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Chapter 160 by Nicegent42
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A bad days lesson
Walking down a row of cubicles Bailey glanced down at the post-it note with a list of names that Brannon had given him and then looked back up to a name plate near the opening of one of the cubicles. “Knock knock, Mr. Caddel!” Bailey said, sticking his head into the cubicle with a big smile on his face. “I’m like just coming around to pick up a report for…” Bailey looked back down to the post-it note again. “Account… Teaten? Sorry, it is a little hard to read. Oh and I’m Bailey, one of the new interns! I will be around for a bit helping Mr. Brannon and… Is that a video for TitanFall!? It looks totally fun! I have only seen the trailer but it looks… I mean OMG you get to get in a giant robot!” Bailey said with genuine excitement. He didn’t often buy video games when they first came out, never wanting to have to wait in line or deal with places being out of stock and waiting always allowed him to look something up if he ran into trouble. This was one of those games he had been excited about, just hadn’t had the opportunity to pick up and had been forgotten till this moment.
Swiveling in his chair the twenty three year old Caleb Caddel moved his attention away from his phone where he was watching some game play from a youtuber to the overly excited green eyed girl. Once seeing her a smile spread across his face as he took her in, much of his focus being on her low cut top. “It is.” He said clicking the power button on the side of his phone to turn off the screen. “You said your name is Bailey?”
“Yep!” the feminized man said cheerfully, not picking up on where the seated man in front of him was looking as he made a mental note to pick up the game with his first paycheck. The thought of buying TitanFall reminded him how he also would need to also hit Sephora to resupply some of the products he used daily.
“You don’t need to call me Mr. Caddel, that sounds so formal. You can call me Caleb, it is nice to meet you. Honestly not a lot of people around here with good taste like yours. If you like after work you could come over to my place and we could play and maybe order a pizza.”
“Hmm?” Bailey made the sound blinking a few times to refocus and come back into the moment after his mind went down the rabbit hole of makeup products he would need to get. “I’m sorry I like umm space out sometimes, I can be a bit of a ditz. What was it you said?” Being left to his own devices growing up Bailey often would zone out to consider something, it had gotten worse when he had to pretend to be something he was not. Asking himself what a girl would do in a situation, what she would say, would it be different if said girl had less than a hundred IQ. He was aware of what others thought about him when he did it, but as Bailey Ann it played into the role and over the course of the last few weeks he had gotten worse about doing it. As time passed he had to contemplate how to act as a girl less and less, but letting his mind wonder so often from what was happening had conditioned himself to keep doing it.
“I was just asking if you maybe wanted to come by my apartment to play TitanFall after work?” Celeb asked, knowing the game only allowed multiplayer online.
The image of a giant robot crashing down to the earth and climbing inside to shoot rockets around filled Bailey’s mind filling him with an excited glee. It didn’t just sound fun, but also an escape from his current feminine life. He had doubled his efforts to submerge himself into being Bailey Ann, but new game gave him a different avenue of escapism. The joy that came over him showed in his body, acting to the offer much like Candi would to something she was excited to do. Bailey Bounced on the balls of his feet, a large smile coming to his lips. The movement causing his feminine chest to bounce, something Caleb was happy to see.
“Oh my god! I would love to!” Bailey said before a pout came to his face as he blew some air out heavily through his nostrils. The sad expression stayed only for a second before moving back to its normal resting grin. “But, I like can’t. I already have plans.” Playing the game sounded fun, but tonight was Bailey’s last night at Aunt Megan’s house and when she came home she would be not just telling him all about what she did to Liam, she would show him with the video camera she was going to set up and he just couldn’t wait to see his **** come to life.
With a shrug and a nod Caleb accepted the rejection, turning in his chair slightly to pick up a stack of files that the hot girl had been asking for. “I get it.” He had been so excited, his hopes soaring when he saw how excited she had gotten at his offer, but he should have known better than to get his hopes up. “Can’t blame a guy for trying to ask someone as pretty as you out when he gets the chance.” The young man said, holding out the stack of his work. He felt a small pang in his heart as he saw the girl smile at him as she tilted her head to the side and flutter her lashes.
