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=====CHAPTER 2=====
After Nadia and I ate, she packed up her things and left. I gave her instructions to keep everything quiet, and to not orgasm for the next few days. I reminded her that if she followed my instructions, she could be mine within a week.
I cleaned up a bit. At 8:00 I expected four knocks on the door but heard nothing. I wondered if maybe Bobby chickened out.
At 8:05 I heard four knocks. Marching over to the door, I opened it to see Bobby. He was on the shorter side, like he said, with short blonde hair. He was wearing nothing but a wifebeater, shorts, and a pair of sandals. I was surprised at how muscular he was, given his meek e-mails.
I put on an angry face at him.
“Take off your clothes and put them in the box on the ground.” He followed my demands to the letter. I locked the box and put it with my stuff. I told him to kneel and he did.
“You were 5 minutes late, Bobby.”
“I know, sir, I’m sorry. Traffic…” He began to say.
“I don’t want excuses, Bobby. I cannot have a slave who doesn’t do exactly as I say. Do you understand me?” I yelled.
Bobby nodded. “Yes, sir.”
I sighed and rubbed my forehead. “Ok, Bobby, today we’re going to be testing your obedience. You need to do exactly as I say without question. Understood?”
“Yes, sir.” He said slowly, looking down, already ashamed at his mistake.
“Stand up.”
He stood quickly, and put his hands behind his back, and looked at the ground. I inspected him, and prepared to ask the same questions as before. I pinched his left nipple and he took a quick breath inwards. I looked down to see his dick was already rock hard.
“I see you are enjoying this, Bobby.” I said. He nodded. He stepped around.
“How many times have you had sex, Bobby?” I asked.
“None.” Came the reply. I looked up, then circled back to look at his face, uncertain I had heard correctly.
“You’re a virgin?” I asked.
“Yes, Master. I haven’t had any sexual encounters before you, Sir.” He replied. I was surprised. This wasn’t expected.
“I assume you masturbate often?” I countered. He nodded. “How often?”
“Sometimes 10 times a day.” He said. I was impressed.
“Well, Bobby, one thing you should know is I prohibit masturbation. If you are to become my slave, that is one habit you will have to cease immediately. Your pleasure should take up none of my slaves’ time.” I explain. Bobby’s head drops. “Either you learn to take pleasure in the things I do to you, or you don’t orgasm at all.”
He looks up at me. “At all?”
I smile. “Don’t worry, You’ll learn to enjoy it.”
I meant it too. The key to keeping successful slaves is pleasure denial. It always keeps them wanting more, to keep trying to reach the elusive orgasm.
Yes, I allowed Nadia to orgasm just a couple hours earlier. But women are different, as they can achieve multiple orgasms and still remain wanting. Men experience a breakdown of sexual longing following a single orgasm.
So my plan for Bobby? Chastity. But he doesn’t know that yet.
“So you’ve never given a blowjob before?” I asked. Bobby shook his head.
I unzipped my fly and take out my dick. Now to see how he compares to Nadia.
“There’s a first time for everything.” I said.
Bobby leaned forward, and slowly but surely began to suck on my dick. He must have watched a lot of porn, because it looked amazing but felt lacking. It was crude, but that was to be expected for his first time.
“Now you’re going to deepthroat me.” I said. We both knew this was a bit much. Deepthroating, 30 seconds into his first blowjob of his life?
Yes, because that is what the job requires. I put my hands on the back of his head and press him towards his body. His throat at first rejects my dick, but then softens as Bobby gags, coughing and spitting all the way down until his chin reaches my testicles.
No, he’s not as good as Nadia in blowjobs, in fact his was rather weak. But what he succeeded on was saying on the dick. I held him there, gagging and coughing, for a good two minutes. I checked my watch.
“Keep going Bobby, you’re doing terrific. If you reach 5 minutes I’ll let you orgasm.” I said. Extra incentive.
The ground was damp with his spit and my precum, as Bobby forces himself to keep his face pressed against my body. What he lacks in skill he makes up for in determination.
Four minutes now. I guessed he might get close, and I have no intention of letting him orgasm tonight. So I take my fingers and close his nostrils. His eyes widen as his last way to breathe is blocked off. He gags some more, his throat undulating underneath the head of my penis.
“Just 30 seconds left, Bobby.” I encouraged.
Finally, he can take it no more. Tears are streaming down his cheeks, his saliva drooling out in a continuous stream, and he’s coughing and hacking on my dick. But yet he’s still on it, unable to breathe.
