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. She bit her lip and I felt her whole body go tense. Ashley knelt behind us and reached her hand in to hold Tracie’s ass apart. I pushed down, slowly, and felt Tracie’s tender hole fight me. She screamed relentlessly, a violent echo pulsing through the forest, as I crushed my cock down into her. When the force finally bore her open her scream became an empty, open-mouthed, silent cry. Her ass spread to a width she’d never imagined, a tight ring suffocating my cock, and Ashley mumbled words of encouragement.
“Nahhhhh!!! No! Fuck, no! Mark, get out, get out of my ass!!!!” Tracie screamed at the top of her lungs.
“Nuh uh, baby, you’re ass is getting fucked!”
“Fuck! No, it hurts, Mark! Fuck! Please, please, please!” she cried. Somehow, this made the whole experience that much hotter. Her body squirmed but was held beneath my weight. Her ass twitched and clenched, but Ashley held her open and with each passing second I bore another millimeter deeper. To my surprise, Ashley got in on the action.
“Shut up, you little whore, you love it! This is how we treat little sluts like you, right Mark, we fuck every slutty hole on their bodies!” Ashley hollered. This surprised me enough, but then I felt a strange sensation deep inside Tracie. It was Ashley’s fingers, two of them probing deep inside Tracie’s pussy and rubbing the underside of my cock through her flesh. Tracie wasn’t just being anal fucked for the first time, she was being double penetrated.
By the time I’d gotten balls deep in Tracie’ ass she’d lost the ability to form words. She grunted each time my cock punched deep inside her and soon I was grunting as well, nearing explosion.
“That’s right, baby, he’s gonna cum in your ass! Your ass is just another cum hole for him, you fucking whore!” Ashley’s abusive language drove me wild, and I fiercely fucked downwards and landed deep in Tracie’s abused rectum. I unloaded, my cock spasming and pulsing inside Tracie’s ass. I filled her with hot cum, pumping it in deep, dark corners of her bowels.
The three of us collapsed together and laid for a long time in the snow, catching our breath. Tracie thanked us both for not stopping and we showered her with affection.
After picking out a tree we stumbled our way back to the house. As we walked, I noticed footprints in the snow that seemed out of place. I didn’t mention it to the girls, didn’t want to scare them, but I was sure there were human boot tracks that had followed us that weren’t any of ours.
The mystery of the tracks in the snow nagged at me for the rest of the day. We had made ourselves busy with Christmas decorations, but the whole time I was side tracked and concerned. By night fall I felt like we needed to get out of the house, so I suggested the three of us take the short ride into town and see a movie.
The little town nearby was a dinky, quite place. Even on a Saturday night, the one-screen movie house was just about empty. The three of us took our seats in a back corner of the big theater with no one around us for rows. Tracie was to my left and Ashley to my right, and I leaned back comfortably and put my arms around them.
By the middle of the film Ashley’s hand was beneath my belt and slowly stroking my cock. I looked around to make sure we were in the clear before slowly unzipping my pants and poking my cock through the fly. I heard Tracie giggle and Ashley wasted no time, lowering into my lap and smothering my cock. I closed my eyes and leaned back, letting the pleasure overwhelm me, and I drifted off and enjoyed a loving blowjob. Tracie gently ran her fingers through Ashley’s hair and my hand fell to Ashley’s ass. I turned to Tracie and we locked in a passionate kiss that didn’t break for most of the rest of the film.
Ashley had spectacular skill, it was like she knew my cock better than I, and she worked me thoroughly but never let me release. The blowjob lasted forever, it was heavenly, but I needed it to finish before the movie ended and the lights came on. Still kissing Tracie, I moved my hand up and held the back of Ashley’s head firmly. I began to flex my hips, fucking upwards into Ashley’s mouth and forcing my cock into her throat. Her soft gags were lovely. I moaned into Tracie’s mouth as a dense load of cum erupted and disappeared into Ashley’s belly.
When I finally opened my eyes I was shocked and scared to discover that someone had spotted us. Across the theater I saw a woman staring directly at me with a stern look on her face. I couldn’t make out much about her and I prayed she hadn’t noticed that one of the women with me was underage.
The movie ended and the stranger had already left, leaving me to wonder if she’d headed off to call the cops. But in the lobby I saw her, leaning against the wall near the bathrooms, and when my eyes met hers she motioned for me with one curling finger. Shit! What the fuck was going on?
When we got to my car I lied to my girls, something I didn’t like doing, and said I must have dropped my wallet in the theater and that I needed to go look for it. They offered to help but I insisted they stay in the car. I hustled back inside, afraid of what I would find.
When I reentered the theater I saw her there again, and she slipped inside the women’s restroom when she saw me. I looked around and made sure no one saw me before hustling in there myself. She leaned against a sink and had her arms folded, a coy smile on her face. She had dark black hair that flowed past her shoulders and as far as I could tell a trim figure. She must have been in her late thirties. She had on professional attire, a bit overdressed for the movies, and I noticed she had distinctly full lips. I’d be lying if I said I wasn’t trying to guess how many cocks she’d wrapped them around, even though at the time I was scared and nervous. I also noticed she had deeply tan skin and, upon further inspection, she was certainly of Native American decent.
“I’m glad you stopped to talk with me, or else I’d have to call the police,” she said, frowning.
“Listen, I’m real sorry about what you saw back there, I didn’t think anyone was in the theater or else I never…”
“Yeah, public nudity and a blowjob are one thing, but a slap on the wrist for those. Now, anally raping a fifteen year old girl, that would really get some attention, don’t you think?”
