Chapter 5

Originally written by 4Play and modified

Tonight was one of our regularly scheduled Fantasy Weekends and, as usual on these occasions, I was both excited and nervous. We had originally set up these “special” nights to fulfill my desires for some of the wilder aspects of sex. Ever since she had brought other people into our private game, she had increasingly grown more perverse in her scenarios. I thought dressing me as Slut had been a onetime thing; now it was required every Fantasy Weekend. Watching Masters and other Mistresses in action had seemed to validate her treatment of me, as well as providing her with a host of new ideas.

My wife Chris had quickly discovered that she enjoyed the power of being totally in charge, and our sex play had become her exercise of power. She used me as her sissy sex slave to satisfy her every whim. While I had some fantasies of being submissive to her, I hadn’t realized that once she experienced being Dominant, she would turn that into a permanent part of our lives.

In the two weeks that had elapsed since the Mistress Rachel’s wild party, my wife Chris had not mentioned a word about the events which had transpired there. While she had obviously had a very exciting time, I had spent much of the party bound and hooded in what was called the Playroom, but was really a dungeon. My mouth and ass had been freely utilized by anybody and everybody who cared to take advantage of my helpless condition. All of the Dom’s at the party had. Even several of the other slaves, following their Master’s or Mistress’s directions, had used me.

Mistress Zelda had left her mark, a Z formed on each cheek of my ass by welts from her whip, on me. The most drastic thing was having my nipples pierced! The pain had been intense, but fortunately short-lived. My nipple rings were in place, and I was constantly aware of their presence. The pain was gone, but I felt them every time I moved and my nipples were kept constantly erect.

The welts on my ass were fading and I could now sit without wincing in pain. My nipples were not completely healed, but with the care I was giving them, they soon would be. Curiously enough, Chris had ignored my rings; acting as if they didn’t exist. That was a big relief to me, since I would have died if she had been using them as a dominance tool during the healing process. That practice would begin soon enough I assumed, a prospect which both frightened and excited me.

My thoughts had become very confused lately and I found it difficult to decide upon a course of action regarding our marriage. The submissive fantasies I wanted to act out, which resulted in my pledge of Fantasy Weekend slavery, now seemed very tame indeed. Once Chris had discovered the exhilaration of having unlimited power, she could not seem to get enough of it. She had constantly pushed me far beyond any limits I would have established beforehand; had I even thought to set restrictions on her power. With the benefit of 20/20 hindsight, I certainly should have!

One part of me resented the degrading things I’d been forced to do and wear. Being a sissy sex slave was one thing as a harmless fantasy, but quite another to endure on a regular basis. The pain, which had seemed so sensuous in my mind; really hurt in actual practice. Bisexual experiences had never been a part of even my wildest flights of imagination and, more than anything else, being used sexually by other men had sapped me of my last vestige of manhood.

I suppose most men would have revolted, and refused to continue in such a state, but another part of me felt enormously proud of being a good slave to my beautiful Mistress. I had never seen her as happy as she was in her role as Mistress Chris. Her pleasure was worth a lot to me and made the unbelievably perverse things required of me to evoke such joy seem worthwhile. The scariest part was that I was starting to get turned on by submissively obeying her commands. Somehow it seemed, the more debasing her demands became; the more excited I felt carrying them out. Obedience seemed more crucial than sexual satisfaction, a situation which made rebellion a possibility that grew fainter as each day passed.

Chris and I had always been quite open with each other, freely discussing everything; but we never talked about the Fantasy Weekend experiences. She must have felt that as Mistress Chris she was entitled to unquestioning obedience, and no explanation was needed. I was reluctant to bring up the humiliating things I’d been forced into; feeling that Fantasy Weekend was better kept separate from the rest of our life. Strange as it might seem, this unspoken understanding had enabled us to maintain a normal, loving relationship except for our bi-monthly wild excursions into kink.

My curiosity about what Chris had planned was mixed with a sense of dread. I was hoping we would spend this weekend alone; since when Chris and I played together things didn’t get so extreme.

Chris had come home from work and immediately went into her Doms role ordering me to go take a shower and get cleaned up. “I am having company tonight, and I don’t want to have an unkempt slave hanging around!” she announced. She noticed my dejected look and added, “You wouldn’t want to mess up and displease me, would you?”

