Top Dog

“No.” I spanked her ass hard, and she whimpered. “Do not clench. Relax for me. I’ll tell you when it’s okay to clench. Do you understand?”

“Yes, sir.”

“Good girl. This is all for your pleasure, Carrie. You’ll see.” She nodded, and I wondered if she was on the verge of tears. “Speak to me, audible answers only.”

“Yes, sir.” Her voice was near breaking, and I shook my head, not at her crying, but that she didn’t trust me.

I slipped my finger inside, and she fought against clenching the best she could. “Now you can clench with it inside. It’s not so bad is it?”

“No, sir. It feels fine.”

“Good, now let me get something that’s going to help you even more.” I pulled away from her and reached into the little drawer beside the bed and pulled out the smallest anal plug that I owned. I kept a selection of new toys for each lady, and when their time was done, they could bring them home, including the life-size dildo that I’d had made from a mold of my cock.

Her eyes widened as she saw what I had. “You’re going to put that inside me?”

“It’s perfectly safe. I want to fuck you with it in, and then I want you to wear it a while.” She nodded her head again, and I cleared my throat.

“Yes, sir.”

“Good girl.” I released one had from the cuffs so she could roll onto her back, but left the other secured to the bed frame. I lubed up the plug and slipped it inside her tight hole, and when I brought her up to my hips, she moaned. “See, it won’t hurt. I won’t do anything to hurt you, Carrie.”

“Thank you, Chance.”

Hearing my name on her lips, I centered my cock and thrust deep inside her. She cried out, but only with pleasure and then she was moaning and panting again, like my greedy little slut.

She dug her nails into my flesh as she came, her pussy clenching my shaft so tight it had me coming too. I soaked her depths and fucked her steadily until the last bit of my seed spilled into her.

As we lay there, each one trying to gain control of our breathing, she ran her fingers across the angry welts on my back where she’d marked me. “I’m so sorry, Chance.” She sat up, panicked. “I don’t know what came over me. I know it’s against the rules.” The contract strictly forbade either of us making marks on one another.

“It’s okay; I know how easy it is to get lost in the moment.” If it had been anyone else, I would have been angry, but with her, it was all proving different, though a small punishment might be fun. “You’ll just have to make it up to me.”

“Yes, sir. I’m sorry.”

“Don’t be.” I kissed her lips. “I have to go down and take care of a few things. I want you to wear that plug for me for a while. I’ll tell you when you can take it out and no matter how much that little pussy of yours aches with need because of it, I don’t want you to touch yourself. Let the need build. Are we clear?”

“Yes sir.”

I leaned over her and kissed her sweet mouth, releasing her other hand from the cuff.

“I’ll be in my study. It would be a great time to send a message to Rick to arrange a call home. I’ve called him earlier and instructed him to allow you to talk person to person through his connection.”

“Thank you.” She sat up with her excitement, easing onto one side as if not wanting the plug to hurt.

I planted another kiss and then headed down to my office. “You’re welcome.” It seemed I was breaking all my rules for her.

I called Nate to check on work and found him in a strangely happy mood. “Yep, everything is fine here,” he said with a bit of extra pep in his voice.

“You sound like you got laid.” The guy had no trouble finding hot women to bed, but that had become so common that it rarely affected his mood.

“Yeah, you could say that I might have found the one.”

What a coincidence, I wanted to say. I actually felt as though I’d found someone special too, even though I knew it would be ending too soon. And I wasn’t sure how she felt about me. I mean, I knew that she was more than satisfied sexually, but once she got her money, would she forget all about me? For the first time, the thought of that made me sick to my stomach. What the fuck was happening to me?

“That’s great, man. I can’t see you settling down, but if that’s what you decide, I wish you luck,” I say to Nate.

“So, how're things there in the pleasure pit? Is this one as feisty as the last?”

I’d told him about the temper the girl before had, and how she’d thrown one temper tantrum too many and it had gotten her tied up and fucked in every hole. I wasn’t out of my rights to punish, and she’d known it.