The Willing Cuckold

For Sam’s next visit he and Linda had devised a devilishly exciting (for them) and torturously humiliating (for pipsqueak) plan. Just like last time Linda had her sissy maid working her girly socks off making sure the whole house was immaculate for her lover’s visit. She dressed him in the same ridiculous sissy maid outfit too but that would not be where the humiliation ended.

Firstly, pipsqueak would be reading out loud to Sam and her, the letter she had instructed him to write. Then, as if that would not be devastatingly embarrassing enough; he would be performing for their amusement, a little song and dance routine she had been making him practice every night. There had been a lot of pleading and begging and even tears over that. In the end though, as always, Linda got my way.

‘If this is going to work, you really must stop thinking of yourself as a man, certainly as my man,’ Linda explained one night after pipsqueak had thrown a little tantrum that earned him a trip over her knee for a prolonged hairbrush spanking. ‘Sam is the man of this house now. You are our sissy maid. Get that into your head; you are not a man but not a woman either. You are a thing. A possession. Something to be used and abused as either of us see fit. The sooner you accept that, you stupid gurl, the easier this will all become for you and the less sore your sissy bottom will be.’

On the night in question, Linda made pipsqueak stand in front of a full-length mirror in the hallway for half an hour, staring at himself, taking in how ridiculous he looked and practicing his little routine. To give him his due, he really did try his best, even though she mocked him and laughed at him openly, ‘Wow, what a hunk I married,’ she taunted. ‘You must be so proud of what you’ve become. You really are every woman’s dream, aren’t you?’

‘Yes… I mean no Mistress,’ he simpered pathetically. ‘Please Mistress, I do it for you to prove how much I love you. I do everything for you, to make you happy!’

Linda had come to the realisation some time ago that, the more her husband gave up for her, the more he submitted to her increasingly unreasonable demands, then the harder she wanted to push him and the more unreasonable and demanding she felt she wanted to be. She couldn’t help it. She demanded absolute obedience and simpering sissyhood, but when she got it, it was like a red rag to a bull. She simply could not believe what a sadist she had become. It was just as well that her ever-growing desires to dominate her poor pipsqueak were matched by his ever-growing desires to be dominated. They were perfectly in sync, in a symbiosis of Mistress and slave that excited them both so much it took their breath away!

‘Don’t give me that, you do it because you’re a pathetic excuse for a man who gets off on dressing as a sissy and being ordered about by his wife! Now let me see the little song and dance one more time, but this time use a high-pitched girly voice. With a sexy little lisp too,’ Linda smirked. ‘Don’t just stand there gawking at me gurl! Go ahead, do it! If it’s not perfect I’ll take my crop to the backs of your legs!’

The poor dear, he tried so hard, all red-faced and teary eyed, but she whipped him anyway. ‘It won’t do any harm to put you in your place before my boyfriend gets here,’ she told him as she whipped her leather riding crop across the backs of his shaved and stockinged legs. ‘In fact, I quite like the look of those bright red and sore-looking wheals across your legs. Someone in your position should carry the marks of their inferior place in the household. I bet Sam will like them. I dare say, if your letter or your little performance doesn’t sufficiently impress him, he’ll be adding to them in due course. I do hope so. You know how horny it makes me to see him bullying and humiliating you.’

‘Yes Mistress,’ poor pipsqueak answered with a little curtsy.

‘You know I really like Sam, don’t you pipsqueak,’ Linda teased, seeing yet another opportunity to tug his strings.

‘Yes Mistress,’ another curtsy, eyes respectfully cast down at his wife’s feet; How far they had come! How many women could say they, not only cuckold their husband with his full knowledge and complicity, but amused themselves by rubbing it in his face too.

‘I mean really like him. He’s so big and strong, so masculine, so amazing in bed. I feel like a teenager on her first date every time I’m with him. When I’m away from him I miss him so much, I ache to feel him inside me. I want to keep seeing him, but even if it doesn’t last,’ Linda mused, ‘There are plenty more men out there who would jump at the chance to bed a classy lady like me. I’m sure we could soon find one that would be happy to play a role in your subjugation. Whatever happens though, you know you will never be inside me or any other woman ever again, don’t you?’

‘I… I thought,’ Chris mumbled, highly aroused by his sexy bitch of a wife’s teasing but shocked by the idea of never making love to his gorgeous wife ever again. Surely, she was just pulling his strings.

‘You’ll never be a man. After your last embarrassingly inferior attempt, I think it’s for the best that we just consider you a sort of ‘born again virgin’. I wanted you to know that now, so that, if Sam allows you to watch us make love tonight, you can think about what you’ve lost, what you’ll never have again, while he shows you how a real man treats a lady.’

‘Please Mistress… ‘

‘Knowing that you are thinking about it, being acutely aware of how devastatingly frustrating and humiliating that must be for you…you know how that will excite me, don’t you? How it will fuel my orgasm as I wrap my arms and legs around my lover, mash my lips against his and suck his tongue into my mouth? You know it won’t be just his magnificent cock that drives me over the edge and almost makes me pass out as I cum. No, it will be you too, what I’ve done to you, what I’m going to do to you, what you’ve allowed me to do to you, what you ache for me to do to you next.’

‘I love you so much. I worship you. I would do anything, suffer anything, to please you…or even just to amuse you.’

‘Did you notice I’ve started saying Sam and I make love now? It’s not just fucking; it’s gone way beyond that. So, if you really want to please me and amuse me as you say, then think about that fact when you stand in front of us and read your sad little letter and do your pathetic little sissy dance. Can you do that for me pipsqueak?’

‘Yes Mistress. Thank you, Mistress,’ the little sissy maid answered with a wobble in his voice and a final curtsy before she sent him to wait at the door for her lover’s arrival.

