While Lexi was being milked by the machine attached to her, Susan was sitting in a room with Toots and Gary. They were discussing how the day (and night's) activities were going to go. Gary knew that Alexa's first fuck was going to be done by Toots. He didn't mind because he had his own plans for her and a plain old vanilla fuck wasn't high on his list. He had really enjoyed watching the films Toots and Susan had made showing her first few humiliating episodes with customers. He especially liked watching her face as the one man had used her little tits like they were a pussy. Her look of mortification while he was sliding his cock in and out of them was a real turn on. Gary knew that was just one of the many things he was going to do to her. The fun part was that she would know that he was a friend of the family but she would have no idea of his identity. He wanted to use her and to see her used but he wasn't stupid. She would never see his face until Toots was ready to sell her. Once that happened she would never be seen again and knowing that she would finally know who did this to her would be the icing on the cake.
He was intrigued by Susan's fascination with the girl. Having a relationship with her many years ago did give him some insight into her mind, but he had never expected it to go so far as Susan becoming a madam in a whorehouse. They had sex in a lot of situations that were not what anyone would call normal but they weren't that far out there. I all started innocently enough with some phone sex. He remembered how Susan's voice became very excited when he told her of his fantasy about her being a topless dancer or a hooker in some sleazy bar. She told him to tell her what she would have to do there. He had described it and in subsequent calls he had become more and more graphic about what lewd things she would have to do to her customers. He also knew Toots and the topless bar he owned on the edge of town. The girls weren't the fancy pole dancers of today. They looked more or less like average women trying to make a living off their looks. He also knew that Toots owned the Gentle Touch massage parlor next door. It was an old run down motel that had seen better days. Toots used it to pimp some of his dancers out. Not all of them were prostitutes but he had enough to satisfy his customers.
Gary knew of this because he would stop at the bar occasionally and enjoy the dancers and had used the services of the girls next door, too. One night at the Ranch House he was talking to Toots and told him about the phone fantasies Susan and he had shared. Toots matter-of-factly told him that if he ever wanted to make it real to send Susan out to talk to him and he could arrange it so the fantasy became a reality.
The next time he and Susan had phone sex he decided to spice up the conversation by telling her what Toots had said. To his surprise she didn't get angry and actually became even more turned on, so he went into more and more detail about what she would be doing at the massage parlor. It turned out to be the best phone sex they had ever had. A couple of weeks later Susan had asked him if Toots was serious about the whole thing. He was surprised but eagerly told her he would check with Toots and see what he could arrange. The idea of Susan being a paid whore turned him on immensely. It was the way his brain was wired. Normal sex was boring and that is what he enjoyed about Susan so much. She was wired in much the same way.
Well, long story short I stopped at the Ranch House and told Toots that Susan wanted to talk to him. For Toots it wasn't a big deal. She was just another whore as far as he was concerned. Gary showed him some photos he had taken of Susan posing in the nude and in various stages of modeling some cheap lingerie. Toots looked at them and said he could definitely put her to work. He would do a fifty-fifty split with her if she worked out. He also said he needed to "interview" her to see if she could actually fuck and suck a stranger for money.
"Talk's cheap. I need to know if she can fuck and suck a stranger for money. She can start with me. If she can suck me off when I tell her to, then I can use her. If not, well she can get lost. Oh, and one other thing. Don't tell her about me using her. I want it to be spontaneous. That's the only way I will know if she has what it takes to be a paid whore." I had assured him that I would not say a word about the arrangement.
The next time Susan and I were in bed I told her that Toots wanted to meet her if she was serious about doing some hooking on the side. After some initial hesitation she said she wanted to do it. Before I left, I gave her the Ranch house's phone number and told her to ask for Toots. She just nodded. I was totally turned on by this whole thing and I wanted to know if she would actually go through with it. I drove through the Ranch House parking lot every night for the next week or so and I was finally rewarded when I saw her car parked in the rear of the building. I was stunned and turned on at the same time. She was actually doing it! She was in a tittie bar arranging to be a prostitute for a fat biker. I went home and jacked off thinking about her sucking off Toots.
Well she never did tell me the details of her arrangement. In fact she didn't talk about it at all. The more I pressed her on the issue the more she clammed up. I wanted to know all about it and she wasn't telling. It was the beginning of the end of our relationship. We finally split up but I did still stop at the Ranch House occasionally. One night Toots took me into his office and told me what was going on with Susan. He said she had become his best whore and she was really popular with the customers. He could tell I was still very interested in the whole thing. Then he did something that I hadn't expected. He told me that he had cameras set up in some of the rooms at the massage parlor and had taped a lot of sessions his girls did. They had no idea of course, but he kept them as leverage in case they got cold feet and wanted to turn him in. He stood up and went to a locked file cabinet and opened it. He pulled out a VHS tape and showed it to me. It was titled: Susan Interview session.
"Do you wanna see it?"
I just nodded my head. He chuckled and went to the TV in the corner and popped the tape in the VCR.
It showed the inside of the office, the same one I was sitting in. Toots was behind his desk when someone knocked on the door. One of Toots' dancers peeked inside and said that some blonde was there to see him. He smiled and said "Send her in." The next thing I saw was Susan. She was dressed in a wraparound dress and wore her customary high heels.
"Nice to meet you Susan. Gary has told me a lot about you. He says you want to go to work for me."
Susan said yes. I could hear the nervousness in her voice, but there she was sitting in the office of a whoremaster and not knowing she would soon be "interviewing" him in detail. Otherwise Toots wouldn't have bothered to show me the tape. I was getting hard just thinking about it.
"This is where it starts to get interesting," Toots said with a big smile.
"Here's the deal Susan. You will start here as a waitress and I will have you do some quickie blow jobs in the parking lot the first week or two. I will pay you waitress wages but you can keep half of what I collect for your services. That will be about $20 per customer. If that works out you can go to work at the Gentle Touch and you will make anywhere from four to eight hundred dollars a week. That's If you are good and the customers like you. How does that sound?"
Susan sat for a moment and said it sounded good to her, but she asked why she had to wait tables.
"Because I said so. You need to be around the lifestyle so you get used to it. You need to know the girls and watch how they hustle drinks and lap dances. It will serve you well in the future. Oh, and one more thing. You need to show me some of your skills. Gary said you were a good cocksucker. I need you to prove it. Take your dress off and get over here.
I could see the shock on her face, but she slowly stood up and undid the tie around her dress and undid the buttons at her waist. She slipped out of it and stood there in nothing but her bra, pantyhose and heels. Remember this was years ago and Susan was still a fine looking woman. I could see Toots' eyes light up with lust or greed, probably both.
"Nice! Take the bra off. I want to see what you have." She did as she was told and slipped the straps off her shoulders, spun the bra around and unhooked the clasps. She stood there with her tits hanging out while Toots looked her up and down.
