Cassy's Game Ch. 5

Mistress Lindsay took no crap. Her orders were precise, her manner direct. I went from quiet subservience on the kitchen floor to quietly licking the grime from her street shoes in the living room. The taste was terrible and the grit on my tongue and my teeth made me nauseous.

I took advantage of my actions to survey Mistress Lindsay, about forty years old but still elegantly beautiful. I could tell she had been well taken care of in life, with the kind of demeanor, manner and looks only achieved by the wealthy and well to do. Her hair a fiery red, parted off to one side, framed a lovely pair of full lips, perfect nose and dark green doe eyes. She was slender, or should I say her waist was slender, rising to a full set of luscious breasts that displayed the freckles in her cleavage that were missing in the face of a woman with so light a complexion. Her slim hips were almost boyish and led to her well defined legs. The shoes I was licking were red with three inch heels and very expensive. I could picture her running a board meeting or an estate with an off hand attitude. While I licked, she talked.

"Your silence is commendable slave. I want you to remember to stay silent unless I ask you a direct question. If you speak at any time without being told, you will be punished. I know this must be difficult for you, not knowing who I am or what I'm capable of. Let me tell you now that I am capable of inflicting great pain. Your Mistress told you that this was an evaluation, you are the test subject but the evaluation cuts both ways. Not only will your pain tolerance be tested but the quality of your training also. Mistress Cassandra, though new at this, will be judged by your response here tonight. I hope you don't let her down as I have become very fond of your Mistress and would hate to see you disappoint her."

"Now get on your feet."

I had always been proud of my wife. Her beauty and intelligence were a source of great pride for me. My pride, however twisted, had been challenged and I was determined to demonstrate the value of my Mistress through my actions. I rose to my feet with my chin thrust out and my chest forward. My wrists still restrained behind my back. She rose with me and reached for the tie that still held her wrap-around dress together. Opening her dress to reveal a red silk bustier that cinched her waist, leading to garter straps holding up her black stockings. Her breasts, high and proud, were bare as well as her pussy and ass. As I gazed I saw she was a true redhead, her well trimmed pubic hair a shade darker than the hair on her head. I gazed upon her beauty and recognized the crop in her hand just before it flashed up to hit me in the balls.

"You are never to look directly at me or gaze into my eyes without being told to. This will be infraction number two. For every infraction of the rules you will receive ten lashes from my crop."

Here I was at twenty lashes already and I didn't know what infraction number one was. "What did I do to..."

Another snap of her wrist and the crop fell on my upper thigh. "That is infraction number three. When you didn't greet me in a proper manner, that was infraction number one. All slaves must greet their superiors on their knees and kiss their superiors feet".

She snapped a leash onto my cock cage and pulled me to the bathroom. Leading me to the sink she tied off the leash to one of the decorative handles just beneath the basin. It was somewhat below crotch height and left me in a curiously stooped position. I heard her running the water in the tub behind me and then rummage in the closet, pulling out an enema bag with a long nozzle that ended in a small bulbous head with four holes divided evenly around the perimeter. She squeezed four pumps of the hand soap next to the sink into the bag and turned to fill it at the tub. She hung it from the towel rack next to me, it looked very heavy and quite full, and let the nozzle run until warm soapy water spurted out into the sink in front of me. Without ceremony she shoved the nozzle into my ass with a gasp on my part.

She looked at my face in the mirror above the sink with one elegant eyebrow arched. "Have you ever had an enema before?"

I admitted that I hadn't which brought a smile to her lips. "Your Mistress complained that you're a rather dirty fuck." Her use of profanity startled me. "We'll take care of that, but from now on you're going to have to keep yourself clean for your Mistress. This is a very heavy load for a first time enema, so I will allow you two attempts to take it all. Whatever is left after two tries you will have to drink."

I thought if I was made to drink warm soapy water it would make me sick. I also thought that this woman probably meant every word she said. I was taken aback by the warm, pleasant sensation when she released the enema into my bowels. I had experienced nothing but discomfort and pain from this woman so far aside from her beauty. Then it hit me, I looked at the red rubber bag hanging next to me from the towel rack and judged it to be not quite one quarter empty and already I had a cramp that made my head swivel towards the toilet. I wanted to run for it then but my cock cage was tied to the handle and I couldn't move. I gave a short tug to the leash anyway.

