Pool Time

Dear diary,

My totally awesome aunt Megan got you for me so I could like always remember the fun I've been having lately.

Where to start tho?

Okay so like I'll start with today.

So like, this morning mommy woke me up like super early for me. (I am so not a morning person!!!) Anyway she woke me up and Aunt Megan came over and she's so sweet she brought me these like great smelling shampoos and conditioners and soap. My morning shower totally always perks me right up.

After Aunt Megan and I had a nice heart to heart about like porn and stuff. She said she wouldn't like tell Mommy and gave me some videos so I wouldn't get in trouble with Mommy. The man in the video was like totally hawt too!

Auntie Megan left and let me get dressed in the cutest outfit.

An off the shoulder knit shirt and like a sexy red bra and matching thong a black jean button up skirt and like totally the cutest white heeled wedges with an adorable white ribbon! Best part the bra made my breasts look even bigger. Tho I'm still not as big as Mommy.

Aunt Megan is so nice! She even helped Mommy clean out her ex's old junkie clothes from when he lived here and then she like helped me put on my makeup and made me super cute! She totally called me on liking older guys tho lol.

Oh like totally awesome news too diary! Mommy's letting me go on a date again. After last time I was like so afraid she would never let me date again after she totally caught me going down on the last guy! But thanks to like my totally awesome bestie! We even got a double date together ^^ I'm like so excited!!!

After Aunt Megan finished helping me with my make up and plucking my eyebrows so I can match Candi we left to pick up Candi! But like not before I grabbed Mommys white Tory Burch purse that totally went with my ultra cute heels!

When we finally picked her up ill admit I was nervous. Shes like so pretty and amazing I don't want to like look totally ridikulus around her! She was wearing this adorableblack off the shoulder top with three quarter sleeves, a white skirt with polka dots on them, The cutest black three-inch chunky heeled booties with a matching black clutch purse. So of course I was totally nervous she knows so much about fashion I dont cause my stupid tomboy phase. But like shes totally amazing like I said and she broke the ice thank god.

She told aunt Megan what a great person her and Mommy are. She's like totally right too. I love them both so much! And as great as auntie Megan is Mommy is even more amazing!

Where was I oh yeah. Candi went like totally gaga over my makeup. I wish I was good at makeup like auntie Megan. Candi offered to teach me makeup tho so maybe soon. And see i told you she was like amazing!!!

When we got to the mall we just HAD to have a photoshoot we looked so totally fabulous and drop dead gorgeous! Even auntie Megan got in on it with us. Of course cause she's like so gorgeous and pretty herself we just HAD to. Aunt Megan said Candi could like call her aunt Megan too cause we like totally look like sisters!

So like when we actually went in the mall auntie Megan told us she like had a surprise for us. And she did! She had booked us a manipedi session together at phenomenail!

We got these totally cute french tips and it felt so nice to be pampered like that. And in the end I had these totally amazing acrylics! Too bad Mommy wasnt with us she totally deserves to be treated so nice. Next time fer sure!

Then Candi had the best idea ever. She like always does. We play a game where we each buy five things that like say something about who we are or a happy memory.

When we were done we like went outside and and Aunt Megan went first and had some red yarn cause grandma like taught her how to knit. Then she had a puzzle of a pie. Ugh puzzles. But like Aunt Megan said she was going to teach me to bake! I would like totally love that! I can't wait to bake with auntie. Oh did you know auntie Megan went to Florida for her honeymoon? Shes so lucky I love swimming and the beach like so much! Auntie Megan and I also both like totally love sweets! And so does Candi (no surprise!) like what girl doesnt like sweets?! Thats like the only bas thing about this diet im on! I miss cookies!! I wonder if they make like diet cookies?! If not they totally should!

Candi and I both got sunglasses cause we like both like being outdoors. I just wish I didnt burn so easy! Candi also got candy cause she likes candy (duh). That like totally makes sense too. And a worlds best dad mug cause like she has the best dad. Well I think my daddy was the bestest but her dad is like totally awesome too just like his daughter. And she loves horses too! We like have so much in common its not even funny. Like maybe we are actually sisters seperated at birth! Idk how that would happen cause Mommy would definitely remember but I still think its true! Or like maybe I just want it to be. And obvi she like had makeup cause duh. Makeup!

So like I got a lot of the same stuff as Candi but I got a worlds best mom mug because like Mommy IS the best in the world. And I got these princess playing cards cause like Mommy and I play cards like all the time and...I like always wanted to be a princess.

Candi hugged me. She is like so sweet! And it turned out thats what her Daddy did on his first date with her mom. That does like totally sound like a cute date idea.

Okay so like after that we went to this store that had all kinds of swimsuits and best of all BIKINIS! Like I was just telling auntie Megan I wanted to work on my tan I got totally pale over Christmas break. Ugh! But like Candi invited me to tan with her at her hotel so of course im like totally going!

When I get my own place Im totally gonna live on the beach so I can rock a bikini like every day. :)

So any way I like totally found the cutest bikini ever! The bottoms was blue and had these totally cute little flowers on them! It like covered all of my butt tho and come on thats like my best asset (hehehe) but hey I was still like totally hawt!! I think Candis right like the boys are totally gonna eat me up! I mean who could resist?

After Candi changed idk wich one of us had the cuter bikini tho. Eh ill call it a tie cause hers was totally cute to.

And OMG we went to Victoria Secret after! It is like the bestest place on earth! Forget Disneyland! I got so many cute thongs cheekinis some boyshorts and this special one with a heart shaped hole near my booty and a totally cute bow. I bet whoever gets to see me in that will like totally flip there lid!

Lets see what else we like got so many bras thatll make my boobs look even better!

We then got like some yoga pants and shorts. I think Candis right. It wont take me long to get my booty even sexier.

Okay so then like after we played another game. Candi and I picked out a dress for each other. I found a totally fab Alfred sung! Candi loved it! And best of all? It totally has pockets!

Candi picked out this like totally sexy velvet green maxi. Velvet just feels so amazing. The girl has amazing taste. And so smart too! She had this totally great idea! Cause August and Ryan thought we were sisters we should totally dress alike for our double date! Hehehe

So we got this totally cute off the shoulder a-line dress and Auntie said we could totally be twins. See im not the only one who thinks so!

Of course what trip to the mall is complete without getting some totally sexy and cute heels?!

Im like so thankful to Aunt Megan for today cause I finally got all the pretty clothes ive been dreaming of since I was like ten!

Oh and like more proof Aunt Megan is like the best auntie ever? She has another surprise for me! I finally got my ears pierced and even my tummy :D

But like dont tell Mommy cause she was like totally against me getting a belly button ring. But like Aunt Megan said she totally has my back cause Mommy got an ankle tattoo when she was my age so like its only fair I get it!

Oh after the mall the fun didnt end! Candi totally had me on her channel. I was a little nervous at first. And like even tho im older by like a month Candi is totally the big sister cause shes taller and lets face it smarter than me. I mean look at all the great ideas she had today? I wouldnt have thought of them in like a million years! Im like so lucky to have a big sister like her lol

And like her Daddy has to like aprove all her videos and he totally saw it and said we looked great! Like obvi! Then Candi invited us to lunch! Aunt Megan helped me keep on track with my diet. Sigh. What a girl has to go through to be drop dead gorgeous. But Candi is so amazing she like is going to join me so maybe this will be easier with a diet buddy.

Too bad shes leaving in like five days. I'm so going to miss her :(

Okay so then like Auntie Megan got a text from Mommy and aparrently we like won tickets to a totally awesome water park when we won the three legged race!

After we left Candi :( Aunt Megan and I talked about my first date coming up soon. I told her I was like totally nervous but she said everyone is, even Becky was nervous. I just hope Mommy will help me get ready. Shes always so pretty. But Auntie Megan offered to help me practice until then cause I like totally need to learn. I love her like so much!

Ps

Okay so like I almost forgot! Im such a ditz! When we got home Mommys work friends came and put a room together for me in like a less than a day! All for my birthday! Im not the only one who thinks Mommy is amazing! I mean who wouldnt?

So like my bed has the cutest pink bedspread. And its so big! You could fit like three people on it! And it has the fluffyist pillows omg! Perfect for sleepovers. Totally my favorite color! K but then like the walls! So many flowers! There just so pretty!! And like we put my clothes up and every thing and Auntie had one more surprise for me! You. She like gave me this diary and im like so greatful I really want to find a way to lay her back for every thing shes done for me.

After all the sexy outfits I just like couldnt resist texting August. Course that got steamy. I showed him my boobies and well His dick is soooo big! I wish he was here now! I so cant wait for our date.

Any way Mommys home and I cant wait to show her everything we got today! Ttyl

--

Bailey sat at his new vanity just having finished writing out today's events in his new diary. He had tried to make it sound as much like a little teen girl as possible. He dreaded the idea of anyone reading it and was already ashamed of the idea of even Megan reading its contents. He tried to make the writing as over the top ditzy and girly as possible. Even going so far as to dot his i's with hearts and misspell a few words. As he closed the diary, he took another look around his prison for the week. April had done one heck of a job. The room screamed girl and he absolutely hated it.

After taking care of her work emails Megan remembered the package, she had ordered should be in the mailbox by now, she thought. Grabbing her purse and went to check. Reaching the wall of apartment mail boxes, she reached into her purse and pulled out Bailey's missing keys. Then using them she unlocked the mailbox and removed a small package leaving Amanda's mail inside. No one needed to know she had the keys. Taking the package in hand she headed back inside.

