Chapter 44

Lori tried to contain a chuckle when I told her to shove her thumb up her “fart-tube.” I was glad I could make her laugh. I had been working on that joke about their assholes ever since she called Turtle an “Edgar Allen Ho” because she was dressed like a gothic slut.

The girls pushed their thumbs into their pretty asses. “Don’t cum! You don’t have permission to play with yourself! I just want you to think about how shameful you were this morning when you were trying to make yourselves have an orgasm without permission!”

I didn’t know how women had orgasms or if they could cum this way. I had heard their mother beg to be permitted to cum earlier and extrapolated that this was how they masturbated. I would learn later that both of them DID get off on being denied orgasms and that their pussies started dripping now that they were thinking about it.

Men were far more simple beings compared to women. I got off because I applied a certain amount of pressure and stroked my penis. Watching them do dirty things turned me on but it didn’t make me orgasm. I had a lot of pre-cum on my dick though.

Women were far more complicated. Shaming them this way and making them stand next to each other this way while they THOUGHT about being allowed to pleasure themselves was secretly getting them both turned on.

I ordered them to finger fuck themselves with their free hand while they kept one thumb up their ass. The girls could barely hide the snickers on their face. They genuinely appeared to me like they thought they were getting away with something that they shouldn’t be.

I was naïve and wet behind the ears about women’s sexuality. I would have been shocked and dismayed watching the girls get themselves off the day earlier. I still enjoyed watching them get themselves off! It just no longer blew my mind the way it had at the start of the weekend.

I wanted them to get horny. I wanted them to have to masturbate FOR ME – in front of me, standing up with a thumb up their butt. The fact that they were doing it despite how obviously humiliating and uncomfortable it was – was a power trip for me.

“Can we cum?” Lori asked casually as she circled her clit with her finger in a medium-slow motion and bent her knees slightly.

“Is that how you ask?”

“Can we cum, Sir?” Lori asked in a crisp almost military like way as if she were speaking to her father when he was putting her in her place.

“No, just keep playing with that dirty fish taco,” I insisted with a determined face.

“Don’t make me laugh, Sir!” Lori tried to suppress a smile as she continued frigging herself. She apparently liked my description of her pussy. It smelled a little fishy and the shape of her lips did remind me of a taco. I hadn’t even thought about it until I said it.

Rachel glared at her. She had been relatively silent as she complied with my order to play with herself. “Brian, let us cum, please, Sir?”

Rachel seemed far more serious, and despite the flat affection on her face I could tell she desperately needed to hear me give her permission to get off. I felt a little guilty because honestly if they were Cumming- I wouldn’t have known. They didn’t shoot cum out the way I did. I told her that she could play but not to cum until I gave her permission.

Rachel looked forward with a straight face and kept touching herself the same way.

I had SO many dirty things I wanted to make them do at the mall. I still hadn’t taken them to the sporting goods store. I could imagine throwing darts at their asses or making them sit on a baseball bat. I could dunk their heads in the toilet and give them enemas. The possibilities were endless and they were essentially my perverted play-things for the day.

I was just lucky that there was literally one rental cop for the entire mall, and we hadn’t been caught yet. I was running out of time. The mall closed at 6pm and the day had gotten away from me before I could finish all of the depraved punishments that I wanted to give them. They still had to mow the grass.

I assumed I wouldn’t get in trouble for taking them to the mall. Dennis had told me to make Lori drive us. However, he had given them ONE job and that was to mow the grass. He’d hold me responsible if they didn’t manage that.

“Tittler is in the lead by one point,” I rubbed Lori’s nipple between my fingers. Rachel looked down and sighed. “We have time for only a few more punishments.”

“What’s the point, Sir? Lori isn’t going to back down, and neither am I. She is going to win and I’ll lose like always,” Rachel grunted angrily.

“Why are you such an Eeyore?” I asked. I shifted my focus to Rachel and pulled her pussy lips between my fingers. Lori stifled a giggle when I asked the question. Eeyore was the pessimistic Donkey that always looked on the down side whenever Winnie the Pooh was looking on the bright side. “You think I am going to set you up to fail, Assler?”

“Well, I broke the rules, so yes, Sir. You like watching me twist,” Rachel continued to play with herself.

“I want the contest to be fair or you won’t even try! You need an attitude adjustment,” I said. I wanted to explain that today WAS her fantasy and that her father had specifically arranged for all of this because I wanted her to ‘enjoy’ what was happening to her.

She seemed so ungrateful and snotty. I know I was humiliating her and ordering her around, but I came to believe that this was all a game that they enjoyed playing. It was a bit like playing a game of pretend like cops and robbers and she was the robber that was being tied up or questioned. Lori could take things in stride and even laugh about it – but Rachel usually remained stoic and emotionless.

I could handle that but right now she came across as selfish and that got under my skin. Don’t get me wrong – there was no place I would have rather been than with them. I suppose I was still wrestling with the concept that the girls WANTED this and yet Rachel didn’t seem grateful.

I genuinely felt like the sadistic babysitter who was supposed to be punishing the girls for being rude or petty. I told the girls to stop touching themselves. “That is enough playtime.”

They both sighed longingly. I didn’t know it at the time, but they had both been at the edge of an orgasm and it was excruciating for them to stop right then.

