What a Deal! Ch. 21

A reminder that this is part of a Non-Consent/Reluctance series. If you don't want to read about sex where someone is put into that position, then stop now and move on.

This is a continuation of what would be considered a "stroke" story, or as I like to call then a Jack(off) and Jill(off) story. I got some requests to continue this not very serious, fictional sex romp, so I'll try to keep up.

In the last story, Bill and Suzanne opened their home to 'Princess Time'. A couple of women on a Saturday would schedule a time with Bill and he would do whatever they wanted for their visit. Well, at least when it came to bathing them and shaving them. He would shave their underarms, legs, and then their pussies however they wanted it. He was also offering a final orgasm via cunnilingus. He was not allowed to fuck them. But after a couple of times, Suzanne allowed Brittany to take over as Bill's assistant with a few rules. They seemed to work out well.

Recurring Cast

Dennis, 41 years old, 5' 11", 175 lbs, brown hair, blue eyes, Cindy's husband.

Cindy, 41 years old, 5' 4", 105 pounds, brown hair, blue eyes, Dennis' wife.

Diane, 41 years old, 5' 7", 140 lbs, auburn hair, green eyes, recently divorced friend of Cindy's.

Becky, 38 years old, 5' 9", 155 lbs, blonde hair, blue eyes, Cindy's friend, widow.

Jack, 42 years old, 6', 185 lbs, black hair, brown eyes, Louise's husband.

Louise, 38 years old, 5' 4", 130 lbs, blonde hair, brown eyes, Jack's wife.

Jackie, 19 years old, 5'6", 125 pounds, dark brown hair, blue eyes, neighbor girl.

Katy, 19 years old, 5'6", 115 pounds, blonde hair, blue eyes, Jackie's friend, now Dennis' sub.

Suzanne, 36 years old, 5'5", 125 pounds, brown hair, brown eyes, neighborhood acquaintance.

Bill, 38 years old, 5'9", 170 pounds, black hair, brown eyes, Suzanne's husband.

Brittany, 27 years old, 5'8", 120 pounds, red hair, blue eyes, Jimmy's wife.

Jimmy, 29 years old, 5'10", 160 pounds, brown hair, brown eyes, Brittany's husband.

*****

A couple of weeks later, things were going pretty well for me at work, when my boss called me into his office. We were expecting a visit from a potential customer - one who could possibly make our entire year with one signature.

"Dennis, any chance you can help me out?"

"Uh, sure, Roger, what's the problem?"

"Well, Mr. Sorenson, the CEO who is coming to visit and hear our pitch, is a bit of an old perv. The last time we tried to sell him on our product, he asked me to take him to a strip club. I did, although you know that's not my style. I paid for lap dances, private dances, and every other kind of dance, but I drew the line when he seemed like he was trying to convince one of the girls to go back to his room." He sighed and ran his hand over the top of his head.

"He really asked for that?"

"Oh, yeah. He was all over those strippers and they were loving it. He's quite gregarious and they thought he was hilarious."

"Okay. Well, do you just want me to do the strip club and see what happens?"

"Yes, please. I can't do it again."

"Well, I'll talk to Cindy. I'm sure she won't mind. I'll handle it."

Roger smiled at me. "Thank god. I don't think I could handle him again. But we need this guy. We need to get his business. I don't know that it's necessary or that he will base his decision on this. I just know that if he signs he'll make our year. And there will be something for you if he signs."

"No problem. I know what to do."

Roger smiled. "Thanks, Dennis. I was hoping that your wife might be a little more understanding than mine."

"Alright. I'll get his hotel information from Lisa." I left and stopped to get the information from Lisa, his secretary. He was staying in a very nice suite at one of the better hotels. I knew what to do.

I headed for home and called Suzanne on the way. I wanted her along on this ride. She agreed to meet at my house and I then called Cindy and Katy, too. I wanted them all there when I got home.

I then called Taylor Sorensen. Who the hell has two last names like that? Anyway, tonight was supposed to be our night out, so I arranged to call on him at his hotel at 8pm. I told him that I would come up to his room.

I arrived just in time to see Suzanne pull into the driveway. She got out and I met her on the walk up to the house.

"So, you want me to fuck some old guy?" She said it partly in jest, but there was just the hint of feeling put upon.

"Well, let's get inside and I'll explain."

We went into the house and Cindy and Katy were at the kitchen table. I then went into an explanation of what I had in mind. They all nodded, asked questions, and modified my plan, but in the end they all agreed. Suzanne had one other requirement.

