pipsqueak becomes a cuckold

It has been sometime since I last provided an update on the continuing evolution of a Domme fairly new to domination, the wonderful Samantha. But Samantha has continued to evolve at a face pace! As pipsqueak has learned to his cost – or is it his cost? The paradox and symbiosis readers of this blog are familiar with are both strong.
The paradox; pipsqueak is a true submissive and so he craves to be helplessly dominated by a cruel, pitiless woman who puts him through things he truly does not like. But from this he gains true contentment that he cannot happily live without. (Like all true submissives including my bitch-boy.)
The symbiosis; Samantha is now a cruel, pitiless woman who puts the helpless pipsqueak through things he truly does not like; and she gets huge pleasure from doing so. So the relationship a perfect symbiosis.
I have in bold highlighted some text in the account below that I found particularity hot! Enjoy.
Dear Scarlet,

It’s been a long time since we last communicated and I thought I would give you an update.  The past 4 ½ months have been rather busy and extremely enjoyable. pipsqueak is very content despite my further progress in making his submission and life harder than ever most of the time. In our case we have found that an occasional relaxation of the regime works best for us (more in a moment).

Perhaps the most important change has been that pipsqueak is now a cuckold. I worked hard on my exercise, diet and appearance between March and May and finally felt confident enough to take the plunge. It would be nice to say that I have found the perfect lover but that would be an exaggeration. However, I have been on quite a few dates and have had sex with two men so far (including ‘masked sex’ on one occasion which was hilarious if not conventionally orgasmic).

The first time I cuckolded pipsqueak was at the end of June. I’d been chatting with a man online for a while. He lives an hour away so not ideal but I agreed to drive to his house (he’s separated). Sex wasn’t guaranteed but it was on the agenda. In the end we both wore masks, obviously didn’t kiss and had very mechanical and hilarious (safe) sex. The most important thing for me was that it was done. I was a cuckoldress.

 Pipsqueak had no idea. I was away from mid-morning to 4 p.m. I didn’t explain my absence and he of course didn’t ask. (He would not dare!) I’ve been increasingly going out during the day since lock-down regulations eased. Later he told me he hadn’t a clue which was delicious. I made him perform orally for me on the same night and my orgasm was special. For 72 hours I basked in the afterglow of what I knew and he didn’t.

 Four days afterwards, I told him matter-of-factly that Lockdown’s easing allowed me to cuckold him and I intended to do so soon. He uttered his usual noises about it being ‘my right’, etc. Then I laughed and told him I already had. His expression was a picture. He didn’t know whether I was mind fucking him or not. I said that’s where I’d been for 5 hours the other day and showed him my photograph of me half-dressed in a man’s bedroom. The penny dropped.

 I made him lick my pussy again, there and then, while I continued talking. I said I would never have told him if I hadn’t enjoyed it. It would have remained a one-off he never knew about. But I’d enjoyed myself immensely and it will no doubt be much easier and better in future. I told him to kiss my bottom instead, as his contact with my pussy will be even more restricted in future.

 In that moment, I think he was partly turned on and partly too shocked to compute. But over the next day or so, he went through some denial, a touch of resentment that I’d actually done it, but mostly acceptance. We’d been talking about it for so long that I think he’d discounted the actual event itself, so to speak. I adopted a caring attitude of reassurance combined with my blunt stance and some mischievous teasing. He hadn’t had an orgasm for over a month and he told me later he expected me to ‘seal the deal’ of his compliance by at least letting him masturbate or fuck his rubber sex doll to orgasm.

 Whereas I did allow him to edge a lot but not to cum. I said he must never see things as some kind of trade off or bargain between us. I will never ‘pay for’ my own fun by allowing him some of his own. His orgasms have to be earned by what he does, not what I do.

The second time I cuckolded pipsqeak was very different. I didn’t slink off unannounced. I did it blatantly. I’ve been on a few socially distanced, outdoor dates when the weather permits. Sometimes I even go for a drive and walk on my own just to get out and leave pipsqueak toiling. I have got to know a local-ish man who’s not ideal for a couple of reasons I won’t go into. But he is interested in no-strings sex, as am I.

