Saturday, November 18, 2023

The Story of Elaine, Jackson and cuckold james

Chapter Eighteen - Alana

 


Warning - this chapter depicts sexual intimacy between Master and cuckold.


It was Friday morning and I was still asleep when I felt the bed move as Elaine, my Wife, clambered over me to go to the toilet, leaving me and Jackson alone still in a post sexual languor. I had spent much of the last night acting as sex slave to Elaine (who I now routinely refer to as Mistress) and had learned that I was far from alone in my cuckoldry in just the small row of houses where I live in Blackheath South London. It's funny the things you recall when still only half conscious.

Slowly my mind cleared as I remembered what had transpired the night before. I recalled kissing Elaine as Jackson had made love to her, I recalled almost calling Jackson 'Master' in the same way as did Elaine and I recalled my cleaning of her pretty pink labia of his semen. Other than that, my mind was still a blur - late nights tend to effect me that way. But there was at the back of my mind telling me that something had occurred last night that had changed our three cornered relationship.

I had done everything that I could to manage the situation since that last Sunday when I had seen Jackson take Elaine under that tower of that beach on the South Coast; this included purchasing a restraint for my little penis. I then left the pair of them alone in my house and received a soaking from the summer rain that night when I had stealthily crept back into the house and found that it was no surprise because I had been outguessed. And last night, Thursday night, I had laid out the bed for them and then joined them and acted as a slave to them. Effectively, my so called management had been that of the 'if you can't beat them - join them' philosophy. But something had changed last night; 'What the hell was it?' I thought, while still half asleep.

The story leading up to this point can be read (Chapters One to Seventeen) can be read by clicking on the link [here].

Little by little, the night's activities came back to me. I could recall sitting at the window and Mistress (Elaine) telling me about my next door neighbours; a couple living on one side of my house (Sheila and Jack) living as 'Black Owned' by their lodger Mr Obinga, and the other couple (Gwen and Charlie) who lived the other side were 'Party Slavers'. It was such a shock to me, so I guess that was why I recalled it first.

Party Slaver


Next came the delicious memory of attending to Mistress's sweet pussy after Master (sorry - Jackson) had released the heavy streams of his seed into her vagina. His ejaculate had not been a problem for me as I had tasted and swallowed the salty, musty cream before and with a sudden realization I understood just why I it was acceptable to my palate. In all truth, his sticky and warm essence is not particularly tasty but what was truly a joy for me was the concept of  'serving' Mistress and the better man than me, and accepting the demeaning nature of my activity. I knew that it would not be long before I would kneel before my Wife's Lover and call him 'Master'. 'But what was it that had happened last night?'

My addled brain was still withholding that 'special' memory, when the bed moved again and Mistress rejoined us, "Roll over cj," she said quietly to me, "I need your special magic again."

Turning over onto my back I looked up to see her lovely pussy descending onto my face. With her legs  stretched out a little further than usual she had allowed my arms and hands to remain free so without any further encouragement from her I reached up to stroke those lovely firm breasts and tweak the coral pink nipples that I had sucked while Master had ploughed his rock hard manhood in and out of her in a gentle but in such an unrelenting way.

But wait! That's not right. He had stopped occasionally, when late into the night Mistress had hooked her upper leg over his and he had taken her from behind while they lay on their sides together - and they had done this for my benefit. It was coming back to me now. Mistress had pushed my hand down to her mound while Master's rod was still embedded deep inside her - and then? With a rush I recalled all that had happened - she had pushed my hand down onto Master's big heavy balls. Not just once but twice, and at the third time I had gone there myself without encouragement from her. For the first time in my life I had touched another man's sexual parts and instead of being scolded or worse he had commented that it was, "nicely done cj."

As Mistress's much welcome labia came into contact with my lips I knew that the 'training' that they were now clearly putting me through was going to progress at a faster rate and although I had initially resisted my journey down the cuckold's path I now couldn't wait for it to proceed apace. So like the willing slave that I was, and still am, my tongue started to work on Mistress's swollen lips, with the memory of another man's balls in my hand still fresh in my mind. 'Pervert!' Was my amused thought as a little taste of Master Jackson's semen settled on my tongue.

This was sheer heaven to me! To be lying naked with my little penis caged, totally subservient and subjugated like a slave to be used at his Mistress's pleasure. The more I licked and swallowed, the more aroused I became; my small penis was now so tight inside it's little restraint it was starting to hurt. It was with some surprise that I became aware of the bed moving again as I felt Master Jackson rouse himself and kneel on the bed with his knees either side of my own.

Although I could not see him, I felt him lean forward and start kissing Mistress and, like the good cuckold I had become, I continued to work diligently on her labia and her clitoris. Everybody was having a nice time and the room was silent as three highly sexed young animals fulfilled their obligations to each other.

Such was my disconnect from reality that it was moments before I realized that something heavy was in contact with my groin, 'What the hell is that?' I thought, my mind still fuzzy from sleep and arousal. I removed my right hand from Mistress's perfect breasts and reached down to try and find out what it was.

