Chapter 18

Over the next few days, we drove around South Carolina and Master took in the sights. Each day, Master progressed our training and reinforced what we’d learned the day before. He also taught Jessie how to see through our attempts to manipulate him. We didn’t always know we were doing it, or do it intentionally. It just seemed natural to appeal to Jessie’s trusting nature and mess with his head a little. I am talking about appealing to his empathy for us so that he wouldn’t be such a stickler and slam our nipples or clit hoods between two book covers as often.

He absolutely loved stretching my nipples until they looked like pencil tip erasers and then slamming them inside a hardbound book as a form of correction throughout the day. Jessie was very diligent about watching over us. He didn’t tolerate any slouching or eye-rolling from us.

Every night we’d stop in a dive motel and work from sunset until around four in the morning. There was a dramatic lack of customers after that point in the night. We’d fuck or suck about fifteen guys each and on average, earn about thirty bucks a piece. Most guys didn’t question why we were selling pussy so cheaply. They were just happy to bang us without a condom.

Master rented two rooms. One room was the safe room. We’d show up there and drop off the money. We would spit out or squat over a dog dish and let the cum drip out of our ass or pussy. It would collect there all night, and eventually, Jessie would make us stir it with our finger and lick up every last drop of it.

We were both given a 36 ounce Styrofoam cup each night. Master put ice in it, and he or Jessie would piss in it. As the ice melted, it served as water. We weren’t allowed to drink anything else while we worked.

Master kept an eye on us while we were outside. He didn’t spend all his time watching, but he frequently checked up on us. He didn’t mind if we spent time talking to a customer. He wanted us to learn to be friendly and polite. It was the part I hated more than I did bending over and letting them plow me.

My sister and I even more frequently fucked guys together. They loved the fact that we were sisters. The fact we looked the same was good enough for most of them to believe it. We showed them our I.D.s if they doubted it. Master rented a second motel room he called the “bang room” for us to take men and fuck them. We also jumped into cars and even fucked behind alleys or in gas station bathrooms.

After we were finished for the night, we’d be tied up together titty to titty and lay flat on the ground. In the morning, Master would count the money and award us points. My sister isn’t very competitive so she really didn’t care about that, but she did like the fact she was in the lead. We didn’t sleep that much. Master let us take little cat naps but he didn’t want us being lazy. He was trying to push us to be better whores. The adrenalin rush we often got from the spankings and humiliations was helping carry us through.

“As an added incentive, I’ve decided that the girl with the least points will be the bottom bitch. The bottom bitch will only take it up the ass,” he said. Master held up a jeweled pussy clamp. “This is Wendy’s, so I hope for your sake you don’t lose it. She will be extremely angry if one of you does.”

It looks similar to a picture I found online only it is bedazzled with sharp fake diamonds, made of stainless steel and when closed, clamps a pussy shut. Men certainly didn’t want to try forcing their cocks into a cunt clamped like that no matter how small their dick might be.

https://cults3d.com/en/3d-model/naughties/pussy-clamp-wide-version

Master showed Jessie how to attach it to my pussy by catching my labia between two curved metal bars on either side. There was an additional clamp bar on the top and bottom that would get ratcheted tight to close my pussy so that I could barely slip a finger inside.

Master only had the one and since Chastity was in the points lead, he used it on me. He could completely open my pussy so that it was a stretched, gaping hole a cock could easily slide in and out of. He did that during the day while he drove the Winnebago. Of course I still had my butt plug in during the day too so I was intensely aware of my sex at all times and it was even more difficult for me to look Emily in the eye.

In the morning, we were given an early morning beating with a rod and an affirmation. We’d thank Mike and Jessie for another day of discipline and Mike would go over what he thought we did well and what we needed to work on. We’d usually shave each other’s bodies hairless below the neck and then be led outside to piss and shit. We’d typically get an enema when we go back inside and then ten minutes later, return outside and empty our asses again. This was repeated until the water ran clear and Master declared us ready for business.

We’d eat breakfast scraps out of a dog bowl after chewing up each other’s food and spitting it back into the bowl. It was pretty disgusting to say the least. Once we were finished, we kissed the mess off each other’s face and necks and washed up. Master did the cooking when he wasn’t stopping at a restaurant. He was an outstanding chef! He taught Jessie how to make some of his signature omelets.

Then it was inspection time. Chastity waited with barely concealed excitement. Jessie had been told he was to fist both her lower holes to be absolutely sure she hadn’t hidden anything inside her again. She wasn’t the least bit afraid of the thought of Jessie’s fist in either of her holes. Just thinking about it made me pale. Or rather, pale even more than my natural coloring. I had been clear with Master during our online chats that I’d never had a fist in my pussy and it was a hard limit for me. I’d assumed he fully appreciated that meant my asshole as well.

But there was a problem. I felt such guilt watching Chastity take Jessie’s fist in either hole without complaint that I heard myself ask for equal treatment, which caused a raised eyebrow on Master.