Just then Bailey heard the front door open. Thinking it was Mandy he rushed out of the room only to find Megan walking in from outside carrying a package.

"Here you go girlie these are the kits I told you I ordered to help you tuck. Why don't you be a good girl and go try one on. I ordered their largest pack so you should have more than enough to keep that little growth of yours in check this week." Megan said with a grin as she tossed Bailey the box.

Reluctantly Bailey did as he was told heading to the bathroom to While he hated having to tuck himself the kit was a much better solution and though still uncomfortable it didn't feel as bad as his former taping method. He was shocked however with just how good a job it did at hiding him away. Once his panties were back in place, he couldn't find any signs of his dick. In a moment of horrible realization as stared into the bathroom mirror, he saw nothing but a sexy blonde teen in little red thong. Shuddering he quickly finished redressing before rejoining Megan in the living room just in time to see Amanda walk in the door carrying a pizza.

Amanda was shocked at the sight of Bailey standing before her. She had been expecting to see her boyfriend dressed as a girl. She was not prepared for just how hard it was to see anything of her boyfriend in the blonde teen before her. She was the image of a sweet teen girl and for a minute Amanda let herself believe that she really was her little girl, the daughter she always wanted. She made a decision in that moment. She couldn't have a real daughter due to her choices in life but for just then one week she would let herself pretend. If Bailey was this committed to the character, then she would fully commit as well and try to be the best mother she could be.

On seeing her Bailey decided to seize on this moment before Megan could get control again. Mandy would surely protect him from any more of Megan's abuse at least he hoped so. Running over to her as fast as his heeled feet would carry him, he hugged her tight.

"Mommy I'm so glad your home. I missed you today. Auntie Megan was so nice to take me and Candi shopping and stuff, but I like wish you could have been there. Oh, and thank you so much for my like totally awesome birthday present. Miss April and her friends did like a super fab job on my room. It's like mega cute. Come on let me show you." Bailey said with as much enthusiasm as he could muster.

Before Bailey could get any further Megan spoke up as she gathered her purse. "Well, I think I'll let you two catch up. As much as I enjoyed my day with my sweet niece and her friend, I do need to get home and I still have a few errands of my own to run. Bailey dear it was a pleasure spending the day with you. I know you can't wait to show your mother all the cute outfits you insisted on having. You have quite the little fashionista on your hands Amanda. She just got so into picking out her clothes. I think we went a little overboard but like I told Bailey as long as she doesn't take off the tags it can be returned after this is over. Plus, the full closet is more convincing to anyone who might stop in for a visit." Megan said to Amanda while giving a Bailey a look that told him he had better play along if he knew what was good for him.

"Ok then I do not want to keep you any longer. I just want you to know how much I appreciate your help today. It really makes me happy to see you two getting along so well. When this is all over, I owe you big time." said Amanda as she let go of Bailey and set down the pizza before walking Megan to the door.

"Oh, I almost forgot Bailey made plans to spend the day with Candi at her hotel tomorrow so you'll have to drop her off on your way to work. You girls have a nice evening." Megan said with a wink to Bailey before leaving.

Amanda then picked up the pizza and may her way over to the table motioning her daughter to join her. "I know your excited to show me your new room and clothes baby but why not sit down and eat first. Megan texted me to let me know about your decision to diet and try and get back in shape. I think that's a great idea so I got us a small veggie pizza to share for dinner. Now come sit down and you can tell me all about your day." Amanda said with a warm smile.

Bailey grimaced inside at yet another healthy diet meal but settled in at the table and ate what he was offered with a smile. He then went through explaining how his day had been, keeping to the girlish character he was trapped as. However, choosing to leave out some of the more embarrassing incidents such as the dressing room accident and his new belly piercing.

Amanda just sat and let Bailey spin her tale of the day's events interjecting from time to time with various questions, and complimenting her on the newly pierced ears. Finally, once the story was complete, she let Bailey show her the newly redesigned bedroom.

Amanda was surprised to say the least as she followed her into the guest room. April had really out done herself.

"So, Miss April like got some people from your work to totally makeover my room mommy. Isn't it just like super cute?" Bailey said trying to stay in character and not get himself in more trouble. Then handed the note that was left on the dresser for her to read.

He wasn't worried about Mandy herself if he broke character but he was terrified that she would mention it to Megan and he couldn't risk what she might do.

"Well, I will have to remember to thank the team. They did a marvelous job. The room really suits you now sweetie and I love the flower design on the walls it is just so you." Amanda said enjoying the role of mother to a sweet little girl. She loved Bailey her boyfriend but they would have plenty of time together after all this. Her sweet daughter Bailey Ann was only here for a week and she was going to enjoy it while she could.

"Oh, mommy I almost forgot. Here I got this for you." Bailey said as she gave Mandy the best mom ever mug. "We played a fun game today with Candi and each bought stuff that like meant something to us and you like mean so much to me I just had to get it." beamed Bailey really meaning what he said he didn't think of her as his mother of course but he did love her and wanted her to know it.

Amanda looked at the mug and then back to Bailey. A tear coming to her eye. "Oh sweetheart I love it! I am so lucky to have you in my life." She said as she wrapped Bailey in another hug.

"Now I want to see all these new clothes you just had to have. It is ok that you got carried away any girl would with their aunt there spoiling her. Just remember not to take off the tags unless you have too." Said Amanda in a light admonishing tone.

Bailey quickly set about showing off his new clothes making sure to do as Megan had said and making it sound like he had picked them himself though occasionally mentioning that Candi had pick this or that.

An hour later Bailey was finally showing off the dress he and Candi got for their date. "So, Candi like wanted us to like match for our date because we could like totally be sisters. The boys even like said so." Before he could keep going though, he let out a long yawn.

Amanda having been thinking about just how much Bailey really seem to know about women's clothes was pulled out of her thoughts by the yawn. Seeing how tired Bailey looked and remembering that they both had to be up early decided it was time to bring the evening to an end.

"Sweetie I know you are having fun showing me all your little outfits but I think it is time we get to bed. Go put that away and go get changed for bed and I will help you with your hair." Amanda said.

Bailey at once glad to finally be done with this stupid fashion reveal and be able to change almost agreed before he remembered what kinds of pajamas Megan had made him get. He just couldn't let Mandy see him in them.

"Oh, mommy that's like really sweet of you but I'm like totally not tried and I can do my own hair. I thought I might like watch TV or something first." whined Bailey trying to avoid changing.

"Nonsense you look exhausted and we both have to be up early to drop you off at Candi's. Now I am going to go change myself and when I get back, I expect to find you dressed and ready for bed young lady." Amanda said leaving no room for argument as she headed to her room to change.

Bailey just wanted to die of shame but saw no other choice at this point after trying to find something he could stomach he settled on a pink lace baby doll with matching panties. It was still revealing but it was the most modest option he seemed to have. He quickly changed removing his outfit and removing the tuck kit before gently tucking himself into the little thong panties. Looking in the mirror Bailey was torn. On the one hand he absolutely hated this but on the other hand he couldn't resist staring at the vision of sexiness in front of him. Pink lace just barely covers his fake breasts and the silk bow in front scream girlie while also making him look like a present just waiting for some guy to unwrap. Suddenly realizing he was getting turned on looking at himself he turned from the mirror, just as Amanda came back into the room carrying a familiar teddy bear.

Amanda froze right inside the door way momentarily jolted out of the illusion she had been enjoying all evening. She couldn't believe what Bailey had chosen to wear to bed. He had always loved when she wore sexy little nighties and now, he stood there in one of his own. He was trying so hard to fill the role he had created even going so far as to sleep in something sexy and girlie just like the girl he had created would. It was simply amazing how dedicated he was to this.

"I saw this and thought you should keep it in here sweetie it was in the picture Derrick first saw of you and it really matches your new room." Amanda said placing the teddy bear on the left side of the bed. "Now have a seat baby and I will get your hair out of that braid so we can get some sleep."

Bailey did as he was told, blushing and squirming as Amanda stood behind him and gently un-did the braid and then brushed out his hair. While she brushed, she started humming a somewhat familiar lullaby he thought he remembered his own mother humming when he was a child. Stunned and embarrassed at his girlfriend seeing him like this and treating him like some little girl. He had to suddenly fight back tears when Amanda finished and wrapped him in a warm embrace.

"I love you, Bailey." Amanda said before wiping a tear from Bailey's face.

"I love you to Mommy" Bailey replied wanting this all to be over so he could show her just how much he loved her as himself not some teenage girl.

"Ok now I think we both need to get to bed morning will be here soon enough." She said motioning him to the bed. She gently tucked him into bed before turning off the light and making her way to her own bed.

Bailey just lay there fuming after Mandy left. He was a man damn it but she treated him like a baby. Frustrated and fighting tiredness he quietly got up and got his laptop. He needed to feel like a man. He opened up his browser and typed in his favorite porn site. Suddenly a red stop sign covered the screen. Attempt to access Restricted site warning issued. Then the browser was back on the home screen. Bailey cursed but didn't let the blasted program stop him. Trying instead to just search for one of his favorite types of porn. He typed in busty blondes and hit enter. As soon as he did, he was filled with dread. A second warning sign appeared but this time read second attempt at restricted access. Admin has been notified. Bailey felt fear grip him. The admin would be Megan of course and she would be sure to punish him dearly for going against her. Defeated Bailey closed the laptop and got back under the covers. Soon he gave in to his exhaustion and drifted into a fitful sleep.

