Mandy his Mom, but didn’t notice the others. “You claim you don’t want to act like a girl and how Megan makes you, but you just begged me to buy you clothes.” Bailey held up a hand like to tell her to stop. “I was just…” He didn’t get out more than that as April made a cutting motion. “You had your chance to talk, I don’t know what your game is, but if you want to keep your little act up so be it. Men like you dream of girls acting like the way you do, just so you can treat them like objects. I don’t know if this is you trying to show Amanda how you would want her to act like or what, but I’m not pretending with you that it isn’t what you want.” Bailey’s eyes grew wide and started to tear up, his emotions flaring. Her words hurt him like a physical blow, she didn’t believe him and he didn’t know why she would think he would want to be like this. “Till this is over you will be nothing but Bailey Ann Best and I don’t want to hear one word out of your mouth to contradict that. You want to act like a bimbo teen girl, so be it.” The tears still welling up in his eyes, Bailey shook his head. When she said he could drop the act it felt like he was given refuge from a raging storm, a place to be safe. Now she was pushing him back out like he was some lepper. “Don’t you shake your head at me, I believe part of being a good girl is not arguing. I don’t want to hear a peep out of my bosses boyfriend if he can’t be honest about his motivations, so you are just her sweet girl, her sweet but dumb daughter. Now dry your tears before you ruin your makeup.” April opened the middle console and pulled out a few tissues and handed them over to Bailey. She took in the sight of him again before letting out a long sigh and pulling back out onto the street.

Bailey pulled the sun visor down and looked in the mirror as he dried his eyes and checked over his makek up. He didn’t say a word, afraid of her snapping at him again. Bailey had never been afraid or even intimidated by her before, but her going off on him like that was more than enough to cow him right now. A few thoughts bubbled to the surface of telling her exactly where she could fuck off too, but they never went far. His brain thinking of what would happen if he wasn’t a good girl. He was supposed to act a specific way and while he never thought April and Aunt Megan were friends, when he saw them having coffee together at the mall it had him rethinking that conclusion. If word got back to her, he could be in trouble. She might spank him for it, or some sort of sexual punishment. One horrible thought did come to the surface of his mind, he imagined April pulling him over her lap to spank him like an unruly child. He already had two women that were once his peers do it to him, he didn’t need a third. “So, you and August huh?” Bailey looked over to April, not sure he had heard her right. She didn’t sound angry. “What?” He asked not sure exactly what she said with his focus being split already between his worrying and looking in the mirror. “My brother is more than excited to be dating you, I bet you are excited to be dating someone older than you.” Older than me, older than me.. I’m four years older than him! Bailey wanted to scream, but instead all he did was nod his head. “Aww you don’t have to be bashful, you can admit you like him. I do recall seeing you kiss him and he can’t stop talking about what you can do with your lips. Not that I want to hear my little brother talk about such things, especially about my boss's daughter.” April said thinking about seeing him kiss Bailey at the park and how he wouldn’t stop talking about kissing Bailey on their first date. What you can do with your lips, those words caused Bailey to blush bright red and he tried to hide his face in his hands so she wouldn’t see the embarrassment and horror that she knew what he had done in the movie theater. No wonder she wouldn’t believe him about not wanting this if her brother told her that he got a blow job. She knew about the literal worst moment of his life and maybe she reacted the way she did because he didn’t tell her what really happened. “Miss April, let me tell you what happened.” April shook her head and gave Bailey a small smile, seeing the girl pull her hands away from her still blushing face.

“I don’t need to hear about what happened on your date, nor do I want to hear about it. Save that for your girlfriends.” He needed her to understand that it wasn’t what she thought and he needed her to keep it a secret. The idea of anyone at all knowing he had a dick in his mouth let alone that he swallowed cum was more than he could bear, but when he tried again she only told him. “Bailey, I don’t want to hear it.” Bailey closed his eyes, feeling the weight of the long lashes as he whispered back to her, his request. “Please, you can’t tell anyone, I would like just die.” April almost laughed at how dramatic Bailey was being, but if he didn’t want her brother to kiss him, then he shouldn’t be acting like a bimbo. As much as it disgusted her that Bailey acted this way, it was worse that her brother was drawn in by it. She thought if little Bailey didn’t play so hard to get, that maybe he would lose interest when he realized how superficial it all was. “Sure, why not.” Bailey snapped open his eyes as hope filled him as he looked at her. “Really!?” Smirking as she gave Bailey the side eye. “I don’t see why not if you promise to no longer play hard to get with my brother.” With a hard swallow Bailey nodded a little afraid at what she was really asking. “Hard to get?” Bailey could see April roll her eyes at the question. “You know exactly what I’m talking about, I know you aren’t as smart as your Mom, but you know what I mean.” It felt like the bottom of his stomach fell out as he thought about it. He did know what she meant, but he was hoping she meant something else, anything else. She was offering to not tell anyone about giving her brother a blow job if he kept giving them to him. He had to decide what was worse, giving a blow job in secret or everyone knowing he did it. “Okay, I agree.” He said in a small voice, thinking how no option was good, but the love of his life finding out he swallowed another man’s cum would be too much. There was no way she would be able to see him as a man if she knew he had done that. “Don’t be so glum, a girl like you is supposed to be happy and smile aren’t you?”

April looked over at Bailey to see the feminized man smiling back at her. “Good, just like that. Why don’t you send my little brother that photo you took earlier and tell him you are thinking about him. That way he knows he is on your mind. In fact I think he would like it if you were constantly messaging him for attention. A girl like you likes getting attention from a boy she likes right?” Bailey swallowed his saliva again and nodded before pulling out his phone again to do as she said. The sun hadn’t been up for long, but it was already a horrible day. “Good, while you do that I think you should know what doctor's appointment we are going to now that we are close.” Bailey hit send on the text with the image of himself with April before he looked back to her. He had completely forgotten about their destination with how the conversation had been going. “I have found a clinical trial that is owned by Mega Corp, they are testing a device that will help you pass more easily.” The fake smile felt much more genuine when she said that. If he could pass easier maybe he would worry less and he could stop over acting how feminine he was.. Though he doubted Aunt Megan would allow that. “You my dear are going to be getting your very own vagina, isn’t that exciting!?”