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Hiring Cindy Ch. 01

By: WhoAmI99



Chapter 1- Arrangements

I am in my mid thirties and single. I'm an average looking guy, but I was fortunate enough to have made a reasonable fortune in the dot-com boom. Recently I moved to Palm Springs and bought a very nice house with a pool, tons of bedrooms, etc. I had had many girlfriends in my life, some of them very attractive, but somehow something was always missing. The relationships would start out passionate, but over time the excitement would wear off and things would get more routine and less experimental. Sometimes I talked to my girlfriends about my fantasies. Sometimes they liked them, and sometimes they didn't, but even when they did like them, they never really were willing to act them out. I was looking for something different, and my mind had started to wander to a different type of arrangement.

This story starts when I was in Boston finalizing some of my affairs there. One of the last nights I was there I went out to a local bar. The bar was frequented mostly by college students, but I always enjoyed the atmosphere none the less. I was sitting at the bar when an attractive girl came up and sat next to me. I struck up a conversation with her. Her name was Cindy. She was very cute in a naive sort of way. She had light brown hair, above average breasts, a nice tight butt and a very endearing face. 

As we talked I discovered that she had just graduated from the university and wasn't really sure what to do next. She was quite nervous at the prospect of finding a job. She would probably have been content to stay in Boston and continue her college lifestyle, except that most of her friends had decided to move to various cities around the country. As the conversation went on it became more apparent that she was flirting with me. The topics started to stray into sexual matters. She was single, and appeared to be relatively inexperienced. She'd had a handful of boyfriends while in school, and the most recent relationship had ended badly a few weeks earlier. The conversation drifted back to her plans for after college. Her lease expired in two weeks and she really was quite concerned about where to go when it did. She didn't have a job lined up, her parents didn't have the money to support her while she looked for a job, and her credit was maxed out.

She joked that what she really needed was to find a rich boyfriend to support her. I joked back that that shouldn't be hard for her to arrange given how attractive she was. She giggled and thanked me for the compliment, but insisted that no guy she had ever met would do that for her. I realized that this was just about the ideal chance to take a shot making my idea a reality. 

Working up my courage, I said that I knew otherwise. She looked slightly startled and asked what I meant. I decided to go for it, and figured I would just come out and say it. I asked her what she would think of someone offering her a 'job' that paid up to one million dollars a year? 

She said that nobody would ever offer a B student a job for even one 20th of that amount. 

I said, "I am right now". 

She looked stunned and confused and she asked me what I meant. I said that I would offer her up to one million dollars to live with me, and be my servant, for one year. She practically fell off of her chair in shock. 

After she calmed down she asked if I were serious. I said that I was and she asked what kind of 'servant' makes a million dollars a year. 

I said that she would be part maid, part secretary, part girlfriend, and part sex slave. I had never said anything like that to anyone in my life, and I was quite nervous, but she didn't seem entirely offended so I pressed on. 

I waited until she composed herself, and finally she said "a million dollars is a lot of money. I would never have to worry about a job again, but a year is a very long time." 

I said, "Well, it is a big decision. One that will affect the rest of your life. I wouldn't want you to make it on the spot. Here is what I propose. I live in Palm Springs now. How about if I fly you out there for the weekend next saturday. I will provide for all your expenses, pay for a hotel room for you, provide you with a limo, and anything else you require. I will also pay you $10,000 just to have dinner with me while you are out there to discuss this further. You may leave at any time and the money will be yours." 

She looked stunned that someone was offering her $10,000 just to have dinner with them. How could she refuse? I got her email address and said that I would send her travel instructions, and bade her goodnight.

The next morning I made the travel plans and emailed them to her. I told her to be at the airport at 9am on saturday, and that the limo driver would meet her at the airport in Palm Springs and take her to the hotel. She was to be ready to come by my house for dinner at 7pm. I also decided to test her willingness a bit. I instructed her to wear a cute dress, matching sexy bra and panties, and high heels. I figured there was only about a 20% chance that she would show up, but I had nothing to lose, so I made the arrangements. To my surprise, the limo driver called me up on saturday after dropping her at the hotel to tell me that she had arrived and would be at my house at 7:30. I was going crazy with anticipation...

Just before 7:30 I heard the limo pull into the driveway. I went outside to meet her. I was pleased with what I saw when I opened the door. She gave every appearance of trying to impress me. Her makeup and hair were done impeccably. She was wearing a classic 'little black dress' that stopped well above her knees. She was wearing black stockings and black high heels. As she got out of the car I was impressed to notice a glimpse of the top of her stockings. That they were not actual pantyhose seemed to hint that she realized she might be asked to take off her dress.

After she got out, I instructed the driver to wait right there, and take her back to the hotel or wherever she requested, whenever she asked. Then I took an envelope out of my pocket with a cashier's check for $10,000 in it. I laid in on the back seat and told her that if she wanted, she was welcome to leave immediately with the check, but that would be the end of our arrangement of course. 

She looked surprised and said that of course she would prefer to have dinner with me, so I lead her inside and sat her in front of the fire on the couch. I thanked her for coming. 

She said that she was very curious what exactly I was proposing. 

said, "ok, right to business then." and pulled out the contract I had prepared. I gave it to her to read. After some legalese it said the following:

#1) I would set up a bank account in solely her name in a Swiss bank. She would have all the information required to verify the balance and nature of the account at any time. Each month, on the last day, I would deposit $20,000 into the account. It would be tax free and anonymous.

#2) I would place an additional $20,000 into that account on the first day of our arrangement.

#3) At the end of the year, I would deposit $680,000 in that same account.

#4) I had set aside $60,000 for bonuses which I would offer throughout the year.

#5) Either of us may call this entire arrangement off at any time. She could call it off without having to give any explanation at all. I would only call it off for one of two reasons- if she failed to follow an instruction or if she did not convey the appropriate attitude. If I ended the relationship after more than 1 month had passed, I would deposit an additional $50,000 into her account. Whenever the agreement was terminated by one of us, she could keep all of the money received so far, but would not be entitled to the 'end of year' payment.

#6) During her term of employment, she would serve me in any role I required. This would include maid services, secretarial services, playing my girlfriend, and playing my sex slave. She would follow any instruction promptly and without complaint. Unless otherwise instructed, she was always to appear enthusiastic, loving, and happy.

#7) I may ask her to do things that she has never done before, or is uncomfortable with. For example, she may be asked to have sex with me, sex with other men or sex with women. She may be asked to wear extremely revealing outfits in public. She may be tied up. She may be spanked, but would not be submitted to extreme S&M or humiliation. I am interested in making this experience as enjoyable as possible for her, but the primary purpose of this contract is to ensure my enjoyment, so she would definitely need to perform some duties that went beyond her normal comfort level. I would, however, ask her to provide a list before we began listing those types of activity which would make her quit the arrangement. I warned her, however, that I would need to see that list before signing the agreement, so she should think long and hard about how far she was willing to go.

#8) She would work for me 24 hours a day, 7 days a week, with the exception of the last sunday of every month, when she would be free to go and do as she pleases, with the sole exception that she was not, under any circumstances to date or hook up with a man during those days.

#9) She was never allowed to masturbate or be intimate with anyone without my permission.

She sat deep in thought after reading the contract. She was clearly apprehensive. 

She said that she didn't know if she could keep something like this up 24 hours a day, every day. 

I said that that was an understandable concern, and that at times it would certainly be tiring for her, but that at the same time, it wasn't my intention to have her playing the sex slave role at all times. I expected that she would spend a fair amount of time cleaning and cooking, a fair amount of time reading in her room or lounging by the pool. I said that I didn't have the energy to play this game constantly either. I also said that it was my plan to start this out slowly, and reminded her that she could quit after a day if she were uncomfortable, and she would be $20,000 richer for her time. 

She seemed consoled by that point, but asked if she needed to decide right then. 

I said "no, let me show you the house first and have dinner".

I took her on a tour of the house. I showed her the pool, the various living rooms, my bedroom, and her room. Her room was really a large suite of rooms with a nice bathroom, a good sized bed, a huge walk-in closet, and all of the luxuries one could desire. She was clearly impressed by the house and excited by the idea of living in such luxury for a year. After the tour was sat down at the dinner table and I brought in the food. I told her that that was probably the only time I would be serving her dinner and we laughed. We talked during dinner, and really continued to hit it off. She was smart and funny, and gave every sign of enjoying my company.

After desert I asked her if she wanted to leave, or if she would be interested in continuing the 'interview'. She said that she wasn't sure yet whether I would accept all the things she wasn't comfortable doing, but she wanted to keep talking about it.  

I said, "great" and said that we should get to her list in that case. I reminded her that there was a lot of money on the table, so if she was serious she should be very careful of how many things she put on the list of things she will not do. I brought her into the study and gave her a piece of paper, and left her to think things through.

When I came back, she presented me with the list. She had written that she would quit if she were asked to do a predictable list of things like scat play, serious S&M, anything that would get her arrested, etc. There was only one item on the list that I didn't like. She said that she would not have sex, or even touch, any strangers. 

I told her that I didn't know how far I would want to take it in reality, but that I definitely had fantasies about asking her to touch, be touched by, and have sex with strangers. I said that if she were firm about that rule I would not accept the arrangement. She looked very distressed, so I offered her a compromise. I would not ask her to touch or be touched by anyone other than myself, for the first 3 months at least. At that point, we could discuss it again. If she still felt strongly about that point, she could leave with a good chunk of money. 

She said that that sounded reasonable to her.

Then I said that I wanted to see what I was getting for my money, and I asked her to stand up and take off her dress. She looked uncomfortable, so I reminded her that she could leave at any time. She looked like she was considering it, but ultimately she stood up facing me and nervously unzipped the back of her dress. She let the dress fall off of her shoulders and then down to the ground and she stepped out of it. She looked stunning. She had on a matching, small, black pair of panties and bra, her thigh-high stockings, and a pair of high heels. I was very pleased and started to get excited. She looked uncomfortable, but didn't cover herself. I asked her to turn around. She complied nervously, and I was satisfied to see that she had a great ass that was barely covered by the thong back of her panties.

I said that she was very beautiful, and that she could put her dress back on. She quickly complied, and I said that I was satisfied with both her list, and her beauty. I asked how she felt about the arrangement. 

She said that she was very interested, but she wanted more time to think about it. 

I said that that was fine with me, and suggested that if we were to do this she should be at the airport in Boston, with the signed agreement, one week from that day. I instructed her that she should wear something cute, but bring only a small bag with personal items. I told her that there was no need to bring any clothes, and that I would be providing her with a whole new wardrobe. I took down her size and measurements and walked her back out to the limo. I held the door open for her, and she said that whatever else happened, she had enjoyed having dinner with me, and she gave me a quick kiss on the lips before getting into the car.

I was not certain that she would come, and we didn't talk at all during the intervening week, but I spent my time preparing just in case. I bought her dozens of dresses, pairs of underwear, stockings, swimsuits, costumes, night gowns, and everything else I could think of. It ranged from cute to absolutely over the top sexy. I put it all in her closet and waited.

Hiring Cindy Ch. 02



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.




Hiring Cindy Ch. 02



A few days later, I asked her to wake me the same way again, and after I came I said that I had a special reward for her. I told her to sit on her feet on the bed and spread her knees. Then I told her to rub her tits for me. She started to get excited, and then I told her that she could touch her pussy and make herself come. Normally, a somewhat reserved girl like this would have been very uncomfortable doing that with someone watching, but in her current state of frustration, she looked incredibly relieved. She immediately started roughly stimulating herself and quickly had an orgasm. I was really enjoying the show... After the waves finished, she started to blush and looked embarrassed at what she had done. Now that the lust was satiated she appeared to have a different perspective on things. I told her that would be all, and she left the room.

The next day was the end of the first month and a Sunday. I deposited the $20,000 in her account and told her that it was her day off. I said that she was welcome to hang around the house, but there were also some restaurants and tourist stuff I could recommend. She took the info, thanked me, and headed out. She got back later that night and said it had been kind of boring.

I told her that it was still her day off, so she could speak openly. I wanted to know how she felt about things so far. Was she willing to go on? I reminded her that we were just starting slowly, but she could quit if it got too intense and keep the money in her account. She looked kind of embarrassed to answer, since she was no longer hiding behind the arrangement. Eventually she said that she definitely did want to continue, as the money was so good. I asked her if there was anything she needed or wanted to change. She was kind of uncomfortable answering, or perhaps even having trouble admitting how she felt to herself, so she just kind of mumbled a 'no'. I let it go at that. 



Hiring Cindy Ch. 03



Chapter 3: The Trip

The second month started off where the first had left off. I had her wear more and more sexy outfits around the house. Transparent nightgowns, tiny dresses, extremely small shorts and shirts, and so on. And, of course, I had her spend more time naked, had her give me a blow job every day or two, and let her masturbate for me on the fourth day. One day I had her suck on my cock while we were watching TV. I had her strip and kneel on the carpet while I stayed sitting on the couch. Something about that really turned me on...

One night in bed after I allowed her to masturbate briefly, I pulled a dildo out of my nightstand and handed it to her. I instructed her to get up on her hands and knees and fuck herself with it. She gave me a quizzical look at first, but moved onto her hands and knees. She slowly slid it into her pussy, and started moving it in and out. After a while, she started to get more excited and began thrusting back to meet the dildo and moaning louder and louder until she came. I was incredibly turned on, and had her suck me off again.

On one Thursday night I asked her to tuck me in as usual. I had her strip naked, and I left my boxer shorts on while she straddled me. After a while I had her pull off my boxer shorts and suck on my cock with her ass sticking up in the air next to me. I started rubbing her ass again while she sucked, and started teasing her pussy. After a few minutes I actually started massaging her clit. She made a very excited noise around my cock and started to thrust against my hand. She was writhing around in a very excited animal way. I brought her to orgasm right about at the same time that I came in her mouth.

