The Willing Cuckold

Pipsqueak was allowed to drive his wife and her lover to the airport for their trip to Jamaica, dressed of course in the cheap pink nylon tracksuit that was his only male item of clothing. Being somewhere that people were often searched, caused additional worries for him as he followed the happy excited couple across the concourse pulling their wheeled suitcases behind him like a bell boy. At least he wouldn’t have to go through a metal detector and have to explain his chastity cage. Underneath the tracksuit he was wearing his now normal underwear of corset, slip and white stockings. He kept looking down at his thighs watching the outline of his garters appear with each step as the thin nylon tracksuit trousers stretched over his thighs. He didn’t dare look around in case someone else had spotted them.

‘I think it would be nice if you took us to the airport,’ Linda had explained. ‘The contrast between my excitement at going on holiday with my boyfriend and your mood of jealousy, humiliation and dread at the prospect of household drudgery under the authority of my sister will be a very special experience for us both. It’s a big step for us and we should do it together.’

Linda looked gorgeous as usual in short skirt, cropped t-shirt showing off her flat belly and sexy wedge sandals and pipsqueak had to admit to himself that Sam and her made a stunning couple.

‘You can go now pipsqueak,’ Sam said as he towered over pipsqueak who glanced at his wife for confirmation.

‘Don’t look at me pipsqueak,’ Linda smiled condescendingly at her husband. ‘You know you obey Sam as you do me.’

‘Yes Mistress,’ pipsqueak tried to answer quietly so as not to be heard by the other holiday makers making for the check in desks.

‘Have a nice time,’ he offered lamely, feeling a moment’s panic at the thought of his wife jetting off with the man she had chosen as her lover.

‘Oh, we will, don’t worry about that,’ she laughed before lifting her face to accept a wet kiss from the black giant holding her hand.

‘Make sure you’re a good gurl for Lorraine like you promised, you know I’ll make you regret it if you aren’t.’

‘Yes Mistress, I will,’ pipsqueak smiled weakly, hating to be reminded of the two weeks in store for him being lorded over by his bitch of a sister-in-law.

Feeling a sudden impulse, he went to kiss his wife’s lips desperate to reaffirm their bond but she pulled away.

‘What on earth are you doing pipsqueak?’ Linda asked, smiling with fake indignation.

‘I was just… ‘

‘Kiss my feet,’ she ordered coldly.

‘But, what about all these people?’ pipsqueak pleaded.

‘None of these people should matter to you pipsqueak, only me. Unless you’re ashamed of me?’

‘Of course not Mistress,’ he assured his sweetly smiling wife before dropping to his knees in the middle of the airport concourse and planting soft kisses on the red painted toes of each of his wife’s cute little feet where they poked out from her wedge sandals.

‘That’s better. Now I’m sure Lorraine will be keeping you very busy but, when you eventually get to your sad little bed in the closet every night, don’t forget to think about me making love with my boyfriend every night and waking up in his arms every morning. Bye pipsqueak.’

Still on his knees, pipsqueak watched her walk away, her lover’s hand protectively placed on her gorgeous ass, then, remembering where he was, quickly stood and, red faced, trying not to think about all the amused faces around him, hurried for the exit, his underused cock straining against the walls of its tubular prison.

After more than a week of working his sissy socks off trying to satisfy the constantly growing demands of his heartless sister-in-law, cleaning, washing, scrubbing and polishing; only to be told it wasn’t good enough and having to do it again nursing a stinging bottom or aching swollen palms from a bamboo cane she had found in the garden, pipsqueak was exhausted. He’d tried, he really had. He genuinely wanted to please his unfaithful wife with the report she would get from her sister when she returned from her holiday with her boyfriend, to prove to her how much he appreciated how hard she was working to make their new relationship work, but it was impossible. Linda was demanding and unfair but her sister took it to different level.

‘Unlike my dear sister, pipsqueak, I don’t have any history with you, I wasn’t misguided enough to marry your sissy arse. All I feel for you is contempt so, if its mercy or pity you’re looking for, you’d better look somewhere else because I have none for you. I will do whatever it takes to break you and once I’ve broken you, I’ll continue to make your life hell just for my own amusement and to show my poor sister what a worthless waste of space she married.’