‘He was asking me out!? No, no, no, no I’m not going on a date with another guy! I have enough… oh it would be so funny if I set Liam up with a date with another man. That would be perfect!’ Bailey thought, as he took the paperwork. “I’m like sorry Caleb, but I have a boyfriend. You seem like a great guy though, maybe I can set you up with a friend sometime.” Mentally Bailey pumped his arm, happy that Auggy was coming in handy. He wasn’t sure if setting this guy up with Liam would really work or even if the smaller man would be passable, but it seemed like a good way to let him down easy.
“Really? Yeah that would be great and I get it, no way someone like you wouldn’t have your pick up guys and beating off the rest with a stick.”
“I would rather use a robot titan!” Bailey said, giving the guy a wink and wishing he really could just bash guys in the head with a two by four. “Well, I like have to get going. I was like super nice meeting you.”
The conversation with Caleb had Bailey imagining the things he could try and do with Liam. Make him paint his fingernails and toe nails, watch a few rom coms, but not the good ones that he had watched with Candi. Walking into the office to deliver the files a big smile crossed Bailey’s lips, thinking about how his aunt had made him jerk off while looking at a picture of Chuck and sucking on a dildo. That was the exact right type of punishment he wanted to give to Liam, that and maybe use his first paycheck to buy one of those dildos on a piston and leave him tried up while the machine fucked him for a few hours. ‘Do I make enough to buy that?’
Not focusing on anything around him, Bailey's heeled foot hit the wooden leg of one of the chairs in front of Brannon’s desk. The minor collision caused Bailey to lose his balance, toppling off his heeled feet and down onto his knees at the side of the desk he was trying to walk around. The tumble didn’t hurt, but it had caused all the files to be scattered across the floor, their contents both spilling out and mixing. “Oops!”
Jumping to his feet George slammed both of his palms down atop his wooden desk, as he looked down at the girl on the floor that was now covered in a mess. “Oops!? Look at what you did, you silly bimbo! Do you have any idea how long this is going to take to get sorted!?” Brannon practically growled at his inept intern. Stomping his feet he moved around to the side of his desk, grabbing the girl by her forearm to pull her up to her feet.
“I’m sorry… I… tripped. It was an accident.” Bailey only glanced at his face, looking away from the hard angry expression. Biting his plump lower lip he looked around, he would have immediately started putting things back in order, but Bailey had no idea where to begin, or what should go where. ‘No, no, no, no, no.’ The word echoed in his mind as his eyes darted from one piece of paper to the next, hoping to see something with page number, a title page, anything to start sorting things out. Brannon was upset, down right furious if the grip on his arm told him anything and he was the one that held the future in his hands.
“An accident… wipe that smile off your face… in fact I know exactly how bimbo’s like you learn their lesson.” His hand still gripping the girl's arm he pulled her over to his desk, having no problem pushing her down onto it, bending her over the side of the desk, her practically tripping in her heels from the sudden movement.
“What are you..? Oof!” The air was pushed out of Bailey’s lungs as he was thrown down onto the desk, his breasts pressing hard onto the wooden surface as the balding man’s hand pressed firmly on the small of his back to hold him in place. “Let go.” The words coming out hardly audible when Bailey tried to talk after getting the air knocked out of him. That was when he learned exactly what the man meant by learning a lesson as a sharp pain came to his rear.
SMACK
SMACK

After the second slap to the girls white skirt covered ass George leaned in closer. “Girls like you need to be spanked to understand how naughty they are.”
Bailey’s eyes had gone wide when he felt the first attack to his rear, he gritted his teeth feeling the second, his legs kicked in the air and into the side of the desk as the man held him in place. While being disciplined in this manner hadn’t really been done to him growing up, Bailey Ann had experienced it a few times from her aunt and mother, but having this done by another man and done in an office was something new, something worse. “Stop!, Stop, Please!”