As the night wore on Bailey tossed and turned eventually settling into a more natural position cradling the stuffed bear Amanda had left him. He was used to having Amanda next to him in bed and his body just held the bear just as he would when holding her while she slept.

While he slept his body was in turmoil. The three doses of high-level female hormones and the three doses of herbal breast enhancer were mingling and reacting to each other in a strange and powerful way. As Bailey slept his body struggled to hold on before slowly being overwhelmed.

The next morning Amanda went to wake Bailey and found him cradling the stuffed bear she had given him. Her heart swelled at the sight before she bent down and gently woke her with a kiss on the forehead. "Rise and shine sweetie we have another busy day ahead of us."

Bailey held the stuffed bear tight as he dreamed, the last two days weighing on his mind. His dreams were not his normal sort. In his dream he stepped outside of his old house where he lived with his parents. The area around him was a village, but all the buildings were smaller like for children. A horse ran by distracting him running down a yellow bricked path out into the distance. That was when he heard the voice of Mandy. "What will I ever do, oh what will I ever do?"

Looking to her she had her long blonde hair curled, wearing a poufy pink ball gown and a crown, while holding a staff with a star at the tip of it. Instinctively he went to the woman he loved to see how he could help, but before he could say a word, she looked to him. "The great and powerful Derrick Oz is in town with his daughter and he thinks I have one too, what will I do Bailey? Can you help me?" she said pleadingly. Nodding to her he put his hand on her shoulder and spoke. "Mandy I would do anything for you."

Mandy the good witch's mood flipped to one of glee. "Then you will need these for your journey!" she said with a wave of the wand causing his sneakers to turn into high heeled red sequenced shoes with a strap across. He wanted to ask why he was wearing them, but he knew they were so he could get to Derrick Oz. He wanted rebel and rip them from his feet but as he did a woman in black flew through the air on a broom. Even with green skin Bailey knew the witch Megan anywhere.

Hovering in the sky she pointed to Bailey. "I'm going to get you and take it all from you!" her voice cackling. He needed to flee from her or at least get her away from Mandy before she told her his secrets. He went to run but all he could manage was a sexy walk down the yellow bricked rode, one foot in front of the other and swaying his hips like he was inviting people to watch.

The cackling voice cried out behind him. "Get him my pretties!"

With a glance he saw articles of female clothing coming down from the sky toward him. No matter how hard he tried the best he could accomplish was to prance forward in the red shoes. The clothes overtook him quickly and swarmed over his body. The light fabrics felt wonderful on his skin arousing him, but in flash the swarm was gone and now he stood there dressed like a slutty blonde Dorthey.

Bailey wanted to yell and scream as he went to look down at himself, reflexively pinching each end of the skirt between his fingers as he looked over his body through long dark lashes and over a large bust. Instead of a scream or a line of curse words all that came was "Tee hee, I like love it!"

Glaring up to the witch he wanted to yell and give her the middle finger, but instead he only blew a kiss saying "Love you Auntie!" before feeling someone grab his hand and start to pull him away.

In front of Bailey was another blonde girl dressed just like him with the only difference being she was slightly taller and wearing black heeled shoes. He was forced to follow gracefully with a strut, her holding his hand pulling him along. Candi turned around and looked him in the eye, his green eyes meeting hers. "We like need to get to daddy, but along the way we can find some cute boys to fuck!"

Wanting to let go, wanting to shake his head, wanting to run.. Bailey could do none of it, but follow until he heard his phone notification go off form inside the basket, he wasn't carrying a second ago.

Pulling the device out he saw the picture of some one's cock, his mouth falling open in shock. Though as he did, he heard a giggle from the girl next to him. "Looks like someone wants it in her mouth. Let's invite him over with a friend!" the happy voice of Candi seemed to wash across the field they now stood next to, still on the yellow path but to one side of Candi was Ryan wearing a suit of armor and holding an axe. He leaned down and kissed the girl as she threw her arms around him.

To his side was August wearing a tweed suit that looked to be have weaved from straw. The taller man's arms wrapped around Bailey's waist and pulled him in kissing him hungerly and he could feel something pressing to his stomach, something that was hard and growing. When August pulled back, he looked Bailey in the eyes. "I am going to have you, and if Ryan wasn't here I would have you both!" his deep voice seemed to whisper to him. Even in the dream world he could feel his heart pounding and wanted to push the man away, but instead was pushed backwards onto a bed with a bedspread of dark sinister looking trees. August climbed atop with Bailey and a voice from behind him said. "This sounds fun!" and Candi seemed to wrap her arms around him from behind holding him in place as August came closer with his erect member coming closer and closer to his mouth. He didn't want to have it anywhere near him and wanted to run but Candi easily held him in place saying. "Little sister you are just going to love this." he opened his mouth to scream, but no sound came out and the cock started to go in.

That is when everything faded, he awoke to a gentle kiss on his forehead. A tiny bit of morning light came in through the blinds giving the room just enough light for him to make out Mandy.

"Rise and shine sweetie we have another busy day ahead of us." blinking as he looked up to the woman, he loved he smiled sleepily. "I was having a dream with you as Glinda the good witch and I was Dorthey and.. Somehow so was Candi." Amanda ran her nails through his long blonde hair and smiled.

"Sounds like a good dream, but you are back home in your bed in Nevada. Now time to get up princess, I have to get ready for work and you have a play date with your friend.

By the time Bailey got out of the guest shower, his shower for the week he once again reinforced the scents of jasmine and rose oil from the shampoos and lotions he has to put on after the shaving. A task he was not keen on at all. After it all though the memory of the dream had mostly faded, only lingering bits were something about Megan being a witch and him having red heels.

Showering with breasts and ones he couldn't feel was interesting, it was like he got to feel up a girl with nice C cup tits whenever he was alone. He may have jerked off right there in the shower if he didn't hear Mandy knock on the door reminding him, they had places to be.

Patting himself dry like he was taught he wrapped the towel around his waist and stepped out into the hall only to be caught by Mandy once again. "Young lady, we talked about this. No daughter of mine is going to walk around exposing herself." she said pulling the towel up and lightly pushing Bailey back into the bathroom. "I will teach you how to wrap your hair later, but for now we have to blow it dry." she said opening the cabinet below the sink and rummaging around till she came out with her spare hair dryer. After a quick blow dry, she stood behind Bailey brushing his hair out just like last night.

The feeling was relaxing for Bailey even if the scenario was ridiculous. "We will be brushing this every morning and evening at least forty times with this natural bristle hair brush, not one of those plastic ones, that will ruin your hair." she said happily smiling at the blonde hair with each stroke. If it didn't feel so good to have her do it, he may have complained, but mostly he just wondered why he never had her do it before. "Off you go now, get changed for the day and I will be along shortly to help with your makeup."

Tossing the large fluffy towel on the bed Bailey knew what the first task was, he needed to tuck again. He pulled out the Unclockable Tuck kit and followed the directions adding the pad to the sticky substance and sticking it to his skin just above his privates, a process that would be painful if he wasn't hairless. He then pulled it back and pushed up gently with his other hand to push his testicles back inside his body and sealed them in with the sticky T tape it was called and when he did it correctly as shown he was able to use his thumb to create a crease at the center like a woman should have. The process was not painful, but was as always uncomfortable and the kit said it would even hold in water, perfect for the day. With himself sealed away he opened his drawers to get a swim suit and had a thought. Mandy wasn't told they were swimming today and Candi wouldn't be telling Megan anything. He smiled and put it away thinking he could just say he forgot and maybe they could spend the day watching tv. Sure it would be shows he didn't like, but that is a far better than what was currently planned. To really sell it he needed to make sure he looked good. Pulling out some white lace cheekini underwear and a white lace push up bra he put them on. The push up bra really bothered him, he didn't want these things on his chest to look bigger, but he was not spoiled for choice. At least with the tuck kit the lace panties weren't be rubbing on him arousing him all day. Today was the first real day he got to dress himself as a girl and he kinda wish he didn't just make the decision to do it well, but best to do this than wear a bikini all day. Pulling blue blouse from the closet that had sparkly bits around the chest and a criss cross weave by the shoulders instead of sleeves he pulled that on and looked for a decent bottom. Deciding on the black jean button up skirt from the day before he was proud of himself. It looks like something Candi would expect him to wear, the saddest part was the shoes. Other than a single pair of sneakers that would not go with the outfit he was left with heels, so he grabbed a pair of strappy gladiator looking blue sandal heels. "Why are all the heels so stilettos, dammit Megan." he cursed under his breath and quickly redirected his thoughts, less they alone summoned the witch here. Before he went to Mandy, he needed to do something with his hair and he started to try to recreate what he did yesterday, but without the video it was difficult so he got little more than half way done and just put the rest into a pony tail. Turning his head in the mirror he decided it looked good.

Walking over to Bailey's room fully dressed for the day minus her heels she looked into see the feminine sight of Bailey admiring his hair that he had braided and put up. She was reminded once more how hard he was trying for her, making the mistakes earlier with the towel seem like normal unthinking gaffs. "Aww Bailey, you look beautiful like a princess." she said happily walking in with a makeup case. Bailey only scrunched up his face at the comment. "You know it is a compliment sweetie, my father God rest his soul use to call me that." she said putting the case down on the vanity and squatting down behind Bailey so their cheeks touched looking into the mirror together. "With the way you look now it is easy to see why this is working. You have green eyes to contrast my blue, naturally darker eye brows and I have a longer face, but we really do like we could be related. You know how I always wanted kids, I know this is only pretend and something you did not want, but for this week. I am happy to have you as my daughter." she said hugging the disguised man and then kissing him on the cheek.

