Chapter 4: Day Four: Transactions

Mike’s parents had already left for their jobs right after breakfast. According to central control, all the teens had two hours of free time before reporting for math and science class. Mike enjoyed math and was really looking forward to this because one of the assistant instructors was Slave Eddie who had a Ph.D. in math theory with a strong background in physics. Mike requested some private tutoring from Eddie specifically on Quantum Theory which fascinated Mike. Central control checked Mike’s academic background and consulted with Slave Eddie and told him his request for a breakout lesson in math class was granted, much to his delight.

His sisters rolled their eyes at their nerd brother when he announced this at breakfast, but Mom and Dad seemed very pleased. Pam and Tammy dreaded math class and even though they were two grades ahead of him they always looked to Mike for homework help. They decided they wanted to spend their free time at the pool in the slave village.

The dress code for the pool was no clothes. They were not given swim suits and the slave outfits were not appropriate for swimming. In just three days the girls had lost their shyness about being naked in public and stripped off their outfits when they got to the pool. Everyone else there was naked so it was not intimidating to them. Besides, they got a chance to work on their ‘all over tan’ they had seen on the other slaves here. No more bikini tan lines.

Mike was thinking about joining them when the doorbell rang to the Clark bungalow. Mike opened the door to find Marcie and Carrie Brubaker. Mike was so surprised to see Marcie he stood frozen for way too long before he stammered “Marcie! Carrie! Please come in. Wha ... What’s up?”

Carrie gave Mike a bright smile “Thanks Mike!”

Marcie on the other hand seemed shy and reserved but was just as beautiful as ever. She had a hard time looking at Mike in the eyes and demurely kept looking at the floor. She was four years older than Mike but after what happened the second day on the island, when she was ordered to give him a blowjob, she was still embarrassed. “We came to ask you for a favor. I cleared this with Master Brian before coming here.”

“Sure, whatever you want, Marcie.”

“This is awkward considering what happened a couple of days ago.” Mike wasn’t sure if he should say anything in front of Carrie and he glanced in her direction. “Don’t worry, I told Carrie all about it.”

Carrie smiled brightly “Yeah, she told me all about your blowjob, Mike!” Mike’s face went five shades of red.

“Carrie! I can’t believe you. Sorry Mike, she can get pretty excited.”

Mike laughed. “While I guess that incident isn’t awkward for someone.” He turned to Marcie serious again. “I haven’t had a chance to properly apologize for what I did to you.”

“First of all, you weren’t responsible. I was ordered to do it.”

“Yeah, but they made you do it only because they knew I was following you around all the time because I thought you were so beautiful. And still do.”

“Mike, if it wasn’t me, then it would have been someone else. Its not like I haven’t done it before. Of course, I have to admit, all the boys I dated before were not nearly as nicely ... endowed.” Carrie giggled and Marcie smiled. “I am four years older than you. I think you are a nice guy and I know you are super smart, but I am not going to be your girlfriend.”

“I appreciate that Marcie and I understand. I appreciate you being honest. Just don’t get mad at me if you catch me staring at your beautiful body or enjoying myself if they make me have sex with you again.” Mike smiled.

Marcie leaned in and gave him a peck on the cheek. “I don’t think I will mind at all. In the meantime, I need to get back to our favor.”

“Sure, what’s that?”

“After the session with the gags yesterday and all the talk about different stuff ... Carrie, you tell him.”

Carrie looked a little apprehensive. “Mike, I am a virgin and the most I have ever done with a boy so far is kiss and let him feel me up. I have never given a boy a blowjob. Frankly, I want to know what I am doing and would like to have done it with someone I like before having to do it to some old rich guy or embarrass myself in one of Master Brian’s training sessions. I was especially worried after hearing about ring gags, forced blowjobs and some of the other things.” She paused. “I like you, Mike. I want to give you my first blow job.”

Mike was stunned. Carrie was just as cute as her sister but still a year older than him. When they compared birthdays, it was more like 6 months older. Here was this very pretty girl asking him to put his cock in her mouth.