"Do you want me to stop?" She asked me with a lilt to her voice.

I looked at the bag, still emptying it's contents into my bowels and judged the discomfort bearable. "No Mistress Lindsay."

I know it sounds sick and sad when I say that when Mistress stopped the enema I was proud that I had taken more than half the bag. I felt a growing confidence that I was going to make it through this test. My confidence sagged when I saw her reach for her crop and approach me.

"We will start your punishment now slave. You will count every stroke, silently, to yourself. If so much as one drop comes out of your little pussy, I will consider that another infraction and add ten more strokes to the forty you have already earned."

"Forty." I thought to myself, wasn't it thirty. My mind reeled trying to figure out how I was going to correct Mistress Lindsay without having another "infraction" added to my total.

She reached down and quickly removed the nozzle from my anus, making me clench my cheeks together harder for fear of losing a drop of liquid. I sucked in a small gulp of air as the crop lashed my tensed buttocks. The aching in my bowels seemed to increase with the amount of pain Mistress Lindsay dished out. With every muscle in my body tensed to prevent my insistent bowels from letting go, the strokes from her crop seemed to land harder and harder.

"You should know by now that relaxing during a beating makes the punishment easier to take," she taunted me.

Yes I knew that, not that I would have been able to express it so simply but I had always managed to get into the rhythm of a beating and had been able to endure more when I felt resigned to it. Trying to hold in the enema while suffering under her crop was a new and unnerving experience.

"How many was that?" She eyed me expectantly.

"Oh shit." I said to myself. I hadn't been able to keep track of the blows at all. I had actually forgotten to do so and decided to lie. "Seventeen Mistress."

"My poor little thick headed slave thinks he can lie to his Mistress. Consider that another infraction. We'll have to start all over again. Can you handle fifty slave?"

"Yes Mistress."

"We'll see."

She resumed striking my sore ass. Concentrating on the count seemed to lessen the cramping. I reached twenty five, waiting with my eyes screwed shut for the twenty sixth when I realized she had stopped.

"What's the count slave?"

"Twenty five Mistress."

She told me I had done very well and untied the leash from the handle. I stood, stretching my muscles and re-focusing on the need to move my bowels. Mistress gave her consent and I sprinted to the toilet. I couldn't believe how little came out and was at a loss to figure out how to wipe myself with my hands tied behind my back.Mistress solved that problem by making me get in the shower and hosing me down with the cold spray from the detachable shower head. The cold water felt good on my battered ass but soon I was shivering as she again tied me to the handle under the sink. I took the rest of the bag into my rectum and again endured the remainder of my punishment. I could barely rest my weight on the toilet seat with my severely mauled behind. Raw red welts throbbed across my fiery cheeks. I felt as though I had been branded.

Once again I was led into the tub to be rinsed off. Mistress Lindsay then took me to the bedroom and secured my ankles to the bed before releasing my hands and chaining them to the headboard. I had noticed upon entering the room that there were many candles lit in the bedroom. A large candelabra stood in one corner of the room while every surface held a number of lit candles. They weren't there when we came through on our way to the bathroom, and even if they were there, they weren't lit. Mistress had spent all of her time in the bathroom with me so that meant someone else was in the house with us. I assumed Mistress Cassandra had doubled back and it gave me a comforting feeling to know I wasn't all alone in the house with this cruelly sadistic woman.

Mistress Lindsay walked about the room and seemed to be peering into the flame of all the candles, making some kind of judgment I didn't comprehend until later. I felt a surge of joy as she produced a key, the key to my cock cage, and proceeded to unlock the stainless steel shackle around my scrotum. My cock responded, quickly gaining in girth but then hesitating as if the cage were still on. I felt a surge of relief as my cock gained full erection, just happy that I could enjoy the feeling of arousal.

She laughed at my dick, throbbing in the candlelight. "Your Mistress doesn't trust you without your cage does she slave?"

I looked down at my hairless groin and said, "No Mistress, she doesn't".

