Cuckolding in it's very beginnings..

We had talked about cuckolding about a year ago. In fact, we had more than talked about it. We had made the decision to make our fantasy a reality and my boy began looking for suitable 'prospects' for me.
In summary, I didn't find anyone who I felt comfortable enough with to even meet, let alone anything else, and after trying to be undetered, we eventually decided to give in for the time being.

I said, someone suitable would come along at some point, and reminded my boy it had taken me 7 (maybe more) years of searching to find him.

During the summer holidays while my boy and I were separated by our individual holiday/family commitments, I browsed an old online fetish haunt of mine, to catch up with friends and keep my mind busy.

During one such visit, I had a new message from someone I hadn't spoken to before - nothing unusual there.. I get many such messages daily. It said only "Hello". Normally I would immediately discard such a poor effort, but the photograph that accompanied the message made me reply - "nice pic - shame about the message"

And so a communication began. 

I found myself getting to know a 24 year old young man. He was, for many reasons, out of the ordinary. The words I am about to use to describe him are not meant in any way as a put down. Rather, they are what drew  me to him, and those of you who know me will understand why.

"Shy; isolated; nervous...

intelligent; thoughtful; honest...

awkward; socially inept and uncomfortable..

virtually no experience with women..."

Eventually, this man developed confidence in me sufficient to arrange a meeting, firstly explaining to me that he had a stammer - which only made me find him more appealing.

The meeting, in a public place, last month, went well.

Tomorrow we are meeting again. In a more private place - my boy's house.

It has been a very intense time for all three of us.

My intention is to coax my new boy, and build his sexual confidence, widen his experience, and bring him to a place where he will eventually become my lover.

I will then introduce my boy to the equation and his development as a cuckold chastity slave will begin.

Infact, it has already begun - I see it when he sucks in his bottom lip when I talk to him of my new boy, I see it in the way he speaks to me and his intense devotion to me, in the reddening of his cheeks and the lowering of his eyes..

This is the boy who's penis is locked away, safely. This is the boy who is owned by Mistress Keyholder, and this is the boy who is only becoming more devoted to her relentless training of him.

Promotion for boy

You will know from my last post that my boy and I have our ups and downs, like any couple in any long term relationship - there are always little glitches.

The summer holidays prove to be a testing time for us as we have separate holidays and children mean that we spend 6 weeks with very minimal contact. Our communication is mainly by text and this often leads to misunderstandings and fallouts. This year was no different and we had some difficult moments.

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Our first meeting after the 6 weeks summer break was a mere 2 hours together, but we had privacy. My boy had been restrained in his device almost continually for those 6 weeks and I knew he was so looking forward to me going to meet him with the keys to give him some relief. He had been telling me how desperate he was, how he needed the cage off and to have some stimulation. He was so very desperate for some stimulation, and knowing it was coming, his texts showed me that he was very needy and excited for my visit with the keys.

I duly arrived with the keys. My boy's actions and facial expressions told me he was feeling very submissive and eager for his release. As we stood, kissing against the wall, I told him he was going to have a special treat today. 

(Cocklet in my mouth perhaps...lubed rubber hands sliding up and down cocklet's length perhaps...orgasm... ?) I could imagine him thinking these things....and he told me he wanted it to be a surprise. I took no notice of his request to maintain anticipation, and instead told him I would be removing the cage and allowing cocklet to become hard. 

A bit of an anti-climax for him, as he expected as much after so long imprisoned! I imangined he was thinking I was giving him just a taster of what was to come - the cage removed, and then...... fun for cocklet.

We went to the table which he had got out ready for me at my request. Rope and hitting implements were also laid out at my request.

After removing his device as promised, I instructed him to lay face down on the table, cocklet poking through the hole. I tied his hands behind his back, and then began to tell him of my new plans.

"I have decided I am going to start touching cocklet less from now on. Denying him orgasms doesn't seem to be having the desired affect any more" 

"Oh it IS Mistress, it really is."

"I have noticed a change in you since the cage has been on for longer over the holidays." (He had, towards the end of the holiday, been making noticeable efforts to please me and be good, knowing that our meeting was approaching and that his speculated stimulation was near, making sure he had earned his reward.)
"I like him so much more since I haven't been touching him."

"Oh no Mistress, not after all this time, please, he needs touching, please, no Mistress."

"Don't worry. It's ok. Shh... (his whimpering subdued only slightly), It's a promotion! It means you can be a better boy for me. It will give you much nicer feelings of frustration and submission. It will be lovely. It's a special thing. .. and ... do you know what...? You will actually thank me for doing this to you."

