Sissy Cuckold Thought's, experiences and observations!

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SISSY CUCKOLD HISTORY 655.
One shameful part of my feminized sissy cuckold history was my formative years when I was attracted to everything to do with female hosiery and underwear?
I will admit now with feelings of shameful excitement that when in the company of my ****** and we visited her friends I would use the bathroom and if it was there rifle through the laundry basket and sniff and lick the gussets of the items I found.
What this did to my forming mind was terrible as it was so addictive tasting the secretions of the women I was having very naughty and dirty thoughts about!
But it went further as happened in Sandy's house when I went to her bathroom and near the toilet was bit bin and my eyes caught a see through blue bag dumped in it that contained what could only be a used sanitary towel.
I was almost passing out in fear but attraction when I opened that bag and saw the clotty ****** state of the slime that had come out of her period pussy and I could not help myself but lick the mess which caused me to squirt in my underpants.
Since that time I have never been adverse to sucking sanitary products after they have been used or acting as a sissy cuckold cleaner to any woman on her period.

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SISSY CUCKOLD HISTORY 656.
For me my evolvement into a Feminized Sissy Cuckold was the most shameful humiliating thing I have ever had to go through!
Although my ****** had glided through the episode of me erecting against her nylon clad foot and her outing me and teasing me over the fact she knew I wore her hosiery and made me put a pair on and after that I was in tights a lot at home it was only after the Pam and Fran incidents my first sexual contacts with women that things got much more in intense!
My ******, Pam and Fran and a lady called Wendy were best of friends if that's what you'd call them? they were a close group of late thirties early forties divorcees that would set the town alight when they went out and as I grew to learn they were not backwards in coming forward when it came to entertaining men!
But you can imagine my shock and horror one evening when ****** got home and I am sitting watching television in a pair of her used tights and a frilly knee length nightie she had me wear over them and she settled down and cut the sound to the television and right out asked me if I actually enjoyed licking another man's sperm out of Pam's pussy!
I knew I was cornered as she had obviously been gossiping with Pam who had spilled the beans over what I had seen her doing and then me pleading that night to suck on her stocking clad toes and up her legs to her fucked dirty pussy finally relenting with a sly grin on her face and making me clean her sperm dripping sex.
All I could do was tell the truth as my cheeks burned with shame and *********** and I felt swoony and queasy when ****** reached out and squeezed my nylon clad thigh and smiled telling me she was proud of me!
I was just calming down happy not being told what a disgusting pervert I was when ****** then asked "What exactly did you lick from between Fran's arse cheeks?"
Of course ****** piled the pressure on until I confessed that Fran had got me round to her house one morning and had dressed me up and then demanded me to see to her and she had been very dirty back there and I had licked her clean and had consumed everything else that had come out of her!
I do not think I was able to ever live this exposure and confession down for years and after that there was nothing about my obsessions and kinks that my ****** did not know about me and she was the first person after I got married that I told that I was being Cuckolded to which she was very relaxed about and informed me that she knew that I needed that sort of relationship!

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SISSY CUCKOLD HISTORY 657.
The Feminized sissy cuckold can really cut a sad figure with some of the things the Cuckoldress wife makes it do!
I remember when Tania my 2nd wife the Dominatrix/Escort and Cuckoldress made me have a rubber dolly girlfriend and had me have sex with it taunting me the whole time as I excitedly put my all into the act as I had not had sex for such a long time being locked in chastity.
Tania gasping for air laughing her stockings off shouted words of encouragement as I humped pathetically away at my new girlfriend adding that the lady must not be able to feel me in her as no matter what I was doing she had a bored look on her face!
As I squirmed Tania told me to whisper sweet nothings to my partner and to tell her I loved her and I was sorry being so small I could not satisfy her?
Of course my humping was helped on by well aimed blows of Tania's riding crop and with the verbal encouragement Tania was giving me I came very quickly!
Seconds later I was having to lick the creampie out of the rubber dolly as Tania teased me saying my new girlfriend would not like one little bit that I was a premature ejaculator and if I did not buck my idea's up she would become a Cuckoldress as well!
A few weeks later in another session this came true as Tania had got the old guy who lived a few doors up from us to fuck my plastic girlfriend and I was ****** to clean her creampie pussy in front of Tania and her friend Priddy!