"Do you know what will happen to you if she ever catches you masturbating again?"

"No Mistress."

"I've given you a small taste of what you will experience the next time you are caught with your little dick in your hand. For the next few hours you will experience much more, more than you have ever imagined. I'm going to have you begging for mercy before we're through. You won't ever feel like jacking off again. If you are caught again, I might just make it so you CAN'T ever masturbate again. Do you understand me slave?"

The next few hours? Oh my god, this can't be happening. What did she mean by CAN'T ever masturbate again? Was I going to be castrated? My eyes must have danced with fright as she smiled down at me, absolutely reading my mind by the expressions that passed across my face. I gulped as the words passed my lips. "Yes Mistress."

She picked up a large, fat, red candle and held it over me, her eyes sparkling in the flickering light. She slowly tipped the candle, I expected a torrent of wax but only a few drops plunged through the air and landed on my belly, making me hiss. She redirected her onslaught upwards and I hissed again as she landed a near miss right next to my nipple. She laughed to herself the more I expressed my pain and was almost laughing diabolically as she hit the bullseye on one nipple then the other, making me writhe on the bed, almost screaming. I didn't know how much more of this I could take. The look of pleasure in Mistress Lindsay's eyes as she looked at the coating of wax on my hairless chest had me scared, more scared than I had ever been. I felt like an object, a plaything for her amusement, utterly helpless against this demon.

"Look slave, look." She was looking at my crotch with a passion and my eyes followed hers. My heart sank as I saw my hard cock throbbing, standing tall and betraying my arousal.

I was about to start crying. The conflicting feelings raged through my brain as I watched her again take another candle from the night stand and hold it over my bouncing cock.

"No, no." My mind yelled as she looked from my cock, to the candle, to my face. She reached down with one finger and wiped the drooling pre-cum from the tip of my dick, holding it out in front of my lips and looking into my eyes. I knew what was expected of me and craned my neck forward, pursing my lips as I sucked the sperm from her finger, like a thirsty man sucking the dew to keep from dying.

"This excites you doesn't it slave? I rarely see a true masochist, one that thrills to every painful touch like you do. I think I'm going to have fun with you."

She held the candle higher and tipped it, hitting me square in the balls and making me scream. The pain from the first droplets barely diminishing before she added to the now white wax. She slowly worked her way upwards, dribbling wax now on the shaft, now on the sensitive tip. I actually screamed as I struggled on the bed, not caring anymore about my silence or my Mistress or my composure. That's when I passed out.

I somewhat recalled being carried through the house and taken down the stairs to the basement. By who I don't know, my fogged brain not making any recognition beyond my being in my own house. I remember as I was being strapped down to a padded bench in the laundry area thinking to myself, "Where did this come from?" but that was the only coherent thought during this time.

I awoke shivering in the darkness, trying to see my surroundings while being doused with cold water. As my senses came alive with the still raw pain in my genitals and my nipples, I understood that I had a blindfold on. Hands caressed my cock and balls, ripping chunks of wax from my crotch and renewing the burning of my wax bath. My cock again betrayed me as it grew in response to my treatment. I heard Mistress Lindsay laugh from behind me as I moaned when a cooling liquid was being applied to my cock and balls. The hands rubbed it in generously and strayed upwards to my ass crack, eventually entering my anus and twisting back and forth. As the finger withdrew I heard a man's voice behind me say, "All clean Mistress". I opened my mouth to speak and felt a shaft of rubber roughly shoved into my mouth. I could feel the shape of the penis gag with my tongue as I felt it being buckled behind my head, the tip pressing against the back of my throat. I had to stretch my neck out to keep it from choking me. With all the pain, the deprivation of my senses, all that had happened up to this point, the only thing I could think of was my embarrassment over another man witnessing my degradation. "Who is this guy?" My mind raced as again I felt hands on my balls.

"Mistress Cassandra says that you have real potential to be a first rate cock sucker. She also says that you love to take it up the ass. Is that true slave?"

I struggled to shake my head no, which brought forth another laugh from Mistress Lindsay. "Again you try to lie to me slave. That's not good for you."