So, rising at 5am he worked through lists of housework, served as Lorraine’s slave maid, tried his best to memorise various sissy dance routines she made him learn then sat at the dining table under her watchful eye writing lines like, ‘I am a worthless sissy slut who does not deserve such a wonderful wife’, four or five hundred times, or composing essays on subjects like, ‘Why my wonderful beautiful wife needs a lover’, ‘Why I admire my wife’s handsome boyfriend’ or ‘Why I am in awe of Miss Lorraine’s beauty and so indebted to her for taking the time to make me a better maid’.

Bedtime came after midnight once he had reported to Miss Lorraine in her bedroom. ‘What do you think your wife is doing right now pipsqueak?’ she would tease him. Or, ‘How many times do you think Linda and Sam have made love today, wimp?’ Or, ‘Do you think you’ll even recognise Linda when she gets back after two weeks in Jamaica with a real man?’ The variety of torments was never ending.

‘Put your head under the covers and suck my toes while I text your wife. You know I think she’s in love with Sam. You must have expected that surely. How could she not be? Don’t worry though, I’m sure she’ll still keep you around, even if it’s just so that she doesn’t have to go back to doing housework.’

So, filled with impotent jealousy and helpless humiliation, pipsqueak sucked her delicate painted toes until she went to sleep and then went back downstairs to tidy up the awful mess that she deliberately generated to dishearten him. On the advice of her sister, Lorraine made a point of complaining, criticising and ridiculing regardless of how hard pipsqueak tried to please her. No word of praise or gratitude crossed her lips; an experience she found quite refreshing.

‘I don’t want her ever to have the opportunity to feel satisfaction with her performance Lor,’ Linda had said. ‘She should always feel inferior, useless, worthless even, that no matter what she does she will never please me, that I barely notice her except to be disappointed by her pathetic efforts to show how much she loves me and wants to make me happy.’

‘If that’s what you want Sis,’ Lorraine responded, feeling an unexpected rush of excitement at the prospect.

‘Not just what I want,’ Linda smiled. ‘It’s hard to understand sometimes I know, but it’s actually what he, sorry she, wants too. Although she doesn’t always realise it right away. She needs this, it’s always been her fantasy and now I have the chance to make it real for her. So please don’t think you need to take pity on her, feel sorry for her or worry about upsetting her; mistreatment from a beautiful woman is what she lives for.’

‘And in the meantime, you don’t do too badly out of it, sis,’ Lorraine grinned.

‘I don’t do I?’ Linda laughed. ‘It was hard at first, it took a long time for me to get my head around it. But now I have and I’m really glad I gave in and tried it. I so happy now and, in his own strange way, so is Chris… sorry pipsqueak.’

‘I think I’m beginning to understand that now and I’m really looking forward to two weeks of just pipsqueak and me. I want to explore this whole domination thing. If he gets off on the way you treat him, he’s going to just love his little sister-in-law!’

When, one morning, Lorraine told pipsqueak to go and stand inside the garage to wait for her, although nervous about what the devilish bitch might have in mind, he was actually glad of the chance to rest. Then she walked in with a length of washing line, some zip ties and a pair of scissors in her hands.

‘Hands behind you slut!’ she ordered coldly, her heels clicking across the concrete floor.

Pipsqueak felt her tying his thumbs together with a zip tie then fastening a pink leather dog collar around his neck. More zip ties were used to connect his tied thumbs to the collar. The sound of the ties being tightened accompanied the uncomfortable sensation of his hands being pulled up his back until his elbows stuck out either side like little chicken wings.

Next one end of the washing line was thrown over the wooden beam directly above pipsqueak’s head before being pulled it down and tied to the back of the pink leather collar.

What the fuck? pipsqueak’s mind raced, was she going to hang him? ‘Please Miss Lorraine… ‘

‘Quiet pipsqueak,’ she interrupted his worried protest. ‘Learn to suffer in silence when your betters decide to amuse themselves with your suffering! You do think of me as your superior, don’t you pipsqueak?’