"Now in this case I have some makeup you can keep in here, some of it is mine. Some of it is what Megan brought over from your cousin Becky. Let us get you looking even more pretty for the day. Like they say, a lady should never go anywhere without putty on her face."

You are lucky to have clear skin Bailey so you don't need to much, but we all have bad days. What you do need to know about is some basics, you need to have eye liner, mascara and lipstick, anything more only makes it better. I will try to get off work on time tonight so I can touch you how to do your own makeup. Aww do you hear that Bailey; I just love saying things like that out loud." she ended the lesson with another hug. On the way out the door Bailey tossed a few more of the pills from Megan into the purse he was borrowing from Mandy, then popped one in his mouth and one of the vitamins from Candi dry swallowing them both.

Soon enough the two girls were in the Toyota coupe driving to the hotel where Candi was staying. Amanda watching the morning traffic and Bailey looking down at his phone texting his new bestie. The topic of this morning's rambling was about a Cosmo quiz that she just took and Bailey was doing now about what your dream wedding dress says about who you will marry.

Question 1: Does the dress have any sleeves or straps? Answer: Nope! I'm going strapless.

Queston 2: How long is the skirt? Answer: Floor-length, Obvi!

Question 3: How poofy would the skirt be? Answer: I want a decent amount of poof.

Queston 4: Would you ever something trendy, like a two-piece crop top-skirt combo or jumpsuit? Answer: Nah, That's not for me.

Queston 5: What's your shoe game looking like? Answer: Some pretty heels, for sure.

Question 6: Veil or no veil? Answer: yes. I need my Meghan Markle moment!

Question 7: What kind of makeup do you want? Answer: I can never say no to a statement lip.

Question 8: And finally: what's your main accessory? Answer: A pop of color, like some flowers in my hair.

The results of the quiz were: You'll marry someone ambitious and romantic!

Bailey groaned and it caught Amanda's attention so he had to tell her what he was up to. "Oh like Candi found a quiz that would like tell us what kind of man we would marry depending on our answers." and then proceeded to go over the options he chose. He didn't want to, but his girlfriend had an amused look on her face and asking him probing questions about his answers. The car ride went from peaceful, to annoying with the quiz to downright dreadful having to talk about how he wanted his wedding dress one day. The trip to the hotel was only about fifteen minutes thankfully, but before he could get out Amanda put her hand on his arm. "Forgetting something?" she said smiling wanting what was coming and to keep him in character. Bailey leaned over and gave Mandy a large hug. "Love you mommy, thank you for dropping me off and have like a good day!" with that he thought he was done but she stopped him again. "Bailey, Mr. Connors is going to give you a lift home. You know how important he is to us, make sure you treat him like how Candi has treated me, with kindness and respect. Make sure you thank him." Another quick hug was given and a reply. "Like of course mommy, I'm a Best so that is what you can expect from me!" it was a cute line that Amanda just loved. She didn't pull away right away, instead watching Bailey strut into the hotel. "I wish Bailey would stop walking like that." she said pulling out back into traffic on the way to the office.

Bailey heard the click on his heeled shoes on the tile floor echo through the lobby, with every step and exaggerated sway of his hips he could feel the pull and jiggle of the glued-on breasts and swish of his hair hanging in a pony tail. Pushing the elevator button with his French nail tipped finger he gave himself a sour look in the reflection of the sliding metal doors. He did look like the fashionista Megan claimed him to be and Mandy assisted in creating this morning with the makeup, she even used the lip plumper one from the other day before having him apply his own lip gloss.

Stepping in he went up to the fourth floor and then came to room four seventeen and knocked gingerly hoping that he could just claim no one answered so he could go home. Even as he did the act, he knew it wouldn't work considering the electronic leash everyone carried around in their pockets, no one could just get out of touch and disappear for a while like they used to.

The hotel room door flew open and the teen girl on the other side lunged in for an attack, jumping off the ground in her bare feet Candi hugged Bailey making her usual high-pitched noise of excitement before pulling him inside. As the door closed behind them Candi looked Bailey up and down raising her eyebrows. "Wow girl, you look hot." she said approvingly before her eyes looked at Bailey's white purse and noticed her friend did not have a change of clothes with her.

"You like wearing your suit under your outfit?" this was where Bailey hoped to be able to blame the air headed girl to get out of the pool side day. "Like thanks, never know who you are going to meet and umm like what do you mean?" Candi just giggled and motioned to herself wearing a white bikini top and a black sarong with large white dots around it. "The pool, you silly ditz, did you like forget?" she said playfully to Bailey. Twisting some his finger through his pony tail Bailey returned the giggle and hated himself for it. "Oh like yeah, I was just looking at that quiz you sent me and was just trying to picture the perfect white gown and I guess I just forgot. I'm like totes sorry Candi it looks like no pool for us today and I was like so looking forward to it." Bailey channeled all the shame he felt from what he was wearing into his words, like he really was embarrassed to have forgotten the entire plan for the day.

Leaning forward Candi gave him another quick hug and still had a smile on her face. That sweet girls smile made him feel like the bottom had fallen out from his stomach. "We all forget things, I like do it all the time. Daddy says we all should work with the tools God gave us, and how lucky I am to have his drive and ambition even if I'm not smart like him. He of course would never say that last bit, but I know who I am. We make a great team Bailey, both of us pretty and know how to work it to get what we want. Now let big sis find you something to wear to the pool!" it was one of the most insulting pep talks Bailey had ever gotten and all he could do was smile like he agreed and pretend to be thankful this seventeen-year-old girl was the leader of their little duo.

When the green-eyed teen was finished with Bailey, he was wearing the red and white striped bikini she bought at the mall the other day and a short white wrap and still the pretty blue heeled sandals. The outfit exposed his new belly piercing and she replaced the studs in his ears with large silver hoops, the unfamiliar weight to his ears adding just another thing to his list of things he hated. "OMG like you are so hot, and those blue shoes with that outfit are just going to force every boy to look at you. I'm like totally jealous. Just wait till your diet pays off and you will have your pick of the men." Candi said adding a giggle at the end as she sat at the edge of the bed putting on a pair of wedged, heels. Remembering how she gave away a pair of wedges to him it made him wonder just how many shoes this girl brought with her for a weeklong trip. Though considering who her father was and how the hotels suite was the same size of his apartment he knew she could afford them.

Bailey watched the girl bend down at the waist to pick up a large canvas bag, her as so close he wanted to touch it. The sight caused a stirring down below so he distracted himself from the view to pull out a pill and swallow. He wondered if the pills were working to keep him from getting hard or if they were working and he would just be getting hard more often. He wasn't sure, but he did wish he was able to get off last night. "Okay, I have like everything we are going to need to make sure we tan and not burn. Daddy even like talked to the hotels store to make sure what we got for you would help you tan and not burn." she said walking to the door. Bailey tried to look anywhere but the teens rear end as she walked in those heeled shoes. One thing that did catch his eye was a bottle of whiskey on a counter that he really wish he could take a pull from to make this day easier.

By the pool side the two girls were not alone, a husband and wife had just arrived as well with their little boy who couldn't be more than six or seven. The husband made a comment about forgetting the bottles of water in the room as the mother applied thick white sunscreen on the little boy in a floppy pool hat. Ever helpful Candi pulled out a few bottles of water from her canvas bag. "Like here you go, no need to go up we brought extra!" the mother thanked the sweet girls before going back to what she was doing, with trying to wrangle the energetic child and get him protected from the sun.

Both of them removed their wraps and started to apply the lotion Candi brought and as Candi turned to start rubbing it into Bailey's back, he felt like he was going to melt as he small soft hands on his body and hope the pill he just took would kick in sooner rather than later. The wish turned into a prayer to anyone who was listening when it was his turn to rub the lotion onto her soft skin. The tuck kit did its job keeping him in place, but every passing second was just an extra helping of feeling uncomfortable from the building pressure of his dick trying to gain its freedom. When it was rubbed in Bailey backed off and sat down on one of the reclining pool chairs and thinking if he could get away with opening one of the large umbrellas so he wouldn't have tan lines from a woman's bathing suit. The only thing he could come up with was the excuse he burned easy, and he did. But her dad seemed to already consider that. So, instead he pulled out the cheap girly dollar sunglasses he got at the mall and laid back on the pool chair.

"One last thing sis!" Candi said as she put a little star sticker on the left side of his stomach by his hip. He wasn't sure what that was for, but she seemed excited and happy so he only smiled and giggled at her "Like thanks, I love stars. I used to go camping with my dad when I was.." he trailed off for a second stopping himself from saying teenager. The pause just made Candi think her friend was choking up on an emotional memory. "When I was younger and we would have our sleeping bags and warm blankets and would look up into the sky watching the stars." It was a memory Bailey really did love and wasn't' really sure why he was sharing it with this girl, but it playing out in his head and how his dad would give him an extra blanket to make sure he stayed warm made him tear up and cry a little.

He wasn't sure why he was being so emotional, but Candi was helpful as ever living his pink sunglasses and dabbing at his tears with a tissue. "It's okay, its okay I can tell you loved your daddy. It sounds like with your mom working you spent a lot of time with him, no wonder you were a tomboy for so long." the feeling of the girl touching his arm comforting him at the loss that was not new by any means reminded him of how Mandy was there for him when he lost one parent after the next. He remembered Mandy touching him the same way and how he wanted to do anything, but think of the memories and how he would pull her into his embrace and start to make out.