Marcie seeing Mike’s shocked expression said “This is only if you are willing, Mike. When she told me her concerns, I thought immediately of you as her best option. Besides, I thought if she could learn to do it with that monster you own, she would be ready for just about anything.”

Mike blinked and started to run all kinds of ramifications to this in his head. “What about your mom and dad? Do they know about this?”

“No, we didn’t tell them, Mike.” Carrie spoke seriously and obviously had thought this through. “I will tell them later but knowing them and the situation we are all in here, I know they will understand and support my decision. I even think they will appreciate you doing this. We were more concerned with breaking some kind of slave rule and that’s why we checked with Master Brian before coming here. He thought it was a great idea and actually complimented me on my initiative and attitude.” She was proud of that last statement. “Oh, he warned me that I was not to lose my virginity. Apparently, they have something special planned for me for that. Understand, there are no strings attached here. I don’t expect us to be boyfriend and girlfriend because of this. It’s just sex.”

“Wow, I am flattered you chose me for this and I would be insane to turn down a blow job from such a beautiful girl. So, my answer is a ‘hell yes!’ So, when do you want to do this?”

Carrie smiled and took off her bikini top. “No time like the present, silly.” Carrie’s breasts were small but beautiful. Mike didn’t consider himself an expert, but he guessed they were an A cup compared to Marcie’s C cup breasts. He was getting hard looking at her erect nipples.

He thought they should go in his bedroom but Carrie led him over to the couch in the living room and pushed him to sit. She had a dreamy look in her eyes as she sunk to her knees. Marcie knelt beside her. Mike was already in heaven watching two gorgeous redheads with their faces so close to his crotch. Carrie saw his erection outlined in his shorts. “Jeez! You weren’t kidding, Marcie!” Carrie ran her hand over the cock and could feel the heat through the sheer fabric. She moved her hands to the waist band on either side and started to pull his shorts down. Mike lifted his butt to help her. His cock, now released, sprung forward toward Carrie’s face. She moved forward and pressed it to her cheek with her eyes closed.

Marcie moved close to her sister and spoke softly, almost in a whisper. “Wrap your hand around it and move it up and down firmly but don’t try and squeeze it. I usually start by licking up one side and then up the other from bottom to top just with the tip of the tongue. Try it.”

Mike and Marcie watched Carrie as she gently licked as directed. “Now lick the front of the cock just below the head. That is one of the most sensitive spots.” When she did, Mike rewarded Carrie with a throaty groan that made her smile so she did that several times and she enjoyed how it made the cock twitch. “Now you can do just that to make a guy cum and he will probably do it on your face, but I have a feeling most guests will want you to suck on it. So, let’s move on to the main event. Move up and open your mouth as wide as you can, but still cover your teeth with your lips. The teeth can hurt a guy so you need to be careful not to scrape him. Put the entire head in your mouth and stick your tongue out when you do it. Make it wet. Don’t worry if your slobber runs down his cock. Making the cock wet is good, especially if you are going to fuck him.”

As Carrie managed to get the head entirely in her mouth, Marcie said “Remember what I said about that spot just under the head? Your tongue is on it right now. Try flicking your tongue back and forth over that spot real fast and licking up and down while the head is in your mouth.”

Mike groaned “Uh, I’m not going to be able to hold out much longer. This is pretty intense.” Hearing Marcie’s description of everything was also setting him off.

Marcie gave Carrie her next instruction. “OK, Carrie you’re doing good. Mike is about to cum. We talked about this. You are going to take it in your mouth. Hold your hand around the base and move it up and down and keep moving your tongue.”

Mike yelled “Here it comes!” Carrie’s eyes went wide as saucers and her cheeks puffed out as Mike unloaded in her mouth. She froze making sure he was done and then let the head slip from her mouth still holding the cum.