Finally, that Sunday morning, I had her come into my room naked and wake me up by sucking me off again. That was rapidly becoming my favorite routine... When I was hard, I pulled her up on top of me. My cock directly touched her pussy for the first time and I think we both felt something exciting. She slowly rubbed her pussy up and down on my shaft, getting very wet. After a minute I told her to slip me inside of her. She did, and I easily slid all the way in. We fucked like that until we both came and collapsed in the bed. That night I let her sleep in my bed with me and we fucked again in the middle of the night.

The rest of the month was wonderful. It was essentially more of the same. I fucked her whenever I felt like it, sometimes in bed, sometimes bent over the dinner table, sometimes in the pool. Wherever struck my fancy. I had her naked a lot of time around the house, and sometimes I noticed that she would be naked, or put on a see-through nightie or similar when she was just lounging around the house without me asking. I think she was starting to enjoy being naked, and I certainly was as well.

A couple incidents that I found particularly excited included one night that I made her kneel on the table and masturbate for me while I ate. When she got close to orgasm I told her to take some of the mashed potatoes and rub them on her tits. Then I told her to get down on all fours. She did, and then I had her rub them between her ass cheeks and finally on her pussy. It was very exciting seeing her behave so wildly, and I think it turned her on as well because she had quite a loud orgasm.

Another thing of note is that I had her make a special 'costume'. It was basically just a string that went around her waist and a square of cloth that hung in front covering her pussy (most of the time). For some reason that outfit really excited me and I was always touching her ass when she wore it.

We also spent a lot of time just doing normal things around the house. We were starting to get quite comfortable with each other, and maybe she was just playing the part, but I started to feel like actual romantic feelings were starting to develop between us.

Mid way through the third month I decided that we needed a vacation. I settled on Costa Rica, which she was very excited about. I packed her bag for her and didn't let her look inside, and we headed off to the airport. When we got there we checked into our hotel room, had dinner out, etc.

On the first morning we decided to head to a particularly isolated strip of beach we had read about. We had to drive along a lot of dirt roads and whatnot to get there, but when we did it was worth it. White sand, blue water, perfect weather, and not a soul around. We started walking down the beach, her wearing a bikini, but after a while I said that since no one was around I would like for her to give me her bikini. She was hesitant for a second, but then she took it off and handed it over. It was very erotic seeing her naked outside in such an amazing setting, but we were both reasonably sure that no one would see her.

After we had walked for a ways we put down our towel and swam for a while. I left her bikini and my swimsuit up on the towel. It was exciting to be naked, and far away from our suits outside.

When we got back to the towel, I started kissing her and we fucked. She was on top. While we were in the midst of it, a boat came into sight going along the shore. I don't think she saw it and I didn't say a word, we just kept fucking. As the boat got closer, I could hear it. She didn't turn around or give any sign that she heard it, but I think she must have. In fact, I think she started to fuck me harder and get louder as the boat got louder. It was out a little ways, so I don't know for sure that they saw us, but they could have if they were paying attention. As the boat started to disappear to the right I came inside of her and she came a second later.

The next day we went to the main beach. I had her wear her sexiest bikini even when we were walking out through the hotel lobby. She looked great, and got stares from all the men we passed on the way to the car. When we got to the beach we sunned first for a while, and then went for a swim. There were people everywhere. When we were out in the water I pulled her against me and started kissing her. She slipped her legs around me and pulled close. To her surprise, I reached around her and untied her top. She let me pull it off of her reluctantly. The nearest people were a little ways away so they probably couldn't have noticed anything. Then I untied the ties on the sides of her bottom and pulled it off of her. She crushed up against me harder now that she was naked. We could see lots of other people, but I don't think they could have seen anything below the water line. As we made out I rubbed her tits and squeezed her ass and she started to slowly grind her pussy against my cock through my suit. After a few minutes, I grabbed her hand and slipped it inside of my suit and she started to massage me. I whispered in her ear telling her to pull my suit off and hand it to me. She did, and then we embraced again. It felt amazing to have her naked body pressing up against mine while we could see other people. I kept molesting her and she kept rubbing my cock. Then I grabbed her hips and pulled her pussy on to my dick and slipped inside of her. She was a little surprised, and nervous about doing this in a public place, but she started to slide up and done on me none the less. As she got more aroused she started to make muffled moans. Eventually we came, and I think some people heard her and looked over, but no one could have seen anything, they probably guessed what we were doing though.

After we came, I handed her back her suit, and I slipped mine on as well. Now that a couple of people seemed to have noticed that something was up she had more trouble getting the top back on without being conspicuous, but she did her best and we went back to the towel. As we got out of the water a handful of people were clearly watching us, and she seemed pretty self conscious. When we got back she whispered that she wanted to go now. I said not just yet. I gave her a towel and told her to wrap it around herself and slip her suit off beneath it. She did her best to be discrete, but a couple of guys were clearly watching. I think that one of them got a good glimpse of one of her breasts when she slipped the top off. I was starting to get excited again seeing other people watch her, but we packed up and left. 

On the way back in the car I ordered her to take off her towel and suck me off while I drove. Once we were driving, she complied, and I came in her mouth. I didn't let her put her towel back on until we entered the little town. We walked back up to the room, and at least a couple people took notice of the beautiful woman that appeared to be wearing only a towel....

That night we went out to a club. I selected a very short, very see-through dress for her. At first she said that there was no way she could go out in public wearing that, but I assured her that it was a more relaxed culture down here, and picked out a fairly conservative black set of bra and panties for her to wear underneath, and some high heels. She agreed, but clearly wasn't happy about it.

When we walked out through the lobby, everyone stopped and started at her as she went by. I was very proud of the catch I had. She looked absolutely stunning and everybody knew it. You could clearly see her underwear through the dress. We got out to the car and drove to the club. When we went in everybody stared again, much to my satisfaction. I was hard already.

We drank, and talked, and I kept noting everyone checking her out. She loosened up a little bit as the booze kicked in. After a while I asked her to dance for me. She complied and started dancing in front of me while I sat on one of the couches. As it went on the dance got more and more sexual and I was really starting to get aroused watching her showing off in front of everyone. After a while I pulled her on to my lap and started kissing her. I reached around and cupped her ass while we made out. She seemed put of by that at first, but eventually relaxed and started kissing back in earnest.

Then I instructed her to go into the ladies room with her purse, take off her bra, and come back out with it in her purse. She looked stunned that I would ask her to do that. She protested that she could get arrested. I told her that first of all it wasn't against the law to be topless in Costa Rica, but secondly, no one would ever turn in a pretty young lady like her for sharing too much of her self like that. She didn't want to do it, but I flatly told her that this was one of the times when she needed to put my desires first and earn her money. I said that in fact, since she had resisted my order, she would also have to change into the other pair of panties I had hidden in her purse. She looked mad, but got up and headed towards the ladies room.

When she came back out, she looked stunning. Her breasts were clearly visible, and everyone in the club noticed what she had done immediately. The new panties were much smaller than the first pair as well. They were small in the front and just a thong in the back. Anyone who wanted to could get a great view of her ass or tits through the dress. She looked petrified, but she walked back over to me and sat down. I asked her to go get me a drink from the bar. She got up and went over to the bar while all the guys were checking her out. At the bar she had to lean over the bar so the bartender could hear her and the back of the dress rode halfway up her ass. I was in heaven, and a lot of guys were openly ogling her.

When she got back I sat her on my lap again and started kissing her. I slid my hand under the back of her dress and was caressing her ass openly. She was very uncomfortable with the situation, but started rubbing her pussy against me anyways. I was getting very hard, and after a while I whispered in her ear that she was a very good girl, and then we got up and left. She got a lot of attention again walking through the lobby, and when we got back to the room I bent her over the desk and fucked her hard from behind. She was very wet when I slipped inside of her, so maybe the whole experience wasn't all bad for her either....

The rest of the month was pretty uneventful. I continued the same sort of thing. We slept naked together every night, and sometimes I would fall asleep with my hand on her tits and pussy. We had a lot of sex and blow jobs and whatnot, and exciting outfits of course. One day I made her go grocery shopping wearing a tight, white, narrow band top, an equally tight and narrow miniskirt with nothing underneath, and a pair of white platform boots. She looked like a total slut wearing it, and when she got back I fucked her from behind again while she was still wearing the outfit. I also had her put on a really short, slightly see-through nightie and a very hot white pair of panties one day and answer the door when we ordered a pizza. It turned me on, but the guy just stared, accepted the money, and left. She seemed really horny afterwards.

At the end of the third month, as I had promised, we talked again about her list. I brought it up, and she said that of course she had been thinking a lot about what she would and would not be willing to do with other men, and she was not at all comfortable with the idea. 

I asked her if she hadn't ever fantasized about being with random men or multiple men at one time. 

She said that of course she had fantasized about it, but that fantasy and reality were very different things. She said that she really wanted to continue to stay with me, and she was very happy with the situation, but that she was very afraid of what I might make her do with other men if we continued the arrangement. 

I said that the idea of other men seeing her body, touching her, and her touching them was very exciting to me, and that I would have to end the arrangement if she couldn't accommodate that desire. She looked scared, but I backed off a bit and suggested another compromise. I suggested that for the next 3 months I would agree not to ask her to have sex with anyone other than me, but I said that that was all I could commit to. I might ask her to be naked in front of men, touch them, let them touch her, or maybe even go down on them. But, I reminded her of how I liked to take things slowly, and I said that since she can leave at any time, why didn't she just stay as long as she was comfortable? 

She agreed, but was clearly distracted and a little bit divided for the rest of the night. 



Hiring Cindy Ch. 04



Chapter 4 - The Dinner Party

The start of the fourth month was basically more of the same sort of things. I was having more sex than I probably ever had and I was loving it. We spent a lot of time doing normal sorts of things, but usually with at least some touch of the erotic, and some of the time, of course, I would have her posing for me and whatnot. One night I had her climb up on the table while I was eating and face away from me on her hands and knees while she masturbated. Another night I had her climb under the table and suck me off while I ate.

Mid way through the month, I told her that I was going to have a dinner party and that she would be the hostess of course. She asked me exactly what I meant by that, but I said that she would just need to wait and see. I was having a group of six male business associates from Germany over for dinner. I didn't see them often, and didn't really know them very well, but when I was in Germany they'd taken me out to a number of good strip clubs, and I was very confident that they would enjoy what I had planned. As long as Cindy went along with it...

The day of the dinner she was preparing the food in the afternoon. I went out shopping for her clothes for the night. Before I left I told her to dress in her French Maid's outfit. It was sexy, but didn't show anything. It consisted of a very short dress with the ruffled petticoats underneath, a strapless top that was very low cut and pushed her breasts up impressively and had low back. I instructed her to wear a very small pair on panties and the garter belt and fishnet stockings with very high heels. When I got home she met me at the door wearing the outfit. She was nervous. She had worn less in front of strangers a number of times, but something about being the hostess and clearly wearing this outfit for the excitement of the guests made her feel more of the pressure of attention. Regardless, she didn't complain and the guests started to show up shortly afterwards.

The guests all complimented her on her outfit. Some with very lewd looks... She served us dinner and each time she put down a plate one of the guys or another would lean back to catch a glimpse of her ass. One time a guy did it very blatantly and I happened to catch his eye as he was doing it. He looked embarrassed, and he apologized as soon as she went back into the kitchen. 

I said, "no, by all means, she is a very attractive woman and I appreciate the fact that other men like to look at her." 

They all concurred that she was very attractive, especially in the outfit she was wearing. I said that they hadn't seen the half of it. I explained that she was a bit of a exhibitionist and tended to wear very revealing outfits. They were trying to be subtle, but one of them couldn't help but ask what kinds of outfits I was talking about. I said that I wasn't very good at describing that kind of thing, but maybe I could persuade her to show them one or two of them. They all looked a little surprised, a little embarrassed, and a good deal excited.

When Cindy came back in I told her that we had just been talking about some of the wonderful outfits she has and I asked if she wouldn't mind showing us one or two of them. I had left the shopping bags in the den, so I 'offered' to grab them for her. I went and got the new things I had bought that day and gave her the first bag. She took it with her into the other room to change. It was a very short white dress and high heels. The dress was low cut, barely would cover her ass, and was so low cut in the back that from some angles you could see the curve of the top of her ass. I put a note in the bag earlier explaining that she was not to wear anything other than what was in each bag. 

She came back out after what really seemed like too long of a delay... She looked great. The dress was extremely sexy, but almost had a class about it as well and she carried it off well. She brought us out drinks, and more than a few times one of the guys would catch a glimpse of either the top or bottom of her ass, or part way down her chest, but I don't think anyone saw her nipples or pussy or anything. She was fairly nervous and was moving around very carefully. The guys ooo'd and ahh'd over her outfit and I kept leading them into being comfortable telling her how sexy she was. They picked up on it and were pouring compliments on her.

After a while, one of the guys asked if perhaps she had any other wonderful outfits that she would like to show them. I jumped in and said that of course she did. I handed her the next bag. This one had a matching skirt and tank top. They were both made out of a very thin, silky material that clung to her body very closely. The skirt was incredibly short and had slits in the side as well. I knew that no matter what she did, she would likely be flashing part of her ass from time to time, and if she wasn't very careful she would be flashing her pussy as well. The top was fairly small, but tight and the way it clung to her you could clearly see the shape of her nipples through the fabric. She must have been looking in the mirror pulling together some courage for a while, but when she came back out the guys were stunned. She was a vision, and the nervousness she was showing just made it more exciting. She brought out desert and was very careful how she moved, so I don't think anyone saw much of anything. At least not much of the very small portion of her body that the outfit hid...

