Page 44 of Bossy Mess


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It was a Friday afternoon and Sloane walked into my office. “Mr. Hartford,” she said, “I need to go over some of the paperwork for the Dyer property with you.”

That was code. She was asking if I had a few minutes to fool around.

“Yes, yes,” I said, “of course.” I straightened up the paperwork on my desk and moved a few things around. She closed the door.

We had it down to a science. She unbuttoned her shirt and ran into my arms, and we furiously began making out. Nothing had become routine with her. Every time we kissed; it was as exciting as the first time.

“I’ve been thinking,” she said, in between kisses. “We should put a ring on it.”

I was shocked. I had no idea that was even on the table and, even if it was, it was just so soon. But I suppose if we were married, it would mean we wouldn’t have to keep it a secret anymore.

But she laughed. She must have seen my expression.

“Not like that,” she said. “I mean, where’d you put the cock ring? I want to play with it on you.”

I hadn’t thought about that contraption since she brought it out of the box a few weeks earlier. But apparently, she had. And if it was so important to her that it was still on her mind, I’d at least humor her with it.

“It’s in my desk,” I said. “Let me grab it.”

I’d hidden it in the back of one of the drawers where nobody would find it. Like the boxes in the closet and their contents, I had no idea what I wanted to do with it long term, but I knew it was not professional to just keep it lying around in my office.

I handed her the rectangular box and she opened it, pulling the ring and remote out.

“Look what I brought,” she said and pulled a couple AAA batteries from the folder she was carrying. She pushed them into the remote and pressed a few buttons, cycling through the settings on the ring and watching it vibrate until she pressed the stop button and the vibration ceased.

“Beautiful,” she said, then placed the remote on my desk and unbuttoned my pants.

“The way this works, I’m going to need you to try and get soft. It’s a lot easier to put on that way.”

I closed my eyes and thought of the paperwork waiting for me in my desk — some of the filings that I still hadn’t gotten to — and that more or less did the trick.

“There we go,” she said. “Slides right on. And now is the fun part.”

She got down on her knees and took me into her mouth. Instantly, I became rock hard. She could work magic with her tongue, and I loved watching her do it. But it was only a tease. She took my cock out of her mouth and pulled on the ring. It wasn’t going anywhere. And, truthfully, it felt pretty good. I wasn’t sure why I’d resisted at all before. Especially since Sloane was so turned on that I could see her nipples poking out of her shirt.

“Now let’s see what it can do,” she said and sat on top of the desk, pulling her underwear out underneath her skirt.

I moved towards her when there was a knock at the door.

“Wesley? It’s Bob Isaacs, you got a minute?”

Balls! Bob was one of the board members.

“Just a second!” I called towards him, then whispered to Sloane. “Get it off.” And, knowing how she’d hear that, I clarified. “Get it off of me.”

She pulled on the ring, but as before, it wasn’t budging.

“It’s on tight,” she said. “As long as you’re hard, it’s not coming off.”

She slid her underwear back on and I closed my eyes, trying to think of anything else, but I remained solid. That erection refused to leave.

“It traps the blood up in the shaft,” she said. “It’s not going to get soft easily.”

“Thanks for the science lesson,” I told her. I tried pulling it off, but Sloane stopped me.

“Just be careful,” she said. “You don’t want to activate it if you aren’t ready.”

I gently touched it and tried loosening it from me, but all I was doing was stretching myself and making things harder. It was like a Chinese finger trap.

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