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Chastity Cuckold – graduating from simple chastity to Cuckold

23-11-2019 - Written by Jett Oxy - Follow on medium 


Advancing from simple male chastity to cuckolding chastity is an exciting move in a relationship. Yet, it is not always a natural transition, considering that the man in the picture does not especially fantasies about his wife cuckolding him. The process is also somewhat slow-moving from chastity to the introduction and adoption of the new dimensions of cuckolding. Cuckold training involves some periodic sex denials, which, according to most people, is the most exciting part of the journey. 


In addition to taking away your much-needed orgasms, chastity cuckolding also involves your wife giving other men orgasms without you getting any. Imagine your pathetic cock staying locked in the micro chastity cock cage while your wife pleasures another man’s hard on. 


Cuckolding is the aspect added to “standard” chastity play, a combination bringing painful pleasure to many men. This fetish is getting so popular that several cuckold dating sites are designed to help men meet their cuckold partners or undergo Cuckold training.


After the man has gotten used to semi-permanent or permanent male chastity (when the cock is locked in a cage for long period of time) – the female keyholder can start exploring a cuckold chastity lifestyle. Reaching such a level of dominance is rewarding in all instances of a dom/sub relationship. 


Yet, not always an easy task for the keyholder. the caged may continuously beg to orgasm while constantly reiterating his unwillingness to be part of such a process in the first instance. He may also raise the issue of discomfort and the need for more frequent releases. The keyholder will need to be resolute and consistent to overlook these rants and pleads. Hence, a man that is willing to participate in permanent male chastity must be ready to do so on the terms of the keyholder. 


Anything other than this will mean deviating from the conventional chastity arrangement. Although it requires consistent efforts and dedication, it all becomes smooth and enjoyable for both parties after the acceptance stage and the establishment of the dominance stage. It is common for the keyholder to worry about the lack of penetrative sex, considering that the penis is not available for intercourse. Even in rare cases where the penis is released, an attempt to penetrate will feel very foreign and lead to a premature, hair-trigger orgasm. 


The keyholder will find such sexual incompetence unsatisfactory for her own pleasure, thus forcing her to resort to dildo or other toys to get penetrated. However, what happens when the keyholder prefers a real penis than sex toys? This is when, Chastity Cuckolding comes into the picture. 

Cuckold Chastity

Getting Familiar with the Cuckold Chastity Lifestyle


Many men fantasize about being cuckolded by their wife or another keyholder. However, only a few can live with the emasculation, humiliating feelings, jealous, and inadequacy that come with the lifestyle. For them, the entire arrangement can be disgusted, especially the part where they are forced to watch their significant partner have sex with some random men.


Perhaps, such men have failed to realize that in this game, the woman entirely calls the shot. Hence, she wants all her needs and desires met. The fact that the man or his genitals are unavailable doesn’t mean she doesn’t deserve to be pleasured. Considering these compromises, it is essential for a couple involved in a male chastity lifestyle to build the same on a strong and inequitable foundation. With such a formidable foundation, attaining the emotional intimacy required for such a special relationship becomes easier.No couple should go into a chastity cuckold relationship without putting in many thoughts and salient considerations.


Once the decision to move from male chastity to male cuckold chastity has been made, the keyholder can now exercise her freedom and, of course, feminine power. There are two men at her disposal – a compliant and responsive man that meet her daily needs (The cuck)and another one that she can go on sexual escapades with (the bull).


So, chastity cuckolding is an avenue for the keyholder to show her dominion of dominance and simultaneously remind and reaffirm the submission of the man. Here are some popular chastity cuckolding most keyholders like to explore as part of Cuckold training or lifestyle;

 

  • Having the cuck sleep on the floor right next to the bed while the bull spends the night with her on the bed. 
  • Fucking the cuck with a strap-on, with the bull watching and the key to the cock cage lying seductively on her tits. 
  • Ordering the cuck to do some house chores while she is making out with the bull.
  • Making the cuck welcome the bull at the door by kneeling while naked. 
  • Having the cuck go out with her to the bar with the chastity device on while she flirts and fondles random men.
  • Making the cuck dress up, wearing high heels, lingerie, and complete makeup, so that he can take her place and satisfy the bull whenever she doesn’t feel like it.
  • Having the cuck prepare her dress, shoes, and underwear while she prepares for a date with the bull. 
  • Having the cuck fluff her as a form of foreplay before the real sex with the bull.
  • Asking her bull to fuck the cuck in the ass while she pleasures herself with sex toys – a means to affirm further who the real man of the house is. 

Each of these scenes is all fun for the keyholder but rather humiliating and devastating for the chastity cuckold. Yet, she is fulfilling the cuckold fantasy.


