Chapter 24

“Sweetie, it’s time to wake up.”

“Just five more minutes’ sis,” I muttered as I tried to bury my face in the pillow.

I snapped awake as I realized that wasn’t Hope’s voice. I jumped up, hit my head against something soft, and saw Scarlett falling back into the other seat as I remembered I was on the plane. “Oh my god, I’m so sorry Scarlett! Are you okay?”

“Well your head hit my breast and knocked me off balance, but they’re soft enough that I doubt we did any damage,” she said with a grin. “Not exactly how I pictured your head and my breasts making contact though.”

“I can imagine,” I giggled. “We’ll have to try that again some time, and hopefully get it right. I’m still sorry though. Hope always had to wake me up in the mornings, and hearing someone else’s voice made me panic for a second. What time is it?”

“Well it’s almost eight o’clock here. You were asleep for almost five hours. It took longer than usual to get the flight plans filed, so I let you sleep,” she told me. “We need to change planes for the trip to Dallas though. They already have the bags moved over and are waiting for us.”

I smiled as I looked her over. “You might want to put some clothes on first. You look amazing naked, but aren’t you worried someone might see you?”

“Of course not, we’re in our private hanger. Dale won’t open the doors until you and I are on the other plane. The only people here are the flight crew, and they’re all very familiar with my body,” she said as she winked at me. “Four of them got even more familiar with it on the flight over. Come on, let’s go. We still have a nine hour flight ahead of us.”

I followed Scarlett to the door and found Dale waiting. As he helped us down the steps, I leaned over and kissed his cheek. “Thank you for getting us here in one piece, and for being so nice on my first flight.”

He grinned as he led me to the other plane. “I could say I was just doing my job, but the truth is I love to fly. As for helping out pretty young girls, that’s a pleasure in itself. If you are still tired, most of the seats lay back and are comfortable enough to sleep in. However, if you can stay awake until we hit cruising altitude, the couches you were using on the first flight fold out into beds. You just have to stay awake long enough to take your seat belt off before you lay down. I usually sleep there myself, but ladies always get first choice.”

I eyed him slyly before replying. “I’m fairly awake at the moment but I’m still tired, can I let you know once we are in the air?”

He nodded as he helps me up the steps, “Of course, for now just pick any seat and we can get underway.”

Scarlett was already in the rear seat so I went to sit next to her. Peter came back to check our seat belts and make sure we were ready to depart. “Ryan and Daniel will be the pilots for the first part of the flight. The rest of us will be up front if you need anything. When you decide where you would like to sleep, just let Dale or I know. We will sleep where ever is left.”

I nodded as he turned to head back up front and I saw Dale sealing the door. “Scarlett, can I ask your opinion on something and not have you be grossed out by it?”

“Faith, I just had sex with four men, and each of them came in my mouth and pussy. I have licked Master’s cock clean after he has cum in me, and most of his other pets. You, Hope and Dawn are the only pets of Masters that I haven’t eaten his cum out of,” she said with a smile. “I doubt there is anything you could ask me that would gross me out.”

I took a deep breath and hesitantly asked, “Do you think Dale would like to sleep with me on one of the couches? I know he is like four times my age, but he’s handsome, and was so nice to us on the first trip. He kept coming back to see if we were okay, or needed anything. I’m still really tired, but I kind of wanted to play a little and snuggle with him.”

Scarlett looked at me and shook her head. “I know what you’re thinking. Why would he want to sleep with me when he could be having sex with Scarlett? Let me tell you a little secret, any of them would rather have you ask them to play. They have all had me many times before and they know I enjoy playing with them. You’re just as beautiful in your own way and you’re new to them. I’m sure Dale would be delighted and honored if you asked him to sleep with you, even if you only wanted to cuddle. I haven’t even had a chance to cuddle with you yet, and I know I would love to.”

“I would love that too, but I want to have a lot more energy when I spend the night in bed with you,” I told her as I licked my lips. “Would you be willing to take a rain check for the second night after we get back? I know my ass is going to be very sore the first night back, between Master taking my anal virginity and my punishment. I would love to spend the next night with you.”

“I’ll consider it a date. Any night one of us is not with Master you are welcome to join us,” she told me. “The same applies to the other pets, if you would like to spend the night with someone, just ask. I can speak for all the pets when I say we want to get to know you better. You, your sister and Dawn are just as new to us as you are to the boys.”

We sat and talked about the other pets for a while, as I still knew almost nothing about most of them. Scarlett was happy to indulge my curiosity and I learned a lot about the others. Eventually Dale walked back to check on us.

