Sweet November Ch. 13

Despite my earlier climax only having passed only a few minutes earlier, I found myself once again on the brink. I began to thrust in and out with ever-increasing speed and force as I grabbed her magnificent ass for leverage until we both cried out in simultaneous orgasm and I collapsed on top of her.

Gretchen allowed me a few long gasps to catch my breath and then pushed me back on to the floor like a rag doll. Then she sat up and called to her man, "Call Rose on the intercom and tell her to come here; then get your ass over here and lick my pussy clean."

Motivated by lust and a longing to keep his wife happy, he quickly obeyed. In mere seconds I watched as he vigorously cleaned her tidy little snatch of any evidence of my presence. She lay there almost motionless as though he was not there.

Moments later the door opened and Rose stood in our presence once again.

"Rose, take him to the second guest room to rest briefly. Then grab him something to drink." Gretchen said all of this without moving so much as an inch from where she lay.

"And Slave," she called, as I stood to follow Rose out the door, "don't get too comfortable. You still owe me."

I nodded my understanding, "Yes, Mistress," and then followed Rose down the hallway a few doors to a guest room where she gave me a tall glass of water and a wanton stare.

I took a long drink from the glass and then fell down on the soft bed before me. I had only intended to close my eyes for a few seconds but I must have fallen asleep. I did not even hear the sounds of her entering the room; however I most definitely felt the sting of her riding crop on my naked bottom when she determined my nap was over.

"Stand up, Slave," she ordered, as the second sting pummeled my right cheek faster and harder than the first had hit the left.

I wasted no time and stood before her as quickly as possible with my hands folded behind my back in submission.

"Did you have a nice nap, slave?" she inquired, as she tapped the underside of my cock and balls with her crop.

"Yes, Mistress," I replied, as I kept my eyes down.

"Good; too bad for you that is the most rest you will see for a while," Gretchen teased, as she continued to tap the bottom side of my genitals. As every second passed she picked up the pace and force until the gentle tapping had turned to aggressive slapping. My cock had sprung to life and seemed to grow even harder the closer she got to the head and the more powerful the blows. Conversely, my balls were quaking and I found it tough to stand still when the tip of her rod found the softness of my scrotum. I was in near agony when she finally stopped, but my cock was about as hard as could be.

"Follow me," Gretchen said with a smirk, and turned and walked out the door.

I had a tough time keeping up with her long strides as she strode quickly down the hall. My balls ached with every step I took as they slapped against my legs. Then I looked and saw her disappear through a door and hurried to catch up. Once inside, I found her already positioned on all fours on a medium-sized leather-cushioned ottoman. Her other man-slave was already in the room and had found his place behind her. His cock was poised and ready to penetrate her waiting pussy.

I was surprised to see it was nearly seven inches long with girth comparable to mine. From the comments she made to me and the teasing she inflicted on him earlier, I expected quite a bit less.

As he slid his rod inside her she gasped slightly and motioned for me to stand in front of her. Once in front of her she took my member in her mouth and slowly sucked it in and out. Her eyes gazed hungrily up at me as she took every stroke her hubby drove into her and the vigor with which she sucked increased. Occasionally she would stop sucking to lick and kiss my balls. This felt absolutely glorious after the beating they received earlier.

After several minutes she pushed me back and kicked her slave behind her. Once out of her way she flipped over onto her back and summoned us back. With her legs pulled over his shoulders he rammed his cock deep into her with every thrust. As hungrily as she sucked my cock before it was nothing like the way she was going at it now. I took her amazing tits in my hands and began to roll her nipples between my fingers. She reached back and took my ass in her hands and dug her nails deep into my skin as she pulled my cock in further.

That was all it took. I blew my load hard and fast down her throat. As if on cue, my counterpart began to empty himself into her pussy as well. As she swallowed hard to keep up, her body began to quiver as her apparent orgasm took over. Lucky for her, this was at least the fourth since he started fucking her, but easily the most powerful.

