The Willing Cuckold

Linda’s first experience of anal sex began with a great deal of excitement mixed with quite a lot of trepidation. Seeing the way her husband’s lips were stretched to their limit to accommodate her lover’s impressive organ made her wonder how her virgin ass could possibly accommodate it. She’d been using a butt plug for a few days to try to get used to the stretching and lots of lubricant helped but it was still painful at first, so painful she twice lost her nerve and begged her lover to stop. Fortunately, as it turned out, Sam was not the kind of man who took no for an answer. He backed off momentarily both times, ordering the worried looking pipsqueak to apply yet more lube. In the end Linda’s tightness was no match for her lover’s determination or his rock-hard weapon and, with a squeal of pain she felt the bulbous head force its way into her body.

Sam was gentle at first, giving her time to become accustomed to the novel intrusion of a real cock into her most private place. As Linda relaxed though, his thrusts became longer, forcing his battering ram of manhood deeper and deeper into her bowels. Gradually the pain turned to pleasure and Linda’s squeals turned to moans, her protests to encouragement. She wanted this, not just for herself but for her husband too, knowing full well the overwhelming effect it must be having on him as he knelt submissively at the side of the bed staring wide-eyed at the love of his life being possessed, on her hands and knees being owned and properly broken in by another man while the sharp spikes inside his chastity tube did their work, denying him even the small compensation of getting a partial hard-on.

When the pleasure sensations became too much Linda’s arms and legs collapsed and she fell forward onto her face, cumming in waves of almost unbearable pleasure. Her lover relaxed his huge arms, falling forward on top of her, pinning her to the bed, their sweat-soaked bodies sliding against each other. Turning her head to look at her sissy husband to make sure he was watching; Linda moved her hands to cover those of her lover as they lay flat on the bed either side of her head. Entwining her tiny delicate and perfectly manicured fingers with his much larger ones, she begged Sam to cum inside her, to own her.

For his part Sam had never felt anything so soft and tight as the sexy ass that gripped his penis, seeming to milk it desperately. He felt relief that his conquest wanted him to cum now as, despite his experience and prowess he knew he could not last much longer. So, burying his face in Linda’s long dark silky hair, he bellowed his triumph as he unloaded what felt like a gallon of thick ropey spunk so deeply inside her he half expected to see it erupt from her mouth.

‘I own you now baby!’ the huge black conqueror gasped.

‘Yes!’ Linda laughed. ‘Yes, you do, you really do!’

‘You!’ Sam yelled at pipsqueak, making him jump. ‘Look on the dressing table, your wife left the key for your chastity cage there. Unlock your little embarrassment and kneel in the corner facing the wall. Get my underpants too, put them over your head and find your wife’s panties, you can use them to jerk off into.’

Still in a state of shock at the emotionally devastating scene he had just witnessed, but also hardly believing his luck and desperate not to do anything that might change Sam’s mind, a timid and nervous pipsqueak rushed to comply. It seemed to take an age to remove the cage as he had to unscrew the spikes before he could unlock it and slide the hated tube off his bursting cock. The embarrassment of wearing his wife’s lover’s underpants over his head and the disgusting smell of cock they gave off paled almost into insignificance as he felt the soft silk of his wife’s panties against his bobbing cock. This was what weeks of chastity and teasing had reduced him to and the awareness of that fact had him instantly erect.

‘How long should we give it to dribble its slime?’ he heard Sam asking Linda.

‘Probably about thirty seconds will be enough I should think,’ she answered and they both laughed.

‘Alright pipsqueak, you heard the lady. You have exactly thirty seconds then you leave go of that little thing no matter what. Do not disobey me or you might never get another chance. Got it?’

‘Yes Sir, thank you Sir,’ pipsqueak squeaked.

‘Go!’

Thirty seconds went by in a flash and when the poor little wanker heard ‘Stop!’ it required such a supreme effort of will to remove his grip that he swooned and almost passed out. He hadn’t cum! It wasn’t enough time! It had taken most of the thirty seconds to get past the unconscious conviction that getting hard would be punished by the spikes. He hadn’t cum, he hadn’t fucking cum…. then suddenly, as he stared down at his knicker wrapped erection, it began to jump and a wet patch began to form inside his wife’s discarded knickers. He was cumming! After almost eight interminably long weeks of denial, he was finally draining his swollen blue balls.

His groan of release soon turned to one of despair as he realised there were none of the sensations he’d hoped for and dreamed of for weeks. No spurting, no orgasmic waves, no mind-blowing explosion of release. No. Just a couple of weak spurts and then a slow dribble. He had ruined his own orgasm!

‘Get that cage back on faggot!’ Sam yelled at him. ‘Your wife shouldn’t have to look at that pathetic excuse for a cock. It will just remind her of how many years she wasted on it. And make sure you screw those spikes right in! Then get over here so your wife can check it’s locked away properly.’

‘Well pipsqueak,’ Linda smiled up at her husband as she lay back in her lover’s arms. ‘Did you enjoy your little ruined sissy dribble?’