“You’re free to take your seat belts off and move about if you like. Faith, everyone else ate during our layover, but we got something for you as well if you are hungry.” My stomach growled at the mention of food and Dale laughed. “I’ll go get your dinner.”

Scarlett turned to me after he walked away and said, “Ask him when he gets back.” I nodded that I would and she smiled slyly. “I think I’ll invite Peter to join me on the other couch, he’s off duty for this trip and will need to sleep too.”

Dale walked back with a tray and I braced myself as he set it down on the table in front of me. “Dale, would you like to join me on the couch? I don’t know how much energy I’ll have to play, but I would like to cuddle and sleep with you at least.”

The smile he got answered my question before he responded. “I would love to darlin, even if all you want to do is cuddle and sleep I would be delighted. Just let me know when you’re ready for bed. I need to get the blankets and pillows out and get them set up. Scarlett, will you be taking the other couch?” After she nodded, he went to the back of the plane to set up the beds.

As I started eating, Scarlett turned and said, “I told you he would want to. Just remember, he has no expectations. If all you want to do is sleep, he really is fine with that.”

I nodded as I continued eating. “I know I shouldn’t be so self-conscious. Half the boys I went to school with were asking me for dates. I guess it’s just being around all the pets these past few days has made my shy side come out. I feel like I don’t measure up,” I said, pushing my chest out.

“Don’t worry, they’ll grow,” Scarlett chuckles. “I know I am a bit over endowed up there, but do you see any of the other pets looking like they feel inadequate next to me? You’re only fifteen and a C-cup. I know you’ll catch up with most of Master’s pets in the next year or so.”

“I’m only a B-cup,” I told her self-consciously.

“Pfft, I saw the bra you’re wearing, and you’re about to burst out of the top of it. You are only wearing a B-cup still because your mother didn’t want to take you shopping,” she replied with disdain. “Thankfully Master wants you to look more presentable when we meet your mother. After we call her and arrange our meeting, Dale will be taking us to North Park. He told me to take you to shopping, so Nieman Marcus and possibly a side trip to Victoria’s Secret so we can get you proper underwear.”

I looked at her in shock. “You don’t need to do that. I’m sure we can find something presentable at Target. That was where mom got all of our clothes.”

“You remember that punishment you just received,” she asked me. I winced and nodded. My ass was still sore from my punishment, how could I have forgotten it? “That is about half of what Master would do to my ass if I brought you back in rags from Target. You are one of Master’s pets now, and we have an image to maintain. You can pick from Neiman Marcus or one of the designer shops in the mall. Master already spent a few million dollars on you; a few hundred on an outfit is nothing.”

“I would feel bad getting something that fancy without Hope though.” As far as mom was concerned, the height of fashion for us had been Target. She would get herself nice clothes, but her kids all got Target or Goodwill. “Mom never got us anything that nice.”

“I don’t think you need to worry about Hope,” Scarlett said with a laugh. “Master gave me strict instructions to get two of whatever you picked. I think he enjoys having a matching pair of beautiful teenagers.”

I had finished eating, so I just sat and stared at her in shock. “You’ll get used to it after a while. Just wait until he takes us skiing. He’ll actually be in the shop when you’re picking out clothing. Samantha tried to be frugal and pick out clothing by what was least expensive when he first outfitted her. He bent her over the counter and spanked her bare ass while the shop clerk just watched with a big smile on his face. Then he sent her back to try again.”

“I’ll have to remember that when he takes us skiing,” I said with a yawn. “Sorry, I’m sleepier than I thought.”

“It is okay sweetie; you had a very long day. The bathroom is the last door at the back, go get ready for bed. I’ll let Dale know and have him meet you back at the couches,” she told me. “I’ll probably be bringing Peter back shortly as well; as we have a busy day ahead of us tomorrow.”

I nodded as I got up, and then gave Scarlett a quick kiss before heading back to the bathroom. I came out of the bathroom to find Dale sitting on the couch fully dressed, so I pulled my shirt off and asked him to undress. As I went to unsnap my bra, I looked down and figured maybe Scarlett was right. It did feel tight, and my breasts were about to spill out of the cups. I might be bigger than I thought.

I finished undressing and looked over at Dale again. He was only a couple inches taller than my 5’1’’ and stocky. He reminded me of a big teddy bear. A tear came to my eye as I remembered Mr. Snuffles was still at mom’s house and I wondered if she would let me take him with me when we left.

Dale was down to just his boxers when he noticed my tears. He quickly came over and hugged me. “Darlin, you don’t have to do this. I can go sleep up front if you are uncomfortable.”

I laughed through my tears as I squeezed him tight. “It’s not that, I do want you to be here. It is embarrassing and somewhat childish actually. I was thinking you looked kind of like a big teddy bear, and I started thinking about my teddy bear at home. I used to sleep with him every night, and he still sits on my bed. Like I said, it’s somewhat childish.”

