Jason?

"It's going to happen," he said. "Unless..."

"Unless what?" I asked, willing to do just about anything.

"Take Jason downstairs again tonight and have him stick his cock in your ass instead," he said, and when I made a face he made it clear that was the only option. "Same place as last time."

"What if he won't - you know - do it?"

"Persuade him," he said before going into the kitchen. "Good practice for when you get out in the business world."

Dinner was no joy for me, as my mind raced with thoughts of what was going to happen. Jason's Mom. As I watched that petite lady putter around the kitchen I tried to imagine Mr. Caldwell on top of her, mounting her like an animal and sticking that huge organ of his into her bottom. The thought made me shiver, but also made me realize that something like that was possible.

Furthermore, it was clear that a cock was going to go up my ass that night. The only question was which one would it be? The slim sleek tool of Jason's, or the enormously long and fat cock of his Dad's.

Around midnight, I heard Jason coming down the basement stairs, just as I had asked him to. His father slipped into the laundry room and assumed his observational position while I waited, feeling guilty about luring Jason into this.

"Andy? I heard Jason whisper.

"Back here," I hissed, having set up a makeshift bed on the floor consisting of a sheet and a sleeping bag, and when Jason made it back to me, he chuckled at my being naked.

"I didn't want to waste any time," I said.

"That was so good last night," Jaason said. "This time you gotta let me suck your dick too."

"Maybe," I said as I reached up and yanked his pajamas down and started pulling on his semi-turgid dick. "Tonight I want to do something else."

"Like what?"

"I want you to stick your dick in my ass," I said, pulling Jason down on the floor with me.

"What?"

"It will be great," I said as I got on all fours and handed him the tube of lubricant. "Put some on your finger and work it in my bottom."

"I don't know about this," Jason said, but he oiled his finger and did as I asked.

"Oh!" I said loudly as Jason's finger probed deeper into me. "That feels so good, and your cock will feel even better."

I tried to reach back and grab Jason's dick but all of a sudden he backed away and scrambled to his feet.

"Where are you going?" I asked, clawing at him as he moved away from me.

"I don't want to do this," Jason said. "I wanted us to suck each other's dicks. This is just too weird. Sorry."

He fled up the stairs, leaving me naked on my hands and knees with lubricant in my ass, and as I heard the shuffling of feet I knew what what coming next.

"Nice try, Andy," Mr. Caldwell said, his cock swaying in front of him, swollen and glistening with lubricant. "Just relax."

He stuffed a sock in my mouth - a clean one he assured me - for something to gag me as well as bite down on, and when he knelt beside me his finger wasn't soft and gentle, but rough and demanding. I cursed myself for not leaving earlier that evening and avoiding all of this.

He pushed my face down into the sheet when I squealed a little at the introduction of a second finger in my rectum, and when the third finger got shoved into my steaming hot cavity, it felt like I was being ripped open at first.

"That's it," Mr. Caldwell said. "Just relax and enjoy it."

He withdrew his fingers and lifted my lower torso up as he climbed behind me, and I could feel the prickly hairs of his thighs against the backs of my legs as he moved closer.

There was nothing gentle about what happened next. I felt the bulbous head of his cock at my opening, pressing into my tender ring. The pressing turned to pushing, and while Mr. Caldwell grew frustrated he pushed harder.

Like trying to stick an apple up my ass, I remember thinking, realizing that there was no way this was going to happen. Then, suddenly Mr. Caldwell lurched forward as the head of his dick popped inside of me. The pain was blinding at first, but my muffled cries were drowned out by the low growls that came from Mr. Caldwell.

He made short quick thrusts at first as he leaned over me and worked his cock deeper into me. It felt after a minute like he had to have the whole thing inside me, as impossible as it seemed.

"That's it Andy," mr. Caldwell rasped. "Almost have half of my cock in you."

Half?

My entire body was tingling as his thrusts became deeper and harder, and I could feel his balls slapping against the underside of my crotch as he grunted above me like an animal.

Then he stopped thrusting into me and let out a feral sounding moan. I felt his cock jerk a couple of times, and that was followed by a warm feeling filling my bowels, and just as quickly, it was over.

"You loved it, didn't you?" Mr. Caldwell said as he took the sock out of my mouth, wiping my burning, tear-stained cheeks with it.

I shook my head no, glancing down in shame at the pool of cum on the sheet in front of me and trying to hide the sight from Mr. Caldwell's eyes.

The semen was mine, and while I didn't even get an erection during that entire episode, amidst all the pain and humiliation my cock had started to tingle and for whatever reason I had one of the most prolonged and intense orgasms imaginable.

Mr. Caldwell was now helping me to my feet, and my knees were having trouble keeping me upright as I felt his cum oozing out of my ass and down the inside of my legs.

"Okay?" Mr. Caldwell asked, and I nodded.

"I just wanted you to know that I was going to fuck that ass of yours no matter what happened with you and Jason," Mr. Caldwell admitted. "That ass of yours is just too much for me to resist."

"Feels like you're still inside me," I said as I let him help me up the stairs and into the bathroom.

I took a long and soothing shower, and after I dried off and went to bed I was feeling a lot better. Slipping under the sheet, I had just dropped off to sleep when I heard the squeaking of the door opening and then closing again, followed by the bed moving as Jason climbed in behind me.

Jason Junior, not senior.

"Andy?" Jason said softly as he spooned against me. "I changed my mind. Do you still want me to - you know?"

"Be gentle, okay?" I whispered, reaching over for the lube and letting him slide his finger inside of me.

"I wouldn't hurt you for anything, man," Jason said, and I could feel his hardness against my backside as he probed my aching ass. "I just don't know how to do this."

Too weak to do anything but stay rolled on my stomach, Jason climbed on top of me and slipped his long slender manhood into me after only a brief fumbling, and as he impaled himself in me he let out a contented groan.

"Oh Andy, that feels so tight!" he hissed into my ear, and while that didn't seem posssible, it was true enough.

He didn't last as long as his father, but the result was the same, and after Jason filled me with his seed he rolled onto his side and reached down between my legs.

"Wow," Jason said as his hand, which was on the way to pleasure me, instead found my limp cock which was dripping with my cum. "Did you cum too? That's so awesome. I can't believe how good that felt. We can do this all of the time come fall when we room together at college."

Jason fell asleep soon after, and the sun was just rising when I woke him up.

"Better go to your room," I suggested.

"You're right," Jason said, climbing to his feet. "Imagine if my old man caught us like this! He would kill me. He hates queers."

******

Chapter Seven: Night again.

The bedroom door opened, and as I looked over and saw the person I most wanted to see, a shiver went down my spine.

"Told you that you would be begging for it by the time I finished with you," Mr. Caldwell said as he locked the door behind himself and pulled off his robe. "And once again, you're ready. I like that, even though I know you can't speak.

I nodded, my mouth full of the sock I had just placed in there, and as I waited on the bed on all fours, with my backside up in the air and well primed with lubricant, Mr. Caldwell climbed behind me once again.

It hurt, but not as much as the night before, and that would likely be true for every night that followed during my stay at the Caldwells.

******

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