SISSY CUCKOLD HISTORY 958.
Over the years I have spoken to endless feminized sissy cuckolds and each and every one of them all say that from the offset when they were very young they knew that they were different to other boys.
Growing up was an internal struggle as the sissy inside gradually became larger and larger taking over as the cross dressing got more insistent and worse, the fantasy life and masturbation veered totally off the expected path.
For many they did not develop the way other lads were doing dooming them to small penis humiliation on top of all the other fetishes that they were gathering over time.
By the time dating reared its ugly head the budding feminized sissy cuckold was solidly on to a loser it was never going to be taken seriously as a male and from then on it was only going to be a very special lady that would pick it.
Hence you find that many sissy cuckolds are very successful in their chosen career knowing that being able to keep a woman in the lap of luxury was and is the only path to having and retaining a wife even if that wife insists on being a Cuckoldress.

SISSY CUCKOLD HISTORY 957.
If you are just setting out on your life journey to become a feminized sissy cuckold one thing you should be fully aware of is the Shop Assistant.
No matter what you do and how you sidle into the women’s clothing department they can see you coming, it’s like they have an inbuilt radar to spot sissy cuckolds and oh boy do they love to expose and tease the little lamb as they become overly helpful with their voices raised so all and sundry hears the pointed humiliating questions about size needed and if you have lied and said the things are for the wife she may well slip in little kicks like “Is this for your wife to wear on a date?”
What you will find on your life journey is that every visit to a shop can and will turn into a shameful but ultimately thrilling adventure for you, just wait till you have to go to a pharmacy and ask the lady assistant for extra small condoms and then extra-large for your wife’s boyfriend!

SISSY CUCKOLD HISTORY 956.
How do you tell your wife that you want to be her feminized sissy cuckold maid and slave.
It’s a thorny issue and one that can be approached in many different ways and of course none of them are guaranteed.
Hopefully if you are craving to be a sissy cuckold your good lady wife might already be having an affair as so many married women do so if you discover this infidelity the whole coming clean about yourself becomes so much easier and has a very good chance of success.
If on the other hand your wife is not but seems to be one of those women that like the attention of men and flirting always seemingly looking to make sure she is still alluring and attractive to the opposite sex then you can help things along such as developing premature ejaculation which is a good way of giving her a little push in the right direction.
As you do this give her all the more space to look at and be with other men, encourage the girls’ nights out, appraise the things she wears on her nights out, go shopping with her and suggest even hotter outfits.
Do more or take over the things like cleaning the house, point out guys that ogle her saying that she is being watched by a hunk and your proud that she turns men on.
Might be a good idea at some point to let yourself be caught out dressed up as a woman doing housework or whatever thus opening the door to that very frank conversation that you need to have.
Whatever way you decide to proceed take it easy don’t drop it like a bomb on her little steps before the revelation will condition her not to be overly surprised that something is troubling you thus the confession will fall on receptive ground and she might just have some shocking confessions to make to you already.

SISSY CUCKOLD HISTORY 955.
Locked away in chastity as many of us feminized sissy cuckolds have been or are for extended periods of time we all know the world of utter sexual frustration and torment the state of chaste brings.
Let’s face it being a feminized sissy cuckold mean’s you already live in a constant state of sexual enhancement what with the nylons, lingerie, women’s clothes and the sights and actions of a slutty cuckoldress wife forever in your face or mind if she’s out dating.
Then you add the chastity on top and it becomes explosive, you literally shake in weakness and need at the sound of high heels clicking or the scent of that whore water perfume she wears and that’s before you see her red painted lips around her boyfriend’s cock or her cunt riding his huge length making all sorts of squelching sounds and filling the room with their fuck aroma.
Oh, and the pain you suffer as your tiny penis tries again and again to fight the device locked in place.
And maybe even though your locked up and suffering you might still be able to dribble your pathetic little mess at the sight of his cock plundering her anus and your wife is screaming in utter pleasure!

SISSY CUCKOLD HISTORY 954.
Having walked on this planet for many a year I often look back and mull over just how far us Feminized sissy cuckolds have come.
We all know that there has been transvestites and crossdressers since clothes were first invented, but I sort of place the pips of seed way back to the start of slavery.
Now to be fair there was from the onset all types of slavery, mattered not what your color was the fact was someone was out to get you and sell you and we know in certain parts of the world this practice carries on to this day just goes to show what backward savages some humans still are.
Anyway, I digress and for the white male I zero in on the Negro slave trade, from the offset I think that all involved knew it was wrong at an unconscious level but as they say money is money, so the peculiar institution went on.
Of course, bringing over the captured slaves ended up exposing them to the white female inhabitants of the purchasing nations who by nature are the finest selection of potent masculinity and one can hardly blame femininity as they sat on the veranda’s of the plantation houses watching large negro males stripped to the waist toiling away all muscular and sweaty getting the vapors’ as it was once called.
Pretty soon these ladies also learned that the black men slaving for their husbands were very unlike their husbands when it came to manhood’s.
There is a saying what’s good for the goose is good for the dander and it probably aptly describes what happened back then when the white wife’s discovered their husbands were rutting black wench slaves and she picked up on the sly comments between her housemaids about little penises, pathetic love making, premature ejaculations and so forth and sordid tales of what Lincoln, Paul, Lemar and millions of others had between their legs.
As we know Mistresses of plantations tended to have very close relationships with their housemaids and its not to much of a stretch to surmise that they too were soon in on the disparaging of the white male plantation owner and then the arranged sexual trysts with the black well hung field hand who although lacked any formal education seemed to have an inbred ability to pleasure a woman in every possible way bringing her to untold heights of sexual gratification and massive life changing climaxes.
Of course this changed the nature of the white wife to her husband with her becoming more dominant and even to the stage where she openly flaunted her sex life in front of her husband as he would be ruined if it came out his demure white pretty wife was bedding every negro on the plantation and of course in the process some of these husbands found out that they to were sexually aroused seeing their wives being fucked to paradise by men that they could not even think of competing with.
Thus, the oft stated myth (or should we accept fact in most instances) of the Big black Cock.