I was going to spank Rachel’s ass. I had done it at the beach and stung the palm of my hand in the process. This time I was going to do it a little different. “Bend forward and stick your wet cunt out! You are getting ten”

Rachel bent forward, arched her back and presented her wet pussy to me. It smelled of lemony-girl juices and glistened. She didn’t argue or protest my decision.

“This is the hardest fucking contest,” Lori chuckled as I began spanking her sister.

I ignored her and slapped Rachel’s cunt. I applied torque by snapping my wrist just as I connected with her pussy. I felt the wetness of her slit as I connected hard with her pussy. “Count Wibble Wobble,” I insisted.

Rachel breathed out when I slapped her pussy again and began counting “WIbble wobble black bobble, wibble wobble out! Turn my filthy pussy inside and out, one of its dirty, twice if its clean, Wibble wobble black bobble, wibble wobble out! Two Sir, thank you Sir.”

The door opened unexpectedly on the third strike. I felt my stomach rise into my throat and butterflies emerge. I had grown so complacent in the smaller bathroom that I really didn’t expect any interruption. I cursed myself for not commanding Lori to keep watch.

The man opened the door and then shut it almost immediately when he saw two nearly naked girls standing side by side. I could have let it go at that. It shocked all three of us initially. This bathroom was far more remote than the others. I had become sloppy and hadn’t had anyone check the door to see if someone was coming.

“No C’mon in,” Lori offered. “My sister is just getting an attitude adjustment. The stalls are empty,” she said politely. I think she thought the look on his face was funny. The man was in his late thirties and wore a mullet. He had a thin mustache and wore a “Molly Hatchet” T-shirt with stonewashed jeans. His face was pockmarked with acne that he must have scratched at one time – making him look a bit like a slice of cheese pizza was grafted to his scruffy face.

He opened the door. I think he probably would have waited outside if Lori hadn’t thought it was funny to invite him in to watch. “Holy shit, what’s going on?”

“I am just spanking her because she is constantly complaining. We are almost done. You are free to use the stalls,” I tried to sound confident. I will admit that I was freaking out inside. I was talking to a grown adult man like I was an authority figure. I didn’t think he would buy it.

“I did not expect to see this in here,” he chuckled and went into the stall. He left the door open and started to piss.

“Can I just count Sir?” Rachel counted the fourth swat politely.

“Wibble Wobble or I start over,” I insisted. Lori looked at me with mischievous eyes and smiled as I humiliated her sister. She was naked as well with her thumb jammed up her ass, but she was clearly loving this scenario as it played out.

“You piss like a racehorse, Sir!” she complimented the man without turning around to watch him piss. “That’s cool!”

“Hey, don’t you go to Witch’s Brew sometimes?”

I stopped spanking Rachel so that I could listen to this.

“I might have, yes.” Lori paused as she answered him as if realizing suddenly that he probably recognized her. The Witch’s Brew was a local bar that frequently featured local rock bands. I had never been there but someone as cool as Lori probably had.

“You were there for quarter beers when Cameron was playing?” he asked as he finished pissing.

“Can I plead the fifth?” she blushed. Lori wore a grin on her face, but she was being avoidant in how she answered his questions. She jokingly asked me if she could put the soap back in her mouth.

When the man turned around in the stall, he introduced himself as Lenny. “Whoa, what is written on your ass?” he could clearly see the words I had written on their butts for himself. “is that a joke?”

Lori didn’t say anything. I slapped her pussy by reaching under her legs and told her to tell him what it says.

“Lenny may be dumb but I think he can read, Sir,” Lori complained. She sighed after I glared at her.

“I was caught playing with my pussy, and I am a naughty girl. It’s no joke. My babysitter is punishing us,” Lori looked deeply humiliated after her admission.

Lenny was a grown man, but he giggled like a schoolboy that had finally got to see tits for the first time.

I once again felt guilty that I was exposing her to people who she would run into again at places she liked to hang out. Naples was a VERY small town and everyone seemed to know almost everyone else. However, the die was cast, and Lori was already exposed to him.

“You are the babysitter?” he pointed at my shirt and laughed. “Playing with yourself is natural. No harm in that.”

“She wouldn’t get anything done on the weekend if she could play with herself anytime, she liked,” I smacked Lori’s pussy again and forced her to stick her hips out and adopt the same position that her sister was standing in. “Tell him what else you did, Tittler?”

“I made fun of my babysitter and called him Tittler because he has a boob obsession.”

“Me too!” Lenny admitted with a wry grin.

“You were caught making fun of your babysitter?” Lori asked with a deadpan expression. She was clearly teasing him but he didn’t catch on.

“No, I have a boob obsession,” he answered honestly. I didn’t like it that Lori was making fun of him. I honked her tits by squeezing them and making a fun noise when I did. “Go on and give her boobs a honk, Lenny.”

“Really?” Lenny was smiling from ear to ear “You don’t mind?” he asked her.

“I am not going to stop you,” Lori shrugged. She still had one thumb up her ass and her other hand was resting on her thigh as she leaned forward slightly.

“Honk, Honk,” Lenny giggled like a schoolboy as he gave Lori’s firm tits a powerful squeeze. It clearly didn’t turn her on, but she didn’t look angry about it either.