After she gave everyone their deserts, I pulled her onto my lap sideways. I put my arm around her back and my other hand on her thigh. Everyone was talking for a while, but it was pretty clear that everyone's minds were on her body. After a while I started kissing her and we got pretty heavy for a bit. I was rubbing my hand up and down on her thigh, and maybe pushed the skirt up slightly and brushed against her breasts, but nothing too intense. Finally, the guys couldn't pretend not to focus on her any more. They all just started talking at length about how beautiful she was, and how wonderful it was that she was so open, and how much they liked her outfits. She was clearly loving being the center of attention and getting so much over the top praise... She giggled and squirmed around a little, but didn't say anything to discourage the guys from looking her up and down in her half naked condition. Finally, she stood up and started clearing all the desert plates.

As soon as she left the room, one of the guys asked whether I had any, um, other outfits that she might like to show us. I hesitated, and then said that yes I did. In fact, I had one that was significantly more interesting than the ones she had worn so far, but that I wanted to be very clear about something- this was not going to turn into a gangbang. I would only ask her to try on the next outfit if I was comfortable that all the guys understood that she was for looking at only, and that none of them would be allowed to touch her in any way. I would be the only person that would be allowed to touch her at all. They would have to go back to their hotel rooms and jerk off at the end of the night. I asked them if they were comfortable with that and wanted to see if I could get her to try on another outfit. I made sure that I got agreement from each one individually. A couple of them seemed a little bit disappointed, but they all agreed, and I knew that I could trust them. Most of them I trusted individually, since I knew them, and with the whole group here I didn't think anyone would try anything inappropriate.

So, I grabbed the last bag and went into the kitchen to talk to Cindy. She whispered that she had overheard our conversation and she thanked me for being so careful, but she said that she was sort of apprehensive about what would be in the bag I was holding that warranted such a fuss.... 

First I told her the plan of what she was to do, and then opened up the bag for her. The bag held a small, transparent black nightie and a tiny, transparent, pair of panties. Worn together they were enough to hide her pussy, but either one by itself would be transparent. She was very nervous about some of the things I had told her to do when she was out in the room again, and the outfit didn't help calm her much, but she was definitely excited as well. While we talked, I lifted up her top and rubbed her breasts with one hand and reached under her skirt to touch her ass with the other. Then I guided her hand into my pants and let her stroke me for a minute before going back out to let her change.

When she came back in, conversation stopped and everyone's jaws dropped. Her gorgeous breasts were plainly visible through the nightie, and really the only part of her body you could not see clearly was her pussy. I think the guys were expecting something sexy, but not this revealing. 

She strutted up to the table next to me and said, "so what do you think boys? Do you like this outfit?" 

That broke the silence and they all started raving about how amazing she looked. A couple of them even said that she was making them horny. I told her that as good as the front was, we would sure like to see the back as well, and she turned around and bent forward accommodatingly. I was impressed. She was carrying this off with more confidence than I thought she would have. And I noticed that her nipples were very hard. The danger and 'naughtiness' of this was clearly a turn on for her as well as myself. The guys just watched her and she sort of half-danced, half-strutted around taking in their attention and finally came and sat on my lap again.

We all talked for a while, but nobody was even pretending not to stare at her anymore. One of the guys talked about how he wished his wife would experiment like this more, and so on. Cindy and I kissed from time to time and I fondled her somewhat. After a while, I started to slide my hand up her thighs, and then over her stomach and up to her breasts, lifting the nightie as I went. It was pulled up well above her belly and the front of her transparent panties were clearly visible to at least a few of the guys. They were not as transparent as the nightie, but you could definitely make out her pussy. 

She pretended to be oblivious, but it was obvious from the way she was squeezing my arm that she was fully aware of what I was doing. I started to massage her breasts in earnest and then I whispered to her to pull her nightie the rest of the way off. She did, glancing some of nervously around at the other guys, who were all sitting there watching, enthralled while I rubbed her ass and tits while she sat on my lap wearing nothing but a flimsy pair of panties.

After playing for a while I asked her to get us another round of drinks. That gave the guys that were not lucky enough to have had a good view of her when she was on my lap a chance to take her whole body in, and it gave all of us a good look at her ass as she walked away into the kitchen. 

As soon as she went into the kitchen, I said that I was very serious about what I said about this not being a gangbang, and emphasized that anyone who took this any farther than I explicitly said was allowed would get kicked out right that second. But, I said that maybe we could be a little bit flexible on the strict no-touching rule... I said that I would allow them to cop a quick feel of her ass or her tits as she gave them drinks, but no more.

Just a second later, she came in carrying a tray with the drinks. She went around the table giving one guy a drink at a time. She had to hold the tray with one hand while she put the drink down with the other, all the time balancing on some fairly ridiculous heels, so the guys basically had free reign of her body. Most of them grabbed for her ass, since that was the easiest, but a couple snuck a quick feel of her tits. She neither pulled away nor encouraged them. It didn't seem like she knew how to react, so she just didn't. At least, not outwardly. She brought me my drink last, and when she leaned forward to put it on the table I reached around her and grabbed one of her breasts with each hand. I had to bend her forward slightly to reach, which was even hotter. I slid my hands all around her body in front of all the guys, and finally I stood up behind her and pulled her back up straight. I massaged her breasts for a while, and let my hands slide over her pussy from time to time. She leaned back into me and moaned a bit. By the way she was breathing and moving I could tell she was extremely aroused.

So, I took her hand and moved it to one of her breasts. She started touching it while I touched the other and teased her pussy and stomach. After a few minutes, I reached under the sides of her panties and pulled them down, leaving her naked in front of all 8 strangers. She didn't miss a beat, and kept working her breast while I started to rub her pussy. She was rapidly approaching an orgasm, but I wanted to milk it out longer so I slowed my pace. She was moaning and writhing against me and all the guys were in awe at what they were seeing. I noticed two of their arms moving back and forth below the table. Then, I took her left hand and slid it down to her own pussy and whispered that she was to keep herself on the brink of cumming, but was not allowed to make herself cum yet. She was clearly having trouble following that instruction, but managed to hold off. I stepped back and walked around to the other side of the table to take the spectacle in. It was incredibly erotic to see her touching herself, clearly in the sway of her passion, in front of all these strangers.

Finally, I went back to her side and whispered that she could cum now. I rubbed her breasts while she brought herself off. One or two of the guys appeared to beat her to the punch... She came very quickly, and extremely loudly. She was shaking uncontrollably for a couple of minutes, and when she finally slumped back into my arms she was beat. I lead her into the bedroom and laid her back on the bed naked. As she sat down on the bed she reached out and unbuttoned my pants and quickly fished my cock out and into her mouth. I let her suck on it for a minute or two, but then told her to wait there, as she was, and not to touch herself, until I was back.

I went out into the dining room again and 5 of the guys had already left and one more was getting his coat together. He gave me a very grateful thanks and goodnight and went on his way. The other two were still drinking the last of their drinks in the dining room. They both said that they were blown away by Cindy, and thanked me over and over again. We talked for a few minutes, and then I said that I had matters to attend to with Cindy, and that I would have to wish them goodnight. They were clearly both hoping for something more, but they started to get their things together. I told them both that if they would be interested, maybe I would have them back another time... Maybe for a more interactive night. They both heartily encouraged that, but went on their ways.

I went back in to the bedroom and let Cindy suck my cock until I came in her mouth. We both dozed off for a couple of hours, but I woke up later with a raging hardon and I rolled over and slipped it into Cindy's pussy almost before she was awake. She was still so wet, and must have been dreaming of something pretty hot because I slipped right in.

The rest of the month was comparatively tame. We had both probably used up a lot of our sexual energy on that night... A few nights after the party, though, she did tell me that she never thought something like that would make her so horny, but that it was incredible how it took hold of her. She was definitely embarrassed about what she had done, but excited by it at the same time. 



Hiring Cindy Ch. 05



Chapter 5: The Girls Arrive

Part way through the fifth month I decided that it was time to go for another one of my fantasies. I was going to be out of town visiting family for 2 weeks and I couldn't take her with me. So, I gave her an assignment. She was to travel to Chicago, hang around in the college bars and meet women. As she met the women she was to try to find attractive, relatively innocent women. She was to offer them a deal. I would pay them $25,000 each for spending one week with us as my total slaves. They would be required to obey absolutely any order unless that order would get them arrested or injured. They could leave at any time, but would only be paid if they went through with the whole thing. I told her that I would give her a $20,000 bonus for each girl that she got, who I accepted, and who spent the whole week.

She was very nervous about approaching strange women with this shocking offer, and really didn't seem to think she could pull it off, but I insisted that she do her best. I told her that I needed her to find two that met with my standards. She didn't seem at all convinced that this would be possible, but I sent her on her way and I went to see my parents.

When we were both back she informed me that it was a successful mission. She looked very pleased with herself, and I was pretty impressed as well. I reminded her that they would have to stay through the week, and that I would have to accept that they were attractive enough if she was to be paid for them. They were set to arrive the following weekend.

That night she asked if she could speak openly.

I said "sure." 

She told me that she had never been with a woman and she was nervous that I would make her be with these women, and she didn't know how she would react. 

I explained to her that the primary reason I wanted these other women was that I didn't feel right making her do some of the more humiliating things that I fantasized about, but that I could do those things with these women that I didn't know. I then said that, yes, I did expect that I would want her to be with them, but that at least for now, she would not be asked to do anything she didn't want to do. I would not order her to touch their pussies, or let them touch hers, without her explicitly agreeing to it. 

She seemed very nervous about the upcoming week, but we fucked anyways. Talking about the other women always made me horny....

The next day I gave Cindy instructions to relay to the women for travel and dress. They were to each wear very short, dresses with nothing underneath. If I didn't feel that their dress was short enough, I warned them that they would be severely punished. They were to wear the dresses to the airport, and only bring their toiletries with them, no clothing.

When the weekend came, the limo brought them to the front door. I was very impressed. One of them, Megan, was a curvy woman. She had light brown hair. She wasn't fat at all, but she had large breasts, a big frame, and a healthy ass. She had a pretty face as well. She was wearing a loose skirt that almost reached her knees. This did not strike me as what I had instructed her to do.

The other girl, Kerry, was smaller, but very sexy in a traditional sort of way. She was blonde, had fairly big tits, a great figure and a drop dead gorgeous face. She looked very innocent as well which really excited me. She was wearing a silky dress that clung to her great figure and made it clear that she wasn't wearing anything beneath. It was also very short, hardly covering her round ass.

I complimented Kerry on her dress, but told Megan that I had asked her to wear a very short dress, and she had not followed that order. For that, I told her that she would be punished, but not yet. We came inside, and Cindy came down from upstairs to greet them wearing a small, but not see-through, nightie and heels as instructed. I went over the rules with them to make sure that we were clear, and they were. Then I showed them to their rooms and said that Cindy would be down in the morning to get them ready. They were to change into the simple nighties that were waiting for them in their room and go to sleep for the night. Their room only had one double bed, and I told them that the two of them would be sleeping in the bed together whenever they slept in that room.

In the morning I sent Cindy down with specific instructions. She woke both of them up and told them to get up and take off their nighties. She said that they had seemed uncomfortable being naked in front of her while she was dressed, but they did it. Then she told them to shower together and wash one another while she watched. They did as instructed without any eroticism. Afterwards she handed them their outfits for the day. They were short, white, backless, but simple nighties, and high white heels. Then she instructed them that they were to prepare breakfast and serve Cindy and myself in thirty minutes. At breakfast I got a good chance to check out the girls' figures. Cindy had done well. They were both very sexy in very different ways. I only had these two for one week, so I knew I wouldn't take it slow like I did with Cindy.

After breakfast I informed Megan that the time for her punishment had come. I slid my chair back from the table and told her to lie across my lap. As she did the back of her nightie came up exposing most of her ass. She squirmed around, clearly uncomfortable with having her ass sticking up in the air on display and nervous about what I was going to do. At first I just rubbed her ass, even sliding my finger along her crack. Then I pulled the nightie up higher so it was completely above her ass. I couldn't see her pussy at all, but her ass looked spectacular and I was getting very hard. I started to spank her. I alternated between spanking and caressing for a while, and she seemed like she was starting to get aroused. She let out little moans of pleasure and squirmed around when I would caress her, and let out little yelps of surprise when I spanked her. The other girls watched closely but didn't say anything. When I was satisfied I told her to get up and clear the table. She looked very distressed, but obeyed immediately.

For dinner I had Cindy dress them in completely transparent nighties and panties with heels. When they came back up they timidly walked into the room with the dinner. They both looked gorgeous. Kerry had beautiful, medium sized, bouncy breasts and Megan had very large, but still upright, breasts straining against the fabric. I instructed them both to stand in front of me while I looked them over. That made them nervous, but they complied. Then I had them serve me dinner, and for desert I had Kerry sit on my lap and feed me. I stroked her legs and then slid my hand under her nightie and started rubbing her breasts. She responded with a moan and I continued for a few minutes. Then I said it was time for the after dinner show. I kept Kerry on my lap and kept fondling her breasts, but I instructed Megan to walk over to the area in front of us. I told her to take off her nightie. She did, and looked even better in just her panties and heels than she had in the nightie. Then I had her turn around and appraised her from behind. I had her lean forward and arch her back. After a minute I told her to take off the panties. She slid them down, still facing away from me. Once they were off I told her turn and face us. She looked so vulnerable and nervous standing there that I was getting very hard and was squeezing Kerry's nipples harder.