 Pipsqueak was sweetly brave as I left the house, wishing me a good time. I told him to shut up and get on with his list of chores. I said that sex wasn’t guaranteed and he mustn’t think as if I do this to any kind of set routine. It may or may not happen. I’m simply an independent and mature woman who can make up my own mind at the time whether to have sex or not.

 When I returned it was, of course, very different too. I was glowing. The sex wasn’t perfect but it was conventionally better. I summoned pipsqueak to follow me up to my bedroom. I undressed and let him see my rather red and swollen labia. We had used a condom (two, actually) so there was no evidence for him to clean except my engorged clitoris wanted more attention.

 I lay back on the bed, my legs splayed wantonly over the side, and stared up at the bedroom ceiling, while pipsqueak licked me in his apron and spike lined chastity tube. Neither of us needed reminding it was now over seven weeks since he’d had any kind of orgasm. After I’d climaxed, I let him unlock his cage. I love the tiny red dots the spikes leave when he’s aroused. I said he could put his erection inside me for five super-slow strokes.

 He groaned with desperation as he eased it inside me bit by bit, in and out. While he did so, I talked to him. I asked if my pussy felt different? He gasped no. I told him that his cock did feel different. It felt smaller, thinner, second-rate. He whimpered. I instructed him to pull out after only four strokes as I was disappointed.

 I sat up propped on my elbows and said he could wank himself while I watched. I continued to chatter, while he frantically fisted his shaft. I asked him, one final time, if he regretted our new relationship and my freedom to date other men. His eyes were gazing into mine. No, he gasped. I said I want to see real enthusiasm for my sexual progression and his further demotion over the months to come. He nodded, unable to speak.

 I snapped for him to stop! He somehow tore his hand away and his glistening erection bobbed between us. His expression was a picture; of awe and adoration, deference and desperation.

 And then I smiled. I love acting the bitch but I’ll always struggle to be heartless. I reached out and started rubbing his cock. I’m very out of practise. He has this adorable look of alarm on his face that I’ll stop at any time or at least ruin his orgasm. I did it for a bit and then told him he could finish himself. I said he should aim his cum at my waist and that he could enjoy a full orgasm for once and to make the most of it.

 It only took him about 30 seconds and he spurted an impressive amount of semen on my tummy, thighs and mound. His knees were buckling and he was almost crying with relief. I blew him kisses. In our relationship there are moments for ridicule and moments for bonding. This was one of the latter.

 That’s not to say that he didn’t then have to suck up every drop of his mess. And five minutes later we were back into our roles. Over the next few hours and days I was extremely demanding and mocking. I called him ‘cuck’ quite a lot, even though I have no plans to  adopt that name (I find it too much of a cliché).

 I make no bones about my intention to find a proper boyfriend with whom I can conduct a proper affair; discreet but much more than just one-off or casual sex. Pipsqueak is daunted and excited at the same time. That would be the culmination of the journey we’ve been on for approaching two years; one slow and quite mild year, then this second, very unusual and fast developing eight months.

My goal remains to find a man with whom I can have a proper sexual and, to an extent, romantic relationship who can be integrated into my lifestyle with pipsqueak. I’m impatient but not in a rush, if that makes sense? Pipsqueak has taken well to his new status. I think both of us were concerned – deep down – that the reality could affect our marriage in a way that fantasy obviously didn’t. But by the time it happened I think he’d become so used to the idea of me cuckolding him he was mentally prepared.

 Since Easter I have been even stricter about his orgasm denial. He has a total love-hate relationship with it. He loves me imposing it. He enjoys the intensity of frustration and how ‘alive’ (his word) he feels. His fetish is the contrast between us. But he hates the actual reality of being denied any kind of release for weeks on end.

 His Steelwerks cage has proven the most wonderful training tool. Mostly because it’s wearable 24/7 and hygienic and comfortable so long as he’s soft (less so when he’s aroused and occasionally at night). I make him tighten the spikes each morning and loosen them overnight. However, I like the spikes fully extended when he’s performing orally. Making him control his erection while he’s focused on me is absolutely one of my favourite things!

 I recall that I was still inclined to indulge him when we last communicated. After a few weeks I’d still feel sorry for him. I even used to enjoy his groaning, pent-up orgasms when we started. But that’s no longer the case. He can still have orgasms but they have to be earned. And when I say earned I mean it! The price now is increasingly outrageous and still going up.

