The two days passed quickly. Aside from sucking off Ross, I had spent the time preparing my ass for what was inevitably going to be a wild ride. By the night before, I had managed to fit three fingers in. It was a tight fit for sure, and I’d be lying if I didn’t say I wasn’t a little nervous about the pain.

I woke that morning to Ross’s cock poking at my lips, a departure from our night time blowjob regimen. I opened my mouth in confusion and he pushed it in deep, causing me to choke. But, as far as he was concerned, we were past the point of my throat training.

“Ohhh yeah, Mikey. They just left to get breakfast on the road. Figured it was time for your feeding too!” He said with a laugh as his cock started moving in and out.

Steadying myself on my arm, I was able to get into a slightly more comfortable position and my gagging calmed slightly, but it was still a struggle. My face was dotted with the same spit and tears that characterized our first couple of “sessions.”

At that point I noticed that Ross was completely naked. Even with my current gagging predicament in mind, it immediately hit me how hot and masculine his body was. I let out a whimper-like moan into his cock as I took it all in.

He grinned down at me, knowing I was checking him out.

“That’s right, no need to hide away this weekend. Let’s see that ass,” he said triumphantly as he ripped my blanket off, revealing my nude body and hard cock.

I obediently rolled onto my stomach, which had the twin goals of allowing for easier cocksucking for me and a view of my ass for Ross.

“Mmm fuck yeah,” he moaned as he reached over and gave it a hard slap.

“Wiggle it back and forth while you blow me,” he ordered.

I complied, feeling empowered now that his cock was sliding in and out of my throat with ease. I also found myself turned on by how into my ass he appeared to be. He kept reaching town to squeeze, poke, and prod it as he fucked my face. I started playing with his balls just how he liked and it wasn’t long before he was holding my face in place against his pubes and cumming down my throat.

“Unnghggg yeahhhh drain my fucking balls,” he shouted as he dropped his load.

We hadn’t done a ton of dirty talk up to that point out of fear of being overheard it. I found myself enjoying it, using the little oxygen I had at that point to do another whimper moan before he finally released me.

The sight of his spit-soaked post-blowjob cock was honestly something I never got tired of seeing. I still found it improbable that I had taken the entire thing.

“Fuck yeah, Mikey” he said while catching his breath and taking a seat on the bed.

His hands immediately went to my ass as he spread my cheeks and looked at my hole.

“Heh, it’s winking at me. Think it’s as hungry as your mouth,” he said in wonder as he gently circled his finger around my hole.

I was unbelievably horny and turned on at this point. I found myself involuntarily arching my back and pushing my ass against his finger.

“What do you say, Mikey? Want me to fuck your ass today?” He said.

“Y-yeah,” I said with a tinge of nervousness that still accompanied by inexperience in vocalizing my hunger for cock.

“Say it, then.”

“I…want you to fuck my ass today” I weakly responded.

“C’mon, you can do better. Louder, and like how you wrote about in your cockboy notebook,” he said with a laugh.

I blushed and tried several more times, none of which pleased him, but I was growing more and more hot and horny with each iteration.

“C’mon, cockslut! Like you mean it!” He said in a jovial yet loud way.

It was the first time he had called me a name. For whatever reason, it excited me tremendously.

“I WANT YOUR BIG COCK IN MY TIGHT ASS MORE THAN I’VE WANTED LITERALLY ANYTHING EVER. I FUCKING LOVE YOUR COCK” I yelled, loud enough where anyone passing outside would have heard.

“Right on, Mikey!” He replied as he slapped my ass. “I’ll need a few to recover from your cock gobbling this morning. Go get cleaned up and meet me in the living room, cockboy.”

He stood up and left. I watched his swinging dick with hunger. I was for sure his cockboy.

I fought the unbelievable urge to jerk off and headed to the bathroom. I cleaned myself out and took a shower, sensually feeling up my soon to be devirginized ass. Once dried off, I walked nude to the living room.

Ross was hanging out on the couch with a bottle of lube and a huge grin.

“C’mere,” he ordered.

I walked over to him and stood at attention like an obedient puppy. Being nude in front of him was a little unnerving considering our different body types, not to mention cock sizes, but my own horniness was putting a lot of those concerns on the back burner at this point.

He grabbed me by the waist and turned me so my ass was facing him and then applied pressure on my lower back while saying “bend over, hands on your knees.”

Once I was in this hunched over position, he examined and played with my hole much like this morning, keeping at it for a while until I heard the lube bottle pop open.