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SISSY CUCKOLD HISTORY 658.
One of the things that has always got me going as a Feminized Sissy Cuckold is what I call the mock sympathy from women.
Like at times I have been to sex or fetish parties with my Cuckoldress and they have been pigging out on cock with all sorts of men as I watch and some other woman has come up and chatted to me.
And they all seem to have that way of trying to express sympathy in a mocking teasing tone of voice that really humiliates a feminized sissy cuckold.
The sorts of things they come out with are outrageous!
"Oh my a wife should not act like yours is even if her husband is a pansy with a little penis!"
"Not much of a man are you letting your wife fuck all these guys in front of you!"
"What a whore that woman is? Oh sorry is that your wife?"
"Must be awful being born with such a small penis that your wife is ****** to dress you up as a sissy and have sex with real men in front of you!"
"Does it taste nice licking their sperm out of your wife's pussy and ass?"
The list goes on and on as women in general can be so inventive with their taunts and put downs once they get going!

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SISSY CUCKOLD HISTORY 659.
There are so many awesome things that the feminized sissy cuckold has to see when it's wife or significant other steps into the Cuckoldress lifestyle.
Of course the height of ecstasy is actually being there as she is getting fucked by a real man or men.
Sitting there all feminized up and probably in chastity is a head trip in itself but to see a massive cock ease into your wife's pussy is like an opiate and you will gasp at how wet and easy she takes his every inch.
What's even more humbling is just how wild and slutty she is having sex with another man as you watch how she teases and taunts him to fuck her every which way in such a whore like manner
I can assure you of one thing she will do things with him or them that she would never even dream of doing with you and get ready to almost pass out at the sight of your wife lowering her sphincter onto a whopping great cock and taking it right up the ass!
Yes that ass that even if you looked at it in the past she would throw a strop and call you a filthy pervert and she would never do that sort of thing!
And here she is taking a cock up her ass and you'll see her have anal orgasms and scream in delight when spunk fills her bowels!
As a Feminized Sissy Cuckold just be content that at least you will be able to touch her bottom now when she feeds you the anal creampies!

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SISSY CUCKOLD HISTORY 660.
One thing that can utterly destroy the Feminized Sissy Cuckold is it's never ending struggle and slaving away to keep the Cuckoldress wife in the custom she becomes used to!
My second ex wife and Cuckoldress Tania proudly used to taunt me that she was high maintenance and believe me every spare penny when on the things she wanted and to do!
Imelda Marcos had nothing on Tania when it came to shoes and hosiery and I suspect? nay I know many small countries did not have the gold reserves to finance what I had to finance.
And it went way beyond clothes, hosiery, shoes, make up etc there was also the car the weekends away with her boyfriends, vacations, lunches with her girlfriends and a million and one other things!
I recall a time we had just returned from vacation from the USA at the time when you were getting over two dollars to the pound and in the two weeks we were there Tania had shopped through 10 thousand dollars on everything she wanted.
On our return home it was just a week or so before payday for me and we were in town picking up a few bits and Tania saw a rather sexy blouse in a store window and demanded I purchased it for her!
I stuttered knowing the consequences but really feeling the pinch at that moment that could she wait till payday?
Of course what I got was Tania exploding in the high street saying "You never buy me anything!" and of course she took the whip to me when we got home!

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SISSY CUCKOLD HISTORY 661.
One of the enduring facets of being a Feminized Sissy Cuckold is the fact that from an early age because you know you are different and somehow incapable everything to do with sex is shameful!
For the Feminized Sissy Cuckold the desire and need for sex is overwhelming and all consuming and everything it does and touches enhances these desires to the point of sexual insanity what with the sure knowledge being slowly learned that it is incapable of any meaningful sexual intimacy and not needed by any other gender.
Thus the to be feminized sissy cuckold will tailor it's sexual expectations to the lowest form of just being a mere slave on hand to do anything a partner thinks of throwing its way?
And quickly the Feminized sissy cuckold will come to enjoy and get a sexual kick out of the degradations and ************ people heap on it and if by some miracle it's ever offered vanilla sex it will find out that it cannot perform normally as one would expect of a human.

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SISSY CUCKOLD HISTORY 662.
As funny as it may seem when it comes to the superior sex you can never know which lady will be interested in a Feminized Sissy Cuckold.
Certainly both my ex wives and Cuckoldresses were beautiful women Tania being utterly stunning with her Jamaican/Latino looks, and Anne way pretty hot what with her gypsy *****.
But as to the other ladies that have decided to use me for their amusement its a totally mixed bag and you can never rely on looks alone?
At times I have looked at the most slutty looking and acting bimbos feeling sure that they needed one such as me but on attempting to approach them I have faced rejection in a manner you'd think she was a virgin????
In general for a Sissy Cuckold want to be your chances are better with an older woman and one that is divorced out for fun for the first time in years and these ladies can be very receptive as they initially do not want heavy ties and are only looking for fun and having a maid and sissy cuckold slave delights them!
The crunch is that they become accustomed to being waited on hand and foot and lots of long term relationships can develop with women such as these.
Then there is that Grannies who I have found are another pool of surprises? many elderly ladies are view as past it and over the hill and this is a mistake as even women in their eighties want to be looked upon as female and still have urges.
The women of this age are also very eager to get pleasure for themselves and will use a feminized sissy cuckold ruthlessly as they come to realize your not kidding in your desire to serve her and the sissy cuckold will suffer utter degradation at the woman's hands as she likes to see how far she can push the biscuit so to speak.
Large ladies also have a fondness for the kink and perversion a feminized sissy cuckold can bring her way and believe me big women tend to be very sexually active with multiple partners so creampie cleaning is paramount with them and so it turns out is tending to her personal hygiene as they revel in the utter degradation of the sissy cuckold maid!
One thing to finish off with today is that younger women are a no go as they have not the world experience to even start handling a feminized sissy cuckold even if they attract you and look so pretty! for me young ladies do nothing for me I much prefer the older woman as they were the group that formed my sexuality in the first place!

