The big night finally arrived. I was holding hands with my sexy, slutty girlfriend Ruby, riding up the elevator to a high floor suite to meet up with Ruby's college lover Dmitri and his boyfriend Andy. I had butterflies in my stomach and a buttplug in my ass. Tonight was going to be my first time getting fucked by real cocks. Ruby had prepared me thoroughly. I was nervous, excited, scared, turned on... The anticipation had become almost painful and I needed for this night to happen. 

For the last week, Ruby had been coming over for my anal training. As soon as she would come in and we had kissed, I would kneel on the couch, presenting my asshole for her to plug. She would lick, lube and finger me until I was opened and then I would be filled for the evening. The plug was only removed for her to fuck me with her big dildo and then reinserted until she wanted to used me again. I would have it out to sleep and then have a reprieve until the next evening when she arrived. 

One morning during the week, Ruby told me I was to go to work with the plug in. I did as I was told. We had John, a supervisor from another office, visiting that day. I was trying to be casual while I was making small talk in the copy room, but I was very aware of how handsome this late 50s man was and that my buttplug was in, pressing on my prostate. We chatted about the upcoming staff party and he made a joke about how wild they had been in the past. As my mind started imagining getting wild with him, my cock stiffened. I thought I saw his eyes glance over my crotch, but I wasn't sure. He left with a friendly smile and a wink, saying he'd see me there, brushing against me as he passed. 

As the elevator neared our floor, Ruby rubbed one hand over my cock and reached back to push the plug in a dip deeper. She kissed me hard, making me moan. "Ready, Nick? It's time to suck and fuck like a cheap whore. Can you do that for me?" 

"Yes, Ruby," I crooned. "I'm eager to please them." 

"You will, sexy boy," she purred. "And we're going to take lots of pictures and videos. And I'm going to share them on the internet to find us new playmates. Lots of slutty boys and girls to fulfill all our dirty fantasies. Tonight is a big step, Lover. Let's leave all our inhibitions behind and have a filthy time with these big dicked studs." 

I was rock hard as we made out. The ding of the elevator arriving at our floor came and we stepped out laughing and racing to start our date. Demitri opened the door, sharply dressed with his shirt half unbuttoned, giving a glimpse of his muscular hairy chest. He was a little taller than me and undeniably handsome, with bright brown eyes and an olive complexion. Ruby was quickly embraced in his strong arms, kissing him hungrily. His hands wasted no time finding her bare ass under her very short black skirt. After a few long moments, they disengaged and Ruby introduced us. Demitri fixed me with his lovely gaze. 

"Nick! I've heard incredible things about you. So nice to finally meet!" he said cordially. He had an intense charisma that I could already feel radiating through me. He subtly inclined his head, wordlessly inviting a kiss. I paused a moment and then leant in to kiss his full lips as my girlfriend had just done. He was a great kisser. I let him be the aggressor and sucked on his tongue as he pulled away. 

Andy had been waiting for his introduction. I chuckled nervously as we first shook hands and then was pulled in for a tongue kiss with him as well. Andy had light brown hair and stunning green eyes. Ruby had been very right in describing their attractiveness to me. These were beautiful sexy people who immediately made we want to touch and be touched. 

"Nick, can I get you some Prosecco? Ruby, a glass for you?" Andy asked. We both welcomed the drink. Demitri guided Ruby down to sitting next to her, while Andy invited me to sit next to him on the loveseat. "Come here, Nick, let's get to know each other."

We chatted lightly about what their travels had been like and then both men focused on me, asking me about my job, my hometown, whether I had traveled much. The conversation quickly turned sexual, Ruby letting them know that she had been training me all week for then. I blushed, but was feeling very open to all the dirty talking Ruby was telling these studs. 

"He's wearing a buttplug right now, boys," Ruby told them. "Nick, lift up your bum and let Andy feel it." I did and Andy's hand felt around my ass, groping my cheeks before centring in to find my plug and giving it a few gentle pushes. He leaned onto me and kissed me again while he fiddled with my plug. 

Ruby watched us kissing and she started rubbing Demitri's cock through his pants with one hand while her other hand rubbing her own breast. She soon had Demitri's pants open and his thick cock sprang loose in my peripheral. As Andy and I seperated, Ruby directed me to kneel in front of Demitri. She was running her hand up and down his rapidly stiffening cock. I was soon right in front of Demiti's fat cock, Ruby instructing me to open wide as she guided Demitri's penis over my cheeks, around my lips and then into my open mouth. 

"Oh, yes, Nick, suck that big cock, baby. Run your tongue all over his shaft. Stick your tongue out and lick his balls while he uses your mouth." 