Then I instructed Megan to rub her breasts for me. She complied, and even let out a little sigh of pleasure. After a minute I told her to masturbate, but not to come. She shyly complied. At first it was very mechanical, but after a minute she started to get more aroused and started moving her body in rhythm and moaning. Then I told Kerry to stand up and take off her outfit too. She did, and I reached out and started rubbing her ass and tits while she stood in front of me. I slid a hand over her pussy and she quivered. I told Kerry to go over and suck on Megan's tits while she masturbated, and I reminded Megan not to come. I was very horny watching the two girls together, and I called Cindy over. Cindy was wearing a short dress, and nothing underneath. I had her replace Kerry on my lap and started kissing her and touching her through her dress. Megan was audibly struggling not to orgasm, so I told her to stop touching herself. I told her to get on all fours on the floor and I called Kerry back over to me. Megan looked incredible on her hands and knees like that. She was still heaving slightly from her arousal... I grabbed Kerry's tit in one hand while I was touching Cindy's breast through her dress with my other.

Then I opened up a box that was next to me and took out a dildo. I handed this to Kerry and instructed her to fuck Megan with it. She looked entirely shocked, but slowly walked over to Megan and kneeled behind her. I told her to suck on the dildo first to lubricate it. While she was doing that I told her to touch herself too. Then I had her push the dildo against Megan's pussy. Megan's whole body was blushing. She clearly felt a wave of shame for what she was doing, but she didn't protest. Kerry started to push the dildo into Megan. At first she moved it very slowly and Megan just looked like she was concentrating. But, after a minute she started to pick up speed and Megan started groaning. Megan's noises seemed to stir up something in Kerry because she started to go after her own pussy with her hand much more aggressively. Megan started to push her body back onto the dildo, getting more and more excited. I was incredibly turned on and I reached down and pulled Cindy's dress off. Once she was naked on my lap I started rubbing her entire body and she started rubbing her naked ass back and forth on my lap.

Megan came loudly, and slumped forward. Kerry didn't stop touching herself because she was very close as well, and I told her to suck the dildo clean while she finished herself off. She complied and it looked very hot. Cindy was pretty aroused too by the sight and my hands working all over her body. She asked my permission to touch herself, but I refused. Kerry came and dropped the dildo. Megan was lying on the floor face down, and I told her to roll onto her back. Then I had Kerry lie face down on top of her. Their exhausted bodies were pressed up against one another, and their tits were squashed together. I told them to kiss each other. They complied, and after a minute they started to squirm around a little bit, clearly getting aroused again. Meanwhile, Cindy was doing some squirming of her own on my lap, longing for me to give her clit my full attention.

Instead I told Cindy to get on to the floor in front of me and pull my pants off. I took of my shirt while she was doing that and she started stroking my cock. I told Kerry and Megan that I wanted them to rub each other's breasts while they kissed, and I guided Cindy's mouth to my cock. Megan and Kerry were getting more and more aroused, and Cindy was greedily sucking my cock. After a minute I told Kerry to slide up Megan's body and position her pussy over her mouth. I noticed Megan sucking on Kerry's tits as they passed by. Then I told Megan to use her mouth on Kerry. Kerry was clearly having mixed feelings. Humiliated and turned on at the same time. She looked amazing straddling another woman and squirming around in pleasure. I pulled Cindy's head back and walked over in front of Kerry. Without having to be asked Kerry pulled my cock into her mouth and started sucking on me. Kerry was already very close to orgasm and came soon after she took my cock in. I pulled out of her, and turned her around, still over Megan's mouth. I pushed her forward on top of Megan and told her to return the favor. After giving her a very brief break, I told Megan to start working on Kerry's pussy again. I positioned myself behind her and Megan grabbed my dick and slipped it up against Kerry's pussy. She was licking up and down the length of my cock and Kerry's pussy in one long stroke. I gently slid all the way in and started moving in and out. She began to thrust against me as Megan licked at her clit, and she at Megan's.

Cindy was sitting over in my chair touching her breasts. She asked again if she could touch herself, but I again said no. I pulled out just before I came in Kerry and sprayed my load all over Megan's face and Kerry's pussy. She and Megan both came before I was done. I lowered my cock to Megan's mouth and made her suck me clean, and then went back over to the table leaving them in a pile. Cindy looked desperate to come, but I was already flaccid. She slid back down to the floor and started gently licking my cock hoping to revive it. I watched as Kerry and Megan held each other tightly as the post orgasmic waves rippled through them. My cock started to stir. Finally, Cindy managed to get me hard and slipped me into her mouth. She was rubbing her tits, her ass, and her stomach and thighs as close to her pussy as she thought she could get away with. I ordered Cindy to lie back on the table in front of me. Then I called Kerry over and faced her away from me, standing up facing Cindy as she squirmed on the table. I leaned her forward until she was lying on top of Cindy. Their breasts were squishing up against one another and they were both squirming against each other's bodies. Kerry started kissing her, and she responded. They started sliding around against one another as I slid my cock into Kerry's pussy from behind. I stroked in and out of her a few times shoving their bodies together with each push. I noticed Megan was leaning over a chair next to the table using the dildo on her pussy from behind.

Cindy was whimpering with frustration. Everyone else had cum several times and she had yet to be touched. I pulled out of Kerry, and she pushed back against me not wanting me to stop, but I pulled away. 

Cindy asked, begged really, for me to fuck her, or touch her, or at least let her touch herself. 

I said "no, you cannot touch yourself, and I won't, but if you want, you can have the dildo inside of you." 

She said, "oh, yes, please!'. 

I said ok, but the only condition is that Megan will be the one holding it. 

She just half squealed, "whatever, I don't care. Just put it in me." 

So, I asked Megan to come bring the dildo back over and she did. I had her kneel in front of me facing the girls and slide the dildo into Cindy. Cindy moaned with relief and pushed back hard against it. Kerry started kissing her harder and hard and squirming around more and more excitedly on top of her.

I stood back, still rock hard, and watched for a minute. This really was something else.... Cindy, who supposedly wasn't interested in women, was squirming around naked beneath one naked woman while another fucked her with a dildo. Cindy came almost immediately and I told Megan not to stop. After just a couple of seconds Cindy was pushing back against the dildo hard again and starting to build to a second orgasm. I grabbed Kerry's hips and lifted them up and back so her knees came up on the edge of the table and her face was against Cindy's breasts. She started sucking on them and I started rubbing her ass and pussy while they were sticking up in the air. Then I slid her hand back to her own pussy. Megan needed no such guidance, as she was already energetically working her own. I went over to the table and grabbed a second, larger dildo. This one was meant to stand on the floor, and had it's own base. I slid it under Megan and reached around and started massaging her gigantic breasts while I pulled her hips up and positioned her over the dildo. It was maybe 2 feet long, so the person using it wouldn't have to get right down on the floor, so when she slid up her mouth was level with Kerry's pussy which she started licking as soon as she was there.

I slowly started sliding Megan down onto the dildo. It was rather large, so she was struggling with it, but she was just horny enough to try. She pushed hard against it and it slipped in farther. After a minute she started sliding up and down on it getting more and more excited once again. At the same time she was pushing the other dildo harder and harder into Cindy, and licking Kerry's pussy when she could. I stood back and watched these three women, all basically completely in the sway of lusts that they never really knew they had. Doing anything whatsoever to get themselves off. Finally, Megan and Cindy came and Megan slid off of the dildo and slumped over. I pulled her head into my lap and she idly licked me while I watched. Just enough to keep me hard. Cindy was still sort of in the aftershocks of her second orgasm, and Kerry was just building to her latest one. Cindy reached around and started rubbing Kerry's ass with one hand and her tits with the other, and pulled her back up so they could kiss. Kerry had her hand between their pussies stroking her own.

When Kerry finally came, I helped her up off of Cindy and took Cindy's hand and pulled her up. I lead her back into our bedroom and told the girls to clean everything up before they went to bed. In their room, I had a regular camera set up as well as audio. So, Cindy and I were lying in bed holding and fondling each other when I turned the TV on to watch what the girls were doing. There were both still naked and laying in the bed together, obviously a little uncomfortable about what they had done to each other earlier. They alternated between rationalizing it, talking about the money, getting embarrassed, and talking about how they would never ordinarily do something like that. To our amusement, though, Cindy and I watched them slowly slipping closer to each other in bed, and after about half an hour they were stroking one another. Eventually they ended up touching themselves and one another. Cindy and I watched for a while and started getting excited again ourselves. We ended up having sex again. 



Hiring Cindy Ch. 06



6: The punishment

In the morning I was the first to wake up and I went to get myself a cup of coffee. When I went through the dining room I was stunned to see that the girls hadn't cleaned it up at all before going off to bed. I was pissed and marched back into my room to tell Cindy. She was very surprised as well. I told her that I was going to have to punish them very seriously if they were to have any chance of staying on for the whole week, and for Cindy to get her bonus. I told her that she would need to help me punish them. For the day, I said that I would share my power with Cindy. Cindy would, of course, still have to do anything I say, but the girls would have to do whatever she said too. I said that I would be punishing them very severely today, but that I would need for Cindy to help punish them as well, and that if she didn't come up with humiliating, embarrassing enough things I didn't know if the girls would be able to redeem themselves. 

She didn't really seem to get what I was looking for exactly, but I said that I would start it out.

I told Cindy to put on the short leather tube dress and black fishnet stockings since she was a dominatrix now. We laughed about that, but she did put it on along with an incredibly high pair of heels…

Once she was dressed I sent her down to wake the girls up and I watched on the TV. She walked in quietly and ripped the blanket off of the two naked girls before they heard her. 

They were startled and she laid right into it- "master gave you an order last night and you failed to obey it. This is taken very seriously in this house and you are both going to be severely punished immediately. Get out of bed this instant."

They both jumped up, more startled than compliant. The scene was very erotic I must say…. When the two of them were standing, she immediately ordered them to kneel with their heads on the ground and their asses sticking up. I was pretty surprised, but I guess by now Cindy knows what I like… Then she took out the riding crop she must have grabbed on the way down, and gave each of them a few strokes. They seemed pretty soft, but very erotic none the less.

After she finished that, she told them to stay as they were until she came back to give them their next punishment. Then she left and came back to see me in the bedroom. We watched them for a few minutes until Cindy started stroking my cock again, and ended up sucking me off while we watched the two girls with their asses sticking up in the air. Almost right after I came in her mouth, Megan got out of the position and sat back normally.

Kerry said something about how they're in enough trouble already, but Megan asked how we would know anyways. And Megan said that she needed to take a leak… Cindy was actually mad that Megan had disobeyed her as well now… I found the whole thing really exciting to see Cindy getting into the role so easily…

I told her to get them and bring them up into the living room where I would meet with them. I saw her come on to the camera just seconds after Megan hopped back into the position. This time she had with her two collars and leashes! She put one around each of their necks and said to come with her. When I came out into the living room they were both in the position again with their naked asses facing me and Cindy standing on the other side of them holding the leashes.

I explained that I was incredibly disappointed in both of them for not following my instructions about cleaning the dining room, and that Megan would go even farther this morning and disobey Cindy's order to remain in position was too much. 

I said that I was very torn between sending them both on their way right now and trying to give them a chance to pay for what they did and keep going. 

They both begged me to let them keep going, said how much they needed the money, how they would be very well behaved from now on, etc. 

I said that I was serious. Today, as punishment and for them to prove their loyalty again, I would make them do many things that they might find shocking, but if they even hesitated once, they would be sent home.

They said that they understood. 

I said that the same authority extended to Cindy. Today, they were not to do anything unless I told them to. They were not to touch themselves, talk, eat, go the bathroom… Nothing. I asked again if they understood and accepted the situation. They both said yes.

So, first I had them clean the dining room as I had instructed them to do the previous night. I had Cindy supervise, finding tiny spots of dust and whatnot and making them clean the entire floor, naked, on their hands and knees with rags. When they were done with that, I said, well the next thing I need done is some yard work. They both looked very nervous, but didn't say anything. I took their leashes and headed for the back door. The back yard was pretty isolated. You could see into it from three of the neighbor's houses though if someone happened to be at the right window. I walked them out into the back yard leading them by their leashes. They were clearly very aware of being completely naked, and in a degrading situation while outside. Then I went and collected a rake, a little gardening shovel, and a lawn mower. I gave them a list of fairly dirty jobs and then I went and had a drink with Cindy by the pool while we watched them doing the yard work. It was strangely exciting and I was getting hard just watching them.

I noticed that Megan seemed a little bit uncomfortable, and suddenly I remembered what she had said about how she needed to take a leak, but we hadn't even given her a second to take care of that… That started to give me ideas, and I had Cindy bring each of them a very large glass of water and order them to drink it. Ostensibly because yard work was dehydrating… They were clearly very uncomfortable with the prospect of being seen by the neighbors, naked, wearing collars, and doing my yard work, but they were doing a reasonably thorough job, so apparently the appreciated that I was serious.

When Cindy brought them the glasses of water, Megan looked very scared. She took the glass obediently, but just took a very small sip of it at first. 

In a very firm voice, Cindy explained that she was going to bring the glasses back to the house with her and they were both to drink the entire glasses immediately. Megan started to object, but restrained herself when Cindy shot her a very scary look.

She drank about two thirds of the water before she burst out "I can't, I have to pee or I'm going to explode!"

Cindy, suddenly a pro at this, said "you will drink your water, and finish the yard work you were assigned, and then we may let you pee. Understood?"

