The Willing Cuckold

Linda had a sister, Lorraine. At thirty-five she was five years younger than Linda, the headmistress of a secondary school, divorced with no children. Chris had always had a secret crush on her and had even fantasised about being dominated by her but he never actually liked her, mainly because she had not made a secret of the fact that she didn’t think he was good enough for her sister. When Linda announced one morning that Lorraine would be coming to visit, he assumed that he would be donning the only item of male clothing he had left, a tracksuit he wore to wash the windows outside, do some work in the garden or occasionally clean his wife’s or her lover’s car, then going out somewhere for the day. But then Linda went on to make it clear that Lorraine would be staying for a few days.

‘So shall I book a hotel or something and you can say I’m away somewhere?’ he asked.

‘Don’t be silly sweety,’ Linda smiled. ‘Why would we do that?’

‘I suppose I could just wear the tracksuit in the house,’ he suggested.

‘Certainly not,’ his wife declared. ‘You will wear your uniform as normal.’

‘But we can’t, I’ll look ridiculous, what will she think?’

‘I beg your pardon!’ Linda snapped staring coldly at her sissy maid husband.

‘Sorry Mistress,’ he backtracked with a submissive curtsy. ‘I meant, what will she think of me, Mistress?’

‘She will think that she was right about you all along. That you are not man enough for me. But she will also see that we’ve now done something about that.’

‘Please Mistress, please don’t do this!’

‘It’s too late in the day for you to get cold feet I’m afraid. I happen to be proud of what we’ve made you into and I want my sister to see how happy I am. I’ve never had secrets from her so I’m not about to start now. Think of this as an opportunity for you to show Lorraine what an important part of my life you are now and how hard you work to please me. And don’t pretend you’ve never fantasised about being dominated by her; I know you too well you little pervert! Now get yourself over my knee so I can attend to your earlier lapse of respect. A burning hot bottom might take your mind off your coming embarrassment for a little while. I wonder if my sister would like to spank you while she’s here?’

So it was that pipsqueak found himself in the kitchen, holding a silver serving tray on which sat two China cups and saucers and a pot of tea. On the instructions of his wife, he had taken extra pains with the new sissy maid uniform she had bought him for the occasion. His makeup was perfect, the lines up the back of his stockings dead straight and his now quite long hair tied with a pretty silk ribbon. The black patent leather shoes were new too and were already hurting his feet.

‘It’s time we moved you on to higher heels pipsqueak,’ Linda had told him when she presented the shoes to him the previous week. ‘You’ve had it easy with those four-inch heels for long enough. These are six inch and will accentuate your sexy gurly calves. I doubt if you’ll find them particularly comfortable but that’s hardly my main consideration. A servant like you needs to be constantly reminded of her sissy status. No man would or could walk in these but that shouldn’t be an issue for you should it, pipsqueak.’

‘No Mistress, thank you Mistress,’ pipsqueak said as he took the ridiculously high but extremely sexy shoes from his wife with a curtsy.

‘You’ll need to practice wearing them. I want you perfect for Lorraine’s visit. Keep your steps short, place one foot directly in front of the other, sway those girly hips and you’ll be fine.’

He didn’t feel fine as he stood holding the tea tray, listening to the voices of his wife and her sister coming from the lounge. He felt sick. How could he do this? The embarrassment! The humiliation! But what choice did he have? Maybe he could somehow brazen it out, walk in there with his head held high. If he didn’t hurry up there was a danger Linda would come looking for him and bring Lorraine with her. Their finding him cowering in here would be even worse! So, placing one foot carefully in front of the other, swaying his hips just like he’d practiced, he set off for the lounge.

The last thing pipsqueak expected as he entered the lounge, paused in the doorway to curtsy then sashayed over to place the tea tray on the coffee table and begin, with shaking hands to pour the tea, was to be ignored. The two attractive ladies did not even pause in their conversation or glance over at him. Even when pipsqueak, with a lump in his throat realised that he did not know if Lorraine took sugar and had to curtsy in front of her and wait for her to acknowledge him before he could speak, Lorraine simply ignored him.

