Trouble?

Dear diary it's like me again hehe

So today I like got to hang out with my big sister again ^^ and after all the shopping we did I totally had the perfect outfit! It was a super cute blue blouse with these like ultra cute sparkles on it then I paired it with a cute little button-up jean skirt that shows off my gorgeous legs! Then of course stilettos because who wouldn't wanna be drop-dead gorgeous?

When Mommy came in she even said I look like a princess^^ oh like this morning and like last night too Mommy brushed my hair out and it felt sooooo good.

So like when I was all done Mommy said me and Candi could be twins! Like wow I know Candi would just flip if she knew. I almost did hehe

On the way, me and Mommy talked about my dream wedding cuz of this quiz Candi sent me. What your dream wedding says about who you will marry. So its like no surprise Im going to marry a romantic and adventurous man. I wouldn't want to be stuck with some boring unromantic guy! Blech!

So like when I got to Candis room she totally tackled me and said I looked totally hawt hehe but she was totally cute herself and she had this soooo cute white bikini and black sarong. She knows as much about fashion as me. Probably more. Hehe but probably not.

But hey Im like no slouch in the bikini department. I dressed in a red and white striped bikini that showed off my fab belly button ring hehe

And she like totally remembered I burn easy in the sun :( and she like got the perfect lotion for us. And shes so clever cause she put this totally cute star sticker on my side so like it wouldnt tan but the rest did! I always loved looking at the stars with my Daddy

So then like after we got done putting on our lotions and I got to have the best nap there was this sweet couple and their totally adorable son and they asked if we could babysit so they could have like some alone time. I think that means they were going to go have sex hehe. I cant blame her her hubby was cute.

But any way like Mikey was so cute and adorable. We played lots of games until the poor thing was all tuckered out and he like totally clung to me. When his Daddy came to get him I was like so sad to see him go he was so cute and sweet like im not saying I want kids right now but maybe some day. But like Candi even said id make a great mom one day. Im sure Mommys not in any hurry to be a grandma hehe

So like while little Mikey was hanging onto me we took another quiz its scary how accurate these quizes are to! Cause this one said I like like dressing to the nines and like duh obvi! Its so much more fun than when I was a boring tomboy.

And Candi is like so easy to talk to. We like talked about my daddy and my horse cherry from when I was a little kid. she talked about her mom. I felt so sad cause she like misses her mom so much and honestly...I miss Daddy some times. I bet he would be like so totally surprised with how his daughter turned out hehe

So like after we had lunch that was totally diet friendly of course I got to be on Candis channel again. And like my ponytail had come all undone so she put my hair in the cutest pigtails. I like fer sher looked like her younger sister then hehe. Any way on the channel we did makeup tutorials. Mine was basic since im still new to makeup. Like clothes are totally easier you just put on whats the cutest. But like makeup is an art so it was like totally hard cause I had to teach her viewers how to do the same look Candi gave me. Then after my part was done Candi showed them how to do a night time look. I got to be the model hehe being a model is so much fun! Can you imagine? People like get paid for being pretty!

Ooh Candi even helped me set up my own youtube channel idk why I havent done this before? My first video was like about my new diet so of course I wore my bikini. I know im like not where I want yet but come on im still totally hawt!

And like Candi sent the video to Auntie Megan and she loved it!

So with the money Mikey's Daddy gave us we could both get massages! Candi got a girl but I got this like totally hunky guy. I think he had a crush on me. And after we both felt sooooo relaxed we like totally crashed on the couch idk how long cause like her Daddy woke us up. I like didnt want the day to end but he had to drive me home i hope I get my license soon. And like i was starting to miss Mommy any way

Sol ike when I got home tho Mommy wasnt home yet but Auntie Megan was! Im like so happy I get to spend more time wiOMG!!

Some guy came by and he is like totally flirting with Aunt Megan!

Ok like the guy is looking for Bailey. Not me bailey Mommys bailey. Its like totally weird Mommys ex has the same name as me. But like im the cuter one.

Omg again! He has a younger brother and like wants to totally set us up! I got like really nervous cause like ive never been on one date and now I like have 2?!

Okay so like confession time last night I was naughty and like forgot auntie put a block on my computer. So like I just wanted to see cute guys and stuff but she found out and I'm like totally dead if Mommy finds out! :((((

Taking one of the bottles of the berry smoothie from the fridge Bailey took a sip and made a face. It was better than the other green smoothie, but the kale sure didn't help the flavor. A few more sips before he let out a sigh and headed to his new bedroom, the clicking of his heeled sandals with every step. Sitting down at his very own vanity Bailey started to wipe the makeup off his face, watching as he saw more and more of his old self appear and yet with the outfit, pigtails, large hoop earrings and of course breast he wasn't sure anyone would think of him as he used to be if they saw him. With that done he started to undress getting down to just the white panties when he heard Mandy calling from the other room. "You almost ready sweetheart?" before opening the door and seeing Bailey standing there in white panties smooth in front from the tucking kit, breasts hanging free and still wearing the hoop earrings. She saw no trace of her boyfriend in front of her, making what happened earlier a little easier on her mind.

"You going to sleep like that princess?" Bailey looked to Mandy and then back down to his exposed breast, fake or not it was embarrassing. Covering them with one hand he went to the dresser and pulled the first thing he saw, the same babydoll nightie from last night, and pulled it on over his head.

Amanda saw the cute blonde standing before her red faced looking at the ground in her pink babydoll with a little boy in front, her hair in pigtails and the large earrings. "Come sit so I can brush out your hair sweetie." she said sitting down on the bed and patting a spot beside her. When he sat down, she took the pigtails out and started to brush it with the real hair brush and removed his earrings. "These are pretty sweetie, but you can't sleep in them." another blush came to Bailey's face, this entire thing was uncomfortable. The woman he loved was brushing his hair like he was her child... exactly what he was pretending to be and how he overlooked the weight of the earrings. The feeling of the hair actually being brushed felt heavenly, much like how the massage was with Hector earlier. It was odd to know something was wrong in his head, but for it to feel so good on his body. After maybe forty or fifty strokes through his blonde hair Mandy smile and wrapped her arms around him from behind. "There all done princess. "Now time for bed young lady, you had a busy day."

Amanda tucked Bailey into bed, pulling the sheet and blanket up and put the teddy bear under his arm. "Good night, I love you baby." she said kissing him on the forehead before turning off the light to the room and closing the door.

Laying there in the girly room, Bailey puffed up his cheeks and blew out hard, causing his bosomed chest to shift. It was to have the affirmation that she still loved him, but the kiss on the forehead was not the type of kiss he wanted from his beautiful girlfriend. Nor did he like the throbbing on his backside from her spanking. He wasn't sure why Amanda liked being spanked in the bedroom, it just plain hurt. Bailey just laid there looking up to the ceiling reflecting on what went down today before deciding he would rather distract himself then go through that mess again in his own mind. Pulling his arm free of the stuffed bear he pushed the covers down and leaned over to grab his laptop from the nightstand.

Opening a web browser, he went to click on one of his favorites, but stopped just before clicking on the link remembering what happened last time and the repercussions he was still feeling on his rear. Thinking she may have that on lock down, but he still had his hidden folder of pictures. Clicking on the folder icon he clicked on one of the most accessed folders titled 'Fonts' to get to his porn stash. Inside though instead of busty babes, lesbians going at it was pictures of large men with their cocks hanging free and hard. One of them showed a muscle head man having a girl bent over pulling back on a leash attached to a collar she was wearing as he took her from behind.

"Ugg.. Guess she found this too, fuck." he whispered closing the folder. With some contemplation he opened the folder Megan left for him, they might be the point of view of the girl looking at the guy as she goes at him, but he could still see their breasts. It would be enough for him to get off he thought. Turning the video on, Bailey reached into his panties and stopped, realizing with Mandy coming in the room before he never untucked, the kit was still holding him in place. The video played as he tried to peel the pad back without getting out of bed, but before he could the bedroom door opened. Bailey could only see the outline of Mandy from the light from the other room.

Amanda was moving between the living room and kitchen cleaning up from the day, still dressed as she had from work minus the heels and blazer. When she was considering what to eat, she saw a light from under Bailey's door. Walking over she threw open the door and saw the blonde teenage girl with a laptop to her side showing the point of view of a woman giving a muscular man a blow job, while Bailey had one hand reaching into her panties. "Bailey Ann Best, I don't think so young lady." Amanda walked up and slapped the laptop shut and pulled it from the bed. She saw the wide-eyed stare of her temporary daughter.