Marcie looked her in the eyes “Hold it in there and get used to the taste. I know its not real tasty right?” Carrie was frowning and she nodded her head obviously not enjoying the taste. “OK. Now swallow it.”

Carrie made herself swallow with her eyes squinted tightly as she did. “God, that tastes awful.”

Marcie laughed “Remember the first time you tasted coffee or had a sip of Dad’s beer? You thought that was awful too, but then the next time you kinda got used to it and now you like it. You may or may not get to the point where you like the taste, but the more you try the more you will get used to it. Mike, do you have a soda or something in your fridge?”

Mike was drained and weakly pointed to the kitchen “Sure help yourself to anything.”

Marcie found a diet ginger ale and gave it to Carrie. Carrie swished it around like it was mouthwash and felt much better.

“Carrie, that was the best thing that I ever felt. I mean it! Any time you need more practice, just let me know.”

Carrie beamed a bright smile at Mike. “I will keep that in mind, Mike.”

The speaker in the ceiling clicked on. “That was the hottest thing we have seen in some time. You got just about every guy in the control room hard as a rock. Thank you!”

The three of them cracked up. Carrie looked to the ceiling laughing. “Glad you guys enjoyed it, but probably not as much as Mike did.”

Marcie looked at Mike and gave an evil smile. “Keep watching guys because we are far from done with this lesson. Cassie, now that Mike has cum, he will last much longer the second time”

Mike looked at Marcie “What? A second time?”

“Carrie needs to get a deep throat lesson. Stand up, Mike.” Marcie then removed her own bikini top as Mike enjoyed the view from above. “Watch carefully, Carrie.” Marcie took Mike’s now soft dick in her mouth and sucked until it grew and was again ready. After a few strokes in and out, she pressed forward and took his cock all the way to the base and into her throat.”

Mikes eyes popped open wide. He could not believe Marcie swallowed his entire dick. Carrie was kneeling right beside her sister also watching in disbelief. Marcie released the cock and pointed it at Carrie. “OK your turn.”

Carrie looked worried but she took it in her mouth remembering her earlier lesson and covered her teeth. Marcie moved so her face was right next to her sister’s. “Move back and forth a few times like you did before. Good. Now go as down on it as far as you can.” Carrie got about half the cock in her mouth and she gagged as it hit the entrance to her throat and her eyes teared up. “That’s OK. That was your gag reflex and that’s normal. I want you to go back and forth again and when you are ready try to take it all the way down. When you feel it at your throat again this time, pretend you are swallowing some food. Pretend you have a large piece of your favorite food in your mouth you want to swallow. Ready?” Carrie nodded and descended on the cock. When it hit the back of her throat she swallowed and Marcie pressed her head forward. It hurt like hell but she felt Mike’s pubic hairs brush her lips. “You did it! Now one more time.” Carrie took another deep breath around the cockhead and pushed back down. This time she did it on her own. It still hurt but not as bad.

She backed off and released the cock. “Wow! I can’t believe I did that! It did hurt like hell though.”

Marcie hugged her sister. “It gets easier the more you do it. You did it and that’s what is important. You are just as ready for oral as any other woman here.”

The overhead speaker clicked on again and they heard applause. Carrie cracked up again. It was strange to do this with an all watching audience but she kind of appreciated the encouragement and fan club. Her sexual self-confidence just got a major boost.

Mike in the meantime had sunk back onto the couch with his still hard cock. Marcie saw and wrapped her hand around it. “Cassie, Master Brian said you can’t do this but I still can. I want to try this big guy out.” Marcie stood and removed her shorts to reveal her neatly trimmed red landing strip on her pussy. She straddled Mike who realized if Carrie was holding onto her virginity, he was about to lose his. Marcie positioned his cock at her entrance and sighed “Oh, yes!” as his thick member stretched her open like none of her boyfriends had never done. She sunk all he way down as Mike stared at her awesome boobs bouncing with her movement. Cassie moved to the couch beside him, grabbed his face and kissed him driving her tongue into his mouth. Soon he felt his second orgasm build and explode.