 Away from the sexual side of things, I have very much focused on his monotony and drudgery. He will not be returning to the Care Home job any time soon. But I plan for him to work backstage in a busy pub doing washing up, that kind of thing (NOT behind the counter serving pints). When pubs open properly and safely again, I want him to work weekend nights in particular – say Thursday through Saturday – when I can be out on dates, that kind of thing.

 At home, I control every minute of his day for three weeks out of four. A combination of housework, garden work, monotony and sensory denial from dawn to late. The weather has mostly allowed him to work naked in the garden since Easter. Or in a diaper. I am brutally strict about bladder and bowel control. If he needs to go while he’s tending the lawn with nail scissors, he must hold it in, or fill the diaper and face the consequences.

 We also practise TSD (total sensory deprivation), in the garden. We have a double sun-lounger made of that wicker you can leave outdoors. I let him unlock and remove his Steelwerks and then tie him naked and spread-eagled on the lounger. When he is secure, I blindfold and funnel-gag him and put the Bose headphones over his ears. If it’s sunny I put some sun cream on his body and limbs but not his cock and balls.

 His lounger is near mine, so I can relax while keeping a close eye on him. I love to study his face when he’s completely unaware I’m watching him listening to porn. I don’t allow his genitals to burn but I like them to get a bit red. If he gets aroused – I coat his erection in Deep Heat blended with sun cream. I love to urinate into his funnel or, borrowing your idea Scarlet, melting piss ‘pyramids’ of ice in it.

 We now possess a full size rubber sex doll. It’s particularly fun outdoors to allow pipsqueak to ‘make love’ to her on a humid, sunny day while I watch. There’s no need to worry about the mess. I coat her in baby oil so she’s super slippery combined with pipsqueak’s sweat. They fuck on the grass. But his cock is coated in Lidocaine (numbing cream) and he’s forbidden to orgasm without permission (almost never granted). It’s for the doll’s and my pleasure, not his.

One week in four, nothing fundamentally changes but I relax my regime. He needs this space and TBH in a way I do too. He’s still chaste, obedient, that kind of thing. But he’s much more my husband than my slave-sub. We chat more, discuss, even argue about news items, watch TV & Netflix, etc. He does the housework but not (well, rarely) any mindless tasks or TSD. It’s really just switching down into a lower gear for a week. But we never actually ‘stop’ as we’d find it too weird now not to be Mistress and slave. I just become more benevolent for a while.

 I could go on but hopefully this update is of interest.


11 thoughts on “pipsqueak becomes a cuckold

  1. Delightful, and a joy to see another positive convert to a FLR. Mistress Scarlet must feel great satisfaction from building a group of superior females who blog here or have their slaves do likewise.
    Mistress Serena (my Mistress/Wife) embraces such posts and as always gleams and gains insights and ideas She can manipulate.
    Like bitch boy, pipsqueak, slave m and many others, i desire, need and crave domination and submission ( i have been a true submissive since early childhood ) and adore all such minded females, the more cruel and pitiless the better
    Congratulations (Ms) Samantha

  2. Ms Scarlet, you mention the paradox of submissiveness in several posts.

    As a submissive man I crave very much to be owned and helplessly dominated by a sadistic woman. But why is it so? What is that mysterious logic behind that paradox?

    Here are few thoughts of myself about this topic:

    Love is a very basic force which defines who we really are and strongly affects our sexuality. We all need to love and be loved. And I believe the need to be dominated originates from this very basic force too. In particular it originates mainly from the way when we feel we are loved.

    In comparison with vanilla mind the submissive perception when being loved is a bit shifted. The submissive man feels he is loved when she not only expresses a desire for him but she expresses her desire for him is so strong she wants to own him. And owning something means you have control and power over it.

    And that is why we crave to be helplessly under control and dominated – desire to be under control is driven by the need to be loved and being dominated is a proof of being loved. I do not mean the act of domination itself proves the love. It is the sensing of great pleasure she gets from dominating me which is so overwhelmingly satisfying – it proves her genuine feelings towards me which makes me feel loved and wanted.

