The Cost of a Debt Ch. 02

Alex returned home with all of the packages from the stores she was sent to. She did have mixed feelings about paying for everything that she was sent to get. Basically, everything that she had gotten was for the Head Master to get off on. This is a person that she has still not yet met, but is dictating her life. The Head Master had forced her to buy things that she would have never bought in a million years. She just never had the nerve to wear revealing blouses or short skirts. Now, she was being blackmailed to do the exact thing that she didn't have the nerve to do before.

Alex walked up straight to her bedroom and opened all of the bags from her errands run. She took out the summer dresses, choker, and her new lingerie selection. She started to blush and getting nervous by just looking at what laid on her bed. Alex sat down, and then her cell phone rang. She didn't have to pick it up, yet knew who it was.

"Hello Alex," the Head Master said. "Did you enjoy your little shopping trip?"

"Yes," Alex said.

"Did you get everything like you were told to," he asked.

"Yes, I did," Alex said.

"Now, tomorrow is a school day," the Head Master said. "From now on, you are going to wait until my phone call to find out what you are going to be allowed to wear. Do you understand?"

"Yes," she said.

"Very good," he said. "Now have a good night." He then hung up.

She put everything that she just bought away and went down to prepare dinner for herself and David. The rest of the evening was uneventful. Alex went to bed thinking about what the Head Master had in store for her. While Alex was asleep, all she could think and dream about were the photos of her daughter Annabel. But instead of picturing Annabel in the photos, she was imagining herself.

Alex dreamt that 3 male college students who had fantasies of having sex with an older woman were overtaking her. The guys had Alex first on her knees while she was giving them each a long and slow blow job. Then she was picked up and carried to a bed where she was laid on her back. Once there, one guy opened up her legs and began to lick and suck her pussy. The other two stood beside her while she reached out and stroked the cock of both guys. The guy between her legs began to move up her body beginning by kissing her stomach and slowly making his way up to her breast area. He then got his cock and put it deep inside of Alex. At that point, she tried to get up so that she could begin to suck one of their cocks. She took it nice and slow. Then before she knew it...her alarm went off.

Alex woke up by herself. There were no young college students to be found.

David was awake and getting ready to go to school. Alex had gotten into the shower and could only imagine what the Head Master had wanted her to wear. She got out of the shower expecting to hear from the Head Master shortly. Alex got into her robe, but didn't want to do anything else until the Head Master called. As David was ready to leave, her cell phone rang.

"Hello Alex," the Head Master said. "Were you anticipating my phone call?"

"Yes," Alex said. "What would you like me to wear today?"

"You may wear a blouse and long skirt that you normally wear to school," he said. "Underneath, you will wear a sheer bra and thong that you bought yesterday."

"Okay," Alex said. "Is there anything else?"

"Yes," he said. "I want you to go get a doggie collar and wear it all day long."

With that, he hung up. Alex sat there.

"A doggie collar," she thought. "This will be humiliating to wear a collar all day. All of the students will be staring at her."

She got a brilliant idea. The Head Master only asked her to wear a blouse and long skirt. Alex decided that she was going to wear a white blouse, long beige skirt, and a black turtleneck shirt. Underneath the turtleneck, she would wear the collar. Alex rushed to get this all on so that she could get to school on time.

On the drive to school, Alex was trying to conceal the collar as much as possible. The turtleneck hid the collar fairly well. Once Alex got to school, she took one final look at the turtleneck. Afterwards, she got out of her car and walked into the school with 2 minutes to spare.

The school day went by with little to no excitement. Once she finished teaching her last class, her cell phone rang.

"Hello Alex," the Head Master said. "I see that you didn't quite follow my instructions."

"Yes, I did," Alex said.

"I see that I am going to have to be much more specific and direct with you," he said.

"What do you mean," Alex asked.

"I mean, the idea behind you wearing the collar is to show your obedience towards me," he said. "I will give you a second chance. Go home and take off your turtleneck and wait for more instructions."