I humbly replied, “No Mistress” and hurried off to get cleaned up.

While showering and getting all cleaned up and ready, I wondered who she had invited this time. Once before she had invited a guy from a BBS named Brian to come over and they used and abused me, humiliating me while they had great sex. I suspected that this would be another such evening, a prospect I dreaded. By the time I finished getting cleaned up, I realized that Chris had not given me any directions as to what to wear and decided to go ask her. Wrapping a towel around me, I went back to the area where Chris was playing computer games. Just as I got there, the doorbell rang. Without even turning around to see how I was dressed, Chris ordered, “Answer the door slave”.

I went to the door embarrassed to be wearing only a towel, but not wanting to anger Chris. Upon opening the door I recognized Pat, a lady we had met last week at a party. She and Chris had chatted privately for some time and Chris had told me on the way home that she really liked Pat. It was obvious that they had discussed our Fantasy Weekends and that Chris had invited her over to share an evening dominating me. Maintaining my composure, I welcomed Pat and escorted her to Chris.

Chris got up and they hugged each other. Pat seemed a bit nervous, telling Chris that she had never had a chance to play a Dominant role before. Chris reassured her saying, “Don’t worry about it a bit dear, you can’t do anything wrong tonight. Whatever you want, my slave will do.” Pat, looking somewhat dubious, said; “Really? Anything??” Chris nodded yes.

Pat turned to me and said, “Drop that towel slave; let me see you naked.” This surprised me, coming so suddenly with no working up to it; but I immediately dropped the towel from my body and stood naked before the ladies. Pat grinned at my obedience. She was going to enjoy being a mistress!

Chris told me to get them some wine and went into the family room to sit and chat. I filled two wine goblets with a nice white wine and delivered them to the ladies. Pat said, “Chris you have a nice servant here”. Chris replied, “It’s not too bad as a maid either!” and laughed. “Can we do that? Dress him as a maid?” Pat asked. Chris assuredly said, “Certainly my dear. Tonight we can do anything we want!” Chris looked at me standing naked awaiting their pleasure and asked me, “Isn’t that right slave?” I bowed my head and answered, “Yes Mistress”.

Pat reached her hand out and fondled my clean-shaven balls. “I’ve never seen a man’s privates shaved before, they look kind of cute that way!” She said. “Much less menacing than those hairy things men are so proud of.” She added.

Chris nodded her agreement remarking, “Yes indeed, my slave keeps his body bald at my insistence. It takes him time to shave it and serves as a constant reminder of his slave status. That hairless body is very easily feminized.”

Pat seemed very impressed by Chris’s confident attitude and my submissiveness. “This is very interesting, I’d like to find out more about what your slave will do, how you got such control and many other things,” Pat said. She then asked, “Can we talk in private for a bit?”

Chris said, “Of course dear, perhaps the hot tub would be a comfortable place.” Chris told me to fetch them some towels. I quickly got the towels and when I delivered them was told, “We are going to be alone for a bit, meanwhile get into your ‘slut’ outfit and start fixing supper.”

I murmured, “Yes Mistress.” and left to obey my orders.

“Damn!” I thought to myself, “I’d hoped for a quiet evening at home tonight serving my Mistress.” It was now obvious that I was going to be put through the hoops by two ladies tonight. As I got into my ‘slut’ apparel, I knew the Ladies were planning my ordeal. What they had in mind I didn’t know but felt safe in assuming that my pleasure was in no way involved in their considerations.

Since I had shaved my body during my shower, getting into my ‘slut’ outfit went rather quickly. I painted my toenails first then began applying my makeup. Chris preferred a wanton, whorish appearance in her sissy slave; so I used the blue eye shadow, lots of rouge, gaudy red lipstick and the long fake eyelashes to achieve the desired effect. When the mascara was liberally brushed on the long lashes my face looked very slutty indeed. I put on some big hoop earrings and then the wig. It was a blonde wig styled to give me the look of a bimbo.

