A Game With My Keyholding Wife Goes Too Far

If anyone had been there to look through the french doors from the garden they would have seen a maid bent over the dining table, squirming and crying as the lady of the house reddened her little ass with a cane.
What they would not have been able to observe was just how special a moment this was between the maid and her mistress.
I could not have predicted the flood of emotions that came over us both as Michelle raised stripe after stripe under and around my girly french knickers. This was no longer punishment. I had surrendered to my darling wife at a deeper level than ever before. The caning was merely a demonstration of the connection we felt.
My mind raced with thoughts of all the things involved in having a baby. Was I ready for this? Would I ever be ready for this?
The idea of having Phil's baby seemed to cause no such concern or lack of certainty in Michelle. The moment my beating ended she ordered me to the bedroom. I lost track of the number of orgasms she had as I licked her unfaithful pussy. There was something primal that had been released in her that was exciting her to new heights of passion. I loved seeing her so aroused, even though I knew it was not my oral skills that had her screaming and crying as she bucked against my face. Rather it was the thought of her lover filling her womb with his potent seed, knocking her up right in front of her pathetic sissy husband.
When she finally calmed down my neck and jaw were sore. I curled at her feet, softly kissing them, telling her over and over how much I loved and worshipped her. The last thing she said before she fell soundly asleep was, 'I'm going to have a real man's baby'.
The next morning Michelle was straight onto her laptop looking at baby pictures. I couldn't help but feel a deep crippling cucky angst as I imagined my wife holding Phil's baby in her arms. We had another week before Phil was coming to visit us again and I consoled myself with the hope that she would come to her senses and change her mind by then.
The week passed quickly but things got worse rather than better. By the day of Phil's arrival Michelle was in a total baby craze. I was surprised though when she told me that she had not mentioned a word about her plans to Phil. She wanted me to be the one to ask him!
As he walked through the door I was dressed in a new uniform bought online by my wife. It was bright pink instead of the usual black, with extra ruffled petticoats and lots of bows. If I'd thought my previous uniform was feminine, this was made it look positively mild in comparison. The object of the exercise was very clear. My devious mistress wanted me to look as girly and sissy as possible to emphasise her need for a real man.
My calves ached from the new patent leather pink booties with six inch heels that Michelle had locked onto my feet. My curtsy was less graceful that usual owing to the six inch long chain joining my ankles. My mistress had decided to sissify even my walk by ******* me to take little baby steps teetering on those enormous heels. The whole ensemble was topped off with a long blonde wig and lots of makeup. With the arrival of my wife's lover there could be no possible doubt who was the man of the house.
It seemed that my loving wife could not wait to yet further deepen my *********** as she paused in her make out session with Phil. They were both stood just inside the front door, his hand grabbing her ass. She was wearing nothing but a pair of white hold up stockings and a short silk robe as she looked over at me, both her tiny hands grasping his muscular arm.
'Baby, our maid has something she would like to ask you,' she smiled.
Phil looked at me, his expression was not happy as he was clearly annoyed that the ravishing of his woman should be interrupted by a servant. I immediately felt myself blush bright red. Not for the first time I wondered why I always felt so incredibly weak and inferior around him.
Looking down at the floor, I nervously adjusted my new uniform. Where to start?
Michelle helped me out by pointing to the floor at Mr Phil's feet. I almost tripped and fell as the chain shortened my stride unexpectedly. I squirmed as I knelt there, looking up only briefly before cowering under the stare of my wife's chosen lover.
'Excuse me sir....err......Miche....I mean...my mistress.....well.....both of us have been thinking that...erm....we....I mean that it would be......'
I felt so weak, so nervous, so flustered, my mouth was dry, my lips wouldn't work.
I looked up at Michelle, one of her hands now brazenly rubbing at the bulge in Mr Phil's jeans. She smiled at me and I knew I couldn't refuse her. I loved her so much.
My eyes watered as I struggled to compose myself.
Mr Phil, sir, I would be honored if you would be willing to impregnate my mistress'.
Mr Phil looked at my wife who beamed up at him.
I went on, completing my shame, 'She has been off birth control since you left Sir. It's clear that she loves you and wants to have your baby. Please will you breed her Sir?'
Before I'd even finished, their lips were locked in a deep, passionate kiss. I stared at the floor feeling like the worthless pansy I knew I was.

The Ultimate - begging your wife's Bull to breed her, while you're in enf0rced chastity.

Watching Michelle spread her legs on what was once our marital bed brought a rush of overwhelming and contradictory emotions. She looked so beautiful, so perfectly gorgeous. Her long auburn hair cascaded across the white pillow, her tanned thighs where held so willingly up in the air, begging to have a strong man hold her down and give her a baby.
Part of me knew this was right, it was how it was supposed to be. But another part of me wanted desperately to be the one on top of her, thrusting deep into that soft fertile pussy.
It was as well that I was already on my knees at the side of the bed where my mistress had placed me. I would have dropped to them anyway with the pa1n afforded to my poor sissy clit by the infernal chastity tube spikes. I had thought such pa1n behind me as my wife's remorseless training took its effect and my cock ceased to grow. But I had not bargained for such extreme provocation as this. Seeing my darling wife, my closest friend, my soul mate, in the arms of another man, begging him to give her his baby.
Looking down between my legs I tried to remember what it felt like to be inside a woman. Our chastity games had been a regular feature of our lives for many years over which vanilla sex had declined and eventually died. I wished with all my heart that I had paid more attention the last time I made love to Michelle. Especially since it was now looking like a very real possibility that I would never have the opportunity to do so again.
Looking back to the bed I was struck pa1nfully by the evidence before me. Mr Phil and my wife were staring into each other's eyes, then mashing lips together, tongues probing, hands exploring. Michelle was like a bitch in heat, nibbling and licking her lover, lifting her hips from the bed begging to be fucked. Wrapping her legs around Phil's waist and her arms around his neck she pleaded for his huge cock.
Phil grinned at her, savouring his prize, laughing at my wife's heart felt entreaties. I was ready to beg him to fuck her myself by the time he finally entered her. It was so hard for me to watch another man take the ultimate prize. He had done nothing to win her, he did not deserve her. She was so beautiful, so precious! Did he even love her? She deserved to be loved by the man who would ****** her baby.
Perhaps my wife was thinking the same thing because she chose that moment, locked together with her man, his huge cock buried inside her womb, to cry out to him, 'I love you, fuck me, fuck me my darling. Put a kid in my belly!' Oh darling I love you. Do you love me? Say it. Say it please! Fuck me and say you love me!'
With my wife and mistress pinned helplessly beneath him, Mr Phil, my master and superior in every way, began to slowly work his manly hips. His huge rod glistened with Michelle's juices as it withdrew before plunging back in. She was in the throws of her first orgasm of the night when Mr Phil finally replied, 'Of course I love you. You are mine, you belong to me. I'm going to fuck a baby into your hot married pussy and I'm going to do it right in front of your sissy faggot husband'.
'Oh fuck, yes, yes my darling, do it! Let him see how we love each other. Make him watch as you put a kid in his wife,' Michelle moaned.
'Tell him then,' ordered Mr Phil. 'Tell that ponce over there what you want, what you need. Fucking tell him or I'll pull out now!'
'I'm sorry baby,' my wife apologised, turning her head to look at me. 'I can't help it. I'm in love with Phil, I want him so much. I love him. I live to have him inside me. I'm going to have his baby'.
I'd intended to be brave, I'd tried so hard. But my wife's cruel admission was too much and I burst into girly tears. I cried as my wife came again screaming her lover's name. I continued crying as Mr Phil emptied his huge balls into the woman I loved. It was done. There was no going back now.