“How long have you been dreaming about sucking cocks and getting fucked, Mikey?” He said calmly as he applied some lube to his fingers.

“Since I was a teenager,” I answered, truthfully, as I waited for what was coming next. Was he going to fuck me in this position?

“That’s a loooong time to wait. Surprised you didn’t whore yourself out on Craigslist or something,” he said as he spread my cheeks.

I shivered as a lube covered finger massaged around my hole. I had in fact put anonymous posts on some places, but had always chickened out.

“Works out well for me, getting to break you in,” Ross continued as he applied pressure to his finger.

It slid in halfway easily, considering I had fingered myself in the past and knew how to relax. He pumped it in and out slowly until it was fully in and then got to work on a second. I let out a moan, partly from the pleasure and also for just being on display for him like this and how he was talking to me.

“That’s it, Mikey. Gonna get your hole nice and open for my cock. You’re going to wish you had just told me you love cock sooner. I could have been balls deep inside of you dozens of times by now, ” he said as two fingers now fucked me with ease.

I moaned and my legs felt wobbly. I felt like a bitch in heat as he worked a third finger in.

“Fuck yeah, we’re almost there,” Ross began with noticeable excitement in his voice.

My moans came regularly as breathing picked up. There were several limitations with fingering oneself that Ross wasn’t encumbered by as he continued to open up my ass. As a result, I was feeling pressure and pleasure I had never experienced before. And then it stopped.

“Alright, get down here and lube up my cock,” he ordered.

I dropped to my knees, took hold of his cock, and was just about to slip it into my mouth when his laughter stopped me in my tracks.

“With this, Mikey…” he said holding the lube bottle out.

I blushed as I applied a generous amount to my palm and stroked it up and down, making sure to get it nice and slick. It was fucking beautiful as ever and I felt like I could just barely contain myself.

“You like being my bitch?” Ross asked, breaking my concentration.

“Yeah,” I mumbled as I continued to stroke.

He took my hands off his cock and tilted my head so we were looking directly at each other.

“You like being my bitch?” He asked again.

“Yes,” I responded with more certainty.

It wasn’t a lie. I knew the power balance here and had no illusions about romance, tenderness, or reciprocity in any of this. I recognized that Ross made the rules and I followed. I was his bitch. I was his slut. I was a mouth and, soon to be, ass that he could use whenever he wanted. I had never complained. I had grown to love it all.

“Good, cockboy. Because that’s not going to end any time soon. I’m going to breed your ass at any time just like I do with your mouth, got it?” He asked.

“Yes. I understand,” I replied, unable to keep my eyes from drifting to his cock.

“Good. Now get that slut ass in the air and your face on the ground,” he said as he stood up.

I naturally obeyed, getting into the face down ass up position he asked for. I could feel air teasing my hole as I heard him get into position.

One hand grabbed my hip while his other guided his cock to my hole. Once in place, that hand hooked onto my other hip. He pulled me back and pressed forward simultaneously, forcing his cock through the opening of my hole, stretching it slightly.

“Oooh, mmmphh” I moaned in disbelief.

It was still in the well lubed and stretched portion of my ass and it was all pleasure.

“Fuck yeah, nice tight ass,” Ross moaned as he continued pushing.

While Ross displayed more preparation and care at the start of fucking my ass, the same sink or swim philosophy he had for my throat began to show here as his cock showed no signs of stopping. The pressure and pain started to build as it snaked further and further.

“Waahh,” I wailed as I winced in pain.

“Ooh yeah, buckle up, baby…we’re almost there,” Ross responded as he smacked my ass.

I bit my lip as my body shook. Another opportunity to say something and yet I didn’t even think of asking him to stop or slow down. By every metric, my body was his to use. My cock had shriveled and was flacid, beads of sweat pooled on my body, and every inch in felt like the air was being knocked out of me.

Just when I thought I couldn’t take it, my ass came to rest against his pubes and balls. I breathed a sigh of relief as the lack of moment somewhat dulled the intensity of the pain.

“That’s a beautiful sight,” Ross said as he squeezed my ass and steadied himself.

“No going back now, Mikey. We’re about to see if your ass takes loads as well as your throat. You think you’re in love with my cock now? You’re going to be fucking over the moon for it soon. You can write in your cockboy notebook about how you took the real thing and loved it,” Ross continued, his words dripping with domination and control as he looked down upon my impaled and stretched ass.

With that, he started moving in and out slowly.

