Christmas Dinner with my Boss

CHRISTMAS DINNER WITH MY BOSS AND MISTRESS

This is my first story and has been created by permission of my Mistress. I was ordered to write it to show what wishing for something does when it comes true. For those who do NOT like sissy, cuckold or unfaithful partners don't read it, move along nothing to interest you here! For the rest please enjoy and positive feedback is always welcome.

To Begin;

I was married to my first wife for many years and that is where my cuckold experiences started. Well documented in previous stories on various sites!. Without going into to much detail her and I got back together recently, where she discovered my real sexual desires, mainly being a cuckold, a sissy slave and with the help of an on-line master I had started communicating with she became my Mistress.

After several weeks of discussion, talking over what she would have liked in our previous relationship and what I had wanted and still did we decided t give it a go again. To begin with it was all a bit trial and error and once she had me in a cage was when things changed. I had a bit of a flaky and she left me caged for a while and then Christmas was approaching and this situation arose where once and for all I would realise I was a sissy cuckold that would always have to do what I had desired, but putting it into practice and becoming reality was a lot harder and more difficult than I thought. However as the saying goes 'iv'e made my bed, now lie in it'

About a week before Christmas my ex informed me that she had invited my boss for Christmas dinner, he was a single divorced male with a reputation for having numerous affairs at the workplace so my suspicions should have been immediately aroused. However it wasn't until that dinner I realised just how embarrassing it would be, nor did I realise what was about to occur. I hope you enjoy this relating of what happened as much as I eventually did.

Dave my boss was expected soon, and I had dressed in my best casual wear. I went downstairs to find Ann looking at me strangely before she shook her head, hand on hip and waving a finger in my general direction.

"no, no no those clothes will never do" she said

"I have some clothing sorted for you, it's part of the Christmas surprise I have organised for you"

She marched past me and went back upstairs ordering me to follow, which I obediently did. (I knew better by then than to disobey her, the last time I had I couldn't sit for three days!)

She entered her bedroom (I had my own room by then) and produced a bag which she laid on the bed, then she pulled out a maids outfit, my jaw about hit the floor!

"I ca...I can't wear that with my boss coming here for dinner!" I stuttered. My face already burning red with the possible embarrassment.

"You most certainly will, and not only that you will serve us both and eat alone whilst your boss and I get a chance to know each other better. I'm hoping that being a divorced man, that he is able to satisfy my Christmas wish for me!"

I realised that not only was I to be embarrassed and made a fool of in front of my boss but my ex was gong to fuck him and do so in front of me. I felt the deep falling of my stomach as I realised my deviance was gong to be taken further than she had previously. I had only ever been told of her meetings with her lovers up to this point, now however I was going to witness one of them. I was excited, sexually aroused if you can call my caged cock aching at the thought arousal. However my Christmas was about to get even worse.

I stood staring at the outfit before she took another bag from her closet and laid it in front of me. Opening it she pulled out some sort of rubber clothing, before opening the item out for me to see it was a pair of rubber pants which had a dildo in the rear section and a small hole at the front, obviously for my cock to go through,

"I bought these for you as well", she announced

"now get dressed and once your ready you can come downstairs where I will give you your orders for the rest of today"

She watched me standing there my face bright red still, and my mouth open aghast at what was about to happen.

"Don't just stand there gawking, get stripped and I will help you get ready!" she said loudly.

I quickly stripped off, and she helped me get into the rubber pants. She applied some lubricant to the dildo and I felt it slide easily into my anal cavity, rubbing against my G spot ever so nicely. My cock had been released from its cage to allow it to go through the hole at the front. Once they were on it actually felt fairly nice until I moved, then that dildo device started rubbing against the g spot and I felt the familiar stirrings in my groin. Any thoughts of being allowed arousal however were soon dispelled as she quickly stepped forward grabbed my tiny cock and shoved him and my balls into a new pink coloured plastic cock and ball cage. God it was a neat fit, let me tell you. I could feel both my balls and my cock pushing against the frame constantly. Once she was satisfied that all was in order there, she told me to put on the maids outfit and come downstairs. I dressed as quickly as I could. The top had false breasts in it and the skirt was so miniscule my rubber panties and cock / ball cage were clearly visible when standing. Oh my god I thought this is going to be so embarrassing but I took a deep breathe pulled on the hold up stockings and my flat 'sensible' shoes Ann had bought for me weeks before. I took a quick look in the mirror and put on the wig and make u up she had laid out before descending the stairs.

