In order to get ready to play with Dmitri and Andy, Ruby insisted that I be trained first. She wanted my throat and ass to be ready for the boys to use me roughly. Our regiment began right away. 

In the morning when I awoke with the sun streaming through the blinds, Ruby was spooning me and gently stroking her middle finger over my asshole. I moaned and roused to the stimulation. She pushed her finger deep inside me, causing me to gasp. She pulled out and then told me to head to the bathroom. She wanted me to brush my teeth, shave and cleanse, then return to the bed for inspection. My anus throbbed from the absence of her finger, so I eagerly complied. 

As I washed in the cleansing water of my rainfall showerhead, I thought deeply about what I had agreed to and where it might take me. Ruby wanted me to fuck other men with her. After I had sucked and tongued loads of sticky cum out of her cunt and ass, I was ready to go along with her on her next date in two weeks, when her lovers would be coming back through town. That gave us some time to practice and Ruby was eager to put me to use. 

When I came back to the bed, Ruby ordered me on my back. I lay down and she straddled my torso, backing her lovely holes up toward my mouth. She instructed me to lick her cunt and ass while she probed and stretched my asshole with her long, slender fingers. I moaned into her sex as she pushed in and out of my anus with two and then three insistent digits. I worshiped her labia as she fingerfucked my eager bum. 

We 69-ed for a spell while we both blissed out on rimming each other's assholes, both of us knowing that there would come a time very soon where we would be the centre of an orgy. I could feel her tremble with that knowledge and it made me thrust my hips harder, pushing my hard cock down her throat as she moaned out. I could feel her asshole widening excitingly on my tongue.   

All I could feel was her tight sphincter wrapped around me as Ruby groaned out loud. Letting my cock slide out of her mouth she reached for a long thin vibrator with a bulbous head.  She told me the vibrator was named the 'Hole Trainer' and that I was going to be stretched open to take Dmitri and Andy's big cocks in all my slutty holes. She pressed the head against my rim gently, letting the vibrations relax my opening.

After a few minutes, she pushed harder and the head slid past my narrow opening and into my ass. Holding it steady to allow me to get used to the feeling, she began sawing it deeper and then pulling it against the muscle of my asshole, the vibrations, and pressure opening me up further. After a few minutes of that, she pulled the head out past my rim and as I stretched to allow its escape, she reversed direction and pushed it back in. With a few more strokes, she had my hole so relaxed that the head could easily pass in and out of me without any tension. I felt so stretched and stimulated by the feeling. Then she rolled her hips onto my face and ground her soaking wet pussy into my mouth as she penetrated me, overwhelming me with sensation. 

Ruby fucked my ass and face at the same time, telling me what a wonderful bisexual slut I was being and how proud she was going to be to pimp my holes out to her studs. She climaxed in my mouth while I was moaning and shaking from the delightful vibrations she was putting deep inside me. She didn't stop grinding my face and she kept cumming. Leaving the vibrator deep in my ass, she rose up to rub her clit while perched an inch off of my face. She gasped and squealed and then said, "Drink it, slut!" Her cunt began to gush and squirt all over my face. I licked and drank in what I could, but I was soon sputtering for breath as it kept pouring and spraying, drenching my face, hair and chest.  

Ruby laughed with delight as she rose off of me and saw the results of her ejaculation. She kissed and licked my wet mouth, cheeks and chin, telling me how beautiful I looked wearing all her cum.

"Facials definitely suit you, sexy boy," she purred. "Expect a lot more in your future. Now let's get that cocksucking mouth trained to deepthroat."

Ruby went to her backpack and took out a length of rope and a big red dildo that must have been at least eight inches long and quite thick. She informed me the dildo was named Big Red and told me to put my hands over my head. She tied my wrists to the bed frame, then told me to open wide. She started to rub her huge cock head over my cheeks and then my lips. She told me to lick it and worship it, get it nice and wet for my throat. I obeyed, drooling, lapping and sucking all over it as she moved it deeper into my mouth. 

Deciding I was ready to take it further, she started gently poking me in the back of the throat, gagging me. She withdrew the cock and told me that I was doing very well. "Now it's time to take Big Red into your throat. You need to relax and let it slide past your gag reflex. You may have some spasms in your throat. Think of them as little orgasms." With that, she put the cock back into my mouth and steadily forced it right down my throat.    

I had never felt anything quite like it. I had expected it to be a struggle to endure this big dildo completely filling me, but once the fat head pushed past my gag reflex, it was actually a surprisingly enjoyable sensation. I felt well used and proud of the achievement. Urging Ruby on with my moaning, I bobbed my neck to keep sucking. She began thrusting the whole length of her huge red dick right in and out of my throat, face fucking vigourously.

"Good boy! Dmitri and Andy are going to love how you take it all down. Now try to lick my balls while you choke on my hard cock." 

I was too lost in lust to even consider anything other than complete obedience. My hands tied and the Hole Trainer still deep in my ass, I pushed my tongue out as the dildo was on the backstroke and was able to reach the balls of Ruby's dildo. She didn't let up on the forced deep throating, so I licked and gagged while she pumped in and out of my throat. She reached between my legs and grabbed the Hole Trainer, sliding it in and out of my asshole with one hand while the other fucking my throat. There was no resistance at either end and she spit-roasted me. 