Sam was late arriving; deliberately, as he told Linda afterwards. Well aware of how anxious poor pipsqueak would be, he thought it would be amusing to keep him waiting and draw out his torture. When he finally turned up, he made it clear what his priorities were and how little regard he had for the nightmare of embarrassment facing the sissy maid. He made pipsqueak kiss his boots in welcome and take his coat then, as the hapless maid went to hang Sam’s coat in the closet, he told him to stay in there until he was called then closed the door on him.

It must have been a full hour later when Sam called out for pipsqueak to get out of the cupboard and join them in the lounge. There was a strong smell of sex in the room. The lovers had obviously been in such a hurry they had not even taken the time to undress. Linda had unzipped Sam’s flies and he had simply ripped her silk panties out of the way. Linda was still straddling her lover’s thighs, his softening cock still inside her and her pussy leaking some of the huge load he’d deposited inside her, when the gurly servant entered the room, curtsied in front of them and stood to attention, hands clasped in front of her and eyes respectfully down.

‘Your wife tells me you have something you’d like to read to me pipsqueak,’ Sam addressed pipsqueak as he helped Linda off his lap.

‘Yes Sir,’ the sissy responded.

‘Right, well you’d better clean us both up and bring us some cold drinks first, then I’ll give you a couple of minutes before I take your wife upstairs to bed. Apparently, she wants me to give me her ass. I understand you’ve never been there, is that correct?’

‘Yes Sir.’

‘Well, I seriously doubt you ever will now,’ he grinned as pipsqueak looked up giving his wife an anxious glance. Linda smiled knowing how jealous he must be feeling. He’d only ever suggested anal sex once in their marriage and she had made it very clear that she found the idea disgusting. Now here she was freely offering it to another man.

‘Any man can take a woman’s pussy,’ Linda grinned at her sissy maid husband. ‘Well, any real man anyway. But, when a man takes a woman’s ass, he owns her.’

Embarrassed by his wife’s words, pipsqueak knew he had no choice but to kneel to lick Sam’s monster cock clean of their combined juices after which he laid on his back while Linda sat on his face to drain Sam’s thick ropey spunk into his mouth. Then, humiliating duties complete, pipsqueak shuffled off in his heels to get drinks for his wife and her lover while they adjusted their clothing. Then, red-faced with embarrassment, he stood in front of them to carefully read out the letter he’d been made to write, detailing his love and devotion to his wife and his high regard for her lover while they sat holding hands and grinning in cruel amusement.

Sam was itching to get his woman upstairs by then and Linda could clearly see his cock hardening again already through the denim of his jeans. She wanted more though, more of the humiliation and degradation of her sissy husband that she had come to crave almost as much as she did her lover’s rock-hard cock. So, scratching her long, perfectly manicured finger nails along Sam’s impressive bulge, she told pipsqueak to hurry up and show her lover what he’d been practicing in his honour.

Linda wasn’t entirely sure her sissy husband would actually go along with it, or what her lover’s reaction would be if he did. She need not have worried though, as they both performed their roles admirably while she filmed the whole thing on her phone. Poor pipsqueak looked utterly cowed by his self-humiliation and Sam made his contempt very clear. It would have been really hot if Sam had laughed at him but the contempt was even better and Linda could feel the wetness between her legs as she bore witness to this major development in the utter subjugation of her poor pathetic husband. There was no going back now, no possibility of undoing this, not for either of them.

‘You forgot the girly voice pipsqueak, apologise to Sam and do it again,’ Linda spoke into the horribly uncomfortable silence that greeted the end of pipsqueak’s utterly degrading performance. ‘I’m videoing it again so make sure you get it right this time, or else.’

‘The videos and pictures I’ve taken of my sissy husband in all his glory since we began this journey constitute a cast iron assurance of her continued cooperation in her own demise as a man,’ Linda explained to her lover. ‘She knows what will happen to them if she tries to back out of our new arrangement, don’t you pipsqueak?’

‘Yes Mistress,’ pipsqueak mumbled with a curtsy. He’d promised his wife repeatedly that he would never do that but she had insisted that, in order to take their relationship as Mistress and sissy maid as far as she wanted to and as far as he said he wanted her to, she needed an ace up her sleeve, a means to ensure he wouldn’t and couldn’t change his mind or refuse to obey her, no matter what she demanded of him.

Linda knew she would never do the things she threatened; she loved her husband. But she had to convince him that she would, or at least that she might, in order for their relationship as Mistress and maid to continue to develop as they both wanted it to. There had to be a means of enforcement. Pipsqueak had already had to go way outside of his comfort zone and they were only just getting started. There would inevitably be times when he would want to rebel and Linda needed to be able to get them through those times. Sometimes his love and devotion to her would be enough, other times persuasion or the dangling of a carrot would be required, but for some things she would need to be able to threaten her maid with consequences even more unacceptable than the thing he was rebelling against.

‘I thought I understood what a pathetic fucking loser you are,’ Sam addressed pipsqueak when he finished his second rendition. ‘But you are something else! It’s no wonder at all your wife needs to go outside her marriage for sex, is it?’

‘No Sir,’ pipsqueak responded, so quietly Linda barely heard him.

‘Apologise to your wife for being a worthless, waste of space who couldn’t satisfy her. Then thank her for cuckolding you with a real man.’

Pipsqueak obeyed but could not look his wife in the eye as he spoke, so Sam made him do it again, looking straight at her and with a curtsy before and after.

‘Now both of you upstairs,’ Sam ordered. ‘You are going to get the fucking that you’ve been waiting for your whole married life,’ he said to Linda. ‘And you,’ he smirked as he turned to her sissy maid husband, ‘are going to watch and see how the wife you love and adore so much responds to being properly fucked. By a man instead of a fucking sissy!’