It must have felt amazing for Mr Phil as he relaxed beside my unfaithful wife, her head nestled into his barrel chest. He had utterly conquered our marriage. I had been soundly and irreversibly cuckolded.
I knelt there at the side of the bed that now undeniably belonged to my mistress and her lover, watching with tear filled eyes as Mr Phil's thick white sticky cum dribbled slowly from my precious wife's unprotected pussy. Phil's cock was still draped over Michelle's upper thigh and his hand rested firmly above her hip. It was a clear picture of ownership that broke my heart but still hardened my poor imprisoned little cock. Then the spikes bit in and it deflated once more. I wasn't even allowed an erection much less an orgasm. Erections and orgasms were for real men. Men like Mr Phil. Not sissy maids like me.
Eventually Mr Phil got up from the bed and walked over to me, his still large but now soft cock swinging and dripping his and my wife's juices as he approached.
'No free shows here pansy,' he announced. 'You have to earn your keep in my house'.
His house? Well why not, he'd taken everything else from me.
'Open wide faggot,' Mr Phil instructed. 'The only reasons for having a maid in my bedroom are to either make the bed or clean my cock. Guess which one you get to do right now'.
I was super concious of my wife's amused gaze as I took Mr Phil's slippery weapon into my warm sissy mouth. I imagined all of his sperm swimming inside my wife as I felt my own little balls flop uselessly between my thighs.
'Good girl,' I heard Michelle reward me. 'You have to let go baby. Forget any silly ideas about being my husband or even about being a man. Phil is a man baby. You are a sissy maid, nothing more. Just keep that in mind and you'll be fine. You have nothing to worry about. I love you and I'll never leave you but you have to submit to Mr Phil. I want you to grow to love him as I do. I want you to worship the ground he walks on. But I want you to fear him too. That's what turns me on most of all, I want you to be terrified of my lover'.
'Don't worry,' laughed Mr Phil. 'If he isn't he soon will be. Won't you faggot?' he asked slapping my face hard causing my mouth to fall away from his rapidly hardening cock.
'Look what your useless fucking maid did now Michelle,' he shouted, pointing at his tumescent organ.
'Well don't waste it baby, laughed my wife. 'Get over here!'
'Get on all fours,' Mr Phil ordered my wife. Then, smacking her ass he prepared to mount her from behind like a bitch.
Mr Phil was going to be sure to breed my wife properly.

Thanks to kennyboy82 for his interest. I have to admit, I'm otherwise a bit disappointed at the apparent lack of interest in my story. Very few comments. Does nobody read the stories on here any more? Come on guys, let me know what you think!

We're reading, but it's hard to write back with only one hand.

Your story has about 5000 views in about 13 days, so it's getting about 400 views a day on average. That's a hell of a lot of readers. I know it's one of my favorites, so others must be liking it, too.

Please keep up the good work,
hando
Natural Born Cuckold
Pussy-Free For Life starting 02-26-2017, 2633 days as of 05-13-2024

Just discovered this--got some catching up to do. Welcome to my Favorites folder!

One of the best ever !!!! Thank you !!!!! Pls.continue....

Wonderful!
Loving Wife, Mother, and Bryan's Slut

The whole baby making affair made Michelle hornier than I'd ever seen her. She was completely infatuated with her lover. It was heart breaking for me to see them together. They could not keep their hands off each other. I'm not sure which was worse, walking in on them fucking each other's brains out in every room of the house, or catching them kissing softly and lovingly, staring deeply into each other's eyes when they rested between sessions.
Michelle was insatiable. Even though her lover was taking her three, sometimes four times a day, as soon as he went out anywhere Michelle would ring the bell summoning me to her presence. Without a word I would kneel between her legs and get to work pleasing her with my tongue. Michelle would cum again and again, writhing against my extended sissy tongue. I couldn't help but be turned on by my wife's humiliating use of me. I was no more than a vibrator, a sex toy, to be used whenever real cock was not immediately available.
My mistress seemed to revel in her treatment of me. If she wasn't singing her lover's praises she was demeaning me and my lack of manhood. It hurt so much and yet it also drove me wild with lust for her. I would go to ***** every night, my poor sissy bottom red and stinging from my nightly beating, my balls aching from both pent up frustration and the painful swats Mr Phil had taken to giving them with a wooden ruler as an addition to my nightly punishments. Then I would dream of my lust fuelled spouse, imagining what it would be like to take her, to sink my manhood balls deep into her unfaithful pussy just like Mr Phil did. Sometimes my dreams would result in a small emission, my only release, but my caged clitty had given up trying to get hard. The thought that this might be permanent, that the cruel, spike filled tube may have rendered me permanently impotent filled me with dread.
One day, after my devoted tongue had succeeded in bringing my demanding mistress to three orgasms, I risked informing her of my concern.
'Sweetheart,' she soothed, stroking my hair as I knelt between my legs. 'We've come so far so quickly. You were a very masculine man, now you're more or less a girl. You were a successful business man in charge of many others, hiring, disciplining and firing as you chose. Now look at you. You're a sissy maid desperate to do anything, face any hum1liation, just to please your mistress. There was a time you could have sex whenever you felt like it, cumming at will. Now you don't know if you'll ever be allowed a hard-on again, much less an orgasm'.
'Yes ma'am, but I'm really trying hard to please you and Mr Phil in the hope that I might be allowed to cum soon. It's all I think about. I can't stand it. Seeing you looking so beautiful, so sexy and not being able to do anything about it is killing me'.
'But you can do something about it you silly girl, you can pleasure me like you just did. You can forget about your orgasms and focus on mine. You can gain sexual fulfilment through me, your mistress'.
'Please ma'am, I love giving you pleasure but I'm afraid. When will I ever be able to take off this damn cage? Will I still be able to get hard?' I pleaded.
'You mean will you still be a man?' Michelle queried.
'I suppose so,' I answered, realising the stupidity of my question.
'Listen to me sissy, you asked for this. You dreamed of it and fantasised about it for years. I know you did so don't deny it. Because I love you so much I've gone to considerable trouble to make it a reality for you. Is it wrong that I should enjoy it too? Isn't that what you really craved? For me to cuckold you, sissify you, hum1liate and frustrate you, but for my enjoyment not yours. That was your ultimate fantasy wasn't it?' my mistress demanded.
'I suppose so, yes but......'
'Go fetch me a cane right now!' Michelle screamed. 'I am not doing this. You are a fucking maid. You will deal with whatever I or my lover throw at you and you will do it with a smile on your face or, so help me, I will beat you till you fucking do!'
I retrieved the cane and returned as quickly as the stupid ankle chain and ridiculous high heels would allow me to. Michelle was still sitting in her armchair. She pointed at her ass. I handed her the cane before kneeling to begin my gentle slow worship of her little ass-hole.
'Good girl sissy,' my mistress praised me as she pulled me deeper between her ass cheeks.'You will learn I promise you'.
The swish of the cane and its sting to my poor exposed sissy ass was accompanied by my wife's cruel laughter.
'Oh yes, you will learn slut. If I have to beat you *********** every day of your miserable life, you are going to learn'.
I couldn't answer with my lips locked to my mistress's ass-hole and my tongue buried inside its salty cavern. I could only lick harder and deeper hoping to show her that I loved her, that I would do anything for her, no matter the cost to me. She was my mistress, my owner. I was her slave to do with as she pleased. My life meant nothing now outside of its convenience to my mistress. She was right. This was what I'd always dreamed of.

It had been a long day, trying not to focus on the thought of Mr Phil's sperm swimming around inside my fertile wife. I was feeling tired and confused as I worked on my knees, waxing the kitchen floor.
I was startled by the sound of the doorbell and my mistress shouting to me, 'Go answer the door sissy, what do we keep you around for? Jump to it maid!'
I dreaded answering the door. Whoever it was would see me in my make-up, stockings and maid uniform. A stranger would be bad enough but what if it was someone I knew.
Fortunately I didn't recognise the lady stood on the doorstep or the gentleman standing behind her. I had no idea what to say so just stood there red faced until Mr Phil came up behind me.
'Carrie, how are you,' he cried. 'Let them in you stupid slut,' he admonished me.
The woman Carrie looked me up and down as she stepped past me, obviously trying not to laugh. The man, her husband I presumed, was right behind her. I couldn't look at him, keeping my eyes down as I curtsied politely and wished I could become invisible.
'I'm sorry about my maid,' Mr Phil apologise, 'We're still training her'.
I took the ladies coat and stood transfixed at her beauty. Probably about ten years younger than my wife, tall and slim with long blonde hair, she looked gorgeous.
'Bring us some wine,' Mr Phil snapped at me before ushering the guests into the lounge.
Entering with a tray I noticed that Carries husband had not taken a seat but was stood meekly behind his wife's chair. He wasn't chuckling at my sissy gait as I'd expected. In fact he looked as nervous as I felt.
I was shocked when Mr Phil sat and invited Carrie onto his lap. She smiled at my wife before giving Mr Phil a deep snog. I looked over at Carrie's husband to see him turning bright red.
Mr Phil moved Carrie to one knee, holding out his hand to Michelle. She joined him and sat on his other knee.
'Wine for the ladies and me sissy. Prissy isn't allowed,' Mr Phil instructed me as he sat there, a beautiful woman on each knee, master of all he surveyed.
I felt sorry for Prissy as I realised he was a cuckolded sissy husband just like me.
'I think he's a little over dressed to isn't he?' Mr Phil asked Carrie.
'Yes he is darling,' she smiled. 'Prissy, get you bag from the car, change in the hallway and get back here. Quickly!'
I hardly recognised Prissy when she came back. Her hair and make-up were perfect if a little heavy. Her legs were gorgeous in their white nylon stockings and her yellow silk dress looked like it was designed for a little girl.
'Show Mr Phil your new cage Prissy,' instructed Carrie.
Once again red faced, Prissy lifted the front of her dress revealing a stainless steel chastity tube.