"You were told to go to bed, you are just asking to be grounded or another spanking. Now do as you are told and go to sleep.'' The feminine name cut through Bailey the way she said it with an elevated voice, he was too shocked to respond before she was gone with his laptop leaving him in the dark with one hand down his panties touching the edge of the kit that he was unable to pull off with any quickness from the long nails. Pulling his hand out he slapped the side of the bed in frustration, she was doing what he literally asked her to do.. Keep in line like her child, but never figured she would stop him from jerking off. He sure as hell wasn't going to sleep in the kit so he started to get out of bed to get it off when he heard Mandy yell from the other side of the bed.

"If I open this door and you aren't in bed with your eyes closed you are getting another spanking miss!" glaring at the door he wanted to tell her this was all over, but stopped letting his mind rule instead his emotions and climbed back into bed and pulled the covers up angrily. He wanted to defy her and just stay awake, his mind imagined how he would show Mandy who was boss when he was not having to pretend to be some prissy girl in heels and makeup. Despite his best effort, sleep soon won the battle and his body drifted off into slumber.

Bailey awoke to Mandy brushing some of his hair behind his ear, she was smiling down at him holding the best mom ever mug. Blinking his eyes sleepily he remembered last night and smiled up at his love hoping to get on her good side. "Morning mommy." he said in the best innocent voice he could manage through his sleepiness. "Good morning princess, time to get up to get ready for the day." she said, giving him another kiss on the forehead before leaving the room. Getting out of bed the very first thing he did was pull the tuck kit off, he wasn't sure if keeping himself like that for too long caused a problem, he just knew he didn't want to find out.

Taking the two pills at the start of the day, one for energy from Candi and the other to control his erections from Megan, he considered what was ahead of him this Tuesday. Tonight, he had what might be the worst thing so far of this little role he is playing, but today he could just relax and maybe have a few drinks without a teenage girl, his girlfriend's boss or the queen bitch getting in the way. He figured he would put on a good show of being the good daughter till Mandy left and he could have the rest of the day to himself. With glee he bounced off to the shower for a few a few steps like some excited girl, but stopped a few steps out of the room feeling the bounce of the C cup breast in the babydoll.

Washing himself quickly Bailey rubbed some of the lotion on his legs and arms after patting himself dry and blow drying his own hair, he left the bathroom with the towel up covering his breasts like Mandy had now repeatedly show him now. Getting dressed for the day he used his kit to tuck and then slipped on some lacy black thong panties and black pushup bra. A glance in the mirror made him think it would be wise to take an extra pill, best to be prepared now for tonight because he was sure Candi would be dressed to kill for the date. Next, he pulled out some black tights with a pattern on them to help keep warm being in the air conditioning all day, a black pleated skirt that caused him to sigh when he saw the little bow in front. Then it was a sleeveless white shirt and some black strappy heels that looked like they might be five inches tall. While not something he wanted to wear, he wanted to make sure he looked like he was committed to the role to not get a repeat of last night and maybe bring a smile to Mandy's face instead of the angry look he saw last night.

Moving over to the vanity Bailey added the hoop earrings, eye liner, mascara and some of the lip plumper lipstick that he hated. The tingle and swelling in his lips couldn't be a good thing to keep happening he thought. Turning his head from side to side to make sure he did a good job Bailey smiled at himself, proud he was able to do it himself. The feeling was short lived when his mind caught up with why he was proud of himself. He pouted just briefly, but stopped when he saw his reflection.

Last thing he needed to do was brush his hair with the hair brush. Pulling a section of his blonde hair to the side, Bailey was brushing it out when Amanda came in to see her daughter getting ready for the day, looking to be the paragon of femininity. "You did a wonderful job princess, I think you are missing just a few things, I will be right back." Bailey wasn't sure what she was going to get, but he was sure he wasn't going to like it. Coming back into the room Amanda was smiling like it was Christmas morning as she ran some of her fingers through Bailey's hair pulling one side back before adding a leaf and flower hair comb, and then clipping a necklace around his slender neck that was in the shape of a heart with a rose inside. The necklace was one of the first gifts Bailey had given Mandy, he wanted to show his feelings for her and have something personal with her middle name being Rose.

"Just look at you, pretty as a princess Bailey, you have no idea how happy this makes me." she said hugging the sitting disguised man from behind. This was the exact mood Bailey was hoping for, he just wished it wasn't him looking back in the mirror looking the way he was.

With that Bailey watched Mandy leave the bedroom, seeing her in a tight dark skirt a few inches above the knee, tan hose, nude three-inch heels and a cream covered frilly blouse. He enjoyed watching her ass move as she walked and wished he could show her how virile of a man he really was and come up behind her for some morning sex before work. Standing up to follow her the thought vanished from his mind with the first sway of his hips in the tall heels.

Coming into the living room Bailey watched Mandy touch up her lipstick before turning to look at him, her smile was gone, but she still seemed to be in a good mood. "Listen princess, after work today Derrick will bring Candi over so you can get prepared for your date. I am sure you are nervous, but you should be able to get away with just holding August's hand. If he goes in for a kiss just turn your head, I bet you do not want a repeat of the picnic. You will be fine, I promise. For today though I have a list of things for you to get done when you are alone in the house." she said, handing a hand written note to him.

Looking down at the paper a few things were written in pen.

Tuesday: vacuum carpets, sweep floors, laundry, iron clothes

Wednesday: Water park

Thursday: vacuum carpets, sweep floors, mop (Swiffer) floors, clean bathrooms.

Friday: Dust

Every day: make bed, pick up trash or clothes from floor, help clean up after dinner.

"Chores, you are giving me a list of chores to do?" Bailey said blandly. Putting her purse on her shoulder Amanda smiled looking at the pretty teen. "I am done being the only one to clean up around here. I may be your mother, but I am not your maid. Now I have a cute apron that you will recognize for you to wear while you clean up around here, I do not want to see you getting stains on those clothes or having the tags pulled off because you were careless." she said walking over to the side of the fridge and handing a frilly apron to Bailey.

"Do I make myself clear?" She said sternly seeing the reaction Bailey was giving her, the same type of attitude when he would say he would do something when she left for work, but then have to do it herself when she gone home. "Yes, mommy." Bailey said putting on the apron over the outfit he chose earlier. Looking down at the pretty thing he had got it for Mandy in hopes of finding her wearing just that and some heels one day so they could have some sexy fun in the kitchen, but he wasn't sure if she ever wore it... the thought made him wonder if he was the first person to wear the frilly thing.

When Bailey was alone, he grumbled to himself and looked down at the list thinking he should knock it out before he relaxed for the day. He decided the vacuum would work fine by itself and to not bother sweeping, what was the real difference anyways. It was about two hours later, Bailey had vacuumed the entire apartment, skipping the sweeping in favor for the quicker method and found his laptop sitting on Mandy's dresser that he shared with her just a few days ago. Tossing it back into his new room he moved on to other chores like starting the laundry and taking out the ironing board. With this being the last thing on the list and having to wait for things to wash and dry he knew he had some time to kill. So he left the apron on the ironing board and went back to his room to open his laptop.

Laying down in the bed, legs spread wide and still wearing his heels, Bailey queued up the video from last night. Running his hand down the pantyhose covered leg was a thrill, he always loved touching a woman's legs in stockings and now he knew what it felt like from their side, it was wonderful. The video started to play and he could feel himself starting to get hard and was about to pull down both the hose and panties to untuck himself when a hard knock came to the front door. "Aww, come on.. For fucks sake I needed this." he said to himself in aggravation.

Even in his anger the training held true for his sexy walk Megan had instilled in him. The rage did prevent him from thinking about using the peep hole to see who it was and opened the door to see a man in a police uniform.

"Good morning honey, I have a few questions that I would like to as about a..." the officer said looking at a notepad. "Bailey Andrew Smith, would you mind if I come in and speak to you or anyone else here about him." the idea of a police officer looking for him was a surprise to Bailey, the point of all this disguise and act was to pretend to be someone else, but it was still a shock for someone to ask for him.. To him. The door was still being held open and no reply the officer took as an invitation. Walking into the living room he looked around, seeing one bedroom open to what looked to be a girl's room another down the hall to a master, but an ironing board open between them and it with a frilly apron laid across it.