‘Yes, yes of course, Miss Lorrayyyyyy!’ Lorraine laughed as her hapless victim’s words were cut off by the pull of the collar on his neck as she hauled at the other dangling end of the washing line before tying it off to a convenient eyelet on the wall. Finally, she bent in front of pipsqueak to tie a length of line to each of his… her, she must get used to not just calling the sissy a her, but actually thinking of it as one.

‘The idea sis, is that by, not just calling pipsqueak a her, but really thinking of her as a her, it makes it surprisingly difficult for her to think of herself as anything else. It certainly insults any vestige of manhood she might be hanging on to.’ Linda had explained to her.

Back with the washing line… each ankle was wrapped with a length of line then she stood up facing the sissy maid and had her remove her stiletto heels. The reduction in height had the effect of pulling uncomfortably on the collar around pipsqueak’s neck. After ordering the maid to move one stockinged foot towards the garage wall she secured the other end of line to a leg of the heavy shelving that lined both walls of the garage. When she repeated the process with the other ankle, making pipsqueak spread her legs wider, so reducing her height even further, the collar around her neck felt like a noose choking her.

‘Oh, dear pipsqueak,’ Lorraine said with mock sympathy as she stood to admire her work, ‘You seem to be struggling a little there. Are you alright?’

‘Ppp… ppplease, its choke… choking… ‘

‘Oh dear,’ Lorraine smiled. Would you like me to help you pipsqueak?’

She burst out laughing as the pathetic wimp tried to nod her head.

‘My advice would be to stand on tiptoe directly under the beam sissy. That way the line might not be so tight around your neck.’

Taking in her words, pipsqueak looked up at the beam, shuffling his feet to try to get a better position. It worked, but only slightly. At least he could breathe now, kind of, but how long could he stay on tiptoe? His calves were aching already.

That’s when Lorraine appeared in front of him again, this time swishing a thin plastic rod about eighteen inches long.

‘You don’t like me, do you sissy?’ she smiled.

What could he say? ‘You… you never seemed to think I was good enough for Linda,’ he croaked out cautiously.

‘And I was right, wasn’t I?’ She replied, as she scratched her nails up his quivering thighs, ‘I mean look at you; you wear a sissy maid’s outfit 24/7, spend your whole life doing housework and serving your betters as no more than a skivvy and support your wife cuckolding you with another man? And that’s without mentioning how you like to suck cock? Yes, Linda told me. She says you do it to show you love her but I think you do it because you’re a cock sucking little slut. You’ve always been a pathetic sissy cock sucker; you’ve just never had the opportunity to put it into practice until now. Until my poor, long-suffering sister couldn’t take it anymore and finally found herself a real man to fuck her! Tell me what you’ve always been faggot!’

‘A cocksucker, Miss Lorraine.’ Pipsqueak mumbled.

‘Louder, tell me what you are, what you’ve always wanted to do. Wait, I want to video it on my phone to send your pretty little wife. Let’s hope she can find time between long hot sessions of deeply satisfying sex, to look at it. Right, go ahead.’

‘Please Miss Lorraine,’ he begged.

‘Fucking say it!’ she screamed in his face as she reached up under his skirt to grab and twist his blue balls.

‘I’m a cocksucker Miss Lorraine! I’ve always wanted to suck cocks!’

‘Now say thank you to your poor wife for giving you the opportunity to suck her boyfriend’s huge cock.’

‘Thank you for letting me suck your boyfriend’s cock, Mistress,’ pipsqueak sagged in resignation.

‘Perfect!’ Lorraine beamed. ‘There, all sent. Now, would you like me to take your mind off your discomfort?’ she asked in mock concern but tapping the thin plastic rod menacingly against pipsqueak’s cheek.

He shook his head no but she walked behind him anyway and began to flick the rod against his hands, his arms, his back. Not powerful blows, just painful nips repeated over and over, taking away his breathe as the pain built and built. He tried to move away but that just tightened the line around his neck making him choke again.

‘Silly gurl,’ Lorraine laughed. ‘You’re choking yourself, I thought you didn’t like that.’

When the rod was switched from his arms to the backs of his legs it was a relief – for a few seconds – then the agony was renewed.

‘Ooops there you go again, strangling yourself. I’m beginning to think you might have a hanging fetish pipsqueak.’