‘I think the maid wants to ask you something Lor,’ Linda eventually prompted her sister.

‘Yes, what is it?’ Lorraine demanded curtly giving a look of contempt as pipsqueak, painfully conscious of how red his face was under his makeup and how hard his cock was pressing against the unyielding steel walls of its prison, curtsied once more.

‘Please Miss Lorraine, would you like sugar?’

‘No,’ was her only response before returning to the conversation with her sister.

After another humiliating curtsy pipsqueak stepped back and turned to leave, deeply grateful to his wife who, it seemed, had clearly saved him at least some embarrassment by briefing her sister before her first encounter with the maid.

‘Where do you think you are you going, pipsqueak?’ Linda demanded, before taking a sip of her tea. ‘Did either of us dismiss you?’

‘No Mistress,’ pipsqueak mumbled, his hopes of getting back to the safety of the kitchen dashed. ‘Sorry Mistress, I thought…’

‘I know what you thought pipsqueak,’ Linda said as she glared at her sissy maid. ‘You thought you’d leave without introducing yourself to my sister. Come here and present yourself this instant!’

‘Yes Mistress,’ pipsqueak shuffled over, acutely conscious of how ridiculous he must look to his wife’s beautiful sexy sister.

‘Good morning, Miss Lorraine,’ another damn curtsy. ‘My name is pipsqueak. I am Miss Linda’s maid.’

‘Well,’ Lorraine smiled coldly as she looked up at the hapless husband. ‘I’m happy to see that Linda finally realised what you are and found a more suitable position for you. Are you a good maid?’

‘I… I try to be Miss Lorraine.’

‘Well, I suppose you can’t possibly be a worse maid than you were a husband, could you?’

‘No Miss Lorraine,’ pipsqueak responded wishing the ground would open up and swallow him whole.

‘And as for trying, I suggest you try harder. Now that my sister has found herself a real man you need to earn your keep.’ So, Linda had told her sister about cuckolding him too.

‘Tell me… pipsqueak was it? Tell me pipsqueak, do you approve of your wife’s choice of lover?’

‘Please Miss Lorraine, it’s not for me to say.’

‘Mmmm, good answer. Perhaps we can make a maid of you yet. Though from what Linda has told me there is some way to go yet. You’ll be glad to hear I’ve decided to help. The thought of knocking a pathetic wimp like you into shape appeals to me. What do you think?’

‘Thank you, Miss Lorraine,’ pipsqueak curtsied, hands clasped in front of him over the skirt of his uniform, desperately hoping neither of his gorgeous tormentors would notice his chastity caged cock twitching and bobbing under there with excitement.

‘We’ll see if you’re still thanking me when your Mistress gets back from holiday.’

‘He doesn’t know yet Lor,’ Linda laughed at pipsqueak’s shocked expression.

‘Oops, sorry sis,’ Lorraine smiled.

‘Sam has asked me to go on holiday with him,’ Linda addressed her maid. ‘We’re going to Jamaica for a couple of weeks. I’m going to meet his family, isn’t that nice? I’ve asked Lorraine to come and stay here to keep an eye on you.’

‘Don’t look so worried pipsqueak,’ Lorraine laughed. ‘We’re going to have a wonderful time. Not as wonderful as my sister and her lover, but very enjoyable all the same. At least for me. How much you enjoy it will depend on how quickly you learn and how respectful and obedient you are. Make no bones about it, when Linda gets back, I intend to present her with the most humble, obedient and perfectly behaved maid she could possibly wish for. Isn’t that what you want to be?’

‘Yes Miss Lorraine. Thank you, Miss Lorraine.’

‘Good, now lift the front of your skirt and show me what you’re hiding under there.’

It was a definite high point of emasculation for pipsqueak, standing in front of his sister-in-law holding up the skirt of his sissy maid uniform while she tormented and teased him without mercy.

