Read Story: SEASON 1 EPISODE 27

It was Wednesday night in late July. My not-girlfriend, Mary, had just left after an amazingly exhausting day together. Well, it hadn’t just been us together, Katie and Matt had contributed to our activities too.

My sister, Katie, had just told me it was time to live up to my promise to let Matt have my virginity. Long story short, I’d nearly suffocated Matt while dominating him and my virginity was part of the deal to make amends. I had also promised to do whatever they wanted, apparently they had some other things planned out for me.

I looked at Katie, trying to hide my excitement. “Wait, now?”

“Yep. He’s already cum in your ass and throat tonight, we’re going for the hat trick. Upstairs, now.”

I started getting wet again, I wasn’t sure if it was because I was looking forward to getting my pussy fucked or because I liked being told what to do. Honestly? I asked myself, it’s probably both.

We went upstairs. Katie had me get on my hands and knees on the floor. She started playing with the plug in my ass.

I questioned her and she just told me to be patient.

She pulled the plug from my ass. At its widest, that plug was two in diameter. I felt something bigger press against my hole. “Before anything else, it’s time for an upgrade.”

She pressed the tip into me slowly and I felt my sphincter stretch. She kept up a glacial pace and I felt myself stretch wider and wider. I moaned. How big was this thing?

“How big is that thing?”

“Oh, you’ll like this one. I had it custom ordered. It’s eight inches long and three inches wide. The spot right before the base is two inches.”

Holy fuck. I didn’t know if I could take that much. “Kate, is that safe?”

She laughed. I only called her Kate when I was worried. “Don’t worry, sis, the internet says you can fit something up to twelve inches up there. And six or seven wide. I’m not going to stretch you that much.”

She continued working on my ass, filling me more and more. I was getting used to it now. It filled me up delightfully. After maybe ten minutes of stretching me out, she pushed it all the way into me, leaving me disconcertingly full. I felt my stretched hole clamp down on the slightly narrower base.

I felt her twist the plug at the base, a novel feeling. Then I felt something fuzzy on the inside of my ass cheeks. “Uhhh, Katie, what is that?”

Katie laughed. “It has a tail attachment. I tell you sis, it makes you look absolutely foxy.”

I got up, feeling the new toy press on my insides much deeper than I’d expected. I turned and looked at myself in the mirror on Katie’s wall. There was a fox tail right sticking out from my ass. I felt a little embarrassed.

“You’ll be wearing that all week, unless someone’s fucking your ass.”

Someone? As in someone other than her or Matt? “Someone?! What’s going on?”

“All in good time, but let’s just say that, knowing you, you’re going to have a very fun weekend. But first, time for the first part of your promise.”

What the hell did she mean by that? Was I going to get fucked my people I hadn’t met yet? Between the prospect of getting fucked more and how humiliated I’d feel walking around strangers with a tail plug. My pussy was soaking wet.

Matt came into the room. His dick was soft.

“Hmm, you’re gonna have to work for it.”

I got on my knees, ready to suck his dick hard.

“”No no, first, I need you to clean out his ass. Ricky left it pretty messy.”

Right, Katie had let the pizza delivery guy fuck Matt’s ass. Well, not like I could say no at this point.