Pipsqueak was crying now. From the pain of the rod, the choking, the unfairness and because he missed his darling wife. He hadn’t even done anything wrong! He worked his ass off, humiliated himself, done everything Lorraine demanded, he’d really tried to please her, to show her how devoted he was to her sister by serving her. Still, it wasn’t enough. The bitch had not even made a pretence that this was deserved, she was doing it just for her own enjoyment!

‘Oh, what’s wrong pipsqueak, don’t you like spending quality time with your sister-in-law?’ Lorraine asked him as she stopped her whipping to come around in front of him. ‘I’m almost offended. I’m having a lovely time. I could do this for hours! In fact, I think I will. Oh dear, more tears? Come on now cheer up. I’m giving you a nice rest, aren’t I? Let me see your sexy smile, come on flutter those baby blues for me. Show me what my gorgeous sister saw in a worthless wimp like you.’

His desperate try at a smile would have broken the heart of a lesser Mistress but Lorraine was determined to give her sister’s sissy husband an experience to remember for the rest of his life. A reason to fear her, to dread her visits, to do anything to; not please her because that wasn’t possible, she was showing him that; but at least to attempt to avoid the worst of her cruelty.

‘You love this don’t you slut? You love being at the mercy of a dominant woman, being tortured and punished for being a failure as a man by a gorgeous woman who feels nothing but contempt for you. Tell me! Tell me you love it!’

‘I love it Miss Lorraine,’ pipsqueak croaked, in no mood to argue with this woman who could break him so easily, so completely and at will.

‘Look at me, tell me how grateful you are for being treated like this!’

As she spoke Lorraine lifted the hem of pipsqueak’s uniform skirt and began tapping her perfectly manicured finger nails on the metal chastity tube encased by his sissy panties.

‘Thank you, thank you Miss, thank you.’

Dropping to her haunches in front of the poor sissy Lorraine yanked the panties aside to pull the tube free whereupon she began simulating giving him a blow job.

‘Is this where a woman belongs pipsqueak?’ she teased. ‘Maybe it is, for a real man. I wouldn’t be surprised if that’s exactly what your wife is doing with her boyfriend right now. She never did it for you though did she?’

Pipsqueak shook his head as much as the nylon noose allowed.

‘Would you like me to do it? I have the key. I could slip off that nasty cage, open up my sexy lips and suck your hard little cock inside my warm wet mouth. Would you like that? Would that make it all better? Would you like me then?’

‘Yes Miss Lorraine, oh please, I’d do anything, anything you say, I swear!’

‘But you’ll do anything I say anyway won’t you? Because you’re terrified of me and even more terrified of upsetting your sweet little wife. So, I have nothing to gain really, do I?’

‘No Miss Lorraine,’ pipsqueak hung his head. Why had he let himself hope she might be serious? He was so stupid!

‘I’m sure she’ll be interested to hear how you tried to persuade me to give you a blowjob though, won’t she? Imagine how upset she’ll be that you took advantage of her absence to try to seduce her poor innocent little sister! You can’t exactly blame Linda for not wanting that disgusting little excuse for a cock anywhere near her mouth, can you?’ she snarled as she gripped his swollen blue balls and twisted as she stood. ‘What woman would?’

‘Aaaggghhhh!’ Pipsqueak squealed, trying desperately to shuffle one way then the other and succeeding only in choking himself more effectively.

‘You’ve been a terrible disappointment as a husband and as a man pipsqueak. But don’t worry, we’re going to make sure you make up for all the years my sister wasted on you.’

‘Aaaggghhh! Please Miss Lorraine!’

‘Shhhhh, calm down sissy,’ Lorraine soothed. ‘If you end up hanging yourself Linda will be mad with me for… mmm… maybe ten minutes or so!’

Pipsqueak was crying again with pent up emotion, frustration and helpless fear of the woman with his balls in her hand.

‘Might as well twist these off for what use they are, right pipsqueak? Oh, you’re crying again. You look so pretty when you cry.’ She leaned forward and spat in his face. ‘I’m going to ride that pretty face until you pass out tonight pipsqueak. But not until I’m done having my fun here eradicated from you the last atom of remaining male ego and reduced you to the pathetic, simpering little sissy faggot I always knew you were.’