I was taken aback. “I don’t know…”
“Yes, you do. Mark, you had your cock so far up Tracie’s ass it nearly came out the other end!” How did she know our names? “And you and I both know she was consenting, but that doesn’t matter if she’s underage. Plus, it wouldn’t be too hard for me to edit the footage and make it look an awful lot like rape.”
Holy shit. She had followed us in the woods! I had too many questions to ask all at once, so I cut to the chase. “Okay, look, is this blackmail? Because if it is I can pay, alright, there’s no need to let any of this leave this room.”
“Well,” she started to move towards me, “it is blackmail, but it isn’t money in return.”
I shook my head. “Well, what then?”
“I want in,” she said slowly, putting her hand on my arm for emphasis. She had large, hazel eyes that bore into me.
“You… wait, what?”
“I’ve been watching you guys for two weeks now, and I’m fascinated by what you have, Mark, and I want to be a part of it!” I could see excitement in her eyes as she spoke. “Listen, you should probably get back to them, but we need to talk about this. Meet me Tuesday afternoon, 1 o’clock, at the coffee place around the corner. And Mark, if you’re not there, I will go to the police.” I was stunned and she took the opportunity to plant her soft lips on mine. Then she left.
The next few days were torturous. Sure, I had more than enough fun with Ashley and Tracie, but I was distracted by the mystery woman from the movie theater and her shocking proposition. She was sexy, I wasn’t afraid to admit, but the idea of adding another woman to what was already a complex situation seemed ridiculous. Not to mention there was no way Ashley and Tracie would go for it. Our relationship was built of caring and affection, and this woman was trying to muscle her way in through force, and it would just poison the water.
Tuesday at long last came and I made a solo trip to the grocery store. Before hitting the market, however, I stopped in town for a coffee. Sitting in a corner booth was the woman, and she flashed a large smile when she saw me. She was looking at something on the table, some papers.
I got my coffee and sat across from her without a word, waiting for her to do the talking. “This is great stuff, really, I really enjoyed fingering myself to these,” she said, sliding a photo across the table to me. It was a clear shot of Tracie on her knees in the snow, my cock halfway in her ass. “Oh, and this one gets me every time!” she laughed, sliding another at me. It was a zoomed in shot of my cock, a stream of cum captured in mid-burst flying violently from me.
I covered up the photos nervously. “Okay, okay, look, what do you want?”
“For a while, I thought I’d hit the jackpot just taking these pictures. Watching you three was like having my very own, real life porn to enjoy. Then I realized, porn is nice but not really satisfying, and I had the opportunity to really join in. Haven’t you ever seen porn and just wished you could actually be there? Well, I realized this was my chance.”
“How have you been watching us for so long?” I asked.
“Mark, I’m a private investigator. Don’t worry, no one hired me or anything. I noticed you three a couple of weeks ago in town and somehow I just thought something was fishy, so I used my skills to follow you guys and see what was up. So what do you say, Mark? Can I be your third girl?”
I was flabbergasted. “Uh, I don’t even know your name.”
“It’s Jessie. Mark, don’t you think I’m attractive? Don’t you think Ashley and Tracie would find me attractive?” she asked with pouting lips.
“Of course, I mean, you are, but it’s not the simple. I don’t think we could get the girls to go for it even if I wanted to.” I felt a soft pressure between my legs, Jessie was wiggling her shoeless foot against my package.
“Don’t you want to?” she asked with a smile. She nimbly flicked a button free on her blouse and revealed the top of wonderful, tan cleavage. Of course I wanted to.
“Well, yeah, but I don’t think it’s possible. And I don’t think blackmailing the girls is anyway to win their hearts. I mean, sure, you could force us to let you in, but it would be fake and loveless, it wouldn’t be genuine.”
Jessie smiled. “Mark, I’ve thought about this. I know that. Listen, the girls will never find out about the blackmail. The blackmail is just to get you to go along with my plan.”
“Which is?” I was intrigued.
“Ah, so you’re on board?”
“Well,” I paused, asking myself the same question. “Do I want to fuck you? Yes. Would you be a remarkable addition to my already unbelievable sex life? Yes. But I don’t want to fuck that up, understand?”
Jessie took that as an all out yes. “Okay, so here’s what we do. This weekend you tell the girls you want to have a big, Christmas blowout party. You get a lot of booze, decorate, the works, and the three of you get good and wild. Then, when the girl’s inhibitions have been lowered, you tell them you have a big surprise for them. Then you send me a text,” with this she scribbled a phone number down on her napkin and slid it to me. “You ordered a stripper for the party, that was the big surprise. I show up, we turn the lights down and I give a very intimate performance. By the time we get Tracie drinking schnapps out of my pussy the deal will be done. We’ll have a wild night and I’ll be in.”
Well, that certainly sounded like a plan I liked. “Hm, well, I’ve got to honest, Jessie. Even if that all goes as planned, I’m not sure that the girls will want you to join us afterwards. Who’s to say the next morning you leave and that’s that?”
“Trust me, I’ll be in. It’ll be organic, the girls will think it just developed magically. Only you and I will know the truth, and something tells me it doesn’t bother you.” I began to voice more concern but Jessie interrupted me. “Look, Mark, you have to go along with this. That’s the blackmail. You have to give my plan a try. If it doesn’t work, if the girls don’t want me in, then I won’t push it any further. You’re right, I can’t force my way into their hearts. So you have to let me try, but if it fails, I won’t bother you anymore.”
I guess I had no choice, what with the blackmail. Though, inside, I knew I liked this plan a whole lot…