‘Is that it? Why is it locked away?’ asked Lorraine. Of course, having discussed the poor maid’s chastity at length with her sister, she knew exactly why, but that was no reason to pass up the chance of having some fun at the wimp’s expense.

‘Answer my sister pipsqueak,’ Linda demanded.

‘Because Mistress Linda has no use for it, Miss.’

‘Hardly surprising going by the size of it,’ Lorraine smirked. ‘I bet if it wasn’t locked away, you’d be playing with it at every opportunity like the sad little pervert I always told my sister you were?’

‘Yes Miss Lorraine, I mean no Miss Lorraine.’

‘Well, which is it? You would or you wouldn’t?’

‘I… I don’t know, Miss Lorraine,’ the confused sissy curtsied in apology.

‘So why is it so small? I’ve never seen one that small except on a baby boy.’

 ‘I don’t know Miss Lorraine.’

‘Did you not see this before you married the wimp sis?’ she asked pipsqueak’s wife who was laughing so hard tears were rolling down her face. ‘I can’t believe you would have married it if you’d known it had a clitoris instead of a cock!’

That had them both in fits of laughter.

‘Put your skirt down pipsqueak,’ Linda eventually managed to say. ‘Take Lorraine’s case upstairs and unpack for her. We’re going out for lunch.’

It was an enormous relief for pipsqueak to get away from his wife and her evil sister and hear the front door slam as they left, but hugely frustrating to have to unpack her case. Her clothes looked expensive and felt amazing. It was the smell though that truly drove him insane. Rubbing a pair of her silk panties against his cheek he held one of her sexy high heeled stilettoes over his mouth and nose, breathing in her scent before sticking out his tongue to lick the insole of the shoe where he knew her tiny delicate foot had been.

‘What the hell are you doing?’ Lorraine screamed from the doorway making pipsqueak jump and drop her shoe. ‘Linda, come here quickly!’

‘What’s wrong?’ Linda asked.

‘It seems your supposedly eager to please maid is just a sad little pervert after all. I just caught her manhandling and drooling over my shoes and underwear.’

‘How could you?’ Linda demanded of the cowering pipsqueak.

‘I’m sorry Mistress, it… I just…’

‘I don’t want to hear it!’ Linda screamed at him. ‘You’ve embarrassed me in front of my own sister!’

‘It’s your fault!’ he wanted to scream back at her. ‘You keep me locked in this damned cage for weeks on end, teasing and frustrating me until I’m insane with pent up lust! Then you put me in a situation where I have to handle your sister’s underwear! What did you expect?’

In reality though, he didn’t say any of that. He just stood, head down staring at the floor.

‘Apologise to my sister right now you fucking pervert!’ Linda demanded.

‘I’m really very sorry Miss Lorraine. It won’t happen again, I swear!’

‘You got that right!’ Linda yelled before walking over to him. ‘Get your head up!’ she shouted and spat in his face. ‘Lorraine, come here. It’s only fair you get to show this worthless creature what you think of her.’

With a contemptuous look of superiority and triumph Lorraine sidled over and spat, not once, not twice, but three times in the cringing pipsqueak’s face.

‘Now go to your room maid, you can stay there until we get back. And don’t think this is over, it’s not!’

Having not dared to wipe his face, the spit was dripping from it and landing on the front of pipsqueak’s uniform as he knelt in punishment position hands on head inside the little cloakroom cupboard that served as the maid’s quarters. When the door opened and he saw his beautiful wife glaring in at him he couldn’t help himself, he began to sob.

‘You can save the tears for when we get back from lunch you little slut! You are going to beg Lorraine to put you across her knee and teach you a lesson. And when she’s finished, I’m going to take my slipper to you for messing up the front of your new uniform.’

‘Yes Mistress,’ pipsqueak sobbed. ‘I didn’t mean to be a pervert, honestly. I thought you’d gone and I… ‘

‘Oh, so you’re not sorry for what you did, just that we caught you!’ Linda could hear Lorraine giggling behind her out of sight of pipsqueak. The whole thing had, of course been planned, but no need to tell her sissy husband that.

