Chapter 2: Taking One for the Team

On the way back to Amber’s bedroom, I made a quick pit stop in mine to pick up some extra lube and grabbed everything I had, hoping it would be enough. I also took off my panties, bra, and stockings because, frankly, I was already too hot, had snagged the stockings on the chair earlier and did not want them completely ruined, and figured we would be spending a little bit of time in the nude as a threesome.

I then took out the plug I had been wearing, bent over, and shot some lube up my ass. Then, using my hand, I slowly inserted one, two, three, and then four fingers in my ass and did my best possible job of stretching my asshole to try and prepare for what might be mission impossible. I then got my good old reliable purple dildo out, stuck it to the toilet seat in my bathroom, and lowered myself down, slowly working it up inside my ass. Once it was about halfway in, I did my best to start circling my hips, moving and stretching everything possible, and soon I was bouncing up and down, taking the entire thing to the base while rubbing my clit like a madwoman. So yes, I cheated and came in my bathroom fucking my own ass on my dildo, because why the hell not?

Thinking that was about as good as I was going to be able to do to loosen up, I grabbed the rest of my lube and headed to Amber’s room.

I had only been away from them for like 15 minutes or so, but they were both naked when I walked in, with Dylan lying on the bed and Amber stroking his giant cock while licking and sucking on the tip of it.

“Get in here, slut,” Amber demanded, flashing me a wicked grin. “Get on your knees on the bed and bend over; my jaw is getting sore.”

By the time I got to the bed, Amber had Dylan almost fully hard again, and she slapped me hard on my ass, making me yelp.

“Let’s try face-down, ass-up. He is going to need some leverage to try and fit that thing in you.”

My thoughts in the bathroom, given the ease with which I had been able to get my purple dildo inside my ass, were that while Dylan was going to be a huge challenge and the widest thing I had ever attempted to fit inside my ass, I had been wearing my biggest plug for hours, I had emptied myself twice with the enema bag and done some stretching, and I was as ready as I was going to be.

WRONG ANSWER!

Amber’s slick fingers worked my asshole, four fingers stretching me wider as she pumped in and out, her other hand spreading the cool gel over Dylan’s now “ threatening” monster! Despite her efforts, a sharp, burning sting radiated through me the moment Dylan’s thick head began to breach my tight ring. The pain was immediate and searing, a hot tearing sensation that intensified with every fraction of an inch he forced forward. My body rebelled instinctively, arms flying back to press uselessly against his hips as a raw, guttural scream tore from my throat. Tears streamed down my cheeks, blurring my vision as the relentless pressure built, my ass feeling like it was being split apart while he continued his agonizingly slow, inexorable push deeper inside.