Prissy and I were instructed by Mr Phil to kneel side by side to one side of his armchair. The ladies had moved to the couch where they chatted excitedly. It seemed that Michelle and I were not the first couple that Mr Phil had 'owned'. Apparently he had discussed a get together with my wife and she had agreed it would be interesting. Carrie was obviously aware of my wife's plan to have Phil's baby and she was full of admiration and envy. Michelle seemed to revel in having another wife/mistress to compare notes with. Mr Phil smiled smugly as his women talked, enjoying the company of his bitches as their defeated husbands knelt nearby awaiting his orders like the little pussies we were.
Then, suddenly, one of my ultimate fantasies became real. Michelle and Carrie rose and escorted Mr Phil to the master bedroom, starting to strip off their clothes as they went. Prissy and I were told to crawl behind like well behaved pets.
I wondered if Prissy was filled with the same horrible jealousy and envy I was feeling as our wives knelt together over Mr Phil on the large bed. They were both down to their panties as they joined ****** to pull off his jeans. I thought I would scream in heart-wrenching jealousy as they took turns wrapping their gorgeous painted lips around his huge cock and nibbling his enormous balls.
I noticed that there was a puddle developing on the floor under Prissy's locked clitty. I could see that her poor little shaft was squeezing hard against its tight little cage as she watched the show our wives were putting on. I wondered how long it would be before the poor fool was fitted with a spiked cage like mine, ending the privileged of getting hard.
I would have given just about anything to be Mr Phil as Carrie gently eased herself onto his big cock. My wife was caressing her hair and nibbling her ear as her new friend groaned her appreciation.
I had grown almost accustomed to the angst that accompanied seeing my wife making passionate love with another man. Prissy, however, wasn't taking it so well. Little tears formed in the corners of her eyes as her wife took the full length of Mr Phil's big shaft, moaning and obviously lost in ecstasy. I wished there was some way I could comfort my fellow sissy.
When Carrie started rocking her hips and begging Mr Phil to give her a baby too, Prissy lost it. With a red teary face, she jumped up and tried to interrupt the passionate lovemaking. It was a big mistake.
As she reached the bed blabbering incoherently, Mr Phil grabbed her arm and gave it a vicious twist. In an instant the unfortunate sissy was turned around, her arm held m4rcilessly in a stronger man's grip. Carrie looked very angry as she dismounted her lover.
Mr Phil held Prissy in place with one hand while, with the other he began whacking her ass. The sound was horrific. Prissy cried and sobbed trying without success to escape.
Eventually Mr Phil paused, 'Ready to behave Prissy?' he asked.
Prissy just sobbed in abject defeat. Mr Phil started whacking her ass again.
'Speak up, cunt!' he yelled.
Prissy sobbed in a defeated tone I was all too familiar with, 'Yes Sir, I'll behave'.
With that Mr Phil shoved the poor pansy back on the floor. She sniffed back her tears and knelt back beside me, sore and broken. I was sure there would be further consequences later.
Both of our wives were rubbing themselves, masturbating openly. There was obviously something primal and deeply erotic about watching a strong man crush a weak excuse for one like that. I was just grateful that, for once, it wasn't me.
A few hours later Prissy and I found ourselves in the lounge, kneeling at Mr Phil's feet as he enjoyed the afterglow of breeding our wives. Michelle and Carrie sat on either side of him on the couch, caressing him and looking at each other occasionally like silly schoolgirls with a crush on the captain of the football team.
Mr Phil spoke to us in a firm tone, 'Prissy, your behaviour in there was completely unacceptable'.
I glanced at my sister sissy. She seemed genuinely contrite.
'Sissy, you were a good girl,' he praised me, 'but you should have stopped your silly sister from trying to interrupt me'.
'Yes sir,' I responded quietly.
'Until further notice neither of you is allowed to speak a single word,' our master declared. 'Your silly lips are to stay shut, so your betters will not be interrupted by the stupid things you have to say. Nobody wants to hear the nonsense you little cunts are thinking anyway'.
We both knew better than to protest. I nodded dumbly as Prissy mumbled her assent.
'Good girls, smiled Mr Phil, leaning back on the couch, putting his hands behind his head. 'Now worship your master's cock faggots'.
Prissy and I glanced at each other before obediently shuffling forward and bending to our task. I could here our wives giggling as we dutifully applied our sissy lips and tongues to the cock and balls of the man who had bred both our wives.

I was sure Mr Phil had not finished punishing my sister and I for her rude behavior and my failure to stop her. I glanced up from my dutiful work to see him looking at us, an evil smile on his face. Michelle and Carrie would have been enough to ********** any man. They rested on either side of Mr Phil, their legs partially over him as they nibbled playfully at him and fought for his attention. I had a view of Carrie's thighs that was driving me insane. I tried not to think about the fact that I would never in my life get to experience a night like Mr Phil was having.
Mr Phil slapped the tops of our heads, 'Okay little losers, I'm ready for some entertainment.'
'I think it's time my little pansies got to know each other a little better, don't you ladies?' Mr Phil asked.
Prissy and I had watched our wives bred by our master together and then spent some quality time worshiping his cock. How much better could we know each other I wondered.
'What do you have in mind,' Michelle asked him.
'Well, since it's just their first date,' he answered, circling my wife's nipple with his finger, 'How about they start with some kissing?'
Michelle and Carrie cheered, clearly enjoying themselves at our expense. I didn't look at Prissy. I couldn't.
Mr Phil leaned forward, 'Okay little faggots, here's how its going to work. Whichever one of you puts on a better show gets to cum soon. The other one stays locked up for three more months'.
'Wow, sissy,' my smirking wife laughed, ' You've already been locked up for about three months haven't you? Another three months should be a breeze. Besides, your little clitty doesn't work anymore anyway does it? Maybe you should be a gentleman, or should I say a lady, and let Prissy win'.
'Oh no,' joined in Carrie, 'It was Prissy who misbehaved, I think it's only fair she should be punished. Besides, she had a ruined orgasm six weeks ago. I don't want to spoil her'.
They both laughed. I trembled. No way could I take another three months and I was sure Prissy would feel the same way.
Mr Phil chuckled seeing the internal struggle written across my face. 'Right, get to it faggots. I want to see you make out like it's prom night. Don't stop until I tell you to'.
Prissy and I knelt awkwardly, each frozen by our horrible predicament. I wondered if the thought of kissing another man was as repugnant to him as it was to me.
Our wives started clapping in rhythm, egging us on. I thought about the possibility of being allowed to cum and turned, edging closer to my fellow sissy. Prissy copied me, a horrified look on her face.
Michelle and Carrie cheered as our lips met. I tasted Prissy's lipstick, it was cherry. I stupidly wondered if she could taste my own strawberry lip gloss, a gift from my mistress wife.
'Who wants to cum?' asked Mr Phil, leaning back and sliding his arms around our wives.
I closed my eyes and parted my lips giving my fellow sissy a full kiss. I jumped as I felt his tongue reach out and touch the edge of my mouth. The competition had begun.
Our hum1liation was thorough and unrelenting as our clits dripped through their cages, desperate for the chance of release. Our tongues explored each other's mouths, our lips locked as we made out like a couple of nervous, lovestruck teenagers.
Hoping to score extra points I reached up and stroked the back of Prissy's head with my fingers as we kissed. Not wishing to be beaten Prissy slowly reached her own hand around to fondle my ass. Our bodies touched and we writhed together. Gripping my ass in both hands now, Prissy pulled me tighter to her, ******* her tongue still deeper into my mouth as her soft lips crushed mine aggressively. In the heat of the moment I was deeply embarrassed to find myself rubbing my locked clit against her, wishing I could feel something, even the pinch of the pins I'd formerly learned to dread.
The sound of Mr Phil telling us to stop was accompanied by happy cheering and applause from our wives. They had obviously enjoyed the show. I stared at the floor, unable to believe what I had just done. With the taste of Prissy's cherry flavored lips lingering on my tongue I realised that what Mr Phil had made us do was much worse than a whipping could ever have been.