"Now if you get this guy as a customer, I expect fair compensation."

"Well, won't that make you a 'woman of the evening'?" I grinned at her.

"Fuck, no. It just means I'm getting paid for landing a big fish for you." She punched me in the shoulder.

"Okay, let's get everything ready."

Everyone went to get ready for what I had planned.

At about 7pm, we all gathered and got ready to head downtown. We piled in the car and headed down there. Katy was laughing and smiling and full of energy. Suzanne looked over at me and rolled her eyes at the youngster.

"Okay, here we are." I pulled into the parking garage of the hotel. "You guys come up, but wait down the hall while I explain what I have in mind to Mr. Sorensen."

We all got out of the car and headed into the hotel. We rode the elevator up to the 15th floor where his suite was. The ladies waited in the alcove outside the elevators while I went to his room. He opened almost immediately when I knocked, even though I was 20 minutes early.

"Hey, Dennis, I'm Taylor." He put out his hand and we shook. "Come in."

I entered and looked around. It was perfect for the scenario I had in mind. "Nice suite."

"Thanks. I always travel in comfort."

"So what ideas did you have for tonight?"

"I'm sure your boss told you. For the last few years, I've enjoyed going to the strip club and playing with the strippers."

"No family back home?"

I said it quickly and slightly in jest, but the look on his face told another story. He suddenly looked much older than his age, which I put at around 60.

He looked up at me. "It's a long, terrible story, but the short version is that my wife died three years ago of cancer and my two children live on the other side of the country. They are very busy and I only see them when I travel to see them. They never visit me."

"I'm sorry. I didn't mean to go there."

He gave a sad smile. "I know. But after she died, I just decided to enjoy myself and to hell with what happens. I run my company and enjoy strippers. I suppose it could be worse."

"Well, then, I think you will love an idea that I have."

"Yeah? What do you have in mind?"

"Do you like role-playing?"

"Uhhhh - like what?"

"I happen to have three ladies outside waiting for us. One is going to take a video of the proceedings, if you want one. The other two are prepared to play a teacher and her unruly, slutty student, who is being brought to you, the principal and me, the vice-principal."

He grinned. "Now that scenario certainly seems to have promise. What are the rules?"

"The rules are that one, you must enjoy yourself and two, you need to take advantage of these ladies however you see fit because they love to suck and fuck."

He stared at me for a moment. "Where the hell has Roger been hiding you all this time?"

I shrugged my shoulders. "He doesn't know. Nor do I want him to know. This is just between the two of us."

"Fair enough. So, when do we start?"

"Let's just rearrange the furniture a little."

We moved the desk so it was facing the door coming into the bedroom at the end of the bed. We set it up so that Suzanne and Katy would come in from the front room of the suite and face the desk like in an office environment. Once that was finished, I went out and collected the ladies. They were still sitting and talking on some chairs outside the elevator.

"Okay, he's more than ready. I should tell you not to say anything about his wife. The reason he's out playing with strippers at his age is that he thinks he has no real life left. His wife died from cancer a couple of years ago and his kids live on the other coast and don't visit. Basically, he's alone and lonely, and has money to burn, so this is his outlet. So no mention of the family." I looked over at Suzanne. "Except, don't forget to mention that you are married as we discussed."

Suzanne smiled. "Don't worry. I know how it works. Men love the idea of conquering someone else's wife." She rolled her eyes at me and I grinned.

"You got it."

I went back into the suite and the ladies followed. They proceeded to get ready while I went into the bedroom and sat behind the makeshift desk. I looked at Taylor. "Ready?"

He smiled. "I guess so. This is certainly going to be interesting."

We sat there for a couple more minutes. "You sure you want it recorded?"

He thought about that. "Yeah, it will be great to look back on and remember."

"Okay."

And then there was a knock on the door. "May we come in Mr. Sorensen?"

"Enter."

Suzanne and Katy entered. Suzanne was dressed in a black skirt to her knees and a white blouse. She looked professional, but it was tight enough to show off her nice shape. Katy was a different story. She was dressed in the stereotypical schoolgirl outfit. Her white blouse was just barely opaque and you could see a hint of her areola. Her skirt was scandalously short. It was so short that you could almost see all the way to her panties.

Taylor and I stared as Suzanne directed Katy to stand directly in front of the desk. She was leading her by the arm and Katy was acting surly.

Cindy followed and was filming with a small video camera.