Megan, looking dejected, slammed the rest of the water and started working on the yard work as quickly as she could. After about 30 minutes they said that they had finished. I told them to wait in the yard for a minute and that I would come inspect. I finished my drink at a leisurely pace, and then went down. I led them around the yard on their leashes inspecting very carefully. By this point, Megan's knees were pressed together and she was having trouble walking.

I found a couple of minor things and made them finish the jobs. I swear I thought Megan was not going to be able to hold it, but she did. While they were doing the final touches, I noticed the shades move in one of the windows. I looked up and realized that someone was peaking out through the shades in one of the neighbor's second story windows. That just urged me on…

When they had finished, Megan asked if she would be allowed to pee now. I said that there was one more thing she had to do and then I would let her pee. I told her to get down on all fours in the middle of the yard and I went back inside. I grabbed the dildo and brought it back out and gave it to her. I told her that she would not be allowed to pee until she had made herself come. 

She looked scared, and upset, and unsure whether or not she could hold it through something like that, but she took the dildo and started rubbing her clit to get herself ready. After a few seconds she slid the dildo inside of herself, reaching around behind. She started pumping it into herself, doing her best to stifle the mixed cries of pain from her bladder and pleasure from her pussy. She came after a few minutes, and was visibly on the brink of losing control of her bladder. She started to stand up and head for the bathroom, but I stopped her and told her that I didn't say she could get up. 

She said "you said I could pee when I came!" She was almost sobbing. 

I said, "Yes, I think I will let you, but I want you to keep touching your clit while you do it." 

She shrieked, "What? You want me to pee here? In your yard?!" 

I said, "Yes, you have not earned the right to use my bathroom yet after your disobedience." 

She started to cry and I loudly reminded her that I had told her to touch her clit. She started touching he clit while she was crying. I think she was trying her hardest not to give in, but it had just been too long and with an exasperated grunt she let loose. Piss ran out of her, down her legs, up the arm that was touching her clit.. Everywhere. But, I have to give her credit. She didn't stop touching her clit until well after she was done when I told her that she could. Even after I told her that she could stop, she stayed on all fours, soaked in her own piss, breathing loudly until I told her that she could get up. Her face was bright red and her face was streaked with tears.

I told her to go downstairs to their shower and clean herself up, but to be quick about it. I took Kerry's leash and led her back inside with Cindy and I. When we got into the living room, I told her to kneel in front of me and I took my cock out and had her suck on it for a few minutes, but I stopped her before I came. Then I told her to straddle the floor-dildo and fuck herself on it. She did as I told her to and I allowed her to cum. As she was finishing, Megan came back into the room, still naked, and looking much better than before. After she had recovered I told her to get off of the dildo and made them both stand next to each other. At this point, Kerry said that she had a request. I asked what it was. 

She said that she was afraid to ask, but she really had to pee as well. 

I said, "Ok. Given that you, unlike Megan, stayed in the position when Cindy told you to, and thus far today have obeyed every instruction, I will allow you to pee in the bathroom. But not just yet. First, I would like for the two of you to clean it very thoroughly."

I sent them both into the bathroom to clean it. They were crawling around on their hands and knees scrubbing nasty little corners and whatnot. Kerry was starting to look pretty uncomfortable herself now, so I decided to milk it for a while with 'white glove' tests and whatnot, until she was clearly on the brink of losing control. Finally, I said that it was acceptable, and now I would let her pee. She moved towards the toilet and started to push Megan out so she could have some privacy, but I stopped her. 

I said, "No, I think you deserve to pee in the bathroom, but I'm not convinced yet that you deserve to use my toilet." 

She looked stunned and scared… I told Cindy to go grab me a folding chair from the other room. When she brought it back Kerry was pressing her hands both against her pussy to help control the pressure… I set the chair up in the middle of the bathroom and told Megan to sit in it. She did, both of the girls looking very confused. Then I told Kerry that since she was doing so much better than the slut Megan, she would be allowed to use her as her toilet. The both let out a little gasp, but managed to control it…. It told Kerry to sit on Megan's lap. She did, but didn't let go. I told her that she was to pee now, but that neither of them would be allowed to get up until Megan had made Kerry come with her hands. Megan started rubbing Kerry's clit and Kerry sort of started uncomfortably moaning and shifting around. I warned Kerry that if she came before she peed there would be serious repercussions.

She was clearly struggling with the decision and the will power it takes to do something you've been trained not to do your whole life, but after a couple of minutes she let go and pee ran down her legs, Megan's legs, and onto Megan's pussy and stomach. They both let out incomprehensible noises of disgust and shame, but Megan kept working Kerry's clit the whole time. Once she had let go, Kerry seemed to get much more aroused and started to near an orgasm. I told her she was not to cum yet, and unzipped my pants and put my cock in her mouth. I told her that I was to cum before she did. She was already very much on the brink of orgasm, and I told Megan not to slow down with her hand or she too would be punished, so it was a struggle for her to control herself, but she did a very good job on my cock and brought be to orgasm fairly quickly. I pulled out at the last second and came on her face, chest and hair, and a few seconds later she let herself go over the edge.

I stood back and admired the scene for a minute… Two gorgeous women, with my cum, and Kerry's piss all over them. Man, that was something to see…

Then I told them to clean up the mess that they had made of my bathroom before cleaning themselves up, and then I sent them back to their shower to clean up. When they were gone I told Cindy that I would like for her to take charge of them for a couple of hours. She agreed, and when they came back from their shower, still obediently nude, she had them do a variety of jobs around the house. At one point she ordered Megan to alphabetize the spice rack while Kerry ate her out, which was kind of creative…

Later on she had them cooking dinner and Cindy and I had some time alone. I asked her if she was enjoying having two slaves of her own. She giggled and said that it was fun. I said that she should remember that they are here to please her, and that she should feel absolutely free to tell them to do whatever she wants. Anything she desires… She sort of giggled and said that last night was fun and all, but she really is much more attracted to men. I said that she could suit herself, but that this was a once in a lifetime opportunity so she might want to seize it and be creative. She agreed, but I didn't really know if she had anything in mind.

The girls served us dinner, and while we ate I instructed them to 69 each other on the table. After dinner, I left them in Cindy's capable hands again and I went off to do my own thing for a while. It appears that mostly she just had them cleaning, doing mildly embarrassing things, cooking, and the like. But, at one point I was checking it out on the cameras and I saw her have them both bend over the counter next to each other. Curious, I watched more, and she proceeded to produce both dildos and push one into each of them at the same time! That was pretty exciting, and I took it as a pretty good indication that Cindy was started to get excited about all this. I watched, and it looked like she actually made them cum. Afterwards, I saw that Cindy went back to her own room and masturbated! She really was starting to get turned on by these women!

That evening I called the girls into my den and instructed them to both kneel facing each other. At first I just had them kiss and touch each other, but then I took the two dildos and put one beneath each of them and ordered them to fuck themselves on them. They were touching their clits while they pumped up and down on the dildos. Kerry was on the longer one, so she had to lean forward to kiss Megan, but it worked out. Then, I took off all my clothes, and walked over and stood between them facing Kerry. First I made Kerry start sucking on my cock, and then I told Megan to stick her tongue as far up my ass as she could. She hesitated, but did it. It felt great, having both areas stimulated at the same time… I was in heaven. I think Kerry came first, then Megan, and finally I did. Very satisfied for the night, I told them that they had both done very well today, and that I considered their punishment to be done. I sent them to their room and I went to bed.



Hiring Cindy Ch. 07



7: The Girls Go Out

The next day I left them in Cindy's hands most of the time, except when I fucked Megan and got a blowjob from Kerry. In the afternoon, though, I called them all three together. I said that we were going out that night, and they needed appropriate clothes. Cindy obviously had plenty to choose from, but I had decided that Kerry and Megan were going to make their own outfits. They looked puzzled, but I told them that I had the appropriate materials, and I knew exactly what I wanted. I gave Megan a square of light patterned fabric, and two strips of spandex to Kerry. They both looked at me kind of quizzically, but I explained what they were going to do. Megan was going to wear the fabric as a dress. She was to wrap it around herself in one piece. Kerry had a little bit more complex job. One of the strips was to be a tube top, and the other she had to make into shorts. They both looked kind of hopeless. I said that I expected to see them upstairs in the outfits in 2 hours. I said that they would only be allowed to wear a pair of heels and the fabric I had given them of course.

I went upstairs, leaving them to see if they could figure out a way to avoid indecency laws with those materials… Two hours later, they came upstairs wearing their new outfits. It had worked out exactly as I had hoped. Megan's wrap essentially stretched from about ½ an inch above her nipples down to maybe just above the bottoms of her ass cheeks. It was not quite long enough around either, so there was basically a big slit up the right side that was held together by string that I had given them. She was very nearly bursting out of the thing in every direction. Kerry had actually shown herself to be a fairly decent seamstress. She had made the top easily enough, just sewing the ends together, but the strip I had given her was only maybe 4 inches wide, so her cleavage hung out both on the top and the bottom. The shorts were where the real talent came in. There was not much material for them, but she had managed to cover herself and fashion actual shorts out of it. They were extremely tight, and only came down about half way over her ass cheeks. Kerry looked really slutty, but she didn't look like she was wearing something so home made as Megan did.

They both said that they didn't think there was any way that they could go out in these outfits. I said that, first of all, they were totally free to quit and leave at any time, and I would even give them $5,000, which I wasn't really obligated to do. But, I said that I knew of a club where women often went in much more revealing outfits than these, even topless sometimes once they got inside. And, if they were interested, I could give them ecstasy to help them get over their self consciousness. Kerry visibly perked up at the mention of e. She said that she loves e, and would definitely like some. Megan looked more nervous. She had never done it before, and wasn't sure it was a good idea. I said that it was totally up to her and she could just let me know if she wanted one.

Half an hour later we all went out to the limo. Cindy was dressed very sexily as well. She was wearing a short red dress with nothing underneath, and looked fabulous. The other girls looked very sexy, but bordering on ridiculous in their home made outfits. We drove to a club that I knew of, which was indeed a very open place with lots of semi-exhibitionist women frequenting it. When we walked in, there definitely were many girls dressed in similar outfits to what Cindy was wearing, but Kerry and Megan were on another level altogether. Megan was having a lot of trouble already with her outfit. When she would walk she basically needed to use one hand to keep the back down and the other to keep the top up. Kerry's outfit was less precarious, but didn't leave much to the imagination either.

Kerry, Cindy and I all took an e right away, but Megan wanted to wait. We all danced and talked and whatnot. After a while, Kerry and Cindy were really starting to come up on their e, and both got a lot more relaxed and really started having a good time dancing. Kerry looked great dancing in her tiny outfit. Megan was a lot more uncomfortable. Finally, Kerry convinced Megan to try the e. I gave her one, and we all hung out for a while longer. After about an hour, Megan was starting to seem kind of out of it from the e, but she was having the time of her life. She was dancing very erotically by herself, or dancing up very close with Kerry. Cindy was mostly hanging very close to me and being very affectionate. I started to notice that in her condition Megan wasn't doing as good of a job keeping her outfit in place…. The top would slip down, showing a nipple for a minute or two at a time. Sometimes she would sit in a way where you could see half of her ass hanging out the bottom of the dress. It was very erotic for me… Every guy in the club was watching both of them closely.

After another hour, something seemed to have happened to Megan's dress. The seams she had made on the side with the string were coming apart. Now she had to really focus to keep the dress on while she danced, and with the e and all it was not the easiest thing to do… The slit on the side was very wide now. Maybe 4 or 5 inches. When she lifted her arm on that side you could actually see the side of her cleavage as well as the top, which really looked great. On the bottom the situation was even riskier because with the dress being so short, the slit made it very loose and it was flapping all over the place. I'm quite sure at least some of the guys in the club got a good look at her pussy for a second here and there. Anyways, they were still dancing, and Kerry and Megan has started dancing erotically with each other, heavy petting, making out and everything. Nobody in the whole club was missing it. It was getting me very turned on as well, and I started fondling Cindy who was sitting next to me.

Then I called the girls over and gave them an assignment. Each of them was to make out with at least 5 men during the next 2 hours. The impact was probably softened by the e, but they both just headed out to find the right guys. I saw Kerry making out with a good looking dude right away. His hands were all over her ass and tits, and she was definitely not resisting. A few minutes later, same deal with another dude. I wasn't sure where Megan was, so I figured I'd go look around. I saw her on a couch in the corner with a dude. He was openly rubbing her breasts. The nipples were still under the dress, but with the low cut and the slit on the side, that was about all that wasn't exposed. I watched as he started rubbing her thigh before I went back to sit with Cindy. By the end of the 2 hours, I think Kerry had made out with, and been heavily groped by, about 8 guys. Megan had only been with 3, but I think she had gone much farther with each of them, so I figured that counted. 



Hiring Cindy Ch. 08



Chapter 8: The Girls Come Back

Then I gave them their next assignment. They were each to bring 3 men back to my house for the night. The looked a little surprised and wary about this assignment, but went off to talk some of the guys they'd been making out with into coming back to party.

Once they had rounded up 6 guys, we went out to the cars. Megan and Kerry each rode with a couple of the guys and we all caravanned back to my place. I saw Megan in the back seat with one of the guys and her dress was practically off. Her breasts were entirely out and the guy next to her was making good use of the situation from what I could see.

When we got to my place, I invited the four guys to take a seat, and told Kerry and Megan to stand in the center of the room. Then I very simply told them to take off their outfits. They were uncomfortable with the idea of being naked in front of all these guys, but with the e, and everything they'd already been through, they went along and stripped naked. The guys were hooting up a storm... Then I told the girls to get the party started with each other and they started embracing, kissing and touching each other. It was very hot, and a couple of the guys stood up and started walking towards them. I told the girls that I thought the guys needed some attention, and had them kneel. I told each girl to take 3 of the guys and suck on each of their cocks, one at a time and use their hands on the other two. The guys quickly played along, and soon they all had their dicks out, and the girls were greedily sucking them off. The girls would each suck on one cock for a minute or two, while massaging the other two with their hands, and then they'd switch over to another guy.

