Love, sex & chastity: Why cuckolding is perfect for you and your partner(s)

I know, a wild guess here but if you have a wife, a long-term partner, or somebody you’d wish to see in that role – and if you are here, reading the Sissylover Academy‘s blog… Well, from time to time you probably fantasize about being a sissy cuckold;) Fantasies are, of course, good and all, but actually locking your clitty up, talking through all of it with your partner, figuring out the whys and hows, and most importantly coming to terms with it yourself – that’s a bit more knotty, isn’t it?

Well, you’re in luck, sugar, cause right now we will untie all of it, gently and thoughtfully, to help you gather your courage (or rather submissiveness) and open this door (or rather to lock yourself in). Buckle up, hun, today we take a deep dive into all the marvellous things that await you in the realms of being a chastised sissy for your loved one.

You won’t have to always be the strong manly husband/boyfriend/partner

..if you let your significant other have other sexual partners. Sounds counterintuitive? Well, bear with me. At some point, every sissy has felt the pressure to be more masculine, to hide their femininity. Keeping up appearances, acting, “manning up” – isn’t it exhausting? Isn’t it soul-draining? For many sissy girls, it certainly was. For you it probably is.

Many sissies come to the Academy because they find comfort in no longer being forced to conform to aggressive, masculine stereotypes. And for many sissy girls, one of the biggest sources of that pressure to be ‘manly’ is their partner. It’s very common for a sissy to feel ashamed of the fact that they can’t sexually satisfy their significant other, because their clit is too small, or because they’re not the Alpha Male stereotype that women supposedly find so arousing. It’s among the biggest reasons why sissies hide their feminine side – fear of rejection from their partner if they ever came clean.

Cuckolding can remove that fear. If somebody else is taking care of your spouse’s sexual needs, then you don’t have to worry whether or not you’re able to measure up. For years, the choices you have been facing were either to sexually satisfy your partner, perhaps even by hiding your sissy side; or to be in a loveless relationship, where being cheated on, breakup and rejection are always hanging there, menacingly, at the back of your head, spawning fear and uncertainty. Cuckolding provides a third option: to give your wife a way to be sexually satisfied, and for you to be yourself.

Happy Wife, Happy Life

For decades, women have been forced to choose between partners who can keep them sexually satisfied and partners who are dependable, emotionally sensitive, and worthy of a long-term commitment. Sexually bored women have had to hide their longing from their husbands, going in secret to meet with men, even with the risk of getting caught.

Nowadays nothing has to be hidden, and nothing has to be secret. The number of couples who are openly agreeing upon consensual non-monogamy and seeing other people is growing day by day. The shame and the stigma that once surrounded polyamory are shrinking, and acceptance of such a sexual lifestyle is growing. Your wife will be happier if she’s not shackled to you, and if she’s free to pursue sexual relations with other men. And no darling, not necessarily because of you not being good enough.

Sexual adventures, the thrill of new experiences, and new paths in this polygamy world all add up to her being reminded how beautiful and sexy she is, that she is wanted, admired and respected – not only by you, who she already knows thinks the world of her, but also by other men (and maybe women). And it’s so important for a woman to not let these feelings of self-worth fade with time. And your partner will be so grateful to you for letting her ignite them once again.

Do you know who else is free to pursue sex with other men? You! And you, my sweet sissy, will be so much happier as well – if you remove trying and failing to sexually satisfy your partner from the equation… and if from time to time you focus on satisfying those who you actually can satisfy. After all, your tongue and boypussy have much more potential than your clitty.

Channel your sexual energy

So, whilst somebody else is making use of your wife, what happens to you? I think the answer is obvious, isn’t it, sweetie?

Now that your wife is understanding and accepting of your needs, she should have no problem becoming your key-holder, and she’ll soon see the benefits of keeping you in chastity. We could spend a long time here going through all of the positives, but that would be a topic of its own. Let’s focus on the one you might not have thought about before.

Spirituality has always had a strong connection with chastity. People have known for a very long time that focusing your energy on sexual pleasures can get in the way of more important things… and so, a major part of many spiritual paths in many different cultures is being able to re-direct your sexual energy to more useful activities.

