Please, Mr. R. Ch. 02

“Fuuucckkkk.” I groaned as his face took liberties in my most private place. I shuddered at the thought that I might not smell clean and fresh and how I might be revolting to him with his face this close, and my bottom this open. I was almost at the limit of what I could take when I felt his tongue on me. Between the stress of bending over, keeping my legs straight and letting him pull me open and see me from behind, my legs were starting to tremble.

“Did you bring your camera with you?” Jay asked as I felt his tongue push through my vaginal opening.

“Oh, please!” I prayed silently to myself. “No pictures. Not that. Not now. Not like this.”

I felt him release the cheeks of my bottom and stand up behind me. Then without asking, he leaned over to my overnight bag, unzipped it and fumbled through it until he found what he was looking for – my digital camera.

Resting his hand on my naked hip, he patted me soothingly, saying, “You don’t have to worry, Sally. There will only be one camera here tonight and it will be yours. I’ll keep it with me the whole night and take some pictures for you. They’ll be your souvenirs of your fantasy and no one will ever see these pictures but you, not even me. I give you my solemn word.”

With that, Jay bent down behind me and I heard the familiar ‘beep’ of the camera turning on. “Bear with me, Sally.” He said. “I simply have to take a picture of you like this. I want you to be able to see what I’m looking at back here. The perfection of your nakedness and the way your cunt is opening up your sex to me is the most beautiful thing I’ve ever seen.”

So, I stood there while he took several pictures – extreme close ups between my legs – prying one of my cheeks apart so he could get pictures of my sloppy, wet cunt. I felt powerless to move, utterly shameful and humiliated, but I stood there – getting more and more excited with every picture he took. And, when he set the camera down on the bed and stood up next to me, I felt both relieved and sad this part seemed to be over.

Gently, I felt his hands caressing my shoulders. “Okay,” he said softly, “all done.”

Jay helped me stand up, and as he did, I felt a little dizzy and almost toppled over. He was quick to wrap his arms around me and pull me safely toward his chest, but in doing that, I had to shuffle my feet, and as I did, I felt my panties fall around my ankles. Jay lovingly patted my back and pulled away from me. “That wasn’t so bad, was it?” He said, looking into my eyes with his warm smile. His eyes were gently bending along with his smile and it wasn’t hard for me to smile back and shake my head ‘No’.

“Good, Girl.” He said, as his smile widened. “You’re very brave, Sally…… you’re doing well so far. I’m proud of you.”

Jay bent down in front of me without saying anything and reached out for the panties that were pooled around my feet. I bent over to see what he was doing, and as he grasped the sides of my panties and straightened them out, I immediately noticed how wet the crotch was. They were slimy with my cuntal goo, and the dampness was very apparent to me as I looked down into my panties. I knew he could see it, too, and instead of being embarrassed about my arousal, seeing the wetness in my panties solidified my resolve to give myself to him one hundred percent.

Just then, he looked up at me – catching me looking down at him. I saw his eyes drift down my chest and then come to rest below my waist. He wasn’t trying to hide his stare at all – and I stood there swollen with pride as he looked at my vagina. I even hitched up my dress again, this time as far as I could, so he could see it better, and after a few seconds, he looked up at me with a longing I hadn’t seen in a man’s eyes for years.

I was thankful he didn’t say anything about my pussy leakage, and as he raised my panties up my shins and past my knees, he peered up at me quickly and then pulled my panties back into place over my hips. Reaching up, he gently pulled the material of my dress from my clutching hands, and then carefully smoothed my dress back into place.

He sat on the bed and reached for my hand. “Come on,” Jay said softly as he pulled on my hand, “have a seat and let’s talk some more.”

I sat down next to him and foolishly straightened my dress across my legs, probably out of sheer feminine habit. It seemed ridiculous once I thought about it, especially given the fact that he’d seen me naked two times now – well, naked below the waist, I mean. When I looked up at him, he had a patient smile on his face and seemed content to wait for me to finish fidgeting before he said anything more. I blushed a little as he looked at me, then he finally spoke.

“I want to talk a little bit about what’s going to happen tonight, but, I don’t want to say too much because it will be better for you if it’s a surprise.” He began.