Without really thinking about it he leaned forward to kiss Candi and pull her close. Their lips never met as she turned her head to the side and moved in to hold her friend tight. Bailey was happy the kiss never happened, that was a mistake and would have been a costly one.

Holding bailey tight Candi ran her fingers through her friend's ponytail, just whispering. "Everything is okay, I'm here for you." the words were meant to sooth her friend as she started to gently rock back and forth. Candi could remember needing this too when she lost her mom many years ago, but unlike Bailey she had friends to lean on and she knew not everyone was strong like her, though the emotions of the moment in the embrace still brought tears to her own eyes she was able to hold herself back from opening crying and ruining her makeup.

She was just happy she was able to be here for her friend and had tissues handy to prevent Bailey from ruining her own. When Bailey seemed to be back under control she pulled back and smiled warmly. "See all better, I bet it feels good to get that out. Later you are going to tell me all about your daddy, but we will make sure our makeup is off first so we can both have a good cry. Does that sound good?"

The emotional release did feel good so Bailey nodded to the girl. He wasn't sure about opening up to her, he didn't even really do that with Mandy. Though he didn't really think he needed to, she knew most of the stories when he told he when they started dating and around the dinner table when he invited his girlfriend over to dine with his family. The memories just seem to take on a different shade when thinking about it in the past tense, knowing he couldn't talk to his parents ever again or create any more of those memories.

"Okay, but later." he said sniffling and trying to contain his out-of-control emotions. The doses of estrogen in his system were having an effect on his mental state, but without really knowing that is what he has been taking he had no way to put that together.

Gaining control of his emotions Bailey lay back down on the deck chair with his eyes closed just trying to let his mind drift off from the thoughts of his parents or his current girly state. It seemed like he just closed his eyes when he heard the sound of a phone beeping and Candi saying. "Time to turn over sis, need to be nice and even." without a word he followed her direction and let his mind wander, as he enjoyed the warm sun. This time he wasn't given the peace and quiet, Candi wanted to talk. "For like your diet, what did you have for breakfast this morning?" opening his eyes from behind the sunglasses he looked over to Candi. She was laying on her belly, sitting up on her elbows and looking down at her phone. "Nothing, at most I ever have is coffee and I haven't' had that in a few days." no wonder he had felt so tired the last few days, it wasn't just this girl stealing all of his energy like a sort of vampire. He had been so distracted he hadn't made a pot of coffee.

"Hmmm, well cutting out the coffee was a good start, but you can't just skip meals to starve yourself into being thin. I'm like here for you and if you're dieting so am I, but we have to do it right. Do you like want my help?" she still never did look over from the phone, her fingers just tapping away rapidly on the little screen. He wasn't sure how she used it so quickly with those nails, he could use his if he went slowly. Heck just about everything he did had to be done slowly, he recalled trying to type on the keyboard to his laptop and how he ended up just pecking with one finger at a time.

"OMG that would be like the best." he replied in character, already positive this girl was already going to control what he eats whenever they were together for the rest of the week thanks to that bitch Megan and Candi's helpful attitude. "Okay like good cause I am ordering some things to help us, text me your address real quick." arguing with this girl was like trying to convince a train to swerve off its tracks or well his mind trailed off for a second, he guessed also like arguing with either of the Best sisters when they made of their mind on something. So he pulled out his phone with its pretty flower case that seemed to have become his now instead of Mandy's, and gave the girl what she wanted.

"Okay, like listen. I am having something shipped here and your place. It is local and should arrive today for us. I was looking into it while you were having a little cat nap. We are getting some pre-made smoothies, the first one is Mango Ginger Kale and like its only one hundred and seventeen calories. I have tried something like it before and this one has the mango so it shouldn't taste as bad. That one we will drink three times a day, and like one more. It is a kale blueberry smoothie, but it like also has half a banana in it. That one is two hundred and forty calories, so it is for like only once per day. Lastly, we have some honey cinnamon tea for only eleven calories, that is for like before we go to sleep. It will help us not feel so hungry, but we can like have a mug of it at least one other time in the day if we like really feel a craving. That is like ordered, what do you think?"

The answer to that was it sounded horrible, he didn't want to have kale in any sort, and really didn't want to go down to a diet of six hundred calories a day. But he figured it was only for a week and only when he was near her. Sure, Megan got Mandy on board for the diet train, but she wasn't here to learn how it was supposed to play out. "Sounds like, not much." he said honestly.

"Yeah, totally, but way better than your not eating method and you better not tell me you have been making yourself sick to cut calories." the voice wasn't stern it had concern in it. "I would like never do that, I only want to taste my food once thank you." he mocked making a gagging motion that brought a happy giggle to the blonde next to him.

The laughter died down when a shadow came over Bailey followed by a woman's voice. "Pardon me, I wanted to thank you two again for the water and well ask if you could do us a favor." rolling back onto his back and sitting up Bailey looked to the pretty if not plane looked dark haired woman and her son, and noticing the husband was nowhere in sight. "I overheard you to talking a little and was wondering if you could watch my little Mikey for an hour or so. I would be happy to pay for you to babysit, it is just that me and Arnie haven't had much time to ourselves lately and we planned on my mother-in-law coming with us to spend time with Mikey, but she wasn't able to join us. I wouldn't normally ask like this, but you two seem like such sweet girls and I know you are staying here too." Bailey looked at the woman and then to the child and was ready to let her know that he did not in fact want to watch some kid while she goes and has sex with her husband. He wasn't able to get any while stuck like this he sure as hell wasn't going to enable someone else to while playing babysitter. But he should have known that wouldn't be the case, Candi was ever the helpful person with a big heart.

Aww that means a lot that you would trust us like this. I tell you what, the two of us will watch little Mikey here so you can go spend time with your hubby. Let me give you our phone numbers so you can check in on him if you need and we will be here or in room four seventeen." she said standing up and padding over to the older woman giving her trademark warm smile, before squatting down to look the child in the eye. "That is, if Mikey here is okay spending time with two girls?" the little kid looked between Bailey and Candi and nodded his head and spoke. "You two are pretty." the compliment caused a squeal of delight from Candi who hugged the boy. "Look at you Mikey, your mommy has already taught you the right way to speak to girls."

Adding a layer of sunscreen instead of the tanning lotion the girls got into the pool with Mikey, who it turned out was eight, but a little small for his age. The three of them tossed a ball around, played Marco Polo and just generally swam around, but when Mikey got tired, he latched onto Bailey. The little man wrapped his arms around what he thought was a pretty girl's neck and insisted she hold him.

Holding onto him was easy in the pool, but carrying him out of it was more taxing. Bailey knew he was never the biggest man, but he felt he should be able to hold onto a small eight-year-old, but he could feel his arms burning. Candi laughed at the sight of her friend struggling to hold the child. "I would take him, but it looks like Mikey knows who he wants. You should just shift him so you care holding him on your hip though.. Yeah like that!" she said pulling out some peanut butter crackers for the three of them to munch on. Even as Bailey sat down though the little guy held tight with his head resting on the feminized man's chest. Taking a bite of the snack Bailey realized how hungry he was and didn't want to bring up the diet just in case Candi would take away the small morsel of food. As if reading his thoughts though she brought the subject up.

"Enjoy the carbs while you can girl, it will be your last for a while." she laughed, but was still quick to enjoy the crackers herself.

They stayed like that for a while with Candi pulling up another quiz about what your taste in shoes says about you. Most of the answers Candi selected for Bailey before he could answer saying "Oh I know this one for you." Some of the questions were..

Question: Where do you go shopping? Answer: The mall

Question: How much are you willing to spend on shoes you have been eyeing. Answer: $500+. Bailey knew he would cause had had before when buying name brands for Mandy back when he managed a store.

Question: Do you wear shoes for style or comfort? Answer: Style

Question: How tall are your highest heels? Answer: six inches.

Just two days ago he could have said no heels, and now it was so much worse.

Question: You rush to the supermarket to get a few items, what kind of shoes would you wear?

Answer: Stilettos.

That was not answer he wanted to say, he said sneakers but Candi just rolled her eyes and spoke. "You aren't fooling anyone." the end result was the answer "Sexy" saying you enjoy wearing heels, strappy sandals and espadrilles, which says that you exude confidence, and your sex appeal makes your desirable by men and woman alike. Out on a date or walking your dog you always dressed to the nines.

"That is so you, first you got August wrapped around your finger now you have Mikey." she said giggling. The boy's fun though eventually came to an end when his dad came down to get him. "Looks like you had a fun day their champ." the child nodded and was hesitant to let of of Bailey, but soon gave in to his father. "I can't thank you enough for the time girls, it isn't a habit of ours to let a pair of sisters babysit for us without getting to know them first." he said holding out his hand with a hundred-dollar bill. Candi took the money and thanked the man and smiled holding up the bill in front of her to Bailey when he walked off. The move surprised Bailey, he thought she would have turned down the money.

"You always are helping people, I thought you would turn down the money." he said perplexed.

"This is money earned girl, never ask for money to help another. But if they want to reward you for your time and skill than it would be an insult to them and yourself not to accept. Besides we can use this to get a massage later!"