"That looks much better cucky, don't you think" she said

"Yes Mistress" I replied.

Once she had told me what s going to happen, regards serving. (a small bell was placed on the table so that I would not disturb them during their meal. I was ordered to wait by the door for Dave my boss to arrive. I stood there, shaking but at the same time excited, this was what I had always imagined it would be like. But to finally do it I was finding it really exciting yet I had still trepidation about my boss's response.

It wasn't much longer before the door bell rang and I answered it, dressed as a maid. There stood my boss, (Hello maid Ian is the boss of the house at home, if you would be good enough to inform her that I am here now run off and get her there's a good sissy!"

My jaw must have hit the floor, but I immediately did as I was told and informed Ann that my boss was at the door asking for her. She followed me back out to the front door, which stood wide open allowing anyone passing or watching a view of me in my maids outfit and bright red in the face.

"don't just stand there Dave, come in, come in, my maid will take your coat and then fetch us a drink!" she smiled.

Ann then slipped her arm through Dave's and the two of them walked into the living room. Not knowing what to do, I followed them, placing my Boss's coat over the rear of a chair. They sat down side by side on a sofa. I started walking to a chair on the other side of the room but Ann stopped me by saying, "No sissy You can go and prepare the Christmas dinner for us. When it is ready you will return and inform us of that fact!"

"Oh and bring us both a G&T why don't you" she ordered. I immediately went and made them their drinks as my boss laughed out loud saying

"You have got him well trained, I wish his colleagues at work could see this they would end themselves with laughter, a perfect little sissy isn't he!"

"Oh he has had his moments but he knows who is boss now, don't you cucky?"

"Yes Mistress" I replied taking care to bow slightly as I did.

"Now off you go there is a meal to prepare, and if we require another drink I will ring this bell for you to serve us!" I looked over and she had a small bell which she shook allowing me to hear it tinkle.

"Yes Mistress" I said again before leaving the room.

I slunk off to the kitchen to do the bidding of my mistress where I spent the next hour finishing off the preparation of the meal, ensuring the plates were warmed, and serving drinks every time the bell rang. Once the meal was ready, I returned to the living room where the table was already set for their meal. As I entered the room I could see my boss had his hand up the inside of her thigh under the dress and was obviously fingering her as I could hear wet sounds, soft moans and the smell of sex in the air.

"The dinner is ready Mistress, shall I begin serving?" I asked.

She replied in the affirmative and I spent the next two hours serving all four courses, more drinks, cleaning dishes, drying them putting them away and clearing the table. I also got to eat my dinner by myself in the kitchen. I could hear them talking about me amongst other things. Once the meal was over I was called to the living room again, where I found them almost naked caressing each other. My tiny cock just twitched in its cage and I felt the feelings of excitement building in my stomach, my mouth went dry and my heart raced. I was going to be allowed to watch them fuck was I?

I stood there my arms behind my back, until Ann told me to go upstairs and undress, I was to put on a pair of stay up stockings and wear my red high heels but nothing else, then wait outside her room for them to come up. I Had a puzzled look on my face obviously, as Ann grinned as she said;

"No, sissy Cuck You're to be part of the entertainment" I then understood perfectly, my continued punishment for my recent bad behaviour where Ann left me caged for a fortnight was to continue.

Once I had undressed completely, bar the cage and the rubber pants, I carefully folded all of the uniform it over the arm of a chair. I then went and stood outside her bedroom door and waited as ordered. I heard them coming up the stairs and watched as Dave carried one of the dining room chairs towards the bedroom. Facing both Ann and Dave wearing nothing but my rubber pants, and cage, the nylons, and red high heel shoes. Ann looked at Dave and said,

"Didn't I tell you she was a hot little bitch?"

Dave grinned, "You were right. And she'll do anything you tell her to, wouldn't she?"

"That's right. Anything at all."

"Good we will put that to a test after" he grinned.

"for now he can watch while I fuck his gorgeous ex wife in front of him and assist when asked OK"

"What a great idea!" Ann laughed.

