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Helping the Babysitter Become a Model
By stuffin
Chapter 13

Bob spent the rest of Sunday evening fucking Brenda and Kristin. When he needed time to recover he would have the girls play with each other. It usually didn’t take very long for him to get hard again watching them together. Early in the evening he took a few minutes to leave the girls alone so he could make some phone calls and make sure that the cameras were still recording.

Bob had recently installed high definition digital video camera’s throughout his house that recorded to his servers in his office. He had to find someone else to install everything since he couldn’t rely on Jim any longer, but it worked out well. He got everything at a steep discount in return for letting his contact participate in some of Kristin’s training sessions. Everything was still running and he had gotten some great footage. He didn’t think he would need to use any of it to keep Brenda in line with the way she was acting. It was hard to believe that the slut in the other room was the same woman that he had met at the restaurant earlier that day.

When he went back to the bedroom, Brenda was on her knees with her face on the bed and her ass in the air. She was begging Kristin to spank her as she was shoving a dildo in and out of her cunt. Kristin had found one his belts and had her arm back ready to bring it down on the other woman’s ass.

“Wait, don’t spank her yet.” Bob said to Kristin. He kneeled down next to Brenda and looked in her eyes. “Why do you want her to spank you?” he asked.

“Because I need it. I need to be spanked so I can cum.” Bob hadn’t realized that she had already picked up on the trigger that had been programmed into her subconscious. Over the evening he had already spanked her multiple times on her ass and tits, pushing her over the edge every time but he didn’t think that she had already associated the two with each other.

“And why should I let her spank you? Only naughty girls need spankings.” He was going to use this opportunity to reinforce Brenda’s role in her new life.

“I have been naughty, I swear. I need to be spanked!”

“I don’t believe you. Tell me how you have been a naughty girl.” He looked over at Kristin and she had a look of extreme lust on her face, enjoying watching the older woman degrading herself on his bed.

“I have been fucking my babysitter, isn’t that enough?” She looked in Bob’s eyes and could see that he wanted more. “Okay, I begged strangers to fuck me in the bar today. I wanted each of them to fuck me over and over. I loved the way I felt when I had their cocks in my pussy. Please, I’m naughty, I need to be spanked.”

“Tell me that you are a dirty slut and that you need to be fucked. And then I want you to take the dildo out of your cunt and I want you to fuck your ass with it.” She pulled the dildo out and went to put it in her ass but he wanted her in a different position. Bob helped reposition her on her back with her legs in the air and her ass hanging over the side of the bed. She tried to reach over her pussy to put the dildo in her ass, but Bob moved her hand around to the side, leaving her pussy unprotected.

“I’m a dirty slut and I need to be fucked. I need to have your cum inside of me. Whatever you want, I’ll do it, I swear”. The dildo that Brenda had been using on her pussy was 10 inches long with ridges twirling around the shaft. It was covered with her juices so lubrication wasn’t going to be an issue. Bob saw her grit her teeth as she slowly started pushing the head into her ass. He could tell it hurt, but she was still pushing it in without complaint. Once she got the head in she stopped, taking deep breaths.

“Kristin, give Mrs. Wilson something to take her mind off the dildo that she is putting in her ass. Go ahead and sit on her face and let her eat your pussy. Like you are going to sixty-nine with her but I want you to sit up and watch the show she is putting on.” Bob watched as Kristin eagerly climbed up on the bed and straddled the other woman’s face. As she ground her pussy into the mouth between her legs she reached down and started pinching and pulling on Brenda’s nipples without direction. Brenda moaned loudly into Kristin’s cunt and started pushing the dildo further into her own ass.

“I want the entire thing in your ass before I will believe that you have been naughty enough to deserve a spanking.” Brenda had about 3 inches of the dildo left and was slowing down, starting to whimper into Kristin’s cunt when Kristin reached down and started rubbing her clit. She had one finger on each side of her clit, rubbing up and down. With the added stimulation Brenda was able to push the rest of the dildo up her ass. “Good, now start fucking yourself with it. You can start slowly if you need to, but before you get your spanking you need to be able to push that entire dildo up your ass in one thrust.”

Brenda whimpered again but didn’t complain. Bob was pleased to see that even as she was whimpering she never stopped eating Kristin’s pussy. She started slowly pulling the dildo out and then pushing it back in, only about an inch at a time. Bob decided that she needed a little more encouragement and reached over and guided Kristin’s head into Brenda’s crotch. Kristin started sucking on Brenda’s clit as soon as she had her lips wrapped around it. Brenda began to fuck herself deeper with the dildo, pulling about six inches out before pushing it all the way back in. She was breathing harder, no longer whimpering as she fucked the dildo in and out of her ass, pulling a little more out with every stroke. It didn’t take her long and she was fucking her ass with the entire length of the dildo, pulling it out so far that only the head was left inside.

