Hindsight 20/20 Book 4 - Johnny's Story - Cover

Hindsight 20/20 Book 4 - Johnny's Story

Copyright© 2017 by SmokinDriver

Chapter 7

Coming of Age Sex Story: Chapter 7 - This is book 4 in the Hindsight series. It is a stand alone story but makes references to previous books. This is the story of a boy that goes through life following the example of his friend Britt. It is a coming of age story. It will take him from high school, through college and into his business life. Thanks for taking the time to read my story.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa   mt/ft   mt/Fa   Consensual   Fiction   Rags To Riches   Cuckold   MaleDom   Harem  

Author’s Note: The following section has scenes including cuckolding, slut wife, wimp husband. If you don’t enjoy those kinds of stories, please skip to the next chapter to continue.

Graduation was finally over and students and faculty hung around with family members, congratulating each other and saying goodbye. Some of these people you would never see again. I was leaving in a week to start my summer work. It was Friday night and I didn’t want to go to some high school party and get hammered. I didn’t see the point in it so I was planning just to go home and relax before my summer of travel started.

Mrs. Phillips walked over and congratulated me on graduating. We were alone in our conversation when she leaned in and said, “Do you think that we could get together and talk sometime this summer?”

“I’m only going to be in town for another week before I’ll be off working for the summer in Florida. Then I’ll be attending the University of Florida. Was there something specific you wanted to talk about?”

She looked around to see if we might be overheard. When she observed that no one was listening in on our conversation she said, “Maybe we can talk tonight if you can get away. There was a favor that I wanted to ask you.”

The way she was asking led me to have an idea about what the request might be. “Meet me at the lobby bar at Bally’s at nine tonight.” It wasn’t a question or a suggestion, it was a command. She now had to decide if she would follow it as I turned to go back and let my family know that I was ready to go home. I didn’t even look back to see Mrs. Phillips or what kind of look she might have had on her face.

I mentioned to Darcy that I would be using the suite and she just smiled and told me to have fun and be safe. Mom’s approval was about the same as Darcy’s. Before I could leave, the phone rang and Pam wanted to see if I wanted to get together to celebrate graduation. I told her that I was busy but if she was free the next day, she could stop by the suite at Bally’s after 11am. She told me that she’d try to make it but would have to talk to her mom first.

After dropping a bag in the suite, I made sure that everything was in order. I took the elevator down to the lobby and walked into the bar at 9:01. I saw Mrs. Phillips watching the door. I was surprised to see her husband sitting next to her in the circular booth they occupied. I hadn’t done anything wrong so walked over to where they were sitting and slid into the booth with Mrs. Phillips between me and her husband.

She seemed like a young woman in her late twenties but her husband seemed a little older by maybe ten years. His thinning hair might have made him seem older but they didn’t look like high school or even college sweethearts. Mrs. Phillips introduced me to her husband as Bo, not as Mr. Phillips.

I was again congratulated on my graduation and acceptance to college. A long silent pause fell over the table while Mrs. Phillips gained her courage. She took a drink of her cocktail before saying, “Jack, this is hard to ask but ever since the beginning of the year, we’ve been living our sexual fantasies based on your stories. I at first thought you were making everything up. The more I overheard Pam and then Christy, I came to believe that what you were writing was the truth.

“Bo and I met when I was first hired as a teacher in Phoenix. He was principal of the high school. We were sexually attracted and got together soon after I started. When we decided to get married, we couldn’t stay at the high school with that relationship so we moved to Vegas. I teach at one high school and Bo is the principal at another one. We’ve always been very open and honest about what we wanted sexually since our relationship was built on sex first until we had time to find out who each other was as a person.

She took a deep breath as she was about to say what we were all there for. “I let Bo read your first story and every one since then. I have fantasies to be in that kind of relationship. Not forever but to live out the fantasy. You’re no longer a student and I know that you’re 18 so legally I won’t get fired or go to jail. As Bo and I spoke and I told him about my fantasy, he told me about his as well.” She looked at her husband and he looked at the table top.

“Bo has a fantasy about having another man take his wife and use her as he wishes. There is even a name for this fantasy. It is called cuckolding. For the last three months that seems to be all that we think about or talk about in the bedroom and we want you to help us fulfill our fantasy.”

I didn’t answer immediately even though I knew that I would say yes. I wanted them to sweat for a minute and let it sink in that I would be doing them a favor and not the other way around. I loved the feeling of power and from the few times I’d been in group environments, I didn’t have any problem performing sexually in front of others.

Looking at Bo, I put my hand on Mrs. Phillip’s thigh. “Bo, is this what you want?” I looked around to make sure there were no eavesdroppers. “Do you want to watch while I use your wife as my own personal fuck toy?”