I rolled the black mesh nylons onto my hairless legs and secured them to my garter belt. Next, I put on the black, padded bra and slipped into the white blouse with the puffy sleeves. Its low cut neckline would make my nipples easily accessible. If past experience was any indication, I expected that they would be getting quite a workout this evening. Deciding to leave the black lacy panties off, I stepped into my black mini-skirt. It barely covered my privates, coming only to mid-thigh. I knew that with any bending I would be exposed unless I moved very primly.

My transformation was nearly complete now, so I stepped into my high heeled shoes. They had 4” heels and had taken me some time to learn to walk in. Chris had me wearing them every Fantasy Weekend though, and now I could manage quite well in them. A quick spray of cheap perfume and I was ready for the final step. I always waited until last to glue on the fake fingernails. Their length made the other transformation steps too difficult. Once they were in place, I painted them the same garish red as my toenails. While they dried, I studied myself in the full-length mirror. The image was perfect, I looked like a blonde floozy ... just the way Chris liked her sissy slave!

Figuring that the ladies would be ready for a refill of their wine glasses, I put on my lacy white apron and went out to the Hot Tub to get their glasses. “Oooh, how nicely slutty your maid looks now!” said Pat.

Chris just smiled and responded, “Thanks, She is a tramp, but serves me well.” They both laughed making me feel even more embarrassed. Chris’s penchant for having me dressed this way when in my slave role was bad enough in front of her alone, but was more than doubly humiliating in the presence of Pat.

Executing a dainty curtsy I asked, “Would the Ladies care to have their drinks refilled?” They both held up their empty glasses, which I took and went to refill them. As I left their snickering sent a shiver up my spine. This evening seemed to be dedicated to my humiliation.

When I returned with the refills, I had to squat demurely keeping my knees together to hand them to the ladies. Pat reached under my skirt and fondled my cock. “Her clit is excited,” she remarked to Chris. She stroked me to full erection and then just as I felt near to orgasm, sent me away with a tent-like bulge in my skirt.

“I laid out two nice steaks for tonight, fix a couple of potatoes and a nice salad to go along with them Slut,” Chris told me.

“Yes Mistress,” I replied.

The first thing I did was to light the gas grill to let it heat up while I prepared the rest of the meal. Once the potatoes were in the microwave oven, I made a large bowl of salad adding all of Chris’s favorite ingredients. When the salad was finished, I took the two nice T-bone steaks and placed them on the grill. Leaving them to start cooking, I scurried back in the house to set the table. I used the good dishes, crystal goblets, best silverware, and even linen napkins to make the table suitably attractive for the ladies. I even lit two candles to make it seem more luxurious before dashing back out to flip the steaks.

“Mistress, your supper will be ready in a few minutes,” I respectfully announced. Chris got out of the hot tub and had me to towel off her body. Pat also wanted the same service, which I of course supplied. Being so close to two such delightful naked women caused my erection to return.

Pat laughed as she noticed my reaction saying, “The poor slave is probably aching for some relief.”

Chris responded, “Don’t worry about Slut, that bitch will get more sex than she wants later.” They both laughed as they went into the house. Retrieving the steaks from the grill, I followed them inside.

Chris asked, “What is this third place setting for Slut? Did you presume that you were to dine with us?”

Realizing that I had messed up, I answered, “I had hoped so Mistress, but I will remove the extra stuff immediately.” As rapidly as possible I removed the setting for my place at the table and stood by the table waiting to be of service if needed. Chris and Pat chatted casually as they ate, although there seemed to be a suppressed level of excitement underlying everything. The wine they’d already consumed had loosened up their inhibitions and they giggled frequently. My only task was to refill their goblets once during the meal.

When they were finished eating, Chris pushed back her chair and motioned for me to kneel. “That was a good meal Slut, now I need to relax a bit ... lick me.” She ordered. As she leaned back and spread her legs, I began to lick gently at her vaginal lips. Slowly I worked my way to her clit licking and sucking until she became aroused.

Pat watching from behind remarked, “Slut does have a nice ass.”

Chris said, “Yes She does, and I would be honored if you would like to fuck it.”

Pat responded with undisguised delight, “Wow! That would be something that I’ve never done before! Lots of guys have tried to do anal sex on me and I hate it! This is an unexpected pleasure to be able to shove something up one of them. Could I really do that?”