At 50 seconds, survival instinct kicks in and he throws my legs away with his muscular arms, gasping for breathe as my dick finally is removed from his throat.
I stand back and look at Bobby. He’s a crying, blubbering mess. But his dick remained hard.
“I’m so sorry, Master… I’m so sorry.” He said softly. He knew he made a mistake. And he knew he was going to pay for it.
I’m not going to repeat Nadia’s punishment for Bobby. Instead, I have something else planned.
“You failed me, Bobby, and a slave cannot fail his master.” I said. Bobby continues to cry.
I reach into my bag and pull out a few things.
“There is a way you can earn that orgasm back.” I told him. I have him stand up, and I push his hard dick out of the way as I tie a small noose around his balls. It’s attached to a small pail underneath.
I hold out some weights in a sack.
“Bobby, I want you to fill this with pail until there are 50 pounds of weight inside. If you do that you will be able to orgasm tonight.” I said. He nodded slowly, looking a little nervous.
He picked up a 2-pound weight from the sack and lays it in the pail. He grimaces.
“Only 48 to go.” I taunt.
He continued to put the weights in the pail, stretching his balls lower and lower, his face grimacing each time.
Finally, the last weight goes in. He’s screaming softly now, panting and crying again.
“Good job, Bobby.” I said. He smiles at my remark through the tears. I figure he’s had enough pain for today. I took off the noose from around his balls and told him to get down onto the bed. “It’s time to release some of that pressure.”
I told him he can jerk himself off right then and there. His dick was already rock hard. He started jerking and I watched him as he begins to pant. Already close, he got even closer to orgasm.
“Tell me when you are about to shoot, Bobby.” I ordered.
He is sweating up and down, breathing like a marathon runner.
“I’m close, Master, I’m close!”
I reach down, and in one calculated motion, pull his balls downwards cruelly. Bobby screams as his dick spurts semen all over himself.
I didn’t mean for him to orgasm, but it did, but it was a ruined one. Almost as good as not having an orgasm at all.
Bobby laid back on the bed, completely exhausted and pained.
I stand up over him.
“Our session is over, Bobby. But this coming weekend, I will come pick you up for an overnight session. Saturday night to Sunday morning.” I explain to him.
He looks up at me, and sighs. “What – what happens after that, Master?” He asks.
“Then, if all goes well, I will give you a contract to sign. If you decide to sign it, that will be the last decision you make. I will give you five days to end your previous life, and then you will come to live with me.” I told him.
“For how long?”
“However long you want. You can chose 3 years, 5 years… or lifetime.”
And with that, Bobby left. I was uncertain who I liked better. Nadia, the pain slut, or Bobby, the inexperienced virgin determined to serve.
I went home that night excited about coming events. What Bobby and Nadia didn’t know, is that I own that motel.
Perhaps a little backstory would be appropriate. I come from an incredibly wealthy family but as soon as I turned 18 and inherited my own personal fortune I cut ties with them. I had my own ideas. By age 25 I had my own company, my own fortune growing.
When I said Bobby would move in to live with me, I didn’t tell him that involved getting on a plane to rural Montana, where my 50 acre farm awaits them.
Did I intend on keeping my promise if they signed a 1,3, or 5-year contract instead of a lifetime one? Maybe. Only time will tell.
Friday night finally came, and I packed up a goodie bag to bring with me to the cabin. I dropped by the shelter to pick up Nadia. She came into the car wearing and jeans, carrying a backpack.
"What's in the backpack?", I inquired.
"Everything I own, Master," she replied. I was a little surprised, but shrugged and started the car.
It was an hour drive to the mountains, so when we got onto the highway, I turned to Nadia and said "Take off your clothes. All of them."
Nadia glanced around - I could see concern in her eyes.
"But what - what if someone sees me?", she asked.
I glared over at her.
"You need to follow my every command, Nadia! Without question! And on top of that, you neglected to address me as master!" I yelled.
Her concern was replaced by fear. Raw, primal fear.
"I'm so sorry, Master," She immediately stripped, and did not even hesitate at the panties. She sat buck naked next to me in the car.
"Now, I want you to throw your clothes out the window," I commanded.
She paused for a minute, then realized it. She rolled down the window and chucked her clothing out, onto the highway.
She rolled up the window and took a deep breath, her worry showing.
"You just screwed up, Nadia. Expect harsh punishment tonight."
NEXT CHAPTER: Nadia and Bobby's night in the cabin.
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