"This won't take bit a minute little lady, sorry to interrupt your housework. Like I said I'm looking for a Bailey Andrew Smith, this is his last known address and it looks like his last transaction from the bank was to order the services of Candy's Care Services." the officer kept talking, but Bailey started to panic. Prostitution in the state was only legal if you went to a brothel. His mind first went to Megan for outing him, but figured it wouldn't be her or he would have heard from Mandy about it by now.. But then he remembered the last thing Candy told him after Megan showed up, how he was not to call her ever again. What if she told about her clients in some sort of plea deal, shit if the officer figured out who he was and took him in now looking like this he would be eaten alive or be beaten to death. In the panic Bailey missed the officer saying how a friend of Bailey's had filed a missing person's report as no one has heard from him and his phone was no longer being used by him.

"Umm like no officer, I like don't know anything about my mommy's ex-boyfriend. Is there anything thing else I can do for a handsome man like you?" he said batting his eyes at the man, hoping the overly girly act and light flirting might get the man to drop the issue and just go.

The police officer smiled at the pretty young thing fluttering her eyelashes at him flirting with him. He had seen it plenty of times, woman and girls sometimes had a hard time resisting a man in uniform. He had met plenty of badge Bunnys in his short time on the force, he just had to check something really quick with her saying mommy. "What is your name, for the report and your age."

"Oh, umm like funny enough I'm like also Bailey, but I'm Bailey Ann Best and I'm like eighteen now." the officer nodded, writing it down in his notebook, thinking how emasculating it would be to live in a house that had a girl like her with the same name.

"You have the same name as the missing person, fascinating." he was sure the name fit much better on her than who he was looking for, but to Bailey the phrase felt like a spike of dread like the officer was on to him. Racking his brain, he figured if he could get him to think with a different part of his body like he did every time he interacted with a hot girl, he might be distracted enough to not put two and two together. Stepping forward to be in the man's personal space Bailey was eye level with the man in his five in heels and smiled at him and reached up to touch the nameplate.

"I don't look much like a boy do I, officer Cooper?" his hand shifting over his chest to touch the metal badge." The man coughed a little, looking into the girl's pretty green eyes.

"No Bailey you do not.. At all." with her so close to him and all alone in the apartment he was sure what this little badge bunny wanted and started to lean forward to kiss her when his walkie talkie chimed in for him.

"Sorry Bailey, I would love to stay and get to know you better, but I do have to take this." he said pulling out a business card that said 'Officer S. Cooper' and his phone number on the front and a cell phone number written in pen on the back. Placing the card in Bailey's hand the officer leaned forward and pressed his lips to who he thought was a beautiful blonde young woman. The kiss was short, but much longer than Bailey would have liked. When the officer pulled back Bailey just looked at him stunned dropping the card to the floor. To the officer it looked like a young girl getting weak in the knees.

"Call me Bailey, soon or I just might have to come around again." he said laughing with how happy he was and winked at the girl before heading out.

Slowly walking to the door Bailey locked it feeling numb, he was successful in getting the police to leave and not suspect him. Though it cost him getting kissed by the man and he wondered what kind of trouble with the law he was in for using Candy's services more than once. If he had to go to court for it, no way could he hide that from Mandy. Leaning forward, Bailey banged his head on the door a few times before going and picking up the cop's card, last thing he needed was Mandy or Megan finding that. Going back to his room, the laundry forgotten, Bailey just closed the lid of the laptop not feeling in the mood now that a man had kissed him and just sat alone for a few moments. The peace didn't last, the chirping of his phone caught his attention and when he looked, he of course saw it was Candy. She had been messaging him all morning and he hadn't responded. Picking it up he started to answer the girl and tell her what he had been up to and talk about the upcoming double date she was so excited for.

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 torture 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 Mandy, who 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's 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 hanging down lightly curled with gold jewelry to offset 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?" Then it was Candi's turn to answer as Bailey only blushed, looking at 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 a 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 of her." Derrick tilted his head, looking at Amanda and then back to his daughter standing next to Bailey.

"Mega Corp is better off the more it listens to you, I suppose I could be too. Candance my dear, you have an inner beauty that the stars 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 all you that. I love you!"

Clapping his hands together Derrick looked at the two girls in burgundy dresses. "Alright then, do you both have at least a twenty-dollar bill on you just in case of emergencies in those little purses?" Bailey opened the little purse and saw a few things of makeup, the pink house key, a tampon. Not seeing any money in it he thought back to his own wallet not sure the last time he saw it, but knew there wasn't any cash in it even if he found it, so he shook his head. "We went over this earlier, daddy, I have money if I need it." Seeing her daughter shake her head after looking Amanda nodded, "hold on dear." she said going through her purse and pulling out her wallet, only seeing a few dollar bills and frowned.

"The question was for both you Candi, just in case the two of you get separated. Don't worry Amanda, I got it." he said handing Bailey a twenty-dollar bill from his wallet. A grown man handing Bailey money to be safe on his date with another man, he was sure the night could get worse and didn't dare think of how less the universe conspire against him.

"I should have had some money available, thank you for loaning Bailey some money tonight. I will make sure to pay you back at the office tomorrow." Amanda said hanging her purse back on a kitchen table chair. "Nonsense, I am happy to help give Bailey a little extra safety for the night. The girls, wait I'm sorry the young woman will help keep each other safe tonight and any help to one is help to both." Bailey saw his girlfriend make eye contact with him and nod trying to indicate what he needed to do. Taking a deep breath Bailey smiled at the older man. "That is like totally nice of you Mr. Connors, you have been like really nice to me and mommy. Can I do anything to like thank you?"

"Tell you what, why don't we get a few photos I think that will be thanks enough. Some of just the two of you girls, some with the four of us and then the two of you with each of us."

Over the next few minutes, the four took a few photos, the girls at Candi's insistence did some posing, like standing back-to-back each holding up a compact mirror fixing their lipstick. A few shots were taken of the four of them with a selfie style holding a phone up and a few of setting the camera app on a timer. The last sets were both the girls standing in front of Amanda her wrapping her arms around each of their waists, then one of Derrick holding them with his arms around each of their exposed shoulders. Bailey started to complain at one point, but it was taken the wrong way. "We have taken like a lot of photos, maybe that's like enough." he meant it as a gentle statement not a question, but when he said it, Candi bumped him with her hip. "Patience girl, the boys will be here soon." she said smiling at Bailey.

The date hadn't even started yet, he was still home and already Bailey felt like he needed a break. The day had been draining on him and these heels were already hurting his feet. "I will be like right back." he said mincing off to his bedroom to get a second to himself. Feeling as drained as he was Bailey took one of the vitamins Candi said would give him energy, and he figured if he was taking one pill why not the other just in case Candi started to all touchy with hugs, the last thing he wanted was an erection looking like this. "Oh… My… God! This room is like so you Bailey!" Candi said from behind him, having followed him over.

"Thank you... Ms. Gates ahh, my mommy's assistant had it done for me for like my birthday, so it is all still new." Candi looked around the room and was happy to see the little horse figurines placed around a section of Bailey's dresser. Glancing over at the bedside clock Bailey realized Ryan and August still wouldn't be arriving for twenty minutes and wasn't keen on the idea of spending that time alone with Candi in his bedroom or sitting out with Mandy and Derrick. The guy was nice, but he always made him feel like less.. Like he was small, a similar feeling to when Amanda called him princess. "Hey, umm sis I have to like tinkle. I will be back, you um make yourself comfortable." he said going off to the bathroom and locking the door behind him.

In the bathroom Bailey let out a sigh of relief and wondered how long he could get away with just staying in there away from anyone. Alone in Bailey's room Candi waited a minute before opening the closet and saw all the purchases from the mall, everything still had their tags on them. "She forgot to remove the tags, silly girl." Candi said to herself, giggling and deciding to help her friend and removed the tags so Bailey wouldn't have to while she waited for her friend to come back.

It wasn't long before Derrick's voice could be heard through the apartment. "Girls, your dates are here!" Candi came right out, while Bailey looked at the delicate gold watch and saw they were early, so he let out another sigh that his solitude had to end before joining everyone in the living room.

Coming into the room Bailey caught August's eye and saw his face light up as his eye trailed from heeled foot up to his eyes with a large smile on his face. August was wearing a pair of black slacks, a white button up shirt with the sleeves rolled up and a charcoal gray vest. While Ryan was wearing a pair of dark jeans with a burgundy button up shirt button up shirt, Bailey was sure he only wore it because Candi told him what color her dress was.