Mistress Lindsay's voice came from far away, somewhere in front of me but I felt a broader smack on my ass than the sharp bite of a crop, it must have been some type of paddle or board. It almost took the wind out of me as it was reapplied to my ass again and again. The force of the blows reminded me of the presence of this other man. He must be the one wielding the paddle.

"Aren't you a cock sucker slave?" I heard Mistress' voice through my pain and started to nod my head up and down, up and down. "That's a good girl." She said as the blows stopped falling. "You like to get fucked in your little girl pussy don't you slave?" I felt the air from the paddle as it was raised to come down on my ass again and shook my head yes even more vigorously than before.

"Show me how you like it Sissy." The use of my "secret" name only added to my confusion. How was I supposed to show her anything while I was trussed across this bench? She couldn't mean that she wanted me to don my girlie clothing as there was no way I was going anywhere. I felt hands spreading my cheeks apart and the cool lubricated tip of a dildo fill my ass crack. From the pressure in my cleft I knew this one must be huge, the tip itself felt like it was the width of a beer can as the pain from insertion welled up, making me moan around the penis gag in my mouth. I felt the lovely pain from her cock wash through me as she or he rested after getting the huge head in. I felt a push and the dildo kept sliding into me, unbelievably far.

"Do you like it Sissy?" Her voice came from behind me and I felt relief that it was her pushing the dildo into my ass and not the man. I nodded my head up and down in spite of the pain. "I don't like the name Sissy, it's so, common. What do you think would be a better name slave?" I couldn't tell her with the penis gag in my throat, so I figured the question was rhetorical. "What's your middle name slave?"

She knew I couldn't tell her but my fear of this woman drove me to try to communicate, "Myphyl" I croaked around my gag.

"What was that slave?"

"My-Phyl" I tried again to tell her as she laughed.

"Oh that's right, it's Michael. Yes I think Michelle would fit you better than plain old ordinary Sissy. Do you like this Michelle?" She resumed stroking with the dildo in my ass.

Honestly the pleasure was overtaking the pain quickly, I was loving the feeling of this gigantic cock in my "pussy". Before I could nod my head in the affirmative she reached down and felt my enlarged cock.

"I think Mistress Cassandra was right, you are a little whore for cock. Let's see how much of one. Release his gag and take off his blindfold."

I realized the last direction was directed at the other male in the basement with us. His presence seemed to drift in and out of my consciousness. Mistress Lindsay could make me remember him or forget him at her will. The gag was unbuckled and the light hurt my eyes as my blindfold was removed. I squinted against the glare as two large hands came down on each side of my head, holding my head firmly as I choked from the removal of the gag.

"Make him hard for you Michelle." The flaccid cock rubbed across my lips, cheeks and nose. It was about five inches long and thick, waging back and forth in front of me. I opened my mouth and took him between my lips, sucking his fleshy cock down to the root. "That's it Michelle baby, make him hard for you."

The cock grew in my mouth, gaining in length and girth as I worked it over with my tongue and lips. What was a comfortable, sensuous feeling as I swallowed him whole turned into quite a task as his member started to hit the back of my throat, making me choke but also producing a thick, creamy saliva that seemed to ease his penetration of my mouth. It felt natural to take him on the in stroke as mistress slid her large cock into me.

I took time to inspect my lover, a giant of a man, rather heavyset but obviously very strong. He wore ankle and wrist restraints and a leather hood with just his eyes showing and a zipper across his mouth. Probably a slave like me I thought, here to help his Mistress with my subjugation.

I had always loved getting good head, and knew just what I wanted when I rarely got it. I just did everything that I would like done to me. Here I was, giving as good as I had ever gotten, laving his cock with relish. I actually enjoyed giving this stranger pleasure as Mistress Lindsay urged me on.

"Oh yeah Michelle, you're doing so well. Come on slut, suck that cock. Make love to his dick baby. Oh you little whore, come on suck that spunk right out of his cock."

My personal cheering section kept up her onslaught of my ass, adding to the pleasure I was receiving and making me lustfully wild. I sucked that cock and derived as much pleasure out of giving head as I had ever gotten.

"When he comes baby, suck on him real hard. Try to get every last drop of his jizz out of his balls. Men love that Michelle, and they'll love you for it."