Mr Phil announced that a vote was to be taken to decide which of us sissy maids should be granted an opportunity to gain some slight relief from the t0rture of permanent chastity, the other being sentenced to a further three months of abstinence.
Michelle had first vote and, to my shame, voted for Prissy. Carrie, showing similar cruelty toward her maid, voted for me. That left Mr Phil with the deciding vote.
After some deliberation accompanied by much giggling from the ladies, Mr Phil decided he needed more evidence on which to make a decision. To mine and Prissy's utter horror he had us lie on our sides in front of the couch, in head to tail position, each of our faces in line with the other's caged clitty.
'Right faggots,' Mr Phil announced, 'Let's see which one of you pansies really wants to cum. The winner will be the one that shows the most enthusiasm for sucking the other's tiny little cock. I know the chastity cages are in the way but that's just tough. I expect you to improvise. Now get busy'.
Staring at Prissy's hairless groin I broke into a cold sweat. I couldn't do this, no way!
'If you need some encouragement,' offered Mr Phil, 'Think about how long three months is going to feel. And that's assuming your behaviour is perfect for the whole of that time. I have no problem with adding even more time if I'm not entirely satisfied with your work or your attitude'.
The threat must have been too much for Prissy as he jumped into action, shuffling closer and darting out his tongue to lick the shiny stainless steel walls of my cage.
'That's Prissy in the lead I reckon,' laughed Mr Phil.
Desperate not to have to deal with the unimaginable consequences of loosing this absurd competition, I immediately reached forward with my head, opening my mouth to engulf Prissy's metal cock tube.
Shouts from our unfaithful mistresses of 'Sixty nine, sixty nine,' filled our ears as shame filled our hearts. Poor Prissy's little cock was pressing futilely against the walls of its prison, the head trying to poke out of the drainage slit at the end. S1ckened but determined to end my chaste m1sery, I worked my tongue into the slit, tasting Prissy's precum.
Prissy must have been equally desperate but found she could not make contact with my little clitty. The spikes had done their job, rendering me impotent, or perhaps it was the shear em8arrassment of what I was doing. Presumably seeking to gain back the advantage Prissy switched her attention to my aching balls. Her kisses and licks soon had me groaning in shear frustration. It had been so long, I could not possibly contemplate another three months of denial. I had to do something, anything to gain some relief.
Quickly I wrapped my arms around my fellow sissy's waist, switching my oral skills to her hairless little balls I sucked one then the other into my warm wet mouth. I heard her sigh and felt her tense as I wormed an index finger into her tight puckered asshole. The cheers of our cold hearted spouses filled my ears as Prissy's twitching cocklet dribbled her sissy slime onto the floor. In a final attempt to secure victory I spat out her balls and bent to lick up her mess from the carpet.
I felt a curious pride as I knelt beside Prissy awaiting our master's favour. Surely I'd done enough. I'd deba8ed myself more thoroughly than I would ever have dreamed possible, 'Please,' I hoped, 'Don't let it be for nothing!'
'Well, well my little pansy faggots,' declared Mr Phil, 'It seems we might make passable sissy maids out of you yet. After that display of rampant sissy sex I don't think there's any possibility either of you will ever be taken for anything but the pathetic desperate faggots you are'.
I glanced across at Prissy to see what effect our activities, her release and Mr Phil's comments had had on her. She looked lost, confused, like she couldn't believe what had just happened.
'Sissy, I am especially impressed with you. I knew you were a pathetic little cunt but I had no idea you were such a cock sucking little pansy. You really are a proper cock slut aren't you?'
'Yes sir,' I mumbled. The pride I'd felt had vanished at his words to be replaced by a deep loath1ng for myself and how I'd behaved.
'Speak up faggot,' ordered Mr Phil. Tell you mistress what you are'.
I could not look Michelle in the face so staring at the carpet in front of me I made my embarrassing admission. 'Please ma'am, I'm a pathetic little cock slut'.
'Tell her why sissy,' Mr Phil pushed.
'Because ..... I ...... please ma'am, I like to suck cocks,' I finally admitted to my wife of more than twenty years.
'We know,' laughed Michelle, 'I videoed the whole thing on my phone in case I need to remind myself what my big strong husband has become'.
'Send me a copy of that,' Mr Phil instructed my mistress. 'It will be excellent insurance against either of these losers deciding to cause us any problems'.
'Ok darling,' smiled my treacherous spouse.
'Now then,' Mr Phil continued, 'I think I have enough information to make my decision. Sissy, you won'.
'Yeahhhhh,' cheered my wife, clapping her hands. 'My maid is the biggest sissy!'
Hearing my darling wife demonstrate her pride in my deba5ement was the final straw and the tears flowed as I sobbed. What had I become.
'Oh, don't cry sissy,' soothed my mistress. 'I'm proud of my maid's cock sucking abilities. I'm sure Mr Phil will have plans to make good use of them. Now cheer up. Think about poor Prissy. What does she have to look forward to now?'
'What she has to look forward to is three months chastity,' declared Mr Phil. 'Followed by a further three months. Six months in total faggot!'
Sissy's gaze had been fixed on the floor in front of her but Mr Phil's words clearly shocked her as she lifted her head, mouth open in shock.
'Don't look at me like that you little cunt,' yelled Mr Phil. 'You had an unauthorised orgasm. Well, what passes for an orgasm for you anyway. You can think yourself lucky I'm feeling generous. I could have made it a year'.
In clear desperation Prissy turned her pleading eyes to her mistress.
'It's no good looking at me Prissy,' Carrie declared. 'Mr Phil's word is law, you know that don't you?'
Prissy had begun to sob, her shoulders heaving.
'Now come on Prissy,' her mistress admonished. 'Maybe if you'd been wearing a spiked tube like your little friend this wouldn't have happened. As it did you'll just have to deal with it. We'll order you a new spiked cage when we get home. Then maybe you won't embarrass me or yourself by being so silly in future'.

'Right,' Mr Phil announced, looking at his watch. 'Almost bed time for these two faggots. First of all though, I think a little gratitude is in order. Stand up girls'.
Our wives stood and Prissy and I, tears mixing with mascara and running down our faces, positioned ourselves as instructed by our master. We both sat, backs to the sofa, heads laid back on the seats recently occupied by our wives.
'Ok girls,' Mr Phil smiled. 'A little treat for you. Sit'.
My head was squashed into the soft leather sofa as Michelle's warm wet pussy descended over my face. Mr Phil's cum coated my tongue as I ****** it between the lips of her pussy. At least this was better than being ****** to suck another man's cock, I thought.
Mr Phil remained seated between Prissy and I slapping the asses of his bitches and encouraging them to 'Ride those fucking faggots!'
Michelle and Carrie must have been really turned on by the earlier antics of Prissy and I because they both came quickly and almost together.
The air felt delightfully cool on my hot slimy face as Michelle stood but my relief was short lived.
'Ok, swap,' instructed Mr Phil.
It took longer this time to make the ladies cum. My neck ached by the time they did. Carrie had clamped herself down onto my nose and lips so hard I had been completely unable to breathe. I didn't dare raise any objection or try to move her in fear of Mr Phil cancelling my blessed promised relief. So by the time she finally lifted off me I was on the verge of passing out.
'My turn now,' Mr Phil announced to mine and Prissy's horror. 'You stay there,' he instructed Prissy before reaching back to pull his ass cheeks apart and seat himself heavily onto poor Prissy's bright red face.
I could have cried for poor Prissy's predicament until I heard what Mr Phil required of me. 'Right sissy, get over here and show me what you did to little Prissy that got her so excited'.
Would the hum1liation never end, I wondered. All I wanted was to be able to cum. I'd waited so long, put up with so much.
'Hurry up sissy,' urged my wife. 'Or do you want your master to cancel the release you earned sucking Prissy's little balls?'
Bending to my task I steeled myself and went to work on my master's huge hairy balls.
'Get that fucking tongue deeper in my ass faggot,' he yelled at poor Prissy. 'Or shall I change my mind and make it a year before you get another chance to dribble?'