“I don’t think so darlin,” he said as he wiped away my tears. “We all keep mementos of our childhood around as we grow up. I still have the blanket one of the retired ponies made me over fifty years ago. It is just an old knit blanket now and she made one for each of the children as a birthday present when we turned four, but she did it out of love. I still have it on my bed to remind me of her.”

“Even Master keeps a memento of his childhood in his cabin if you can believe that,” he told me with a grin. “His father had gotten him a little stuffed dog on one of his trips, and Master carried that dog around for years. Last time I was at his cabin the little stuffed dog was sitting on top of his bookshelf.”

“I was in his cabin yesterday, and it’s still there. I was curious because it seemed out of place, but I didn’t want to ask,” I admitted with another yawn. My hand slipped between our bodies and grasped his cock through his boxers. “I’m getting pretty tired, but I would like to play some before we go to sleep. Would you like to take these off and lie back on the couch?”

“I would be delighted to, but I may disappoint you,” he admitted as he took off his boxers and laid down. “I haven’t been with a woman in a while and I may end up cumming fairly quickly.”

“That is okay, I asked you because you have been so nice to me, and I wanted to give you something special as a thank you. I enjoyed doing this with Master, and Scarlett told me I would need to practice to build up my stamina. You just need to lay back and enjoy,” I told him as I reached out and grasped his cock.

He was not as big as Master, but at just over seven inches it was still impressive. I wrapped my fingers around his cock and gently stroked it as I got down on my knees next to the couch. Remembering Scarlett’s lessons, I reached down between my legs with my free hand and began rubbing my pussy. Sliding my hand down to the base of his shaft, I leaned in and licked all the way up his cock. After running my tongue around the head a couple of times, I placed a kiss right on the tip before licking back down.

His quiet moans of pleasure told me he was enjoying himself as I licked back up and around the head again. Once the head of his cock was thoroughly wet, I opened my mouth and slowly slid my lips down around it. This wasn’t as challenging as it was with Master, but Dale’s loud moan as he entered my mouth was still rewarding.

I slowly slid my lips further down, and got a little more than half of his cock in my mouth before I started to gag and pulled back. My fingers were soaking wet and I moved them up to play with my clit as I started bobbing over the top half of his cock. After couple minutes of steady bobbing, I decided to experiment. I started stopping with just the head in my mouth and running my tongue around it before going back down.

His loud moan showed clear approval so I continued, changing up with a few fast bobs between licks or stopping to run my tongue around the head of his cock multiple times. I felt him touch my shoulder and say, “I am about to cum darlin, if you want to pull off so I don’t cum in your mouth.” I did not want him to cum in my mouth, but probably not for the reason he thought.

I quickly stood up, keeping my hold on his cock as I swung my leg over his hips. I lined his cock up and sank it deep into my pussy right as he started to cum. A few more strokes on my clit was all I needed to send myself over the edge as well. I leaned forward and kissed him as we rode out our climaxes.

After our climaxes ended, I pulled off and slid down a bit to lay my head on his chest as I heard another moan of pleasure. I looked over to see Scarlett riding Peter, and from the look on his face, he was in the middle of his own orgasm. She glanced over, saw me looking, and winked. “Sleep well sweetie.” I closed my eyes as I snuggled into Dale’s chest and drifted off to sleep.

“Ouch!”

I pulled my hand back and glared at Dale for laughing at me. We were in Neiman Marcus, but I was having a hard time picking something out. It wasn’t that I was having a hard time finding something I liked. There were dozens of outfits I liked, but every time I reached for the tag Scarlett slapped my hand and told me to pick what I wanted.

It was my own fault in a way. I’d seen this cute little dress right after we walked in that would have been perfect, but it was almost six hundred dollars so I quickly moved past it. Scarlett had seen me look at the price tag though, and was making sure I wouldn’t consider prices when I made my selection. Unfortunately the thought of how much they might cost was making me hesitate. I finally settled on one that didn’t look too expensive and gave Scarlett a hesitant look as I reached for the hanger.

“Oh god no sweetie, you don’t want THAT one. It’s totally not you.” I glanced back and saw one of the attendants watching me with an annoyed look on his face. “That color would dull your gorgeous complexion and you don’t want to look like you’re going to a funeral.”

“He’s right you know, flat black really doesn’t suit you,” Scarlett added. “Maybe you can help us though. As you can see, her mother dressed her and her twin sister like they were paupers, so she’s really out of her element here. We’ll get a proper wardrobe once we get home, but we needed something so she doesn’t look like a refugee from the bargain bin today. Could you recommend something suitable that will travel well, we’re flying out tonight.”

