Seven Days of Service - Day 03

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An offsite meeting; more boundaries explored
8.3k words
4.75
38.7k
18

Part 3 of the 7 part series

Updated 09/22/2022
Created 11/12/2014
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Hatsuda
Hatsuda
198 Followers

Seven Days of Service – Day One

Wednesday morning came early this week, and I was still dealing with the angst of having probably fucked up a perfectlyimperfectbondage scheme by trying to rush into it too fast. My hope at this point was that Cathy would simply blow off the incident, and allow me to change direction on our terms of service. After all, I still would love to have her continue cooking for me, and I could add cleaning and general housekeeping services into the mix to satisfy the service requirements.

Sitting at my desk, I sipped my coffee and reviewed the day's workload and was surprised to find it exceptionally light. After the stress and tensions of the past couple of days, I decided I'd take the afternoon off for a change, and get some laps in my swimming pool at home. The weather was perfect, I had cold brews in the fridge at home, and I could fall back and regroup on thisserviceissue.

I was scanning the last couple of reports when my office door opened. Looking up, I was surprised to see Cathy turn and lock the door, then walk to the front of my desk. Looking at the wall, I saw that it was already 10:00 a.m., and looking back at her noted that the collar was still attached to her neck.

Remaining in front of my desk to display her obedience to my instructions, she locked her eyes directly onto mine, unbuttoning her blouse to reveal that she was still quite bare, something my cock was quick to pick up on. This time, leaving her breasts bare, she reached down and pulled up the hem of her skirt, revealing that she had not worn any undergarments either.

Before she could cover back up and leave, I decided to see if I could push her threshold of comfort a bit more, and motioned her to come around the desk next to me. After a moment's hesitation, she dropped the hem of her skirt, slowly walked around and stopped, just out of my reach.

I motioned to her to raise her skirt once more. Still watching my face, she did so. Her pussy was almost directly in my face, and I couldn't help but notice that there was already a substantial amount of moisture evident on her labia and even showing on the sides of her inner thighs. The faint aroma of her arousal was already sending powerful messages to my libido, causing my cock to push out against my trousers even harder.

Again, I made no pretense of trying to hide my own excitement; instead I sat there with my legs apart, hands on my thighs, watching her stare at my erection.

To keep her a bit off balance, I reached out with my right hand and combed my fingers through her pubic hair. As I continued to scratch my way around her mons, I could feel the heat emanating from her pussy, and my fingers continued to collect the wonderful moisture produced by her arousal. Finally, I dipped my fingers directly into her cunt, sliding them deep within her body.

I felt rather than heard her gasp, and as I looked up into her face I saw that her eyes were closed and she was biting her lips. She held her arms stiffly by her sides, and her hands were clenched. But, this was neither the time nor the place for play, so I withdrew my fingers from her body and pushed her back away from my chair. Getting up, I looked down on her standing before me, and told her to open her mouth.

Puzzled, she wrinkled her brow at me, but did as I asked. I then took my fingers and inserted them into her lovely mouth, and instructed her to clean them for me. Her puzzled look quickly turned into a frown, and I could see that she was weighing her response very carefully. After an awkward pause, I felt her tongue gently licking her fluids from my fingers. As she did so, she dropped the hem of her dress and began to button up her blouse. Once she'd finished covering herself up again, she took hold of my wrist, and worked her tongue across the last of my fingers, and stepped back. I saw a bit of defiance in her face.

After last night I thought our little game was over, and that was why I challenged her to a little sexual humiliation this morning. Certainly what we'd done last night was much worse than what I'd directed her to do just now. As she stood before me, waiting for instructions I asked her, "Were you all right with our 'sensitivity training session' last night?"

She dropped her eyes to the floor, and said very softly, "Yes . . . Sir."

Wondering about how the session ended, I asked her, "Why were you so upset just before you left my house? You were crying."

Still looking at the floor she paused, thinking—then replied, "I was shocked and ashamed at what I'd done in front of you. I'd never lost control like that in front of anyone before. How could I have not only climaxed in front of you, but begged you to make it happen?"

"And yet you are here this morning?" I said. "Why?"