He didn’t look away but just nodded.

I flagged down the waitress and ordered a Jack and Coke for me and another round for Mrs. Phillips. Nothing was ordered for Bo. I also asked her for a pen and something to write on. She came back with everything I asked for. I wrote down a few things on the piece of paper.

As I handed the paper to Bo, I said, “Bo these are the things you need to get for our time together. Everything else, I’ll take care of. I have the penthouse suite in this hotel so take the elevator to the top floor and take a right. The double doors at the end are mine. Meet us there when you get everything on the list. If you brought a bag or suitcase, get that while you’re out.”

He’d been dismissed and I turned to Mrs. Phillips, “What’s your name, Little One?”

A shiver went through her body as she replied, “Elizabeth but my friends call me Beth.”

“Liz, it is. Liz is this what you both want? Is this something that you want and something that Bo wants? I’ll be gone in a week and this can make or break your marriage if you don’t both want this. I won’t feel bad either way but it won’t be as easy as you might have imagined.”

“We both want this and Bo maybe more than me. He’s always been in charge and accountable but his fantasy is more about just the opposite. He wants to be humiliated. He feels like he has gotten away with something he might not have deserved since he was promoted to principal at such a young age. Maybe this is a penance or just that he feels that his manhood isn’t up to what a man should carry to deserve a woman as pretty as me. I’m not saying that in conceit but that is what he’s said. He wants me to get the larger cock that a woman like me should have. He definitely wants to watch me get fucked by a big cock and from what Pam says, compared to other boys and men, you’re both longer and thicker than average.”

“Finish your drink Liz. We’re going to see if I can rock your world.”

She downed her drink in one long slug. I finished mine in two sips. I paid the bill before leading her to the elevator. When the door to the suite closed behind her she stopped and was in awe at the size and luxury before her. She said, “I was told that you had money but this is quite extravagant.”

“Get naked for me now, Liz. I want to see what I have to work with while we wait for Bo. While you undress, tell me about what you see in your fantasies. I won’t guarantee that I’ll follow your script but I may incorporate it into what we actually do.”

“As you said, I want to be your fuck toy. I want to do as you order me. I am clean but not on the pill. We’ve been trying to get pregnant for a few months now but it hasn’t happened. You may see that Bo isn’t that big down there but he does make sure that I get my orgasms. He’s an attentive man but just wasn’t blessed in that area. I think it has given him some kind of complex or something.”

She was naked by the time she finished but when she saw me looking at her she started to get nervous and move her hand to cover herself. “Liz, you can call me Master or Sir. Don’t you even think about hiding your body from me. Until we go our own ways, you belong to me. You’re my graduation present from Bo. He gave up any claim he has on you until I give you back to him. Do you understand me?”

“Yes Sir.”

There was a knock at the door. I motioned with my finger for her to stay where she was and I went to open the door. Bo had a small suitcase and a bag from the drug store in his hands. I let him in and he took in a deep breath when he saw the massive suite with his wife standing naked before him. The door closed behind him with a heavy thud.

I took the bag from Bo and pointed to a place off to the side for him to put his suitcase. Walking into the living room I told Liz to follow me and Bo came along as well. They sat on the couch across from me when I motioned them to.

“Bo, you can get naked as well. We need to set some expectations and rules now on the front end. I don’t want to have any second thoughts or misconceptions once we start.”

Bo stood and got naked before sitting down next to his wife. Liz and I both watched. He was already hard and stood at about four inches and his balls were very small. I was taking the items out of the bag as I spoke.

“Bo, Liz, this isn’t a game. This is real. I want you both to listen to what I am going to say. I am only 18 but I’m a man. A man that knows what he wants and takes it. I am going to take Liz. She will be mine until I say that we are done. At any time, you can use a safe word. The safe word is “Elephant.” Remember that if the safe word is used then the date is over. If Bo uses the safe word, then it is over for both of you. If Liz uses the safe word, then it is over for both of you.”

They were both nodding their understanding and agreement as I continued, “You can say, stop or no but that will probably just get you punished but it won’t make me stop. I am the one in control here. Are there any questions and do you agree to my terms before we start?”

Liz spoke first. “I understand and agree to your terms, Sir.”

Bo followed with the same words.

“Alright, I told Bo to buy a few things. I told him to buy condoms, scissors, razors, shaving cream, and KY jelly. He did well and bought everything. When I tell you to, you’ll go into the guest bathroom. You can take your suitcase and the razors. Bo you’ll shave your wife from the neck down. Underarms, pubic hair, legs, arms, you’ll shave her bare below the neck.”