"Have a seat boys." Derrick said motioning for the couch so that when they the two sat down he was towering over them as he was still standing. "Tell me a little about yourselves Ryan, August. You are both young, what do you want to do for a career?"

"Daddy!" Candi whined, this not being the first time she had seen her dad play a power game to rattle her date.

"Ignore him, August we know each other, Ryan it is a nice to meet you. Can you tell us where you are taking out daughters tonight? Amanda said, giving Derrick a side glance and a tight smile. It was Ryan that spoke up first, him feeling less rattled from the older commanding man before them. "The plan ma'am is for me to drive us out for dinner to an Italian bistro. August planned out our timing.. We have just under an hour and a half once there before our movie starts. And then.." he was cut off by Derrick. "What is your driving record like Ryan?"

"I ahh, a good record sir, mostly. I have had two speeding tickets in the past, but no points on my license sir." the confidence Ryan first showed was starting to crack under Derrick's gaze. Amanda leaned over and whispered something in Derrick's ear. He looked at her and nodded but begrudgingly.

"Are you taking the girls back here after the movie or do you have another destination?" Amanda said smiling to try and calm the two down, and made eye contact with August. "No Mrs. Best, we planned to go have desert and discuss the movie after, if that is, okay?" Amanda placed her hand on Derrick's shoulder. "I am sure the girls will love that. Bailey, Candi make sure you send us a text message every time you are going to a new destination and when you arrive that way we don't worry as much about you two.

Stepping outside the apartment August placed his hand on the small of Bailey's back. "You look incredible tonight, I mean wow. You are the most beautiful girl I have ever seen, and that is saying something when you are standing next to your friend." Bailey's face became red, never had he been complimented like this, and he was not a fan. Bailey's heel caught in the space between two pieces of side walk and started to lose his balance and reached out for the closest thing to keep him upright, August. Who held the wobbling girl up right by pulling his arm around her waist and holding her closer to him. "Careful now I got you beautiful." he whispered to her, the words and closeness deepened the blush. "I umm didn't mean like to umm, thanks." Bailey mumbled looking at her date.

Laughing lightly, August smiled "If you just wanted me to hold you, you could have just said so."

Candi smiled and looked up and to the side, not turning to face Ryan. "Hear that, August thinks my sister is prettier than me. What do you think Ryan?" squeezing his lips together and furrowing his brow Ryan was quiet for a second. "I think you are trying to trap me and whatever answer I give to that would be wrong. So, instead I will say both of you are beautiful, but I for one feel proud you chose to spend even a second of your time with me, let alone find me worthy enough for a date." he said reaching out and holding his dates hand halting her progress to the car and turning her to face him so she could see his smile.

"Ooo, good answer." she said leaning up and kissing Ryan lightly on the lips before pulling back and biting her lower lip before giggling.

Back in the apartment Derrick sat down on the couch next to Amanda who had seated herself kicking off her heels soon as the girls had left. "Do you want to come back here when the girls are on the way home?" rubbing his chin Derrick stood up and picked up his laptop bag he had brought with him and brought it back to the couch with him. "Actually, I was thinking we could watch a movie, Candi recommended one that both of us might enjoy called Definitely, Maybe. She said it was about a divorced father talking to his daughter about how he ended up with her mother. Figured we could do that and order a pizza while the girls are out. Care to watch it, or do I have to go watch it by myself at the hotel?

Eyeing the man next to her Amanda smiled, she loved that movie and Bailey hated it. "Well, no one wants to watch a movie alone, you can watch it here so long as you let me pay for the pizza."

With a warm smile Derrick handed the dvd over Amanda. "You are right, no one should and I like that you are open to negotiating, but.. I have a confession to make. I may have accidentally already ordered a pizza and it could be already on the way."

"Accidentally?"

"You understand, sometimes you are just planning things, like just an example off the to of my head. Planning on watching a movie with a beautiful woman and you are looking at the different pizza places online to see what has the best reviews and your hand just you know, accidently orders one and by mistake type in your credit card number. Story as old as time." Amanda narrowed her eyes at the green-eyed man. "Depending on who you ordered from you might be leaving." she said pretending to be stern. "Gino's on Castle Rock drive, are they any good?"

"Fine, you can stay, but you are on thin ice buster."

The two back at the apartment shared a large extra cheese pizza while talking sharing stories about their daughters. Amanda stuck close to the truth when she could and steered things toward the made-up identity when she had to. Amanda was amazed at how close it sounded Derrick was to his daughter and how much he loved her, though she could tell it was a struggle to do it all on his own. Like tonight and how she felt she needed to step in.

Over at the small bistro Bailey smoothed his skirt out from under him as August held the chair out for him. The man was acting as a gentleman, holding doors open for him, not even letting him open the car door for himself, but also taking every opportunity to touch him in some way. Placing his hand at the small of his back, or reaching out to hold his hand while sitting in the backseat with him. Though looking ahead at the couple in the front seat it looked like he was trying to take queues from his friend Ryan. Bailey could tell who was the alpha of the pair and then soured his mind thinking Candi was the alpha of the girls, making him feel so wrong. Bailey was small for a man, but he had always been the aggressor, the one picking up woman and here he was the one being picked up and he couldn't even claim to be the top dog in his new role, not that he wanted that title either.

Looking at the menu Bailey wasn't sure what to order, what he was even allowed to really order. Megan put him on some diet and Candi appointed herself as the overseer for it and then the fact that a boy was paying for him. A text alert popped up on his phone and while it wasn't good date etiquette to look at ones phone, he wasn't really interested in making a good impression on August. Looking down at the message is was from Candi saying tonight they should get the shrimp salad so they can splurge on a good meal without breaking their diet. He didn't consider any type of salad a splurge, and figured fuck it, I'm doing what I want. When the waiter came by Ryan ordered a New York strip steak, Candi got the shrimp salad as she said she would, August got the Braised lamb and when he saw Bailey lick her lips at mention of the meal, mostly because he hadn't had a good meal in days he spoke. "Don't worry, I can share." closing his mouth Bailey focused back on the menu more deterred than ever to get something he wanted and ordered the lobster ravioli. He considered getting a steak, but he couldn't remember the last time he ordered lobster and it just sounded so good wrapped in the delicious carbs and cream sauce. Ryan paid no mind to the others at the table beyond Candi who had his complete attention. Candi raised her eyebrows at her friend thinking it was bold to order lobster on a first date, and how the poor thing was going to have to work hard to work off that extra calories with her already working so hard to lose some weight. August however just put his hand on Bailey's nylon covered knee rubbing it gently with his thumb and whispered to his date. "I like a girl who isn't afraid to eat."

"Some girls like food." he chirped, moving his hand to push August's off his leg. But the second his fingers touched August's hand the boy took it as he wanted to hold hands and grasped his.

Looking over at his date Bailey smiled accepting the hand holding over the boy feeling up his nylon covered leg. The worse part was while it disgusted him to have August touch him at all, the touch on his shaven legs through the stockings felt good and something he didn't want to admit to anyone. The conversation was light with the boys asking them what they liked to do for fun, and Candi was more than happy to answer for the both of them. "Oh, we like love shopping, and spending time at the pool and like recently Bailey started her own youtube channel after hearing how successful mine was."

"What kind of videos do the two of you make?" Ryan spoke up and Bailey noticed for the first time the boy had moved his chair much closer to Candi's. "Oh, like let me show you!" Candi said pulling out her phone and pulled up a video. Bailey was happy to have August distracted by one of the videos Candi had on her channel, the girl had a lot of videos, but when he saw what she pulled up he was mentally kicking himself for ever allowing it to happen. The video she pulled up the video he made yesterday about the diet that he shot in the red and white striped bikini. When the video was over August leaned over and kissed Bailey on the cheek. "You look fantastic, I like that you care about yourself like that and know when to treat yourself like tonight."

While everyone was eating their food, Bailey was thrilled to be able to get his hand back from the boy and felt like some of this nightmare was easing as he tasted the creamy pillows filled with lobster chunks. It was like a small bite of paradise and the look on his face said as much. "That good huh? Mind if I have a bite?" August said leaning over. Bailey wanted it all for himself, but he was paying so it seemed wrong to refuse. "Like sure!" but August didn't make a move to reach for the food with his own fork or reach for Bailey's he just smiled goofily to her then opened his mouth. Getting the hint Bailey stabbed one of the raviolis and fed it her date. "That is good, but wait till you try this."