Male chastity and cuckolding or sissy cuckold will turn out to be an excellent symbiotic relationship if only both parties are ready to do what is required of them in their respective roles. The lifestyle is one that can give a man the most intense waves of submission and servitude. 


Article Written by Jett Oxy for oxy-shop.com. 

Jett is the owner of Oxy-shop.com, a BDSM insider, a sex educator and writer. 

"I always try to explore the confines of the BDSM world and bring valuable insights for new comers joining our adventure" 

Phd in related field, father and business owner, Jett Oxy brings you stories and advices  for educational and entertainment purposes. 


Follow on medium - Follow on twitter 


8 Responses

Violet or sissywannaB
Violet or sissywannaB

December 13, 2019

What’s the easiest way to have this happen? Do I dress up and chastitize myself as well as invite a bull over and maybe a dominant mistress to show my gf what to do and convince her of how much fun she will have without any jealousy or things not going her way. What could I say if she asked the bull to cum in her sissy bitchs pussy and then have me clean both of them up using my tongue of course , getting plenty of pictures and video to watch later as well as upload to the internet so the whole world can see too as it all goes down. I would soo love this very much. And if my gf doesn’t start it will anyone who is a professional in a sense come on over for a good time, or pick us up so I can demonstrate my sissy maid skills while the bull shows my gf his skills which she will Need from that point on to cum herself.. Which will make it all easier for her if my cock is locked up indefinitely till it suddenly disappears while I am asleep.. Which I will reply I Love It!! If either or anyone asks how I like it! And if it is mounted on a keychain for my gf to keep in her purse or hang from rear view mirror so she knows it is hers forever. Am I a twisted freak who will never live my fantasy out for my whole remaining life.. Please if anyone is interested in having a little fun. Please feel free to do so asap…

SissyWannaB
SissyWannaB

December 12, 2019

I fantasize and wish . even beg by sharing pages like these saying she should try it. If she doesn’t wish someone would jump in and do it..please

Imperfectionist
Imperfectionist

December 08, 2019

One of the most important things you mention is that this can be a slow transition. My now ex-wife tried to lead me down the cuckolding path but her approach was more of an ultimatum which I wasn’t ready for at the time. I regret not going along with it now but Ialso think if she had taken more time I would have eventually been happy to do it for her.

Wrayford Wayne
Wrayford Wayne

December 07, 2019

Good article. That very last few sentences sum it up completely: “Male chastity and cuckolding or (becoming a) sissy cuckold will turn out to be an excellent symbiotic relationship if only both parties are ready to do what is required of them in their respective roles.” SOOOO true! I am an experienced AND REAL cuck. I did not have to be convinced to be humiliated or get upset if I had to do something subserviant in any way. I thrived on it. I craved it. The more humiliating and degrading to my manhood, the better. Why? Because that’s what being a (modern) cuck means. I/we learned of male chastity after the fact, but it was the bees knees, boi, when it came to being cucked! A cock cage is medieval cool! More importantly though, wearing a chastity cage clearly means one thing for a cuck hubby = YOUR DICKLET/CLIT IS NOT WHAT’S IMPORTANT AND DOES NOT MATTER! A professed cuck should not put one on unless he is willing to live 100%, WITHOUT QUESTION, by that creed. Indeed, it IS what turns us on and HOW WE GET OFF as true cucks, not just the act of a cummie – a cummie is a side effect iF YOU’RE LUCKY OR ALLOWED TO HAVE ONE. Undertstand? There is no place for pride “as a man” when you are a cuck. If you can’t do that…the cuckolding lifestyle is NOT for you and you may try just being dominated by the female only. My guess is that (you) will have issues with that as well, though, if you are not willing to 100% commit to what wearing chastity means.

Mick
Mick

December 07, 2019

It irks me that our ladies won’t allow us to get pleasure any other way knowing they won’t sleep with us. My situation is not what i want in a relationship.

-Unhappy in Hollywood

Mikki
Mikki

December 06, 2019

Miles,
I understand your wants and needs. I am in Ct and a sexless marriage too.

miles
miles

December 06, 2019

I only with I could experience this any one know some one willing to help me find out what it is like I live in Connecticut . and I am in a sexless marrage she would never go for it but I a willing to try with any one
miles

Ted
Ted

December 06, 2019

The article is pretty much bang on .It describes my life exactly .I would add that my wife/ mistress and her “bull” have over time developed a sadistic streak which grows more intense .I fully realize I can leave the arrangement when ever I want ,but I am very much in love with my wife ,who by the way is uber hot and she professes her love for me .The way it has played out is exactly what I want ,so in effect it is I who ultimately calling the shots by my complete submissiveness to them both .Having to satisfy the bull still does not sit well with me ,,it is one of the many conditions I have agreed to ,so I continue to obey .

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