As our climaxes came to an end she once again pushed us away and took a seated position on the ottoman. She grabbed my arm and pulled me towards her, then grabbed the back of my head and kissed my passionately. As our tongues danced, the taste of my own cum filled my mouth and arousal and disgust fought within my mind.

We were locked in the kiss for several minutes before she finally released me. I fell to the floor catching my breath from all that had occurred and realized we had been left alone in the room. I did not know if he had left on his own or if she had motioned him to go during our embrace. The next thing I realized was that lights that had not previously been on in the room now were. This brought a myriad of bondage equipment to my attention that previously I had not seen.

Noticing the look on my face as I took in the various objects scattered around the room she stood to her feet and sought to gauge my anxiety. "Scared?" she questioned, with an evil slant to her tone.

"A little," I responded tentatively.

"We'll change that," she followed, and motioned me to rise once more.

She retrieved a leash from a hidden compartment under the cushion of the ottoman and hooked it to the collar still around my neck and began to lead me toward the far corner of the room. "You know," Gretchen said, "I did not give you permission to come in my mouth."

"I'm sorry, Mistress," I apologized.

"Although I enjoyed it thoroughly, you must be punished for such behavior," she announced.

"Yes, Mistress," I acknowledged, as she stopped in front of a set of stocks and opened them up. Then she pulled the leash through the hole where my head was to go and positioned both hands in place as well. Finally she unhooked the leash and then pulled the top half of the stocks down into place and locked it.

I watched as she approached a trunk against the back wall, opened it, and began to rummage around. Finally she pulled out a long wooden paddle like I had seen in so many frat party movies. Then she sauntered towards me in her sexy silver body suit with her nipples as pert as I had ever seen. It was obvious she was very turned on by the idea of punishing me. As she disappeared out of sight I felt her hand rub down my torso and begin to caress my ass. Then suddenly she pulled her hand away.

Time froze as I waited for the impending smack of the paddle on my ass. I could feel my heart pounding as the intensity of the moment weighed heavy on me. I began to sweat and soon felt a cool bead trickle down the crack of my ass causing me to shiver.

SMACK!

The first swat landed across both cheeks hard enough to push my shoulders hard into the stocks.

SMACK!

Another landed with equal force to the first.

SMACK!

A gulp escaped my lips and she commanded my silence.

SMACK!

I Bit down on my lip trying to contain my pain.

Time froze again and I calmly tried to catch my breath. My bottom burned; I had never felt strikes so hard in my life. Right now I was grateful she had not used some of the objects I had had used on me by smaller women.

I still had not seen her come back from behind me, but after several minutes of heavy breathing I figured she must have left the room, and I relaxed my weight so that I was no longer standing on the balls of my feet.

SMACK!

I did not think it was possible, but either the shock of not knowing or the power of her swing made her last swing the most painful.

Finally she stepped up from behind me with a satisfied grin on her lips and lust in her eyes. She dropped the paddle back into the trunk and reached inside again. I prayed she did not grab anything worse than she had already used.

My prayer was answered. She closed the lid to the trunk and sat down on the lid with her back against the wall and her legs spread wide. Then she revealed the prize she had pulled from the trunk: a large white vibrator.

"Watching your ass turn so red and feeling the heat after every swat really had an effect on me," she teased, as she switched on her toy and ran it across her clit.

I watched with desire as she brought herself to one orgasm after another over the next half-an-hour or so. If I had wanted to, I could not take my eyes off of her as she shoved it in and out of her pussy, licked it clean and then, shoved it back in again.

"It's time for you to come again," she announced, after climaxing one final time.

I was so turned on by watching this sexy beauty queen perform for me, it was no surprise I was hard again, but I could not help but wonder how much longer I would be able to keep going.

Once again she disappeared behind me and I could only hear her rattling around. Suddenly she was next to me applying some sort of lube to my member. Then I felt her slide a vaguely familiar tube up the length of my cock and heard a suction sound lock it firmly in place.

"This was my favorite part of the competition." Gretchen told me as she stepped back in front of me. "I loved it so much; I paid extra to borrow one of the devices from Helen."

