"Will, honey, will you make sure there's plenty of ice in the cooler?" Jenna called from the kitchen.
I checked my watch and saw that it was almost time for our guests to arrive. The New Year's Eve party had been Jenna's idea three years ago when we'd first moved in together, and it had evolved into a tradition. Jenna had spent the last two days cleaning and cooking in preparation for the party, and I had become her errand boy. I quickly checked the cooler of ice in the garage and came back in. I thought briefly about bringing the coolers into the mudroom, but decided against it.
The holidays had gone by without a hitch. We'd celebrated with Jenna's parents on Christmas Eve and sent them off the next morning to Jenna's brother's. Cindy and Jay were amazing people—I couldn't ask for better in-laws, but I was glad to see them go. It was no coincidence that the lingering pain in my ass disappeared the same day they left.
It had been over a week since I had seen my boss, Todd Barkley. The memory of that encounter hadn't faded at all in that time, despite my fervent wishing. Todd hadn't tried to contact me since that day, and I had taken all precautions to avoid him in public. I'd begun working out during peak hours at the gym, insuring that I would never be alone with my boss, should we be there at the same time.
After the ordeal in Todd's office, I had hoped that that would be the last we would see each other until after the New Year. Once the euphoria of the orgasm had worn off I remembered the office Christmas party that was supposed to be held that evening. The realization hit me just before Todd pushed the butt plug back into my raw and gaping hole.
"Gotta keep you nice and open for me, baby boy," Todd whispered. "There may not be time for foreplay later."
I shuddered hotly, and fought against the arousal raging through me.
That night, as I got dressed for the party, I'd been sorely tempted to remove the plug, but I knew I'd be punished and it would only make things worse.
At the party, Todd and I didn't cross paths for over an hour. I purposefully maneuvered myself and Jenna away from Todd as we mingled amongst my coworkers. After a couple of beers from the open bar, my vigilance slipped, and Todd managed to catch us.
"William, who is this beautiful goddess you have with you?" Todd asked with his confident charm.
"This is my fiancée, Jenna," I replied. "Jenna, my boss, Todd Barkley."
Todd and Jenna shook hands, and I suffered through small talk until we could make an escape. When I would have turned to leave, Todd clasped me on the shoulder and said to Jenna: "Forgive me, Jenna, but William and I need to discuss business for a moment."
Jenna nodded. "I understand. Find me when you're done, honey. I'm going to go talk to Brett and Sara."
Before I could protest, Jenna headed off to talk to my office buddy and his wife.
"Conference room," Todd murmured in my ear. He tugged on my elbow and, like a child, I followed, dreadful yearning boiling in my cock.
The room was dim, lit only by the lights coming from the surrounding area. The shades that provided privacy in the glass-walled room were shut, but still allowed glimmers of light to come through. As the conference room door closed, Todd smiled and said, "Your woman is very pretty. Does she let you in her ass?"
"Yes." I responded tightly. I wasn't sure if I feared was to come, or if I was looking forward to it. While my brain was conflicted, my cock twitched with anticipation.
The movement drew Todd's attention. "Looks like someone is eager for an encore." His smirk was visible even in the dim light of the room. "You've been avoiding me all night, sweet boy. It's time for you to pay for that."
I swallowed audibly, waiting for Todd to continue. Todd didn't speak, but began circling me like a vulture and his prey. The swat on my ass came swiftly and landed with a sharp sting that blossomed into heat. Another swat came down on the other side, and my channel clenched around the plug. I gasped a little, unable to help himself.
"That plug feels good, doesn't it baby boy?" Todd cooed, continuing to alternate swats across my muscular ass. Even through the fabric of my khakis, I could feel the pleasurable pain blooming across my ass.
I nodded, not trusting myself to speak. My moans were barely being contained, and I feared that opening my mouth would allow the collection to spill out into the room.
"Strip, William." The order was stern and I obeyed without hesitation.
Once I was naked, I went to my knees without being told. Todd smiled at the obedience, but the position was not what he had in mind. This time the slap on my ass was one of punishment, and not of pleasure, and I yelped in response.
"Lean over the table," Todd commanded, shoving me to my feet.
Quickly, I headed to the conference room table. It was a sturdy mahogany table, one that was primarily used for lucrative pitches. The run-of-the-mill pitches usually happened in a more casual, but still nicely appointed, conference room a few floors down. I felt exposed as I pressed my chest to the cool wood; more so than I had felt kneeling in Todd's office. I fought to keep my breathing easy, my cock hard as stone, as I waited for what Todd would do next.
"Beautiful boy," Todd murmured, running his fingers over my quivering flesh. He could still see the lingering pink from the earlier spanking, the flesh there hot to the touch. "Spread that ass for me."
I clutched my ass cheeks and spread myself, the feeling of vulnerability escalating.
"Baby boy takes his commands well. How does that plug feel in your tight ass, baby?" Todd asked as he pressed himself onto my back.
I dimly noted that Todd was now naked as well, and wondered how I had missed my boss stripping. Despite what my head told me, I was longing to see my boss naked—wanted to gobble his cock and suck it hard until cum shot down my throat.
"It...feels good, sir."
I felt Todd's hand gliding over mine on my ass and groaned against the grain of the wood. Then the plug twisted in my ass, sending sparks of pleasure shooting across my body. My cock twitched again, and I knew that pre-cum was waiting on the head.
"I could keep at this all night, sweet baby," Todd clutched my cock and began to stroke, "but we don't want precious Jenna starting a search party for you."
At the mention of my fiancée, I should have bucked my boss off me and left the room, but instead, I moaned, loving the feel of Todd's firm hand gliding over my cock. Todd ground his cock between my open ass cheeks, nudging the plug still lodged in my ass.
"I'm going to fuck you now baby. I'm going to fuck you until you beg me to let you come."
"Yes sir," I whispered as Todd tugged the plug out of my ass. I'd grown so accustomed to it that I instantly felt bereft without it.