"Come on cucky, time to see what a real cock can do to your little woman!" and with that we entered her bedroom. Ann lay on the bed, and spread her legs wide, ordering me to get her pussy ready for my Boss's cock. I lay between her thighs and lapped eagerly at her already dripping pussy. Pushing my tongue in a and out of her slit like a little cock. She told me to use my fingers, so I eased two in then three and finally four were flashing in and out of her juiced up cunt as I lapped up as much of her excretions as possible.

Dave was meanwhile kissing her deeply, while playing with her tits, squeezing and pulling on them, twisting her already hard nipples until she was moaning and groaning.

Then Dave told me to get out of the way, he flipped her onto all fours at the edge of the bed before ordering me to sit with my back against the side and bend my head back so I could lick her cunt as he fucked her. I was in heaven! I was mesmerised as his thick meaty gnarled cock pushed against her slit and started to disappear inside her. My own cock was already dribbling with pre cum despite the confined space it was in. I lapped at her clit which was sticking out like a bolt!

"That's it cucky lick her cunt you little sissy pervert!" Dave scolded.

"And don't forget to keep my balls clean either!"

I swallowed hard and stuck my tongue out as far as I could and let it lick all over his heavy swinging balls as the slapped against her Mons.

"Oh god that feels so fucking good you cuckolded sissy" he moaned.

I managed to do that for about ten more minutes before my ex wife began moaning and squealing with pleasure then collapsed on top of my head her belly pressing against my brow forcing me to stay still underneath her. Her juices flowed feely into my open mouth as her cunt squelched, sprayed and farted under the assault of Dave's cock as he pounded the shit out of her.

Go On you little slut, take my cock, take it all, you fucking little slut!" he grunted

"Oh god Oh god Fuck me Dave, fuck me I love it......your the daddy... your the fucking daddy!" she squealed as he pumped his cock in an out of her wet willing cunt. Then I felt him ram his cock all the way in and he groaned and bellowed like an old bull as he shot his load up inside her cunt.

They lay still for a few minutes until Dave's cock went soft and slipped out of her ravaged cunt. I slid of the bed and could feel the wet patch under my own ass where I had dribbled throughout the assault of my ex wife's pussy.

I was immediately ordered onto the bed to clean her up which I eagerly did, slurping and sucking as much of their combined juices from around, over and inside her ravaged pussy. My face was smeared in it. Then when I was done, Dave laughed loudly before he said get those rubber pants off.

I eased them off as carefully as I could covered in my own excretions as they were. The dildo making a popping sound as it slid out of my anal cavity, it felt strangely empty however I need not have worried for long as I was about to find out.

"Clean them up before you put them down!" Ann ordered. I eagerly licked all the juices of them until they were clean then laid them over the same chair as my maids outfit. She also ordered me to come over so she could release me from my cage which I was pleased about as my cock was aching from being confined and witnessing all the sex I had.

"Now let's see if he does as he is told shall we?" he said to Ann

"Tell her to get down on her hands and knees and stick her ass up in the air."

"come on dear, you heard the man," my wife said.

Doing as instructed, I got down on the floor and turned away from them. Ann ordered, "Open up, dear. Give us a better view of your pretty pussy in your panties." Dutifully, I spread my knees further apart and stuck my ass up in the air. I was facing away from the bed at that time.

"Tell her to play with herself," Dave said to Ann. Not even waiting for her to relay the instruction, I slipped my right hand back underneath me between my legs and began to stroke my cum stained cock. God, it felt good! Just as I was approaching orgasm, I heard a moan behind me. Turning my head, I saw that Ann had Dave's cock in her hands and was slowly jacking him off.

"Come take a look at Dave's big cock," Ann said.

Still, on my hands and knees, I crawled over to the couch. "Doesn't Dave have a nice dick, dear? So big and fat. Wouldn't you like to suck on it?"

With my throat dry and scratchy, I managed to croak out, "Yes, I want to suck his cock."

And even though I had sucked a cock before I really did want to suck Dave's big impressive member down my throat and taste his pre-cum on my tongue along with his rubbery-hard dick flesh.