I nodded my head and he continued, saying, “Sally, this evening has been planned with the intricacy of a covert military operation. Nothing has been left to chance, and each and every moment has been choreographed with pin point precision. I don’t want you to be distracted with anything except what you’re feeling, and being pleasured by what’s happening to you.”

“Next,” he said, as he took a breath, “tonight is all for you. Everything that’s going to happen is designed with you in mind. I will always be within arms reach of you and anytime you want me, all you have to do is raise your hand and I’ll immediately be there to see what you need. If at anytime you want something to stop, just say the word ‘Stop’ and it will. And for that matter, if at anytime you want everything to end and the night to be over, all you have to do is say ‘No More’. I promise you no one is going to make you do something you don’t want to do, so use those words as necessary, and remember, I’ll be by your side the whole time.”

I know his words were meant to put me at ease and make me feel safe, but they did little to ease my mind. I was starting to tremble with the fear something horrific was going to happen to me tonight. Jay saw the apprehension in my expression and he squeezed my hand. “Don’t worry, Sally.” He said. “I assure you this will be an evening you’ll remember fondly the rest of your life, and I’m sure you’ll thank me when it’s over. But, it’s important that you go into this evening willing to trust me and willing to do what you’re told. If you’re able to do that, you’ll get to experience something that will be a once in a lifetime event.”

“You okay so far?” Jay asked.

I nodded my head up and down. “So far.” I said, almost whispering.

“That’s my girl.” Jay replied.

“Now,” he continued, “what we’re doing tonight is a role play. It will last about seventy minutes; maybe eighty at the absolute most. As I said, I don’t want to give too much away, but the jest of it is that I’m going to be playing the part of your teacher, Mr. R. You’re playing the part of my young, female student who’s been a very naughty girl, and you’ve agreed to be disciplined by me instead having your parents notified of your atrocious behavior.”

“Are you going to spank me, or something?” I urgently interrupted.

“Let me get to that in a minute.” Jay answered quickly. Then, he continued with his explanation, saying, “There will other people here, Sally. They each have a role to play and a script they will be following. They will do no more, and no less than what their script calls for. I’ve personally met, and checked out each and every one that will be here, and I’m completely satisfied with them.”

“Okay, now to your question.” He said after taking a breath. “This will all take place down in the play room. I’ve placed a paddle down there which could be used on your exquisite posterior under certain circumstances. For example, if you’re asked to do something, and you don’t hold your hand up, or you don’t say ‘Stop’ and you don’t do it, then the paddle will be used – by me only. So,” he added, as he looked me right in the eyes, “you have the power to keep yourself from being paddled. If you really don’t want to do something, raise your hand or simply say ‘Stop’. On the flip side, if you feel like you want to be paddled, all you have to do is disobey without raising your hand or saying ‘Stop’ and I’ll take that as a signal you wish to be paddled. I’ll leave those decisions strictly to you.”

“How many other people will be here?” I asked.

“If they all show up, it should be eleven people. Twelve counting me.” Jay answered, then added, “Sally, each of these people have a role to play, just like you and I do. Once we start, you will address me respectfully as Mister R, or Mister Richardson. You will treat everyone here with respect, too, and you will address everyone else as Sir or Maam. I promise you have nothing to fear from anyone - no one is going to hurt you, and you’ll be perfectly safe. Just remember the rules and you’ll experience something tonight you’ll treasure forever. Like I said,” he chuckled, “when this is over, you’ll thank me.”

Jay sat there for a minute watching me while everything sunk in. “These people,” I said, “these eleven people that are coming, what are they going to be doing? Can you tell me that?” I asked.

“I don’t want to answer that directly.” He said, shrugging his shoulders. “It would give too much of it away, but, they’ll all have contact with you, Sally. What I mean is,” he added after thinking for a second, “they’ll all have sexual contact with you in one way or another.”

Well, finally, there it was.

I don’t know if I was happy to hear that, or sad. While he was telling me all of this, I was frantically trying to put it together in my head….. trying to figure out what he was planning, what was going to happen to me tonight. My mind recalled the stack of towels in the huge bathroom downstairs, and now I could guess why they were there – for his guests to take showers.

“Jay,” I asked, meekly, “are you saying these eleven people going to have sex with me?”