"You're such a good cocksucking slut!" Ruby cheered me on as she thrust into my throat relentlessly. "Get my cock good and slick because it's going up your ass next, my sexy bend-over boyfriend. I bet you're a natural ass slave, too, aren't you?"

Ruby withdrew Big Red from my mouth. It was dripping wet and had long ropes of thick saliva from my throat clinging to it. She cooed with delight and then put it back into my mouth.

"Hold this for me while I harness up, " she instructed. She returned a moment later stepping into a leather harness. Taking the dildo from my mouth, she positioned it and climbed between my legs. "Put your legs over my shoulder, slut and arch those hips so I have easy access to your asshole."

Her words were my command and I readily complied. I was happy to give myself completely to her in hopes of becoming a good bottom for her and for the men who had become a very immediate fantasy for me. 

Spreading open my bum cheeks open with her hands, my legs in the air, Ruby positioned Big Red against my well primed butthole. Even as hungry as she had made my hole, Ruby pushed slowly with her thick cock; plowing steadily inside, she made me gasp and squirm as I accepted this new invasion.

"That's it, take my cock right up your ass" she coaxed. "You're so good, Nick! I've had wet dreams about taking you like this. And here you are, pegged on my big dick. I could practically taste the queer in you when we met. I've wanted to sodomize you the whole time we've been together. Oh god, your ass feels so good!" 

Her words were mesmerizing me, her dildo like an unstoppable juggernaut bulldozing into my rectum with irresistible force. I had a flash of panic as the intensity overwhelmed my entrance, but it was drowned out by the lust inspired by her words and promise of warm, fleshy cocks and thick, hot cum to come. It was exquisite to feel her stretching my ass wider than I've ever been. She was soon balls deep and I could feel her taut stomach on my cock. She leaned forward and kissed me deeply. I was still bound to the headboard and felt completely owned. My head was swimming and I felt like I was underwater.

"Thank you, Ruby," I gasped. "I love your cock in my ass! I love you, baby!"

That last part was not part of our relationship, but I said it and meant it very truly at that moment. Ruby was transforming me, awakening a passion in me that I knew existed. Until that moment, I could feel that want only by its absence but I never knew how to actualize it. She was completing me with her avarice, guiding me on a path to depravity that I didn't truly know could exist. And I loved her wholley for it, my soul being claimed by her as completely as my ass was.  

Ruby kept kissing me as she started moving her hips. We French kissed as she was steadily grinding her big dick back and forth over my surrendered passage. She soon began to thrust more vigorously. As widely presented as I was, I had no choice but to take it. "Take me, Ruby, " I moaned, "Use my asshole for your pleasure."

With that encouragement, Ruby completely let loose, fucking me as she wanted. She growled as she pushed her cock as deep as she could, letting me know the base was rubbing on her clit. She ran her hands all over me: choking my throat, slapping my wet face, pulling my hair, scratching my chest, holding my hips to fuck me harder. As she was getting close to climaxing, she made me beg for her cum. "Tell me, Nick! Tell me who owns your cocksucking mouth and slutty asshole!"

"You own them, Ruby!" I pledged. 

"Say it, slut! Make me cum up your ass. Tell me what you want," she urged breathlessly as she rode me, edging on her orgasm.

"My asshole is yours to fuck and use, Ruby! You can take me when you want and share me with your lovers. I suck all the cocks you want! I'll make them cum and swallow their sperm. I'll let them bugger me and fill my ass with their thick loads. I'll clean your cunt and ass after they fuck you. I'll lick your clit and their balls while you fuck them! I'm your slut, Ruby! Please! Please cum deep up my ass! I need to feel you cum in me! Please, baby!"

Ruby's whole body started to shake and her eyes rolled back in her head. She came with a long groan, sobbing intermittently as she continued to pump into me. She grabbed ahold of my cock, jerking me enthusiastically as she unloaded her flooding contentment into me. I was not far behind her, euphoric with fucking and with her warm tummy rubbing over my cock and balls during the height of the pegging. As I called out that I was cumming, Ruby pulled out and devoured my spasming erection into her mouth. She milked every drop out of me and then crawled up my body to share the sticky ejaculate with me in a fatigued kiss. We shared my cum as I knew we would soon share the seed of other men, feeling drained and used and strangely matured, like my sexual self had been magnified and laser-focused by the experience. 

Ruby rolled off me and released my hands. We panted and slowly regained ourselves lying on the bed. Sunbeams forced their way through my blinds and over our naked bodies, decorating our legs and genitals with bright stripes of light. Ruby kissed my cheek and told me I was a good boy. Then she told me to roll on my stomach and pull my bum cheeks open. Spent and tingling, I followed her directions, spreading my ass open again. She took the bejeweled buttplug and slid it easily into me.

"To ensure you are ready for Dmitri and Andy, you are going to wear this plug whenever you aren't otherwise in use. Understood, slut?"  

"Yes, Ruby," I promised lazily. "I will wear the buttplug when I'm not in use. You own my heart and my asshole. I love you and I'm your slut."