Suzanne stopped only a couple of feet in front of the desk and addressed us. "Mr. Sorensen, I know that you are new as the principal here, but we have a continuing situation that needs to be addressed. This is Katy." She spit out her name like it was disgusting and looked Katy up and down with disgust. "She's acting like a total slut most of the time. She wears her white blouses without a bra so that you can see her nipples." With that comment, Suzanne reached up and tweaked Katy's left nipple. Katy jerked back and it stood out hard and pointy. "See? And this skirt. She buys the correct length, like all the girls, and then like too many of these youngsters, rolls them up around the waistband to make them short and to show off their womanly assets." She turned to Katy. "Turn around." Katy did so. "See? You can almost see her butt cheeks hanging out and she's standing straight up! In class, she loves to lean over slightly, like this." Suzanne pushed on her upper back and Katy bent over to about 45 degrees. Her ass came into view and there was no sign of panties at all. Suzanne leaned over and looked at her ass. "See?" She lifted Katy's skirt. "And no panties either!" Katy's ass was entirely on display for us. Suzanne stood back up and put her hands on her hips, having made her point. Katy stood back up and turned around. She was grinning and looking quite smug. Cindy filmed the whole thing.

I took the lead. "Well, Katy, I can see that you have been very naughty." She continued to grin at me. "I guess you like to show off your ass and pussy to everyone, eh?" Katy looked at me, acting shocked at my use of the familiar words. Before she could answer, I continued. "Well, if that's how you feel, then drop your skirt and prepare for your punishment."

Katy hesitated, looking back and forth between me and Taylor. Then she complied. I think Taylor was a little shocked, but Katy just dropped it and stood there, her shaven pussy on display. Cindy was behind her capturing all the interaction.

"Now, you can choose one of two punishments. The first option is a week suspension. The second option is to accept a physical punishment here and now."

Katy looked at everyone. "I'll take the physical punishment."

I smiled at her "Okay, approach the desk, bend over and grab the far side. You will get ten spanks for this."

Katy approached and leaned over, grabbing the desk right between the two of us. I looked at Taylor and motioned with my head. We both stood up and walked around the desk and stared at Katy's ass and a hint of pussy. Cindy moved in and took some close-up views as we all looked. I turned to Suzanne. "Suzanne, stay here and be a witness to her punishment."

I put my hand out to Taylor to indicate that he should spank her. He approached and put his right hand on Katy's ass. She was breathing a little hard in anticipation.

"Now, be a good girl and take your punishment and we will let you return to class. Mr. Sorensen, ten swats please."

Taylor ran his hand over her ass one more time. "Are you ready, Katy?"

Katy nodded. And with that he drew his right hand back and smacked Katy on the ass. She jerked when it hit her, but didn't rise up. She just stayed there. Taylor looked up and grinned and hit Katy again.

I turned to Suzanne. "She does have a nice ass. I'm sure the boys love looking at it, eh?"

Suzanne looked at me. "Yes, it's very nice. She shows it off so much that they are used to it now. Sometimes when she passes certain boys, and some girls, they just lift her skirt and look at whatever they want, ass or pussy."

"Do you think she's enjoying this spanking?"

"Enjoying it?"

"Yes, do you think she likes to get spanked by an older, authority figure?"

Suzanne hesitated and looked at Katy. "Ummm, yes, it appears so."

Taylor had finished spanking Katy and was looking at the beautiful, red ass in front of him. I could see his boner stretching at his pants. This is what I had hoped for. It fit my planned scenario very well. I looked at Suzanne and she was also smiling at what was going to happen "Suzanne, she seemed to like it, so check to see if she's turned on."

Suzanne gave me her puzzled look. "What?"

"Check her pussy and see if being spanked got her wet." When she hesitated, I reached behind her and slapped her on the ass. "Go on, tell us if that got her excited."

Suzanne jumped when I swatted her ass, but she got behind Katy and looked at both me and Taylor, playing the scenario we had laid out. She then put her hand down between Katy's legs. Katy spread her legs wider to accommodate this. Suzanne ran her hand through Katy's gash and it came away wet. "Yes, she's very wet."

I took Suzanne's arm and lifted her hand up in front of us. She had two wet fingers. I took her index finger and brought it to my mouth and sucked it clean. She just stared. Then I pushed her middle finger toward her mouth. She opened it and sucked the finger clean.

"Taste's delicious."

Suzanne nodded and I turned back to see Katy looking over her shoulder at us.

