How I Got a Harem: Blackmail

A month had gone by since Ashley and Tracie had shown up at my doorstep, and what a month it had been! I had two beautiful women living with me, loving me, and we didn’t see any reason we couldn’t continue that way for the rest of our lives. Little did we know, the party was about to get a little bit bigger…

The first time the three of us made love, Ashley whispered to me a desire to be fucked in the ass. I happily obliged, and since I’ve spent countless hours buried inside Ashely’s loving, heavenly asshole. Tracie was on board with the idea, she thought anal was intriguing and hot, and she loved to help me tongue and finger Ashley’s ass. But Tracie was still only fifteen and the thought of having her own ass invaded by anything, much less destroyed by my considerable cock, scared her. Ashley and I had tried to talk her into trying it, and while she’d expressed some curiosity, we’d never gotten her to take the plunge.

On a crisp Saturday morning, the three of us bundled up in winter gear and headed into the cold. It was just before Christmas and the I decided we needed a Christmas tree. There was miles of wilderness behind my property, whose land it was I had no idea, but I knew we’d be able to hike back there and find a nice fur tree plucked straight from the forest instead of off some lot.

The snow crunched under our feet as we weaved a path through the woods, throwing snowballs and horsing around for at least an hour. It was late morning and chilly. I had already cum once today, I had bent Ashley over the kitchen island and thoroughly pounded her cunt before draining my balls into Tracie’s waiting little mouth, and while everyday with these two meant multiple escapades I didn’t expect anything to happen out here.

Tracie and I had tackled Ashley into a soft snow pile, the three of us melting into a joint kiss, when Tracie suddenly pulled free. “Right now, I’m ready,” she said with eagerness in her eyes.

“What?” I asked.

“I want to try anal, right now,” she said hurriedly.

“Now? Out here?” Ashley asked.

“C’mon,” Tracie pleaded, fumbling to undo her snow pants, “before I get too scared and change my mind!” Tracie removed her jacket, there were still plenty of layers underneath, and laid it out as a blanket. She quickly pulled her snow pants and panties down to her knees and propped herself on her elbows, her naked, white, creamy ass pointed sky high and shone in the bright sun.

“You know what to do,” I said to Ashley. She and I had talked about fucking Tracie’s luscious ass numerous times, so we had a plan. “Tracie,” I said aloud, “Ashley is going to get you nice and ready for me. You just relax.”

Ashley knelt behind Tracie and leaned in. I watched as she gently spread her tight cheeks and Tracie’s puckered butt hole winked at us. It looked beautiful, a tiny dark spot an inch from her smooth pussy. Ashley moved in and began to soak her asshole, sending shivers through Tracie and blood to my cock. I was hypnotized as Ashley’s wiggling tongue wormed its way around and into Tracie’s tender hole. Ashley burrowed lovingly, moaning deeply as she finally tasted the one part of Tracie she never had before, and Tracie sighed and giggled as a gentle tongue tickled her sphincter. I watched for what felt like forever, my cock straining, until I decided it was time for the second phase of our plan.

Ashley and I had decided, based on experience, that it would be best for Tracie if my cock was thoroughly slick and lubed when I tried to fit it inside her virgin ass. In order to achieve this, I swung around behind Ashley and pulled her pants down. The cold air shocked my rigid cock, and by comparison Ashley’s warm, velvety pussy felt steaming hot. She purred as I eased my way in, gently fucking her, planning to use her juicy pussy as lube for our upcoming debauchery.

By this time Ashley had worked her pinkie into Tracie’s tight ass. Tracie mumbled and moaned, yelping at new sensations, but so far she hadn’t lost her nerve. The whole spectacle was enough to drive me overboard but I held strong, my cock throbbing and ready. I slid it free of Ashley and said it was time.

Tracie looked at my pulsing cock, glimmering and thick, and shuddered. “Mark, promise me you’ll take my anal virginity.”

“Oh, I promise!” I smiled.

“No, I mean, you have to do this, no matter how much I say no. I’m feeling scared again, I don’t think I can handle something so big, so I need you to force it in even if I scream bloody murder.”

“You can handle it, baby, you’ll love it!” Ashley sent encouragement.

“I just, I’m gonna say no, I’m gonna try to resist, ‘cause I’m too scared, so you have to force me, ok?” Tracie’s voice was trembling.

“Don’t worry, baby, I’m going to fuck that ass whether you like it or not.”

I mounted Tracie and my cock pressed up against her impossibly tight hole.