Hiring Cindy Ch. 05byWhoAmI99©
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.