“You’ve changed your mind about that boundary? I had no doubts of Chastity’s ability and I understand what’s motivating you but the answer is no. I said I wasn’t going to physically injure you to the point of you needing medical attention. That’s not negotiable. You still have a living to earn so it’s no until you demonstrate your ability to take a whole fist the way Chastity just did.

“How can I demonstrate an ability if you won’t make me try, Master?” I asked. I was secretly pleased that Master wouldn’t let me try.

“I’ll let YOU try but I won’t allow Jessie to inspect you that way until you can demonstrate an ability to take a fist in each hole unassisted. Forcing a fist up your cunt or ass definitely has its attractions but it’s not directly benefiting you the way you displaying your own fist in each hole would. Show us you can take it and you’ll be allowed the same level of inspection Chastity gets.”

“Oh,” I replied. My newfound sense of fair play was at odds with my fears. I didn’t want Chastity subjected to something I wouldn’t or couldn’t do and we were in this together anyway, but the idea of demonstrating something I had no idea if I could actually do, in front of others no less, terrified me. “Can I have some time to practice alone, Sir?” I asked. It would be a far less humiliating demonstration to provide if I at least knew beforehand that o was capable of it.

“No privacy. That was the agreement. I would have had you taking my fist sooner or later anyway but I originally planned for that in the long term, not this early in our relationship.

Master made me wait in place while he went to a cabinet and rummaged in the back before pulling out a massive black butt plug that had a crown as big around, as his fist. He placed it on the floor in the RV’s most open space. “You can stretch your holes with this. Once you feel confident enough that you can get your own hand inside either hole, tell Jessie you’re ready. Jessie won’t do your inspection until after we’ve seen you fist yourself. You have half an hour to practice.”

Master dismissed me with a wave of his hand. I was wishing I’d kept my big mouth shut. The butt plug on the floor looked so intimidating. On top of that, I didn’t want to be seen as a failure if I couldn’t fist myself. I knew I was limber enough to do it, but suddenly my own small hands felt massive to me.

Then there was the matter of everyone being my audience, especially if I did fail. It wasn’t fair. Jessie COULD HAVE simply forced his fist into me the way Master had taught him even if I’d passed out in pain. Doing it by my own hand, pun intentional, was ten times worse in my mind.

I went to the plug and lubricated it by spitting all over it before lowering my mouth and opening as wide as I could. I was able to force about a third of its girth into my mouth. If it had been a real dick, there would have been tooth marks less than halfway down it.

In a half hour I’d managed half the plug in my asshole and slightly more in my cunt but that was by balancing myself so all my weight was pressing down and my feet were completely clear of the floor. I’d found that furiously rubbing my clit helped dilate me but nowhere near all the plug would go on either hole. The worst part was that I was so worked up I was edging myself like crazy!

“Time’s up, Joy,” Jessie said helpfully. He’d watched me intently the whole time, offering guidance as if he’d had experience. In a way I suppose he had. He’d fisted his mother’s cunt and ass already today.

Emily had been playing on her phone the whole time too. She’d called the whole exercise nasty but that hadn’t stopped her occasionally leaning down and snapping a few progress shots with her phone. I wondered if she was going to text them to my mother or worse, to Randy.

In a way, my demonstration was a little anticlimactic. It seems my own fists are considerably smaller than that shiny black plug. With hardly any effort I was able to fist my own cunt. It was harder to get my hand into my own ass and I was acutely aware of my audience when I succeeded in forcing my fist inside, but the degradation of the display was worse than I’d ever imagined it’d be if I’d had to have simply masturbated in front of my own mother. Luckily I didn’t have that humiliation to compare this to.

Feeling my nephew then do it proved to be just a little more humiliating because by then I could hardly control my need to cum. The feelings didn’t dissipate as quickly as Jessie’s inspection, either.

Once inspections were over, Master usually drove for several hours without saying a word to us. We’d usually give Jessie and Mike massages throughout the day. This was something we didn’t do in front of Emily because it included playing with their dicks and sucking them. The guys liked it when we lotioned our bodies with vitamin E and laid down on them and rubbed ourselves against them. Jessie liked to feel me up and play with my tits, but he never tried to kiss his mother or me. I was thankful for that. It still felt so strange to be serving a family member like this.

I know it’s weird because I now kissed my sister all the time when we were serving together and I’d become so comfortable with it that I now frequently initiated it. I kissed my nephew’s dick several times a day, and yet if he had planted his lips on mine, I think I would have freaked out.

I was also expected to eat Jessie and Master’s hairy asses any time they took a shit while my sister sucked their dicks. I was also the one who had to do the worst chores. I was instructed to lather my tits and rub the toilet bowl clean with them. I licked all plates after they were finished, before my sister washed them. I was also always on the bottom when they tied us up at night.