I looked down and saw the control in her hand and realized where I had felt this before. The first time I felt it I was trying to hold out for as long as possible. I had a feeling this time the challenge would be different. I was right.

"I want you to fill this." She said directing my attention to a very small glass attached to the end of the vacuum tube. "Once you do the machine will stop."

The glass was small, but I could not imagine how she expected me to fill it and perform four more times after that. I could not help but wonder what my punishment would be if I could not come through.

Before I had too much time to worry she turned the machine on low and the machine went to task. At its lowest setting it did a phenomenal job of replicating a sucking and stroking motion, but it was merely a tease. Every few minutes the machine would pick up the pace and a few minutes later it would return to this "teasing" rhythm. Whenever it sped up it would go a little faster than the previous time, but seemed to last just long enough to take me to the brink before finally switching gears and taking me to "teasing level" again.

Gretchen was transfixed by it all and could not get enough. Whether it was watching my desire to come being held in limbo or watching the machine work that held her attention I did not know. Whatever it was, she looked like a kid in a candy shop with a wad of money in his pants and not being quite sure how to spend it all.

The machine once again sped up and I could feel my balls rise as the ensuing orgasm neared. My muscles tensed as the payoff came closer and my load readied for exit. My ass tightened as the pump continued away and the orgasm I longed for seemed imminent. Then...out of nowhere...the machine apparently sensing the outcome, slowed way down and at the same time, locked down hard around my cock. This caused my cock to ooze cum slowly, rather than spurting like I so desperately desired. Instead of the hard, fast climax I needed, my balls were being milked agonizingly slowly.

In desperation, I thrust my hips against the air in futility. I was just trying to make contact with anything in order to release my climax. Gretchen eyes became glassy as a smile seemed to harden on her face. My pain had become her pleasure and she reveled in it.

Time seemed to slow to a grinding halt as the machine continue to squeeze every last drop from my dick not caring whether I really had any left to give. Time ticked on as it continued to pull and tug at my tired member. Finally, after who knows how long, the machine stopped as the cup filled to the top. I was spent.

Gretchen laughed wickedly at my agony and then removed the contraption from my member as it went completely soft in seconds. Next she flicked and pulled on my now tiny member and giggled even more. I was humiliated and yet somehow knew there was more to come.

The sexy woman who I had once desperately wanted to please, had become the mysterious woman I hoped to survive. The look she got when she tortured me was like none I had never seen and I was terrified.

"I think you are going to need some help getting hard after that thing," she teased. "Lucky for you I am going to help."

She stepped to the front of the stocks and lowered them so that I was no longer forced to stand. Now I was able to kneel much more comfortably. What I had not realized was that put my ass in a prime position for her. She soon brought it to my attention when I felt the cool, wet sensation of lube being slathered on my crack and hole, right as she disappeared out of sight. After a generous amount of lube was applied, I felt a cool smooth cylinder being pushed into my ass and wires hanging out of it down to my feet.

Gretchen stood before me one last time with what appeared to be a timer of some sort with screws on the bottom. "This is the key to your next erection," she said, and stepped behind me once again.

I got the feeling from the way she was moving and pulling the wires that the box attached to the cylinder in my ass. I had no idea why.

"See you in an hour," she laughed, as she smacked my ass, turned off the lights, and walked out the door.

There I was, locked in stocks, in the dark, with some mystery device shoved up my ass. What was I to do but wait?

Several minutes passed by and I began to drift off to sleep as mental and physical exhaustion took its toll. I fought it for a short while until I finally allowed myself to relax enough to fall asleep. I do not know how long I was out but it could not have been long when the object in my nether regions came alive.

It was a feeling like I had never felt before. In the past couple weeks I had felt a vibrator in my ass, but this felt a bit different. Instead of simply vibrating it felt more like it was shaking back and forth, causing it to rotate. As it rotated it seemed to be screwing itself further in to me. As it moved deeper and deeper the pain intensified but, strangely, I began to feel a tingling sensation in my balls as my cock began to rise once again. I soon found myself wriggling my hips in order to allow even greater penetration as my erection seemed to get harder and harder in spite of the increasing pain. Suddenly the device stopped but held itself firmly in its new, deeper location.

