Babysitting and showtime

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 lip sad 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 setup on a tri-pod. “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 [email protected] 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 **** 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.