SISSY CUCKOLD HISTORY 896.
It’s a very scary thing when you become an actual Feminized sissy cuckold because of the total and absolute handing over of all power and control of your life to another person.
You can get off on the fantasy to your hearts content but to actually give up all your rights as a human to another is daunting to say the least and thankfully a loving Cuckoldress will understand this and will make the transition for you as painless as possible.
This is a knack that women have the ability to lure and seduce, her femininity and sex will gain her everything for you by teasing and denial with brutal violence only being the last resort to get you to comply.
In many instances the Cuckoldress will be adept enough to talk to the new feminized sissy cuckold in such a way that it will under its own recognizance come to believe that what is being proposed to him is actually logical an in many ways something that he wants and needs.
Put simply as many Cuckoldress wives will tell you it’s all about breaking the new feminized sissy cuckold down to its lowest form before building it up again in the image she wants and demands of a maid and slave serving her with no thought to itself.
SISSY CUCKOLD HISTORY 895.
I wonder how many feminized sissy cuckolds get to the stage that getting an erection naturally is an almost impossible task?
I know I got there years ago via a toxic mix of long-term chastity, Cuckoldress brainwashing, porn addiction and belief that as a Feminized sissy cuckold I was and am shamefully insignificant.
When it’s drummed into you that your tiny, small and worthless and no woman would ever want you and if you do get erect seeing your cuckoldress in any form of undress you get harshly punished or having a stiffie when she is making you watch her have sex with a lover your abilities to function soon start to dissipate due to the consequences.
The Cuckoldress will also harshly teach her feminized sissy cuckold only to erect when she says so or she links being screwed in the sissy pussy with the consent from her to erect.
Even to this day I cannot erect normally and to obtain a shameful sissy squirt it has to be accompanied by large insertions into my sissy pussy and long hard fucking as I watch disgusting porn on our life subject.
I truly am a pathetic feminized sissy cuckold like so many of you are as well.
SISSY CUCKOLD HISTORY 894.
Deep down I think all of us feminized sissy cuckolds know that when we started out dressing up and masturbating we knew we were going to one day suck cock and swallow sperm from the moment we started to ingest our own weak watery sissy milk.
Our conditioning to be male of course made this a very taboo subject that brought on shame and self-loathing when the thoughts of it sprang to mind.
But let’s be honest we all peeked at the big boys in the showers and public toilets all to aware of our massive inferiority in the penis league and the fear we felt with the giddiness to have a cock in our mouths.
Of course women can sense and see this in the likes of us and take advantage of getting us to clean them up after they have had sex with other men but it’s more than that as from talking to many Cuckoldresses they also like seeing sissies and men having sex or sissy on sissy it gives them a perverse thrill knowing they have the power to order such depravities for her entertainment.
Three weeks down on the 2025 Sexmas Advent Calendar, so make sure you check it out if you haven't been keeping up. With 3 days left to go, my 300th gallery will be dropped on Christmas Day as present for all of you.
SISSY CUCKOLD HISTORY 893.
If you were lucky growing up and began evolving into a Feminized sissy cuckold you had a helping guiding hand.
Even if your secret was well hidden I hope you paid attention to your mother or aunt teaching you all you need to know about home economics and housework.
It’s a young want to be feminized sissy cuckold that understands that at some point what it wants to be will encompass toiling as a maid for a wife and will pay detailed interest at the knowledge that being imparted to him.
I was lucky my mother instilled the lot in me from cooking, cleaning, Ironing, sewing in fact every aspect of looking after myself of the lady I was with.
It’s at this point as an evolving feminized sissy cuckold that you realize that what you are about to become is going to be a life filling role and not just a sexual thing.
SISSY CUCKOLD HISTORY 892.
On the rare occasions the Cuckoldress wife lowers herself to let her feminized sissy cuckold have a sissy squirt she usually makes this experience a very uncomfortable one.
I think we all know that nothing is as it seems with the Cuckoldress where sissy release is concerned.