A person in chastity begins to build up sexual energy (sometimes referred to as ‘sexual frustration’). As time goes on and you are unable to satisfy your lust, that lust will continue to grow. What happens next is up to you: You might end up begging for your key-holder to release you. Your sexual arousal might relocate itself in your body – it’s common for girls in chastity to experience more sensitivity in their mouth and their rear fuckhole… which is exactly what a sissy like you might be looking for.

Days, weeks, months in chastity will go by and you will need to find useful ways of redirecting the energy that’s been built up. Think about the things you’re passionate about, that you want to spend time on. Think of all the things that may benefit from your extra energy. Your career, hobbies, self-development, living space. Making your partner’s life easier and more pleasurable by helping her out, doing things for her. Housework, beauty, self-care. And, no less important, your sissy training. These are all worth channelling your energy towards, and certainly worth saving up your energy for – especially, if it can be done as simply as by staying in chastity.

Are you a real man?

Let’s address the elephant in the room – the question of whether or not you count as a real man, whatever that is. If you’re sure the answer to that question is yes, then I don’t know what you’re doing here, reading a blog post on! But let’s say you’re not 100% sure.

The truth is, it doesn’t matter if you’re a real man or not. If you’re still reading this article, there’s no denying that you find the idea comforting in a way. For example, it’s comforting to think that the reason your marriage or relationship is lacking the sexual flame lies in you not being able to satisfy your partner. It’s certainly easier to accept than to face that maybe you just don’t try hard enough. And that maybe you simply don’t want to. These thoughts can spawn so easily, and once they do you can’t just erase them. They can be far away from the truth but still, they stay and they circle around, begging for answers which you don’t possess… Yet.

That’s what cuckolding provides, more than anything – it’s the easy answer you’ve been waiting for. If you embrace your role as a sissy cuckold, then it doesn’t matter why you can’t satisfy your wife. You just can’t. Not in a conventional way at least. Well, how can you, when your clitty is locked up, right? It’s something you can’t fight. It’s another decision made for you. It’s a true acceptance of your submission, and it comes with all the benefits that being a submissive brings you.

To sum up: You could never get your partner to call you “daddy” in bed. But now, she can call you a “good girl” instead. Doesn’t that have a better ring to it?

Dealing with jealousy

A lot of you are probably thinking, “But how would I deal with the feelings of jealousy”? The obvious answer, of course, is that when you’re a sissy cuckold, jealousy is expected from you. A lot of people choose cuckolding because the humiliation and the envy turn them on. But that doesn’t have to be the case.

Jealousy and possessiveness almost always come from a place of fear. Fear that you’re going to lose your partner, fear that you’re going to be left alone, fear that you’re unlikeable, fear that you’re boring… and especially fear that your partner is keeping secrets from you. It’s perfectly normal to feel insecure about yourself when you’re comparing yourself to another man, another lover. So what can you do about it?

Now, if I was being cruel, I could remind you here that as a cuckold, you should just accept that you don’t compare. You’re not as attractive, not as good in bed, and you should just stay in your little chastity cage because in the long run that will make you happier. It’s not even a competition, so why stress about it? 

The more honest answer would be that those insecurities are things to talk to your partner about because chances are that cuckolding isn’t what caused them in the first place – it just highlighted your deep-rooted feelings. And if you’re willing to go down the road of playing in this way, making you more jealous, toying with your emotions, then it’s a good idea to make sure you’re in a strong enough starting place. 

45 thoughts on “Love, sex & chastity: Why cuckolding is perfect for you and your partner(s)

  1. Kierstyn says:

    Never considered cuckolding as something I’d be interested in trying, sure swapping or watching her fuck another guy was hot while I was fucking his wife, but after reading this and my recent shift into feminism, the idea of watch a man fuck a woman to later “clean” her up. Or to suck his cock or tongue his ass mmm exciting me as I think about it. Maybe he’ll want to cum on my face or down my throat. Or maybe he’ll want to be the first to fuck my pussy. While I service her pussy with my tongue more than my coc er clitty could. The fantasy is hot maybe I’ll rethink this

    • Katrina says:

      I am single but much of this still rings true. I have just entered the service of a Mistress and the first thing she did was have me collared and naked in front of her. She proceeded to describe what she and all other women needed in terms of a proper alpha male. Size does matter and I simply didn’t measure up. She measured me with a tape measure and took intimate photos to prove the point. She was very firm but kind as well as she coerced me into accepting that I would now accept that I have a “sissy clit” and should never again attempt to satisfy a woman with it ever again. She would help to train me in other ways (if exceptionally obedient) to please her and her friends. I feel so happy now that I will have a new role. Xx

      • Alinna says:

        That is exactly what I want, and need, is to feel like a good girl and feel how powerful it is knowing that I can get a man rock hard and make him cum, simply by being a submissive, feminine cock whore. Everybody wins!!!

  2. Lil'Ashley says:

    Sadly I’m a single sissy who was always too aware that I’d never perform or fulfill her needs.
    But seeing those gifs, the idea of being useful to real men has me so turned on. It would turn me into a happy cucky if I could make everyone pleased putting ‘that’ in a cage.💜

  3. Svetlana says:

    This was a good read, some years ago I would of just passed over the article and moved on being ignorant of why would someone do this, but now I have started my journey into feminisation and sissification, I can see why this has evolved or surfaced in me, I never married and have had few partners for very short times, I have done nothing bad or wrong, I just have all the characters of a cuckhold, I unknowingly had given up on myself thinking am never going to be good enough for the ladies I wanted to be with… they did not waste any time looking for someone else while I pondered over my silly reasons, the opertunities were there but I made excuses based on all my fears written here. This was my fault for putting to much pressure on myself and trying to live up to unrealistic financial expectations to be a worthy provider or something similar, over time had just indoctronated myself into not being worthy of the woman that interested me. Feminisation and sissification became an avenue for me to explore… what it was I desired but couldent have unless I experienced it personally, having made myself submissive over time, all I needed was a little influence and courage to begin my journey, I got that from online seeing others take extraordinary steps with their life, having found the courage to be a worthy partner in other ways… I was inspired and went down the rabbit hole knowing am going to enjoy this more than what I had experienced before. The article was well written and helps me understand why cuckolding might be perfect for me.

  4. Michelle(a happy sissy cuckold!)) says:

    Love this article! My wife has a few lovers and she accepts my femininity (though is not attracted to it) , but loves me anyway. I’m very happy I don’t have to satisfy her in the bedroom, can be my girlish self, wear my clothes in the house freely, and use my toys(especially my bbc dildo) when she spends the night at one of her lovers house. Also I get to have relationships(sexual and otherwise) with avatars on the social platform I am on (second life). I’m still thinking of seeking out a man, but haven’t done it yet.

    • Cuckold Sissy 207 says:

      Your response echos my own marital evolution. My wife began to enjoy other lovers during our engagement period 10 years ago. She loved me emotionally but was never sexually satisfied by me when we were dating. As she discovered by true bisexually submissive personality, she encouraged me to express my inner femininity. In turn, she decided to take on more masculine lovers who were much better hung than me. It has been a win-win for both of us.

    • Jayne says:

      So true. I’m 70 years of age and have no interest in conventional sex with a female. To a degree, I believe I have been a sissy from a very early age, but have kept my very personal thoughts to myself. I now live on my own and there can no longer be any excuses. I want to become a true sissy for all time, dressing, looking, talking, acting with the mindset of a very submissive slut, owned trained and totally controlled by my new owner.

  5. Michelle says:

    My girlfriend at the time and I have gone through the locked up cuckold journey many times. We both loved it. I got to enjoy her happiness with being with other lovers and I loved my duties of supporting her and cleaning EVERYTHING up afterwards!! I was mainly locked up in panties while they did what they had to. I never got any relief during these times.

  6. Madaly says:

    I haven’t had any girlfriend/partner my whole life. I know I am still young, but that made me think about the reason(s) of this lack of relation. Sissification is what highlighted the reasons I was looking for and now it can’t be more clear that my overall behavior is at fault. I am too passive and tend to try pleasing others. After discovering sissifcation and cuckolding it became clear to me that my place in a relationship is to do whatever it takes to please my partner.

    Thank you for this article ! It was really instructive and eye-opening!