I was spared a mouthful of Mr Phil's potent jism when Michelle and Carrie complained to him that he should not waste it on a sissy.
'Right, bed time for faggots then,' he announced. Ceasing my devoted ministrations to the cock and balls of my master I rose and went to retrieve the cane and ruler that were my regular reward for a days servitude. When I knelt to offer them to Mr Phil he rose from poor Prissy's face and announced a change to the usual routine in recognition of the presence of guests.
'Michelle would you get the parcel that arrived for me today please?' Mr Phil requested. 'Bring it to the bedroom. You two faggots, I want you stripped to underwear and standing to attention beside my bed. Move!'
Slowed by my six inch heels and the short chain between my ankles I arrived in the bedroom last. The mistresses were lounging against the bed's headboard, shameless in their nakedness. But, then again, they was only one real man in the room and he was lover to them both. It was Prissy and I who felt shame, standing as we were, grown men dressed in girly underwear, bra, panties and stockings. Neither of us knew what was coming but we both knew it would be nothing good. For my part I was wondering if I dared ask about my promised reward of being allowed to finally spill my long overdue seed.
In the end I did not get the opportunity. Mr Phil had us both dancing once more to his own cruel perverted tune. 'Turn and face each other,' he commanded. 'Now put your arms around each other's waist'. Neither of us could meet the eyes of the other as Mr Phil took two sets of handcuffs from the parcel he'd sent my wife to fetch and snapped them shut around our wrists. Next he produced a padlock and used it to lock our chastity tubes together.
I watched in horrified fascination as Mr Phil then pressed a penis gag into Prissy's mouth. This item was obviously purpose made for just such a situation as it had another black rubber penis sticking out from it. Straps were secured around Prissy's head then I was instructed to take the protruding phallus into my mouth so that the remaining straps could be fastened around my head.
'You'll be pleased to know they're inflatable too,' announced Mr Phil happily. Just a few pumps had Prissy's cheeks bulging and her eyes wide in panic. I was next and fully understood how Prissy felt.
Then it was the turn of our knees and ankles to be tightly bound with straps.
So there we were, two sissy maids in their underwear, fastened together at mouth and clit, unable to move in any direction, staring into each others wide open eyes in renewed panic at what our master might have intended for us.
The final item Mr Phil retrieved from his parcel was a large black leather drawstring bag. This he placed over our heads and drew tight around our necks condemning us to the darkness together. I could feel the warm air on my face from Prissy's accelerated breathing and it soon became quite hard to breath under that hood.
My attention was suddenly on other things as I felt the ever present plug being withdrawn from my ass hole. I'd grown used to it being there so I felt a mixture of relief and emptiness at its loss. That did not last long as I felt another plug take its place. I knew Prissy was being subject to the same treatment when we both squirmed and squealed through our gags as air was pumped into the plugs stretching my ass like never before. It must have been our mistresses who treated us to this singularly humiliating experience because Mr Phil's voice came from across the room.
'You'll thank me for that later sissy,' he laughed, 'When you find out what's involved in your bravely won opportunity to dribble your worthless slime'.
I couldn't see Prissy's face in the darkness under the hood but I was sure it must he sweating like mine. We both shuffled our bodies as much as possible, which wasn't much, already feeling very uncomfortable.
'I suggest you two pansies try to get some rest,' sneered Mr Phil, 'Try to ignore the noise these two sluts are going to be making soon. They're both going to get fucked. I'll do their mouths first, that should keep the noise down. Can't say the same for when I fuck those married pussies though I'm afraid. Oh, and I believe they're both anal virgins, so the noise levels are really going to rise when I get my cock up there. They're going to wish they'd had your opportunity to get stretched with a plug first, ha, ha!' the bastard laughed.
I knew then that my life as Michell's husband was over, permanently. Not to mention my life as a man. I was exactly what Mr Phil wanted me to be. A helplessly weak, impotent little sissy faggot, hugging another worthless pansy, crying to each other as we fought for breath in our hot sticky prison. Unable to move or escape the coming sounds of copulation as a real man showed our wives what they had been missing throughout their married lives.
'Oh by the way, I haven't forgotten about you maintenance beating. While I'm busy with one of your mistresses the other one will be caning you two. Pleasant dreams faggots,' Mr Phil laughed.

blue179
So you were the author of that great story that appeared on Tumblr a couple of years ago (New Man of the House) and its sequels (Sissy Sisters and The In-laws)! I might have known!

Please, keep up the good work!

The next few hours were a living hell. The high heels were killing my feet. My legs ached from standing in one place for so long. Both my mouth and my ass felt stuffed to bursting point. It was hot and sweaty inside the leather hood and a constant battle to try to draw in enough oxygen to keep from passing out. Then there was the cane. Neither Prissy nor I had any way to tell who would feel its sting next. Only when one of us felt the other tense and heard them scream around their rubber gag did we know where the stroke had landed. The relief of being spared was spoiled by the definite possibility that it would probably be me next. There were several occasions when I had to hold Prissy up as her legs gave way. More than once she returned the favour.
When finally the beating stopped Prissy and I stood shivering in panic and exhaustion, gasping for air. It was a major relief when the hood was removed. Finally, we could breathe!
Our legs were untied and, to our massive relief, the butt plugs were deflated and removed. We were instructed by our mistresses to shuffle together out of the bedroom and down the hall. We must have made a truly ridiculous spectacle, still joined face to face by our cock gags, still padlocked together by our chastity tubes, arms around each others waists with wrists handcuffed together.
Into the spare bedroom we were guided where our wives helped us to lay down on the bed. Prissy's face was a mess of tears and mascara, red lipstick smeared , drool running down her chin. I could only imagine what I looked like.
We were both desperately tired but, it seemed there was one final t0rment to be 5uffered. I watched as Carrie laid down behind Prissy and I felt Michelle shuffling into place behind me. At first I thought that my ass was being filled once more by the but-plug but as my mistresse's arms went around me and she pulled my hips toward her I realised she had donned a cock harness and was proceeding to anally **** me.
I saw Prissy's eyes widen in shock as he was subjected to the same treatment by Carrie.
'Sissy and Prissy's turn to get fucked now,' Michelle whispered in my ear as she began thrusting into me. It was pa1nful at first but soon the sensation began to change to one of pleasure.
'Look at your little sissy friend,' Michelle instructed, 'I think she likes getting fucked almost as much as you do, doesn't she?' It was true. Her face was red, eyes closed, breath hissing through her nose in time with her mistress's thrusts.
'Tell her you love her sissy,' my wife urged. 'Go ahead, hold her tight and tell her. Or shall we stand you up again and put you both back in the hood?'
'Ummmphh,' I gasped. The sensation in my ass was building, spreading through my whole body as my mistress's latex cock rubbed against my prostate. Was this to be my opportunity to cum? Desperately I hoped so. Michelle deflated my gag slightly to allow me to at least attempt to speak.
'Aaagh, uuuvvvv uuuuu iiiiyyy' I gasped.
'Oh how cute,' laughed Carrie. 'Can you hear that Prissy? Answer your girlfriend then. Tell her you love her too'.
I think we would both have said absolutely anything right then. We'd been broken and we knew it. Reduced to the pathetic, sissy pansies we were by the combined efforts of our wives and their mutual lover whom I could hear laughing as he stood in the bedroom doorway witnessing the final d4gradation of the night for his sissy maids.
I didn't care. I didn't care about anything but the massive orgasm I could feel building inside me. I was high, completely *********** with hum1liation, frustration and abject defeat. I was nothing but a pathetic sissy maid. A joke. A convenience for my mistress. An amusement for her and her lover. I was all that and I loved it. I was going to cum....
'Alright, that's enough,' shouted Mr Phil. Let's leave these two love-birds to get some rest. They'll need it. Tomorrow we'll drop sissy off at George's place then the rest of us will go to Carrie's place. I think Prissy will benefit from an intensive session serving the three of us for a week'.
My pleasure vanished as Michelle withdrew her latex cock from my ass. I felt empty, deflated, lost. I had been so close! The emotions became too much as Michelle threw a duvet over Prissy and I and kissed my cheek.
****** tight sissy maid,' she whispered. 'I'm so proud of you'.
I burst into fresh tears. These were not tears of pa1n though. These were tears of frustration, of longing, for the wife and the life I'd lost. Prissy tried her best to comfort me, even though she was crying herself. Eventually we cried ourselves to ***** locked together, wrapped in each other's arms.

