Teaching the Boss A Lesson (open for two more DEDICATED players)

[slippedhalo]

Gillian almost held her breath as she felt the eyes of the two men roaming over her. She nearly forgot to answer untilt he second 'good morning' and then hastily replied, "Good morning...Masters." But, her focus was changed now as she felt hands roaming up her legs, testing the bonds on the ankles, and then roaming up her body, taking a moment to fondle her breasts possessively, then to her right wrist...and her left...she nearly gasped as she felt fingers slip through the loose rope around her left wrist. Ohgod, it must have been so obvious! she worried.

"What's this Gillian? Has the little bitch been naughty in the night and loosened her restraints?"

Gillian was too terrified of retribution to find her voice in order to asnwer anything. She wasn't certain he wanted one from her at that moment and she just froze in fear. When Gillian gave no response, he continued

"She has, even though she knows it is against the rules." ..."The bitch knows she will have to be punished for this, doesn't she."

Gillian struggled to think of an appropriate answer. She really didn't want to be punished but feared that saying so would only make them angry and maybe torture her worse. She said nothing and the silence seemed to anger him in a different way, he leaned in and said in a firm, deepening voice, "doesn't SHE?"

Gillian, realized she must give some reply so she carefully nodded and whispered "Yes, Master."

Standing back upright, he continued in a firmer, angrier tone of voice, "And, she WILL be punished. But Master will decide when, how and where. First, all the restraints will be tightened."

Gillian felt tears welling up in her eyes again and began to sob as the restraints were now so tight she felt the bonds cutting into her flesh at even the slightest movement. "Master, it hurts." she whispered sadly.

 

[JazzMan2900]

Sean smiled cruelly as Gillian whimpered at the tightening of her restraints. He leaned down to her again, this time letting his hands roughly fondle her breasts as he addressed her. Moving his hands to wipe the tears from under her blindfold, he heard her whisper "Master, it hurts."

"Yes, Gillian, it does hurt. But Master must punish you if you break the rules. My little bitch must learn that she must not break the rules. So the restraints will remain tight. And Gillian, this is just the first stage of your punishment."

Sean decided that this was the perfect time for Gillian to discover that pain could also become pleasure. He reattached the nipple clamps, tightening them until Gillian's breath drew in sharply. Unable to move, however, she was unable to do anything but whimper. Sean reached up and slapped her hard across the face. "Bitch, you will be silent and accept your punishment!" Gillian continued with a small whimper until Sean slapped her again.

"Gillian, you may speak only to answer my questions. Did you do something wrong?"

She said softly, tears still flowing, "yes master"

"Do you deserve your punishment?"

Even softer she replied "yes master"

"Good. Now the punishment will continue"

He reached down, gently moving closer and closer to her sex. Running his hand along Gillian's thigh, Sean could see that despite the pain her body still responded as moisture began to form. Sean placed his finger gently on top of her, just millimeters away from her clit and the opening to her pussy. He was so close she could barely feel him, yet too far away to actually stimulate her. He held his finger motionless, watching Gillian's face intently. Sean knew that eventually her animal desires would play havoc with her brain, begging her to move despite the pain and grind her clit and pussy onto his finger. It would likely take time, first for Gillian to realize what she wanted, then act on it, but Sean's finger was teasing her in a way she had never been teased before. She would break. And when she did Sean would administer the final stage of the punishment.

 

[slippedhalo]

Pain.
Pain in every extremity, every time she moved, and the nipple clamps so tight she worried she'd lose her nipples entirely as a result. The slaps were not even painful in comparison, only shocked her into submission again...and then...then he began to touch her...close, so close...but never close enough to her pussy to do anything, really, nothing painful, nothing stimulating....and with all the other pain in her body Gillian began to feel the crazy compulsion to have pleasure somewhere...any kind of pleasure would hopefully help her to feel less pain.
The thoughts in her head made no sense and were frantic, she felt like an animal...yet it seemed so simple, just a little pleasure, just a little, to lessen the pain...Would it work?
He teased her with his fingers, never quite touching her in the places she needed it most...she groaned in frustration and felt another slap as punishment...slowly...it felt like hours had gone by and slowly, she moved her hips, despite the pain searing her ankles, she ground her pussy against the waiting fingers, just enough so that he brushed up against her swollen nub. Her clit, crying out for stimulation...with a sigh she then rocked back again...It was good.
She had to try again. His had was still just out of reach...she began to move against him, crying out in pain and sighing in pleasure alternately as one motion towards the hand brought pain, then the touch, instant pleasure, then the motion away, the absence of enough to tide her over and she would begin again...she rocked against him like this, over and over, building up speed, faster and faster, breaking into a sweat from her efforts...soon...the pain and the pleasure began to intermingle, becoming one and the same as she neared an orgasm...

