I was on the bed, flat on my back. Dylan kissed my ear and then my neck. Her lips ran from my neck to my shoulder, grazing my skin along the way. From there, a passionate series of kisses down my chest. Her tongue flicked across my nipple and she paused to nibble and suck on it before moving on. I didn't move.
I couldn't move because I was tied down to the bed. Oh, there was a little slack, just enough to give me the sense that I could move. I could raise my head and shoulders up a little bit but I couldn't take control of the situation. It was a first for me, being tied down by all fours. Dylan knew that and was milking the moment.
She kissed her way down my chest, looking up and locking eyes with me as she passed my very hard cock and settled in on my inner thighs. Her kisses were getting wetter by the moment and every so briefly the tip of her tongue would find my balls or her short red hair would brush against my cock sending a shock wave and down my body.
My instinct was to grab Dylan's hair and shove my cock in her mouth. My restraints kept me from doing so. Instead, I just looked at my cock contrasted against that hair. It was a fairly bright red. Her hair, that is. It was originally brown, but Dylan had it cut short and dyed red. It was an impressive styling, echoing a punk/new wave look but reserved enough to work in mainstream America. I wanted to come in it.
Dylan stopped kissing me right about the time I was thinking she'd start working on my cock. She slid off the bed, walked over to the nightstand, and pulled out a scarf. A minute later, I was blindfolded and listening to her footsteps leave the room. She called out, "Be back in a minute boss."
I didn't hire Dylan with any expectation of sex. My sex life was pretty good at the time and I didn't need boss-employee sex dynamics in my business, especially since Dylan was my first and only employee. Fact is, I hadn't planned on hiring anyone at all, but business in our market was better than ever and I was tired of watching opportunities pass me by.
Dylan worked for a client of mine but was going nowhere in her job. I offered her work under the condition that she would help me generate new business. That ended up being the core of our little bet. A bet that eventually landed me in my current situation.
There are three things I've learned about Dylan since hiring her. First, there's no stopping her when she sets out to do something. Second, she won't make a bet she can possibly lose. Third, and this should be obvious by now; she likes to be in control.
Dylan was good with the numbers but she had a lot to learn about the working with clients so we initially traveled together more than expected. I enjoyed her company and was attracted to her with each passing trip. I tried not to dwell on it but I also wondered if she was feeling the same. We actually worked well together, however I could tell that something was beginning to bother her. I asked her about it over dinner one evening and in her words the issue was, "they treat me like a trainee when you're in the room."
"How do we fix that," I asked?
"Let me be in charge."
We talked about the accountability that goes with leading a client project. We talked about the importance of setting up the next sale through excellent service. I told her how learning to do these things took time, experience, and the ability to weather the tough moments, like the ones she was experiencing at the time. Dylan told me she could deliver on all counts if I just trusted her to be in charge. I tried to find the words to say "not now" without letting her down. She upped the stakes before I spoke.
"Look," she said, "I can read the signs. I know you want to say "no" to this but I can do it and I'm willing to wager a night in bed on it."
"Wait a minute," I protested. "I don't.... you... don't..."
I was completely flustered. Yes, I was attracted to her but I didn't want her thinking that her career in my company hinged on sleeping with the boss.
Dylan continued. "It's just you and me here and we can't ignore the fact that we're attracted to one another. I've wanted to pounce you on more than one occasion and I can feel something coming from you too." At this point I was thinking about trying to breathe and not saying anything until I was certain she was done talking.
She had more to say. "Here's my proposal. You give me the lead on the Tampa account and I'll get them to renew for another year before we finish our presentation. If I don't, I'm yours for the night. If I get the renewal, you're mine for the night. One night only. No strings attached."
"So, I win and I'm in charge, you win you're in charge," I asked?
"Deal," she said.
To make the long story short, we went to Tampa, Dylan had the lead, the client was impressed, she asked for the order, and they renewed on the spot. Dylan had set her goal, done her homework, and won.
We celebrated over dinner, she reminded me of our bet, and I followed her to her hotel room. No sooner did the door close and Dylan was giving orders. Kiss her. Fix her a drink from the mini-bar. Stand in the middle of the room and get undressed. She was enjoying her control and how it clearly made me feel awkward.
There was only one thing out of her control at that particular moment. She started to command me to stroke my cock to make it hard, but that wasn't necessary. Dylan got out of her chair and came over to inspect her prize. She looked but did not touch. She told me to stroke my dick the way I would if I were trying to get off. She had me touch my balls. She had me pull the skin as tight as possible so she could see how much the head of my cock would swell. She was doing her homework, figuring out what made me feel good. That made me so hard I thought my skin was going to rip.
"Purple," Dylan said dryly as she looked at the bulging head of my cock. "And thick. I like purple and thick. You can lie down on the bed now."
"You sure you wouldn't rather have a performance bonus instead," I asked?
"We'll both make good money working together," Dylan replied. "Tonight my bonus is having my way with you."
I'll give her credit. She was determined, focused, and prepared. She had but a half-hour before the client meeting to drop off her suitcase. In that time she managed to get some sort of straps and cuffs attached to the bed that I didn't notice when I came in the room. And she either turned the bed down herself, or the housekeeper had a good chuckle when performing the service earlier in the evening.
My back was barely on the sheets before Dylan was giving instructions to spread eagle. She began kissing me once I was securely fastened to the bed. Then came the blindfold. And then she left the room.
I didn't have to wait too long for her to come back. I heard her rustling around at the end of the bed and I heard the distinct sound of whip cream coming from a can. This will be fun, I thought, as I felt her spread the cream on balls and around my cock. I can live with being tied down while Dylan licks me clean. With any luck, I might even come in that bright red hair.
It was quite a shock when I felt the cold steel of a razor on my balls instead of a warm tongue. Before I could protest, Dylan ordered me to stay quiet. But I couldn't. I had my annual physical the following week. I didn't want to have to explain this. The problem was Dylan cut me off every time I tried to speak. I finally gave up when she pointed out that she was going to shave me whether I liked it or not and that being able to focus on the job was essential to an error-free outcome.
