Hiring Cindy

Chapter 2 – Arrival

To my relief she arrived at my house the following Saturday with the signed contract in hand. She was wearing a cute, loose sun dress. I took the contract and signed it. I went and made a quick copy and gave it to her. I helped her carry her small bag into her room and said that I would leave her to unpack. I said that she would be making dinner for me that evening, and I wanted to eat at 8. I told her to wear one of the more conservative dinner dresses I had bought.

I went about my affairs as normal, leaving her to her own devices to start to adjust. At 8 I went into the dining room and she served dinner. She looked very cute in the dress she had chosen. We ate and talked and laughed, but she was clearly a little bit up tight waiting for the other shoe to drop. I had decided to take things very slowly indeed and to ease her into things. After dinner I told her that I was going to watch a movie I had rented, and she joined me, sitting on a separate chair. Afterwards, I said that I was going to bed and said goodnight. She looked a little surprised, but she was starting to be more at ease.

The next couple of days were relatively uneventful. She served me meals, spent time watching TV, reading, going for walks, etc. Sometimes together, sometimes separately. The only instructions I gave her were to prepare the meals, and what type of clothes to wear. I didn't ever tell her to wear anything overly revealing, sticking instead to the more conservative end of the spectrum. Certainly, however, being told what she was to wear was an adjustment for her, and seeing some of the other clothes in her closet must have made her think twice. I also had her do some light cleaning one of the days. I was getting very excited thinking about the power I had, and what an attractive woman I had at my beck and call, but I never did anything lewd.

On the fourth day I suggested we take a swim, and said that I would meet her by the pool. She showed up in one of the sexier bikinis I had bought. We swam and sunned. After a while I asked her to make me some snacks. She grabbed for the shirt she had worn over her swimsuit when she came out, and I told her she wouldn't need that. She looked a little bit surprised, but dropped it without a fuss. As she walked back into the house I turned around to check out her ass. She really had a stunning figure. I was starting to get quite a bulge in my swimsuit...

When she came back in, we ate and talked. After we were done I asked her to stand up in front of my chair. She tensed up, appearing to sense that things were finally shifting into a more serious gear, but she did as told. I looked her over, and she was visibly uncomfortable at the attention. Even though this wasn't the first time I had seen her like this, somehow it was more of a shock to her after she had relaxed into a more casual, friend-like role I think. Anyways, after a minute I asked her to turn around. She did, and then I asked her to bend forwards slightly. I could tell even from behind that she was embarrassed to be putting herself on show like this. I told her to arch her back a little. Her ass looked great pushed out like that.

After I had my eyeful I said "thanks, that is all" and said that I would see her at dinner.

She seemed relieved. I went back to my room and jerked off. I was trying very hard to restrain myself and not leap into things too quickly and scare her off. At dinner she was maybe a little tense, wondering what I would ask her to do next, but I didn't do anything.

Another week went by in similar fashion. We spent time getting to know each other, I asked her to wear one of the shorter dresses with stockings one night, and made her stand for me to look over, but nothing more exciting then that. One night, while we were watching TV, she cuddled up next to me. It was very comfortable and nice. She was falling into the girlfriend role very naturally. I almost think she was starting to legitimately have feelings for me.

Finally, I couldn't take it anymore and I decided to get things started in earnest. I started with something very simple. We were watching TV and she was cuddled up against me. I put my arm around her and pulled her closer. She looked up at me and I started kissing her. To my surprise, she participated in the kiss very willingly. Maybe even enthusiastically. We kissed for a while, and eventually I said that I was going to bed, but I would see her in the morning. She maybe looked a bit disappointed. I was, of course, very disappointed too, but it was worth it to build the anticipation, and to start to build actual desire on her end.