Marcie collapsed against his chest pressing her breasts to him as Cassie nuzzled his neck. He was on cloud nine. Whatever he had to do in the next year, he believed this moment made it all worthwhile.

He opened his eyes and over Marcie’s shoulder he saw his twin sisters back from the pool and standing in the entry with their eyes and mouths opened wide.

Mike and his sisters showered before going to class. His sisters showered to get the chlorine from the pool off and Mike for other reasons.

Mike was glad he had the breakout with Slave Eddie on quantum math theory. Eddie was impressed by the 14-year-old’s grasp of several theories and encouraged Mike to research some additional concepts. The resort provided tablets with extensive libraries the teens could use for their academic studies. They had no internet connection but queries could be made and if within preset and AI parameters of the resort’s rules for slaves, the internet result would be returned to the user. Mike was only a tad disappointed that internet gaming was not one of the allowed uses.

The math session Mike would have otherwise attended was on differential equations that would have been boring for him. Pam and Tammy were making progress on that topic but still struggled grasping some of it.

They all met up with their mom and dad in the cafeteria for lunch after their parents’ morning work assignments. They were told their workday would be expanded after their slave orientation was complete as long as they were not called by a guest. Joni did not mention she had to give another blowjob before leaving for lunch today. Neither Mike nor his sisters discussed what happened back at the house with Marcie and Carrie. After lunch they headed to the second scheduled slave training session with Master Brian that was on the agenda for all 16 new slaves.

SALES TRAINING

Master Brian greeted the new slaves as they entered. When Marcie and Carrie entered, he smiled at them. “Ladies, great job today. I am very glad to see you taking initiative like you did.” Henry and Mary both looked at their daughters with curiosity.

Carrie cut off any questions from her parents “We’ll tell you about it later.”

A few minutes later all five Clarks walked in together. When Master Brian saw Mike, he gave him a pat on the back and smile as he entered “Glad to see you’re still walking big guy.” Mike blushed. Tammy and Pam both giggled leaving Jon and Joni curious as to what that was all about.

Once everyone was seated Master Brian started the lesson for the day. “Today we are going to discuss role playing with guests. Our guests are willing to spend a small fortune and travel long distances to be here. They are doing this because we can give them something they cannot safely obtain anywhere else in the world. That something is to fulfill their most secret fantasies without anyone judging them. Mostly, but not always, those fantasies are sexual. In the years I have worked here I have made the mistake, more than once, of thinking I have witnessed every kind of desire that can be requested by a man, woman or LGBTQ ... XYZ whatever. Each time I thought that, I was wrong.”

“Before a guest comes to our resort they are carefully vetted, both from a financial and security standpoint. Most are referred by previous trusted guests and many make regular trips here. Part of the vetting process for first time guests is an interview to uncover their innermost desires. Many of these are pretty straight forward activity that excites them sexually. They cannot get find partners or anyone else to fulfill their more unusual desires in their private lives. Most often these involve the control of someone sexually or being controlled by someone in a very particular manner. Sometimes the fantasy includes a particular hair color, breast size, penis size or ethnicity. Some involve certain combinations of details like watching a white man being pegged by a black woman while getting blown by the man’s wife. Many of these fantasies are deeply rooted in childhood memories or traumas. Others may be fetishes like shoes or fucking a mature woman dressed as a nun that used a ruler on their butts when they were 10. We take great pains to ferret out these details.”

“My point is, we do not judge. We accommodate. We expect the unexpected. We will do our best to stage the fantasy to the best of our ability but there are always gaps that must be filled in by you. You need to often sensitize yourselves to what is turning the guest on and what brings them down. You need to be observant. If the client is paddling you, maybe you can stoically take the paddling without complaint but if the guest wants you to cry and beg them not to hit you again, do it. If they want to hear you say you will do anything for them not to hit your butt again, say it. You may be actually enjoying sex with the guest but if they want you to pretend you are being raped, do that. On the other hand, you may find the sex boring and uninspired but if they believe they are the world’s best lover, you will learn to convincingly fake orgasms and sexual ecstasy.”