Cindy and I were making out and groping each other watching this all take place. Then I told Cindy to change into her loincloth. At first she was taken aback, not wanting to jump into the middle of a gangbang, but I cajoled her into it. She came back a few minutes later with nothing but the little square of cloth covering her pussy. A couple guys broke off from the girls that were working on them, but I stopped them and brought Cindy over to where I was sitting. First I made out with her standing and groping her exposed ass and tits. Then I sat her down straddling me and we started grinding up against one another.

I noticed that one of the guys was lying down next to Megan and encouraging her to mount him. I told her to do it, and she stopped sucking on the other guy's cock and positioned herself above the guy lying on his back. She easily slid her pussy down onto the guy's dick and started thrusting up and down. Another guy moved around in front of her and she sucked on his dick while she fucked the other guy. She reached out and grabbed the third guy's dick and held it while she worked the other two.

One of the guys that Kerry was holding walked around behind her and pulled her hips up so that she was on all fours. Then he kneeled behind her and she reached down to guide his dick into her pussy.

Cindy and I were getting pretty heavy too, and as I started to take off my shirt she reached into my pants. I unbuttoned my pants and took them off. She got back on top of me and I could feel her pussy pressing against my cock. I had never had sex in front of other people before, but I was horny as hell thinking about it. I slipped inside of her and we both started moaning loudly. I was fucking her very slowly, wanting to make it last as long as possible.

The guy that was in Megan's hand was looking kind of frustrated. With everything that was going on, she didn't have the wherewithal to really do anything for him. He pulled back and walked around behind her. As he leaned forward behind her and lined his cock up with her ass, she let out a muffled "no" around the other guy's cock. But, she didn't resist, and he started to push into her ass. She let out a couple of whining noises as he worked his way deeper inside of her, but after a few thrusts she was moaning with pleasure again. Her moans became incomprehensible grunts, and she was bucking wildly against all three of the dicks that were inside of her. Eventually, all four of them came.

Kerry didn't let the guys take her all at once like Megan did. Instead, she let the guy fuck her doggy style, and both of them came. When he pulled out, she pulled the guy that was in her mouth down and laid him on his back. She moved over to straddle him and pulled the guy she had been holding in front of her and sucked on his cock. After the guy beneath her came, she laid down the third guy and fucked him. Overall, I think she had two or three orgasms fucking them.

Three of the guys got up right after they came and started getting dressed. As they left, the other three guys were laying on the floor with the girls fondling them and watching Cindy and I. I was pushing in and out of Cindy very slowly, but she was rising to an orgasm. She whimpered and finally screamed as she went over the edge. I managed to hold off, and just kept up fucking her slowly while the others watched. At first, she was a bit overwhelmed by the stimulation right after her orgasm, but after a minute she started to build up again. She got very close, but I came before she could. She lets out a frustrated sigh when I pull out of her.

The five naked people on the floor started to get a bit more aroused from all the touching, and one of the guys started to rub each of the girl's pussies. After a minute, they were clearly all five getting horny again. Cindy was squirming around next to me, still very horny after she couldn't reach orgasm the second time, but I was spent.

After a few minutes, I told Kerry and Megan to stand up. They took their time, but eventually pulled themselves free and stood up. I beckoned them over to the couch and told Megan to lie on her back. When she did, I told Kerry to 69 Megan. They complied, and I told them that I wanted them to clean out each other's pussies. Cindy was straddling me again next to the girls. I guided her to stand up in front of me facing away from me, and I addressed the guys on the floor.

I told them "That these two (gesturing at Kerry and Megan) are sluts, and they are to be used however the guys pleased. But," I said, gesturing at Cindy, "this is my queen. She is to be respected and treated like a lady." 

Cindy shot me a glance, nervous about what I was going to do. While was talking, two of the guys were stroking their cocks, and watching as Megan and Kerry started to moan and squirm around louder and louder next to me. I reached up and untied Cindy's loincloth and let if fall to the ground.

Then I explained to the guys that I would let them touch Cindy, but only if they were nice about it. I said that they would not be allowed to touch her pussy or fuck her, and that she would not suck them off. They agreed, and I pushed Cindy lightly forward. She walked into the middle of the room and the guys circled around her. One guy started kissing her and massaging one breast while another sucked on the other breast. The third guy stood behind her massaging her back, ass and legs. She was moaning at all the attention.

After a couple of minutes, I asked the girls whether they had finished cleaning each other yet. 

Kerry pulled her face out of Megan's pussy just long enough to say "Yes master". 

I said, "Good, but I seem to remember that her pussy wasn't the only part of Megan that these men filled. Get up ladies." 

They stopped and stood up. I told Megan to bend forward and put her arms on the back of the couch, which she did. Kerry looked very uncomfortable with this situation, but I told both of them to touch themselves. I let them stay like that for a second, and then told Kerry to kneel behind Megan and clean her ass out. She hesitated, but then kneeled down and leaned forward. As she slid her tongue into Megan's ass, Megan let out a grunt of pleasure and started touching herself more enthusiastically.

Meanwhile, Cindy was writing around between the guys as they ran their hands all over her body. After a bit, she asked me for permission to hold their cocks, and I said that I would allow it. She grabbed two of their cocks immediately and started stroking them while the guys continued to touch her. I noticed one of the guys running his hand over her pussy, and I warned him to stop. Cindy let out a little sigh that sounded almost like frustration to me...

Megan came loudly next to me and slumped forward, but Kerry kept fingering herself trying to get off one more time. The guys Cindy was stroking were starting to moan, and Cindy was sounding more and more excited, while still frustrated at not having any direct stimulation. After another minute, Kerry came. Then, I told Kerry to go over and stroke the third guy, the one that Cindy was neglecting. She walked over and reached around him while he was still massaging Cindy's ass, and took his cock in her hand.

Finally, Cindy couldn't take it any more, and said "Please, master, I need you to fuck me!" 

I was very happy to hear that, but instead of obliging, I said that I would not do that. But, I said, if she wanted, I would let Megan eat her out. 

She moaned instead of replying, but after a few minutes, she screamed out, "Ok, fine! Whatever!" and I sent Megan over. 

Megan pushed the guys slightly to the sides as Cindy was stroking them and kneeled in front of Cindy's pussy. She started out by gently licking Cindy's stomach and thighs, and then lightly gliding over her pussy. At the same time, the guy behind her was rubbing her ass, and the other two guys were kissing her stomach, neck, and breasts. After teasing her for a while, Megan started eating Cindy out in earnest, and Cindy started moaning with abandon.

As Cindy started to get closer to orgasm, one of the guys she was stroking grunted and shot cum all over Cindy's stomach, her pussy, and Megan's face. Cindy seemed to get even more excited by this, and was writhing around desperate to cum herself. Finally, she came loudly, and at almost the same time, the guy standing behind her, who Kerry was stroking, shot his cum all over her ass and back. Megan stood up and pulled Cindy tightly up against her naked body until Cindy's aftershocks passed. Meanwhile, Kerry slid around the two and took the third guy's cock into her mouth, and he quickly came for her.

Finally, I told the guys that it was time to go home. They all were completely spent anyways, so they started grabbing their clothes. Before they put them on, I instructed to Kerry and Megan to make sure that they guys were clean before they got dressed, and each of them sucked on the guy's limp cocks one last time to clean them up. Then the guys left, and I told the girls to go get cleaned up, and then come back up to the master bedroom. Cindy and I headed up there directly, all four of us walking around completely naked.

That night the four of us slept together naked. I spent some time caressing their bodies, they spent some time caressing me and each other, and a couple of times I would guide one of their mouths down to my cock, but I didn't come in any of their mouths. Finally, in the morning I was rock hard again, and I asked both Kerry and Megan to suck me off at the same time. They both slid down my body and took turns sucking my cock into their mouths and licking the sides of it in unison. After a while I pulled Megan up next to me and flipped her on to her stomach and handed Kerry a bottle of lube. Kerry knew what to do and started to push the lube into Megan's ass. Megan groaned and writhed around a bit. Then I slid over on top of Megan and fucked her in the ass.

The girls were still around for a few days, but from there on out it was less intense. We spent a lot of time in bed naked, fondling each other in various combinations. Kerry ate Cindy out one night, I fucked all three of them a number of times, and I got a lot of blowjobs from all three. All three of us were recovering from the ecstasy, and we had pretty much filled up on the sickest of our fantasies....

The only event that sticks out was on the last night they were there. I ordered a pizza instead of asking the ladies to cook. Cindy, Kerry, and I were cuddled up on the couch watching a movie. I was dressed, and each of them was wearing a fuzzy, soft baby doll nightie that was short, but not really revealing. I was enjoying idly touching their bodies through the material. But, Megan had been in her room packing or something, and when she came back she was still naked from earlier when we had been fooling around. She asked if I wanted her to put on a similar nightie, but I told her not to. Instead I had her get on her hands and knees in front of us and masturbate for us. She did as I told her to, and just as she was starting to get worked up the doorbell rang and she froze. I told her to go let the pizza man in while I got the money together. She was clearly nervous doing that, but by that point she was used to doing stuff that made her uncomfortable and she walked over and opened the door wide and asked him in completely naked. He was a 20 something guy, and didn't look like an asshole or anything. At first he was stunned and didn't move at all, but after he caught himself he walked in and put the pizza on the table and mumbled something about $24. He was blatantly staring up and down Megan's body. I had my wallet out, and I handed him $24 even. Then I asked him whether he would prefer a normal, cash, tip, or if he would like for Megan to tip him personally. He immediately picked the later option with a big smile.

I went back over to the couch and cuddled up with the other two girls and we watched. Megan took a step towards the delivery boy, with the door still open out to the street a few paces behind him, but I told her to wait, and asked the other two girls what they thought Megan should do to tip the delivery boy. They both thought on it for a second, and then Cindy suggested that first she should kiss him and let him touch her. Megan complied and embraced him and started making out with him. The delivery boy slid his hands over her ass and breasts as they made out. Then Megan stopped suddenly, and turned to us and asked what we wanted her to do next. The delivery boy had a ridiculous smile on his face, and Megan looked like she was enjoying herself as well...

This time it was Kerry who made the suggestion. She told Megan to touch herself for the delivery boy. Megan turned to face him and started in on her pussy. The delivery boy took a step back and turned to take the site in, ad Megan started to moan loudly and buck her hips a bit. After a few minutes, Megan didn't stop herself this time, so I told her to, and she turned to us to await the next instruction.

This time I asked the delivery boy what he would like her to do next. He paused, and looked uncomfortable for a while. I used the pause to start kissing one of the girls and then the other, while my hands slide over their asses and tits over the fuzzy gowns, and they squirmed against me happily. 

After a few seconds, he turned to Megan and said, "Well... Um... Maybe, if you wouldn't mind, maybe you would give me a blowjob?" 

I said that I thought that sounded like a good idea, and Megan immediately went down on her knees in front of him and pulled out his dick. She used one hand on him as she sucked him into her mouth, and she used her other hand on her pussy again. As she sucked him off I started getting more and more frisky with the other two girls. Eventually, Cindy pulled my cock free from my pajama pants and started stroking it. Once I was hard, I put my arm around Kerry's waist and pulled her on to my lap facing away from me and towards the pizza boy. I pulled her fuzzy gown out from between us, and my cock was between her pussy lips and ass cheeks. She started sliding herself up and down along my shaft while I made out with Cindy and squeezed her ass. After a second, Kerry lifted herself up and slid me inside of her. At the same time, I slid my hand up under the back of Cindy's gown and massaged her naked ass while we kissed. After I got more excited I reached my other hand around Kerry's side and slid it up to her breasts, which pulled the front of her gown up above her stomach. The pizza boy could see her pussy, and my cock pushing in and out of it now, and he started to make louder and louder noises until he came in Megan's mouth and she swallowed it all up. A little while later Kerry and I came as well. Then the pizza guy buttoned up his pants again and left, thanking us all profusely on the way out. 

Before the girls left the next morning, I paid them as planned, and thanked them. They thanked me, and said it was the easiest, and most fun, money they'd ever made. I said that maybe we would have them back at some point, and they both said that they hoped I would! 



Hiring Cindy Ch. 09



Chapter 9: The Beach

The next month and a half after they left was very much more tame. Cindy and I were starting to act more like a normal couple than master and slave. We still had sex constantly, I still had her spending a lot of time naked and dressed up, but we spent a lot of time just relaxing, hanging out, going out to dinner, and so on.

A couple of times we went out for drinks and I had Cindy wear some over the top outfits, and a couple of times we played out little games at home, but nothing as exciting as the stuff with the girls. After that, we needed a break. But, about the time the eighth month rolled around, I was started to get a few new ideas...

One day, I decided to go to this 'clothing optional' beach I had heard about. Cindy put on her bikini, and I put on my suit and we drove out to it. When we got there, I was surprised by how crowded it was. Apparently the area nearest the parking was where people wore their suits, and the further down you went the less people wore. As we walked along, we saw a few women with their tops off, and towards the end two couples, and one shady looking old guy, that were totally nude. We set up our towel maybe 80 feet past the last nude couple. We laid down to get some sun and I told Cindy to take off her top, which she casually did. When we decided it was time to flip over on to our stomachs, I had her take her bottoms off too. I took the opportunity to help her put some sun block on, and rubbed it all over her back, the backs of her legs, and her ass. She pushed subtly back up against my hand when it was between her legs and I teased her a little bit. She seemed very comfortable being nude down here, since the other people were pretty far away, and the ones close enough to see where all naked themselves.

