Dylan's Wager

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.

Not fighting the flow turned out to be a good decision. I don't know if Dylan intended the shave to be the erotic experience it was, but it was better than most blowjobs I'd had up to that point of my life. Her strokes had just the right pressure. Her free hand held my cock right where I held it when stroking myself just a few minutes earlier. My skin was sensitized in places that didn't seem erogenous before. I was close to coming several times. Dylan seemed to know this and changed her technique to keep that from happening. It was a blissful five minutes.

My blindfold was still firmly in place but that didn't stop me from seeing some very vivid pictures of what happened next. After cleaning of the last bits of shaving cream, Dylan went down on me and gave me the blowjob of my life. It started with small kisses on the newly shaved skin around the base of my cock. Even her warm breath created sensations I had never felt before. I could imagine her head hovering over me. I thought about that red hair.

Her lips found their way to my balls where every little touch caused my body to jump with pleasure. My cock was rock hard and in serious need of attention. Dylan chose to linger below switching from kisses to long, wet licks. Her tongue started underneath my balls then all the way around to the base of my shaft. I'd never felt so many sensations because I'd never had so much skin exposed at one time. Each of Dylan's licks made my sac hotter. It felt like she was pushing my cum right into my cock. I'd managed to stay fairly quiet until now, but I couldn't hold back the moans of pleasure. I was about to explode.

As with the shave, Dylan seemed to know when to switch things up to keep me from coming. Her licks moved to the freshly shaved skin above my cock. It felt great, but it also cooled me off a bit. Eventually, her mouth made it to my shaft. She didn't engulf my cock at first. Instead, she ran her lips and tongue along all the places I didn't touch when stroking myself. She expertly kept me hard while avoiding my hot zones.

That drove me crazy and I tried to shift my hips to get my cock in her mouth. That was a moving target, however, and there was no way to hit it with limited sight and mobility. Dylan paused from her licking to remind me that my efforts were futile, that she was in control, and that I'd come when she wanted me to come.

To make her point, Dylan took most of my cock in her mouth and started sucking it with long, slow slurps. Every bit of it felt great even though she was teasing me by not letting her tongue touch my most sensitive parts. She could have done this all day and kept me hard with out letting me come. It was maddening and I wouldn't have traded it for anything.

Finally, Dylan started attacking my rod like she wanted me to blow my load. Her tongue found its target on the underside of my shaft with every lick. It swirled around my bulging head causing me to once again get rock hard. She sucked at the tip as if she was trying to siphon out all of the cum she had pushed to the base of my shaft. My moans became more uncontrollable. My hips were straining towards her mouth. I shouted out that I was about to come.

"I know," she said, breaking the spell of the moment. "Thick and purple. And I really like how hard you get."

I felt her move away from me. I let out a frustrated gasp and yanked my arms hard hoping to release the restraints. No luck.

"You're not going anywhere quite yet boss," Dylan said with a smile in her voice. "The night is still young. I really liked shaving you and sucking you. From the looks of it, you liked it too. But now it's all about me."

Dylan straddled my chest. I could feel her bare legs squeeze me tight. She reached down and removed my blindfold. I found myself staring at her perfectly shaved pussy.

She giggled. "We match."

Then she ran her fingers between her legs. "I'm very wet. See?"

Dylan's fingers glistened with her juices. She placed them on my lips and then in my mouth. All this teasing was getting to be too much. The taste and scent of her made me want to fuck her hard. I tried to push my hips towards her to get her interested in sitting on my cock. She repeated that this was her time now and picked up a small vibrator she had placed on the bed.

All I could do was watch as Dylan flicked the switch on her toy and started to rub it on her pussy. She made small circles with it, pausing every once in a while to let it sit in one spot. Sometimes she press is hard against her clit. Sometimes she'd let it dance lightly across her skin. From my vantage point, it looked like she was putting the same kind of tease on herself that she had put on me for the last 30 minutes of so.

I eventually managed to stop staring at the scene in from of me to actually look above Dylan's waist. She was wearing my blue-striped button down shirt and staring right back at me.

"I'm glad you like what you see," she said.

"It's beautiful," I replied.

"Well, your job right now is to tell me more about what you're thinking."

I told Dylan how I wanted to go down on her, how I wanted to kiss her and lick her and get my tongue deep inside her. The more I talked, the faster the vibrator moved around her clit. Her breathing became more rapid. The vibrator finally found her hot spot and she held it in place and humped it. A long, low-pitched "oooooh" signaled she was starting to come. I told her I wanted to taste her and she obliged by wetting her fingers and putting them in my mouth.

I knew the first wave hit her when she gasped and placed her free hand on my chest, pushing down firmly to brace herself. "Oh god, I'm coming. I'm coming so hard. It's so big. Ooooohhhh. So big."

Dylan moaned and bucked. I felt her juices drip down on to my chest. She dropped the vibrator on the floor so her second hand would be free to hold her up. She had several full body spasms. After the third or fourth, and without missing a beat, she slid down past my hips and guided my cock into her pussy.

I felt like I was on fire. Dylan was not only wet, she was tight and hot. She rode me hard and came at least once more within a matter of seconds. She was fucking me, or should I say fucking my cock, has hard and as fast as she could. There was no kissing, no touching, no hugging. It really was all about her at that moment, though I had nothing to complain about.

I tired to hold my hips firm to give Dylan something to push off from. Her juices started to run down my balls. That felt great on my shaved skin. She started her low moan again. She was going to come a third time. I felt Dylan's hand reach behind her. She found my balls and touched them the way I did when she was watching me earlier in the evening.

"Come in me," she ordered. "Empty yourself into me now."

I tried to resist, thinking it was my one opportunity to have some control of this episode. I didn't have a chance. Dylan knew what she was doing, putting me on edge all evening. It was not my night for deciding what happened and when. Wave after wave of cum exploded from my cock. My pulsing and my moans triggered her last big orgasm. She again placed both hand on my chest to brace herself. It took a minute or two of moaning and writhing before she found some rhythm to her breathing.

Dylan placed her head on my chest. My cock stayed firmly inside her. She rocked up and down slightly and asked if I liked the evening. I told her I did. She asked what I'd like to do next. I told her I wanted to come in her hair.

Dylan lifted her head and grinned.

"That would take winning a substantial bet," she laughed.

Game on.