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SISSY CUCKOLD HISTORY 663.
As Feminized Sissy Cuckolds we all have our fetishes that are so gripped into our souls that the chains can never be broken!
For me it's legs, feet,toes and hosiery and high heels on women the very sight of a nicely turned ankle in strappy high heels with polished toes showing through hosiery is enough to make me swoon.
Of course I like wearing the stuff myself so I am so gripped in the fetish I am a hopeless case and no help would ever shake me of the urges and desires I have.
And lets remember that's just one fetish I have there are thousands of others that have taken over my whole persona so when someone asks me what I am I can only reply that I am a Feminized Sissy Cuckold as I cannot be classed as either a man or a woman.

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SISSY CUCKOLD HISTORY 665.
I do not know about you but I suspect like me your need to become a Feminized Sissy Cuckold was all consuming as it evolved and came out in you!
I recall spending everyday literally shaking and powerless because of the needs in me that were so strong there was no way I could possibly resist!
And the more you sink the more you dress up and act your sissy self and add fuel to the fire with pornography and then frequenting sex workers to achieve some sort of fix?
But nothing prepares you for the time when you are actually Cuckolded by the woman you love!
When she comes out to you that she has had an affair or got the confession out of you and has decided to become a Cuckoldress you'll experience emotions and feelings both mental and physical that are a million times more intense than you have ever felt before?
Now you are truly lost and can be what you really are as there is no way back of there ever was!

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SISSY CUCKOLD HISTORY 666.
Everything that has happened to you as you grew into your sexuality has gone against the grain of normality? from the dressing up, the encouragement of females in your life who not only teased you unmercifully but instilled into you that you were naughty dressing up but sweet????
Then the years of ogling finely dressed women becoming addicted to the way they looked and acted and starting to realise that you were not developing like the other lads and the men your ******, Sister's, Aunts and other significant women in your life you saw with were men that you were coming to understand you could never be!
People say that penis size does not matter??? well who thought that one up eh? because as a Feminized Sissy Cuckold penis is the big humbler, you have not got one and never will have and it is one of the deep roots of your shame and *********** and once exposed both women and men will think much less of you!
No woman is going to want it that's for sure that's why ladies look for other qualities in you such as you being a good earner, how slavish you are and because you will never be a man the woman that takes you on will cherish the fact that you'll be her feminized sissy cuckold maid and adore and love her while she goes full Cuckoldress on you!

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SISSY CUCKOLD HISTORY 667.
All want to be Feminized Sissy Cuckolds should never hide what they are it is a cardinal sin and cuts down your chances of meeting a Cuckoldress!
Make sure you attend all medical, work or any other appointment dressed as your fem self and be locked in chastity even if you do not have a keyholder.
Being dressed en fem will of course put you in a submissive mode and even more so in chastity specially if it's a hospital or Doctors appointment where your locked up sissy clit will be exposed.
Many a time female doctors and even male ones have had that sly smirk on their lips dying to make some savage comment but are unable to but that smirk contains so much ***********.
Nurses are a different kettle of fish and once they see your open to ridicule they will make devilish little comments that can be taken both ways to be on the safe side and these ladies can really make you squirm?
I had one relationship when after my appendix was taken out I went to the surgery to have my staples removed and the nurse taking them out not only saw my locked up sissy clit but also my tattoo on my pubis "Warning Sissy Cuckold extra small!"
She was literally shaking all over after reading it and traced her finger over the sensitive hairless skin and just ordered me to arrive at her home that Friday night!
Upon arrival she tied me up in a small spare room with a pair of her dirty panties over my head then left me and went out with her girlfriends only returning much later ***** and totally fucked ******* me then to serve her and lick her clean and to more orgasms.