“You’re going to have some kind of sexual interaction with all the guests, Sally, even the women.” He answered. “But, it’s very well orchestrated, and, if you can be brave enough to trust me, I promise you’ll have the time of your life.”

“There’s going to be other women here?” I asked, as an agonizing feeling swept through my stomach. I guess it wouldn’t be so bad if it was all men, but, having other women here while this happens - I’m not sure I was okay with that. What would they think of me?

“Yes.” He said. “Don’t get yourself worked up about it, Sally. They have a specific role to play, just like everyone else.”

“Can I make a request?” I asked.

“Absolutely!” Jay exclaimed.

“I don’t want to kiss anyone.” I replied. “I don’t want anyone to kiss me, either. Okay?”

“Not even me?” Jay asked, laughing.

“I mean except you,” I said quickly, smiling at him. “I don’t want anyone else to kiss me, though.”

“No problem.” Jay said, giggling to me. “That’s already in the rules. No one is going to try to kiss you. I promise.”

“But you can.” I answered. “I won’t mind that at all, Jay.”

He squeezed my hand and laughed. “Thank you,” he said grinning at me, “I’ll try to remember that.”

“Just a few more things.” Jay said, glancing down at his watch. “When it’s over, I’ll bring you back to this room, and I’ll stay with you and everyone else will leave. I’ll draw a bath for you in the large bath tub in my bathroom, and I’ll let you relax and soak while I make you the most fabulous dinner you’ve ever seen. I’ll come back and wash you up, dry you off and we’ll enjoy a nice dinner together. How’s all that sound to you?”

The sun was almost gone – just a thin slice of it remained in the late afternoon. And as I stared through the window at the deepening shadows, I looked up at him and asked, “When does all this start?”

“My guests should start to arrive in about an hour, Sally.” He answered. “Hopefully, we’ll get started no later than 7:45 and be done by nine o’clock.”

“So,” I asked timidly, looking down at my feet and feeling my palms get moist, “Is there any, uh, you know….. anal sex involved?”

I raised my eyes and looked over at Jay. He nodded his head. “Yes, I’m afraid so.” He replied softly as he rubbed my hand lovingly. “It will come at the very end of the evening, and it will be me.”

I felt relieved to hear that. If anyone was going to take my ass, I’d want it to be him. I know he’d be gentle with me, and it seemed fitting that the teacher would have the final ‘say’, if you will.

“Alright.” I said. “But Jay…… uh….. will you, uh…..”

“Sally,” he said, lifting my hand and kissing it again like he did out in the hallway, “I’ll be incredibly gentle, and you’ll be specially prepared before I do it.” Then, leaning over to kiss my cheek, he smiled and tapped my nose with his finger, saying, “Just trust me and everything will be fine.”

“No, that’s not what I meant.” I said to Jay. “I know you’ll be gentle, and I trust you immensely. But, that’s not what I was asking.”

He looked at me for a moment and I took a breath and swallowed before I spoke. “Will we….. I mean, you and me….. will we have regular sex tonight?”

“Yes, my sweet.” He said, with an understanding smile. “I have something special planned just for us after everyone leaves.”

I took a moment to take it all in. I knew what ever happened tonight was going to be different, and that Jay was going to make it memorable and special for me. I felt so safe with him, so cared for, and, so loved. Someone just doesn’t do things like this – go to all the trouble and the expense of something like this unless they are a special kind of person. And Jay was, I knew it. I felt my heart begin to beat inside my chest knowing we were going to have sex together – Jay and I, and that was something I was praying for since the day we went shopping for panties and I felt his rigid cock in my hand.

Ever since that day, I’ve had an irresistible urge feel his hard cock inside me. I’d thought of nothing but him and I was gratified to hear he was going to have me. I wanted to make it good for him, too – so good….. the best he ever had, and give him a night to remember, too. And as I sat there reflecting on everything he’d said about what was happening to me tonight, I promised myself I wouldn’t leave this house until I knew his balls were drained, and emptied out inside my body.

“So,” he said, “are you still game?” Then he added, “If you’re hesitant to go through with this, it’s better to back out now – before everyone gets here.”

I know Jay was being polite and considerate by asking me if I wanted to go through with it. But, did he really think I was going to change my mind now? Over the last several weeks, Jay and I had become so intimate and so close – we’d shared everything. I knew every one of his turn-ons, and he knew mine, as sick and twisted as they were – Jay knew my fantasies. So, did he really think I was going to back out of a chance to let him grant those fantasies and realize my deepest desires?