"Let's head back up to the room, but first." she said pulling the sticker off Bailey's stomach and then her own. Without the sticker he could clearly see a lighter spot on his skin in the shape of the star. The sticker was to leave a tan line of the symbol, he felt so stupid for not considering it. He remembered seeing images of girls with little playboy symbols that were lighter on their tan bodies before and just didn't put it together. "For our fair skin a light tan like this is perfect, we want to enhance our natural beauty not change it." she said it like it was a fact and not an opinion as she put her shoes back on. Following suit Bailey put back on his blue heels and wished it wasn't becoming a regular thing to be walking with his feet at such an angle.

Back in the room Candi made sure they both had a tall glass of water to rehydrate and the sight of some water dripping down her chin and falling to her sun kissed mostly exposed sweaty breasts made Bailey look away to grab another one of the pills Megan gave him. Popping one into his mouth Bailey guzzled down the glass of cold water. "Someone was thirsty, must have been hard work playing mommy for little Mikey." she giggled while Bailey considered just flicking the teen off. "Like okay, let's get cleaned up. You can use the shower in my room and I will use the one in daddy's."

Candi took a few pieces of clothes from a dresser as Bailey just looked at himself in the mirror. He was inspecting the damage being in the sun caused. His skin was still what you would consider pale though it at least now looked like he saw the sun once in a while, the real telling mark was the little star shape left behind from the sticker and the strap lines from the bikini top, he noticed moving the piece of clothing to the side. Coming up behind him Candi put one arm around his waist and stood to the side smiling into the mirror. "Girl, we look hot and if you are worried about the tan lines, we could always use the hotels tanning beds and go topless." the large hoop earrings swayed as Bailey shook his head not wanting to see Candi topless, while at the same time wishing he could. "No, like it's totally fine, just something new for me." Candi kissed his cheek and smiled saying she would be right back and how much fun she was having.

When she ran off Bailey closed the door with a sigh glad to have some privacy even if it was odd he had it in her room. With a second to himself he knew what he wanted to do. Opening the bedroom door he moved over to the bottle of whiskey he saw earlier. Opening it up he took a swig directly from the bottle. "Ahhh" he said enjoying the burning sensation in his throat. He took one last pull to help him get through the rest of the day before capping it and heading back for a shower.

Bailey didn't spend any extra time in the shower, wanting to make sure he beat the girl back so he could get dressed without her around and as he slid his lace panties back on, he was surprised the tuck kit's advertising was right with it holding up even from water and then he mentally kicked himself for thinking of the white lace girly underwear as his even if it was true. Once the blouse was on, he looked in the mirror again and realized how much of a mess his hair was.

He had forgotten about the braid he made this morning and when he ran the towel through his hair it made a mess. With a sigh he pulled the braid apart as he walked to the large windows on one side of the hotel room and looked down to the pool four stories down. "Spent hours at a pool and I'm positive the only reason we went in was to play with the kid." coming into the room just wearing her own panties and bra Candi only head the last four words and saw her friend gazing down to the pool below. "Aww, it's so cute that you enjoyed playing with him. I'm sure you will be a great mom one day." Bailey spun around surprised by the almost naked and quickly averted his eyes to the floor. "No, no thank you." the entire look just made it look like Bailey was embarrassed at the thought of being a mom. "Not any time soon of course, you still have to find the right man to marry." this was not a conversation he wanted right now or ever so thinking quickly he balled up his towel and tossed it at Candi. "Put some clothes on so we can get some lunch." Candi caught it and tossed it back hitting her friend in the face and laughed happily, the act cut the tension enough for Bailey that he laughed along with her. Getting ready Candi put on a black mini skirt that had four buttons at the top, a dark blue halter top and some cute strappy heeled sandals.

Once the two girls were dressed Candi went into the little kitchen and pulled out two granola and fruit bars and passed one to her friend. "Today's lunch!" looking down at the small bar in his hand Bailey looked back to Candi pouting his lips sad like at what he was just told. "That look works on my daddy, but it isn't going to work on me girl. We had those crackers an hour ago, so this should hold us over."

The two sat around the tiny table taking a bite of their bars, when Candi put a box of tissues on the table and soon as Bailey was done with his tiny meal she said. "Time to spill it, you like obviously need to get stuff out. So, like tell me about your daddy." Bailey forgot he had agreed to this, actually he wasn't sure if he agreed or it just felt that way because Candi said they were going to do it. "My dad was a small man, just I guess an inch taller than me, but he had broad shoulders long blonde hair, a full beard and well that is where I got my eyes from too." growing up it bothered Bailey that he inherited the shortness, but not the ability to grow a full beard or the broader shoulders that allowed his dad to put on the muscle.

"He owned a small department store, but was hardly ever there letting... others he trusted run it. They had a good selection of high-end clothes and shoes, I loved being there." Bailey thought of the years running the location and how good it felt to be in charge, and in control unlike now. That and how many girls he got to be with, customers and employees, sure some of the girls only did it so he would give them a raise, but he always felt it was a fair trade. While the statement to Candi just made it seem like this was where he got his love for fashion.

"Well, he also like owned two horses when he was umm healthy. We weren't wealthy or anything, the store was small and the horses were kept at someone else's stable we rented stalls from. Growing up he taught me how to brush and saddle the horses, my favorite was Cherry, she was a Chestnut.. I got to name her. Dad once told me how their hair is actually a shade of red, but it looked that way because of their brown skin. So that is why I named her that. She was a sweet horse that I would run around in a field with... did you know horses play a lot like dogs. We had some large balls around for us to play with and she was always quick to nuzzle anyone she thought might have something sweet for her to munch on. He was a busy man a lot like Man.. Mommy. Spending time with him at the stables and when we would go out on rides or camping is when it was just the two of us."

The memories seemed to bringing emotions in like a storm and Bailey was having to use his fair share of tissues. Thinking of these things had made him sad before, but nothing like this. He did have to bend some truth and leave out his real mom from the discussion, but he felt like he needed to get it out now that the damn was flowing. "My dad and umm Mommy were never married, but my dad did eventually marry someone else. She was a sweet woman tall and rail thin with a smile that seemed to make the world just a little bit better for anyone that was lucky enough to be near it. I spent a lot of time with her at the store, she like wasn't the smartest person, but she had the biggest heart. They both ended up getting sick.. Cherry was sold off to pay some of the bills.. But in the end, they both left me and the only one I had left was Ma.. Mommy. I haven't ridden a horse since." Bailey wasn't sure when it happened in the story, but Candi had moved to a seat next to him and was holding him.

"I'm so sorry you had to go through all that, seeing people you love get sick and die. It isn't easy..." while it felt good to get that out, he did feel a little bit like a heel remembering this girl lost her own mom a similar way. "My mom was like one of the prettiest women ever, she had golden hair except for one little wisp of white in the front that she said she always had. I remember her keeping it in a short bob style. She was the type of woman that always wanted to look her best, she said no matter how sad or dark the world was if she made herself look good to face the day it made everything else easier to handle. Even when she first started to get sick she kept doing that.. Till near the end. I remember being mad at her because she was only in her pajamas and how daddy was spending all his time with her. Now I feel bad for ever feeling that way. Can you imagine being mad at someone because they are sick and you aren't getting the attention you like wanted."

It was Candi's turn to cry and the poor girl didn't just cry a little. Bailey found himself holding her as she bawled into his chest. "No.. Candi look at me. Candace look at me." he said being firmer with the formal name. "You were young and didn't know better or understand. You are a good person, look at what happened today or how you have helped me." he really wished she would stop helping him be more girly, but he needed to cheer this girl up, her crying was making him cry and he was pretty sure that was only making Candi cry more, it needed to stop. "When someone says to be kind to others anyone that knows you could use you as an example. That like old show, Mr. Rogers.. He would always say when bad things were happening to look to the helpers. That is you.. Candi you are someone Mr. Rogers would be proud of." the statement made the girl smile, but the tears kept on coming, now being more tears of happiness.. Tears that also made Bailey cry.

When the two of them had cried it all out they went to wash their red and puffy faces. Fresh faced Candi hugged Bailey tightly whispering. "Thank you Bailey, I wanted to help you and like I guess we both really needed someone to lean on. I'm so happy you are my friend." when she pulled back, she smiled brightly, but didn't let go. "You are a good little sister." when he went to protest the statement Candi held firm and started to tickle his side until the two of them ended up falling down on the bed in in Candi's room. "Okay, okay you win! You win!." he said between gasps for air unable to take it anymore. "Say it!" she replied not accepting the win just yet. "I'm the little sister! Okay, you win, I'm the little sister." Candi stopped and pulled back from her friend and stood over Bailey as he tried to get his breathing under control. "Good now as the big sis, I'm going to give you a makeover and help you to learn how to do it yourself."

Getting herself done up all first Candi explained what she was doing and why with each application of makeup while Bailey watched. He wasn't interested in learning, but wasn't sure if she would try to quiz him on anything later. When she was done with herself, she helped Bailey set her hair into two loose pigtails before adding some light makeup with pink eye shadow and pink lipstick. "Okay that should do it!" she announced. Looking in the mirror Bailey felt uneasy and remembered how Megan and Mandy tried this hair style first the day of the picnic and decided against it because it made him look even younger. Seeing himself now with the makeup and hair style he had to agree. "Okay it is time to do a video for like youtube. First, we are like going to do introductions, then we clean you up and shoot you doing this same look. Then we do another one with me doing something more dramatic for a nighttime look. Oh, this is just so perfect!" she squealed.

"Hey all you wonderful people, it's like me Candi C here and I have my bestie with me again today. This is Bailey, she is like my little sister. Say hi to everyone!" smiling sheepishly, Bailey waved to the camera Candi had set up on a tripod. "Just like happy to be here."