‘No, no Mistress, I didn’t mean that. I just meant I’m sorry. I’ll do anything to make it up to you and to Lorraine, anything I swear!’

‘Miss Lorraine!’ Linda reminded him.

‘Miss Lorraine,’ pipsqueak blurted. ‘Please Mistress, please let me make it up to both of you!’

‘Why should I? After all I’ve done for you, you can’t even manage to show a little respect for my sister. Instead you have to embarrass me by behaving like a sexy starved pervert!’

‘I’m sorry, honestly, I really am Mistress! I do respect your sister, I swear! If you could just give me one more chance to prove it.’

‘If I give you that chance, you’d damn well better make sure you don’t let me down again pipsqueak!’

‘I won’t honestly Mistress, I… ‘

‘Shut up! Shut your stupid slut mouth! From now on you treat my sister and I like we are goddesses. You do everything you possibly can to please us regardless of the cost to you. You give yourself body and soul to us. You obey every instruction like your life depends on it. The more unpleasant, the more frustrating, the more humiliating and the more painful it is for you the more grateful you are and the more you smile and thank us from the bottom of your heart! Have I made myself clear?’

‘Yes Mistress,’ he blurted forcing his expression into a smile as the two women’s spit continued to drip from his face.

‘Clear enough for even a pathetic little faggot who loves dressing in sissy outfits but can’t satisfy his wife like you to understand?’ Linda joined in, appearing from behind her sister.

‘Yes Miss Lorraine.’

‘Say it!’

‘Clear enough for a pathetic little faggot who loves dressing in sissy outfits but can’t satisfy his wife like me to understand Miss Lorraine. Thank you, Miss Lorraine!’

‘Clear enough for a sad, sex-starved little pervert who gets off on sniffing and licking ladies’ shoes to understand?’ demanded Linda.

With tears of shame mixing with the spit running down his face, Pipsqueak repeated and confirmed his agreement with his irate wife’s accusation.

‘Do not move from that position until we get back!’ Linda advised her husband coldly before slamming closed the closet door.

As he heard the front door open and close and the happy sounds of his wife and sister in law’s chatter faded, pipsqueak began to wonder what he’d got himself into. No… what he’d allowed those two dominant beautiful bitches to manipulate him into.

‘I love telling him he’s going to be punished and then leaving him to fret over it,’ Linda told her sister as they climbed into the car that used to belong to her husband but was now, like everything else, in her name. ‘It gives me such a warm glow!’

‘I think I can guess where the warm glow is, you cruel bitch!’ Lorraine laughed.

‘I’m not cruel,’ Linda pouted. ‘I’m just a beautiful, sexy, high maintenance wife!’

‘Can I really spank him when we get back?’ Lorraine asked excitedly. ‘I’ve never spanked a man before!’

‘Of course, you can sis,’ Linda smiled. ‘You can do whatever you like to her. My sissy maid is your sissy maid. In fact, she’s long overdue for relief, how would you like to ruin her orgasm for her?’

‘Hell yes!’ Lorraine cheered as she clapped her hands.

‘But one thing Lor… she’s is no man. I don’t think of her as one anymore and neither should you.’

They both laughed as they drove away.

On their return, giggling and a happy from the expensive chilled champagne they’d had with lunch, the two beautiful sadistic ladies took great delight in subjecting their helpless prey to several painful spankings, taking turns to see who could make her squeal and beg the loudest. When they paused to recover from their exertions, more wine was respectfully served by pipsqueak while his wife regaled her sister with tales of her black lover’s prowess in the bedroom. In between serving wine the hapless maid was employed either to lick the feet and suck the toes of one or other of the gorgeous inebriated ladies, lie on the floor, open mouth acting as a target for the spit they took turns firing from their sexy lip sticked mouths, or else being mercilessly questioned by his sister-in-law about his failures as a husband and a man.

When the ladies finally tired of their game, pipsqueak was sent to fetch the stomping stage. The idea of being teased and abused by his wife under the soles of her shoes while her sister watched was deeply humiliating but incredibly exciting at the same time and the reality did not disappoint.