Bailey looked over to August unsure of what he was about to do and opened his mouth to ask when a fork was placed into his mouth with a small piece of lamb covered in a small amount of mashed potatoes. The surprise of food was not a comfortable one, but it was a delicious one. Chewing the sudden mouthful Bailey's eyes opened wide trying to express that it was good. Swallowing the food, Bailey licked his lips and looked down to August's meal, thinking that while his was amazingly good the taste of the meat and gravy was one he wanted more. "I see you liked that, here have another bite!" it was like an odd sort of torture to hate how he was getting the food, but enjoying the morsel, but this time Bailey found himself leaning in to take the bite in his mouth instead of it being forced in. That second bite was all he got and he wasn't sure about his feelings on the matter, on one hand he wanted to just swap plates with the boy, and on the other he really didn't like being fed. Focusing back to his plate Bailey was only able to eat two more bites before he found himself full, the lack of food had shrunk his stomach and the corset forced it to stay that way. Looking down at the plate of food Bailey saw he had eaten maybe one fourth of his meal.

Looking over at Candi he saw she had only eaten half of her salad and when he made eye contact, she tilted her head to the side and raised an eye brow. He wasn't sure what she was trying to indicate so he went with the tried-and-true method of just agreeing with the girl so she would leave him alone. "Bailey and I have to go powder our noses; we will be right back." she said sanding. "Come on Bailey." She said noticing her friend wasn't getting up. Following along Bailey could hear the two of their heeled feet on the tile and was positive the two they left at the table were following their backsides with their eyes. Inside the bathroom Candi walked up to the mirror, washing her hands and drying them off Bailey followed suit, but stopped and watched her as she pulled out her lipstick and applied it to her naturally pouty lips. Glancing over at her friend Candi giggled. "I know you can do that on you own girl, you are not that big of a ditz, but come here let me help. I'm sure you are living in dream land thinking about your man, the two of you looked cozy sharing your food." she said stepping toward Bailey and touching up the red lipstick that had worn off a bit from drinking from a straw and eating.

"Now when you go out there, take your napkin and tell your man he has something on his chin and lighly wipe his chin. I have not a man that doesn't enjoy the chance to look down a girls' top when she leans over. It will drive him wild."

"You... do that?" Bailey asked thinking about looking down Candi's dress to look at her breasts. "Like of course I do, I already did it to Ryan. The poor boy almost hurt himself trying not to look." she giggled again at the idea of driving her own date wild.

Getting back to the table August and Ryan stood up to help seat their dates once again and it looked like they had finished up while they were gone. Bailey smiled sweetly not wanting to do what Candi instructed him to do, until he felt her lightly kick him with her heeled foot. Looking back to the blonde girl Candi nodded and leaned over whispering. "Trust me, he will love it."

Following through Bailey looked at August. "Looks like someone is a messy eater, her let me help." grabbing the black napkin Bailey leaned forward to display his breasts enhanced by the corset and dabbed at the side of his mouth. Before he pulled back August leaned over taking the chance to lightly press his lips to bailey's. "Thanks babe." Bailey made a face at August and pulled back his hand to hit him his anger boiling over. Realizing what he was about to do, but unable to fully stop himself, he instead slapped August's shoulder. "I just fixed my lips." Bailey said hoping he covered up his gaff and pulled out his compact to see if he had to touch them up again. August only smiled at his date thinking about kissing those lips again.

When they left the Bistro, Bailey had to hold August's arm to help him in the five in heels, being unsteady to walk on cobblestone after the sun had set. August opened the passenger door for Bailey and he ran around to the other side, while Candi and Ryan still stood outside the vehicle. Ryan had walked his date over to hear door, but instead of opening it he leaned forward taking her chin in his hand and kissing the girl deeply. With the second kiss he pushed her forward so her back was to the door as she returned the kiss and wrapped her arms around his neck. Bailey looked at Candi's back being press into the door. "Looks like they are having fun." he joked, but when he turned around to look at August, he found the boy leaning in and pulling Bailey in for the same sort of treatment. Mind reeling, Bailey tried to pull himself away, moving closer to the door, but with August holding him tight it just made it seem like Bailey was pulling him backwards so that the two ended up horizontal in the back seat, with the heavier boy on top. Bailey wasn't tried to push, but he didn't budge, he wanted to call out but soon as his mouth was open August's tongue was in his mouth the words then sounding like a moan of pleasure instead of a call for it to end. Reaching around him Bailey tried to use the talons he was forced to get on the boy's back hoping it was get him a reprieve, but it just caused him to press harder into him. Trying to shift his weight Bailey pushed with is entire body maybe trying to work his legs to but a knee between them. To August it just seemed like Bailey was really getting into it, pressing her body up into his and shifting her legs around so that he could get between them.

The slamming of a car door stopped August as he looked over to see his friend getting back into the car, so he looked down at his pretty blonde date who was gasping for air, her bosoms heaving in short aroused breaths. Bailey gasped for air, the corset stopping him from getting much in and was thrilled when it ended, he was sure he could feel the boys erect member pressing into him through their clothes.

When the car started moving Bailey once again touched up his makeup and could see the smile on Candi's face when she pulled down the visor to use the mirror there. The first of three legs of the date were finished now and already he felt like he was a piece of meat. August was honestly treating him better than he treated a lot of woman, he was just a horny boy. One that had been encouraged through text messages the other day. August reached over and held Bailey's hand for the rest of the trip to the theater that was just a few plaza's down from where they eat.

"I picked up the tickets earlier today, the movie has been out for a month but the romantic comedy is said to be a big hit. All we have to do is pick up some refreshments and we should be all set." Ryan said to the rest of the group as they went inside.

A shiver went through Bailey stepping into the air-conditioned building, feeling it over his bare shoulders and across his stocking covered legs. The shiver caused him to stop momentarily and move quickly to catch up, with each sway of his hips he could feel the breast bouncing. Soon they were heading into the theater, with a medium coke and small popcorn. Ryan led the group up to the back row in the dark theater with the girls sitting next to one another in the middle and the boys on the ends.

The movie had just gotten past the opening scene Bailey reaching over to get some popcorn from the bag August was holding determined to watch the movie that he did not want to see, rather than give the boy a chance to violate him again. To the side though he could already see Ryan having one arm around Candi, pulling her close with the arm up between them, the other rubbing on her thigh and their lips pressed together, like well exactly what they were a pair of horny young people out on a date. Bailey refused to look from the screen though, so long as he kept August in his peripheral vision, he was pretty sure he could weather this storm.

Feeling August try to put his arm around his shoulder Bailey scooted in the seat to be closer to Candi, but in doing so it caused him to sit in a way that his legs were now moved closer to his date, and causing his dark dress to move up exposing the top of one his thighs and leaving the sight of the lace stocking tops. Not one to turn down an invitation, August moved his hand over Bailey's sexy nylon covered legs, massaging it and moving up to the top of the sexy stockings, the way she was sitting looked like she was inviting him.

Bailey's eyes bugged out of his head, feeling what was going on, he thought he was safe with the move and was trying to watch the movie. The feeling like before felt good but it brought a panic and disgust. Moving as fast as he could in the cushioned chair, he shifted back to the way he was, rather having arm around him then the groping. Moving the way he did after being felt up made August think she was just ready for something more. Wrapping his arm around her he started to kiss Bailey, the arm rest still between them. Using the arm rest as a brace Bailey pulled back and said the first thing that came to his mind. "Thirsty.." a look of disappointment came to August's face that Bailey as more than happy to see to deny him what he wanted.

He was a man and did not want to be kissed by another man while trussed up like some love sick girl. Keeping the drink in his hands Bailey sucked down the carbonated liquid and took a few handfuls at a time of popcorn trying his best to get back to the movie. Soon the drink was empty so he put It in the cup holder closer to him and Candi.

Reaching for another handful of popcorn Bailey reached over further not feeling the bag and then he felt something smoother and... turning his head to the side, Bailey saw the bag of popcorn was moved to August's other hand to be closer to Bailey. The move from his lap to where it was now caused Bailey to reach over the popcorn and rub and grasp August's now inflating member.