SISSY CUCKOLD HISTORY 953.
One thing all Feminized sissy cuckold come to learn is that there is no end or red line to the humiliation and degradation they will accept when serving a Cuckoldress.
The feminized sissy cuckold might start off with saying about certain things I would never do that! But believe me the astute Cuckoldress will forever be pushing the boundaries and if the sissy cuckold knows what’s good for him he will buckle to her wants and needs because let’s face it what Cuckoldress wants a sissy cuckold who does not jump to any and all her commands.

SISSY CUCKOLD HISTORY 952.
Being caught masturbating can be one of the most humiliating and traumatic times in a budding feminized sissy cuckolds’ life.
Specially is the said sissy cuckold want to be is clad in women’s hosiery and lingerie and even a spot of makeup.
What is the bigger shock to the discovering woman most often the mother in these situations, but it could be an aunt or one of the sissies Mothers Girlfriends or even a sister.
Is the bigger shock catching you en-femme or is it the shocking tiny appendage you call a penis although most would take one look and name it a joke!
The savvy Mother or other female can at this moment do all sorts of things and laughing can be the obvious cruel humiliating first step in shaming the little sissy wanker and then lead to a full appraisal of what she has discovered and the unmasking of a future feminized sissy cuckold.
That laugh and ridicule is life changing and humiliating to the budding sissy cuckold something it will never recover from, a shame so deep that once the subject of chastity comes up the sissy cuckold will meekly accept its fate.

SISSY CUCKOLD HISTORY 951.
There is nothing more off putting to the budding feminized sissy cuckold than the weak subbie feeble girl, if you think about it that’s because that is what is developing inside of us.
No, we are from the go get attracted to strong domineering women who control and take what they want leaving us in utter awe and a frenzy of need to serve.
We know already because of our development that we can no way give her what a real man can and what she likes when it comes to sex and so our pathetic little minds seek for a way to be useful and pleasing to such women.
And thus, you have the basis of what most female led relationships are about and how it leads to the Cuckoldress supreme.

SISSY CUCKOLD HISTORY 950.
I know being a feminized sissy cuckold basically marks you out for as much shame, ridicule and humiliation as anyone wants to heap on you not to mention how you feel about yourself.
But stop and think for just a moment, yes your wife debases you at all times as is her right to do as is the snide hurtful comments from other women but see beyond the horrors they foist on you and see that women in general know what an absolute peach you are almost indispensable once they have the status of a cuckoldress wife.
The freedom you being her feminized sissy cuckold gives her is massive from the housework, mundane tasks to the creampie cleaning and toilet duties, no one else would adoringly do these things for a woman so you can quietly class yourself as special.

SISSY CUCKOLD HISTORY 949.
Yesterday I wrote about want to be sissy cuckolds finding the older more mature woman to serve and some helpful hints to make yourself useful to them even before you tell them what you are and how you want to serve them.
Today I want to talk to you about another pool of ladies that I personally have found a rich source of understanding and acceptance and this is the very elderly woman.
This group of females include a lot of divorcees and of course widows, many would day that these old biddies are totally well past sell by date and my answer to that is fuck off!
In my experience I have found that Grannies are some of the most receptive women around and they are as kinky as fuck as they know that they are in last chance saloon because of their age and will grab every opportunity with gusto.
Of course for the old woman she might not actually want penetrative sex but she sure is pleased to have a feminize sissy cuckold that will actually lick the unlickable holes she has that always seem to have a nasty UTI and are in a constant messy state due to double incontinence.
The oldest female I have been with was eighty-seven a lady of skin and bones and liver spots but oh boy was she a kinky lady doing some really freaky stuff to me and had a constant need to be licked to orgasm, orgasms that she never thought she would experience again
Let me tell you licking up her shit smeared ass was a delightful experience apart from the fact that Julie had forced her walking stick up my ass just for jollies.
Of course, they also love the housework and little odd jobs the feminized sissy cuckold can do under their guidance and because of their age and experience they know they have to do things to really stop the sissy cuckold eye wandering.
Take Rose the lady I do many things for she has gone from being a conservative prim woman to a real sadist of a elderly cuckoldress, take last summer I was out in her garden painting her shed dressed just in tights a denim skirt and loose blouse as it was sweltering hot.
Rose came out at lunchtime and invited me to sit with her at her patio table where she handed me a full glass of her acidic hot murky urine to quaff down and then the plate of sandwiches to eat which turned out to be shit sandwiches with tomatoes (Rose really has a devilish sense of humor)
So my advice is to be chatty and calm around the elderly woman, show interest in her compliment her because at first she just will not believe you can want an elderly lady like her, attain friendship and do things like taking her for lunch or just tea, help her to go shopping, buy her little gifts the style of tights or stockings she wears, flowers and keep being open and truthful about yourself tell her you certainly do not or ever will force yourself on her if she honors you with a real date as you are a submissive feminized sissy cuckold and want to worship and adore her.
Believe me with her interest peaked she will want to meet your feminine side, for me I have met ladies when I was dressed and they approached me to find out about myself and that’s when they find out that I am a feminized sissy cuckold and what they can get out of me and it seems to work because I don’t go all heavy and let then set the pace.
Lastly I have yet to meet an elderly woman that does not like her feet kissing licking and sucking it relaxes them so much!