"Today we are going to show you a few looks on my beautiful model here. First she will show us this cute light day time look then I will show you what she can look like when we amp it up for a night out on the town." with that Candi ended the recording and handed Bailey some makeup wipes. Once his face was makeup free, she got him all ready with the makeup and started the camera again, letting Bailey be the one to talk to the camera and explain what she was doing. As bad as this was, Bailey was happy he paid attention earlier, if he didn't, she might have gone through the lesion once more so this would go just right. When today started he had no idea his face would be going onto youtube for a makeup lesson, at least no one would recognize him.. He hoped. "And like that is how you get your makeup to look like this!" he said twirling his fingers in one of his pigtails before Candi cut the video feed.

"Girl, you are natural! The audience is just going to love it when I put this together, and you wouldn't believe how easy it like is. All you do is open this program here and put one video behind the other and it like makes it into one video for you to upload, it is like super easy even we can do it! The next video was Candi doing his makeup again, but this time for the dramatic look and once they had all three videos Candi used her program on her laptop to bring them into one.

While she was uploading the video and waiting for her dad to approve of the new video the front desk called up to the room to let Candi know some packages had arrived, so off the two of them ran to get the multitude of boxes. Opening them up they saw the smoothies in individual servings and some ice packs to keep them cool. "OMG, I just had the perfect idea.. We can upload this as a diet video set for you!" Bailey looked perplexed. "For me?"

"Of course! I will make you your own channel and we can upload the video we just made to your channel too and then like do one for your diet, this will be so good. You are just going to love doing this!" It wasn't long before Bailey had a new email address of SweetBaileyFlowers@mail.com a youtube channel named 'Bailey Ann's' and two videos. The first being the same one they just uploaded but with a different introduction.

"Like hello everyone I'm like Bailey Ann and today me and my older sis are going to show how to do a cute day time look and a dramatic nighttime look." Bailey didn't tell Candi to introduce herself, but she did anyways. Once they put it all together, they were able to upload the video right away with Bailey being eighteen and not needing a guardian's approval. They re-watched it all together and Bailey kicked himself, in the video he didn't say big sister, he said older. Jesus and the way he looked with the cutesy makeup and pigtails he didn't know what people were going to think.

The second video Candi had him do back in the bathing suit that was uncomfortable to put back on being still damp. In it the two of them showed the three different drinks that would be their diet for the week, the tea to help curb hunger and the two smoothies. The one with blue berries didn't taste to bad, but the other was not something Bailey ever wanted to ingest again. Both girls ended up drinking half of each smoothie as they explained how it would help get the perfect beach body.

Once over Bailey went to go change while Candi uploaded the new videos to their accounts. It seemed Bailey Ann now had an online presence, and Candi had the passwords. He thought how this day couldn't get any worse after shooting those videos and just having redone his makeup for the maybe sixth or seventh time thanks to those videos.

It got worse, he shouldn't have even have let the thought brew in his mind, he thought his only saving grace was that he didn't say it out loud or things would someone be worse than they just got when he came back into the room and found out the news. "The videos are looking like super good and I like shared them with Auntie Meg, and guess what?! She loved them!" he wasn't sure how Candi got Megan's number till he looked over at his phone with the screen showing his contacts showing the name Aunt Megan Lily Best on the screen. That bitch, he thought, she had even changed his contacts on his phone. Before that only read 'Meg the bitch' and damn did Candi not know what personal space was just going through his phone like that, what if she saw something she shouldn't have.. God what if she had instead gone through his photos, he had a few dick pics he had sent to woman online. He really needed to add a password to that thing.

"Like of course she did, Aunty Megan only wants the best for her niece." or what will torture him the most he added mentally.

Bailey wanted more than anything for this day to be over, all this excitement, emotions and being in the sun had worn him out. He wanted nothing more than to crash in his own bed, fuck his girlfriend and fall to sleep and go back to his normal life. Instead, Candi was dragging him down stairs somewhere, he said where they were going, he just wasn't paying attention. When he asked her to repeat herself, she only rolled her eyes and giggled at him and pulled him along instead of giving an answer.

What happened next would be the best part of Bailey's day. Candi used the hundred dollars they earned to book a couples massage and said she would use the cash for a tip and the bill could be sent to the room. When a large Hispanic man named Hector ended up being the person to rub Bailey down, he was distraught the idea of a six-and-a-half-foot man running his hands over his now feminized body was not his idea of a good time. Though by the time it was done his body felt like jelly and he just couldn't help but blush when he asked if there was anything else he could do for her or if she wanted to come again to see him before they left the hotel. On the way back up to the room Candi was mostly quite smiling to herself, though he kept noticing her giving him the side eye. "What.. Why do you keep looking at me like that?" he said to her finally needing to know. "He was a little old for us, but I could tell Hector liked you.. I'm a little jealous. Mary was good, but I'm betting having those large strong hands on you felt better." Bailey only groaned in reply, one that Candi took as an agreement.

When Derrick came back to his hotel suite, he smiled seeing the two girls sitting on the couch next to each other, both of them falling asleep leaning on each other while watching RuPaul's drag race. It wasn't late, Derrick had left the office a little early to make sure to get Bailey home in time for dinner with her mom. He slowly put his laptop back down on the kitchen table and pulled out his phone and took a photo sending the precious image to Amanda.

Derrick: Looks like they had a good day and wore each other out. Amanda: Aww, that is the cutest thing I have seen all day. Thank you for sharing.

Walking over to the girls he turned off the tv and leaned down kissing Candi on the forehead. "Hey princess, I'm home." his teen daughter slowly fluttered her eyes open and looked up smiling a small tired smile and sat up causing Bailey to slump over on the couch waking her up. "I saw the video's you girls uploaded and I approved them for you Candace. I'm glad you two had such a good day together. I'm sure you two would love to stay together longer, but maybe a sleep over can be arranged another night. For now, I need to get Bailey home." Candi stood up and stretched before giving her daddy a welcome home hug, while Bailey watched them with half open eyelids not sure of when exactly he fell asleep. Still in his sleepy state Bailey licked his strawberry flavored lips trying to wake up and remembered what Mandy told him this morning about treating this guy like Candi treated her. He thought back to the picnic when Candi hugged Mandy and what she said.

When Candi let go of her dad Bailey gave the larger man a hug himself and stood on his toes to give the man a kiss on the cheek. He wasn't a fan of what he was doing or the feeling of pressing his lips to another man's body and feeling stubble, but he figured this is what Candi would do. "Thank you for like today, Candi is like the best." when he said best it caused Candi to giggle and say "No, you are the best." making a joke about his fake last name.

After they said their goodbyes, Derrick took Bailey home in his rental car. While looking out the window still trying to fully wake up after his afternoon nap he heard the man talking to him. "It is nice to see Candace taking such a strong liking to you, I can tell you both are having fun. She has friends at home, but the two of you seem to have something special. Like this sister thing I saw in the videos, how exactly is she your older sister?" the mention of his gaff made him blush, here he was a twenty-five-year-old man pretending to be an eighteen-year-old girl and referring to a seventeen-year-old one as older.

"Umm that like just came out, you see um where to begin. Some boys thought we were sisters and she liked that and she says she is the big sister because she is like half an inch taller than me even though my birthday was like last month and hers isn't until next week. But like she is more.. Outgoing so she tends to lead.. So that is why she says she is the big sister, but the older thing was like just me saying the wrong word." Bailey was mentally congratulating himself he navigated that while staying in character, though he wanted to say pushy, not outgoing. "That is my Cadence, always taking the lead and I can see why those boys thought that. With your blonde hair and green eyes, the two of you could be twins, not identical, but still." holding back the groan, no man wanted to be compared to a pretty teenage girl like that and god he hoped he didn't mention the twin thing to anyone else, the last thing he needed was that to get in Candi's head.

When they arrived back at his apartment complex Bailey gave Derrick another hug and a kiss to the cheek as he did before. "Thank you again Mr. Connors, I like can't wait to be able to drive myself." smiling back at the girl thinking she was talking about when she could get her license he replied. "Think nothing of it, you will be driving before you know it. I'm not so old I don't remember how excited I was when I got my own license, though from what I understand you don't have a permit yet, because of bad grades. You going to turn that around next year?" Bailey had no idea what he was talking about, Mandy must have made something up for his background. "Like fer sure, I like to my best but you know how it is." he said letting out a giggle hoping he sold the act. Keeping Candi convinced was difficult, but keeping Derrick Connors convinced was the real goal and only reason any of this needed to happen. "Good glad to hear it, Candace struggles with school too. Maybe you two could setup study time together online, two heads are better than one." giving his best fake smile he climbed out of the car. "Sounds like a good idea, thanks gain." he wanted to slam the door shut in frustration, but was able to contain himself.

Walking up the steps in the blue heels in the silence of the sinking sun he reminded of all the odd feelings. The movement of the breasts attached to his chest, the cool breeze at the end of the day on his exposed legs , the movement of the pigtails and the large hoop earrings. He was just glad the day was over and as he got to the door he remembered once again didn't have any keys. With a sight he knocked on the door to be let into his own house.

When the door opened, he saw Megan with a large smile welcoming him home. "Welcome home Bailey, your mom said she had to work just a little late, but would make it home before too long and we should eat without her. Though after seeing your video on your diet and seeing the boxes that arrived for you." she said motioning to the empty boxes by the front door. "Don't worry, I put them away in the fridge for you and let Amanda know how dedicated you are to getting into shape." Glaring at her he didn't say a word after what happened last time. "Don't worry, I'm not staying I just wanted to make sure you could get in, Amanda mentioned how you lost your keys. So, I went and had this made for you." she held out a pink metal key on a flower keychain. Snatching the key from her he squeezed in his palm or at least went to when he stabbed himself with his long nails.