I looked at her and then at Taylor. "Katy, it seems that you are very wet and excited. It also appears that you have made the principal very uncomfortable. His pants look way too tight, don't you think?"

Katy stood up and looked at Taylor's crotch. His erection was evident. She grinned. "Yes, they do look too tight." She leaned over and grabbed his crotch. "I would be willing to do anything to avoid another suspension, Mr. Sorensen."

Taylor grinned, playing along. "Well then, I think you should loosen up my pants to give me some room. I can't take having my pants so tight around my cock." He seemed to enjoy saying that and was loving this scenario.

"Yes, sir." Katy slid to her knees in front of Taylor and worked on loosening his belt and pants. They slid to the floor and we could see why his cock was showing so well. He was commando. His cock was not big, but sufficient. Katy grabbed it. "Nice cock, Mr. Sorensen."

Taylor looked up at me, grinned, and shook his head like he couldn't believe it.

Katy kept stroking his cock and he watched her as I moved around behind Suzanne. "That really looks hot, eh Suzanne?" She just nodded. I moved up against her ass and rubbed my cock around on it. I reached up and grabbed her tits. She moaned. "It's making me very hard, Suzanne. I might need help with my problem, too."

About that time Katy started sucking Taylor's cock. He was watching as Katy worked her magic, sliding her lips and down his length. He put one hand on her head.

I reached up and grabbed Suzanne's blouse. It was purchased with just this in mind. I found the two sides just under her tits and pulled with a quick jerk, ripping her blouse apart and sending buttons flying.

She grabbed what was left of her blouse and turned toward me. "Oh, Dennis! Please, I'm a married woman!"

"Yes, I know. That means you know how to do everything I'm going to make you do."

"But..."

I put my fingers to her lips. "Bend over the desk, Suzanne."

She stared at me and I could see that Taylor was watching us and Katy had stopped sucking his cock to watch. She held his cock in her left hand as she turned to watch this part.

When Suzanne didn't move, I got more commanding. She was supposed to act like someone who was submissive enough to go along with this.

"Suzanne!" I said it loud and she jerked at that. "Bend over the desk now. You need to also be taught a lesson. You have been staring at a naked student, felt her pussy, and displayed her body to us when you brought her in. You didn't even ask for permission to touch that student before you stuck two fingers in her pussy. You know what the rules are about touching a student. You have been very naughty and must also be spanked."

Suzanne hesitated. "Please, Dennis, I can't..."

"Stop!" She hung her head a little and was acting this out very well. Cindy was loving it and filming it closely. "Bend over and take your punishment."

Suzanne stared at the floor, then finally murmured, "Yes, sir."

Suzanne bent over the desk and grabbed the other side. Taylor and Katy were still watching and Cindy was directly in line with Suzanne's ass to capture this part.

I leaned over, grabbed the bottom of her skirt and lifted it quickly. Suzanne started to stand up, but I put a hand on her back. "Do not move. You will be punished like everyone else who breaks the rules."

Suzanne stayed there. "Now you will take your punishment like a good girl, right?"

"Yes, sir."

I stared at the beautiful sight before me. She was wearing thigh high stockings under her black skirt and a small black thong. It was wedged up into her pussy a little showing her lips a bit on each side. I pulled back and smacked her ass. She jerked, but kept her position.

I looked over at Taylor and Katy. Katy was standing up and coming over towards me, leaving Taylor standing there with his pants around his ankles and his cock waving in the breeze.

Katy looked back at him. "Take off your shoes, socks, and pants and get over here." Taylor moved to comply. Katy got to me. "You, too." Then she turned to the delicious ass being presented by Suzanne. Suzanne really did have a great ass.

Katy started running her hand over Suzanne's ass lightly. Suzanne didn't move. Then Katy ran her fingers from the top of Suzanne's ass crack, down over her asshole, and over her pussy. Suzanne squirmed a little under the light touch.

By now, both Taylor and I were naked from the waist down and standing with hard, upright cocks next to Taylor and Suzanne. Taylor looked down at Suzanne and stayed in her character. "I think Ms. Snooty Teacher here needs to be fucked."

Suzanne's head came up at that. "Please, no, I'm a married woman."

I looked at the arrangement and decided to change it up. "I have a better idea. Taylor is going to lay on the bed and I want you two to mount him. He needs to get his threesome fantasy fulfilled." Taylor grinned and moved to lay down on the bed. "Katy, put that hot teenage pussy on his face. Suzanne, sit on his cock."