It keeps getting better and better. Brilliant work

Bravo !!!! and Thank you......

Next morning we were up early and excused duties to get ready. I had to pack for a week (sissy clothes only), wash, shave/depilate, dress in full maids uniform with stockings and heels, apply full make-up and wig. I rode in the back of the car with Carrie and Prissy. Mr Phil drove my car with my wife sat beside him, her hand on his thigh possessively. After about an hour of sitting there exposed to any other motorists who cared to look through my window, I was relieved but nervous when we pulled up outside a detached house. I was told to get out and collect my suitcase from the boot.
Michelle got out too and came round to the rear of the car. 'Now remember sweetheart, you are my maid now, so your behaviour reflects on me. I want you to be a good girl for George, ok?'
'Please ma'am,' I asked, 'What's happening, I don't understand, who's George'.
'So many questions!' my mistress complained. 'Are you forgetting your place already?'
'No ma'am, of course not. It's just that...'
'Right that's enough. You are my property. I have chosen to make you Mr Phil's property too. He in turn has decided to loan you out to a friend. A very special friend. George, or Mr George to you I suppose, has a lot of experience training sissy maids like you. Phil and I both thought you would benefit from spending a week under his instruction. It will make you a better maid I'm sure. You do want to be a better maid for me don't you? Or is my happiness not important to you any more?'
'Of course it is,' I assured my mistress. 'I'll try really hard to learn from Mr George I promise. I know now I was never a good enough husband for you. I'm going to do my very best to be a good maid for you'.
'That's better. You're making me very happy with your attitude. Now why don't you kneel and kiss my boots like a good maid should?'
I quickly did as my mistress requested, savouring my *********** at the hands of this gorgeous creature. When I stood I had one burning question on my mind, 'Please ma'am, I'm sorry but can I ask one more question?'
'Open your mouth,' ordered my wife. 'Wider!'
As soon as I complied, Michelle spat straight into my mouth. 'Ask your question with a mouth full of my spit slut'.
'Please ma'am,' I began with a red face, concious of the others watching me from the car. 'I was wondering about my chance to cum, I mean that I won...'
'Mr George is aware of everything that went on yesterday sissy,' Michelle smiled. 'I'm sure he has everything in hand. Here is the key to your chastity tube, make sure you give it to Mr George straight away. Now off you go'.
'Yes ma'am'. I curtsied hoping to please my mistress.
As she walked away from me I blurted, 'I love you so much!'
Stopping in her tracks, Michelle turned and came back. 'I love you too baby,' then crack! She slapped my face. 'But do not speak to me without permission. Is that clear?'
Tears had formed in my eyes as I raised my hand to my cheek. I quickly curtsied again and dropped my gaze to her boots.
'I will be in my lover's arms tonight sissy. Remember that when you find out where you will be'.
With that she turned and walked away. I watched the car, my car, drive away before turning toward the house.
The hum1liation was a crushing weight as I trudged up the drive pulling my wheeled suitcase behind me. I missed my wife already. What the hell had I gotten into here? I felt so exposed in my girly getup, the tops of my stockings peeping from under my skirt as I teetered on the ridiculous heels. The reinstalled but plug made me mince like a girl, with it and my chastity tube reminding me of my frustration and desperate longing for relief.
The door was answered by a large overweight man, dressed sloppily in sweatpants and vest. His hair was uncombed and a few days stubble covered the bottom half of his face. Before I could think of what to say he smiled broadly and ushered me in. I wondered desperately what I was walking in to.
Sitting on his couch I held my knees together like a lady, although my skirt had ridden up to reveal my stocking tops and garters. The room was dark and untidy, take away cartons and empty beer tins littering the floor.
'I've been looking forward to this ever since Phil called me last week and told me about the new married slut he was fucking and her sissy faggot of a husband,' he said, leering at my legs. I hated him already.
He leaned back in his chair, his gut protruding between the top of his sweatpants and the bottom of his vest. He was covered in dark thick hair. His arms, chest and stomach matted with it.
'So, you're going to be staying with me for the week,' he smiled. 'We'll have to make sure your earn your keep won't we?'
'Yes sir,' I mumbled, unable to look him in the eye.
'You're a shy one aren't you?' he laughed. 'That's good, shows you respect your betters. Keep that attitude and we'll get on just fine'.
'Yes sir,' I answered. 'Please sir, my mistress told me to give you this'. I stood and took the key to my chastity cage to him, curtsying as he took it from me.
'Ahh yes, the key to your heart,' he laughed. 'Maybe we will need this, maybe not. That will depend on you. Now, your duties'.

I spent the next two days trying desperately to earn my release from Mr George. He put me to good use, scrubbing his kitchen floor, dusting, scouring the toilet, vacuuming, polishing, making his bed and cooking his meals. All while he sat and watched tv, occasionally shouting crude slurs at me. Many times I thought of quitting. Was it worth it? The best I could hope for was that he might see fit to give me the key to my cage and permit me to have a quick jerk into the toilet. Not much to hope for or look forward to. But what else did I have? Worst of all, the thought of disappointing Michelle, how could I face her? So I kept on working.
Phil was obviously emailing photos of himself with my wife to Mr George who took great delight in ridiculing me as he showed them to me, clearly revelling in my misery. What really hurt was that Michelle looked amazing. So beautiful, so happy with her man. My heart broke again every time that bastard laughingly made me look at the latest picture on his phone. I wanted her so much! I missed her so much! I needed to cum so bad! Seeing her with Mr Phil renewed my sexual frustration and doubled it every time till I though I must surely be losing my mind.
After two days and nights Mr George told me I had almost earned my release from chastity. My heart skipped a beat. But 'almost' was the key word.
Although he had three spare bedrooms, Mr George did not allow me to use any of them. He had secured a thick leather collar around my neck on my first night, securing it with a padlock. Then he had led me down to his cellar. It was cold and dark down there but it was to be where I slept each night. Sissy maids, he informed me were not allowed in the house unless they were working. I would spend each night of my stay padlocked by my collar to a metal hook fixed solidly to the wall about three feet from the bare concrete floor. My hands would be handcuffed behind me and my ankles locked together. This, he said, was to deter any silly thoughts of escape. The fact that I could neither lie down nor stand nor even shuffle into a comfortable sitting position, with the side of my face pressed against the rough brick wall, meant that I would be unlikely to waste time ********. That meant, apparently, that I would have ample opportunity to meditate on my failures as a man, a husband and even as a human being.
I cried most of the night for the first two nights. After that I thought I had no more tears left. I was wrong.
On the third day Mr George sent me to the cellar early. Opening a large cupboard he took out a set of wooden stocks, with a hole for the head and two smaller holes for the wrists. The sturdy looking frame was quickly bolted to the floor. I shook my head and took several steps away from the scary looking contraption.
Mr George just grinned at me, pulling the keys to my chastity tube from his pocket and jingling them in front of my face. 'You want to cum or not, sissy? Uniform off, panties too. You can keep the stockings and shoes'.
Once more my frustrated libido betrayed me and, in a few minutes I was undressed and trapped firmly by the heavy stocks. I winced as the hinged board closed shut and the hefty padlock snapped closed with a sickening click.
The stocks were mounted at waist height so my back was horizontal to the floor and I had to spread my legs slightly to make it less uncomfortable. My six inch heels put strain on my ankles and calves but Mr George swatted my ass when I made to remove them. 'The shoes stay on,' he ordered. 'A slut should look like a slut'.
He then went back to the cupboard to retrieve a large mirror which he propped against the wall giving me a perfect view of my helpless hum1liating position. Finally a video camera was set on top of a small table, positioned to take in all of the action.
'Look into the camera slut,' Mr George instructed. 'We're making a movie for that pretty little wife of yours. We want her to be able to see your face. Now, I'm going to beat you. Unlike your wife I don't love you or have any feelings for you at all. Well, perhaps contempt, but nothing more. Also, unlike Mr Phil, I have no need or desire to impress your mistress. I want you to understand, there is no emotion involved in the beating I am about to give you. As a sissy maid you must learn to live without emotion. You exist to serve, perhaps to amuse on occasion. Nothing more. Now, we shall begin. There will be one hundred strokes for you to endure. You will count each one and thank your mistress for making you her slave. If you fail to count or miss count we will start again from the beginning. If you take your eyes from the camera we will start again from the beginning. Apart from that I want you to feel free to do as you please. The cellar is sound proof. The house is detached. There is nobody to interrupt us. Oh, and should you pass out, don't worry, I have lots of smelling salts'.
'You may thank me and beg me to beat you as I please'.
'Please, you can't do this, I.....'
'The count will now be one hundred and ten strokes........one hundred and twenty'.
'Please sir,' I blurted. 'Thank you, please beat me as you please!'