If you are unlucky enough to have a unauthorized accident in your panties or as you kneel or sit watching her have sex with a guy or men the consequences of course are harsh with canings, floggings or whippings.
But then your lucky day arrives and she informs you she is going to make you squirt for her, and you are in paradise, but once the chastity devices come off and out your joy mostly is very short lived.
Your Cuckoldress might only remove your anal chastity and dildo you to a sissy milking the pain of the penile chastity taking away any luxury pleasure, she might also deem is necessary that for some reason needles need pushing through your sissy ovaries or sissy clit head prior to the forced sissy dribble.
Then there is the array of electric toys that can make the sissy clit want to retreat into itself as it’s masturbated by the cuckoldress hand.
Often with the skilled Cuckoldress she will do what’s called a draining which amount to no stop manual masturbation drawing out every last drop of sissy milk and then some to the point of having her feminized sissy cuckold screaming and pleading to be put back in chastity as its sissy clit and ovaries are hurting so much with the relentless masturbation.
In many ways over time the feminized sissy cuckold comes to understand that no cumming and living with enduring sexual frustration is the best course of action.
SISSY CUCKOLD HISTORY 891.
You know you’re a full blown feminized sissy cuckold when you discover the feeling of seeing someone you like going off with other men and you get aroused by the humiliation even if the said girl does not even know you adore her.
From the moment we start our dressing up and it aids our dirty naughty little masturbation sessions we know there is something wrong with us and fiddling with ourselves is a shameful bad naughty thing that we really should not be doing to ourselves but cannot help it.
Worse if a woman catches us dressed up and wanking because their reaction to our perverted cavorting’s will instill a deep-seated shame and humiliation in us that we are not good enough to be allowed to masturbate so by default there is no possible way we should be bothering women for sexual intercourse.
Even before we discover what we are most feminized sissy cuckold know that they are small and underdeveloped in the manhood stakes and it becomes in bred into us that we must help and support women have sex with real men our only role to serve the lady and clean her up.
SISSY CUCKOLD HISTORY 890.
Here we are almost at Christmas again and this time of year can be especially exciting for the feminized sissy cuckold what with all the parties your wife will be going to and even taking you along to some of them.
For sure she will let her hair down and be more wanton and sluttier than per usual due to the merry making and you know from the way she dresses and acts there will be a never-ending stream of guys wanting to get into her knickers (that’s if she ever wore any?)
Then there is the actual day and what presents you might get? Remember the shit years when you were a so-called man and you used to get socks and aftershave how boring was that eh? Now you get nightwear, lingerie and hosiery, bits of makeup and any other items of female apparel your cuckoldress, Mother-in-law or even Mother decides would be nice for you.
Oh, and for your feminized sissy cuckolds that the wife has made to have a boyfriend you of course will be expected to make sure he is fully sexually satisfied over the Christmas period, it’s not only the turkey that gets stuffed over yuletide.
SISSY CUCKOLD FUTURE 889.
Once you become a feminized sissy cuckold to be used and abused by your cuckoldress she will also use you for her entertainment.
This will obviously entail doing homosexual things that you had better get used to pretty damn fast if you know what’s good for you or you’ll be on the receiving end of your wife’s displeasure as she teaches you the hard way to be a happy compliant sissy cuckold.
One of the first things you’ll have to accept and cope with is that when guys go with the likes of us because they look on us as sexual freaks they will push the biscuit as the saying goes and subject you to their idea of what a trollop sissy slut likes so get ready for brutal balls deep skull fucking that will have you heaving up and drooling all round his throat fucking cock as you struggle to cope with the assault
He will slap your chin or squish his balls into your eye sockets depending how he is inserting himself into your orifice and will not stop his pleasure until he spews his spunk straight into your stomach as deeply as he is able.
Be ready afterwards to lavish his cock with kisses and licks no matter what sticky drool mess it’s in and smile happily as you’re doing it your wife must see that your well into being used as a sissy whore.
And then do not forget to ask permission to retire to the bathroom to re do your make up as that will be a fucking mess!