Chris said, “Of course Dear, I told you that tonight you can do whatever you want with my slave.” Reaching over to hold Pat’s hand she added, “You are my guest tonight.”

Chris pulled my head away from her crotch and pointed towards Pat. “Do her for a bit to warm her up,” she commanded.

I crawled over to Pat and immediately began lapping at her bottom. Pat responded rapidly and actually reached orgasm before Chris returned with the toys. Chris had inserted one end of a double dildo into herself and was holding out the strap-on dildo to Pat. “Come over here and suck my cock Slut” Chris demanded. With me on my hands and knees in front of her, she shoved the fake cock past my lipstick covered lips into my mouth. “That’s my good little cock sucking bitch.” she praised as I sucked.

Pat meanwhile had strapped on the dildo harness and knelt behind me. Chris told her, “Slut’s sissy pussy is awfully tight, you’d better use some of that Vaseline.” Pat took the jar of Vaseline and smeared my anus with it liberally. She pushed one, then two greasy fingers inside of me forcing the lubricant inside of me. The pain of the intrusion soon was overcome with erotic sensations and I began to squirm. Chris held my face in her hands, keeping my sucking going as Pat entered my behind with her dildo. Pat relentlessly pushed the dildo further in until it was up to the hilt. I was impaled both front and rear!

Chris told Pat, “This bitch is easily controlled by her nipples If you pinch them you can regulate her movements to suit you.” Pat pulled my blouse out from where it was tucked into my skirt, unhooked my bra and pinched my nipples between her thumbs and forefingers. Slowly she began thrusting and withdrawing, pulling my rear to meet her thrusts by yanking on my nipples. This scene was unbelievable! My mouth was being fucked by Chris while Pat was fucking my ass and savaging my nipples. I was a helpless toy being used for the ladies’ lustful pleasure.

It seemed to take forever before both Pat and Chris reached orgasm and they released me to collapse on the floor. I had a throbbing erection and still had not climaxed. The ladies hugged each other and Pat said,” That was great! I don’t know when I’ve had so much fun!”

Chris smiled and said. “The night is still young my dear, you may feel like doing it again. Remember anything you desire Slut will do.” They clinked their wine glasses together and toasted to their night of pleasure.

Chris told me, “Get this table cleaned off, and clean yourself too. You look like a freshly fucked Slut!” They both giggled at the obvious irony of that statement and walked out of the room. I struggled to my feet, re-hooked my bra, tucked in my blouse and straightened the mini-skirt. It was bad enough being dressed like this without being a disheveled mess. As soon as I had cleared the table and loaded the dishwasher, I went into the small bathroom to freshen my makeup. I washed my aching bottom to remove the slimy stuff oozing out. While still feeling very humiliated, weary and sore at both ends; at least I looked presentable again.

Knowing that I shouldn’t stay gone too long, I returned to the Family room to find Chris and Pat sitting on the couch conversing as if the recent events had never happened. They had both freshened up their makeup and changed into something sexy. This seemed strange to me, they surely weren’t trying to impress me with their appearance! It seemed to be a waste of energy if, as they suggested earlier that there might be a repeat performance later. While I was still puzzling over this strange behavior, the doorbell rang.

Chris said sweetly, “Answer the door; will you Slut dear?” Looking at the ladies’ expressions I knew that this had been planned all along. They were expecting company, someone else to enjoy degrading me! I dutifully went to the door and opened it. There stood Brian with two other guys. They pushed their way past me as Brian led them into the Family room to meet the ladies. I closed the door and followed them.

Brian was kissing Chris’s hand and saying, “I’m so pleased you called Chris. I see that Slut has responded well to your training.”

Chris nodded her head in acknowledgement of his praise and introduced Pat. “She is my friend and has been invited over for a bit of play, we started without you.” Both Chris and Pat chuckled at this comment.

Brian introduced his friends to the ladies. “The smaller guy here is Wayne; I brought him as a date for Pat. This big fellow is Jake; he is mostly gay and can be brutal so I figured that he would be a perfect date for Slut.” I gasped at this last statement; I wasn’t gay, or even bisexual. Jake’s sheer size was quickly turning this from a role-playing game into a nightmare!