"The contest, I think. I don't really know," she responded. "I've never come up against this kind of situation before, and I'm a little confused. I need to find out what's happening to me."

"Well, for the purposes of this 'deal,' you ARE to provide services to me, services that haven't really been defined, right?" She slowly nodded her head. "Did I harm you in any way?" She shook her head in the negative. "So, for all intents and purposes, you belong to whom, at least for the extent of this contest?" I asked.

She thought about that for a few moments, then squinted her eyes and said, "You?"

I smiled at her, "Only four days left, Cathy. Then you can return to what you were before you lost this contest. A few more days of 'sensitivity training' and you can embrace it, or fall back into what you were."

As I finished saying that, I casually reached over to her with my left hand, and lifted the hem of her dress. With my right, I reached between her legs, and into her sex, dragging my hand slowly through her pussy lips. She trembled at my touch, but didn't move away.

Bringing my hand back out from under her skirt, I raised it in front of my face–in fact between our faces. She assumed that I'd make her clean my hand off again in her mouth, and half-opened her lips, but I slipped my fingers into my own mouth, licking the evidence of her arousal from them with obvious pleasure. As I noted her reaction, I smiled and told her, "Don't be so greedy, m'dear."

Shaken, Cathy struggled to regain her composure. As she slowly brought herself back under control, I told her that we were about to take a sabbatical from our Deal this afternoon at my house, starting at noon, and we'd re-evaluate our relationship up to this point. Since I was in charge of this project, I didn't have to worry about prior obligations on her part. "Noon," I told her, "wear something nice this time because we might go out this evening, and don't be late."

I'd already planned on picking up a stack of frozen burgers and some deli potato salad in advance of my decision to take the afternoon off, so there was little preparation for a meal remaining. All I had to do was fire up the grill and I was on my way. Now that I had company, I had to figure out where to go from there. I figured that I might do the cooking for the afternoon outside on the patio, and maybe I could take Cathy to the Harbor Bar in the evening to meet old Hattie.

Wade had approved of my plan to put our heads together on business out of the office, especially since I'd told him that it would take something like that to create a little bonding between Cathy and myself. After the little flare-up yesterday in his office, he was more than willing to go along with any plan that would reduce his stress level in the departments. I had a little different idea of the bonding I wanted to happen between Cathy and myself, but I spared him the details.

My work was already finished by 10:30 a.m., so I left the office to pick up the supplies for lunch, and to prepare the patio for our afternoon off. I changed into my swimsuit, eager to get in a few laps in the pool before Cathy showed up. That pool was the major reason I'd managed to keep my shape over the past few years, that and regular visits to my club's squash court.

Taking long strokes in the pool, I felt the satisfying stretch of my shoulder and leg muscles as I ploughed through the water, back and forth. All this time I was trying to mentally assemble some sort of sensitivity exercise that I could put Cathy through today, one that would advance my mission of teaching her a bit of humility in her treatment of coworkers, and at the same time to satisfy my own curiosity as to how far I could loosen her inhibitions.

Caught up in my own musings as I lapped back and forth in the pool, I suddenly struck upon an idea that I thought might test the next physical boundary with Cathy, with little risk to myself. Just then, I caught the sound of my backyard speaker announcing someone at the front door. Hopping out of the pool, I grabbed a towel from the patio chair and made my way through the backyard gate to the front of the house.

Spotting Cathy at the front door, impatiently tapping her foot on the steps, I got her attention and motioned her to follow me into the back yard. She was dressed in her "dowdies," but was carrying a small travel suitcase, which I presumed contained her evening wear.

My neighbors are not particularly close to me in this hidden cul-de-sac, but the builders had settled on an 8-foot privacy fence around my back yard none-the-less, which pretty much ensured that I'd be able to do most anything I wanted back here without the bother of prying eyes. As I watched Cathy examine the patio area closely, I'm sure the privacy assurance was on her mind as well, although it was difficult to tell whether she was comforted by it, or feared it.