SMACK
“You want me to stop? Then tell me you will be a good little bimbo from now on.” George left his hand on the girl's ass after the last slap, cupping it with his hand.
“What?!” Bailey asked, shocked by what the creep wanted him to say.
SMACK
SMACK
SMACK
“Ow, Ow, ow, PEACHES! Please…” Bailey begged, feeling tears coming to his eyes.
“Just tell me what I want to hear, little Best. You are sorry aren’t you?” George smirked, he had done plenty of things to and with girls under him in the past, but this was the first time he spanked a girl, or at least the first time he wasn’t paying someone for the privilege. The girl represented her mother, a smug woman that didn’t understand her place. She would soon, but first her daughter would learn.
“Yes, yes! I’m sorry! I just fell down, I swear like I didn’t mean to!” The thin fabric of his panties and skirt did little to protect him from the man’s hand. The blows were more painful than what aunt Megan gave individually, leaving his rear throbbing after each blow. While it did hurt the pain wasn’t anything normally tear inducing, the act of him feeling powerless again had sent his mind into a tailspin.
SMACK
SMACK
“What you meant doesn’t matter girl, what you did and do in the future matter. Now tell me you know that you are a little blonde bimbo.”
Bailey’s bottom lip quivered, but quickly it changed as he grit his teeth once more as another slap came to his rear. “I’m a little blonde bimbo, please stop!”
“A little bimbo that likes to tease me, don’t you?” When Brannon said that a rhyme came to Bailey’s mind that he hadn’t said in a while about liking to tease and getting down on his knees to please. When Bailey didn’t answer right away he felt the ninth slap to his rear.
“Y… yes, yes I’m a bimbo that likes to tease you.”
“See that wasn’t so hard was it, little Best? In fact I’m betting getting that out in the open feels pretty good. Now tell me you will be a good girl for me from now on.” George commanded.
“I.. I…” Bailey swallowed the saliva in his mouth. “I will be a good girl for you from now on.” Soon as the words escaped Bailey’s lips he was helped back to his feet, though it was an awkward position. Looking down Bailey slipped his foot into one of his white heels that had fallen off when he was kicking his feet about.
“You look a mess girl, why don’t you scamper off and make yourself look presentable and then you can come back here and clean up your mess.”
The man didn’t need to tell Bailey twice, quickly as he could he pulled open the door and rushed off to first his cubicle to get his purse and then the ladies room. Standing in front of the mirror Bailey used some wipes to clean up his face, washing it. He felt like curling up in a ball and crying, the throbbing from his rear was mind compared to what he felt inside. Being bent over like that, powerless brought back the hazy memory of his legs being held apart by a metal bar, while his hands were tried behind his back by a belt while he was fucked… fucked by another man, someone he once counted as a friend.
Ragged breaths came to Bailey, his chest heaving and even though he was wearing such a low cut top and was looking in a mirror he took no notice of how his breasts moved. All of his focus on his own face, his own eyes. Calm came slowly, but as Bailey started to reapply makeup, things settled. After fully cleaning his face Bailey started with primer, then foundation, adding concealing and by the time he was adding blush his breathing was back to normal. The simple routine calming his mind. The sight of himself when he came into the bathroom had somehow made him feel worse. Adding eyeliner and eyeshadow he started to feel more like himself and then by the time he was putting the cap back on his lipstick he was back to smiling.
The routine didn’t change what happened, it didn’t fix anything, but it did allow him time to think. Time to move on to his next steps, to remind himself he needed to be happy, a happy girl had less to worry about.
Now looking in the mirror Bailey turned his head to the side, pulling out his phone for a bathroom selfie, not really thinking about what he was doing. Only what he was about to do, he was going to have to go talk to Miss April. This guy couldn’t get away with what he just did, he couldn’t believe the balding creep had the nerve to do it. The nerve to make him say he was a bimbo that wanted to tease him. The man had to be stopped.
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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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