Bob reached down and pulled Kristin’s head from Brenda’s cunt. He brought his hand down hard on her cunt, aiming for her engorged clit. It was very swollen and sticking out from the attention that Kristin had been giving it. Brenda shoved the dildo all the way up her ass and moaned into Kristin’s cunt. Her entire body stiffened as she had another intense orgasm, causing her to almost throw Kristin off of her body.

When Brenda finally recovered Kristin looked at Bob and asked “Can I slap her pussy again? I don’t think she has been punished enough for being a dirty little slut. Did you see the way she was eating my pussy while she was shoving that dildo up her ass? Only dirty sluts would do something like that.”

“You are right, she is acting like a dirty slut but she needs a minute to recover from her last orgasm.” Bob reached down and pulled the dildo out of Brenda’s ass, causing her body to shudder with pleasure. He held the rubber cock up to Kristin’s mouth and watched as she obediently opened her mouth to accept it. Kristin took the entire thing into her mouth letting the rubber cock push into her throat. She pulled the dildo out of her mouth, licking the entire length with her tongue, staring into Bob’s eyes the whole time and giving him a big smile.


The rest of that night had Brenda tied to a chair in the bedroom with a vibrator secured to her cunt. The vibrator was set to vary it’s intensity, keeping her constantly stimulated by varying levels the entire night. She had the hood back on playing the white noise, programming her to be the slut that Bob now knew she really was. And the built in blindfold prevented her from seeing when someone would provide the pain that she needed to cum. She had a ball gag in her mouth, preventing her from keeping him up with her constant begging to cum. Brenda had surprised him. It only took a little chemical persuasion to get her to drop her inhibitions and she was acting like a wanton whore, ready to let anyone use her body for their pleasure and she genuinely seemed to enjoy it. And she had accepted the subliminal messages faster than he hoped, showing him that what was being suggested to her subconscious wasn’t very far from what she truly wanted. She now required some sort of pain to push her over the edge and achieve orgasm.

After Kristin helped Bob secure Brenda to the chair Bob had her ride his cock one last time before going to sleep. The orgasm she had as he came inside her was just as strong as the first one she had that day. As she climbed off of his cock, Bob handed her a bullet vibrator to put in her pussy for the rest of the night. It had a timer that would make it turn on every hour, waking her up. Bob told Kristin that when the bullet woke her up she was to get out of bed and give Mrs. Wilson the orgasm that she would be begging for. She could either whip her tits with the crop sitting next to the chair, spank her pussy, or twist her nipples hard enough to make her cum.

“Thank you sir, I would love to help you train your new slave.”

Bob was proud of his teenage slave. She was going to continue making him a lot of money. And now that he had another slave to use, he would be able to take jobs that required more than one girl. He smiled as he turned over to go to sleep.


Bob woke up the next morning to see Kristin standing in front of Brenda, twisting and pulling on the bound woman’s nipples. Kristin was pinching Brenda’s nipples hard to give her what she needed to cum. Brenda was bucking in the seat, having another intense orgasm. Brenda’s chest was slick with her own drool from the gag and the seat cushion was soaked with the cum that had been constantly dripping out of her pussy through out the night. When Brenda’s orgasm subsided, Kristin released her nipples and then bent down to suck each one into her mouth, soothing the pain that she had caused away. Bob noticed that as she sucked on Brenda’s nipples her hand went to her pussy and she started fucking herself with three fingers.

“Now, now. Don’t get started again or you are going to be late for school.” Bob walked over and pulled Kristin up to give her a deep kiss. She began rubbing her body against his and her hand that wasn’t buried in her cunt reached out for his cock.

“Please, sir. Please fuck me. I can’t stand a whole day at school feeling like this. I need to cum, please! She got to have so many orgasms last night and I haven’t had any,” she whined. Her hand was stroking his cock and he was starting to stiffen. How could he deny her when she asked so nicely. He reached over and took the ball gag from Brenda’s mouth and turned Kristin around and made her lean over so the two women could kiss as Bob fucked the teen. Brenda returned Kristin’s kisses passionately as Bob fucked her pussy. Watching them kiss pushed him over the edge and he filled Kristin’s cunt, causing her to cum with him. She immediately turned around and dropped to her knees so she could suck his cock clean, murmuring thank you’s the entire time.