I put my hand down on the mystery object and found it to be warm and soft, and as I moved my hand up and down its length I realized that it could only be one thing - it was his big penis. His thick, dark manhood was laying up the side of my plastic cage with its bulbous glans resting gently on my lower stomach. 'Oh Christ! It's Master's cock.'

In shock, I tried to snatch my hand away but instantaneously Mistress's hand closed down on my own; it was then that I knew that this was no accident. Once again, she interlaced her fingers with my own and gently moved my hand up and down the warm soft length of flesh, pausing only to wrap my hand around the large round head just to make sure that I fully understood exactly what I was being allowed to touch. 'Its the 'Rule of Three again,' I thought as she allowed my hand to move away. But only for a second or two as the two Lovers above me (a highly symbolic disposition, given my acceptance of their dominance over me) kissed again.

As before, her cool little hand descended over the back of my own and eased down onto his now thickening penis. And as before, lingering a little longer this time she moved my hand in such a way as I was now stroking it for him - from pubic hair down to his glans. I was stroking another man's cock and as conflicted sexually as I was, I was actually enjoying the act. 'It's that serving thing again,' I thought dimly as I appreciated the soft strength of his now hardening cock.

Mistress took my hand away and did nothing further except continue kissing Master and easing her clitoris up and down over my nose. The 'Rule of Threes' requires every cuckold to try something twice (or is it three times? I couldn't remember but it didn't matter because I knew what was expected of me) before making up his mind whether he would do it without being told or encouraged to, so I understood clearly what was required. It was my decision; was I going to voluntarily stroke Master's cock for him? It was a big step for a man to take, even a cuckold like myself. It would bring my sexuality into question and I would never be the same man again. But the questions were irrelevant; I had allowed myself to be taken down a path and there was no going back now.

I lowered my hand down onto his member that felt stronger, harder and, dare I say it, more manly than my own. With delicate strokes I now explored that big hard rod as it rose from my body to stand hard and upright. I brought my other hand down from Mistress's breasts and felt for his large testicles, they were heavy and starting to harden as my ministrations of his member started to take effect. Slowly at first his body started to move so as to push his manhood through my fingers that were now flickering over his rod and his bell end. He was fucking my hand and the soft groans emitting from his throat bore witness to his impending release.

His thrusting increased and it was clear that 'Master' was enjoying what I was doing for him; he also knew exactly whose hand was pleasuring him intimately. It was the "Oh yes!" that came from his throat that was the signal for Mistress to move away and sit to one side. She had heard that little phrase from him many times and knew exactly what was about to unfold.

His testicles tightened and his cock suddenly jumped in my hand as a stream of creamy white ejaculate shot out from his penis and landed with a 'splat' on my face. It jumped again and his seed landed on my throat and chin. Again and again his rod spat out prodigious amounts of his seed everywhere - into my open mouth, my chest, my tummy and finally the last dregs onto my plastic penis cage. I was once again degraded and humiliated by these two who now knew that they had a cuckold who would do anything for them.

My feeling of humiliation lasted just seconds as I glanced up and saw Master Jackson looking back down at me with a broad smile on his face. "You get better and better, cuckold james," he said, using the full name he had given me, "but I think it's a bit late in the day, so we had better go downstairs and get some breakfast."

His 'commonplace' words brought us back to reality and as they put on their dressing gowns I went off to the shower to clean myself up, but only after rubbing his jism all over my face and body as an overt demonstration of my acquiescence, and to prevent it dripping from me onto the floor. 'What a start to the day. What else is about to occur?' It was a rhetorical question but I knew that my 'journey' had not finished for that day.

The remainder of Friday was spent lazily eating and drinking and tidying the place up for our guests that evening, Bruno, Madeline and my best friend Alan. We did not speak much about what had happened in the bed that morning (which is unlike Master Jackson) but when I did speak I made sure that I addressed Elaine as 'Mistress' and him as 'Master Jackson'. By that level of deference I was signalling that my total capitulation to him would be sooner rather than later - and it pleased him.

It was eight o'clock that evening when the bell rang on the front door and I went to open it. "Hi cj!" said a clearly pregnant Maddie ('Slut') as she brushed past me, closely followed by a large Black Man with a round shaven head, "and this is Bruno," she continued as she dragged him up the hallway and then wrapped her arms around a happy and smiling Elaine.

"Hi I'm Alana," said a voice below me on the front door step. Looking down I saw a very pretty blond, short haired young woman in a red dress. I was taken aback but I did not say anything but bade her welcome as she moved past me to join the others. I remained where I was with the door open.

"What are you doing cj?" asked Mistress after she had extricated herself from Madeleine's hug and kisses.

"I'm just waiting for Alan," I replied.

"I'm already here James," said Alana, "it's me! Alan!"

