Chapter 18: Clarence Takes the Cherry

(Clarence narrates)

I’d been putting off taking Hunter’s cherry. I don’t know why. I suppose it was still novel enough to be able to get blowjobs anytime I wanted and I knew fucking him would take our situation to the next level. Mr Keller had arranged the auction and now there were only a couple of days left. I knew it couldn’t be postponed and anyway the waiver from BondCo on Licker’s contract came to an end two days after the auction, so there was no room for further procrastination. If I wanted to be the first to fuck my former brother, and I really did, then I could delay no longer especially if I wanted to do it more than once before other people. I called him into dad’s (well mine now) office one afternoon. I could see it still got to him, me sitting behind the desk “Give yourself an enema and a shower and be back in five minutes.” I had no idea if that was possible, and I didn’t care.

When he got back, I ordered him to lie face-down over the desk.

I then used two handcuffs and two leg-irons to secure his limbs to the legs of the desk, immobilizing him, prone and spread wide. Besides a single birthmark, every inch of his skin was still smooth and flawless although his ass was a good red color as it was most of the time these days. He smelled fresh and clean. His ass was so clean you could eat out of it. I’d have loved to, in fact, but it was beneath me now to do that with a slave.

I wrapped two cushions in his football victory pennant and shoved them under his crotch so that his ass was sticking out at just the right height. He was freaking out now, knowing that I was gearing up to take his cherry.

“Permission to sp---” he started to say as I jammed the ball gag back in his mouth.

“Nothing you can say can change what’s about to happen to you. You’re trussed up nicely and looking like probably the best fuck I’ve ever had. I’m going to prepare you a little ... if I dry-fuck your virgin ass, it might make it hard to pimp you out at prime rates.” I was on his back, whispering into his ear, as I pushed a well-lubricated finger into his tight ass.

“Mmmphh...” he groaned through the gag.

“We’re just starting,” I continued, slowly shoving a second finger, then a third finger, as my helpless jock stud wiggled and squirmed against the invasion.

After stretching his ass with my fingers for a minute, I pulled out. I was glad his ass was so clean after the enema. Without further ado, I rammed my cock up his ass, causing the loudest moan of all.

“Like that, bitch?” I taunted him. “I’m so glad I’m going to have your ass on-call 24/7 around here from now on.”

His inexperience made it so he struggled against my onslaught, instead of relaxing to accept it. He was just clamping down on my dick, almost too hard. It was acting like a cock ring, keeping my dick hard but making it take longer to cum. At some point, he loosened up, maybe he remembered his training.

I was sweaty and exhausted by the time I came in his ass. It was so good. I almost decided to go another round, early wake-up be damned, but I knew I’d get to fuck him again tomorrow.

I pulled out and snapped a few photos to commemorate the occasion and grabbed a beer. I decided to leave him bound as eye-candy while I drank, but then I realized he could be useful for something. I unchained him and had him kneel. “How well did you clean yourself out with that enema?” I asked.

“Pretty well,” he said, not entirely convincingly. “Master”

“I guess you’re about to find out...” I pushed his mouth onto my dick, which was starting to get stiff again. “Clean it!” Actually, his ass was pretty clean, I think, and the mouth-cleaning polished my dick to a satisfactory level.

I released him and took him down to his room. I had decided I wanted him to have my spunk on him all night and to wake up with it in the morning as a reminder of what had happened so I was worried that the stuff was already beginning to leak from his ass.

At first I thought I would reuse the diaper he had used on his first night {Who cares if he gets diaper rash?}But then I realized it could impact the upcoming tomorrow. I sighed, realizing I had to find another approach. I again turned to the Slave Processing Center gift bag. I found a small butt-plug in there that I figured would prevent any leakage.

As we left the office, I told him that the plug was to stay in his ass until after breakfast and if the twins asked him why he was wearing it he was to tell them what I had done for him. Also when we got to his room I would give him an opportunity to thank me for fucking him and he better make it good if he didn’t want a ton of demerits. I made him kneel on the floor and unbuckled his gag.