Besides, pleasurable as my mouth and finger had been for his hole, the pleasure still had to fight against the pain: The clothespins, his spanked ass.
Lastly, there was the fact that Prasang was doing this for money and money alone. He was not a natural masochist in the same way I was a natural sadist, which meant the pain worked against rather than for his arousal.
I sighed. “Your new masters aren’t very impressed with you, Prasang. That reflects on me as a master, too. I think we’re going to have to take things to the next level.”
I looked around, wondering what to try next when my eye fell on the fruit tray Martin and Gary had been sharing with us.
One of the bananas the bartender had given them was, to say the least, formidable. I blinked, not believing my eyes at first. It had been lying under some of the other fruit we were force feeding Prasang and I hadn’t noticed it before.
A devilish shudder went down my spin and my cock stirred.
I tapped Gary on the shoulder and gestured to the banana. He picked it up by the stem and dangled it above him. It was even bigger than I realized. From where I sat, it appeared to be about ten inches long, its diameter just a centimeter or two short of a cucumber’s. It was not the typical yellow of a cavendish, but lime green. It ran moist with juice from other fruit.
“My, my, but would you get a load of this beauty. How could we not have thought of it before, Martin?”
Martin adjusted his glasses and inspected it. “That’s no banana, that’s some kind of plantain hybrid, though why the man would give us one of those I have no idea. He must have some sixth sense, understood it might come in handy for us this evening.”
Gary lined it up against Prasang’s (almost) hard cock and whistled, impressed. The two were almost the same size, with Prasang still needed to do a little growing.
“Oh yes,” Martin nodded back at me, “I think this’ll do the trick. Just what the doctor ordered.”
Prasang’s eyes bulged at the sight of the plantain. I was amused as it dawned on him what we were planning to do.
Up to then, he had had, at most, two fingers in his ass (Gamon and I double finger fucked him back at Sexy Guy, which made him spurt beautifully). He had never taken anything even close to this size before.
The poor boy began his pitiful, stumbling protests again.
“W-wait, master, please, I can get hard! I’m almost there, really! I can (GULP) I can make myself big and hard for you!”
“Desperate times call for desperate measures, Prasang,” I said. I rubbed over his tattooed back and moved my finger soothingly in his hole. “We need to get you hard and my best efforts aren’t working. We’re going to have to do something extreme.”
Eyeing the mutant plantain in Gary’s hand, Prasang started trembling all over. He was having an actual physical reaction to his fear of this thing. I couldn’t entirely blame him.
“What’s wrong, Prasang?” I slid my finger out of him, stood up and wrapped my arms around his chest. I rested my chin on his shoulder. The warmth of his quivering body felt good in the cool night air. “Tell me. Talk to your master. Why are you so scared right now?”
His chest heaved beneath me. I could sense the tears coming again. “Please…please, don’t put that inside me, master. It-it’s so big, sir. I’ll get hard for you. I’ll come big for you. Please…”
“But Prasang,” I said, reaching down and stroking his cock, which was falling more and more limp by the second, “You said before you couldn’t come again, remember? And I tried to help you but you still couldn’t get hard…”
I caressed his cock sympathetically as he trembled. His teeth started to chatter against each other. “You see, Prasang, you can’t even do it now. But I want you to get hard and you want to do whatever please your master, don’t you?”
His tears came for the second time. “Please don’t, master,” he wept, “Please, don’t put that in me…”
I wiped his hot tears with my thumb, then inserted it into his mouth. “Suck on this nice and slowly, Prasang.” He did as I said, sucking tenderly even as new tears rolled down his face.
“Remember our agreement, Prasang?” I said into his ear. I flicked one of the clothespins in his left nipple upward a few times. “Remember what you told me? You said you’d submit completely to my will, to anything I would ask you to do, no matter what it was. Remember that?”
He did not respond, only continued to suck miserably at my thumb. He knew me well enough to know my mind was made up about this and his fate was sealed.
I wiped more tears from his face and had him suck them away. “Remember those two lines I taught you earlier? I want you to say them again now.”
I pulled my finger out so he could speak. He shook his head weakly.
“Say it, Prasang.”
“I’m a good boyfriend and my master is proud of me…”
“That’s right, Prasang. You’re a good boy. A very good boy and you make your master proud.” I gave him a kiss on the cheek where I had struck him earlier. “And the other line?”
“Please, master…”
“Say it!” I was growing impatient with his sulking now.
He drew air in his full breath and recited. “I don’t need to worry because my master is going to…to help me get hard and come.”
“That’s right, Prasang, you just leave it all to me. It’s not going to be as bad as you think. We won’t start with the banana, we’re going to work our way up to it, understand? You’ve already had two fingers inside of you and this banana is only three fingers at the most, so we’ll start with that.”
The banana/plantain was, without question, thicker than three fingers, but I didn’t want Prasang to know that. He’d find out soon enough.
I sat back down and applied oil to my index, middle, and ring fingers. I bunched the three of them together into a curved claw, emulating the shape of the fruit, and pressed them to his hole. “Deep breaths, Prasang. We’ve already got your anal muscles nice and loose so they’ll go in easier. Remember to push against me when I enter you.”
report Prasang started to breathe and my three oily fingers slid up into him.
The sensation was immediate and so intense that Prasang lifted his pelvis upward. “Ah…AH!”
“Keep your buns still, boy. What did I tell you? Go down, not up!”
He whimpered at my sudden show of anger and pushed his ass downward, taking my fingers in further.
“That’s it, Prasang. Sit on it. Take it all the way in. Good boy. Now bounce a little. Get used to the feeling of it inside you.”
Hands clenching tightly to the beach chairs and jaw locked in place, he began to move himself up and down, keeping his breathing steady. His oiled up anus felt wonderfully tight and smooth around my digits.
Now Martin decided to join in. “Here,” he said, taking the plantain from Gary. He weighed it in his hand, impressed. “Open your mouth, lad. It’ll seem easier if you have it in this end first.”
I remained silent. This would not have been my suggested route forward. There was the risk of it being too much for Prasang. However, I was not about to question Martin as he was now one of his masters, too, and could do with him what he wished.