"One last thing before I go diary, I got an email late last night about someone being naughty and trying to go to places they shouldn't on their laptop, not once but twice. You know those sites aren't for someone of your age.. If you need some release feel free to watch the videos I gave you. So, you have two options for being punished. You will hate them both. Number one is you pull up your skirt and get thirty spankings right now and another thirty later." the idea of being hit thirty times was to much, let alone another time. "That is way too much... all I did was try to go to some sites that I go to all the time!" waving her finger in front of the feminized man she stopped him. "No, my lovely niece, Amanda's ex-boyfriend went to those sites. You do not, and I told warned you about blocking them and still you tried to defy me, that is why you are getting so much." he wanted to yell he wanted to punch the bitch of a woman, but most of all he didn't want to be spanked like a child thirty times. "What is option two?"

"I'm so glad you asked. Option two is when Amanda comes home, you tell her how you were bad today, I don't care what story you spin. But you will tell her how your dad used to spank you to make sure you behaved correctly and it always kept you on the right path and how you want her to spank you now say ten times, then after you will thank her for helping you." Bailey's mouth dropped open, on one hand he would get hit sixty times and knowing this woman she would come up with a reason to make that number go up or ask his girlfriend to do it. "I will ask Mandy.." Megan raised an eyebrow. "I will ask mommy to spank me for being bad today." Megan smile and stood up giving Bailey a light hug. "Good, love you dear. You be a good girl and go grab your diary and sit on the couch next to me, I can't wait to read about yesterday and today."

Sitting on the couch with his legs crossed at the knee, still wearing his heels because Megan gave him a tut tut sound when he tried to take them off, Bailey sat next to her writing in with a purple pen about how today went from the perspective of a teenage girl. He wasn't even halfway done when they both heard a knock at the door. "Stay here pumpkin, I will see who it is."

Opening the door Megan saw Bailey's best friend and drinking buddy standing before her. The same man he was planning on running off to Vegas with to spend the money he was hiding from Amanda. "Well, hello there Charles. What can we do for you?"

"Megan, always a pleasure to see a beautiful woman like yourself, I was wondering if Bailey was in. Afraid he hasn't been returning any of my calls or texts these last few days. Said the five-foot eleven man with dark well-groomed short hair and beard. "Charles, I haven't seen your lowlife of a friend in days either and all of his clothes are gone, but Bailey is here. Just not the one you are referring too." The man before her gave Megan a perplexed look and looked behind her to see a scared looking blonde girl writing in a pink book dressed up like she was going out on a date. "You look confused Charles, come inside." she said motioning him in.

Bailey's panic meter was dialed up to eleven on a ten-point scale, his best friend Chuck was here saying he had been trying to get a hold of him, but he hadn't seen any missed calls or texts and yet Megan that bitch was inviting him inside the apartment. "I'm guessing your shit of a friend didn't tell you Amanda had a daughter with the same name as him. Well, here she is this is Bailey Ann, she is eighteen. Bailey this is Charles, he was a friend to your mom's Ex-boyfriend. For his part Charles only laughed at Megan's statement. "It is a pleasure to meet you Bailey, you are a pretty one just like your mom and aunt here." Megan was all smiles seeing him squirm and how even his best friend didn't see him for who he really was. "Well dear, don't be rude, say hi."

Remembering rule one and trying not to get caught he smiled sheepishly looking at his friend then to the ground wishing it would swallow him up right now. "Hello sir, thank you for the compliment." nodding and smiling at the demure girl Charles looked back to Megan. "Megan I know you and Bailey were never a fan of one another, but I think the two of us got off on the wrong foot." He said holding out his hand to the older woman. "I do go by Chuck to everyone, but if I'm honest I like the way you call me Charles. I was hoping that maybe I could give you my number and you could give me a call if you see my friend or if you ever wanted to get a drink." the twenty-eight-year-old man hitting on her was not something Megan expected or Bailey for that matter. She took his hand lightly and he shook it lightly before bringing it to his lips and kissing the back of it. "I hope that is a yes."

Megan blushed, Bailey was surprised to see the forty-year-old being hit on and accepting it from his own best friend. The two of them kept talking for a while and the sight of it was just making Bailey more and more angry. He had nowhere to go, he was sure if he got up and left drawing more attention to himself Megan would punish him for it, or worse something he did would remind Chuck of who he really is. Instead, Bailey just looked down to his diary and focused on his writing. "Oh, that would be lovely. Bailey dear did you hear that. Charles here has a younger brother that is who your mom's ex sold his old bike to and he thinks the two of you would just hit it off." Bailey's purple pen stopped as he looked up in fear and disbelief. "Look at her being shy, don't worry dear Auntie Megan will set it all up for you, he is twenty-two, and I know how you like to date people older. Though..." she trailed off looking at Charles. "I can see why Amanda dated someone younger for so long."

When Charles left, he was told how Bailey was recently given her own phone, the one that once belonged to Amanda's ex once he was out of the picture the phone was on her family plan so he wasn't going to take it with him. While Bailey saw in the phone how his old friends' number was blocked and notifications for it were turned off. Instead of yelling and freaking out at the idea of Megan trying to setup him up on a date with a kid who looked up to him he focused on his writing. He was so focused that he never even noticed Megan leave. What brought him out of his focus was the door opening and Mandy saying "Good evening honey, sorry I had to work late." This day was to much and he got up and minced as fast as he could in his heels to hug his girlfriend a few tears in his eyes. "Today, was like so hard... please just hold me." with one arm pinned by the hug Amanda put down her bag and hugged Bailey back. "Tell me about your day sweetie, I heard you made a plan for your diet with some smoothies, I am proud of you for doing that instead of just winging it. Now come on, let usgo sit on the couch and you can tell me about your day."

Opening up and telling Mandy about his day he had just finished telling her about how he had to babysit and how little Mikey didn't want to let go of him when he remembered the whiskey he drank and Megan's punishment. "Umm.. Mommy I need to ask for your help. You like said you would help me stay in character and it is like super hard. This is not something that I like.. Would do. But today I messed up and almost got caught." Amanda put her hand on Bailey to show support. "I umm drank someone Derr.. Mr. Connors whiskey and Candi almost caught me. I just needed something to help take the edge off and it was right there."

"Of course I will help you, what can I do to help you stay in character Bailey?" looking down at the floor before grimacing. "Well like my mom and dad used to spank me when I got out of line and it always put me back on the right path. The thought of getting another spanking tended to keep me from making the same mistake. Could you umm.. Give me ten spankings for drinking when I'm not supposed to be old enough to?" Amanda took a deep breath, it was request she was not expecting. Her own parents did it to her or she got the wooden spoon. "Sure honey.. Why don't you lay across my lap."

Hiking up his skirt and exposing his pantied bottom Bailey already read in the face lay across his girlfriend's lap ready to be punished because of that bitch Megan. When the first strike came down Amanda flashed back to one evening in the bedroom with Bailey. He had always been the controlling type and doubly so in the bedroom, and she went with it for the most part. She was the boss or a boss at work and had to make the decisions, sometime it was nice to be the one not having to come up with everything and be the submissive one for a chance. That night her hands were bound in a leather set of cuffs that were chained to the headboard with her legs spread apart by a bar attached to her ankles. She had her hair up and the only clothes was an over bust corset with garter belt attached to sheer black stockings and tall six-inch heels. She was on her knees on the bed ass in the air as Bailey spanked her.

"Tell me you have been a bad girl.." Bailey whispered to her.

"I have been sooo bad, I need to be punished." she replied playing along with the bedroom game. A hard slap came to her ass before he continued. "Tell me you are my little slut and you want me to punish you." he said slapping her ass again. "This slut needs to be punished, spank me!" she called out before a few more slaps came down. "That's right you do need to be punished, but we can't have the other neighbor complaining about how loud you are my little slut." he said putting a red ball gag into her mouth and latching it behind her head. Amanda remembered being spanked again and again, and while she wanted the game to end the gag kept her from saying so, all she could do was make noises. "AHMMJMM" she would try to call out for him to stop, but he only replied with "OH you like that don't you." before giving another swat. She wasn't' sure how many times he spanked her before he turned her over to start to fuck her hard. The game should have been over, sure they were going to have sex but the spanking wasn't supposed to go on that long and has he drove is cock in her over and over again she was lost in a world of both pleasure and pain and the feeling of being helpless.

The two of them had done some bondage after that night, but never again did she agree to the ball gag.

Smack, she laid her hand down hard on Bailey's back side for the eleventh time. "Now that was one extra for you to remember this lesson missy. You are just lucky I do not ground you for what you did. For now though you will apologize to me for misbehaving, drink one of your smoothies and go get ready for bed. I will be along shortly to brush out your hair."

Holding back some tears Bailey nodded and looked down at his phone seeing a text from Candi. The time on the screen said Seven thirty-five. "It's like still early though, I was hoping to spend more time with you." Amanda stood up and fixed her skirt. "When teenage girls get in trouble they go to bed early, now go get your smooth and march on to your room missy." the words were firm and commanding, like how he was sure Mandy spoke to her employees when they did something wrong, a way she had never spoken to him before, though his own words she was now trying to make sure he played his part as her daughter, all because Megan couldn't keep her nose in her own business.