Pipsqueak closed his eyes in utter defeat as Lorraine began on the fronts of his thighs with her rod of pain. Little taps that nipped, annoyed, angered and then broke him so comprehensively he was no longer sure who he was. All he knew was that he would do anything this woman demanded, anything to avoid angering this her, anything to escape her amused torture of him. And when his beautiful, gorgeous, stunning, wonderful, wife returned he would do whatever it took to show her how much he loved, worshipped and appreciated her. That is, if he could just survive her sister.

‘Open your eyes pipsqueak,’ Lorraine said, as she sidled up close to him, her face almost touching his. She looked so calm, so cool and beautiful. ‘Now open your mouth,’ she whispered in his ear. ‘That’s it, wider, wide as you can, good gurl, now keep it like that.’ Pipsqueak could not help closing his eyes when she spat straight into his gaping mouth. ‘Keep those eyes open sissy, I want you to see the contempt on my face.’ She spat again into his mouth. ‘Linda told me you like it when she spits in your face, especially in your mouth. Do you like it when I do it too?’

Pipsqueak could only nod with his mouth wide open.

‘Does my spit taste different to Linda’s? Go ahead, swallow it. That’s a good gurl, now open up again, I’m not finished. I suppose hers tastes mostly of her boyfriend’s cock, does it? How do you deal with the fact that your wife’s mouth as well as her pussy tastes of another man’s cum? Does it make you jealous? Or does it just turn you on? I’m sorry pipsqueak if my spit doesn’t taste as good as your wife’s. Maybe I can make up for that by giving you more of it. Would you like me to spit in your mouth again? Nod your head if you would.’

Given the choice between the deeply humiliating act of swallowing Lorraine’s spit and the alternative of returning to the agonising pain of the plastic rod, it was a no brainer.

‘OK, hold still now, let me see if I can fill up that sissy mouth.’

Trying not to retch in disgust whilst being slowly strangled was a very scary experience for pipsqueak and he was immensely relieved when Lorraine finally tired of her cruel game and told him he could shut his mouth. Sadly his relief was short-lived as she walked behind him and returned to whipping him with the plastic rod, backs of legs, arms, hands, backside then back to the fronts of his thighs.

After more than two hours of impossible discomfort, unbearable pain and merciless humiliation at the hands of his beautiful but cold-hearted sister-in-law, pipsqueak was completely exhausted and struggling to support his weight on his red-striped and bruised violently shaking legs and cramping toes He’d tried moving some of the strain on his awkwardly splayed legs to his neck and the line suspending him from the garage roof beam but found it just as painful. And now he had another problem.

It was several hours since he’d been able to relieve his bladder and he was getting desperate. The idea of pissing himself in front of his heartless sister-in-law was too appalling to think about, he had to hang on somehow.

‘You know we really should spend more time together doing things like this, pipsqueak,’ Lorraine smiled as she put down the glass of wine she’d been sipping and picked up the damned plastic rod once more. ‘For my sister’s sake I think we should get to know each other better, don’t you?’

Pipsqueak’s throat was too sore to make much of a response now but he tried anyway. He had to explain to her he needed the toilet.

‘I can’t understand you pipsqueak,’ Lorraine said as she walked toward him, tapping the clear plastic rod against her palm.

When the quick short blows started yet again on the fronts of pipsqueak’s thighs, he managed to squeal out clearly enough,’ Pleashhhh!  Toiletsh!’

‘Did you say you need the toilet pipsqueak?’ Lorraine asked as she came around in front.

‘Pleashhhh!’ he begged.

‘Wait!’ Lorraine snapped before hurrying over to her handbag to retrieve her phone.

‘We should capture this for posterity… or at least to give my big sister a laugh. Right pipsqueak,’ she began after pointing her phone at her helpless crying victim and pressing the button to begin videoing him. ‘When I give you the command, you may piss yourself. On the count of ten. Ten, nine, eight, seven, six, oh shit! You filthy little slut! Look sis, your worthless maid seems to be incontinent now! Don’t be surprised if she’s wearing a diaper when you see her next.’