He hung up. Alex knew that she was disobeying the Head Master by deciding to wear the turtleneck, but she didn't want to attract any more attention with the dog collar on her neck. She gathered her purse and school bags and walked out of her classroom and toward her car. As she was driving home, she could not help but wonder what her further instructions will be.

She pulled up into her driveway and parked her car. Alex gathered her bags and walked into her house. No one was home. After putting her things down, she decided to go to the kitchen for a glass of wine. She needed it.

A few minutes later, her cell phone rang again. She picked it up immediately.

"Alex," the Head Master said, "I have sent the car to pick you up at your house. The driver will be there in 5 minutes. You will wear what you wore to work...except for the turtle neck." He then hung up.

Alex was speechless. She has never been given commands like this ever before. In fear of what the Head Master would do if she disobeyed him, she immediately finished the glass of wine and walked to her bedroom, took off her blouse and then took off the turtleneck. She then re-buttoned her blouse and then became extremely nervous. Alex walked out the front door of her house to wait for the limousine to pick her up. Within a few minutes, the limousine was in front of her house. The driver put the car into park and got out of the car. He circled around the car and opened the back door for Alex to get into the car. She stepped in and took a seat. To her surprise, a middle aged man sat across from her. From the sound of his voice, she identified him as the Head Master. The driver got back into the car and drove off.

"Why hello Alex," the Head Master said. "I am glad that you were able to make it today and join me."

"Who are you, and why am I here," Alex asked.

"Well, to answer your questions, I am the Head Master and because I can," he said.

"Blackmail is illegal," Alex said.

"We aren't going to have to go over this all over again, do we," the Head Master asked. "I told you, that the choice was up to you. You are free to go to the police, but I will be forced to release all of the photos and documents that I have on you. Your family's image will be ruined and you will have a lot of questions to answer."

"Why me," she asked.

"Because I can," the Head Master said. "I see that you have taken off the turtleneck, like I had asked."

"Yes, I have," Alex said.

"I do have to say that you make your conservative wardrobe appear extremely sexy," the Head Master said.

"Thank you," she said.

"But I am not a fan of conservative clothing. I want you to change into the dress that is in the bag next to you," the Head Master said referring to the clothing bag to her left on the seat.

Without hesitation, she opened the bag to see what was inside. She pulled out a sleeveless summer dress. The dress was much shorter than what she would normally wear. It also had a low cut neckline that was sure to expose her cleavage. She sat there and stared at the dress.

"Do you like your gift," the Head Master asked.

In fearing how he react if she said anything negative, Alex replied with a simple "yes."

"Well good," the Head Master said. "Now I want you to change into it."

"Now," Alex asked. "Yes," he replied.

"But there is no room," she said.

"I am sure you can make due," the Head Master said.

Alex knew that it was not worth fighting. She un-buttoned her blouse and took it off. She then slipped off her heels and then took off her skirt.

"Very nice," the Head Master said.

Alex was embarrassed as she tried to cover herself in her bra and thong. She then picked up the dress and slid it over her head and pulled it down. As expected, the low cut neck line exposed a great deal of cleavage. Alex pulled down the dress only to find that it goes down to the middle of her thighs.

"You look very nice," the Head Master said. "I can see why you are so popular."

"Popular," Alex asked.

"Yes, let me explain," the Head Master said leaning back into his seat. "I guess you can say that I am the founder of a social club. The club has a number of influential members who come together to escape the stresses of their jobs and responsibilities. We try to organize parties and arrangements to do just that. In fact, many of our members join simply do things that they could never imagine doing in their normal lives."

"I don't understand," Alex said confused.

"Let me just say this," the Head Master said, "our members have a great deal of input in the selection process of our support network. You by far received the most requests we have ever had."

"Requests for what," Alex asked.

"To be a part of their fantasies," the Head Master said.

"Fantasies," Alex asked. "What am I supposed to do in their fantasies?"

"Anything that our members want," he said.

"Wait, I am not going to have sex with them. I am not a prostitute," Alex said.