 

[macmillian]

Teaching the Boss A Lesson

After helping Sean tighten the restraints, I stood back and let him do his thing. I watched the attachment of the nipple clamps againg and his tightening on her sweet flesh. His teasing of her with his fingers seemed to bring her much discomfort in the begining, seemed to change to something else.

Gillian streched and thrusted her hips out toward Sean's fingers, so close and yet so far. I finished my cup of coffee.

 

[slippedhalo]

Gillian was confused by these strange emotions welling inside her and only once she began to shiver with her release against the stranger's hand did she realize what had just happened and feel true shame, she could feel the heat of her skin as she knew she was blushing from top to bottom, totally embarrassed that someone could make her behave in such a way. She was glad now for the blindfold, she couldn't bare looking the stranger in the eye after what had just happened. She took solace in her eyes at least being hidden, allowing her face some semblance of privacy in her deep shame.

 

[JazzMan2900]

Sean watched dispassionately as his plan began to work. What began as whimpers against the pain turned into gradual wiggling, then finally Gillian moved her entire body against his finger. He left it unmoving, allowing Gillian to rub her clit on his finger and experience the resulting pleasure. Sean knew that deep in her mind she would be desperate for release, amazed that the pleasure outweighed the pain. Soon she would give way to her true animal desires.

Unsurprisingly, Sean was proven right. Gillian became desperate for contact, and soon began to buck against his hand, fighting the pain for the right to experience the pleasure his fingers afforded. He refused to move his fingers closer as she moved against them faster and faster, ignoring the pain each time as his fingers rubbed against her clit. As the speed increased Gillian moved closer and closer, finally orgasming as she thrust her hips against his hand.

As Gillian came down from her orgasm Sean could see that her brain kicked back in and began to wonder what on earth had happened. She turned red, blushing deeply as she realized what she had done. Sean was excited that she had responded so well to the punishment.

"Gillian, you will answer my questions now. How did you feel about that punishment? Did you enjoy your punishment?"

 

[slippedhalo]

Gillian realized it was pointless to lie after what they had just witnessed. "I...think so, Master." she answered, her voice shakey and tentative, something she wasn't used to hearing in herself.

Her limbs and joints, especially her ankles were throbbing, sore. She thought she could feel blood on her ankles from her efforts in straining against the tight bonds. She hadn't felt how much this hurt, the ropes cutting into her flesh, before. Before, she had only had her mind on the pleasure happening between her legs but now...Gillian lay completely still and even then the fire o fthe rope's burned into her exposed, raw flesh. She began to cry from the pain.

 

[macmillian]

Teaching the Boss A Lesson

I silently sat and watched as Sean played out his little scenario with Gillian. It was amazing to watch as Gillian drove herself harder and harder against Sean's fingers. Gillian's climb to her climax and her collapse as she realized what had happened.Now was the time to inflict more humiliation on Gillian while she was so vulnerable.

"I think it's about time we continued," I stated, "you go and get the bedpan and towels and I'll get the basin of hot water and the special items." Sean nodded and we both walked away to retreive the required items. I went to the sink at the far end of the basement and ran the tap until there was hot water and I filled the basin about half way. Returning to the bedside, I pulled a table over closer to the bed and set out the items for easy use. Sean returned with the bedpan and towels.

"Gillian, I have a question to ask you and I need a precise answer!"

Both Sean and I chucked out loud, adding to her heightened anxiety.

"Gillian, Do you have to go to the bathroom?"

 

[slippedhalo]

She thought about this and then replied, "No, Master. I don't." It was the truth.

 

[macmillian]

Teaching the Boss A Lesson

With Gillian's answer, we passed a towel under her buttocks and then slid the cold steel bedpan underneath her as well. Gillian's entire body shivered from the cold and probably the unknown too. Se had replied she didn't have to use the bathroom and here we place a bedpan underneath her. Gillian was slightly raised around her abdoman, exposing her completly.

I wet a washcloth in the basin of hot water and gently laid it on her pubic area and at the touch, I could see you tense up again. I washed the entire area and the poured warm water over the area and it ran into the bedpan. I dropped the washcloth into the basin and picked up a can of shaving cream.

