Cassy's Game Ch. 4

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Two new women enter Jason's life.
3.3k words
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Part 4 of the 5 part series

Updated 10/29/2022
Created 11/08/2001
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wormwood
wormwood
10 Followers

Another day late for work, with the new sensation of my cock cage lumbering under my panties, my hair still plastered down to my head from my session with my Mistress and the feeling of my hairless legs and ass under the silky material of my panties. The strong smell of my wife's feminine moisturizer, making a silent announcement of my new found femininity, certainly made me self conscious of standing close to anyone.

I must say the contradictions of going to my "manly" job after being put in such a "womanly" position at home, left me feeling out of place in my job and in my relations with other males. My boss gave me a stern warning about being late again, saying that he would have to put something in my file and the next infraction would result in a formal, written warning. My apologies would do nothing to help this situation but I gave them anyway, sincerely feeling them necessary.

My hairless cock was a constant reminder to be conscientious and careful about my actions. I didn't want to do anything stupid or get myself injured. I had a vision of myself being administered to by a team of paramedics, laying on the plant floor in my panties with the cock cage exposed. Mine wasn't a particularly dangerous job but the threat of injury was there, I had seen more than one co-worker mangled in the regular course of duties so I knew full attention to my surroundings was required. However practical my caution was, it did tend to slow me down.

I made it home on time though, something I didn't seem to have a problem with. My Mistress was waiting for me with a look of amusement on her face. Before completing my usual homecoming ritual of stripping and donning my cuffs, she instructed, I was to remove the rest of my body hair and shower.

I thought the loss of my pubic hair and leg hair already demeaning. I didn't see much difference in losing my chest and back hair so I submitted meekly. I was stripped and waiting for the shower to warm up when Mistress Cassandra entered holding an electric trimmer.

"Turn off the shower." She instructed.

"But, you don't need those for my chest and back hair." I could have used the trimmer for my thick pubic and leg hair, but my chest hair was thin and sparse, my back hair almost non-existent. I turned off the shower.

"When are you going to learn to stop questioning me? I need it for your head."

"My head? Why my head." I whimpered.

"As a sign of your subservience to me, dummy." She said this with a flat toneless voice. " I think it will look good on you and it is all the rage these days. At least I'm letting you keep your eyebrows."

"Oh god." was all I could say as she maneuvered me to a sitting position facing away from the toilet as she straddled it and brought the clippers to my head. I cried as my hair fell on the floor and Mistress made soothing noises to me. When she lathered my head and applied the razor, I was resigned to the situation.

I entered the shower, wetted down and let her apply shaving cream to my back, removing the thin hair with proficiency. She left me to my own devices and I removed my chest and arm hair.

Upon exiting the shower I looked at myself in the mirror and thought, "what a freak". The cool air on my skin felt strange and I rubbed my bald head, wondering how this was going to be seen at work. What kind of questions I was going to encounter from friends and neighbors. I applied more scented cream to my whole body, reflecting that I would have to buy more, and went off to find what was in store for me.

When I entered the bedroom, there was my wife, dressed in a classic dominatrix outfit that I had never seen before. Usually she dominated me in revealing underwear or lingerie. This was a new aspect along with everything else that happened today. Her gorgeous figure was clad, head to foot, in skintight shiny vinyl. A wide vinyl belt that laid just above the widest part of her hips with a large silver buckle. I noticed zippers, one that went from her belt line in front, through her crotch and ended at the belt line in back, and two more that were obviously for exposing her breasts. She had tall vinyl boots that ended just below her knees with three inch heels. Her hair was pulled back in her severe style that I loved so much. Her makeup was heavier than usual, making her seem a little slutty.

"Do you like it slave?" she did a slow turn, my breath catching as her perfect ass was revealed to me. If I wasn't her slave already, I would have fallen to my feet in front of this perfect vision and professed my undying devotion. As it was I dropped to my knees with a look of gratitude in my eyes and said, "You're lovely Mistress Cassandra".

"Come, get off your knees slave, I've got something for you too." There on the bed was a set of white lingerie, bra, panties, garter belt, and hose, a red pleated skirt and a white silky blouse with a rounded off collar. There was also a blond wig, a false nail set and some pieces of jewelry, pearl earrings, a pearl necklace and a gold tennis bracelet. I looked from the bed with it's presents to my wife and back again, knowing full well that I would be wearing these things and starting to feel my cock swell in it's confines just thinking about it. "When you are dressed as a woman your name will be Sissy, if you are not dressed as a woman and I call you Sissy you will take that as a signal that I want you in your Sissy clothes."

"Thank you Mistress," were the only words I could summon.

First I had to submit to having both ears pierced. I endured this like I did all the pain that was dished out, surprising myself by feeling an erotic twinge as the needle passed through. After bathing my lobes with peroxide I reached up to touch them and gave my Mistress a sheepish grin.

"You're going to have to leave these in for two weeks, then we can change them to suit your clothes. We can get you some real slutty dangly ones like you like me to wear. Do you like them?"