Cocklet throbbed and dripped through his hole in the table. He flicked and danced about  in sheer desperation for something, anything. Anything at all. 

It was a pure delight to watch and made me feel very loving towards my cocklet.

My boy, with his hands tied behind his back, cocklet out of reach but so incredibly desperate and sensitive and needy. Unable to reach beneath the table, only able to push against air. Into nothing. 

"I realise darling, that you need something. Some physical contact. But my hand will not be touching cocklet today. In fact, we will be reducing any touching at all that cocklet gets. But I will let him know that he has been out today. I will let him have some physical relief."

And so I proceeded with the implements left out for me. The slapper, the crop, the metal, beady cat-o'-ninetails. And I began first hurting his body. Then, I turned him over so cocklet was layed against his belly for me. And I let cocklet know he was out. I hurt him. Balls, cocklet - his length, head, topside, underside, left and right. I hurt him till I felt he was fully awakened, til every part of him had had some contact with my control.

Then I sat my boy up.

Cocklet rock hard, erect, desperate.

I layed on my front, my mouth close to cocklet, and I brought my boys hand round in front of him, almost close enough for him to touch.

And there, I layed, closed my eyes, and opened my mouth... (at last, a treat for cocklet?...) And I slid my wet lips down, down over his finger, which I held right up close next to cocklet. My boy watched intently, barely able to stifle the need for my lips on cocklet, but imagining.....if only. I tormented him in this way for quite some time...making him watch this torture.

Finally, untouched cocklet's time was up, and he went back into protection. 

Wasn't that a lovely treat my love? Just being hard now is going to be what you yearn for. Cocklet in my mouth, sexual relief, pushing into me, my hand wrapped around him... those things are gone now. Cocklet has been promoted to a new level of denial. 

He will now yearn only to be hard... if only he could be erect.

.....


"Thank-You, Mistress"

Difficult Times Lead To A New Focus.

Despite initial appearances of our relationship being perfect, we, like any other couple have our ups and downs. 

Just recently we have had a very serious down. It lead me to a point where I felt I could no longer continue with my boy, and for a short while I left him, with his keys returned.

However, despite our difficulties, I knew I needed him enough to try and mend what had been broken, and after experiencing anger and then grief, I then came to a place where I felt it was possible to rebuild. We have both worked very hard at that.

The problem involved a rule I had made that had been broken, a number of times and of course, covered up to hide it from me. The detail isn't relevant, but what was significant was that I realised my rules were not sacred. They could be broken without my knowing, many times over. 

Rules, were no longer the way to dominate and control my boy.

Initially I felt there was no hope for the future because I based my control on rule and trust. With that gone I had nothing left.

But then, gradually, a new way of controlling him came into my head, from out of nowhere. 

It was clear, that with trust there is always chance for infallibility. He came to me for my control, and I was failing to give it. He proved a rule could be broken easier than snapping a twig. It was not control. And if I provided twigs to be snapped... 

(The truth is, he like anyone suffers from human nature. It is why we have a harsh metal cage encasing his cocklet, because he needs it there. He cannot be trusted with his freedom.)

So I have had a bonfire and there will be no more twigs. I will instead make requests. They will be there for him to respect or not, out of his own choice. He will know my preference, and that is as far as I can go with that.

I started fantasising about financially controlling him. Making him pay me for things. He could not escape that, and I would make it so the things he was paying for, he was begging to pay me. Once the money has left him, he can't reclaim it. That control suddenly became very much more real than a rule. I could really make him suffer, make him poor, cripple him financially. But all by his own doing.. because he would have begged to have paid me. He would be responsible for his own demise.

In the process of him breaking twigs, I feel that I have lost my standing in many respects with him. That is how I feel. I feel I need to rebuild the pedestal on which I once stood. So I am going to limit the physical contact he is allowed with me. His lips may not touch any part of my body other than my hand of my foot without him asking consent. There will of course be a fee involved in his asking for permission.

Instead of kissing me, he will crave to kiss me, to earn the opportunity to pay for a kiss. 

I tell you all this, because life isn't perfect and I don't want to pretend it is for us. We have both suffered these past weeks. 

But we both believe we have something worth working at, and so this new chapter of control begins.

First Days Play with a New Toy.

It had been 6 months and 5 days. Denied and constantly caged, except for when I let him out, supervised. 

I had a new toy to introduce him to. I had bought it and saved it for a special occasion. Today was the special day. He knew nothing of it, except that he was going to be experiencing something new.

