Chapter 10

I wasn’t going to stand in the way of my sister’s happiness. The offer seemed genuine and well-timed.

“I am sorry, Sir, but I’ve already committed to being trained with my sister down in Florida. I don’t know how long we’ll be here, but I’d love to fuck you again before we leave,” Kim said.

The gentleman seemed perplexed that we wouldn’t accept his generous offer. He made the case that he had a reputable law firm and the means to support all of us. “You won’t have to work or fuck other men for money,” he said.

“Then I would get fat, lazy and selfish, Sir” Kim smiled at him politely. We were both naked. She played with his cock after he came while she answered him. He started to get hard again, and she began to lick his dick.

“Okay, if you like to fuck I know a porn theatre around here. We can become swingers. I’ll let you bang anyone you want,” he said.

“That is such a generous offer, Sir, but I am not interested,” Kim politely declined him. The gentlemen seemed disappointed, but he didn’t get angry. He collected his things and laid down a generous tip. Kim begged him not to do that but he insisted we take the extra hundred dollars. “You are the most interesting and certainly the strangest prostitutes I’ve ever met. I wish you well,” he said as he left.

“Why didn’t you take his offer?” I asked Kim. I found it hard to believe she wouldn’t even give it a try.

“If it sounds too good to be true, it probably is.” Kim shrugged her refusal off like it was not a big deal and offers like that come around every day.

I told her that it would have meant she didn’t have to do the same things that I did. She asked me why I didn’t go for it then either.

I told her that I had already made my choice and I was going to stick with it. I’d had a lot longer to give thought to what I had chosen to do.

“You’ve only been doing this a day longer than me, Ma’am,” Kim observed with a sassy smile. That was technically true. The BDSM sessions I’d done with men I’d met on Craigslist, were amateur-hour compared with what I was doing now. I still felt like my sister and I were worlds apart in experience and she had wasted a good opportunity.

Kim didn’t want to explain any further and the man was already gone anyway.

“Please don’t tell Master or Jessie that he made me the offer, Ma’am,” Kim begged. She explained that she didn’t want Jessie to think that they could have this fabulous life with a sugar daddy and she had refused. She said she wanted to see where things went in Florida with Mike.

I reminded her that she would have to call her son, Mister Jessie, from now on. Kim apologized and acknowledged that she would do that from now on. “You wouldn’t have to do that with this guy. He left his card,” I showed it to her.

Kim took his business card from my hand and threw it in the trash. There was something that felt symbolic about her tossing away the chance she could call him if she changed her mind by tomorrow.

After that I believed my sister was committed to Florida and was all-in. There was no further point asking her if she was sure about what she was doing. She did text Master to let him know a guy had left a generous tip of an extra hundred dollars.

He told us to find a homeless guy and offer to fuck him for free. That would cover the earnings. We found a gross guy living behind the motel and offered to give him a shower before we fucked him. He loved it when we washed him down. Kim loved the size of his dick. His balls hung down like two miniature bowling balls. They would have made a donkey proud!

We had made more than three hundred dollars by the time Mike returned from the mall with our kids. I was surprised that Kim made about sixty bucks more than me. She really earned it too, doing mostly hand-jobs and blow-jobs.

Master took us into his room after he returned and began to inspect us. “I spoke to my wife. Wendy said that the two of you would be a lot to handle and she wasn’t sure she wanted to have to deal with that,” he said.

My sister looked disappointed. I wondered if she already regretted not taking that sugar daddy’s generous offer now.

“I had to remind her of all the stray dogs she’d brought home over the years and said that your sister was a stray dog who followed me home,” Mike explained. Wendy agreed to let us move in but she wasn’t happy about it.

“I’m going to build a kennel in the backyard for you both. You will be out there a lot when you are not in use. I am talking rain or shine and it rains AND shines a LOT in Florida. It is going to be hot, muggy and rainy!” Mike assured us.

Kim didn’t wince when Mike pushed a butt plug up her ass. It was the same as mine, only slightly bigger. It was part of a set. It slid right up my sister’s ass and she giggled then wiggled her ass.

“Jessie, Emily and I had a long discussion at the mall,” Mike said. Emily and Jessie bought some things. Emily even had a swimsuit.

The last swimsuit she had never touched water. I don’t think Emily actually ever wore it. We were at Wal-Mart about two years ago with my mom. There was a skimpy polka dot thong in the Junior Miss section. The caption above the merchandise read, “She wore an Itty Bitty Polka Dot Bikini.” This thing was skimpy by any standard. It wasn’t a G-string thong, but it showed off a lot of skin! It certainly dumbfounded my mother that a swimsuit like that was being marketed to teenagers.

Wal-Mart is kind of the poor man’s titty bar. Women without panties or in just a tank top were pretty common. We’d see an entire family of Hispanic women from the grandma to the youngest of them get out of a car all wearing sequined mini-skirts. We called them “Mira Mira” girls because they were continually trying to get attention and show off. It wasn’t entirely surprising to me to find a bikini that small, considering who frequently shopped there.