I thought of going to work wearing pearl earrings with dread, but I was more turned on by the prospect of getting dressed up. "Yes Mistress, very much."

"I knew my little slut would like it. Now come on get dressed, we don't have all day."

I started with the bra, dismayed that the filmy cups drooped but my mind stayed occupied on what I could put in them the whole time I dressed. I could use rolled up socks or perhaps I could wad up some of my panties or...

"Stop daydreaming little Sissy and get over here so I can put your makeup on." She scolded after I had completed dressing with her considerable help. I sat transfixed as she first lightly tweezed my eyebrows, applied foundation, blush, mascara, eyeliner, eye shadow and started to draw an exaggerated outline of my lips. After filling in my lips with a candy apple red lipstick, I looked in the mirror and was shocked. I thought I looked hideous and my obvious crestfallen appearance led my Mistress to say, "once we get the wig on, everything will fall right in place".

She was right of course, with the wig snugly on my bald head the effect was much better. I wouldn't pass as a woman but the illusion was much better than my previous hairless debut. I calmly waited as my wife applied the fake nails and sat blowing on them until the matching nail polish dried.

She ushered me to the side of the bed to show me my new shoes, black with two inch heels and a little strap. "These are low but we can get you something even sluttier when you've learned to walk in heels."

I tottered about the bedroom, holding my new blond tresses back with both hands while checking myself in the mirror. I stood looking at my profile while my Mistress came up behind me, wrapping her arms around my waist and snuggling in to kiss my neck. She reached up to grab my breasts and looked surprised. "I forgot one thing my dear." she said as she went to her dresser. She pulled out two silicone falsies with large protruding nipples and a very obvious rendering of dark, large arreola. Making me unbutton my blouse(did you know that women have the buttons on the wrong side?) she carefully positioned them so the nipples and their coloring showed through my bra. When my blouse was buttoned again you could definitely see the nipples poking out and a hint of the coloring.

My cock swelled at the sight of them. They felt so real as I once again tried to navigate on my heels around the room, my breasts giving a little bounce to my step. With some helpful pointers from my Mistress, "sway your hips more Sissy, put your toes down first Sissy," I started to feel more confident in my ability.

I was instructed to fix dinner for my Mistress and gladly complied. My abilities had improved after Mistress had expressed displeasure over my "defrosted" meals. I gladly set about dinner with a happy contented feeling. Then the realization that the patio door curtains were opened made me shuffle across the room in my new shoes and draw the curtains shut with a snap. I wondered what kind of show I had given the neighborhood.I finished dinner, called my Mistress from upstairs and she and I sat down to a well cooked meal.

"I'm glad you like your new presents Sissy. I think with a little work we could make you almost passable." I looked down, blushing as she spoke. "Of course you shouldn't expect me to help you with this all the time. I'm perfectly willing to give you little pointers, you know, girl to girl, but none the less you're going to have to learn to make yourself into a desirable woman."

My heart fluttered under her compliments, I felt so feminine and delicate in contrast to her controlling attitude. "Tonight I want you to practice walking in your new shoes. The sooner you learn to walk in them, the sooner we can get you some real nice slutty high heels. Make sure you practice with my instructions in mind. I don't want to come home to a clomping horse, I want to see you walking in those the right way. Okay."

"Do you have to go?" I whimpered in my best impersonation of a woman's voice.

"We're going to have to work on your voice too I see. Yes I do have to go out."

"Can I come with you?"

She looked at me with a new light in her eyes, as if seriously considering my request. "Not this time honey, but maybe next time if you do a good job on your housework and don't do anything to upset me I might take you along." She looked deep into my eyes. "Are you sure you want to come with me?"

"Yes Mistress."

"Well, like I said, maybe next time. Be a good girl while I'm gone and oh, you left quite the mess in the bathroom. Make sure it's spotless before I get back." I helped her on with her coat, I was glad she wasn't going out it in her catsuit without it. I accompanied her to the front door where she kissed me hard while groping my fanny with one hand and my breast with another. I felt very flustered after she left and the first thing I did was fix my lipstick before doing the dishes and tackling the hairy floor in the bathroom. I had some difficulty trying to perform my tasks with my new fingernails but was proud of myself for not chipping my red nail polish.

When I was done I was exhausted. I hadn't stayed up all night in a long time and was anxious to hit the sack. I entered the bedroom and found one last surprise for me there on the bed. A beautiful lacy black baby doll nightie with one of those filmy transparent robes. I only took off my blouse. skirt and slip, leaving on my hose, bra. garters, panties and heels. I wanted to look as slutty as possible when my Mistress arrived home, hoping for another night of being mastered by her and her incredible cock. Maybe even being allowed to cum.

The feeling of the silky attire was luxurious to say the least and very stimulating. I regretted my cock cage as I could have used a good cum right now but I was so exhausted it only took me minutes to fall asleep.