Bob let her clean him up before sending her to the bathroom to get ready for school. He had anticipated eventually having her stay with him over a school night and had purchased a small wardrobe for her to wear so she didn’t have to wear the same clothes as the day before. The clothes he had bought for her were sexier than what she would have worn before becoming his slave, but not enough to draw unwarranted attention to herself.

As Kristin was showering, Bob turned his attention to his new slave. Her body was wonderful. She had long lean legs and a taut stomach. He guessed that she must work out every day to keep herself in this kind of shape. He would have to make sure that she continued working out so she wouldn’t lose her shape, although it would probably be a different workout than she was used to.

Bob untied Brenda from the chair and removed the vibrator. She slumped in the chair exhausted from no sleep and an orgasm every hour. Her pussy was swollen and red from the constant stimulation and Bob could tell that she was going to be sore. When Bob pulled the hood from her head, Brenda looked him in the eye and gave him a weak smile as she whispered thank you before falling asleep.

Bob carried her to the guest bedroom and let her get some rest while she could. She was going to have a long day of training and would need all the energy she could get. Bob had upgraded the guest room just in case he needed to let someone rest without worrying about them wandering around the house or trying to escape. The windows had shatterproof glass and had an electronic lock that wouldn’t open without a code. The walls and windows were sound proofed, just like the rest of his house so even if someone were on his property there was no worry they would hear anything. He had been fortunate to find the property that he owned, fifty acres right outside the city with his closest neighbor over half a mile away. There was a phone in the room but it wouldn’t dial out and if anyone tried it would sent a notification to his cell phone. The door was sturdy and locked from the outside. There also wasn’t anything in the room that someone could use to hurt themselves if they were that desperate. Bob didn’t think that was a risk for Brenda, but he didn’t want to have to worry.

Bob left a note for Brenda on the table which read “Good morning. I hope that you enjoyed your first night as my slave. If you didn’t, that’s ok, but your time with me will be easier on you if you learn to enjoy yourself. I know you must be hungry. There are energy bars in the cabinet under the TV. I think they are delicious so please, help yourself. You must also be pretty sore. There is a cream on the counter in the bathroom that you can use to soothe your sore pussy and asshole. Please use the gloves that are next to the container and be careful not to get it anywhere else. It works best if you rub the cream inside each of your holes and not just the outside. I want you to rest while you can, you are going to have a long day. But if you can’t get back to sleep, I want you to watch the video that is queued up for you on the TV. Just turn it on and it will start playing. If you feel the need, the bedside table drawers have any toys you might desire. I will be back in a little while to continue your training. Love, Bob”

The energy bars that he provided were a special mixture that he made and included a small amount of the drug that removed inhibitions and increased sexual desires. With Brenda’s performance the night before he didn’t really think the drugs were necessary but they would also bring her back in line if she was starting to have second thoughts. The cream he had mentioned was something else he had gotten from his government contact. It had multiple properties and would soothe her pain as he had said. But it would also remove any hair and prevent it from growing back, basically killing the hair follicles. Brenda would have a hairless pussy for the rest of her life. It also caused any orifice that it was put in to better retain its size and shape, so Brenda’s pussy and asshole would remain as tight as they currently were and never loosen. If Brenda didn’t use the cream on herself while he was gone, he would make sure it was applied before her training session.

When he had her settled in the room sleeping peacefully, he went to his office to check the recordings from the last day and to quickly edit a recording for Brenda to watch when she woke up. When the video edit was finished he set it to stream to the TV in the guest room on a continuous loop, starting when the TV turned on. If Brenda didn’t turn the TV on herself, it would come on automatically at noon. Finished in his office, he came out to make breakfast. He was just finished making bacon and eggs when Kristin came out. She was wearing a skinny black skirt that came down just over her knees with black thigh high stockings and a tight white button down shirt. The shirt was a little small and her nipples were poking out even through her thin bra. She looked incredible. Bob wanted to bend her over the kitchen table and fuck her right there, but he had too many things to do.

“Here, eat this and I’ll make some more for myself before I take you to school. I want you to know that I am very pleased with your performance last night and this morning.”

Kristin smiled a genuine smile as she sat down at the table as Bob sat the plate in front of her. It didn’t worry her at all that his praise made her proud. Her resistance to her new life was slowly wearing away, she was truly becoming the slut that Bob was molding her into. As she looked at the food in front of her, she realized how hungry she was. She hadn’t eaten anything but cum since lunch the day before. As she thought about swallowing Bob’s and Mrs. Wilson’s cum while she ate her breakfast, her pussy began to soak her panties and leave a wet spot on the chair.