'Look into the camera slut, tell your wife what you are,' ordered Mr George.
'Michelle, I love you. I'm doing this for you,' I sobbed.
Swish! The first stroke of the cane bit into the soft flesh of my ass. Then, straight after, another and another!
'I don't hear any counting slut. I guess we'll start again,' Mr George yelled.
'Aah, one thank you mistress, aah! two thank you mistress! Ahh, fuck, three, thank you mistress'.
'I told you to tell her what you are, cunt!' Mr George whispered in my ear.
'Please ma'am, I'm a useless sissy faggot'. I declared. I would have said anything at that point.
'Go on,' Mr George insisted.
'Please, ma'am,' I blubbered, 'I don't deserve you. I'm a pansy faggot cunt just like Mr Phil said'.
'You certainly are,' Mr George agreed wholeheartedly.
The v1cious caning continued, stroke after stroke across my ass and down my thighs. I knew it was completely futile but I screamed and pleaded anyway. I squirmed, I kicked out, I shook my head. Nothing helped, nothing changed, the beat1ng continued.
At forty strokes Mr George paused for a cool *****. 'How you doing there sissy?' He teased.
'Please, no more,' I gasped with a throat already sore from screaming.
'Oh come on, we haven't started yet,' he laughed cruelly. 'You do want that chance to have your little squirt don't you? Or, is that more likely to be a dribble'.
'Please sir, I'll do anything you say. I can't take any more. My ass is on fire!'
'Alright you sissy girl. Since you're still fairly new to this I'll give you break. I'll switch targets so your ass gets a little rest. You have a choice, ass, hand or foot. You choose which one you want, shout it out, not forgetting to say please of course and present it to the cane. Let's try a practice'.
I was told to shout foot and lift my right foot by bending my knee. He removed my shoe as I balanced on one leg. The whack of the cane across the sole of my foot was agony!
After practising the same routine for my other foot and the palms of both hands, Mr George seemed satisfied.
'Ok, those didn't count because we were just practising. Now we can start. You shout and present, I flog. If you don't choose anything I'll just go back to that sissy little ass. Don't forget to count slut'.
I have no idea how long it went on. I couldn't stand more than one stroke to any target and so switched around repeatedly. The pa1ns in every one of the areas Mr George attacked with that damned cane were unbearable. But bear them I had to. To make my t0rment even worse, several times I forgot to count, or lost count altogether, or forgot to thank my mistress. The pa1n blanked out any attempt to think. The only possibility of escape, to faint, was too scary to contemplate. If my legs collapsed I felt I might break my neck or strangle myself as my weight fell onto my neck trapped in the wooden stocks.
By the time it was over I was no longer crying out as I had neither the breath nor the ability. My voice was almost gone as I had gone on counting and thanking my mistress in a near inaudible whisper.
'There you go, you see, nothing to it,' Mr George announced.
I looked at my face in the mirror. I was pale and soaked in sweat, drool running from my gasping mouth. I had never experienced anything like this and yet there was a certain euphoria in having submitted and been a6used in such a complete and heartless way.
When the words I'd waited for months to hear finally came I was almost too dazed to understand them.
'Right slut, now you get your chance to cum,' Mr George announced as he undressed.
I had to lift my feet as he refitted my high heels. 'Got to make sure you're properly presented don't we?'
I had no idea what he meant and didn't care. I was going to get my first chance of an orgasm in so long! I began to fear I might not even be able to manage it. The spikes had done their job. My poor clitty had not even attempted to grow in weeks now.
I was jolted from my worried thoughts as I felt Mr George fidgeting with the lock on my chastity tube. Suddenly I was free! It was incredible, amazing. I felt so exposed.
'Phil wasn't kidding,' Mr George laughed. 'That thing is tiny! I think you should apologise to your wife for making her put up with that. It's fucking pathetic!'
Looking into the still running camera I did as I was told. I didn't care about the shame any more. I didn't care about anything but finally getting to cum.

'Ok sissy, this is how we're going to do this,' Mr George announced. 'I'm going to fuck your little pansy ass. You can cum from that if you want to. If not, I'm locking your little thing back up'.
I was past any kind of rational thought now, stamping my feet in their girly high heels, trying desperately to hump the air around my still flaccid little penis.
'Beg for it slut,' ordered Mr George. 'Beg me to fuck your little ass and make you cum'.
I clenched my fists in helpless frustration as I muttered, 'Fuck me'. I was so horny I couldn't think straight.
'Louder you little cunt,' he commanded. 'Beg me like the little slut your wife and her lover know you are. Or the cage goes back on right now'.
'Please,' I said louder, trying to find some saliva to lubricate my dry sore throat. 'Please fuck my pansy ass sir. Please don't lock me back up. I need to cum so bad. Please sir!'
There was no response. He was waiting for more.
'Please, please, please sir, I beg, I beg you sir, please pump my ass with your big hard cock.....I'll do anything you say I swear......please make me your slut'.
That seemed to do the trick. Mr George stepped around to the front of the stocks. He was completely naked, the thick dark hair that covered his body making him look more like an an1mal than a man. His large belly hung over his semi erect cock which stuck out from a thick wiry bush of black pubic hair.
Waving his cock in my face he suggested, 'Why don't you tell your wife what you need sissy'.
Looking at the camera I told her, 'I need Mr George's big cock. I need him to fuck my sissy ass. I'll do anything he says, anything! Please let me cum!'
Satisfied with my admission, Mr George stepped forward, offering his circumcised cock head to my mouth. I opened wide like the good little slut I was. He grew rapidly under my devoted ministrations. His cock was not as long as Mr Phil's but wider and I worried over how my poor little ass could possibly accommodate such a monster. Keen to take his pleasure from my ass, Mr George soon withdrew his now fully hard cock from my sore gaping jaw. He went behind me and I felt his large rough hands prying my soft buttocks apart.
I felt the ever present dildo being pulled out then the bulbous head of his tumescent organ was pressing for admittance to my most private place. There was a painful resistance and then he was in. A few short strokes and then I felt him bottom out inside my ass, his pubic hair scratching the pale soft skin of my buttocks. I watched my own face in the mirror, mortified as I felt a real man's cock fill me completely for the first time.
He grabbed my hips and started to hump. I moaned loudly, glad for the first time that I had been prepared by the daily wearing of a butt plug. Despite my embarrassment I realised it actually felt kind of pleasant. I closed my eyes, biting my lip and focussing on the feeling of that monster rod stroking my prostate.
My eyes shot open when I felt the cum oozing from the tip of my even now flaccid little penis. I rocked my hips, desperately trying for just a little more sensation, but it was no use. Months of pent up cum dribbled out without any of the normal amazing sensation of orgasm.
I had to have more. I needed more. It wasn't satisfying enough. I begged Mr George to fuck me harder, catching glimpses of myself in the mirror, my face bouncing as he slammed into me over and over.
I felt a couple of feeble spurts as more sissy slime was released, but it wasn't nearly enough. I cried as I felt him slow and push as deeply into my ravaged backside as he could, groaning and swearing, calling me a useless fucking faggot as he shot his thick load into my sissy ass, penetrating me so deeply I almost immediately felt its salty taste on my tongue.
'Good girl,' he praised me as he eventually pulled out.
I wanted so much to beg him to put it back, to fill me again, to let me feel his cock inside me. But I knew it was pointless. There was no cuddling. The cage was quickly re secured without comment or ceremony. Then smacking my ass he grabbed his clothes and walked up the stairs, closing the cellar door behind me.
I was left alone, still locked in the stocks, legs shaking, cum dripping out of my ass and down my thighs.
As I watched myself cry, mascara running down my cheeks, I realised the camera was still running. I wondered what my wife would think of me when she saw the recording of her sissy husband being fucked by another man and begging for more. I'd acted like a cheap slut, I'd even cum like a woman. Worst of all, I wanted it again.