I took her suitcase from her and placed it just inside the sliding doors going into the back of the house, then indicated to her that she should remove the clothing that she had on. Shaking her head, she slowly removed her sweatshirt, and dropped her jeans shortly thereafter. Putting her clothing on a wicker table nearby, I told her to remove her shoes as well, leaving her completely naked except for the collar around her neck. I was really going to miss this when the prize period ended.

Mother Nature was finally playing into my hands right now, because the day was becoming insufferably hot, with the sun blazing down on us. The pool area itself was screened in which help absorb some of the sunshine, but I suggested that we seek the small shaded section of the patio to situate ourselves in. I had taken the precaution to place two long, flat lounge chairs in that area for our use.

The grill was already set up, and I'd fired it up in anticipation for the burgers to come. I sent Cathy into the back room of the house to bring out the chips, dips and salads. As I placed the burgers on the fire, I helped her bring out the rest of the accoutrements for our quick lunch.

As we finished up, she reluctantly admitted that I'd put together a passable "man-meal," and then asked me if it were possible for her to get some time in my pool.

She had now begun to play into my plan, so I tried to keep the mood light by suggesting that since the sun was so hot today, it might be advisable for both of us to put on a little sunscreen for our own protection. As she lay back on the lounge chair, I got up to get the sunscreen container and the blindfold that I'd parked on the table next to us.

Telling her to stand, I got up and removed the collar from around her neck. As I did so, I noted a totally unexpected reaction from Cathy. As I removed the collar, she brought her hands up as if to stop me, a surprised look on her face. She glanced at me as though she'd done something wrong and was being punished for it. I quickly explained that I didn't want to get the collar stained with sunscreen lotion, nor did I think that the velvet would fare well in the pool. She nodded her head in understanding, but appeared visibly uncomfortable without the collar.

I then began to put the blindfold on her, and when she resisted in confusion, I explained to her that I was going to apply the lotion to her, and she in turn, was going to apply the lotion to me. That way, we'd be ensured that no spot was left unprotected. As far as the blindfold was concerned, well, that pleased me, and that was all she needed to know about it.

And, since I was cursed with an inevitable erection around her whenever she was naked, I could secretly hide my blasted lust from her long enough to proceed with my intended plan.

Instructing her to lay on her belly on the lounge chair, I positioned myself next to her on my knees. She had her arms under her face, and her legs were pulled tightly together giving me a little indication that she was a bit lacking in trust at the moment.

Since my intent was to break through her barriers quickly this afternoon, I grabbed her ankles and pulled her legs apart, dropping her feet on either side of the lounge chair. When she tried to bring her legs back together, I slapped her on the ass one time, startling her into a quick submission.

Once she'd gotten used to the idea that I was back in control, she allowed me to place her delicious body parts wherever I wanted. My view at the moment was directly on her ass, and my own body was reacting as expected. Now that I had applied the blindfold to her face, all she could do was guess what I was going to do and I thought that would work in my favor.

"Slow and easy," I recalled.

Pouring sunscreen in the palm of my hand, I allowed it to warm before I began applying it to her foot and ankle. She flinched at my touch, but as I began massaging the lotion into her skin, she relaxed once more. Slowly I took her foot and worked my way up her calf to her knee, gently kneading it into her skin. Aside from the sounds of nature around us, and the bubbling of the pool pump, everything was quiet, almost meditative.

I thought back to last week, when we were still adversaries, and marveled at the changes that had overtaken Cathy. Me too, I suppose. I couldn't imagine myself ever being the same again after this week. As I'd discovered surprises in Cathy, I'd discovered some in myself as well. I didn't want this to go away, but I knew that my efforts to come to grips with this new set of feelings extended through Sunday, then back to the grind.

Taking her other foot, I repeated my application of sunscreen to it as well. I was pleased to hear a soft groan of pleasure from her as I gently worked the lotion into her skin. This was an exercise well suited for meditation, I thought.

I wasn't sure whether she knew how exposed she was to me, but as I glanced up her legs I saw clearly the lips of her sex, damp with the pleasures that she was experiencing right now. My reaction was predictable, erection desperately trying to escape the confines of my trunks. I knew where I wanted this to go, but I was unsure how the test would work out.