Linda was wearing a very sexy pair of black velvet mule slippers that really brought out the contrast of her dainty naked red-painted toes. Having her sister as an audience really brought out the bitch in Linda as she tormented poor pipsqueak with the soles of them.The underside of his rock-hard bobbing penis being rubbed up and down until he was sure his giggling wife would let him cum only to have her switch to kicking and stomping while he begged and pleaded for mercy had poor pipsqueak delirious with pent-up frustration. The icing on the cake came though when Linda invited her sister to join her.

There was barely enough room for them both on the wooden platform and they had to hold onto each other’s waists to avoid falling off. Lorraine was wearing mule slippers too but hers were red and she was wearing nylon stockings with reinforced toes through which pipsqueak could just make out the darker red of her painted toe nails.

Having two beautiful women tormenting and teasing his bruised and battered but still rock-hard cock was almost more than the poor sissy husband could take.

‘How do you know when to stop rubbing?’ Lorraine asked her sister as she toyed with pipsqueak’s penis with the tip of her slipper.

‘Just watch her face,’ Linda laughed, ‘it’s a dead giveaway!’

‘You’d better warn me anyway,’ Lorraine giggled, ‘I don’t want to let the little bitch cum by accident.’

‘Don’t worry Lor,’ Linda assured her sister. ‘If you go too far and it starts to cum just stomp down on it, the little slut hates that, don’t you slut?’

‘Yes Mistress,’ pipsqueak moaned. ‘Please Mistress, please may I cum, please!’

‘Nope,’ Linda casually replied.

‘Can’t you make him… I mean her, warn you when she’s getting close?’ Lorraine asked. ‘You know, sort of force her to be complicit in her own torment!’

‘What a great idea,’ Linda laughed. ‘Pipsqueak, you heard my sister. You will warn us if you get close to having an accident. If you don’t you will regret it, I mean it!’

‘Yes Mistress,’ pipsqueak moaned. ‘Please Mistress, I’m close now!’

The girls immediately stopped their teasing and stood smiling down at their hapless victim as he panted and begged, ‘Please Mistress, please!’

‘What a fucking pathetic spectacle you are pipsqueak!’ Lorraine taunted him. ‘Some husband are you? What the hell my sister ever saw in you I have no idea.’

‘Oh, poor pipsqueak!’ Linda laughed. ‘Is my nasty sister being cruel to you again? Never mind, I’m sure she likes you really.’

‘Yea, of course I do,’ Lorraine smiled. ‘I have nothing but respect for a man who dresses as a woman 24/7 and runs around doing endless housework hoping to please his sexy wife. A wife who sleeps around with another man right in front of him and even makes him suck the guy’s cock! What’s not to respect?’

Linda nearly fell off the stomping stage as she laughed.

When she managed to get back on she started rubbing the sole of her slipper up and down pipsqueak’s penis again. ‘Time to tease you again, sorry baby, I know you must be going crazy down there looking up at our sexy legs. Which one of us do you think has the best legs? And which one has the sexiest feet?’

‘Please Mistress, you’re both beautiful, both the best, please Mistress, I can’t stand it, please!’

‘Poor baby, you must be so desperate! Would you like me to keep going just a little bit longer, so you can have a nice cummies? So you can show my sister what it looks like when a sissy cums for her Mistress.’

‘Yes! Oh, yes! Yes please! Please Mistress! I love you so much!’

‘What does that have to do with it?’ Lorraine demanded as she lifted one slippered foot from the platform and pressed it against his face. ‘Is she supposed to take pity on you and let you have your pathetic little dribble just because you love her?’

‘Please Mistress Lorraine!’

‘Please Mistress Lorraine!’ Lorraine mocked him in a high-pitched voice. ‘Please what faggot?’

‘Please may I cum Mistress Lorraine?’

‘If it was up to me, you’d never cum again,’ Lorraine spat. ‘My sister is far too lenient with you. You take advantage of her you disgusting little sissy!’