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SISSY CUCKOLD HISTORY 668.
One of the things that looking back I sort of regret growing up as a budding Feminized Sissy Cuckold was after being confronted and ousted by my ****** for wearing her hosiery and then allowing me to wear her used tights was the lack of chastity back then!
This period of my life was well before the internet so there was no access to any sort of chastity device for naughty sissies thus around the house in the tights and the silky nighties and fluffy wedge slippers she had me wear I was always being caught out suffering erections!
So this *********** act in her sheer dirty tights was the font of a never ending barrage of verbal chastisement and *********** as believe me nothing ever good was said about my penis? she had already made her feelings abundantly clear that first time my little penis erected against her nylon clad foot that I was woefully inadequate in that department.
Worse still not only was I in adoration and love with my ****** for who she was, the way she was and how she dressed and made up that I would shamefully get excited seeing her or when I caressed her feet of an evening and what with being in tights and nightie myself caused me to have filthy unaided sissy accidents which were never missed by my ****** and suitable punishment was inflicted upon me.
And the connection was soon imbedded into me that harsh spankings were the consequences of doing dirty vile squirts into my ******s tights!

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SISSY CUCKOLD HISTORY 669.
Both my Cuckoldress wives became overtly experimental when they took on their new lifestyle.
Of course Tania being a Dominatrix already was the wilder of the two women that I had married But Anne had her ways as well.
Both decided to have at times multipul sex partners Anne never exceeded two at once where's Tania had as many as she fancied on any given night and oppertunity.
What was noticable in both Tania and Anne was when they became Cuckoldresses their sexual appetites grew massively and they were always wanting sex
When talking about things with both of them they found that a huge boost to their libido's was the fact that I was suffering as they rubbed my face into their infidelities, had control over my little penis and could heap as much *********** and degradation on me as they pleased.
Both Tania and Anne were in fact kind and loving in the way they dominated me and that made their actions even more terrifiying when it came to chastizement, this reached it's pinacle with Tania who was a dab hand at flipping on a coin from sweet to volcanic and she had this way about her that convienced me that everything was my fault because I was a Feminized sissy cuckold even if she had done something wrong?? work that out if you can.

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SISSY CUCKOLD HISTORY 670.
One thing all Feminized sissy cuckolds will have to face is the backlash from the Cuckoldress wife over the time in her life wasted entertaining you to sex!
Sissy Cuckolds soon come to understand that all that effort and care they put into sexual intercourse was a total waste of time as your bluntly told your crap in bed, have a tiny penis and she was always faking it!
What now is coming your way as you become her Feminized Sissy Cuckold is little penis and small ball *******!
And it takes many forms and is ****** as what you have between your legs is an offence not only to your wife but also femininity as a whole!
From slapping your junk to kicking, sticking needles in you, burning you with the tip of cigarettes or other lit flames like having your penis wrapped in baking foil and a flame wafted under it making you scream for mercy (which never appears)
Of course many Cuckoldresses go on to want castration or penectomy for their Feminized Sissy Cuckolds and of course that is their right to insist the sissy cuckold complies!

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SISSY CUCKOLD HISTORY 671.
Women just love finding out they are dealing with a Feminized sissy cuckold husband not just some tranny out shopping with a lady that is ok with going out shopping with one of them.
Of course it's usually the wife who loudly and proudly states that the pretty little thing is actually her husband and they are out shopping for some things for him and more importantly things for her to wear for her up coming date with a boyfriend!
When that statement comes from your wife's lips you can clearly see the bitch fight between the shop associates to be the one serving the sexy elegant lady and her sissy cuckold husband.
Be ready for heaps of *********** as your wife and the associate go into minute detail over what would be sex and appropriate for your wife to wear for her lover and also your going to have to stand there and see your wife try things on and ask your opinion on what is sassy and sexy enough to really get her man hard?
The associate will of course chip in with her two peneth worth of verbal *********** and by the time you carry your wife's shopping bags from the store dutifully behind her hearing the sniggers from the gathered staff you'll feel less than an inch tall and fearing the next shop you are heading to!

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SISSY CUCKOLD HISTORY 672.
It amazes me as a Feminized Sissy Cuckold that after all the years I was married to Cuckoldress wives and the other relationships I have had and the firm control of my ****** in days gone by that now I am a dumped and divorced sissy cuckold and I love alone I am still terrified about being caught out masturbating!
It has been drummed into me all my life that my penis is tiny, worthless, pathetic and more of a clit so much over the years that even just touching it fills me with shame and I know I am doing something extremely bad and naughty if it gets hard and I fiddle with it!
Thus even being single I spend time in chastity with various of the women I know keyholding , and as I have heard many other feminized sissy cuckolds say in time you actually feel safe locked in a chastity device.
The fear of touching your pathetic little penis is also a motivator to obtaining sexual relief via being even more girlie and fucking your sissy pussy to obtain the sissygasm thus relieving you of the shame of masturbating like a man would something you know you are defiantly not!