Bo was nodding as I continued, “When he’s done, Liz you’ll shave Bo. I want the same thing. Everything below the neck.” Bo looked surprised but didn’t say anything. Liz saw him accept his fate as his shoulders slumped. She nodded.

“Don’t take all night but take your time to do a good job. You can talk while you’re in there. When you’re done, you can wash your bodies. You’ll not fuck or suck each other. You’ll shave and wash. Use the restroom if you need to. I don’t know the next time I’ll be so generous. You may start.”

This was the last time to discuss what they had gotten themselves into and back out if they chose. They also were making a commitment or an investment into their fantasy. I gave them privacy and made sure that Darcy’s stock of toys and restraints were where they should be. I put a towel on the club chair beside the bed in the master bedroom. They were in the second bedroom and bath.

It did take a while but I waited patiently as they completed their tasks. When they came back into the room, they were both shaved smooth. They stopped at the end of the coffee table, waiting for their next command.

“Look at my bitches, smooth as babies. Bo, take the KY jelly and condoms into my bedroom. I may need them. You’ll sit in the chair, on the towel and you won’t get up unless I instruct you to. You may play with yourself as you watch me fuck Liz. You may cum but must ask permission from me and get approval before you cum. Do you have any questions about your instructions?”

“I don’t have any questions, Sir.” He picked up the condoms and KY Jelly and walked into the bedroom.

“Liz, you look delicious. Come into the bedroom with me.” Taking her hand, I led her to the bedroom. When we got to the foot of the bed, she and Bo were both looking around at the room. They could see a flogger and some restraints next to the bed on one nightstand. There was an assortment of dildos, vibrators, and butt plugs on the other nightstand.

Their eyes were big; they seemed a little more nervous as they fidgeted where they were. “Liz, undress me.” She started to unbutton my shirt as Bo stroked his smaller cock. I stood in a way that Bo could see me from the side and when my shirt was off and hung in the closet, Liz knelt to take off my shoes and socks. She stayed on her knees as she undid my belt and pants. She slipped my pants and boxers over my ass and my now eight-inch, thick cock fell to parallel to the floor and hit Liz in the forehead.

Liz remained focused on getting my pants off over my feet when Bo started to get up. “Sit down bitch.”

He seemed very flustered. “Sir, I need to get a towel or a tissue.”

“Bo, I said that you couldn’t get up unless I told you to. Maybe you didn’t understand me. Next time you stand without permission, you’ll be back in the other room getting your head shaved and the next time your eye brows. You can cum on your stomach, hands or use a condom but don’t get up.”

“Yes, Sir, I’m sorry, Sir.”

He got out a condom but the larger size didn’t quite seal around his cock very well. He kept stroking his cock and Liz was back from putting the rest of my clothes away. I nodded to her and she went back to her knees.

“Kiss it, Liz. This cock is going to bring you a lot of pleasure. Let it know how appreciative you are for the attention it will be giving you.”

She had kissed it and was just starting to lick when Bo spoke up, “Sir may I cum?”

We both looked over at him as he had his legs spread. His hand was moving frantically and there was a look of desperation on his face. “Yes, my little bitch, you may cum.”

He grunted as he filled the condom. He took off the condom and sat back in his chair to watch. Liz went back to kissing and as I gave her small commands, she sucked me into her mouth and used both her hand and mouth to give me a very good blow job. I looked over to Bo to see that he was hard again and had another condom on his cock as he stroked himself.

Liz was doing well but I stopped her and had her take the comforter off the bed as I got another towel to put under her and positioned her on the bed. I started in with my mouth on her pussy as I rubbed, smelt, tasted, licked, and sucked on her. She was starting to moan when Bo interrupted again, “Sir, may I cum?”

“Yes, my little bitch.”

I went back to Liz and was enjoying her pussy as Bo again filled the condom. Liz was loud in her pleasure and her pussy was wet and inviting. She was vocal in her praise. I stood and walked over to Bo. He had only bought a small box of three condoms when he was sent on his errand. I noticed that out in the living room when I opened the bag. His instructions were to buy condoms. Here we were barely starting the session and We were almost out of condoms. Sounds like a problem that he created. Maybe he would tap out and use his safe word.

I walked over to where Bo was sitting and picked up the last condom. I handed it to him. “If you want me to wear a condom with Liz, then put it on me.” The look on his face let me know that he planned on just sitting back and whacking off all night while he watched the live sex show between his wife and me. Reality was starting to set in. He could let me fuck his wife bareback or use the safe word and not have to touch me. The other alternative would be for him to take my cock in his hand while he rolled the condom on. He didn’t hesitate long before he was opening the condom and rolling it down my shaft. He could feel the thickness, weight, and length as he rolled it out.

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