I put my clothes on and kissed Karen goodbye before heading to my own room to shower and dress for the conference. An hour later we met up in the hotel restaurant, both of us in now our best business attire, and sat down to have a good breakfast before the full day’s work ahead of us.
When we finished eating I told Karen I was going to use the restroom before we headed out and stood up. “Hold on Jack,” she said, “I have something for you.” I walked around to her side of the table she as reached into her purse and pulled out a handful of small but very wide rubber bands, each probably just a little over an inch in diameter but maybe 3/8ths of an inch wide. She motioned for me to bend down so that she could speak quietly into my ear.
“These were holding bunches of those pens with our logo that we had made for the show,” she said. “Would you do something for me Jack?”
“Of course,” I replied.
“Could you take these into the men’s room with you,” she said, pressing them into my hand, “and put them on your cock? I think you could probably fit three or four of them on.”
I pocketed them and headed off to the restroom. Once there I entered a stall, and after relieving myself I left my cock out as I retrieved the rubber bands from my pocket. They were brightly colored in yellow, blue, green and pink, and I began fitting them over my flaccid penis.
I was able to fit four of them on so that my entire shaft was covered up to the head — I’m circumcised — and the only tricky part was getting them on so that none of my pubic hair was caught underneath them. I put my cock back into my briefs and returned to our table.
Karen looked at me and asked with her eyes if I had completed my task.
“Done,” I said.
“I’d like it if you wore those all day Jack, that way I know you’ll be thinking of me.”
“All day? Even during the presentation we’ll be doing later?”
“Especially during the presentation,” she said, grinning. “We better get going now.”
Ever the gentleman, I held her chair as she stood up. We walked out of the hotel and made our way to the shuttle buses ferrying conference attendees over to the Convention Center. As we boarded the next bus leaving, Karen said, “Let’s sit in the back.”
We made our way to back of the half-full bus and sat down in the back. Karen turned to me and quietly asked, “How do they feel on you, Jack?”
“A little strange,” I replied.
“Are they uncomfortable?”
“Not really. I definitely know they’re there, but they wouldn’t be uncomfortable unless I, you know… got excited.”
I should have realized what was going to happen the moment those words left my mouth.
“Let’s see,” Karen said, discreetly slipping a hand under the messenger bag that lay across my lap and quickly locating my cock. She began teasing it through the thin fabric of my dress slacks, and it didn’t take long for me to respond.
“How are they feeling now?”
“Not good… they’re squeezing me pretty tightly.”
“Mmm,” she said, whispering in my ear, “it turns me on to know that. I’m sorry to have to tell you that your cock is in for a much harder time later on.”
“A harder time?” I asked, sarcastically.
“No pun intended,” she said, giving it a sharp squeeze that made me wince.
She continued to discreetly play with me until our bus pulled up to the Convention Center, and although the rubber bands felt quite unpleasant I was thankful they kept my cock in check well enough that I didn’t have to worry about standing up to leave the bus.
The doors opened a few minutes later and we filed in, found our display booth and started setting it up for a day’s work.
It was a crowded conference and we were both kept busy speaking to the stream of attendees stopping by our booth, discussing our products, handing out brochures and exchanging business cards.
Occasionally I would look over at Karen and marvel how this charming and professional-looking woman, her hair neatly tied back and wearing a crisp navy blue business suit, had only last night driven herself into a sexual frenzy by whipping me until I cried. Even more amazing was knowing that she had every intention of doing it again, and might even now be thinking about other ways to use me.
I watched the men and women engaged in conversation with her, musing on what they would think if they could have seen her unleash the fantasies she had been nurturing for years. Of course I also couldn’t help wondering what they would think of seeing me, a polished and well-dressed businessman, naked and bound to the back of a chair while being whipped to tears.
The morning passed into afternoon and the time arrived for our company presentation. Karen and I stood in the wings of the small auditorium stage as we were introduced, and as we waited her hand moved to the front of my slacks and her fingers found my cock. Once more I was thankful for the rubber bands keeping my erection down even though I was again being uncomfortably squeezed as we walked out on stage.
Our presentation went very well. Karen and I were both good speakers; we had prepared well and our slides were engaging, and we believed in our new product line enough to evangelize it convincingly. We finished on time and spent the next hour chatting with the attendees who wanted to meet us and learn more about our company, or pitch their own services — the usual networking stuff.
Finally the day came to a close and the end of the conference. We packed up all of our materials and now had the evening ahead of us, as our company was generously allowing us to spend another night in Las Vegas and fly back the following day.