"I never used the word prostitution and you will not be a prostitute," the Head Master said. "I would just say that you are a fantasy maker."

"What kind of social club is this," Alex asked.

"It is one that can make you if you, if you are nice, " he said, "or it can break you like no other. We have very influential members."

Alex stayed quiet. She didn't know what to make of this. The Head Master had known of things about her family that she didn't know.

"Now I want you to get on your knees in front of me," he said.

Alex did just that. She got on her knees before him. The Head Master then reached back and got a leash and clipped it to her collar. He pulled Alex close to him and then bent over to whisper in her ear.

"How does it feel to lose control of your mind and body," he asked.

Alex got goosebumps all up her arms and back. She knew that she had no options.

"Now I want you to show me your appreciation and suck my cock," he said.

Alex, without any further instruction, reached up and unbuckled his pants and reached in to pull out his semi limp cock. She started to lick his cock, which caused him to go rock hard. She then took his cock into her mouth. Alex had never sucked another cock outside of her husband Mike's. She could tell that he was enjoying the blow job as she could see his breathing becoming shorter and faster. As his body began to tense up for what Alex was preparing for, the phone in the limousine rang. The Head Master stopped Alex and picked up the phone. The conversation was short and he hung up the phone. He then instructed Alex to sit back up on the seat.

As Alex struggled to get back up, the Head Master was getting his cock back into his pants. The car then pulled off to the side of the road.

"Well, it looks like our first member is ready and is anxiously waiting for you," he said. Before Alex could respond, the driver opened the back door. The Head Master got out and held his hand out to help Alex out of the car. Once they were both out of the car, the Head Master reached down and grabbed Alex's leash. He lead her up the stairs to a large house.

Alex looked around and didn't see anyone outside. The sun was down, so Alex was somewhat relieved. The two of them then were on the door step of the house. The Head Master then rang the door bell, and within a few minutes someone answered the door. Once the door opened, Alex was horrified.

The person who answered the door was John Grigsby. He was a former student that Alex had taught. More importantly though, he was the star football player that Alex had given a failing grade to because she caught him cheating on an exam. Because he failed the class, John was suspended from the team and his hopes to playing in college and professionally had been dashed.

"Hello there, John," the Head Master said.

"I see that you have brought over a familiar face," John said with an evil smirk on his face looking at Alex.

"Yes, as you requested," the Head Master said.

"We will have a lot to catch up on," John said.

"Okay," the Head Master said. "John, she is yours for the evening. You do remember the rules."

"Yes, I know," John said. "HA, rules...you mean the lack there of, right?"

"Well, guidelines," the Head Master said. "Now, be nice and here you go."

The Head Master gave John the leash and the hand off was complete.

"We are going to have a fun evening," John said as he pulled Alex through the door. He closed the door and walked her into the living room.

The Head Master then turned around walked back to the limousine. Alex's stomach just began to turn. She was scared to find out what she had gotten herself into.

"Why, it's been quite some time since I have last seen you," John said. "I do have to say that the last time that I had seen you, it was under different circumstances."

Alex was unsure what to say. She was at her former student's disposal. If she said the wrong thing, there is no telling what the consequences would be. In fact the last time she had seen him was over five years ago and he was appealing to the school principal to let him play the last game of his senior season.

"I see that the cat's got your tongue," he said. "Well, I hope that won't be the case this evening."

"What are you going to have me do," Alex asked.

"Nothing really. All you have to do is look pretty," John said with a smirk. He sat down on the couch while Alex stood in front of him. He pulled her closer to him with the leash. She was about ready to sit on the couch next to John before he instructed her to remain standing. As Alex stood in front of him, he reached out with his hands to feel up her thighs.

"I can't tell you how long I have wanted to do this," John said. He slid his hands up to her ass and then noticed that she had a thong on. This disappointed John and he told her to take it off. She did as she was told to do. As she pulled them down her legs, the front of her thong was noticeably wet.