  7. Sissy Mark...Kathleen when in a femmy mood says:

    My wife has no interest in this….and I have no interest in having sex with her. I’m trying to figure out how to have someone seduce her into sex, and then break me into being their cuck sissy. I just don’t know how to start…

  8. Joanne says:

    I really enjoyed reading this article. I have had fantasies about being cuckolded for a long time. In fact, a few years ago, I brought the subject up with my long term partner. We discussed it for quite a while but she was unsure and thought I would be too jealous to really let her be with other men. She didn’t seem to want to do it. I suggested she ‘dip her toe in the water’ by flirting online but she never went for it. Or not to my knowledge anyway!
    This article makes sense of the cuckolding lifestyle. I enjoyed reading it with a bit of trepidation in the knowledge that I am the sissy that needs locked and cuckolded. Deep down I know she needs a Real man to satisfy her.

  9. tvsally692 says:

    ooooooooo OMG, This article is spot on. Before I married my wife Wanda, on our third date I went down on her to suck her pussy in her mother’s house while she was on a date with her black lover. Both were WHITE. While driving home I told Wanda that I’d like to MARRY her. During the next year I always ate her pussy at her house and several times her mother and her BULL saw us engaged in 69. Wife was 23, her mom was 45 and a widow, her BULL was 55. After we married Wanda told me that both of them sexually pleased the BULL. I was shocked but got an erection!!! Some how that excited me. It was then that I knew I often swallowed the black bulls CUM as I ate my wife. I asked her and she said it’s true and her mother knew about it. I knew I couldn’t please Wanda sexually so I accepted my place in our marriage; I was turned out as a sissy cuckold and began pleasing her mother and the bull who fucked my wife too. I sucked his black cock, ate my mother in law’s CUM filled pussy and ate it out of my wife too. I really enjoyed the arrangement and ever was fucked by the house bull as Wanda and her mother watched. A dream situation for any feminine sissy, I think.

    • [email protected] says:

      dammmmmmmmnnnn it looks like a fairy tails
      every sissy in this world crave to experience that, in fact i know any sissy’s heart squeez of jealousy
      you blown my tiny sissy whore minde and if it’s not about my fear of mistress Alyssa denial cuming, i’d love to rub my clit till i squirt imagining all these scens reminde me of ‘coxville curse’ art work of kitty and her mom jenny <3

    • sissy Glenda Walker says:

      Now this is my favorite story in these comments! If my teenieweenie could get hard, it would be after reading this! i need to print this so my Wife can “accidentally” find it on the printer! i would be thrilled to be in your position…i fantasize about your exact situation!!!

  10. maidjenny says:

    I often lock myself in my cage before i put my maid uniform on and i have even posted the keys back to myself. It would be nice to find someone to take total control of my tiny cock. curtsy from jenny

  11. sissy cynthia says:

    “to help you gather your courage (or rather submissiveness) and open this door (or rather to lock yourself in). ”

    And everything else in this so perfectly written essay is so true … We all know it, don’t we?

    Thank you Academy Board for publishing articles, essays & truths like this! It’s helping us sissies enormously accepting our best possible future and following the path you’re guiding us on – to be ourselves indeed!
    To be that service oriented submissive sissy we must indeed “re-direct our sexual energy to more useful activities.”
    Again – a statement that has 100% more truth and value than a sissy has real man qualities which we don’t have!

    And how about this one:

    “If you embrace your role as a sissy cuckold, then it doesn’t matter why you can’t satisfy your wife. You just can’t. Not in a conventional way at least. Well, how can you, when your clitty is locked up, right? It’s something you can’t fight. It’s another decision made for you. It’s a true acceptance of your submission, and it comes with all the benefits that being a submissive brings you.”

    Face it fellow sissies – this is the real deal. The real truth. The only truth.
    It’s what we want.
    And it’s what our Superiors expect from us…

    “You’re not as attractive, not as good in bed, and you should just stay in your little chastity cage because in the long run that will make you happier. It’s not even a competition, so why stress about it?”

    Embrace the shame.
    And wake up as a natural born sissy ..

    Thank You Academy Board Superiors!