Emily wanted to get a rise out of my mother, and she asked for it. My mom thought it was absolutely disgusting and inappropriate. I thought the goof was funny so I asked for a matching one and grabbed the largest size they had. My mom bought us both the swimsuits, but we never actually wore them. We just wanted to see if we could get my mom to buy them.

This time Emily had chosen a much less revealing one-piece French bikini. It would definitely be considered conservative by today’s standards on Florida’s beaches. I wondered if Emily was seriously considering actually wearing it and hitting the beach with us. I already knew I would be paraded on beaches. I hadn’t for a minute thought Emily would want to go too. Jessie found some classic Sun Britches like they used to sell in the 1980s and a pair of Kevin Costner style Ray-Ban sunglasses. He thought he would be hot shit in those.

“Jessie has agreed to become my helper. He is going to make sure that you eat on time, shit on time, go to bed on time and behave yourselves. He will have limited authority over you when I am not around. I’ll go over that with you as we travel back home. I was planning to take the scenic route for and do some sight-seeing for the next two weeks. You two whores will work your asses off every night when we stop someplace and you’ll be cuffed or caged in the RV while we’re doing fun activities,” Mike explained.

He said the job would help teach Jessie responsibility. It would also help Master and his wife by having someone handle some of the day to day things that always needed to be done. “I work, and my wife works. We can’t watch you 24/7. Over the Summer, Jessie can help supervise you while we’re at work.”

He asked Kim if she was okay with that.

“I guess, Sir,” Kim answered dumbly.

“You guess, or you know you are okay with it?” Mike whipped her tits with a leather crop. My sister spasmed slightly and quickly told him she was okay with it as long as Jessie was willing.

He said that Jessie would get a larger allowance in exchange for helping keep track of us and managing the day-to-day details. He said he was going to give us all an orientation shortly. He reminded Kim that she could change her mind after she understood just what he expected. He also told Jessie that if he didn’t think he could handle it or would get intimidated or manipulated by us, that he could change his mind now, too.

“I am not going to make you do anything you are uncomfortable doing, Jessie. You can always change your mind at any time If you do though, just understand I won’t take it lightly and I am not likely to make you the offer again. I don’t want to play a game of back and forth. You will you or won’t you,” he promised.

He also told Jessie that the position involved trust and Jessie had to earn that from him. “I’m not going to give you the keys to the kingdom. You will be evaluated just like your aunt and mother are evaluated. I will help you understand your role. If you ever get in over your head the worst thing you could do is not tell me or ask questions,” he explained.

Jessie nodded enthusiastically. Master said that went for ALL of us. I wasn’t sure if he meant Emily as well but I thought it might.

Mike focused on Kim. “I will give you a chance to back out tomorrow before you tell your mother and brother where you are going and what you are going to do. If you agree, you belong to me for two weeks. There will be no quitting just because things get hard or boring. Once we get to my house and meet Wendy and my son, you will have another opportunity to quit. We’ll have a meeting and discuss your reasons. If you agree, I am going to hold you to serve me for 30 days. I’ll test you, and we’ll have another meeting. If you agree to continue, I will do that every 30 days until we get to the 90-day mark. If you ask me to give you a final exam and you pass, then I am going to collar you for two years. You will belong to me for that time. There will be no quitting. There will be no angry rants and petty little bickering. Your ass WILL be mine for two years. Joy’s deal is different in that she’ll belong to me forever.”

Kim nodded that she understood, but it was a lot to take in. Emily jokingly imagined me at my mother’s age walking around naked in high heels and tied up behind a shed. “Nobody wants to see that. You sure you’re going to keep her as a slave FOREVER?” She laughed in disbelief.

Mike assured her that he meant forever. “She will live and die as a slave, and that is a choice only she can make. I already have an eternity collar for your mother. Once it’s locked on, it doesn’t come off. It’s just like marriage - until death do we part,” he said.

Emily joked that Kim had already been married and that didn’t work out so well. Mike told her quite seriously that he WAS going to make it work.

Emily had opted to basically have nothing to do with us but still get an allowance. She was just going to live in the Master’s house and go to school while my sister and I served.

“Emily will be able to tell you to fetch her things and to make simple requests. She does not want the added authority or responsibility Jessie does and I respect that. She’ll get a smaller allowance. I am not going to push any of this on her,” he insisted.

I didn’t doubt that my daughter liked the idea of getting paid for doing nothing. She grinned and confirmed it.

“Do I still have to call my niece Miss Emily?” Kim asked with a shy look at Emily. Emily didn’t care what she was called. She thought this was a silly game we were all playing anyway.

Mike smacked Kim’s bottom and told her to wait until she was spoken to, unless it was an emergency. “You will call all females Miss or Mrs and their first name or Ma’am,” Mike said. Kim looked at me and stuck her tongue out.

Kim was a little dense and had to have things explained to her a few times for her to finally get it. Mike clarified titles didn’t include me. “Your sister is just Joy to you. You are on a first-name basis because you are on the same footing. My wife will be Ma’am, Mrs. Wendy or Mistress at home,” he explained that in his absence, she was the boss.