“Of course, I rarely get to outfit such a delectable little peach. Any price range you’re aiming for, and you said twins?”

“Identical, and prices are irrelevant as long as you have a pair of whatever you find for her, just pull the tags so she won’t have to think about prices. I’m thinking sundress, heeled sandals, and depending on your selection, undergarments,” Scarlett replied. “There’s a Victoria’s Secret down the hall if we can’t find something enticing here.”

He looked me over with a critical eye for a moment then smiled. “So vixen wrapped in a vernier of innocence, my husband is going to be SO jealous when I tell him about this one. I usually get older women trying to hide their figure with the clothes, so you’re a treat. Let’s see, we want summer but not too light. I have just the thing. Fitting rooms are at the back, take her into number one and strip those rags off her. I’ll meet you there in a minute.”

I sighed as he vanished between the racks. “He seems confident he knows my sizes.”

Scarlett chuckled as she took my arm and started steering me toward the dressing rooms. “He’s a gay man working in the clothing department at Neiman Marcus, he could probably guess your measurements to within half an inch. You’ll feel like a whole new woman by the time we leave.”

The fitting room seemed enormous, even when Scarlett followed me in and started pulling my clothes off. “I don’t think he meant that literally.” Her eyes were sparkling with laughter but she didn’t stop until I was completely naked. We only waited a couple minutes before there was a knock on the door and she called out for whoever it was to enter.

I gaped in surprise and barely had time to try covering myself before her and the attendant started laughing. “I’ve seen it all before, sweetness. I’ll admit if anyone could convince me to play for the other team it would be the two of you, but alas, I just don’t swing that way. Let’s start with the basics, if this meets your approval?”

He’d put down the pile of clothing and was holding up a semi transparent red lace demi-cup bra with matching thong. They were gorgeous and probably cost more than my entire school wardrobe from last year. Scarlett said they were perfect and he held the bra out like he was planning to dress me. When I sighed and uncovered myself to take it he laughed.

“You’re such a delicious little doll,” he said as he stepped back and watched me dress. “That will work for her even as she darkens to that gorgeous tan, just remind her to wear sunscreen. The tropical sun will destroy her complexion if you’re not careful.”

I looked up in surprise as I stepped into the thong. “How do you know we live in the tropics?”

He smirked as he held up the dress. “The same way I knew there wouldn’t be an issue when I walked in. Scarlett and Dale are in here every few months outfitting the pilots. I knew she wanted to have a little fun with you because she did the same thing when they brought Peter in the first time.”

I shook my head as I stepped into the dress smoothed it down my body before turning so he could zip it up. “That’s about as close as you get for off the rack. We could go a size smaller, but it would be too tight to pull off an innocent look. Did you want stockings? I grabbed knee-high and full length, but she doesn’t really need them with these sandals.”

I knew he wasn’t asking my opinion so I glanced over at Scarlett, who shook her head. “She certainly doesn’t need them to hide any imperfections, so I think we’ll go without.”

He nodded and helped me into the sandals before stepping back and looking me over again. “She looks delish, but we could accessorize a bit. Maybe a hairband or some barrettes so she doesn’t have to keep pushing her hair back?”

“I think that’s just nerves because the outfit she’s wearing probably cost more than her mother spent buying clothes for her in the past two years.” Scarlet reached over and pushed my hair over my ears. “A hairband would be a good idea, but nothing too extravagant. We don’t want anything to draw attention away from those sparkling eyes. You did have a matching outfit for her sister?”

“I just need to collect everything now that we’re sure on the sizes. Will that be on the regular account and will there be anything else today?”

“Dale will sign for it, and could you bag those up?”

“Of course, and I’ll grab those hairbands while I get the second outfit. It’s been a pleasure as always.”

He grabbed my old clothes and slipped out the door as I shot an accusing look at Scarlett. “You set me up. I’ll admit my reaction probably looked hilarious when you think about what we wear on the island, but I almost wet myself when he walked in.”

“You were so wrapped up in how much this would cost that I figured we needed a little surprise to loosen you up a bit. I’m just glad Fred was working today, as he’s the only one here with a sense of humor. Come on, I’ll buy you a cinnamon roll as an apology.”

I shook my head and laughed. “You don’t need to apologize, but I won’t turn down a cinnamon roll. Isn’t that way outside our diet though?”

“Most definitely, but a little indulgence never hurt anyone. We’ll just have to find a way to work off the extra calories.” She had a thoughtful look on her face as she rubbed her chin. “I wonder what we could possibly do to burn a few hundred calories?”