SISSY CUCKOLD HISTORY 837.
It would be a mistake to state that all married women will be ok with you coming out as a feminized sissy cuckold begging them to become your cuckoldress, so the budding sissy cuckold will have to come to terms with the fact it might get dumped and divorced.
Is that a bad thing? Well in the long run no as the woman you were married to was at the end of the day not the right person for you nor you Her’s.
But despair not as many, many married women are more than happy to indulge in the Cuckoldress lifestyle as it lets them be attractive alluring wanted females again with the steady wall of a marriage to go with it and come on tell me a woman that does not want a maid doing all the housework to perfection under the real threat and dealing out of punishment.
Wives will also after a little (and I mean little) consideration fully embrace and practice chastity for their sissy husband as now a Cuckoldress they understand how small and insignificant their husbands penis is and certainly don’t want anything to do with it apart from infrequent pity wanks, she certainly does not want her sissy cuckold husband fiddling with himself and squirting all-round the house let alone having erections (If it’s not big enough to be called a cock then what reason has a penis to erect?) this is the sound logic many cuckoldress wives stand by and in essence is totally correct.

SISSY CUCKOLD HISTORY 836.
I will never forget the first time Tania my second wife and Cuckoldress and practicing professional dominatrix made me go into her dungeon and prostitute myself with a homosexual client to earn her money.
I even remember his name Simon a painfully thin lanky tall guy with glasses, I was as nervous and scared as hell greeting Simon as like I have explained before I am not a natural sissy cock sucking queer due to historic abuse.
But I had had more than just a few gay experiences prior to this session Tania had booked me to do.
Remember there was no privacy in what I was having to do as Tania’s dungeon was rigged with spy cameras, and I knew she would be watching make sure I satisfied the client and acted and reacted in the proper whore like manner that she had taught me.
Simon got the tribute out of the way first handing over to me the sixty fee, I left him for a moment to go and give Tania the money while Simon stripped naked and was shaking all over as Tania ordered me back into the dungeon to do my work.
Seeing Simon naked waiting for me in the dungeon made me almost pass out with terror as for a tall thin white guy he was very well endowed his semi flaccid cock hanging almost to his knees.
Simon could clearly see I was a mess of nerves and as I tried to do a slow sexy strip down to my lingerie, high heels and stockings he pressed me with questions about my gay experiences and finally that he was my first punter since my wife had enforced my career change into becoming a feminized sissy cuckold prostitute.
Simon talking did help to calm me a bit and next I was squatting in front of him like a slut holding and caressing his large smooth balls as I suck as much of his huge cock as I could all the way into my throat where I struggled to breath properly and let him face fuck me as he held my head in his hands.
I had a really good taste of Simon as he leaked a huge volume of pre cum and took himself to the edge in my throat three times before getting me up and leaning me over the massage table in the dungeon.
Via the mirrored wall I could see Simon lubricating hugely erect cock up his eyes greedily scanning my lingerie clad sissy cuckold body, strangely Simon before taking me used on of his hands to caress and manipulate my in scared little penis to an aching erection so skilled was his hand.
So, it was with the delightful feeling of my sissy clit being fiddled with that I gasped when the bulbus head of Simon’s hard erect cock pressed against my twitching spasming tight little sphincter.
With more and more pressure being applied by Simon his cock head finally popped into my rectum making me wail in pain at the huge intrusion as my ring was broken into by gay cock.
Simon luckily was a thoughtful guy and knew his cock was something that not many could handle and the next minute one of his hands came in front of my face holding an open bottle with a heady scent in that soon had me spinning my mind and body experiencing a delightful sexy thudding and throbbing and my tortured sissy pussy opening relaxed and I groaned in a shameful slutty manner as Simon eased his large cock all the way into me till his balls slapped hard against my one tight little testie.
Over the next hour Simon showed me what an experienced gay man can do as he fucked me to oblivion with long hard strokes that sent me wild and aided by a few more inhalations of the aroma from the bottle
Tania later told me she had watched ever filthy sordid moment of me servicing a gay punter and teased me unmercifully about how sexually excited I must have been for queer cock as I forgot totally to get Simon to wear a condom so I felt the lot when is cock exploded all the way in me as gout after gout of his hot spunk filled up my bowels and triggered off a sissygasm that Tania saw as my weak watery sissy milk hung like strings from the tip of my hard quivering little penis dropping to the floor once the over stretch had been reached.
To my further shame the session ended with me sucking Simon’s slightly shit soiled and smelling cock clean and he actually kissed me thanking me stating he would be back for more.
Good to his word Simon from then on would come for a session about once every six weeks thus I earned Tania a good whack and like any good Cuckoldress Pimpess I was never allowed to keep any of what I had pedaled my ass and mouth for!