Demitri's cock felt amazing in my mouth. After a week of hard training with Ruby's didlo, this warm, spongely uncircumcised dick felt and tasted heavenly. I settled into a rhythm of bobbing my head up and down pumping this exquisite rod deep into my throat and then back out till I was just holding the swollen head with my lips. I could hear the camera snapping away as I gave my all to blowing my new playmate. 

Ruby slid down Demitri's body and joined me on her knees on the floor. "You have to share, you greedy cocksucker," she whispered in my ear and she kissed me around Demitri's delicious cock. She stole the cockhead from me, leaving me to lick down to cleanly shaven scrotum. I sucked his big balls one after another and worshiped every inch I could get to. He twisted up a little and I pulled his pants off. He took hold of the back of my head and incited me to rim his asshole. I probed and darted my tongue as deeply as I could manage, while Demitri ground his ass on my face. 

Ruby rose up and made room for Andy, who had also striped off. Andy sat down next to Demitri and Ruby told me to suck them both. These beautiful men held their full erections to my open mouth, pumping past each other's cock heads as they thrusted in and out of my lips. 

Ruby got behind me and started to pull my pants off. I was wearing red jockstrap underwear, my ass fully exposed, the bright ruby jewel of the buttplug shiny in the light. Ruby played with my plug while I sucked two big penises at the same time. It felt delightful, being used at both ends, being the centre of so much lust and sexual energy.  

Ruby withdrew my buttplug and poured lube on my inviting asshole. "Demitri, come and take my boyfriend's virginiy. I'm going to guide your manhood into my boyfriend."  

With Andy still using my face, I felt Ruby rubbing Demitri's fat cockhead over my asshole and in gentle circles around my opening. I could feel myself relaxing as Ruby guided the cock more firmly into my ass. I gasped as the flared head slid past my sphincter, deeper inside, inch by girthy inch. My gasps turn to a moan of pleasure as I felt this gorgeous man start to fuck his dick in and out of my no longer virgin ass. I was getting spitroasted, just like we had fantasized and it felt better than I could have imagined. I squealed with pleasure as Ruby urged them on and recorded everything as a video. 

Demitri was a great fuck. He obviously knew how to fuck a man. He varied his strokes, teasing me with the tip and then burying his sizable member balls deep inside me. His rhythm steadily increased until he was near orgasm. Andy pulled out of my mouth and Ruby told me to beg for Demitri's cum in my ass. 

"Please, Demitri!," I pleaded. "Please cum up my ass! I want your sperm in my ass. Please shoot your load deep inside me!" 

Demitri called out loudly, telling me to take it all as his spunk pumped into my well fucked ass. I could feel the warmth of his cum and I loved it. He stayed inside me until he started to soften. When he pulled out, he brought his cock to my mouth. "Suck it, slut! Clean off my cock and get it hard so I can fuck your girlfeind next." 

I once again set to worshipping this handsome man's slackening cock, tasting his cum and my ass and the lube all over it. Andy moved to take my gaping, cum filled asshole as I cleaned up his boyfriend. Andy's hard cock slid right into me, slightly less thick though a little longer than Demitri, reaching different parts of me with his insistent thrusts. I could hear Ruby cheering us all on, letting me know how sexy it was that I was getting Demitri ready to fuck her. 

"Oh, fuck, Nick, that's so hot. My cunt is soaking wet. I want that fat cock deep inside me! Suck him good, baby. Get his big dick hard again so he can stretch out my tight pussy with it."    

I was rubbing Demitri's balls and taking his cock as deep in my throat as I could. All the while I was swaying with the steady, intense buttfucking Andy was giving me. I got my fingers slippery with saliva and cum from Demitri's cock and then started swirling my fingers around his anus. Demitri's cock responded immediately to the anal stimulation and it pulsed to full size in just a few more thrusts into my mouth. Ruby squealed with  delight, spreading her legs wide. 

"Tell him you want him to fuck my cunt, Nick. Tell Demitri that you want to see him fuck me like a dirty whore," Ruby breathed to me as Nick positioned himself above her splaide body. 

"Please, Demitri. Please fuck my girlfriend's cunt with your big dick. Fuck her like a dirty whore," I repeated for the room, spurring Demitri to impale Ruby with his impressive organ. Moving from my mouth to Ruby's pussy, Demitri slowly slid into my girlfriend while I watched, gasping as Andy's long cock was buried over and over again in my ass. 

Now that it was just Andy and I, he intensified his thrusting, pounding my tender ass with long, deep strokes. I begged him, "Please, Andy, fuck me hard and use me to cum. I want you to add your cum to your boyfriend's! Please give me your cum. Pump my ass full of your cream!"  