With a huge smile on her face, Ann tilted Dave's fat cock toward my face as I rocked forward from where I knelt. Opening my mouth, I accepted my new gift. As I closed my lips around his cock-head, I couldn't believe how good it felt I thought my own cock was going to burst it was as hard as a rock and it felt like I was peeing myself with pre cum juices. Ann kept her fingers on the base of Dave's cock and jacked him off as I sucked on him. I heard her say,

"I think the little sissy cuckold wants you to come in her mouth, Dave."

With that, she began jacking him off harder and faster. Within seconds Dave was thrusting his hips, lifting his ass up off the beds edge. I closed my eyes tightly, savouring the feeling, one I had longed for. I clamped my lips tightly around the thickness of his shaft as his cock glided smoothly in and out of my mouth, the huge veins all over his manhood, and one large thick one on it's underside were massaging themselves on my tongue. Suddenly, Dave moaned and I felt his cock swell in my mouth, almost immediately a hot, salty slickness filled my mouth.

My own cock, swinging around beneath me freely, erupted and I shot a load all over the carpeted floor. After I had swallowed every last drop of Dave's cum, Ann withdrew his cock from my mouth and gave me a smile that seemed to me to almost say that we had broken new ground, but there was more to come.

Rather than wilt, Dave's cock stayed hard. Ann had him stand then Ann ordered me to stand. My legs seemed to be made of rubber, but I managed to get to my feet. Ann said,

"You know what's next, don't you, Sissy?"

My eyes darted from Dave to my ex wife Ann and back again. "He's going to put it up my ass, isn't he?"

Stepping forward, Ann smiled and answered, "That's right but we both know its your man pussy from now on."

She moved around behind me as Dave reached out and grabbed my still stiff five inch cock Ann then slid her fingers between my ass cheeks, puling it open and teasing around my sphincter, and rubbing inside my anus. Teasing me with her fingers, she began to coo in my ear,

"Tell Dave what you want, dear."

"I want you to fuck me in the ass please sir," I said, looking at Dave. I reached down to grip his cock firmly, tugging on it gently feeling the heat, stroking its length, grabbing its girth. "I want you to fuck me with your big thick dick please Sir, Mistress demands it!"

Ann removed her hand from my ass and had me get down on my back in the middle of the Bedroom floor. My head was spinning as Dave moved into position, half knelt between my legs. I raised my hips for him and he rubbed his cock head all over my ass, god it felt huge but I was trembling with excitement, I really wanted his cock inside me. I saw Ann produce a jar of what I supposed was lubricant from her bedside drawer, and instinctively, I pulled my knees up to my chest. She proceeded to lubricate my anus, first slipping one, then two fingers into me. By now, my cock was fully erect and achingly hard again swaying in front of my own face.

Ann swung around she quickly straddled my face, quickly squatting down she planted her sopping-wet pussy in my mouth. As I began to service her with my tongue, she grabbed my ankles and pulled my legs wide apart. A moment later, I felt the head of Dave's cock touch my asshole. While Ann had previously used butt plugs, and strap on dildos while fucking me in the ass, it was nothing like this. I could feel my ass being stretched open as Dave's hard as a rock nine inch cock burrowed inside me.

Dave began to rock back and forth, and soon his cock was slamming in and pulling back out in a steady rhythmic motion. I was moaning into my ex wife's pussy and then she began chanting, in time with his thrusts,

"Fuck the bitch, fuck her ass, fuck her ass, fuck the bitch," over and over again.

I have to admit that I was delirious to the point of experiencing a floating sensation, almost an out of body experience. It was brilliant I was tingling all over with pleasure. the fact that I had been forced into this position by my sexually demanding ex wife-mistress made it all that more exciting to me. Dave's thrusting shaft felt like it was inside my chest cavity, like it was splitting me apart, and I found myself desperately wanting him to fuck me harder.

Suddenly, and without warning, my body shuddered, I felt a huge wave of warmth flood over me and I had the most intense orgasm of my life, and as my spurting cock sprayed my own cum into the air, onto my chest, Ann scrambled off my face and caught some of my seed on her hand as Dave continued pounding into my ass.

Within seconds he was sweating profusely, calling me his little man whore, a faggot cock sucking bitch, a male cock slut I loved the filthy things he was calling me while ramming my ass like he was fucking a two bit whore (which I suppose I was really) then moments later, he yelled and grunted loudly and came.