A hundred wild horses couldn’t pull me out of there. And even though he didn’t really tell me enough for me to know what was going to happen, the things he did tell me touched me in a way that made me have to stay - especially after hearing he had something special planned just for the two of us, and that was so important to me.

“I’m yours, Sir.” I said, proudly - looking up at him and smiling. Then in my best little girl voice I said, “I know I’ve been bad, Mr. Richardson, please don’t tell my parents. You can do whatever you want to me, but, please don’t tell my parents.”

He laughed at what I said, and then all of a sudden, he got this somber look on his face. After a few seconds, he looked at me and started to say something – and then he stopped. Finally after he got his words together, he squinted his eyes and began to speak.

“You know why I asked you to get the wax job, don’t you?” He asked, almost whispering to me. “Instead of just shaving yourself, I mean?”

It was a question we both knew the answer to. I’d already told him all about my nasty, school girl fantasies, including the part I was incredibly ashamed of. And, once I heard that I’d be pretending to be a school girl tonight, I instantly understood why he told me to get a complete wax job. It made sense – it matched my fantasy to a tee.

We looked at each other for a second, and in that time I realized Jay really had thought about every facet of the role play, even down to the appearance of my pussy.

My face blushed and I nodded my head. “Yeah, I know.” I answered.

Jay had a sly grin on his face as he leaned over to hug me. “Sally,” he said, “You know, if I were just….. uh… thirty years younger…..”

We both laughed and he reached around behind him to look through my overnight bag again. Seeing my panties in the plastic bag – the ones he told me to bring to him after my masturbation session the other night, he picked them up and opened the bag. Then, holding them up to his nose, he inhaled deeply. “Ah…..” he sighed. “These are for me….. my private souvenir…… along with the ones you have on now, Sally. I want something intimate of yours to keep; something to remind me of you.”

I blushed thinking about Jay jerking his cock and sniffing my panties, Perhaps even sucking my cunt juice from the crotch as he stroked his cock, thinking about me. Oh, how I wanted him to desire me…. to desire my cunt….. to want me in a way he’s never wanted another woman.

“Well, okay then.” Jay said sharply as he stood up. “We have to get on the ball if we’re going to stay on our schedule.” Then he paused for a minute and added, “I’m sad to say we have one more piece of difficult business to attend to, my dear.”

“What’s that?” I asked.

“It’s for your own comfort, Sally.” He replied. “I promise it is. And, it’s probably going to be a little uncomfortable for you. I’ll do everything I can to make it bearable, though.”

He made his way to the chest of drawers across from us. When he got there, he turned to me and said, “If you followed the diet instructions I gave you, this should be quick and simple. And again, you might not think so now, but later you’ll be happy you did this.”

I watched as he reached into the drawer and pulled out two thick towels and a small, green and white box. My eyes opened wide as I read the large words on the box: ‘Cleansing Enema’. I’m sure he could see the anxieties in my face when I realized what he was about to propose, and before I could say anything, he spoke.

“Sally, hear me out on this.” Jay said, firmly. “You’re going to be in front of people in an hour and I guarantee there’s going to be fingers pushed up your bottom. Plus, you’re going to have anal sex. I won’t force you to take the enema, but, I’m betting you’d rather be emptied out and clean back there before all this starts.” He added. “Think about the alternative for a minute, would you?”

“You can always decide against it,” he added, “but, it would be unbearably humiliating to find any ‘surprises’ in there when you’re being fingered and when I enter you back there.”

As he spoke, I got this vision of someone putting their finger in me and pulling it out in horror. I knew he was right. I knew we had to do it. It was hard to accept, though. And yes, it would be better to take care of that now, rather than risk this kind of humiliation later in front of people.

I nodded my head, accepting my fate and snickering to him in a sarcastic way. “Okay.” I answered.

He laughed at my funny face and told me it would only take a few minutes. “It won’t be so bad.” He said. “We can do it right here on the bed - it’s quick and easy, and I’ll let you have your privacy in the bathroom, Sally. Just go ahead and slip all your clothes off for me.”

To be continued