"I see this a turn on to you," John said as Alex gave it to him. He put it down on the coffee table and stood up getting closer to Alex. John began to again run his hands up and down her ass and at one point cupping her firm butt with his right hand. He would then run his hands up her body to her chest area. He felt the outline of her bra.

"I don't think you will be needing a bra either," John said. As Alex pulled the straps from the dress off her shoulders to take off her bra, she became extremely nervous and anxious. Here she was with a former student who was over 10 years younger than her.

She took off the bra and handed it to him. He then took it put it on the coffee table next to her thong. He then took Alex by the leash and lead her out to another door.

"Are you up for an outing on the town," John asked.

"Uh....yes," Alex said reluctantly.

"Great," he said. John then took Alex by the hand out to his car. He was polite enough to open and close the door for her.

"Where are we going," Alex asked.

"You are going to be my date for a dinner party," John said with a slight smirk.

Alex stayed silent. She began to get butterflies in her stomach. Here she was, in the car of a former student of hers who had failed her class. But at the same time, time had been extremely kind to John. Since he was a student in her class, he had definitely matured into a man. He had grown to over six feet tall, and had stayed in shape. As they drove down the freeway, Alex's mind had wandered off. She began to fantasize about making love to John. She began to think about running her fingers down his broad shoulders and over his chest. Then Alex imagined John picking her up and throwing her on his bed.

As the thought consumed her imagination, she was quickly brought back to reality. John was over fifteen years younger than her, not to mention that she was happily married to Mike. Cheating on Mike had never crossed her mind. But there she sat as John's date.

"What are people going to think," Alex asked.

"They are going to think what we tell them to think," John said.

"What may that be," Alex asked. "Leave that to me," John said. "But what difference does it make. You are mine for the evening remember?"

"Yes," Alex said submissively.

Within minutes, John pulled over to a fancy restaurant a few miles outside of the city. As they came to a stop, the valet for the restaurant came up to Alex's door and opened it for her. John then came around and put his arm around Alex. Alex was surprised.

"Tonight, you are going to go along with anything I do," John said. "Oh, and make sure your wedding ring stays on all night."

John then grabbed her hand, and the two of them walked into the restaurant. It was clear that the restaurant had been rented out for one giant party. Once inside, she began to scan the crowd for anyone that she knew. Lucky for Alex, she didn't see anyone familiar, but she did notice that the crowd was much younger in age than she was. Then she heard someone yell out John's name. The two of them stopped as John began to talk to a man walking across the room. The two shook hands and John introduced the man to Alex.

"Bobby, this is my date, Alex," John said as Bobby extended his hand.

"Pleasure to meet you," Alex said politely.

"Trust me, the pleasure is all mine," Bobby said. He then took a half step back and began to check out Alex.

Bobby and John then turned to each other had started a small talk conversation. Alex began to look around and many of the people walking in (particularly young men) were staring at Alex as she held on to John's hand. Some had mischievous smiles on their face. Alex felt somewhat uncomfortable as she never has worn a dress like this before. On the other hand, Alex has never gotten this much attention from other men before. She could only imagine what was going through their minds.

Before she knew it, John's conversation with Bobby ended and John continued to lead her though the restaurant. While walking through the restaurant, John greeted a handful of other men. He would introduce them to Alex, but due to the situation, everything was a daze. The two of them eventually made it to a table in the back. Once they sat down, Alex asked John a question that she had on her mind the entire evening.

"John, why me," Alex asked.

"Because you ruined my life," John said bluntly. "Let's see, I am in my senior year of high school and you failed me, forcing me off of the football team. You realize that I had scholarship offers from three different schools."

"But you cheated on your exam," Alex said. "Yeah, but you aren't the model citizen either," John replied. "Or should I say that your kids, aren't the model citizens either. You do have to remember that I played football with David. His gambling and drinking are no secret."

"Leave my kids out of this," Alex said.

"Uh, no," John said. "Isn't the reason why you are even in this mess is because of your son? I also know about Annabel. She has made quite a reputation for herself in college."

Alex didn't know what to say. She sat there in silence.