Bailey had never felt another man's cock before even if it was through a pair of dress pants. He slowly looked up to meet his date's eyes as if everything was moving in slow motion, he wanted to yank his hand back, but he found another hand placed on top of his own pressing it in and rubbing it as the cock came to life. He shook his head no, but August's eyes were already closed as he flipped up the arm rest between them and pulled Bailey into him. Already leaning over to try and get the popcorn combined with being pulled almost to August's lap caused Bailey to be pulled up to his knees and pressed into August. The boy had one hand behind Bailey's head pulling their faces together, the other helping his date work him through his pants. When August thought she had it he let go of her hand, instead moving it to the small of her back. Bailey struggled in his arms, but August just felt his date wiggling to rub her body onto his.

The hand on Bailey's back moved down to his ass rubbing it and moved down to her leg and back up under the skirt feeling the stocking tops and garters, his hand sliding up to rub her thong-covered ass. He could hear how excited she was moaning in enjoyment as he probed her mouth with his tongue. She had stopped rubbing him, but figured it was because she was ready for him to free himself now that he was fully erect. With one last squeeze of her ass he unzipped himself pulling his stiff member free of his pants.

August could feel how excited she was as she slapped her hands into his chest and tried to push his hand off hers as she moved it to his groin. She was trying to turn him on more before he got off, but he was ready, she had already done what she intended to do. He had waited for this since she was texting him before asking to see his dick. Bailey was freaking the fuck out, this man who was four years younger than him had placed his long-nailed hand around his warm thick cock.

He felt his hand pump up and down twice being guided the gold bangled bracelet bouncing on his wrist. Here he was trapped with the only way out was to jerk off another man here in the dark theater, already on his stocking covered knees leaning into him. When August finally let go of the back of his head he was able to get his first full breath, or ast much as he could in the corset. The firm grip didn't go away, just moved from his head to his back keeping him pressed forwards as August's mouth moved down to his neck and down to his exposed collar bone. Even in the dark room, with the light from the movie he could no longer watch he could see the exceedingly impressive member, one that was much larger than his own. The sight of his French tipped nailed fingers moving up and down made him sick, but he knew he really only had two options at this point.

Full on throat punch the guy and ruin everything and risk exposure or getting him off. When August got Bailey into a good steady pace he let go of her hand and moved his own to rub on his date's exposed legs. With each motion of his hand Bailey felt worse and worse, and needed it to end and the only way to do it and not risk the entire charade was to get him off. Moving his hand to the base of the dick and starting to move his hand in a corkscrew type motion before moving his hand up to palm the head running his fingers off the tip, he could feel the cock growing about to give its load.

Redoubling his efforts to make this end, Bailey still leaning forward used both his hands twisting them in different directions. "I'm about to cum.. God Bailey I'm going to cum." August whispered in his ear leaning back into his seat and letting go of his date so she could finish. Unfortunately, without August's chest to lean into Bailey fell forward on his knees his face falling into his lap, his face now less than an inch from the erect member, trying to sit back up to get away August took it as Bailey being over eager and pressed her back down to his erect member already slick with precum.

Bailey went to scream no but all it did was giving an open passage for the huge member to enter his warm mouth. August was already to blow and not much else was needed to finish the task so almost right away after feeling the warm wetness around his cock August erupted into his dates mouth pressing her down out of reflex trying to hold onto the fantastic feeling.

When the pressure holding him down was gone, Bailey pulled himself up from the lap angrier than he had ever been in his life and had absolutely no outlet for it. Getting himself situated in the chair he looked to the coke and tried to drink some down to get rid of the salty stickiness in his mouth that felt like it coated the entire thing. As he sucked air in through the straw, nothing came to him, Bailey had already drained the cup of everything in his earlier attempt to keep August at bay. So he sat their sulking paying little mind to the end of the movie or how Candi was full on sitting on Ryan's lap forgoing her seat entirely.

Bailey kept rubbing his tongue around his mouth trying to build up some salvia to wash the taste away and by the time the movie was over he had lessened the flavor though it still lingered. Soon as he could Bailey ran past everyone down the stairs the best he could in the five-inch platform heels. He would have loved to get up earlier and run to the bathroom, but being stuck in the middle he would have had to push past both Candy and Ryan. Shoving the bathroom door to the ladies' room open as hard as he could he rushed inside and wanted to just hold his mouth open at the faucet, but the second he heard water running he knew what his priority needed to be. Bailey had drunk a lot of water at dinner and a full medium coke on his own while compressed down in a corset.

Getting into a stall Bailey pulled the skirt up and his panties down, then peeling back the tuck kit so could relieve himself sitting down on the toilet.

The empty bladder felt better than would have expected. Settings everything back to where it should be he stepped out of the stall with a smile on face from the relief of emptying an overly full bladder. Candy was sitting on the sinks counter swinging her legs smiling back at Bailey. "Someone sure had fun, I saw you bending over into August's lap and you have a little something." she said tapping the side of her own mouth. Stepping over to the mirror Bailey saw a little bit of dried cum and proceeded to wash it and the rest of his messed-up lipstick off. "I did not have fun.. That was horrible."

Candi only laughed as she watched her friend wash her mouth out and pull out her lipstick to fix everything again. "You can't lie to me girl, I like totally saw you savoring the taste as you rolled the flavor around in your mouth after."

"I was not savoring it!" he said, exacerbated.

"Sure, sure you don't have to hide anything from me. I'm actually like a little jealous of you." Bailey stopped what he was doing, holding his lipstick in his hand that he was just about to apply.

"Of me.. Why?" he said with true feeling not considering she wouldn't know his true feelings of everything that had gone on. Recently spanked by his girlfriend, laptop taken away, sent to bed early, given a list of chores, kissed by a cop that was really there to arrest him, groped, kissed by another man and gave a hand job to before it being finished off in his own mouth.

"Well, like I want to do stuff like that, but like." she shrugged a little before continuing. "I never had the nerve, it like I guess is easier for you with seeing your Mom date, but Daddy hasn't even kissed someone as far as I know since my mom passed." when the subject of the dead mother came up Bailey knew he needed to tread lightly and decided to vacate the subject all together.

"Tonight is kind of cheat day for the diet... What do you think is for dessert?" the comment made Candi laugh, she hopped down to her heeled feet and smirked at her friend. "Why need something sweet to compliment that salty flavor?" face turning red Bailey put his lipstick back into his little purse. "I do not need something sweet to compliment cum!" he said it to be firm to show he did not want that in his mouth at all but it again only made Candi laugh.

"Oh, I was talking about the popcorn, but now I know my little sis likes the taste of cum on it's own." she said, wagging her eyebrows at Bailey before running out the door. "Come back here you!" Bailey shouted trying to follow, but ended up bumping into August shortly after getting outside the door.

Putting his arm around his date August looked to the other two. "Ready for dessert?"

"Like actually, I was just talking with Bailey and while today is out cheat day for our diet. She doesn't really want anything else right now being happy with the salty popcorn she had. Do you two like think we can just walk around for a while instead?"

The rest of the night passed without nearly as much mental trauma for Bailey only having to endure a light make out session by the car when they got to the apartment. August taking a lesson from Ryan and pressed him to the car this time to make out. The feeling of being pressed into from one side by the boy and his back to a metal ungiving object made Bailey feel a little helpless and he wondered if this is what woman felt like. The night was horrible for him, he wasn't like Amanda enjoying the taste of his cum or liking being pressed into something as he had his way with her, he was a man. Yet as the last kiss goodnight was given as the door with the girls already fixing their lipstick again that night, he couldn't have felt more like a girl being held and given a tender, but short kiss.

The pizza was down to the last slice, Derrick sat at one end of the couch, while Amanda was on the other with her legs up next to her. As the movie played Amanda brought her hand to one of her feet, rubbing on it to work out some of the soreness from walking around in her heels all day. Seeing what she was doing Derrick shook his head slightly. "I can say for sure every man enjoys seeing a woman walk around in heels, but no one should have to suffer for others like that." Amanda looked to Derrick and then back at her heels she wore to work that day. "I have known my fair share of girls that could wear heels all day and not be bothered, and I will have you know I wear them for me. I like the shoes, just not the after affects." glancing to the movie then back to Amanda, Derrick nodded and scooted a little closer on the couch, taking one of her feet in his hands. "Then I suppose it is okay to suffer for your own enjoyment, but friends and people you trust can help ease your burdens. At work you can delegate and right now I can do this." he said starting to massage her foot.