The next night, I asked her to wear a particular dress with a sexy pair of panties, stockings, heels, but no bra. It was a very short dress, coming barely below her ass. It was also strapless. Her shoulders and legs looked amazing in the outfit, and I would swear she had put a little more effort into doing herself up than she usually did. She served the dinner and then desert, and we drank. After dinner, she started clearing the plates and when she went to pick up a particular bowl, I leaned sideways to see the back of her dress come up to show the very bottoms of her ass cheeks.

I told her to stop, and I slid myself over to get a better view. I asked her to lean further forwards and arch her back again. This caused the dress to rise up maybe halfway up her ass. I could see the tiny triangle of her panties that were covering her pussy. I kept her like that for a minute while I looked her over and then let her continue. She looked somewhat embarrassed when I let her finish, but she had a slight, mischievous, grin on her face too.

After she was done, she came back in and asked me if there was anything else I needed or if she should go to bed.

I said, "yes, there is one more thing. Take off your dress for me."

She was clearly aware that this would be the first time I would see her naked breasts, but she didn't seem as put out by that possibility as I might have expected. She reached down and grabbed the hem of her dress, pulling it slowly up and over her head. Having seen her in her bikini and underwear I wasn't entirely surprised by her breasts, but somehow they looked even better than I had imagined. She looked incredible standing there topless in the stocking and panties. She looked embarrassed, but to be honest she also looked excited. I can't say for sure, but I think her nipples were getting hard.

Tempted by this sight of her nipples, I told her to touch her breasts. She apprehensively complied, and started massaging them and softly squeezing her nipples. After a minute, she started to seem to enjoy it more, and I think I noticed her panties getting damp. She even let out a quiet moan.

Satisfied, I said, "OK, now you may go to bed." She looked slightly let down, so I added, "However, as a special reward for doing so well you may masturbate in your room in you please."

She looked slightly taken aback by receiving her first instruction that involved actual sexual contact, even if it was just her own contact, but she went to grab her dress and head to her room. I told her to leave the dress, and she dropped it.

The next night, I had her wear a similar outfit, but this time before dinner I had her stand up and take the dress off. I had her play with her breasts again for a minute and then told her to go get dinner. The sight of her serving the food half naked turned me on more than I would have thought for some reason, and it seemed be make her feel more exposed as well. When we had desert, I told her to come over and sit on my lap. My cock was rock-hard at this point, and when she sat on my lap it felt quite pleasurable. I instructed her to feed me the desert, which she did. Afterwards, I told her I was going to sleep and left her to clean up the table topless and perhaps a little frustrated.

Up to this point, she spent most of her days relaxing by the pool, doing light cleaning, and doing normal sorts of things. I sent her out to do shopping a couple of times wearing cute dresses, but nothing revealing or anything like that.

Another night I had her wear a very small, tight, white pair of shorts and a tank top. We were watching TV and cuddling and I had her lay face down over my lap and I rubbed her ass through the shorts while I watched the show. Her ass felt so perfect....

Finally, I couldn't resist any longer. I needed to touch her. The next night we had dinner as usual, and afterwards I said that I was going to watch TV and instructed her to change into a specific nightie I had bought her, and a pair of panties. It was white and slightly transparent, and the panties were white and quite small, but they covered her completely. When she walked into the den I was once again reminded of how attractive she was. She sat down next to me, and I pulled her closer. She cuddled up sweetly next to me.

When the show we were watching was over I told her that I wanted her to tuck me in. She seemed to be thinking that this was finally it and she would be expected to have sex with me, but that wasn't what I had in mind. Not yet. When we got into my room I stripped down to my boxer shorts, climbed into bed, and beckoned her to join me. She slid in next to me and I pulled her close and started kissing her. Then I pulled her on top of me. My cock was straining against my boxer shorts and pressing up against her body. It felt wonderful and I was very tempted to just strip her and fuck her, but I resisted. We made out like that for a while and I started moving her hips slightly back and forth. She was clearly very aroused and so was I.