SISSY CUCKOLD HISTORY 835.
For want of a better phrase I suppose I was lucky being caught out evolving into a transvestite early on by my mother who liberally for back then encouraged me dressing up and then via gossip with Pam, Fran and Wendy revealed to me what I was destined to become in life a Feminized sissy cuckold.
At the time when I was exposed, I was in stark terror thinking the world was going to end when my little penis erected against my mother’s silky hot nylon foot when I was massaging her feet one evening whilst we were watching television.
Then came her cutting humiliating remark over how insignificant my little penis was and her going on to say she knew was stealing her tights and panties to wear out of the laundry basket and ordering me to go and put a pair on that were freshly dumped ready for washing.
I obeyed how could I not being in utter fear being caught out and I felt less than an inch tall a while later standing in front of her in the dirty tights my little penis so hard it was hurting.
From that evening onwards I was encouraged to wear her dirty hosiery and panties and over time it was all the time and the rest of female apparel and make up.
Now many Feminized sissy cuckolds I have spoken to do end up getting exposed one way or another mostly via their cuckoldress wife spilling the beans to Sissy Cuckolds mother and contrary to popular opinion in many, many cases the sissy cuckold shaking with fear of it’s wife exposing it to Mummy turns out to be the fact that Mummy has known for a very long time that her son was a crossdressing perverts but preferred not to say anything and shockingly will side with her sons Cuckoldress wife in the lifestyle.
This deep meeting of minds between Mother and Daughter in law is the closest and most meaningful in law relationship that can develop, as both Mother and the wife both want what’s best for the Feminized sissy cuckold.

SISSY CUCKOLD HISTORY 834.
Some of the most humiliating times for the Feminized sissy cuckold are when the Cuckoldress wife really gets off on inflicting shame and humiliation on her feminized husband by cock and penis comparison with whatever boyfriend she is with.
Not only is the husband feminized almost unrecognizable as a male but the cock she is holding in her hand is massively bigger than her sissy cuckolds who’s so sick and perverted it’s erect seeing his wife handling a real cock that puts his own into the shade or should we say so deep in the dark sissy cuckold feels a total sense of worthlessness and shame.
The Skilled Cuckoldress wife will also be expert in applying verbal humiliation at the same time with each word coming from her red paint lips sharper than a cut from a knife often reducing sissy cuckold to tears making him feel even more like a big girl’s blouse in front of its wife’s lover.

SISSY CUCKOLD HISTORY 832.
As a Feminized sissy cuckold one thing I do know is that once you discover yourself you come to understand just how weak and pathetic you really are.
Being a Feminized sissy cuckold takes over your life totally, it’s not something that can be contained in the bedroom as a sexual kink the new sissy cuckold already perverted beyond any reason in it’s want to be stage finds not a waking minute goes by without the issue being at the fore front of it’s so called mind and every action.
By talking to actual Cuckoldress wives over the years they nearly all comment on the lifestyle being a very naughty bit of fun to begin with for bedroom time only to their realization that once their partner comes out as a Feminized sissy cuckold and she agrees to be a Cuckoldress wife that it engulfs their life totally.
No discussion takes place over this change in things as the lifestyle expands and no wife will curtail this as she is now living a life of sexual freedom with essentially a slave doing all the mundane and shitty things in life, she has become an adored and worshipped Princess.
And of course, the feminized sissy cuckold is not going to say shit about having to be what he is all the time.
So, our need and lifestyle is an all-consuming self-building and encapsulating addiction that has no cure ever.

SISSY CUCKOLD HISTORY 831.
Weakness has made me order a range of eye watering horse cock dildos to add to my collection such is the perversities of the feminized sissy cuckold.
The allure for them was sparked a long time ago when I was dating a prostitute called Lucy a large blond very naughty lady and not only was I toiling as her feminized sissy cuckold French maid we would also have evenings together where I would massage her nylon clad feet as well as kissing and sucking them and her anus and pussy we would also chat about our deepest darkest kinks and it transpired that Lucy had a thing for horse cock, she had never done it but she really got off on the idea and would climax violently as I licked her and she talked about it or if I assured her I would be her sissy cuckold clean up girl even if she was doing that! Very stimulating fantasy chat.

SISSY CUCKOLD HISTORY 830.
One thing I have found that’s essential for the feminized sissy cuckold to have in reserve at home all the time is pantyliners.
After the weekend I have just had with Rose my sissy pussy has still not gone back to normal and is loose and slack and still dribbles of ass jelly are leaking out from deep inside of me.
Thus, the pantyliner is a godsent to save from soiling the pretty panties I have on.
And let’s face it as feminized sissy cuckolds it’s not just the barrier to lubrication but at times when we are used by men, we have sperm leaking out of us that needs absorbing as we have not got a creature like a sissy cuckold to lick the mess up!

SISSY CUCKOLD HISTORY 829.
Rose laughed as she picked out of the carry bag the three largest of the new dildo’s saying she could hardly lift them they were so big this said with a glint I her eye.
In all there are sixteen new sex toys that she had me lay out on her sofa so she could inspect each and every one of them touching and lifting and looking over one after the other a rabid look of excitement on her heavily made-up face.
Minutes later she had me licking her wet smelly old pussy her clit so hard with arousal as she gripped onto the big black one until finally she climaxed and ordered me away from her pussy as she pressed the head of the huge black rubber cock to her elderly wet hole and eased it into herself then slowly feeding her cunt full of the cock till three quarters of it was deeply embedded.
Then another climax hit Rise her grey stocking clad legs and low-heeled black shoes shaking in pleasure and when she came down, she ordered me back on her clit and to use my hand to pump the rubber black cock in and out of her cunt.
The result of this sex between us was another massive orgasm out of Rose as her cunt spasmed around the cock inside of her and her bladder emptying into my mouth as she shook and twitched.
Panting afterwards Rose gave me a cheeky but in control smile and spoke “Well Sissy Cuckold Carla it’s your turn now, let’s see how all these toys work on you!”