Finishing off her calves, I moved up to her thighs; cautiously, I began applying sunscreen to her thighs, gently massaging her muscles, but moving up gradually until I reached the bottom of her ass cheeks. Once I arrived at that point, she clenched her butt tightly, intending no doubt to keep me from reaching my ultimate goal.

I slapped her on the ass to remind her that I was still in charge, and she relaxed her butt. I moved on to her other thigh, giving it the same treatment that I'd given her right leg. This time when I reached the bottom of her ass, she remained relaxed. I stayed there for a moment, and then moved up to her shoulders, trying to shake her focus up a bit.

She fidgeted, but relaxed once more when I began applying the sunscreen to her neck and shoulders. Moving down her shoulder blades, I took full advantage of my position to run my hands up the sides of her ribcage, brushing the swell of her tits with my fingertips. I slowly worked my way back down to her ass cheeks, which I began massaging from the bottoms up, gently drawing them apart. Feeling what I was doing, Cathy tried to clench her butt cheeks together, but a quick swat from my hand on her ass reminded her that I was still in charge.

Looking into her delightful crevice, I saw that her pussy lips had become a bit reddened and swollen, and her juices were spread abundantly around her entire crotch, including her little asshole. Curious, I allowed one of my hands to briefly rub over her little tan anus, and she quickly clenched her butt cheeks once more. Reflex again, I decided as she just as quickly relaxed herself again. I had other plans for this afternoon however, so I told her to roll over so I could grease her up on the front side.

Probably relieved to change my direction after the narrow escape with her lovely butt, she carefully felt her way around onto the lounge chair, and lay on her back. She had placed her hands protectively over her cunt, but I instructed her to place them behind her head instead. I watched her reaction carefully now, as she slowly complied with my order, leaving herself wide open and potentially helpless to my touch. I was hoping that her experience using the "safe" word last night would give her the confidence to continue.

She took a deep breath and her body seemed to relax, so I began the first part of my little sensitivity training session; hoping for much more of course.

While my instincts were screaming for me to stop beating around the bush and just fuck the crap out of her, my own "safety valve" in this whole exercise was simply to get her to beg me for it. Once she did that, I could forget most any threat of lawsuit against me or the company for improprieties, and give me an opportunity to expand the boundaries of this service period. I was beginning to enjoy my role in this little "game" a bit too much, I thought. What would I do once the service period was up?

Taking her ankles in my hands, I gently spread her legs until her feet hung over each side of the lounge chair as they did when she was on her stomach. Her resistance to this was a bit less than before, but I noted that for later. I was now able to see my ultimate goal completely, although she was probably trying to visualize how much she was actually exposing to me while blindfolded. My blood was pounding in my head and in my groin, as I slowly began rubbing the sunscreen into her feet; first one, then the other working my way up her shins to her knees, and pausing for a moment or two while replenishing the lotion.

During that time, I noted with pleasure that her pussy lips continued to collect moisture and to actually begin to open slightly, very much like flower petals. The effect on me was predictable, and I had to readjust myself continually as I began to slide my hands up her thighs spreading the lotion evenly across her skin. The combination of the scent of the sunscreen and her arousal was intoxicating.

As I got closer to her sex, she began to bring her knees together, but I gently pressed them apart once more. She seemed less resistant to me now, showing more of a token modesty than any serious attempt to evade my hands. I wondered if today would be the day when she finally surrendered herself to me completely.

Once I reached the top of her thighs, very close to her pussy, I stopped. Taking more of the sunscreen in hand, I moved up to the top of her torso, and began to apply it to her neck and shoulders, leaving her squirming a bit in frustration. She'd apparently thought that I was going straight for the "Home Run" and had mentally prepared for that assault. It would surely happen, but when I chose, not her.

I carefully applied the lotion to her lovely tits, paying particular attention to her sensitive nipples, rolling them around between my fingers. Her moans were getting a bit choppy as I obviously found areas of greater sensitivity than others. It was clear to me that her breasts were strong erogenous areas on this young lady, and accordingly, I paid them the extra attention they deserved.

Hatsuda
Hatsuda
198 Followers