"Mmmm, you do not need to do that and can stop, but maybe... just a few more minutes or maybe just do that forever." she said enjoying every second of the foot massage. She got something close to this when getting a pedicure, but Bailey was never one for giving others any type of massage. So while the movie played Amanda closed her eyes listening while her feet rested in Derrick's lap as he gave her sore feet some much desired attention. When the massage was over Amanda stayed in place, now laying on the couch, her head on a pillow and her feet up in Derrick's lap, content to enjoy a movie she loved and feeling more relaxed than she had in a while. The two collected themselves and stood when they heard the key in the door announcing their daughters had returned from the evenings date a little earlier than expected.

When the door opened Bailey put away the little pink key and walked inside the apartment, both his and Candi's heels echoing in the hallway between the apartments. Behind them Ryan and August held up their hands waving to the parents to indicate their departure and headed home. "We were expecting you to be out a bit later, everything okay girls?" Derrick said with concern in his voice.

"Everything is like amazing daddy; we had such a great time. Bailey like wanted to stick to her diet and not have dessert tonight." Bailey was just happy she didn't mention anything more and quickly agreed with her before she went into any more detail. "I like cheated so much at dinner that I like just couldn't eat another bite and not like hate myself." looking over at her dad Candi gave Bailey a big hug. "I had like sooo much fun tonight and I'm super excited about tomorrow!" Candi said giving Bailey another smaller hug giving Amanda the same treatment.

"In like one of my child care classes it said parents are always worried they are not doing a good job raising their kids. I like just wanted you to know Bailey is like someone I am proud to have in my life and like you did that." the statement caused Amanda to get a little feeling of warmth and happiness, she always wondered if she would be a good mom, and these last few days were able to give her a little taste of that. While Candi was speaking with Amanda Derrick came up to Bailey and gave her a gentle hug that lasted a few seconds, every one of them was too long for Bailey. "I complimented Candace earlier, and I just wanted you to know that you are a beautiful young woman. Knowing how happy you make Amanda and Candi tells me how special a person you are Bailey, and I am happy we got to meet." in response Bailey blushed and meekly said. "Like meeting the two of you have changed my life." it was a vague enough statement that Bailey was sure he would take it positively while he meant it in a negative sense. The statement did cause Derrick to hug Bailey again causing him to almost lose his balance on the tall heels. "I promise you we both feel the same way."

Slipping her heels back on Amanda looked over at Bailey. "We will talk in a few princess, I am just walking them out." she said before walking out of the front door with the Connors family. Walking outside Derrick smiled at his daughter just so proud to see her so happy and wanted to continue to see her like that as long as he could. "Candace, how would you like to drive home?" he said holding up his car keys. The vehicle didn't actually need a key to be put in but the display of them and the jingle of the keys had the affect he wanted. "OMG, YES!" she said moving over and snatching the keys as fast as her heeled feet would move her and then got in got in the rental car behind the wheel.

Adjusting the seat to her much shorter height Candi moved her hand to the rearview mirror, placing her hands on the wheel a huge smile on her face, and in front of her she saw her daddy reach out and take Amanda's hand pulling her close to him. She seemed to be caught off guard has he moved his other hand to cup her chin, raising her head up slightly before he leaned in for a tender kiss.

"Oh my god, oh my god, OH MY GOD! Did Daddy just kiss her!" Candi squealed in delight at the sight, believing this to be the first woman he had kissed since her own mother years and years ago. Her eyes were glued to the scene unfolding in front of her like it was the best romance movie she had ever watched.

When her daddy pulled back smiling at the target of his affection, she could see the blush in her face. She couldn't make out the words, but he saw her shake her head and say something. Her heart sank a little seeing her daddy get rebuffed and him nod and say something in return before walking over to the car his back to Ms. Best. Candi was able to see something that her did not however, when his back was turned, she watched him go, putting one hand to her warm cheek and smiled watching him go. Candi was full of glee thinking she could give her dad a pep talk and if he did it correctly, she might be able to get a new mom and have a sister for real.

Amanda watched Candi drive off under the supervision of her dad, she could still feel the blush in her cheeks. Derrick was such a sweet caring man and spending time with him over these last few days had been nice. He had provided her with feedback on how to be better at her job and how to succeed if she got the upcoming promotion and while he was being successful at his career, he was raising a spitfire of a daughter. She could tell he struggled more with her than his work life, but the way she adored her dad told Amanda everything she needed to know with how he was doing.

Then with all that he was interested in her, he gave compliments and was never pushy. Heck even after she told him that this couldn't happen he handled it with grace. She was already in a relationship, she couldn't say that to him, so she let him know it wouldn't be fair to either of them or the girls to try and have a long-distance relationship. Even in rejection he was charming saying "At least he would have this week of memories of her, fireworks and stars."

"He kissed me... what am I going to do." the blush returning to her cheeks as she relived the memory. Looking back at the apartment building Amanda pulled out her phone to call her sister and tell her everything that happened from the chores she set out for Bailey, too the kiss and see what she had to say. "No Amanda, you can't tell Bailey that he kissed you and no that isn't cheating. Right now the two of you are not dating, right now you have a daughter remember. Besides didn't he once ask you for an open relationship and before you say he was kissing. I remember the phone call where you were crying thinking you weren't enough for him because of how old you were. You told Derrick no.. And I wouldn't have done that, that man is hot with a capital H. You just go back inside and get ready for bed before you deal with Bailey and her not finishing her chores, remember she is your daughter any talk of being a couple should wait till this is all over, the more you see a teen age girl the less likely you will be to mess up." agreeing with her Amanda said her goodbyes and promised to catch up tomorrow night after she spent the day at the water park.

Back inside Bailey was sitting at the vanity writing with a red pen in his diary about the events of the day. The task of writing from the perspective of the boy crazy teenage girl was difficult, but he did suppose it helped him think through how he should act while playing out the role till the Connors left. He just hated writing about a supposedly cute cop kissing him and giving him his phone number.

When he heard the front door close, he placed the business card the officer gave him in the little book so that no one would find it and went to see his girlfriend and have her help him get out of everything he was wearing, no way was he going to be able to get the corset off and wasn't sure he was practiced enough with the nails to get the heels off with the corset adding to the difficulty of the task. Bailey looked to Mandy already halfway down the hall when he called out to her to ask for help. "Mommy I need.." but was cut off before he could finish the request.

"In a few dear, we have to talk about today like I told you we would earlier, but first I am getting out of my work clothes." it was rare for Bailey to see the master bedroom door closed, they didn't need much privacy from each other. Though right now the way he was dressed, with his own girly room to sleep in the closed door felt like a chasm between them.

Head hanging low, Bailey walked back into the room, hips still swaying the click of his heels announcing his location. Sitting back down at the vanity, Bailey crossed his legs at the knee and went back to his task of chronicling his well.. Her day.

Mentally prepared for what she needed to do Amanda walked into Bailey's room, when she came in she saw her blonde green-eyed daughter writing in a little pink book with a red pen. "Come on princess, let's get you out of that dress." Amanda assisted Bailey taking the dark dress off and opened the closet to hang it up and when she shut the door she saw something on the dresser. Picking up the multiple clothing tags she held them up looking at Bailey. "What are these young lady?"

Bailey saw the clothing store tags in her hand and wasn't sure how or why they were on his dresser. "I umm.. , I'm not sure." confusion in his voice, not sure how the tags from the clothes came off. "Maybe Candi did it." slapping her hand back down on the dresser leaving the tags where she found them Amanda gave Bailey a stern glare, upset at what she had done. Not knowing Bailey left Candi alone in the room it made no sense to her how he wouldn't know if she went through the closet to remove the tags. This was so very much like Bailey to not own up to his own mistakes, first the laundry and now this. Removing the tags meant her sister was out of a good deal of money that she was sure she only put forward knowing it would be charged back to her card, all just to help them pull this off. Grabbing Bailey by the wrist she walked over to the bed and yanked Bailey off the pretty black heels and across her lap. Bailey had the dark dress removed, but was still in the black corset, black thong panties, garters, stockings and heels.