After a while we went out for a swim, and made out in the water a bit while I fondled her. When we walked back in, the nearest couple got a good look at Cindy's nude body, but she didn't seem to mind. We sunned for a bit longer, and a group of guys wearing their suits walked by along the water line and stared at Cindy. There were other nude women on the beach, but no one that looked anywhere near to as attractive as Cindy.

About an hour later, I told Cindy that I had just realized that I'd forgotten my camera in the car, and I asked if she would go get it for me. She sat up and grabbed her suit, but I stopped her. She looked and me plaintively, and said that she couldn't possibly walk past all those people naked. She protested that there must be 500 people between here and the car! I insisted that she do it, and reminded her that the whole area was officially clothing options. And I pointed out that we hadn't seen any kids or anything like that, so I thought it would be fine. She really didn't want to do it, but after having spent a couple months without really asking her to do anything intense, she decided to suck it up and do this for me. But, she insisted that I follow her from a discrete distance just to make sure she was ok.

She stood up and started walking back. Every guy, and most of the women, she passed, openly checked her naked body out. She looked very uncomfortable already, and we were still in the area with the nude and topless people. But, she pushed through and kept walking past more and more crowded sections. A number of guys whistled, or called things out to her. Finally we were approaching the really crowded part, where no one was topless or anything, and she suddenly turned and kind of hid behind a big scrub bush and waved for me to come over.

When I got over there, she pointed out a sign that I hadn't seen before that said that swimwear was required beyond that point. And she said that she just remembered that the car was parked on the outside of the lot, within sight of the street and a handful of shops. She protested that we had a rule that I wouldn't make her do anything that could get her arrested, and this definitely could. I had to admit that I saw her point. She had already been incredibly brave walking by maybe 100 people totally nude, and it had really excited me. So, I suggested a compromise. She still would have to get the camera from the car, and she still wasn't allowed to put on any clothes, but she didn't have to walk along the beach. She could sneak her way there. She could sneak around in the brush on top of the little sand hills, and she could do her best to hide between the cars. She objected, and we argued about it for a minute, but finally I convinced her that it would be possible, and wouldn't get her arrested. And I said that if she did somehow get arrested I would pay her and extra $100K on the spot. That was the final convincing she needed, and she headed out.

I followed her along the beach, but she was crouching and sneaking around among the brush on top of the little sand hills. Most of the time I couldn't see her, and neither could anyone else, but in some spots, I caught sight of her naked body sprinting across open areas. I noticed at least a few people noticing her as well. When we started to get closer to the parking lot the cover got less thick, and there were more people there as well. A few times, groups of guys got nice long looks at her as she scuttled along, and a few guys were openly whistling and drawing even more attention to her. Finally, she slipped into the parking lot and hid between two rows of cars. She ran around trying to stay low and out of sight as much as possible, but more than a few groups of people saw her as she made her way to the car. As soon as she got there she got into the back seat and hid down low until I came along and got in the front.

She was mad. It hadn't really worked out nearly as well as I said that it would, and she had been seen by tons of people! I calmed her down, and tried to convince her that no harm had been done. Ultimately, I grabbed a t-shirt that was sitting in the truck and let her put that on for the walk back. It didn't totally cover her ass, but someone she walked past would have probably assumed that she just had a thong swimsuit on beneath it or something. After a bit she calmed down, and I asked her whether it had been exciting at all for her, and said that I had loved every second of it. I was really horny. She impishly admitted that she was pretty turned on as well. She was lying down on the back seat now wearing the t-shirt. I told her that I wanted to see her touch herself. She slid the shirt up on to her stomach and started touching herself. At one point, a car pulled up next to us, and I told her not to stop. She was very close at that point, so she just kept in on her pussy. A guy got out of the car that had pulled in and did a double take. He stared for a minute, and then I heard his wife say something and we walked away starting back into our car over his shoulder. Cindy came right before he went out of site, and let out a loud enough grunt that he must have heard her.

After she had recovered, I grabbed the camera myself, and we headed back holding hands. As she walked, the back of her shirt would periodically blow up and people caught glimpses of her ass, but she didn't seem to mind much. When we got back to the sign about suits being required, I had her take the shirt back off, which she did grudgingly. I had her stand by herself for a minute, with her back to the more crowded section and took a picture of her. Once we got down to where more and more people were at least partially nude, I stopped and pulled her up against me and kissed her. While we were kissing, I slid my hand over her ass and she squirmed away from it. After a minute I stopped and we walked the rest of the way to our blanket.

When we were there, I had her pose on the blanket for a couple of pictures of her sitting there. After a few tame ones, I told her to get up on her hands and knees and I took a picture of her from the side. The more overtly sexual pose drew some attention from the nearest couple and the weird single guy.

After a couple more photos, we laid down side by side facing each other. My back was towards the rest of the people. I pulled her up against me and started touching her chest. I was blocking everyone's views, so she didn't protest as I started fingering her slowly. Then I took her hands and slid them under the front of my suit and she started stroking my cock. We kissed and fooled around like that for a while before she said that I should just take my suit off. 

"It is a nude beach after all!" I agreed, and let her pull it down and off.

She slid back up against me and started stroking me again. After a minute, I turned her around so she was facing away from me and positioned my dick between her legs. She reached down and lined me up with her pussy from behind, and I thrust it deep inside of her on the first stroke. I was pretty sure that the nearest three or so people could guess what was going on, but what were they going to do? After a few minutes, she started to moan pretty loudly, and I did as well. At that point, I figured the people that were nearest would definitely know what was going on.

So, I pulled out of her, and rolled on to my back. Having my cock visible to these strangers was kind of a rush for me, and I pulled her on top of me. I snuck a discrete glance at the nearest groups, and the three people were indeed watching us intently. I nudged her upright so she was sitting on my dick when it slid back inside of her. She kept nervously glancing back over towards the other people, but as we fucked she seemed to forget all about it. I noticed that the guy that was alone appeared to be jerking off himself. Just before I came, the group of guys that had walked past going the other way rounded the corner coming back! They were yelling things, whistling, and hooting, but Cindy didn't stop. She kept thrusting herself up and down on my cock until we both came and she slumped forward. The guys had stopped just down the beach from us to watch, but I said something about the show being over, and pulled the blanket over our bodies, and they started walking along the beach again.

We cuddled there for a while, went for a swim to rinse off, and then left. On the way back I let her wear her bikini this time. A couple months later, Cindy told me that that day had been one of the most exciting days of the whole experience. She said that it might even have been her favorite, despite her nervous complaining she had found it incredibly exciting. 



Hiring Cindy Ch. 10



Chapter 10: The Party

The rest of the months went by quickly. We were becoming ever more romantic. Despite the change in our mood towards a more normal relationship, Cindy's sexual appetite seemed to just increase and increase. She wanted to fuck all the time. She asked my permission to masturbate almost every day. Sometimes she used the dildo on herself. She was also naked by this point almost all the time that she was around the house. A few times I took her out in ridiculous outfits; once to the mall, once to a bar, and once to a nightclub.

The most exciting experience during these months was when we went to a strip club. I had her dress up in a total stripper outfit. It was this tiny micro dress that was basically just a super narrow strip of spandex around her ass and pussy that left a good portion of her ass showing, and a couple of narrow band that went up to the tiny bikini top. She wore the stereotypical stripper shoes- very high, platform, heels. Underneath she wore a very small, sexy thong. She wore a coat over the dress to get to the club, but left it in the car. I was very turned on watching her walk through the parking lot and past all the horny patrons. They all must have just assumed she worked there.

Once we were inside, I got a lapdance from a hot stripper. They are pretty touchy lapdances at this place, but they keep their bottoms on. After my dance, I had her give Cindy one, and they were even more touchy that the stripper had let me be. Afterwards I asked the stripper if she thought it would be a problem if my girlfriend gave me a lapdance. The stripper said that it was against the rules, but that so many girls worked there, and Cindy was pretty enough, that she thought people would just assume that she worked there.

With that, Cindy stood up and started dancing in front of me. She was very sexy. Slowly she stripped down to her panties, and slid on to my lap and started grinding against me. I think she would have let me pull her panties off, and probably even fuck her right there, but I kept myself under control because I didn't want to get kicked out... After a while, we left, and fucked right in the parking lot in the back seat of our car. A group of a few older guys walked past and saw us, which just turned us on more.

Anyways, other than that stuff, they were very nice months. I started to think that Cindy was really falling in love with me, and I was starting to feel the same way towards her.

Meanwhile, I was periodically emailing the two girls we had hired months earlier, and they would occasionally ask me if I wasn't interested in a second deal with them. Apparently they had told some of their friends about what they had done, and they told me one day that three of their friends from school had said that they would love to get involved as well. I asked them to send me pictures of the girls, and they sent a few pictures of all three girls together wearing bikinis and kissing a bit. All three were very much attractive.

Anyways, as the last month rolled around, I had another discussion with Cindy about her limits. I said that there was only one month left, and I still had fantasies that we hadn't been able to play out because of some of her limits about other guys. We talked for a while, and she admitted that she was a bit more curious, and a bit less nervous, about letting some strange guys get more physical with her. She said that she had loved having the guys touch her after the club that night. After a while we agreed that she was interested in taking it a bit further, but we agreed that I would keep in good touch with her to make sure that she was comfortable before going any further.

Mid way through the twelfth month there was a big conference was in town, and a ton of people I knew from work were going to be in town for it. Amongst them were the most of the six guys that had attended my dinner party. They started questioning me about whether or not I might have a couple of them over for dinner again, since they were in town. I agreed to have them over for a regular party instead of dinner. I invited a number of the guys that they knew too, since they had apparently already heard the story about the last one. Ultimately I had a guest list of 25 men, and even though I hadn't said anything, all of them seemed to assume it was going to have some sexy element to it...

I emailed the girls back and told them that I did indeed require their services. They were thrilled. But, I explained to them, this time it would only be for one night. I would give each of them $15K, and each of their friends $10K, to serve as hostesses for the party I was planning. Same basic rules as last time- any of them could leave at any point, but I'd only pay them if they stayed all the way through. They all five agreed to help me out.

On the morning of the party, they all five showed up at my house. They were wearing normal street clothes, but they all looked great none the less. The all helped put together the appetizers, get drinks, decorate the house, etc during the day. After dinner, I passed out what were to be their initial outfits. Each of them was to wear a very sexy, short, low cut, backless, tight, identical red dress, and matching red heels. I told them not to wear any stockings, or anything underneath the dress. They went off to get dressed, and done up. The three new girls were all visibly nervous and excited.

Meanwhile, I gave Cindy her dress. It was similar to the dresses the girls were given, except that it was ankle length. It had a long slit that came up to about 4 inches below her waist. She went and changed into it, and when she came back she looked great. The dress completely hugged her body, and made her ass look spectacular. The dress pushed her breasts up nicely too, and her cleavage looked extremely enticing.

A bit later, the girls came back in wearing their dresses. They all looked delicious. The dresses were indeed very short, and their legs looked amazing to me. We all finished getting the house ready for the party. As the guests arrived, I assigned the girls to meet them at the door, escort them in and get them each a drink. The girls flirted with all the guys, and the guys openly leered at them all. Everyone was having fun, drinking, talking, and listening to the music.

Once everyone was there, I turned the music down and made an announcement. I said that the reason for this party was to celebrate Cindy and my upcoming one year anniversary. They all applauded, and Cindy smiled. I said that this night was all designed for Cindy, and that I wanted everyone to show her the best time they possibly could. They all cheered, and some of them seemed to be taking a very lewd interpretation of my comments. I turned the music back up and walked around with Cindy on my arm greeting people.

We walked up to the ladies one at a time and explained to them that I wanted them to circulate, keep flirting with the guys and getting them drinks. I also told them that I expected them to react to anyone touching their asses or chests warmly and flirtatiously. I said that I did not want the girls kissing the guests or anything like that yet though. They all agreed, and I started telling some of the guests that they were welcome to get a little frisky with the help if they liked, but not to try to take off their clothes or touch their pussies or anything intense like that. The party went on for a couple of hours like that, and the guys got progressively more physical with the girls. They were all openly squeezing their asses and tits every time they walked past. Sometimes one of the girls would walk up to a group of a few guys to ask them what they wanted to drink, and end up with five guys caressing them all at the same time. They all reacted just as I had wanted them to. They giggled, didn't pull away, and did the whole "Oh, you guys!" kind of stuff. As time went on, some of the girls started periodically sitting on different guy's laps for a few minutes while the guys molested their breasts, and rubbed their hands all over their legs and asses.

Most of the time, most of the girls seemed like they were genuinely turned on by all the attention and fondling. At about one in the morning, everyone, including the girls, was starting to get pretty drunk, and things were getting a bit more heated up. More intense groping of the girls, more sitting on guy's laps, more 'accidentally' bending over too far and giving a bunch of guys a glimpse of their asses, etc. So, I decided it was time for the next phase. I called all of the girls into the kitchen and handed out different outfits for them to change into. These ones were red frilly baby dolls. They were completely transparent, and along with each one was a tiny red thong. Megan and Kerry didn't skip a beat, but the other three looked very nervous about really going through with something like this. I instructed them that I was also changing the rules a bit. Starting then, the guys would be allowed to reach under their nighties to touch their asses and breasts, but they were not allowed to touch their pussies or pull off their thongs. I also told them that they should kiss the guys now too, but they should not ever spend more than a couple of minutes with any one guy before moving on to the next. The three girls looked more apprehensive still, but I kept going. I told them to change right there in the kitchen after I left and come back out to bring the guys more drinks. With that I led Cindy back out, still in her long dress. Something about the idea of the five gorgeous women naked in the kitchen while they changed really got me horny.