I put a hefty amout of the shaving cream unto my fingers and then spread it out over her pubic hair and the entire area between her legs.

"Now she will be completly naked", as I began to draw the saftey razor across her skin. "Don't move Gillian, I wouidn't want to cut you in such a delicate area!" It took us longer than I thought to shave her completely but the results were well worth every minute. She was now completly exposed and her naked pussy looked even better. I took the washcloth again and washed off the entire shaved area and removed any excess shaving cream. I did this several times, the last time with just my bare hand.

"Partner, Do we put aftershave on a pussy after you shave it bare. The alcohol would probably sting quite bad. hmmmmmmmmmmmmm."

I picked up a bottle of KY Personal Lubricant and heating oil and lavishly spread it over the shaved area and even to put some inside of her. One, then two and then three fingers worked there way into her sweet pussy. Slowly I worked my fingers in and out of her and making sure to hit her clit on passing.

"Well Gillian, how do you like your new feel? You are now completly naked for us."

 

[slippedhalo]

Gillian shivered again at the after effect of feeling so smooth and exposed and also of the warming gel fingered into her. "I...will get used to it, I guess... Master." she answered. Sometimes they asked her things she didn't really think required an answer yet she felt compelled to say something lest she get slapped.

 

[macmillian]

Teaching the Boss A Lesson

"Very good, Gillian, I am glad to see you ar cooperating with us." I said this as I continued to finger her now very moist pussy.

I called to my partner, "Why don't you give her nipple clamps a turn and tighten them down. They look a little loose to me."

"Gillian, since the bedpan is in place, do you have to relive yourself. I would hate to have you wet the bed. Because then you would have to be punished. This requires an answer from you now!"

 

[slippedhalo]

"They're not loose sir, they're very, very tight. Please leave the nipples for now,Master, please." pleaded Gillian not sure how much her poor nipples could stand. She found it strange that she kept being asked if she had to go to the bathroom. "I don't have to use the bathroom, Master." she answered. "I won't wet the bed if I get a chance to go later in a few hours when I might actually have to."

 

[macmillian]

Teaching the Boss A Lesson

"Well OK then, I'll just remove this ", as I slid the bedpan out from under you. I left the towel in place. "I hope this makes you more comfortable." I slowly ran my hands up and dow your body, stopping at your very special places.

Down your one leg, squeezing the flesh of your calf and then up the other side. A few fingers moving into your pussy and to slowly pump in and out. Then up across your belly to the bottom slope of your breasts. I squeeze the pliant flesh, pushing them closer together and shaking them a bit.

Then down to your shoulders and up your arms and back again. lightly up you neck and my finger tracing along your chin. my hand grabing your cheeks with thumb and fingers, forcing your lips out. I let you go as fast as I had grabbed you. I watched your body talk to me with every movement I made. You were still responding to physical stimulation.

"Gillian, we are alone, just you and me. My partner had to leave for a little while. So now it is just you and me..........(a long pause, saying and doing nothing)..........

"BOOOO!" I shout, making you jump and pulling at your bonds as you take in a deep breath." Laughing, "WOW, did you ever jump. Gottcha ya!"

"Well OK, now where were we. ..... Oh that's right, Your loose nipple clamps!" I take one breast at a time and check and check each nipple clamp. "Your right Gillian, they aren't that loose. But you know somethig, I am going to give each one a turn tighter. Really pop those nipples out!

I am standing on your right side and I take your right breast in both hands and I squeeze and lift. My one hand then moves to the clamp and slightly moves it around.

 

[slippedhalo]

It seemed every time Gillian began to adjust to the pain inflicted upon her they would add more to her burden. Now, the nipple clamps were being turned. The right one first. She wimpered at little, unable to stop herself as the clamp tightened and the pain increased. "It hurts so much, master, please, no more." she begged. The voices still sounded familiar to her and she began to analyze a littel each time someone talked. She began thinking it was someone she had once worked with, but who? All of her employees and coworkers hated her, this was true but who could hate her enough to actually kidnap her? She wondered this in silence as she prayed for a respite from pain for a while.

 

[macmillian]

Teaching the Boss A Lesson

Gillian .... "It hurts so much, Master, please, no more."

I heard the pleading in her voice and I paused in tighting the right nipple clamp. I slowly backed it off and removed it from her. I bent down and sucked the nipple into my mouth, swirling my tounge around the sweet tender flesh. I had administered pain and humiliation and now I added pleasure. As I sucked the nipple, I squeezed and massaged the rest of her breast.

