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.