“Is Jessie the boss in both of your absence?” Kim asked meekly.

“Pretty much. First, he needs to earn my trust and demonstrate that he can handle you. He isn’t a Master but you will call him Mister Jessie or Sir at all times. Think of me as the Principal, my wife as the Assistant Principal and Jessie as a Hall Monitor,” he said.

“What about your son, Eddie, Sir?” my sister asked.

Mike laughed and said that Eddie had about as much interest in his dad’s submissives as Emily did. “He was twelve when the last one stayed with us. He preferred to fly a kite with her or take a walk with her then do anything else back then,” he said.

Emily asked if Eddie was cute. Mike chuckled and told her that he looked just like him at that age. “So, not cute, then?” Emily asked sarcastically.

Mike roared with laughter. He thought that Emily was a clever girl and he wasn’t offended by her jokes. He turned his attention back to the orientation he planned for Jessie.

The first thing Mike did was line my sister and me up next to each other in the bang room. “Jessie is now allowed in the bang room. If you are fucking someone, I want you to lock the door. I want to clarify that with Jessie’s new responsibilities, he has a reason for being in here. I still don’t want him actually seeing you fuck or give head in here.”

He explained that there needed to be limits and boundaries. “I don’t want to overwhelm you, Jessie. You need to learn the foundations and basic principles of caring for and being responsible for a submissive. If you focus only on the sexual aspect of it you won’t really understand what I am teaching,” he said.

Jessie seemed a little disappointed.

Mike said that it didn’t mean that he couldn’t have fun at our expense and that he would still see us masturbate frequently. “You can give them a five-minute masturbation break when they behave themselves if they have nothing else to do,” Mike said. He told us that if we get the break, we better be amusing and start touching ourselves.

He told us to squat down and start and graded us on how much we touched our tits and clits. “You can also punish them if they roll their eyes, talk back, answer your orders slowly or generally need a quick correction,” Mike said. He reminded us that Jessie could spank our butts while we were in the inspection position. He also taught Jessie to spank us over his knee. My sister is mostly tits and ass, and she nearly squashed Jessie when she laid across his skinny knees so he could practice smacking her butt.

I began to realize that Jessie was definitely an ass man when he spanked me with his hand. He liked spanking me so that my ass flapped open, and his hand landed on my asshole. I was reminded of how I’d teased him while I did the laundry, and I felt guilty all over again. I suppose he was getting his jollies at my expense now and I resigned myself to it.

I knew it had to be harder for Kim to let her own son spank her butt. I don’t think she minded that much because Jessie still had a lot to learn about how to really deliver a powerful butt whooping that turns your ass from pink to red to blue and orange like Master could.

Mike told him that he would need to learn to inspect us. “You can inspect them anytime you like in private situations. You should ALWAYS spank them when they get back onto the motorhome, get ready to leave the house or come back home,” he said.

Jessie looked a little nervous about openly touching us intimately when Mike ordered us into the inspection position. I held my ass cheeks open and waited next to my sister.

“I can stick my finger into their butts?” Jessie asked. I almost giggled over how naïve and scared he sounded.

“Yeah, that is generally how inspections work. You should wriggle your finger around there to see if they have any money or other foreign objects hidden in their ass. You also want to make sure they don’t have a big old turd back there because I want their asses clean and empty while they work,” he said.

Jessie jammed his finger up my ass all the way to the hilt and I felt like he was trying to touch my eyeballs through my asshole. Emily teased him that he shouldn’t get a boner while he did his work. I knew she was secretly enjoying my humiliation, as well. I think she was eating up the fact her cousin was like a kid in a candy store with no idea where to begin. Jessie ignored Emily’s remark.

Mike told Jessie to make me clean his finger. I sucked it like a cock, initially to his first knuckle and then to the next. Mike told me I’d done a good job. I knew that but it still made me feel pleased to hear Master’s praise. Jessie was getting blue-balls and fighting the urge to adjust his erection because of how well I sucked his finger. I also felt good about teasing him. I knew I would wrestle with feelings of guilt about that too. It made me feel slightly powerful to at least decide if I was going to blow his finger like a tasty cock or just clean it with my tongue.

He WAS teasing me too, after all. He didn’t inspect me as much as he masturbated me when he put two fingers in my pussy. “How come Joy’s pussy has so many folds and wrinkles and my mom’s has that nice big flap in the front of hers?” he said as he compared our pussies.

He made my cunt sound ugly and wrinkled. My sister has a huge clit that looks like a tiny penis and when she gets horny it starts to protrude. Mike flicked her clit and explained that the hood covered her clit most of the time but that once she got excited it came out to play.

Jessie rubbed my tits, pulled my hair and even looked in my ears and mouth at Mike’s instruction. He was only reluctant to play with me at first. Once he had permission and I was compliant he wasn’t shy at all with me. I hated it because I was getting wet while my nephew learned about the female anatomy by exploring every nook and cranny on my body.