    • Joanne says:

      So true cynthia. I have tried to pretend I am not that submissive sissy but the shameful truth is that I am. It makes such sense for me to be a sissy cuckold for my partner. She deserves much better sex than I can give her. All said in the academy’s ‘Love, sex and chastity’ is true. I need to be locked up and cuckolded.

  12. Mollylovesxox says:

    This story is so inspiring and makes me feel souch more comfortable about my inner secrets.

    I’ve opened up to my fiancee about wanting to be cucked and locked. I am locked quite alot now but she is to shy for cuking me… I can’t be too lucky then… It would make my day to serve her and her bull… But alas a girl might always have to dream. I am not yet fully disclosed my sissy side either but reading here and other stories makes me feel more confident about talking about it. Thank you xxx

  13. Alissa says:

    As a guy with a very small cock I think its only right for my wife to try a bigger penis. Preferably a bbc. I would love nothing more then to stay in chastity while she gets pleased. Its only right when your penis is barely 4 inches and a little thicker then a magic marker.

  14. Sissy Shelley says:

    I would-be for a chance to chase my fantasy and become the woman I was meant to be. Justthi king about having a beautiful powerfully elegant Mistress or Dom tell me what to do to pleasure her and whoever and be locked up the whole time while being plugged and become a sexy feminine sissyboi

  15. Abby says:

    My wife cuckolded me with a guy we had over. She wanted me to suck his cock and get him hard for her. It brought a flood of emotions watching my wife quickly jump on his cock and start riding. She made me record them having sex, her ass bounced and she rode him harder than she does me and she moaned considerably. All those emotions made me feel even more submissive. His cock slipped out and without hesitation I found myself putting it back inside her where it needed to be, giving her amazing pussy all the pleasure she needed. He laid her back and held her legs up and fucked her good, she moaned as he cummed inside her. After he pulled out she told me to clean his cock, it was surreal tasting her pussy and his cum and being their clean up bitch. She then made me clean her up too. Ever since, she’s made me go out and pleasure men, last weekend she said she should meet someone on tinder and do it again..

  16. Алина says:

    a sissy cuckold relationship in the family is the ideal relationship, it helps to be a more caring sissy towards his wife and children.

  17. Jezzebellia says:

    The first woman, to fuck me like a bitch, would always say “you like my cock? Wait until a guy puts a real one in your guts, a real one is even better”. I’d put my face down and my ass up, arch my back, and dream about a bbc pounding on my broken ass like she was. Literally fucking any masculinity out of my cockslot and my sexuality itself. Id thrust onto her big wet prick in challenge. Id grin to myself when she met my challenge. Taking dick in my cunt is so sexy. I look forward to being a full service sissy cuck when i find a woman to get cucked by. I know im a tiny dick little bitch whos penis cannot compare to most others, so i accept and love my role as a fucktoy for my womans bull. God i hope she makes it a black cock.
    Thank you for these blogs, my little dicklette has been hard the entire time ive been on your site!

    • Myers says:

      I find sex to be a chore. Quite frankly, I have no interest in it anymore so I’m certainly open to cuckolding. I’m 8″ erect so size isn’t the issue here nor am I a sissy. If some guy wants me to suck his cock and use my mouth to get hard so he can bang her, I’m down with it. He can also use my mouth as a cum receptacle or give me a facial if he wants, as long as my girlfriend gets satisfied and enjoys it.

  18. maidjenny says:

    I would love for someone to serve when I am in my sissy maid uniform. I am glad I was in chastity reading that as I got so excited.

  19. Paloma says:

    I really enjoy wearing women’s underwear and being locked in a chastity cage for short periods without my wife knowing she has a dominant character and that is something that I love about her I love her very much and she loves me but I know I don’t I satisfy myself sexually, I want the best for her, my greatest wish is to ask her to make me her sissy, feminize me and keep me in permanent chastity so that she can enjoy real men at will, I know that would make her very happy, my Happiness would be to stop playing the role of a man and assume the role of a submissive sissy by her side to be able to serve her in whatever she asks me to do. I think this academy would help me a lot to reaffirm what a sissy I am to let out the submissive and repressed feminine side What is in me and if I can take the long-awaited step before her and society.

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