Chris ordered, “Get our dates some drinks Slut.” Our dates! Those words cut like a knife. It wasn’t kinky enough for her to use me as her sissy slave, now she had fixed me up as a date for a man. I obediently took the drink orders and filled them, handing each his drink with a dainty curtsy. Jake took his straight shot of bourbon and downed it in a gulp, chasing it with a big swig of beer. He let out with a loud belch, reached out his massive arm and pulled me to him. He planted a big wet kiss on my mouth, forcing his tongue inside me. I wanted to gag and tried to pull away which enraged him.

“This bitch needs her spirit broken a bit.” he snarled, pulling me across his lap as he sat on a chair. Lifting my skirt he began spanking my bare bottom. No pretend swats, these were resounding whacks that stung and really hurt. I wriggled trying to escape the blows, but his powerful arm pinned me in place. After a half dozen blows to each cheek, he let me up and asked, “You gonna play nice now babe? Or do you want some more?”

With tears streaming down my cheeks and sobbing, I muttered, “Yes Sir, I’ll do what you want.” I glanced through teary eyes at Chris who was sitting necking with Brian and saw her smile. It had been at my insistence that she tried being dominant and now she had given me far more kinkiness than I ever dreamed possible. She felt entitled to gloat a bit over the obvious regrets I now felt.

Brian suggested, “Perhaps we should leave these two lovebirds to get acquainted.”

Chris replied, “I can hardly wait to get in bed with you too Brian dear, but I’d kinda like to watch Slut please Jake for awhile first. My dear husband wanted to be a woman, now I want to see her perform like one!”

Pat added, “I want to watch this too, please.” Wayne who was fingering Pat’s pussy nodded his agreement. God! Not only was I going to be Jake’s ‘woman’ tonight but I was going to be forced to do it in front of Chris and the others. There could be no greater humiliation imaginable!

Jake stood up and gave me a deep kiss, fondling my sore bottom with his rough hands. His body pressed against mine allowing me to feel his erection. He knew that I was a man, but he wanted to have sex with me while I was dressed as a woman. We kissed for a couple of minutes before he ordered, “Undress me, bitch, I’m going to give more than you ever had before!” My long painted fingernails fumbled with his shirt buttons until I was able to slip it off exposing his very hairy body. The revulsion I felt at having to undo his belt and unzip his fly was overcome by the fear of what would happen if I refused, so his pants were soon removed also. He looked more like a hairy beast than a man, but the ladies applauded his large erect cock. He gave a bow of mock modesty and then roughly pulled off my blouse. His big hands were able to unhook and remove my bra with surprising ease.

Jake pushed gently down on my shoulders forcing me to kneel in front of him. “Suck my dick Bitch” he ordered waving it in front of my face. When I parted my lips and took the head into my mouth Chris and Pat both applauded again. Jake held my head with his hands as I tentatively began to suck on him. There was no escaping my fate!

Chris kept encouraging me by chanting, “Suck Slut, suck.” When Jake began thrusting his huge cock it made me choke and gag. That seemed not to matter to anyone, Jake was having his way and Chris loved seeing me as a sissy cocksucker. Pat had never seen two men together and was getting quite turned on also. Brian and Wayne liked seeing me humiliated and were happy feeling up the girls until they were ready to have sex with them.

When Jake was about to come in my mouth he pushed me roughly away causing me to fall backward. Moving rapidly for a big man, he picked me up and placed me on my hands and knees facing Chris. “Beg me to fuck you Bitch” He ordered. Before I could even bring myself to utter such disgusting words, he smacked my ass a few quick swats.

“Oh please Sir, Please fuck my pussy.” I pleaded in earnest. Anything to avoid those brutal spankings! Everybody seemed to find my total surrender amusing as a snicker ran through the gathered crowd. Jake forced himself inside of me firmly with a quick thrust. It hurt terribly, but I was thankful for the copious lubrication Pat had used on me earlier. But for the remaining ooze, I would have been ripped open by Jake’s over-sized equipment. He grabbed my hips and began thrusting in earnest until he came deep inside of me.