“Any questions so far?”

Tammy raised her hand and Master Brian pointed to her. “Sir, how often will we be beaten and how hard. I am not sure how much pain I can take without losing it.”

“I’ll level with you. It won’t happen every day but you can expect some sort of corporal punishment in the guests fantasies at least a third of your encounters. That can include being whipped or spanked on various body parts or uncomfortable restraint. But we have ways of making these less painful and less traumatic. You will receive some training and conditioning before you have those encounters. Some of you may be getting some taste of that training in the second part of today’s training. Yes, you will experience pain from time to time, but you will not be permanently marked or injured. Before you ask, most of you, both male and female, will experience anal penetration. For those not experienced in anal sex, that thought can be scary. We have ways of preparing you for that so it will not be so painful or scary and even pleasurable with the right attitude. That discussion will be for another session for another day.”

“By the way, are you Pam or Tammy.”

“Tammy sir.”

“I am going to need some lessons in how to tell you two apart.”

Pam spoke up. “I’m the pretty one, sir.” The whole room cracked up including Master Brian.

“You are both beautiful and I love the idea of how much you look alike and so will many guests. You may be surprised how many fantasies involve twins.” Tammy shivered involuntarily at that news.

“We will do our best to give you an idea of what to expect before meeting with a guest. This information isn’t perfect but it is, more often than not, spot on. Many of our guests are repeat customers that want the exact same thing each time they visit and they just want variation in the slave that participates. Other times, on more difficult cases you may be given an ear piece to help coach you through a session but creativity and the ability to think on your feet, or on your knees, is always valued.”

“Let’s take a break. If you even think you need to use the bathroom, I advise you go now before the next lesson.”

TRAINING: STOCKS AND BONDS

When the group reconvened, Master Brian was joined by Slave Katie and Slave Ron. This was the married couple that were part of the previous day’s training. As was done yesterday, for this session all slaves had to strip off their slave outfits. Jon noticed how different everyone’s attitude had changed in just one day. There was almost none of the self-conscientiousness about being naked in front of family members and friends that was so prevalent yesterday. It was like a watermark to him on fast they were being transformed into compliant slaves.

To start this session Master Brian lined all 16 slaves up shoulder to shoulder. He told everyone to count off starting with Debra who was at the left side of the line. “Count off 1,2,1,2...”

He told all 2’s to take one step forward. “All 1’s will be pretend guests and all 2’s will be their slaves.” They all looked down each line they were in. The ‘clients’ ended up being Debra, Anthony, Zoe, Mary, Carrie, Tim, Jon, and Tammy. The slaves were Jill, Vicky, Henry, Marcie, Ellen, Joni, Pam and Mike. They then marched the line of slaves around to the other line of clients. Mike became Debra’s slave, Pam was Anthony’s, Joni was Zoe’s, Ellen was Mary’s, Marcie was Carrie’s, Henry was Tim’s, Vicky was Jon’s and finally Jill was Tammy’s. The randomness created some interesting combinations. There was girl on guy, guy on girl, girl on girl and guy on guy. There was even a sister on sister. Everyone was nervously thinking about how these pairings would pan out. The designated slaves were especially nervous.

Mike and Debra were directed to the first device in the room on the left. This was a padded bench. Mike was directed to lay over the bench face down. “Debra secure Mike in place.” Katie and Ron showed her how to secure his wrists with cuffs near the floor on one side and his ankles in cuffs on the opposite side. There was a toggle button on the side of the bench that raised the top of the bench until Mike was stretched tightly over the device with his ass exposed and legs spread. “This is an adjustable paddling bench that can be raised or lowered depending on the slave’s height. The motor has a failsafe that will not exceed a tolerable PSI so the slave is not stretched to the point of injury but it will put a strain on the arms and legs. Are you feeling it Mike?”