'What the fuck?' I spun around to look again at the pretty blond. "Alan?" I exclaimed loudly and then remembered that I was supposed to be the timid cuckold, "you're a Woman." I said lamely.

"Well spotted Detective Inspector!" she replied with a nervous smile on his face.

I closed the door behind me and looked once again at Alana, "I guess that you and I have a lot to talk about," I said as I ushered the other four into our Front Room and her and me into the kitchen.

"Alan!" I said but was interrupted.

"Alana please!" she responded with a sudden passion.

"Sorry!" I replied, "Alana then. Now I am going to sit here and shut the fuck up while you tell me what the hell is going on with the guy who is my best mate and who goes with me to the football every other Saturday."

Alana did not have a chance to speak because Mistress, with a sardonic smile on her face, brought two glasses of wine in for us both, "You boys need to talk," she said. But when she had gone it was if a damn had burst. He needed to speak to someone of a like mind or who was in a similar position.

"I hear that Jackson and Elaine are calling you cj now," she said after delicately sipping her wine, "and I know just what has been happening to you since Sunday. Elaine and Maddie talk on the phone every night, and it's mostly about you."

"So?" was my terse reply, which seemed to irritate her.

"Then I guess if there was anyone who wouldn't stand in judgement on me it would be my best friend." she replied tersely. "Especially one who is a fellow cuckold like me."

"I'm sorry Alana," I replied, "this is a bit of a shock. So bear with me and please continue."

She smiled at my emollient tone and took in a deep breath. "This is my way of handling the way my life has been turned around cj," she said, reminding me once again that I am a cuckold too, "and please make no mistake, it is very much to my liking."

Alana looked at my aghast face and continued, "If you think about it I can be exactly what I would like to be, now that my Master has taken over our lives. I can go to work, the pub and the football as Alan and when I get home I change and become Alana."

"I take it that 'Master' is Bruno then?" I asked.

"Exactly!" she replied. "And for someone who said he would 'shut the fuck up', you seem to have a lot to say."

"Ooh Sorry Dear!" I replied laughing - at which I was relieved to see Alana smile at my sarcasm.

"There has always been this side to me cj," he continued 'cuckold reminder again'. "I don't show it at work or anywhere else but at home, that is until tonight in your house. When Maddie took up with my Master I did not know how to handle it. I was depressed, tearful, and suicidal even - for weeks. Maddie was terribly worried, that is until she brought someone to the house to talk to me. His name is John and he, with his Wife Jennifer, owns and runs Mede Manor on the South Coast. He's a sort of cuckold counsellor and after we had talked, within minutes even of discussing my situation he convinced me to embrace my cuckoldry and learn to love the idea of a better man bedding my Wife."

" ..... learn to love the idea of a better man bedding my Wife."
 

 'Mede Manor?' I thought, 'Isn't that where Maddie, Bruno and him are having some kind of 'marriage ceremony' on Sunday

Alana took a deep breath as she clearly was about to talk more intimately about her 'journey'. "John is clearly an astute man because he had deduced very quickly that I am quite fastidious and he said that such guys often have feminine traits. He advised me to start slowly with stockings and 'hold ups' and to also talk to Maddie about how to actually manage these things. I thought that Maddie and Bruno would laugh at me, but they did not. They encouraged me. She bought me pretty underwear and padded bras from a shop in Bond Street and invited me into their bedroom when they make love."

"So you're part of their lovemaking now?" I asked.

"I was before that but I hated it," she replied without commenting on my interruption, "all that stickiness and intimacy was repulsive to someone as fussy as me. I only did it to keep Maddie happy, although she said that she would never leave me, but I couldn't be sure. To please them both I was advised to buy one of those plastic things for my little willy, just like the one you now have," she ignored my embarrassed look, "and tried as hard as I could to please them. But we all knew that my heart wasn't in it. Unlike you cj."

She ignored my even redder face and continued. "The sudden enlightenment came to me on the first night that I came into their bedroom ...."

"Wait a minute Alana," I said fully aware that I was interrupting her again, "what do you mean 'their bedroom'. I thought it was your house that you live in still. Have you moved?"

"Oh no cj!" she responded quickly, "it is still our house, it's just that now I recognize Bruno as 'My Master' it is only right that I refer to the main bedroom as 'theirs'. Can I continue now?"

I nodded but she carried on anyway. "I had just a garter belt and stockings without my restraint on when I joined them for the first night as a woman in their bed and immediately everything felt so right. I was no longer the finicky little fusspot, but I now had a double sexuality. I was no longer a man, because in all truth I hadn't been a real man for quite some time. I was neither man nor woman. A slut who would do anything with anyone and to anyone. In modern parlance, my type of sexuality has a name."

"..... everything felt so right."


My open mouth gave away my incredulity and there was a silence in the room before I could think to ask the obvious question, "Do you mean 'Transvestite?"

"No cuckold james! I don't mean that," he replied with a wide smile on his face. "I am no longer cuckold Alan, I am now Sissy Alana."


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