Staring down under the underpants still on his head at his once more securely caged manhood (could it even be called that now?), his wife’s cum soaked panties still held rolled up in his hand, pipsqueak realised his conundrum. If he said no, he had not enjoyed it, either his wife, her lover or both of them might take his answer as a sign of ingratitude and sentence him to an even longer period of chastity to teach him a lesson. But if he answered yes, he had enjoyed it, that might give them carte blanche to ensure all future orgasms were ruined too.

‘Answer you wife, pipsqueak,’ Sam growled.

‘I…I’m not…I mean it was…thank you Mistress, thank you Sir.’

‘Fucking loser!’ Sam sneered.

‘Don’t be so cruel you big bully!’ Linda laughed as she playfully slapped her lover’s thigh. ‘Don’t listen to him sweety, you did very well. Now you’d better pop those panties in your mouth. You can suck them clean while you run off to get Sam and I some nice cold drinks. And keep Sam’s underpants on your head, it’s a good look for a sissy.’

The sound of the front door slamming closed woke Linda from a deep and satisfying sleep. Waking to find her lover gone, she rose, slipped on her fluffy white dressing gown and the cute little fluffy slippers with tiny stuffed teddy bears attached to the tops that Chris had bought her for her birthday and slowly she descended the stairs. Her intention was to tease her husband about the latest developments in their female led relationship, his ruined orgasm and her cuckolding of him, but she could not find him.

After calling his name several times she thought she heard a muffled answer coming from the hallway. After calling him again Linda finally traced his voice to the cloak cupboard. Opening the door, she burst out laughing at the pathetic sight that greeted her. Poor pipsqueak was kneeling facing her, still in his sissy outfit but with a crudely made cardboard sign hanging around his neck. The sign read ‘I Am A Worthless Sissy Who Can’t Satisfy His Wife’.

‘Well,’ laughed Linda, ‘I can’t accuse you of false advertising, can I? Come on out of there.’

‘I can’t,’ Chris responded. ‘Sam… I mean Mr Sam said I had to stay in here on my knees until he calls and tells you to let me out. He said if I disobey him, he won’t be back and you will never see him again. He said you would blame me for that.’

‘He’s right, I would,’ Linda answered. ‘Oh well, see you later then pipsqueak,’ she smiled as she closed the door leaving him in darkness once more.

Sometime later a flushed looking Linda opened the closet door again, ‘Your master said you can come out now, you little sissy. I just need to take your picture first. There, now out you come. I just finished talking to him. We had phone sex; I’ve never done that before, not even with you. It was very exciting!’

As pipsqueak rose unsteadily to his feet, Linda was staring thoughtfully into the cupboard behind him. ‘You know, you’ve given me an idea. There’s actually quite a lot of room in there isn’t there? Almost enough for you to lie down flat. I think it would make a nice little maid’s bedroom. After all, the way things are going, we can hardly have you sleeping with me in my bed, now, can we? It would be entirely inappropriate, not to mention very disrespectful to my lover and confusing for you. And the spare bedrooms are far too nice to waste on a servant. No, you need to know your place, I need my privacy and Sam needs to be reassured that there won’t be anything inappropriate going on behind his back.’

‘But I’m your husband,’ pipsqueak moaned, somehow hanging on to the idea that gave him the right to expect some sort of preferential treatment.

‘Precisely,’ Linda agreed. ‘You are my sissy husband and Sam is my lover. So, he belongs in my bed and you belong in the cupboard, now the maid’s room. The subject is closed. You can move your things out of my room tomorrow and store them in the smallest spare bedroom. I’ll allow you to use that as a dressing room but I don’t want you sleeping in there. Now you’d better tidy the lounge and the kitchen then you can get yourself off to bed. I’m sure you can find time tomorrow to make yourself a nice little bed in there but, for tonight, the floor will have to do.’

‘Please Linda,’ pipsqueak tried to break through to his wife of over twenty years. ‘I don’t want to sleep in there on my own. We’ve never slept apart before; we should be together. I love you.’

‘I love you too,’ Linda answered coldly, ‘But if you think I’m going to sleep in a cupboard you are sadly mistaken.’

‘You know what I mean,’ snapped pipsqueak, ‘I mean in bed, in our bed.’

‘There is no ‘our’ bed, not any more. In case you haven’t noticed my darling husband, I have a lover now, a boyfriend. Just like you wanted me to, yes?’

‘Yes but…’

‘No buts! This is your life now; I suggest you come to terms with it. You have been demoted. You are no longer the man in my life. I like having a maid and I want it to be you but it doesn’t have to be. You know as well as I do that there are plenty of ownerless sissies out there who would happily take your place in a heartbeat. Shall I make some enquiries?’

‘No, no, I don’t want you to have someone else. I want to be your maid; you know I do!’

‘Then I suggest you spend the first night in your new room coming to terms with our new relationship and your place in my life. Now get out of my sight! Oh, one more thing before you go. If you ever fail to address me properly as Mistress in future, including with a submissive curtsy, I will tie you down and have my lover use a cane on your sissy backside instead of his belt. Is that clear, maid?’