Chapter 7

Inside the nicely wrapped package my Sister brought was a latex butt plug that was purple and yellow. The package read “The stunning Sinnovator Twisted Silicone Butt Plug is sensationally spiraled and features a large spherical tip that senses its point of entry and glides comfortably inside.”

Underneath was a hand-written note in big red letters from Taylor that said “Stick this up your tight ass, you whore.”

I thought that after that the visit would be over, and it might have been if I had the self-awareness to know we should just cut bait and leave after that.

“Why would you give me this?” Ashley looked genuinely hurt. I assumed perhaps that my sister’s intention had always been to deliver the gag gift and get that reaction from her former best friend.

“I don’t know. I thought it would be funny, Ash. I am sorry,” my sister looked straight ahead. She waved at the people standing on the sidewalk staring at her. “I just thought we might be friends like in the old days and you would laugh. I didn’t mean for you to really stick it up your butt.”

“It’s going up your ass tonight, Thunder Thighs!”

“Please Jason, that’s Ash’s gift,” my sister sounded apologetic, and nervous.

“You take it dry, or you can put your slobber on it to get it lubed, but I am shoving it up your fat ass! You should be ashamed of yourself for giving your friend a gift like this,” I offered it up to Taylor.

“I told you that you can punish me anyway you saw fit, as long as Ashley’s parents didn’t stop you. They aren’t going to let you make me jam that up my butt, Jason!”

My sister’s tone was lemony, like a spoiled brat that thought she was never going to be punished.

“You probably bought another one of these plugs for your own amusement anyway, I don’t see why you’d complain about demonstrating one for the swallows. After all, you bought it FOR them ... Let’s see if they will laugh now, Thunder Thighs!”

I waited for an answer from Rachel and Edward Swallows, after I scolded my sister.

“Let’s that bitch wear it dry. Ashley’s Grandparents would have been here for Christmas when we opened that! Can you imagine how embarrassing that would have been for us?” Rachel demanded angrily.

I let Taylor take the butt plug and slip it in her mouth and get spit on it before she handed it back to me. I wasn’t going to be THAT cruel and shove it up her ass dry, but I suspected she would have let me. Her pussy was already good and soaked anyway so it probably wouldn’t have been a problem.

It was a simple matter to press the plug in to my sister’s ass and let it slide straight up her asshole. She even arched her back to make it easier for me.

Rachel and Ashley were no strangers to sex, and not prudes either. I’d imagine having a last name like Swallows probably helped. I had never actually stuck anything UP an ass before though. I wasn’t sure just how it worked.

I worked it in slow.

“Stick it all the way up there,” Rachel demanded I be a little more rough and force the plug all the way up Ashley’s asshole. My sister didn’t resist, but I was afraid I might hurt her.

“You’ll wear that all night tonight,” I promised.

“Yes Jason,” My sister blushed and looked defeated. “That’s fair, but please don’t tell mom and Dad.”

“You’ll wear that same plug over here tomorrow and clean their house, for an hour. Any old dirty chores they have. You haven’t been punished nearly enough!”

I felt like we were playing a game of Jenga with the Swallows family. At any moment, we could get too ambitious and do something so outrageous that even they would tell us to get out. At the same time, I was having fun and I wanted to do it again.

Even though I did not fully understand why, I assumed Taylor was it enjoying this too on some level. She looked miserable, but I noticed a gleam of mischief in her eyes whenever I laid things on extra-thick.

“I wouldn’t want this pig back in my house. I don’t trust her,” Rachel said. “She can mow our grass and trim our hedges.”

“Any problem with that, Thunder Thighs?” I asked. I was feeling cavalier and having fun with my sister’s misery. Taylor pouted and looked miserable, but she had engineered this entire situation. I didn’t understand it but once I stopped questioning it – I enjoyed it.

Rachel laughed that my sister’s nickname was so apropos. She seemed haughty and snobbish. She asked me if I was going to come with her to make sure that she didn’t talk back.

“I’ll be here to supervise,” and I promised more of the same treatment if she talked back. Rachel volunteered to decorate my sister like a Christmas tree. I let her hang a wreath around her neck and use two wires to hang red Christmas balls from their tree on my sister’s nipples.

Ashley pulled me to the side while Rachel berated my sister and hung ornaments from her.

“Damn, I don’t know what you have over Taylor, but I want in.”

“What do you mean?”

“You’ve got some kind of blackmail? When we were in eighth grade, she convinced me to do a blowjob contest at a high school party. Everybody wanted to see if Ashley swallows,” Ashley admitted. “She took pictures and then for the next year she made me her do-bitch. It wasn’t anything like standing in the window naked in front of my parents, but she treated me like her little sex slave.”

That didn’t surprise me.

“I know who you are. I’ve always known who you are, Jason. You were this quiet little turd that stared us during pool parties and watched us dance around on the porch,” she added. She was not wrong.

“I am not buying that she suddenly gave you authority over her and let you put a tattoo on her. That’s fucked up by the way. I wouldn’t have gone that far if I was in your shoes. Taylor never does anything that doesn’t benefit Taylor unless she has too. Taylor’s a fucking asshole, and she has shit on so many people that there could be a thousand sketchy things she was involved in. Still, whatever it is – it’s enough that she’ll let my mom hang stringers on her tits and pinch her ass in our window.”

“I am telling you the truth,” I assured her.

She took my phone and sent a text message to herself. “These are my digits. Text me. I want to help!”

Ashley seemed desperate to participate in my sister’s continued humiliation. I was intrigued – and a little excited to have a college girl want to spend time with me. Even if it was to play with my sister.

I waited around the house after that for about an hour, while we traded Taylor stories. Most of the ones that Ashley could tell in front of her mother sounded fairly harmless, like the plot of the movie Mean Girls. The thing was Ashley was just as vapid, shallow and mean as Taylor. She just wasn’t as ruthless and usually my sister got the upper hand whenever they started conniving together.

Most of Ashley’s stories begin with the two of them deciding to ruin some other girl’s life before she could become too popular. I got the impression there were other stories that she wasn’t willing to tell in front of her parents.

I didn’t have to embellish or lie. The more I started talking about Taylor the more cathartic it was for me. I had just chalked up her behavior to the normal sibling rivalry kind of stuff that everyone deals with.

That is because for me it was normal and it had been all of my life. My sister had asserted dominance in the early years of our lives and I just accepted it. My mom had enabled it because she never gave Taylor any real consequence for her shenanigans. She even laughed because Taylor had a way of making the absurdly wicked seem funny in a certain context.

As an example, there was a summer we went to the beach. She swam under me and stole my swimming trunks by sliding them off of me when a wave came by.

I was old enough to have pubic hair at that point but none on my chest yet. I couldn’t swim nearly as fast as she could, and she held her breath underwater for long enough that I didn’t even know it was her took them.

She raised my swimming trunks on a flagpole on the pier and told me that I had to walk to the flagpole and hold it and she would let me have them back.

My parents found me before I could reach the pier and the throng of people up there on the pier. She told them I was streaking and that I lost my shorts. My parents didn’t believe me that they were on the flagpole, and they were so embarrassed that my mother put me in the car and made me ride home naked with my hands over my dick.

“So that is why, Taylor is going to walk home naked, and if anyone stops to talk to us, she is going to tell them the reason she is walking home.”

“Jason!” my sister protested but she didn’t say she wouldn’t do it.

“You wouldn’t dare!” Rachel smiled wickedly.

I know, I know. You are probably thinking it is total bullshit this family of snobs let us into their house, let my sister stand in their window dressed as a Christmas Tree with a butt plug, and I wouldn’t blame you for being skeptical.