Andy rode me hard until he called out, "Oh, I'm cumming! I'm cumming right in your stretched out asshole! Here's more cum for you, you lucky bottom boy."

And for the second time, I felt a man's orgasm pumping up my ass. His thrusts set me off and I came hard. I milked his cock as it pulsed and spasmed inside me, trying to get every drop of the cum that I had earned. 

As our orgasms finished and the twitching of his cock ceased, Andy pulled out of me and pushed his cum and ass soaked dick into my mouth to clean, as I had done for Demitri. I could hear Ruby having a powerful orgasm of her own as Andy told me that he was going to fuck her ass once I got him ready. "You hear me, slut?" Andy said. "We're going to double penetrate your whore of a girlfriend. She loves it in both holes. You want to see that?" 

I gargled in the affirmative that I did want to see that, choking on Andy's manhood while he facefucked me. He guided my head and mouth around his cock and balls and even pushed me down to lick his asshole. Once he had been thoroughly fluffed, he let go of me and joined Demitri. "Ready, Ruby?" He asked. "Do you want me to assfuck you while my man pounds your cunt?"

Ruby was growling and gasping all manner of happy slut sounds. Demitri pulled her close and then rolled with her to put her on top of him, cock fully embedded in her pussy the whole time. "Reach back, Ruby," Demitri instructed her. "Spread your ass open for another cock. We loved DP-ing you last week. I can't wait to feel Andy's cock slide against mine inside of you. I love feeling his balls rub mine while we fuck you together. You and your queer boy are such wonderful fuck toys!" 

I lay recovering on the couch, cum leaking from my asshole, totally cockdrunk from the fucking and sucking. Ruby pulled her juicy bum cheeks apart and her hungry little rosebud was winking at Andy, inviting him to join his boyfriend and sodomize her. She looked over at me, her glazed eyes connecting with mine. "Oh god, I love these hard cocks, Nick. Watch them fill me up, like they filled you up!" For a moment her eyes narrowed and she looked at my dripping asshole. "Put your buttplug back in, baby. Keep that cum inside you until they want you again." 

I found my plug and slid it back into place. I was tender but so open and I found myself hardening at the sight in front of me and the thought of getting buggered again. Andy was rubbing lube on his cock and told me to lick my girlfriend's asshole. She was still bouncing and grinding on Demitri's cock, so it was a bit tricky to keep pace, but I knelt beside the bed and tongued Ruby as deeply as I could until I felt her anus relax and open. I told Andy she was ready and he took my place behind her, pushing his fat knob into her butt. 

The three of them quickly found a rhythm, each man thrusting in as the other pulled out. Andy had his strong hands on her shoulders pulling Ruby's ass on top of his cock while Dimitri held her hips passing her back to his boyfriend and then taking her cunt deeply when he pulled her against his groin. Ruby was wild with passion. "Nick, fuck my mouth! I want all my holes filled! Oh, god, I love being a slut! Fuck me with your big cocks!" 

I straddled Demitri's face and shoved my cock down Ruby's throat. I pulled her hair and fucked her face, matching the thrusts of the other men. Demitri started to lick my balls as they swung over him. The excitement soon overtook us all and we came within a few moments of each other. Demitri and Andy came inside of Ruby's cunt and ass, while I shot some cum down her throat, but pulled out to finish all over her beautiful face and hair. 
We all fell back, feeling the afterglow of pleasure and connection course though us. Ruby cuddled next to me and kissed me hard, lips slick with my cum  "Oh, Nick, that was so good! That was amazing."

"Yes, Ruby," I replied. "That was the sexiest thing I've ever done." 

"And we have all night, baby. Lay on your back, I want you to lick the cum out of me," Ruby said. As I lay back, she spread her cunt over my mouth. While I licked, she reached for my legs, raising them and presenting my asshole to the men. Demitri pulled out my buttplug and once again fucked my ass, fast and hard while I drank his sperm from my girlfriend. He came quickly and when Andy replaced him, Ruby shifted her ass to press her anus onto my busy tongue. "Oh, Nick, drink his cum! Lick my ass, slut!"

With Andy fucking my ass and Ruby grinding on my face, I came again, moaning intensely into Ruby as I spurted. Ruby leaned down, taking my cock into her mouth, then rubbing it on her cheeks and lips. I squeezed Andy's cock with my sphincter and we rewarded as he pulsed into me, flooding my gaping hole with even more semen. 

Ruby slid off my face and kissed me again. As we separated. I laughed and laughed at the euphoria of it all, my body limp but wildly alive. 

"I'm so happy to be your slut, Ruby," I said as I shook with delight and fulfillment.