Once again I found myself alone in the dark wondering what was next. Once again several minutes passed without a noise, a movement, or a flicker of light. Once again I began to drift off to sleep only this time my raging erection made it much more difficult to get comfortable. Finally, being tired conquered being uncomfortable. My cock lost some of its swelling and I drifted off to sleep again.

I was out for even a shorter period this time when the device began to move again. However, this time the object did not shake. Instead it grew. It felt as if it were inflating slowly. I could actually feel my hole being stretched very slowly and very methodically. Again, the pain was excruciating, but again my erection found new levels of excitement. Just as I felt tears welling up in my eyes it stopped.

I gasped long and deep as I settled in for what I could only assume would be another break before the next assault began. This time I could not get comfortable and this time my erection never faltered.

Before long I felt the unit one final time. This time it began to pulse. Now that it had methodically deepened its penetration and then slowly widened my asshole it began to thrust back and forth within me. It started out slow at first and step by step raised its level to go both harder and faster. My balls began to tingle once more and I could not help but cry out to be allowed to come hoping that Gretchen would return any moment and allow me the pleasure of shooting my wad in this humiliating fashion.

She did not come.

With my head and hands locked tightly in place I struggled to find some way to get my much-needed release. The device showed no mercy and continued to pick up the pace. Never had I received such a pounding as second by second it thrust harder and harder into me. In the darkness I felt a hand reach up between my legs and grab my member firmly at the base. That was all the contact I needed and I released my seed into the darkness. As my climax subsided the muscles in my ass relaxed, apparently signaling something in the device, causing it to stop pulsing and return to its original size and shape. I collapsed in a pile of sweat and cum, still held in place by my stocks. The stranger who allowed me to come remained a mystery as they disappeared in the darkness and I lay there for several more minutes. The sound of receding footsteps was the only signal I received that they had left the room.

For a few more minutes I lay in the darkness catching my breath until I heard the door swing open behind me and all the lights were switched on. The bright lights made it nearly impossible for me to see anything as the stress of going from utter darkness to bright light forced me to squint until my eyes adjusted appropriately. While I struggled to see, I felt Gretchen moving around behind me and pulling the mysterious device from my ass.

"I knew you would enjoy that, you slut," she teased, as she threw it in a trunk and then came forward to release my head and hands.

Once I was released, I could not help but rub my sore wrists and neck a little as she motioned me to kneel on the floor in front of her. She attached the leash to my collar once again as my eyes finally regained their sight. Only then did I realize she had gone from wearing an incredibly sexy body suit to wearing her equally sexy birthday suit. If it were not for my previous activities I am sure my penis would have sprung to attention immediately.

"Up," she ordered, as she pulled up on the leash and practically jerked me to my feet. Without another word she stepped quickly towards the door at the front of the room, pulling me aggressively along. I had a tough time keeping up, thanks to my legs having fallen asleep during the ordeal.

After traveling only a dozen-or-so feet down the hallway, we stopped. I have to admit part of me was disappointed when we only went as far as the next room. I was thoroughly enjoying the view of her pert, round ass swaying side-to-side as she sauntered ahead of me.

We walked into a large bathroom that looked like it should be attached to some incredible Master Suite. There was a Jacuzzi-style tub in the corner with unlit candles wrapped around the edges. Two sinks against the wall had extravagant brass knobs and spouts and sat in front of large vanity mirrors with surrounding lights. In the corner opposite the tub was a large glass brick shower with multiple spouts coming from various heights and angles. The shower was easily large enough for half-a-dozen adults to use at the same time very comfortably. The room was also adorned with white flowers and even more candles scattered throughout. It felt very sophisticated, almost snooty.

Gretchen pointed to a beautiful wooden chair with a vanilla-colored cushion and ordered me to retrieve it. I quickly obeyed and brought it back for her to sit.