After a while, I told her to take off her nightie. She sat up straddling me and slipped it up over her head. I was very excited at this point, but struggling to keep it tame. I reached up and started massaging her beautiful breasts. She moaned at the contact and started grinding against me subtly. After a few minutes I pulled her down on top of me and we kissed more. Her body felt amazing rubbing against mine from head to toe as she wiggled back and forth. After playing like this for maybe an hour I couldn't take any more and I summoned up the will to tell her that that would be all. At first she didn't get up. She just looked sort of surprised and let down.

After a second I said, "you may return to your room, but you have not been given permission to masturbate tonight."

She asked me impishly how I would even know if she did. That was when I grabbed the remote and the TV came on. It was showing an infrared image of her room. I explained that I had a hidden camera in her room, but that it was only infrared, and fairly low resolution, so I could not actually see her, but I could certainly tell if she were masturbating.

At first she looked a bit offended, but then she slid off of me and said "I would never disobey your instructions master" in a very sex kitten voice. I almost grabbed her and fucked her right then, but I stopped myself and she left.

Each of the next few nights we repeated roughly the same pattern, but I always kept my boxer shorts on and had her keep her panties on. She would leave each night and both of us would be on the brink of freaking out from the frustration. As time went on she would grind against me with more and more conviction, clearly trying to get herself off. I stopped her each time and sent her to bed with instructions not to touch herself before she succeeded in bringing either of us to climax. She was clearly getting more and more frustrated at being brought closer and closer to orgasm, but never getting there, or even being able to bring herself there. I was really enjoying touching her ass, grinding with her, sucking on her tits, and leaving her so frustrated. Each night after she went to her room I watched her on the camera to make sure she was obeying and jerked myself off.

A few days later I decided to take it one step farther. We had been swimming during the morning and she was only wearing the bikini bottoms. They had ties on the sides. After we were done swimming I told her that I would like for her to do some cleaning, and told her that I wanted her to wear her bikini bottom and heels while she did it. There is something hot about watching a woman dressed up like that cleaning... I watched her while I read a book in the living room and she worked around me. She often had to bend over or stretch over her head and I was getting pretty excited. After a while I walked up behind her and pressed my body up against her from behind. I reached around and started massaging her breasts. She stopped cleaning and leaned back against me, enjoying herself. Then I turned her around and squeezed her ass while we kissed. After a minute, I stepped back from her and looked her over.

I told her to get up on the table and dance for me. She did, and made a very erotic show it of. Rubbing her breasts, bending over, arching her back, sliding her hand over her bikini bottoms, etc. After a few minutes I told her to turn away from me. Then I told her to untie the sides of her bikini and let it fall. She hesitated for just a second and then took it off. She danced facing away from me for a minute, maybe getting a little bit horny over the situation. Then I told her to cover her pussy with her hands and turn around. She did, and maybe this was partly for my benefit but she seemed like she was squirming with embarrassment. Finally I told her to put her hands behind her head. I finally saw her completely naked for the first time, and what a sight it was... She was probably the best looking girl I had ever known and she was standing on the table in front of me naked and awaiting my orders....

I pulled her forward off of the table and pulled her body up against me. We made out and I rubbed her completely naked ass for the first time. She felt so vulnerable against me like that... Her pussy was pushing hard up against the front of my swimsuit and my cock was certainly rising to the occasion.. After a while I let her put her bottom back on and finish with the cleaning.

That night, I had her pull her panties off while we were in bed. I grabbed her naked ass and sucked on her tits while she ground against my bulging boxer shorts. This time it didn't take long for her to start sounding like she was close to orgasm. I told her to stop grinding, but I continued to suck on her tits and squeeze her ass to keep her excited, but I didn't touch her naked pussy at all. Finally she started to sound like she was possibly getting close again just from the pressure of my cock against her and the stimulation of her tits and ass, so I sent her walking naked to her room.