The following day found me kneeling on the floor focusing every bit of effort I had into pleasing Mr George's hard cock. I looked up at his face as I sucked, hoping against hope that he would reward me by taking my ass again.
After spending what felt like an eternity locked in my chastity cage, it has been at least somewhat of an unexpected relief to get my ass fucked. I wasn't gay. I'd never fancied men. Never. The thought repulsed me. But I could not deny that achieving that feeling of release again was all I could think about.
I wondered what it must be like to have someone giving you blow-jobs on demand. It sounded amazing. I imagined myself in Mr George's place, a desperate slut eagerly sucking my cock and begging to have her ass fucked.
I had taken extra time on my make-up and outfit with frilly little skirt and white stockings I knew I looked so slutty. As I knelt between my master's legs I raised my ass and swayed it side to side. I could feel my skirt bouncing, barely covering my sissy bottom. I was learning what it meant to be a desperate bimbo.
For his part Mr George was happy to relax in his favourite chair with a little slut worshipping his cock. He grabbed the remote and flipped through channels on the tv. I moaned as I realised I would be sucking his cock for a long time as he used me without the slightest consideration of my needs.
That night as I sat on the cold cellar floor, collar padlocked to the hook on the wall, arms and legs cuffed securely and face pressed against the rough cellar wall I tried to think of new ways I might try to earn a real fucking from my master.
A couple of days later my hopes were raised but then dashed again as I realised that Mr George had not reached for his key chain when he told me to remove my panties and butt plug then get on all fours on the rug in the centre of the lounge. Finally my crushingly hum1liating efforts had paid off, I was going to get fucked but I wasn't even going to be allowed out of my chastity tube this time.
It had taken far more hours on my knees between his legs than I cared to think about to earn my second fucking. I trembled in anticipation as I waited on all fours, spreading my stocking clad knees on the floor. I pulled my frilly maids skirt over my ass for him. I was using depilation crème as instructed and I hoped he liked what he saw as I swayed my smooth backside like a cheap whore.
I was staring at the floor, so the f0rceful blow from his huge rough palm across my thigh caught me off guard. I yelped like a girl as he reprimanded me, 'Hold still bitch. You're not as sexy as you think you are'.
I obediently stopped, embarrassed by his put down. I just moaned softly as he grabbed me with both hands and pulled my ass onto the tip of his cock. I was glad then of the time I had spent coating his huge fat rod in my saliva and of the Vaseline I always used when refitting my butt plug every morning after my ablutions and soapy enema.
I tried not to think about my own poor forgotten little manhood and just focus on the warm cock easing into my ass.
I slipped into a kind of sissy delirium as Mr George began thrusting in and out, holding me firmly in position. As he started speeding up he occasionally smacked my ass, reminding me who was in charge. Each time I let out a girlish little yelp.
As he continued to slam into me I felt the familiar pulsing as the pressure on my prostate started the cum oozing out of my clit. The same dreaded feeling of frustration accompanied it as I was milked without any feeling of satisfaction at all.
George called me names as he fucked my ass-hole, telling me I was just an ugly bitch to be used and thrown away. I was a pathetic sissy slut, a faggot who could never satisfy a woman. A whore for real men's cocks. A cum dump. I cried but nodded my head meekly, wishing I was prettier. Any semblance of manhood was gone forever. All I had left was the need to become a perfect slut for my masters and mistress.
I arched my back and moaned loudly, hoping Mr George was enjoying using me. He didn't say anything but soon a load of sticky goo filled my ass to overflowing.
As he pulled out of me I thanked him, wishing desperately that it had lasted longer.
Any afterglow was immediately squelched for me when he noticed my little cum puddle on the rug.
'Did I tell you to cum faggot?' he demanded.
I cried and shook my head, panicking at the thought of another beating like the last one Mr George had given me. I immediately lowered my head to lick up my cum before it soaked into the rug.
'You are a useless, stupid little pansy cunt!' he went on, reaching from behind to grab my little balls as I licked the floor.
I squealed as he held my precious balls in place with one hand while slapping them again and again with the other.
I tried desperately to continue licking my up cum as I sobbed, the pa1n shooting through me at each cruel swat. I started begging him to stop, pleading through ******* tears and sobs.
When he finally stopped I was a mess. I fell to the floor, crying uncontrollably. He just stood watching me, shaking his head.
About ten minutes later I was able to gather myself and immediately knelt in front of him, thanking him for fucking me. He just sat there with a big superior grin on his face. I felt his cum oozing out of my ravaged ass onto my thigh as I lowered myself to kiss his dirty boots.
Hearing him unzipping his pants, I knew what to do. While he used the remote to turn on the game, I got as comfortable as I could between his legs and spent the next two hours respectfully and gently worshipping his huge hairy balls.
When the game finished Mr George stood and, without saying a word, snapped his fingers and pointed to the floor at his side. On all fours I followed him to his bedroom. After undressing and throwing his clothes on the floor he laid back on the bed. I quickly picked up the discarded clothes, folded them and neatly placed them on a chair. Mr George had pulled a quilt over himself and, after a respectful curtsy, I turned to leave.
'Where the fuck are you going slut?' he demanded. 'Get your head under here and finish what you started'.
'Yes sir, of course sir,' I simpered.
Lifting the duvet at the bottom of the bed slightly, I slid under it, crawling forward between his spread legs. Mr George sighed in satisfaction, crossing his hands under his head. Even after so much practice at being a sissy girl, I still recoiled when I felt his penis on my tongue. But what choice did I have? Steeling myself I pushed past the feelings of shame and self loathing to take as much of the long fat shaft into my mouth as possible, sliding my obedient sissy tongue along the bottom of his stiffening cock.
When I paused to give my aching jaw and sore tongue a break I was rocked by a heavy fist slamming into the side of my head. If not for the thick duvet it would surely have felled me. As it was my ears rang but, nonetheless I immediately apologised and went back to worshipping my master's dick.
I felt trapped as he started thrusting his hips, pushing his horrible cock into my throat. Taking the back of my head in both of his large powerful hands denying me any possibility of escape, he called me a stupid, useless pansy cum dump. His thrusts got longer and deeper and I knew what was coming. Tears of panic, frustration and hum1liation trickled down my face as fought my gag reflex. I feared the wrath of Mr George even more that I feared ******* to death. Finally his cum shot into my throat and ran down into my stomach.
I tried to keep my crying quiet as Mr George drifted off to a satisfied s1eep. I obediently continued licking his now empty sweaty balls until I heard him start to snore. Then, as I left my master's bed to retire once more to my cold dark cellar, I realised he was right. A cum dump was exactly what I was. It was all I was, perhaps all I deserved to be. After all, what kind of man would allow his wife to do this to him. Allow? Ha! I'd encouraged her.

Blue, didn't think this story would get any better, however you managed again to reach new levels !!!!!! As always....Pls. Continue !!!!!!!!!

Thanks Blue, I'm loving it!

Amazing story, loving every aspect of this.

More please Blue! More!

More please?