Bob drove Kristin to school in his car, not wanting to draw attention by driving the van to a high school, he didn’t want to look like a rapist after all. As she was about to get out of the car Bob reminded her “Don’t forget to come up with an excuse to tell your parents for the next couple of nights.”

“Can’t I just tell them that I am babysitting for the Wilsons? I’ve had to spend the night at their house before and you could even have Mrs. Wilson call them and make sure it’s ok.”

Bob couldn’t believe that he hadn’t thought of that before. It was a perfect cover for getting Kristin out of her house on any night of the week. Bob smiled at Kristin and told her that he would have to give her a special treat for having such a good idea. The smile that she gave him was sweet and sexy at the same time and seemed genuinely sincere.

As she walked up the sidewalk to the school, Bob sat in his car watching his little teenage fuck slave walk away. She was stopped by a group of cheerleaders. Bob could tell Kristin and the cheerleaders weren’t friends but couldn’t hear what they were saying. The group was lead by a strawberry blonde who was much taller than Kristin. Kristin pushed her way through the girls and walked into the school, but Bob could tell from the way she walked that she wasn’t happy about what the girls had been saying to her.


Bob drove by the Wilson’s house on his way home. He saw that Jim’s car wasn’t in the driveway so he parked and walked up to the front door with his bag of tools in his hand. He used Brenda’s keys to let himself in. He had been in the Wilson’s house plenty of times, but always when Jim was there. He wanted to get back to his house to continue Brenda’s training, but he had things he needed to do. Work before pleasure, right?

He knew that Jim was the computer geek, but Bob had clients that were willing to work in trade and some of them worked for various three letter agencies. He went into Jim’s office and crawled under the desk. He took out a small box, about the size of pack of cigarettes and fastened it to the bottom of the desk behind the drawers so it wouldn’t be seen by someone casually looking under the desk. His government contact called it the “Universal Backdoor”. The device had already been configured to capture any incoming or outgoing communications, computer and phone, and use any available internet service to forward the information through multiple servers around the world before ending up on Bob’s servers at home. It would even capture cell phone calls that were made within range of the device. The range was pretty good and would cover most of the house including the master bedroom. One other feature of the device was that it provided a way for Bob to hack into Jim’s computer with no effort whatsoever.

Once the device was installed under Jim’s desk he moved on to the master bedroom. He looked through the dressers and the closets looking for anything of interest. He found a box of tissues and the packet of pictures that he had left with Jim before hidden under some clothes in Jim’s dresser. So Jim didn’t feel so guilty about fucking his babysitter that he didn’t masterbate to the pictures. That was good to know.

As he was going through Brenda’s closet he found where she kept her sexiest underwear. For someone who was a closet slut her underwear was a disappointment. He would have to take her shopping. He found her diary in the bottom drawer of her bedside table, next to a small dildo. He took the diary but left the vibrator, she would be using much larger dildos from now on.

As he left the Wilson’s house he smiled to himself. He really had to thank Jim for the situation he was in now. Without him Bob wouldn’t have been able to make Kristin his slave. And now he had Jim’s wife to play with as well. And without her being worried about Jim, she never would have agreed to meet with Bob in secret.


Bob had to make a few more stops on his way home but he wasn’t worried about Brenda. He was sure that she was either asleep or keeping herself occupied in some way. Bob would have received a text notification on his cellphone if any of the doors or windows had been opened while his security system was turned on or if she had tried to make a phone call. Bob headed back to his house, feeling that he had a productive morning, especially the stop at the Wilson’s. He had skimmed through Brenda’s diary while sitting at a few stop lights and had found a few juicy bits. He would have to take some time this afternoon to go through it more thoroughly. He made a few calls on the way home wanting to make sure that he had everything set up for the next phase of Brenda’s training. Big Rick was available and was looking forward to getting another crack at the sexy housewife’s ass. “Don’t worry, she’ll be begging you to fuck her ass before the end of the day.”

When Bob got home he didn’t immediately go to the guest room. He wanted to see how Brenda had spent her time alone. He went into his office and pulled up the video feed from the guest room and saw that Brenda had pulled a chair up in front of the tv and she was currently working two dildos in and out of her pussy and ass as she watched the video that Bob had queued up for her. She was wearing one of the catholic school girl uniforms from the closet. She had the skirt pulled up around her waist as she worked the dildos in and out of her holes and the look on her face was pure ecstasy. Bob watched her fuck herself for a few minutes before rewinding the recording to see how she had spent her time alone.


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