I awoke to hands rubbing all over my body and I could feel my cock again coming to life in it's stainless steel prison. "Your nightie makes me so hot Sissy." my Mistress spoke in a deep, throaty voice. The feel of her rubbing the silky garments over my body made me purr with pleasure. She reached down and caressed my boobs while kissing me. I felt as though she were fondling my real nipples as she pinched and tweaked them. She pushed her strap on towards my face and I anxiously gobbled her thrusting penis. I wound up on my hands and knees, patiently waiting as Mistress pulled my panties down to reveal my rosebud. We came together with a small amount of pain on my part when she pushed the large head past my sphincter, easing her wonderful cock into my depths with a contented moan on my part. She rode me until she came, all the while my cock struggled within it's bonds, aching and throbbing. I fell asleep immediately afterwards but was awakened again later as my randy lover again positioned her penis at my entrance and pushed it home. My submission was complete as she again took me and I willingly complied with serving her happiness. The feeling that I was just a fuck toy for my wife did not escape me, but I willingly accepted my role and derived great pleasure from serving her needs.

I woke to the alarm in the morning, sleepily rubbing my eyes as I headed to shave. I looked at myself in the mirror and removed my wig, retrieved the nail removal liquid from the kit, and set about getting ready for work. I normally set aside an hour in the morning to get ready, about twenty minutes for a shave and a cup of coffee and forty minutes for the drive, but I was way into my allotted twenty minutes and my nails were only off one hand! I tried to rush matters, scrubbing my makeup laden face with one hand while soaking the nails on my remaining hand, but time inexorably went by much to fast.

Needless to say I was again late for work and this time spent awhile in my supervisors office, trying to explain my newly shaved head, my earrings and my tardiness. I felt he could see right through my lies and tried to ignore his scrutiny of my person. I signed the written warning with relief, happy to be out of his office and onto the floor. The reaction from my co-workers was less reserved but instead of light hearted ribbing I only received looks of scorn over my shave and the appearance of my earrings. I felt they were discussing me behind my back and was sure of it when they broke off their conversations at my approach.

The day was a disaster, no glaring errors on my part but I could feel a lack of confidence from my supervisor, my fellow machinists and machine operators. When I was asked to take over a milling machine by my boss and then watched as another supervisor came and took over my duties in my section, my shame made me miserable.

Again I drove home resolving to talk with Mistress about my job and my troubles. It had been a long day of one mistake after another and I felt as though I was on my way to losing my job. This had to stop.

I entered our home with every intention of laying it on the line with Mistress Cassandra. I found her in the living room dressed in black skintight silky hotpants, a shiny gold lame~ top that tied in the back so I knew she had no bra and a pair of stiletto heeled boots that came up just past her ankles. Her hair was loose and her make up was in the slutty fashion that she had recently taken to. I checked myself from asking any questions and said, "Mistress, we have to talk."

She finally looked up at me, gauged my temper and mood and said. "We can talk after you've stripped down, taken a shower and placed your cuffs on."

A shower sounded good and I could certainly talk to her afterwards, so I trudged to the bathroom and carried out her assignment. After my bath I took the luxury of smoothing moisturizer over my hairless body, luxuriating in the smoothness of my body. I should probably shave tomorrow I thought to myself, grabbing my restraints and buckling them in place. After pulling out a new pair of panties and slipping them on I went back to the living room to begin my discussion with Mistress. She wasn't there so I headed for the kitchen. As I entered I thought I heard the radio on some talk station but to my horror there sat another woman at the kitchen table with my wife, drinking a cup of coffee.

I quickly ran out of the room, embarrassed by my near nudity, and was about to go upstairs when I heard my Mistress calling out to me. "Come here slave, come here now!" Was she kidding? I couldn't go in there with that stranger. I wanted to run but I stood there at the bottom of the stairs watching as my Mistress came out of the kitchen holding her crop.

Whack! The crop came down on my back as I cowered from her wrath. "Don't you dare embarrass me in front of my friend. Get in that kitchen now slut!"

I walked into the kitchen with my eyes downcast, my face burning from embarrassment. I managed a quick peek and saw an attractive redhead, probably in her early forties, dressed in a black wrap around dress, glaring at me over the rim of her coffee cup. Mistress Cassandra came up behind me and pushed me further into the room.

"Say hello to Mistress Lindsay." I mumbled my greeting and was rewarded with another lash on my butt. "Say it slave!" I spoke out loud this time.

"Hello Mistress Lindsay."

"Kiss her feet." I looked at my wife with disbelief in my eyes. "I don't want to have to tell you again." Another lash on my ass.

I scrambled to her booted feet and kissed them reverently as she looked on.

I turned to see Mistress Cassandra coming towards me. She grabbed my arms from behind and secured my cuffs together. Turning she left the room. I waited in silence with my eyes downcast. Neither one of us spoke. Mistress Cassandra came back in the kitchen with her coat on.

"You are to obey Mistress Lindsay as you would obey me. She is here for an evaluation, I hope you do not fail me."

When I heard the front door close after her, I raised my head to look at my new Mistress. She returned my gaze with a scowl. "So, I hear you like to play games."

wormwood
wormwood
10 Followers
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