    The desire to be put through things I really do not like is then related to the second force of love – ‘need to love’.
    Therefore enduring things for her pleasure she gets from dominating me by putting me through things I really do not like gives me the feeling of being wanted and loved and at the same time allows me to express my love.

    1. As you may imagine, I have pondered and studied this matter extensively for many years; so I always appreciate when other so so too. I am afraid I find several flaws in your love theory.
      You stated love strongly affects our sexuality without explaining why you believe that. I can think of no evidence to believe that when considering gay, lesbian and bisexual people.
      The main problem with your theory is that there are a great many submissives who are deeply in love with and addicted to a dominant, be that wife, girlfriend, or dominatrix who does not reciprocate that love. She does not love the submissive.
      Dominant women rarely desire a submissive so much they want to own him. They want to own him because that represents and indicates the power they have over him. It is about power, not desire.

      1. I very much share your views on this. I fell in love with the man who became my husband. It was only (much) later I accepted him as a submissive and maintained my love for him. I very much doubt it could have happened the other way round. I would very likely not have fallen in love with a submissive man when I was younger and it would have then been very difficult to accept him as a vanilla husband. It is indeed about power. I have learned to embrace and enjoy the power I have over the man I love, if that makes sense.

          1. Dear Scarlet,
            From point of view, the primary desire in a dominant woman is that of control, power and freedom.
            Control over the partner, so that she can influence his life and make sure he is always compatible with her needs; power to express her every wish on him with the knowledge that he has no power to oppose; freedom to live her life even without him.
            I was lucky enough to find a partner suitable for this lifestyle and, of course, I’m happy and I care about his well-being, but I don’t think it can be said that I love him! It is more something that resembles possession. Sissy slave M. is my property, and obviously it is a property that I care a lot about and to which I am also emotionally tied, but I am still tied to it as you are tied to a property, and not to a person and, even less, to a husband.
            It can probably be different when the woman discovers the femdom and its dominant side after having already experienced a ‘vanilla’ relationship with her partner.
            In this case, probably, the love relationship can turn into a relationship of domination while maintaining that sentimental connection which, however, is missing in relationships in which the femdom element exists from the beginning.
            In any case, I believe that love can eventually remain alongside the sense of power and possession, but that it is not the starting point of domination.
            On the other hand, even for the submissive, I believe, it is not love that leads to submission but submission leads to love.
            That is, I do not believe that the submissive man submits because he loves but I believe, on the contrary, that the submissive man falls deeply in love with the one who dominates him or the one who he believes or hopes can dominate him.
            Also in this case, therefore, it is the desire to be submissive that leads to love, and not the other way around.
            Indeed, in my opinion, in some cases, love can even become an obstacle.
            I met several women who, although interested and fascinated by this world, and with boyfriends / husbands more than willing to submit, were blocked in their path by love for their men.
            In them the concept of love was anchored to care and affection and they were unable to overcome this block and to understand that for their men being dominated also meant being loved.
            I therefore believe that those who dominate as a modus vivendi, not as an occasional erotic game, are moved by a desire for power, control and freedom, which can coexist with love but can also be limited by love itself.
            On the contrary, I believe that the submissive easily falls deeply in love with the one who can satisfy his deep submissive nature.
            Thank you

  3. What an introduction to cuckolding. As special for her as it should be. And to get her husband to perform oral sex afterwards with her basking in the glow of what he didn’t know ….. just about as perfect.

  4. Dear Mistress Scarlet, i cannot get the comments on love and husband slaves out of my mind. since i am closeted, i feel unworthy to comment but hope that what i have to say will be of interest. The amazing Dominant Women Who write here All seem to love owning submissives, and value what They own. But as Lady Francesca says above, They don’t necessarily love their property. i believe Lady Jessica, Whose contributions i so miss, also values but i suspect does not love skivvy in the sense discussed here. Love in this discussion seems to be romantic love for a partner. Perhaps Dommes who knew They were dominant and sought submissives to own have no need for romantic love, but the Ladies who became Dommes may still love Their property, as Mistress Samantha so eloquently states above. i assume such love may or may not still be part of such a relationship, as the Domme wishes. The submissive in most cases will of course love, worship, and adore its Owner deeply however they came to be slaves. worshipfully, chrissie

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