Chastity had some tough chores too. The men in the RV liked to write on us in Magic Marker. They wrote “Swiffer Tits” on her boobs and made her wax and wash the floor with them. I got Toilet Tits written on mine

I had 490 points by the end of the second night. Chastity had 520 points and I admit I raced her harder, to catch up the second night. It was grueling to earn the points one blowjob at a time and the second night was heart wrenchingly devoid of customers despite how hard we both tried.

Maybe Master saw how the second night hooking had affected our spirits and maybe that was why he began offering us little dares and contests during the day. The reward might be 20 points or it might be permission to smoke a cigarette in peace for a few minutes the next time we stopped. Neither of us chose points over a chance at a puff of a lit cigarette that first time.

One example of a game, was that Master told us to take turns spanking each other. I’d spank Chastity’s ass ten times and then bend over and be spanked by her ten times. We alternated popping each on the tits, ass, and pussy. The goal was to do it until one person gave up—the first slut to give up loses. The first time we played, neither of us gave up, and Master called it a draw when he stopped for gas.

He gave each of us a cigarette to puff on, smirking when we chose that over additional points. He hadn’t promised us to light the cigarettes. It was a lesson we both took to heart. We wouldn’t fall for that joke twice.

During the day, we spent most of our time in the car on all fours pulling our nipples hard and masturbating. There were times that Master wanted one of us to sit up in the passenger seat next to him and flash truckers.

Another game we played was trying to shock truckers. The girl who shocked the most truckers and made them honk their horn by flashing her tits and blowing kisses, won. We didn’t play that one often because we almost made one guy inadvertently veer off the road.

Emily thought we were all bananas and usually remained in the back watching television alone. There were times she got bored enough to talk to the rest of us and come out into the main living area.

“What Celebrity do you most think Mike looks like?” she asked Jessie. We all got to guess. Most of us said Seth Rogan with a beard, and that pleased Mike. He was a bit older than Seth Rogan, but he said he had been told that before.

Mike said that Emily looked like Ellen Page. It was true that my daughter seemed to look a lot like the actress. Emily frowned and made a farting noise with her mouth like she did not care.

“Joy looks like Madonna,” Jessie said. I’ve been told that before. I have kind of a sourpuss grin on my face most of the time, and my hair is blonde like hers. I thanked him and said that I am sometimes compared to Lucille Ball.

“Who the fuck is that?” Emily asked.

Mike told her to watch more Nick at Nite, and she would find out one day.

Emily asked everyone what celebrity my sister most looked like. No one had an easy answer for that. My sister looks like me in the face, but she is shorter. There aren’t many short female celebrities with big boobs and big butts.

“In the face, I would say Renee Zellwegger with the body of Arnold Schwarzenegger,” Emily joked.

Chastity was in the passenger seat next to Master. She had her legs bound and spread, and her hands cuffed behind her back. Anyone in a Semi or another Winnebago would have seen her big floppy tits bouncing while we drove down the highway. She looked disappointed to be compared to Arnold.

Jessie defended her and said she had the body of a Kardashian.

“Yeah, maybe Khloe,” Emily sneered. Khloe is considered the least attractive of all the sisters because she has broad shoulders and is big-boned.

“She is still hot,” Jessie said.

“You think your own mom is hot?” Emily made a face of disgust.

Jessie proudly said that he did. I noticed my sister brighten at the compliment. She thanked him for it.

“People tell me I look like Ed Sheeran,” Jessie announced proudly. He really did look a bit like the Irish crooner.

“Nobody says that,” Emily shot him down. She said he looked like Woody Woodpecker on crack.

“I think Master Jessie looks a little like Rick Astley,” my sister said.

Master suggested Jessie looked like the actor who played Kenny in the movie “We’re the Miller’s”. I had never seen the movie, and nobody else got the reference. Master described the plot to the film.

“A small-time pot dealer played by Jason Sudeikis learns the hard way that no good deed goes unpunished. He was trying to help some teens and gets jumped by thugs and loses his dope AND his money. Now, David’s in big debt to his supplier and -- to wipe the slate clean -- he must go to Mexico to pick up the guy’s latest shipment. To accomplish his mission, Dave devises a foolproof plan: He packs a fake family into a huge R.V. and heads south of the border. He hires a stripper played by Jenifer Aniston and the two teenagers. They all pretend to look squeaky clean so they can sneak back into America with the pot,” he explained that it was a comedy.

Emily laughed and said that sounded perfect for us. “We have fourteen days. Let’s turn this boat around and head to Mexico!” she laughed.

“Well, we are going South of the Border,” Mike said. He said it was always his childhood dream to stop there as a family. “When I was a kid, I would see all these campy old billboards leading up to it. They start about two hundred miles in any direction. This guy named Pedro is telling you to stop in. It sounded fantastic. My dad would always say we were going, but then once we got close he’d say we missed the exit and keep on driving,” Mike said.