"No daughter of mine is going to be so disrespectful that she blames an innocent girl." Amanda said as her hand came down with a smack to Bailey's mostly bare ass. "NO, STOP, NO I DIDN'T..." the cries cut off by two more smacks. "Bailey Ann Best you will tell me you are sorry" smack "for removing the tags!" smack "You will apologize for not finishing your chores." smack "You will apologize for trying to blame others." smack "Do I make myself clear young lady?" her hand came back down for two more swats to the now red exposed rear. Holding in sobs "I'm sorry, I'm sorry, I did it I'm sorry!" Bailey cried out saying what he believed what Mandy wanted to hear just so she would stop hitting him. Amanda slapped Bailey's ass one last time before helping her to her heeled feet. "Removing the tags means we have to keep the clothes, your intention or not Bailey Ann, your closet will now be full of pretty clothes.

We are going to have to figure out how to pay your aunt back, these were not cheap. Now remove your makeup, jewelry and heels and then get in bed. "But.. But the corset." shaking her head Amanda pointed at Bailey's heaving bosom as he still tried to catch his breath from the spanking.

"Maybe being a little uncomfortable tonight will remind you to not be so careless. You know what, get cleaned up and we are calling your aunt so you can tell her what you did." Bailey went to object again, but as he opened his mouth the glare he received from Mandy made the words die in his throat. So he just nodded and looked to the floor. "Could... Could you help me with my shoe's mommy?"

Amanda unbuckled Bailey's heels and helped her remove makeup and jewelry and then handed Bailey her own phone with a stern look. Taking the phone Bailey pulled up contacts moving to Aunt Megan and hit dial while on speaker phone. When the line picked up Bailey took a breath and went right to it while Mandy looked on. "Aunt Megan, I umm took off the tags for the clothes you got me and I umm mommy said we will figure a way to pay you back."

"Bailey my dear, it sounds like I am on speaker phone, So I'm sure my sister is listening. You don't have to worry about it, I'm sure between the three of us we can figure out everything. Now, I understand you had a date tonight and I would love to hear all about it. A few time Becky would talk to me for hours about her adventures and it would just make me so happy to hear you tell me about yours." hearing what she wanted to hear Amanda nodded and kissed Bailey on the forehead. "After you are done talking to you it is past bedtime." with her gone Bailey turned off speaker phone and prepared to tell the bitch about the day and opened the diary to just read from it.

"As much as I would love to hear about your night looking so pretty, cause yes I saw the photos from earlier. I have a few things you are going to do before bed. Number one you are going to text that sweet girl Candi and say thank you for tonight and how much you are loving having a big sisters.. You know what I loved your video before, so how about we stay with what you said before. Tell her how much you are loving having an older sister. Then you are going to text your date and tell him how you can't stop thinking about him. With so little trust between us you of course will have to send me a screen shot of the conversations. I would say you had to make a nice video for your channel, but it seems it is past your bedtime. Lastly you are going to go to my sister and talk to her and just leave the phone on so I can hear, what conversation you have is up to you from these two options. One option is you tell her about you stealing from her to pay for whores and for good measure how many times you have done it."

"No, you said you wouldn't tell her!" Bailey said in shock thinking they had a deal. "I'm not telling her anything, it will be you.. Of course, option two is tell my sister she needs to think of her last boyfriend as her ex-boyfriend for real. Looking the way, you do, you can't please her and what was it you said once in defense of yourself. It is just to release tension and a man has needs, well my dear niece so does a woman. Let her know she is free to do that without needing to feel guilty." Not being able to help it a few tears ran down Bailey's cheeks. Megan could hear the sniffling and the half mumbled. "Okay."

"I'm looking forward to seeing the conversations and listening to what you have to say to my sister to convince her, cause you will be convincing Bailey or I will have a conversation with her."

The first task was talking to Candi, this would be the first time Bailey reached out to Candi first.

Bailey: OMG tonight was like totally amazing!

Candi: Bailey! OMG yes it was! I can't believe you ordered lobster for dinner

Bailey: It was just ravioli... but it was so good.

Candi: It looked like you enjoyed what August had more than yours though or did you like it better cause he was feeding you?

Bailey: Moving on! I just wanted to like say I'm happy you came to town. Things have been like feeling really nice having a big sister to rely on.

Candi: OMG you are going to make me cry!

Candi: It has been like so good having you as a sister, if it is up to me it would never end.

Bailey: Wish it like was up to you

Candi: Have you ever seen the old movie parent trap?

Bailey: No why?

Candi: NM I got it ;-)

Bailey: I'm like sure you do

Bailey rolled his eyes at the thought of anything the teenage girl having any real impact to keep this going. Come the end of the week he would be free of all of this and he planned to shave his hair off and grow out a beard even if it would end up being a patchy. Saturday morning, he would wake Mandy up and make her orgasm two or three times before he ever even put is cock inside of her. He was looking forward to that Vegas trip coming up too and after he did that and sold his wild oats as it were maybe he would buckle down and see about getting a job again. Though after all this Mandy should be making more money with that promotion, so maybe not. The thoughts for the end of the week were pleasant, especially after today and not wanting to let his mind go over any of that trauma, he took a screen shot, sending it off to Megan and prepared for his next task.

Bailey: Can't stop thinking about you

August: Some guys say to hold off on talking to a date for a few days.

August: I don't think I can go a day without talking to you. Tonight, was just wow.

Hoping the boy would just shut up and not say anymore he just was repeating one word over and over. "Please, please, please.."

August: You taking it in your mouth at the end, wow Bailey, I have never been with a girl like you.

Bailey: Yep, the lamb you had was super good, was happy to have it in my mouth.

August: Yeah that too ;-)

"Fuck.. Maybe she won't realize what he is talking about, if there is a god she won't." he said sending a screen shot and then calling Megan.

"Bailey my dear, my lovely niece, what wonderful conversations you are having! Now just one more task my dear." grumbling Bailey turned off the screen to the phone and walked to the master bedroom still walking like a runway model in his stockinged feet. Knocking on the closed door he opened it slowly to find Mandy sitting in the center of the king size bed, the pillows being arranged to make it look like she slept alone. She looked up from a book she was holding and taking off her reading glasses.

"You and your aunt have a good conversation?" knowing Megan was on the phone right now and the thought of what she is making him do his eyes went downcast. "Umm I was like thinking about what happened the last time we umm tried to be intimate and like I know what I look like and how like it can't be easy on you to like suddenly be single with no one to umm... help comfort you. I just wanted you to know it would be okay if you saw someone else or you know held hands with Derrick or whatever."

Amanda watched Bailey standing in the doorway being awkward while looking like a teen girl ready to go turn on her man in the bedroom minus the makeup. While talking about her seeing someone else and how she honestly couldn't even imagine being with him looking the way he.. Well, she was. The talk of seeing someone else reminded Amanda of the conversation her sister brought up when he talked about having an open relationship so he could also date other people. At the time it sounded purely selfish, but him bringing it up now dressed the way he was she thought maybe she jumped to conclusions before. Maybe it wasn't him that wanted to be with other girls, but him wanting her to be able to see people to fill her desires that he didn't or wouldn't. "Bailey my dear, I hear you and understand what you really mean. I love you dear, but it is past your bedtime. You go scamper off to bed, unless you want to talk about boys?" the last part was just teasing trying to lighten the mood.

When Bailey went back to the girly room and climbed into bed. His feet were hurting from the heels, rear was hurting from the spanking, his entire midsection uncomfortable from the corset's compressions and the feeling of still being tucked. Bailey went to untuck and has his hand went into the thong panties he remembered his hand around August's dick and then the experience of kissing him and the blast of cum that went through his mouth and stomach.

Grabbing onto the bear, Bailey pulled it to his bosomed chest and cried into the bear for a few minutes, seeing images stuck in his own head reliving it as he squeezed the bear. Not wanting to be alone, Bailey climbed out of the bed and went back to the master bedroom, hoping this wouldn't cause Mandy to be upset or turn him away. Opening the door the lights were out and he could see her sitting up as he came in. "You okay sweetie?" Bailey nodded, but spoke thinking she couldn't see him. "Umm I can't sleep, I was thinking about tonight and you and was hoping I could stay in here, just tonight." he added at the end hoping it would help convince her.

"Yeah baby, you and teddy can stay in here tonight." Bailey looked down at the bear still in his hand, not realizing he was still clutching it. He ran and jumped onto the bed, and the second Mandy put her arms around him he started to cry once again.

"Shhh, it is okay baby, today has been a long day. Shhhh.. Everything will be okay." she said running her fingers through the long blonde hair. With the expulsion of emotion, the embrace and nailed fingers through his hair, Bailey was soon fast asleep still squeezing the teddy bear.