‘What?’ pipsqueak’s mind screamed, ‘I take advantage of her? You must be fucking joking!’ But he didn’t dare say it out loud, he was getting close again! ‘Please Mistress, I’m close, please don’t stop! I’m begging you! Please!’

But stop she did and as her sister stepped down to retrieve her glass of wine, Linda squatted down, still on the wooden platform.

‘How do you like being stomped by two ladies instead of one honey?’ she smiled down at her husband.

‘Please Mistress, I can’t take it anymore! Please let me cum. Let me cum properly just this once, so I can show you how much I love you, please!’

‘Hey sis,’ Linda called out. ‘My maid says she can’t take any more. What shall we do?’

‘Well,’ Lorraine smirked as she sidled back over, the condensation running down the outside of her glass of chilled wine. ‘We could always snuff the little bitch and put it out of its misery, I suppose.’

‘Great idea,’ Linda declared as she dismounted the stage, positioned herself over her husband’s face and plonked herself down shutting out the light.

Lorraine meanwhile, stepped onto the stage and began to manipulate the sissy’s penis with the sole of one sexy slipper causing pipsqueak to moan desperately into his wife’s pantied crotch. Linda lifted slightly and sat on her sissy maid’s chest, looking down into his eyes.

‘Please Mistress, I love, I can’t stand it! I need to cum so badly, it’s been so long! I’ll be good I promise, I’ll do anything you say, I swear!’ he whispered as his eyes filled with tears.

‘I know sweetheart, I know.’

‘Please can I cum Mistress, please!’

‘Sorry honey, that’s not up to me. Little sis is in charge today and, just between you and me, I think she’s a bit of a bitch.’

‘Please Miss Lorraine,’ pipsqueak begged, in tears, ‘Please may I cum, I’ll do anything you say but please, I can’t take any more!’

‘You can cum pipsqueak, ’Lorraine said. ‘But you do it when I tell you, not before and not after, got it?’

‘Yes Miss Lorraine, thank you, thank you, thank you!’

‘Tell me when you’re right on the edge sissy,’ Lorraine said. ‘I’ll give you a count of five after you say you’re there. If you cum right on five I’ll keep rubbing and you can come properly. If you let go early I’ll stomp on it and block it. If you don’t cum on five I’ll stop and it’s over. Understand?’

‘Yes Miss Lorraine, thank you Miss Lorraine.’

‘That’s my good gurl,’ Linda soothed her husband, stroking his cheek lovingly. ‘I have a special treat for you too,’ she smiled as she pulled off her slippers and plonked her bare feet onto his face. ‘Lick them.’

That was all it took to start the pent-up spunk bursting from pipsqueak’s painful blue balls. ‘Please Miss Lorraine, I’m there!’

‘Good gurl,’ Lorraine smiled. ‘Five, four, three… ‘

‘Just two seconds! Fuck, two seconds, come on! Don’t fucking cum yet!’ pipsqueak’s mind screamed.

‘Two and a half, two, one and a half, one, a half… now! Cum now faggot!’ Lorraine screamed.

 ‘Aaaaaaarggggghhhhh!’ pipsqueak squealed as he kissed and licked the bottoms of his wife’s feet, unable to do anything to help himself.

‘NooooooooaaaargggghhhNOOOOOOPLEEEEASE!’

Lorraine laughed as she pressed down her sexy slipped foot pinning pipsqueak’s erection to the wooden platform.

‘You promised!’ pipsqueak gasped in horror as his wife’s heartless sister lifted her foot and, hands on hips, watched the backed-up spunk flow from the end of the crying sissy’s now soft penis.

‘Promises to sissy maid husbands don’t count loser!’ Lorraine laughed.

Pipsqueak looked into his beautiful wife’s smiling face desperately seeking moral support for the outrage done to him. ‘She promised,’ he mumbled.

‘Sorry baby,’ Linda laughed. ‘Like I told you, my sister’s a bitch, what can I say? It runs in the family.’