After several minutes, I rose up and walked around to the other side of the bed and removed the nipple clamp from her left breast. I sucked on that nipple too as I worked on the rest of the breast. My hand went down to her wide spread legs and returned to fingering your still moist pussy. Slipping two fingers in deep as I could and withdrawing and driving forward again.

"Gillian, how are you feeling now? Would you like me to loosen your bonds? Think about that a minute, yours answers may require you to give up something in return!"

 

[slippedhalo]

Gillian didn't have to think about it. Any offer to lessen her pain meant the world to her at this point. "Yes, master, yes please."

 

[macmillian]

Teaching the Boss A Lesson

"Very well Gillian. I have shown you Faith by removing the nipple clamps. Now you must show me yours." I pause to let her think on what I had just said. All the while my hand kept up a steady rythm, driving my two fingers in and out of your now very wet pussy.

"Gillian, Do you have any ideas on how you can show me that you have faith in me. Let me help you with a suggestion. There is Three ways, only three, that I would consider at this time." I can almost hear her mind as she races to find an answer to my question. I bend down closer to her left breast and I lick the nipple and then watch it harden. I suck it into my mouth and suck here tender flesh.

 

[slippedhalo]

Gillian is reeling from the sensations of his fingers diving into her cunt over and over, making her sopping wet and hot as hell. Three options...it reminded her of a joke her last boyfriend had once said about sex being like a menu with three possible entrees but plenty of starters and side dishes. He meant that there were really only three holes on a female body worth using for sexual pleasure but how one did it was what changed the experience a little...three holes...that must be what her captor was talking about. She hated it in the ass, she knew this. But, if she begged him not to fuck her ass he just might use it against her and do it anyways out of spite. She needed to choose one. "Master....are you speaking of three ways meaning...three holes?" she asked tentatively. She didn't want to make an offer if she was wrong entirely.

 

[macmillian]

Teaching the Boss A Lesson

My hand stopped moving and I withdrew it from her sloppy hole. I had also released the breast that I was sucking and stood up.

"Gillian, no one ever said you were stupid, just a arrgorant and selfish bitch. Yes you are correct, I am refering to your three holes! You sound a little timid when you asked. Is there one that you don't like! Gillian, you "BITCH" Think, consider your answer carefully!"

As I spoke, I walked around the bed, observing you from different angles. I was hoping she would ask to be used vaginally, but I really wanted her to suck my cock. There was more to come, a lot more to look forward to. Today was the start of her new life.

 

[slippedhalo]

Gillian decided it was no use, "Um, yes, Master. There is one I don't like...you didn't ask that so that you could use that one, did you?" she asked, feeling herself slipping into peevish tones she'd never heard her voice use before in her life? Where had her backbone gone? She was ashamed that she was so easily afraid of these men and too easily manipulated to their will.

 

[macmillian]

Teaching the Boss A Lesson

"Gillian, your instinct's haven't left you. But, no that's not why. I will let you make the choice between two and this way you don't have to say which one you don't like." I smiled knowing she couldn't see me and I sensed that her defenses were starting to show the strain. Now to get a little mean and rough to show her that I wasn't wavering.

"OK Bitch, Time to choose........." I through the words at her. I knew they must have felt like geting slapped or cold water thrown in your face. "I want to know if you want to do it Anally, up your ass, or Orally and you keep what I give you. Now choose, show me your faith. I stopped the pain and I can start it all over again."

 

[slippedhalo]

Gillian grimaced, really not liking either option much but knowing with absolution that she hated one and only mildly disliked the details of the other (depending on the guy). "Ok, ok, Master...I choose oral." she said quickly, not wanting him to change his mind and revoke the opportunity for choice.

 

[macmillian]

Teaching the Boss A Lesson

When I had finished talking, there was a slight pause as you thought about the question and the answer.

Gillian .... "OK, ok, Master ... I choose oral."

"Very well Gillian. Oral it shall be. You know the rules Gillian. All the way or until I say stop. I hope you understand the consequences if you fail to please me." I went to the bottom of the bed and proceeded to untie her ankles.

"Flex your legs a little Gillian, this will give you a little more flexability."

 

[slippedhalo]

Gillian did as he said, relieved to have her leg unbound. She wriggled her fingers to remind her master she might need her hands free too.