“Unnnghh,” I wailed as the pain resumed, my exhale being too powerful to be constrained by biting my lip.

“Just growing pains, Mikey. You’ll see,” Ross laughed as he took it nearly all of the way out and slid it in again. “You were born to do this.”

And so it continued for a few excruciating minutes. I was nearly at the point of discounting anal entirely as something I’d ever want again when my sense of pain dulled, allowing for a chorus of other feelings to join in. My grunts of pain ceased and I was quiet for a time.

There was the pressure of the stretch, the fullness of his cock, and the godlike feeling of it brushing against my prostate. It was subtle at first, my cock registered it before the rest of my body and once again became erect. My ass recognized it second, involuntarily squeezing Ross’ cock at the moments where it felt best.

The pleasure that eventually set in far outweighed any of the pain it took to get there. Ross had been right once again and I was getting this pleasure as a result of letting him guide me, by me being his bitch.

“Mmmmph,” I moaned as I began to cautiously move my ass back in time with Ross’ thrusts, which were increasing in speed and intensity quickly.

“Told ya, cockboy,” he laughed as he sped up even more. “Let’s hear it, let it out.”

“Mmmmwwahhh oh god,yeah…yes…yess…fuck me…fuck my slut ass,” I moaned in a whiny slutty tone.

I was now throwing my ass back hard, savoring every inch of his cock. As much as I loved giving blowjobs, this was galaxies better. My cock leaked precum as my moans grew in frequency and volume.

“Yeahhh..fuck yeah…,” Ross roared as he slammed me on and off his cock, maneuvering my body like a rag doll and going balls deep with each thrust.

He let loose ass slaps, shoulder and neck grabs, and hair pulling at random. It all drove me wild and I was now looking over my shoulder at him best as I could, shooting him a look of total lust and obedience. I could see in his eyes how my subservience pleased him almost as much as my ass and mouth.

With high speed and low effort, he took his cock out, flipped me over, put it back in and fucked me in the mating press position, looking me in the eyes as the butt pounding continued.

Looking up at Ross while he fucked me made it so much hotter. I gazed lovingly up with my pupils dilated and my mouth agape, feeling unbelievable amounts of pleasure as he rammed into me. I reached out to touch his firm chest with one hand, feeling his muscles.

I had been aware of my dick leaking precum ever since the pain ebbed. I was still erect and my orgasm was building in ways unfamiliar to me as someone who had only gotten there in the past by jacking off. Warmth and pleasure radiated my groin area. My eyes rolled back as Ross brought me closer to the edge.

“Oooh, yeah…I…I’m…oooh,” I moaned as I looked up at Ross.

“Heh heh, cum for me, cockboy. Give yourself to me,” he said in-between breaths, obviously getting close himself.

“Mmmmm, I…I’m cu…cumming,” I moaned in an incredibly whiny and slutty way as my body shook. Cum splashed across my torso and neck as I screamed in pleasure

“Fucccck yeahhhh cockboy, take my fucking load,” Ross yelled, pumping his load deep into my ass as I was still coming down from my own orgasm.

I had the feeling right then and there that the feeling of my ass accepting his load would be one I’d remember for the rest of my life. My legs, ass, and mouth were sore as all hell, but it didn’t matter. I had been thoroughly deflowered, bred like a total bitch.

After a few minutes of recuperating, Ross lifted off and pulled his cock almost all the way out. He paused for a moment and then slammed the full length back in, causing me to gasp and moan in surprise. I was in such a compromised and exposed position, naked with my legs pinned back, and he was just relishing the power he held over me.He did it two more times before finally pulling out.

“Now that’s a well-fucked ass,” he remarked with a grin as he examined my hole while continuing to hold my legs up. He playfully slapped my thigh and let my legs drop to the ground. I was physically and emotionally spent, but Ross was very much a “the show must go on,” type of guy.

He dragged me into the shower and had me wash him off, pushing me to my knees when it was time to soap up his cock and balls. It wasn’t long before both of us were hard again and he playfully slapped my face with his cock as the water rushed over us.

Once dried off, he put a movie on the TV and had me lay my head on his lap so I could lick his dick and balls. He specified licking only. I think he was plenty spent too after blowing a load each in my throat and ass. He rested his palm on my ass and squeezed off and on while my tongue went all over his cock and balls. I ended up falling asleep, drooling on his cock as I lightly snored. This was also how I fell asleep at the end of the day, but not before he had me suck him off after making him dinner. As I drifted off, I recalled we still had one more day without roommates. I hoped it would be just like today.