Although it fitted my mouth perfectly when I tested it for size, it was a struggle for him to get it in. We eventually had to compromise with it tilted slightly backwards to accommodate his small jaw stretch. I fastened it tightly behind his head and then proceeded to wrap his head with black cling wrap that I had salvaged from a recent parcel. I kept his mouth free, but it was very easy to apply a smaller piece of the black plastic just over his mouth, to assert control.

I loved how his mouth was held open, ready. An orifice for my amusement. I could put in there whatever I wished to. And, as I did so, I reminded him how it was his duty to serve me. To be obedient. He does forget sometimes, his place. He does, in the every day world forget, and asserts his opinion, his right, his feelings. I very rarely, if ever, say anything at the time. But I save the evidence, and recount the correct manner for a slave when he is appropriately beneath me, mentally.

Today, he was very beneath me. I made him so, and I loved making him so. The things that I dropped into the circular ring which force held his mouth open were bad. They lowered him, and made him something less. They made him my slave. My obedient worshipper, willing to take whatever I dropped into the disposal unit his mouth hole had become.

And then, when he thought I had made my final insult, I asked if he wanted the most disgusting thing ever. At first he couldn't think what could be more disgusting. But he was thinking with his head and not mine. For me, there was the most vile and disgusting thing imaginable yet to come. But it required him to produce it.

And so I placed a plastic bag over his desperate, dancing and straining cocklet. I instructed him to rub against the bed, and as he was ready to produce the most disgusting thing ever, he was to take the last morsel from my hand and devour it. For this, the ring was removed from his mouth.

He told me later that the contents of the bag has been relief to his mouth, after the horrendous things I had placed in there. 

I felt no regret, unease, guilt or lessening of my will for him to consume my offering, despite the way he struggled with it in his mouth. Despite the way he gagged on it. All that did was make me feel proud that my boy was doing this for me. He was taking all that I was giving. It was a very deep act of submission.

It became a very loving act. It became something that brought a closeness. And he, now, when I look at him, is lower. Lower than ever. But I treasure him far more as my slave for committing himself to my will. 

For accepting humiliation for my pleasure.

Table Video - Tease and Denial.

My boy had been denied orgasm for almost 4 months when we did this table play.
At the end of it, he was locked back up, still without orgasm.

Plans..

There are a few fantasies around chastity that are very dear to me - I have had them for over 2 decades, from my late teens and from my very first thoughts around domination and cock ownership.

One of these long standing fantasies involves a table. It is padded and long enough for slave to lay on, face down, with a hole in the middle for him to expose his cock through. I visualise myself under the table, with the part of him that concerns me, neatly presented, isolated from the rest of him and at my disposal. It perhaps seems at odds with a dominating role, to be sat, crunched up, under a table. But this for me is exactly right. I am in my own private space, unhindered, separate from slave even, just with his protrusion, there for my sole pleasure. I don't feel rushed, under pressure or obligation, watched or even in the company of another. I feel isolated almost, in my own world, and with complete freedom to do exactly as I please.

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When my boy first moved to his new house, on my street, we talked about new equipment we would buy or make, situations we would devise, and more. But even after a year, we have had so much else going on that we haven't really had time or need to explore these ideas as yet.

I had planned on instructing my boy to make the table of my fantasy, but I suddenly had an idea just last week. We have a massage table. Slave bought it for me for my birthday last year, and we have made good use of it as a massage table. It has a hole where you can rest your face.

The hole is not perfectly placed for a slave table, so I gave my boy the task of experimenting with the bed, settee and table to devise a stable position for him to lay face down on it, where the hole is centrally placed for his exposure.

He did such explorations with the table and came up with this.

He tested it, and it worked perfectly.

With the cage removed, this was exactly how I had imagined it in my fantasies. This is what I have been waiting for.

My boy, knowing the time I have invested in contemplation of this scenario, has had his own expectations heightened because of this. He has been imagining all kinds of things, feeding my already full repertoire of situations. 

However, in truth, he may find that on our first session with THE TABLE, I purely just explore, very slowly, the feeling of having him at my mercy. I do not tend to rush things, but prefer to go slowly, savouring and relishing every moment.

His first appointment with The Table is in 3 days time.

I have an equipment list which I will send to him to prepare and have layed out ready for me, and if the mood takes me, I will share the details with you all - 

my hungry followers of chastity heaven.

New photos of Mistress KeyHolder

My boy had a lovely idea and he has been working and compiling for me.

This is the product of his labours... 

all for me..

http://mistresskeyholder.blogspot.co.uk/p/mistress-keyholder-photos.html