Cindy and I milled around some more while the girls changed. It took them a while, so I was guessing that Megan and Kerry were spending some time convincing the others to go through with it. I passed on the new rules to the guys as we talked to them. One of them asked if the rules applied to Cindy, and I said that they did not.

Eventually, the girls came back out. Kerry, Megan, and the redhead were all looking very confident, and almost strutting their stuff for the guys. The blond and the brunette were looking a lot more uncomfortable, but came out and started circulating regardless. The guys let out a series of hoots and whistles for the girls when they came back in. They all looked stunningly sexy, and seeing all five of them together, dressed identically was a real turn on for me.

They moved through the crowd as instructed, and the guys took full advantage of the new rules. Sometimes they would be sitting on a guy's lap making out with him, and maybe even grinding against him a little bit. Sometimes one of them would end up in the middle of a group of guys that would pull their nightie up and all rub her breasts, ass, stomach, thighs, and legs at the same time. The girls would all smile and let the guys have free reign. Sometimes they'd even let out a little moan. When the blond or the brunette found themselves in one of these situations, they'd usually blush and freeze up, but the other three seemed to really enjoy the attention. Generally the girls were very good about keeping moving around so nobody was hogging them. The girls were fairly strict about enforcing the rule against the guys touching their pussies, but most of them would let the guys trace the line of their panties with their hands as long as they didn't go any farther then that. The guys were getting drunker and hornier, and the girls were all clearly getting more and more aroused too. The redhead seemed like she was seeking out groups of guys and kept finding herself in the middle of them being fondled from all sides.

At one point, I was sitting next to Cindy talking with a couple of guys when the redhead came by asking if we needed any drinks. The guys all took a quick squeeze of her ass, but then I pulled her on to my lap. She immediately started kissing me and I ran one hand up under the back of her nightie and started squeezing her ass while I ran the other up in front to her breasts. She moaned and started pushing her pussy up against me. After a couple of minutes, I reminded her of the two minute rule with a smile and sent her on her way.

After about an hour I gave the girls another instruction. Whenever they walked past one another, I wanted them to kiss one another, and touch. Some of them adopted this more aggressively than others, but it really got the guys excited... A couple of times, I saw two of them making out, and fondling each other. At one point, both the redhead and Kerry were caught in the middle of a group of maybe 8 guys. The guys started molesting them both, and pulled their nighties up to their necks. The girls looked at one another and pushed their bodies together, squeezing their breasts against one another while guys fondled them from both sides. The made out very passionately, and fondled one another. The skin-to-skin full body contact seemed to get them each even more aroused, and the guys smelled the blood in the water and got even more aggressive with them. After about 10 minutes, the girls finally stopped making out and moved on. It was quite hot, and Cindy and I just sat staring at them the whole time. After they moved on Cindy whispered to me that she thought that was incredibly hot, and was kind of jealous of all the attention they were getting. I assured her that when this was over, she wouldn't feel that way anymore.

Finally, at about 3 AM, I decided it was time. I took Cindy by the hand and lead her out into the middle of the room and asked the girls to join me. I had them turn the music down again, and asked if everybody was having fun. They all cheered and yelled out that they were. Then I asked what they thought about the girls, and they yelled even louder. Then I asked what they thought about the guest of honor- Cindy, and they yelled again, some of them talking about how hot she was and so on. Then I said that since this was her party, she was entitled to some special attention. With that, I signaled the girls to take off her dress. They grabbed it by the hem and pulled it quickly up over her head. As she wasn't wearing anything underneath, she was suddenly standing there completely naked in front of all the guys. That got her quite excited, and it certainly turned me, and the rest of the guys on as well. They all cheered again. I asked what they thought of her now, and they all yelled out things about her body, and how sexy she was.

Next I asked the girls to take off their nighties. They did, leaving them all in just the small red panties. But, Cindy was still conspicuously the only naked person in the room, and was enjoying all the attention it was getting her. Then, I said that I had a special treat planned for Cindy, and I whispered in Kerry's ear, and she went up to Cindy, pulled her body up against hers and started making out with her. I went around to the other women, and the blonde and brunette each went over and started sucking on one of her breasts. The redhead walked around behind her and started rubbing her body up and down against Cindy's. Megan got on her knees and slid in between Kerry and Cindy and started rubbing Cindy's legs and thighs. Cindy was in heaven. Almost every inch of her body had warm, sensual, skin caressing it. After a couple of minutes, Megan started teasing her pussy. Cindy reacted with a whimpering moan as Megan started in on her pussy with her tongue. Meanwhile, the redhead slid down her body and started kissing her ass and thighs. After a few minutes, Cindy was writhing around with total abandon. Excited by Cindy's arousal, the redhead started to push her tongue into Cindy's ass. Cindy immediately reacted with a scream of pleasure. She was obviously overwhelmed and out of her senses. She came just a second later, but the girls didn't stop until she had a second orgasm. After her second, the girls slowed down, pulled away from her ass and pussy, and were rubbing their bodies and hands all over Cindy's body while she recovered her composure.

Once Cindy regained her wits, the girls all stepped back and they guys broke out in another cheer. When they had calmed down, I said, "See how much these girls appreciate Cindy!" and everyone cheered. Then I asked whether the guys appreciated her that much, and the all cheered. 

Then I said, "Alright, well why don't any of you that want to show Cindy your appreciation line up here!" 

All of the guys cheered and lined up. The girls gathered between the guys and Cindy, and I said that they would be helping he the guys into the most appreciative state that they could for Cindy... Each girl took one of the first guys in the line by the hand and pulled them forward. Then they all kneeled in front of the guy they had grabbed and stripped them naked. Once the girls had their guy naked, they started stroking their cocks. After a bit, they would suck their cocks into their mouths. Meanwhile, Cindy was standing alone and naked in the middle, looking somewhat scared, but clearly overwhelmed with lust at the same time. The first girl led her guy over to Cindy as soon as he was hard. She guided him on to his back on the floor and nudged Cindy over him so that she was straddling him. Cindy and I had talked earlier, and she agreed that she wanted to try this out, but she was clear with me that she might freak out. The girl took hold of the guy's cock and guided it into Cindy's already soaked pussy. She stroked Cindy's clit for a second until she started thrusting up and down on the guy's cock, and then she went to get the next guy in line ready.

Cindy fucked the guy hard, and he came quickly, before she could come again. After she lifted herself off of him I whispered in her ear and asked whether she wanted more, and she said that she needed more at this point! So, I signaled to the girls that were warming up the next two guys. They brought them up and guided Cindy on to her hands and knees. Then one guy kneeled in front of her and she immediately took him into her mouth. The other girl brought her guy around behind Cindy and guided his dick into her pussy. It slide all the way in easily and he started fucking her roughly. Both guys came quickly. The girls were bringing them well along the way to cumming before they ever entered Cindy. But, two more replaced them almost immediately.

When those two came inside of her, they led out another guy and laid him on his back. Cindy moved to straddle him, but the girls stopped her and one of them poked a finger full of lube into her ass, and then they flipped her over above the guy. They held her by her hips and him by his cock, and guided it slowly into his ass. At first she pushed down on him very tentatively, grimacing, but after a minute she pushed him completely inside of her with a grunt. The girls moved another guy on top of her and he slid easily into her pussy. Another guy was brought around to the side where she could suck his cock. She was grunting and thrusting her body around like she had gone mad. It was impossible to tell how many orgasms she had in total, but at least four. The guy in her pussy pulled out and sprayed his cum on her stomach and she immediately reached down and started fingering herself through his cum. Next the guy in her mouth came, and she was so distracted that she didn't swallow it in time and it ended up all over her lips and chin, and even a little bit in her hair.

To my surprise, the guy fucking her ass still hadn't cum, and she started bucking her whole body against him while she fingered herself. The girls started to lead another guy to her pussy, but Cindy waved her hand and said she couldn't take any more. At this point, four of the girls were working on a guy, and they each led them around Cindy. Some of them used their hands, and some their mouths to get the guys ready to cum. As they came, the girls all aimed it so that it splattered all over Cindy's breasts, pussy, face and stomach. Cindy was still bucking hard against the guy in her ass, and fingering herself with one hand. She took the other hand and started rubbing the cum into her chest. Finally, the guy came in her ass, and she rolled off of him and laid next to him fingering herself until she collapsed into one final, huge, orgasm. Everyone cheered. At this point, she had had 8 guys inside of her, and another four had come on her, but there were still 13 guys left that were about to burst with excitement... A few of them started complaining that they had been left out.




Hiring Cindy Ch. 10



So, I told the girls that it was time to take off their panties. Another cheer as they pulled them down, leaving all five of them completely naked except for their high heels. Cindy was still laying on the floor trying to catch her breath and rubbing her cum covered body. I told the remaining guys that these girls were there to ensure that no one would leave this party unsatisfied. The girls each grabbed and quickly stripped one of the guys. Some of them started sucking their cocks, but Megan and the brunette each wanted to be fucked. Megan got on her hands and knees and pulled the guy's cock into her pussy from behind, and the brunette laid on top of her guy and rode his dick. I grabbed the redhead before she got a guy for herself and pulled he over to me. I told her that she was going to be mine for the rest of the night, and she smiled and started kissing me while I molested her entire naked body.

I took her over to one of my couches and we took off my clothes. I pushed her down and she took me into her mouth. It was the first attention my cock had gotten all night, and I had been so excited by everything that had happened that I nearly came right away, but I managed to hang on. After a minute I pulled her back up, turned her around, bent her over the arm of the couch and pushed my dick into her pussy. I fucked her like that for a while, and she was bucking back hard against me and building to an orgasm. Pretty soon she came loudly, but I kept it together and fucked her slowly until her spasms subsided.

Meanwhile, some of the girls finished off their guys and grabbed another. After a bit, the rest of the guys just stripped themselves and went over to the four girls. By the end, every girl was taking on two guys at a time. Fucking one, and sucking off the other. Cindy was just lying, covered in the cum of however many guys, in a daze, right in the midst of all these people. She was sort of just staring off into space and gently rubbing her cum drenched clit.

I pulled the redhead up standing again and led her over to Cindy. I guided her down on top of Cindy, the cum on Cindy's body now getting all over the redhead as well. Then I kneeled down behind her and grabbed the lube. I pushed a bunch of it into her ass and she squirmed at first away from my finger, and then back against it. I slid on top of her and pushed my cock into her ass slowly but firmly. She let out a long, low, moan as I went in. I started stroking in and out of her ass, and after a few strokes, she started to get more excited and started pushing back against me and kissing Cindy. After a few minutes, I came deep in her ass and got off of her. I told her to stay there attending to Cindy for now.

I looked around, some of the girls were still fucking guys. Some of the guys apparently had revived in time for an encore with a different girl. But, most of the guys were getting dressed again and starting to leave. After a bit longer, each of the girls was flopped out on the floor with a spent guy or two, just fondling each other and kissing. Cindy and the redhead were doing the same.

At that point, I thanked everyone for coming, and said that they could stay as long as they liked. Then I asked the redhead to help Cindy up to the bedroom and bathe her. As they were leaving, I told each of the girls that they should stay out there as long as they can and satisfy any guys that want more. They all agreed in sort of a daze.

I got back upstairs as the redhead and Cindy were coming out of the shower, and climbing into bed. We all just cuddled and fondled each other for a while, but after maybe 50 minutes, I told the redhead that I wanted her to go down on Cindy, but to be very gentle, as she had been very busy all night... She obliged, and I kissed Cindy and massaged her breasts as she gently caressed her pussy with her tongue. I didn't think she could cum again, but she seemed to enjoy the attention the redhead was giving her, and squirmed around and moaned softly.

After a while, I had gotten quite hard again, and the redhead had taken my cock into her hand and was stroking it. After a long time like that, Cindy thanked the redhead and gently pushed her mouth away. The redhead moved over and took me into her mouth instead. A couple of minutes later I realized that Cindy had fallen asleep... The poor girl was exhausted. I was getting near orgasm, but held off and then pulled the redhead off of my dick. I rolled over on to my stomach and pulled her hand beneath me so that she could massage my dick underneath me. Then, I nudged her mouth over to my ass and she obediently pushed her tongue into my ass. It felt great, and she stroked my cock as she pushed her tongue in and out. After a while, I stopped her. I pulled her up next to me on her stomach and slid on top of her. I guided my dick easily into her pussy from behind and fucked her until we both came.

After that, we all fell asleep in a pile. It turned out that someone had brought a bunch of blankets and pillows out into the living room, and all four girls, and 8 of the guys had slept there. Throughout the night, whenever a guy would wake up and realize that he was hard again, one of the girls would suck him off or let him fuck her. By morning, the girls were completely worn out.

I fucked the redhead again in the morning, but Cindy slept through it. After breakfast, they girls started getting ready to leave. They all thanked me again and again, and said that they would never forget this. A couple of them asked if I might do something like this again, and to let them know if I did.

After that, the remainder of the month was much less racy... Cindy and I both seemed kind of sad that our arrangement was about to end. We spent much more time holding each other and whatnot.

Finally, the last day came, and I paid the money into her account. She moved out, and back to Boston, but two weeks later I got a call from her. She wanted to come back. She wanted to be my girlfriend! I told her about my concerns that normal relationships get dull and whatnot, and she made me an offer. She said that as long as we were together she would play my slave for one weekend a month, and a full week once every three months. She didn't want to lose that edge any more than I did!