This time I told her that she would be allowed to touch her breasts that night in her room, and even rub her ass if she liked, but she could not touch, or in any way stimulate, her pussy. She looked frustrated by this arrangement, but when she got to her room I watched on the camera as I stroked my cock. She was certainly starting to lose control of herself to the lust. She climbed up on her bed on her hands and knees and reached under herself to rub her tits. She clearly knew I was watching and was very excited to put on a show for me. Then she took her other arm and reached around behind herself and let her head fall down on to the bed. She was squeezing and massaging her own ass as it stuck up in the air. Finally, she exhausted herself, apparently giving up on achieving orgasm, and fell to sleep.

Over the next few days I entertained myself by making her wear a french maid's outfit while cleaning, looking up the skirt while she leaned over to dust things, having her swim nude with me in my swimsuit, and having her make and serve me dinner in the buff. It was all very exciting, and our tucking in process continued to be extremely exciting, and she was starting to get to the point where she seemed desperate for an orgasm. She was clearly getting excited when I would make her take off her clothes in front of me, even if we were not touching. I was very satisfied that I seemed to have actually succeeded in making her enjoy our arrangement, and start to appreciate showing herself off to me.

One night, when I told her to head off to her room, she flat out asked me, "why can't I just stay here? Please?".

This turned me on, but I told her firmly that she needed to sleep in her own room for now, but that eventually, if she was very good, she would earn the right to sleep with me.

One day I told her that I needed for her to go buy some more clothes for herself. I gave her a very specific list, mostly containing the same type of sexy stuff I had already bought her. However, I told her that I wanted her to wear a particular dress that was very short while she was out. It barely managed to cover her ass, and the top was very low cut and backless. I told her that she would not wear anything underneath except black stockings. She protested that that was too revealing and someone could see her, but I made it clear that it was an order, but that she could take reasonable precautions to avoid anyone seeing her. She came back a few hours later with all of the clothes I had asked her to buy. She didn't say anything, but I got the distinct impression that she had been excited by the ordeal of being so nearly naked in public.

At the start of the fourth week I couldn't take it anymore. I sent her to bed, but told her to come in the next morning, nude, and wake me up. I told her that she was to wake me by sucking on my dick. She looked very excited that the lack of sexual contact was about to come to an end and cheerfully said goodnight.

I could barely sleep. In the morning I actually woke as soon as she opened the door and padded in naked, but I pretended to be asleep. She slid under the covers and her head disappeared. I felt her gently wrap her hands around my soft cock and start licking it. It quickly rose to the occasion, and she slipped it in to her mouth and started giving me a blow job in earnest. It was incredible. After being so close to her for so long without her actually touching me had built up a ton of anticipation, and that all came flooding back. After a couple minutes I was already fighting an orgasm back. I pulled the covers off of us so that I could see her naked body as she sucked me off. It was a beautiful sight.... After another minute I was about to come. I instructed her that I was about to come in her mouth and that she was to swallow it. She let out a slightly apprehensive mumble, but just then I came in her mouth and she swallowed it all. Then I told her to clean me up with her mouth, which she did.

Finally, I told her to go clean out her mouth while I laid there feeling waves of relief. When she came back I told her to run me a bath. When it was ready, I slipped in and told her to kneel next to the tub and wash me. She did, and when she got to my crotch I started to get hard again. I told her to use her hand, and she did, bringing me fully back to a state of arousal again. Once I was hard, I pulled her up towards the head-end of the tub with her hand still holding my cock, and I reached beneath her and started squeezing her breasts as they hung there. Then I told her to use her mouth. She did, and I started to slide into the dreamlike state that blow jobs seem to bring on. I started grabbing her ass since it was more accessible than her tits. As I got closer to orgasm I started to slide my finger up and down the crack between her ass cheeks. She twisted around and spread her knees urging me on. I slid a little farther until I brushed slightly against her pussy as I came in her mouth again and she swallowed. After sucking me clean, and finishing washing my entire body, I got out of the tub and she dried me off. Then I sent her off to make breakfast in the nude.