Sissy Cuckold Thought's, experiences and observations!

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SISSY CUCKOLD HISTORY 423.
Can you remember the first time you actually saw a woman being fucked or your wife taking her pleasure with some stud?
Pam Alford the first woman I ever saw taking a fucking on her hands and stocking clad knees the man ramming hard away behind her in doggy style was a beautiful moment.
To see secretly Pam's large tits swinging freely with each jerk of the mans hips loading her with cock and the look of utter sexual bliss on her face followed by the heart stopping look her eyes had when she opened them and caught sight of me looking at her through the partially open bedroom door and the lovely smile that crossed her lips as she moaned in delight chasing her climax.
I knew then and there that with my little penis I would never be able to bring that sort of pleasure to any woman no matter how hard I tried with my insignificant manhood.
The culmination of this is being married to a woman or in my case the two women I fell deeply in love with who both went on to be Cuckoldress wives.
It is by then the real suffering starts as a feminized sissy cuckold because you by then know what you are and have confessed or been caught out by your wife doing the crossdressing and have been ****** to tell her what it is you really are!
Then the moment comes for me after a period of uneasy living with my first wife until via her work she met a man she fancied and agreed to a date.
For me when she told me she was going on a date and it was mid week during the day to his house that for me was the start of the sex! every fevered moment till the time I was collapsed on our bed watching her get ready to go out putting on the sheer white lingerie and seamed white stockings she had decided on with strappy white high heels and white wrap round short dress.
She said later that she had been waiting for me to beg her not to go but could see in my face through all the pain and anguish a sexuality that nothing would stop and so she left the house understanding that deep down although I was suffering what she was doing and wanted to do by them was what I really needed.
Of course as soon as she had gone I got dressed and made up and was in a fog of utter excitement, shame, angst almost sick with sexual feelings the likes of I had never known and every tug of my stockings on my suspender straps and the caress of my sheer black nylon panties threatened to cause me to have a terrible sissygasm that I fought against for the whole seven mind crushing debilitating hours Anne was out on her date.
When Anne arrived home I was once again laying on the bed in a state of nervous collapse my little penis so hard and leaking and Anne came and sat next to me on the side of the bed when she came in to the room.
At once I was enveloped with her perfumes and the stench of sex that made me groan and more so when Anne reached out and held my tiny erection between her thumb and forefinger and gently wanked me as she started to tell me what she had been up to?
I did not last long only up to the part where Robin had lifted her up and impaled Anne on his large cock after she had sucked him off like a slut and I wailed and gout after gout of my worthless watery sissy milk went all over the place that first violent true sissy cuckold sissygasm at the fingers of my Cuckoldress wife not exhausting me as not for one second did it soften as Anne continued with her recounting of her day and mounted the bed and lowered her fucked slimy sex stinking pussy down onto my mouth making me lick her clean deeply before shocking me senseless as she wiggled forward and set me to cleaning her anus out of Robin's sperm as she had taken him there as well.

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SISSY CUCKOLD HISTORY 424.
When my second wife and Cuckoldress Tania the dominatrix decided to become an escort as well she was helped with the initial set up ,the photoshoot, website etc by a lady friend called Paris another dusky half caste beauty.
As a introduction into the escort world Tania decided that for a week she would go up and work in Paris's brothel in the city up from our town.
As you can imagine now as Tania's chastity locked feminized sissy cuckold maid I was driven into a frenzy with the news of this and had the honour of driving her up to the brothel every morning and picking her up late at night.
What I was told by my Cuckoldress about what she got up to during her time there was shattering as we are not taking about one or two punters we are talking about minimum of twenty a day and over forty on Friday and Saturday.
And it was everything from blow jobs, anal sex, intercourse to gangbangs all related to me in insightful juicy detail that had me in a sissy cuckold frenzy.
Even when the week was up and Tania was working from home she often helped Paris out at sex parties a couple of which I attended as well working as the French maid!

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SISSY CUCKOLD HISTORY 425.
It comes to something when as a Feminized sissy cuckold you actually get turned down by a Prostitute because you have such a tiny penis!
This happened to me quite a few years ago and to pile on the *********** the lady in question after ridiculing my sissy clit informed me that she would let me kiss her feet and lick her pussy and anus but it would cost me double!
Yes you heard right DOUBLE! and pathetic me there in her bedroom I coughed up the dough as what she was putting me through although humiliating to the extreme was also highly exciting.
Amazing when you think about it? as a paying feminized sissy cuckold one would think you could request what you want of the lady of the night within reason and fucking pussy would be on top of that list even if she filed her nails while you humped away not even feeling you inside her and because your a feminized sissy cuckold she is reasonably assured that you won't be banging away at her for the hour in fact she would be confident that it will be all over in no more than ten minutes quicker if she can be bothered to use a few salacious words as you do your pathetic attempt at intercourse.
But it seems that even though they are prostitutes they are also women and have standards when it comes to punters and the feminized sissy cuckold is in danger of being rejected.
Many of the Prostitutes I have spoken to get off on the wicked fact that they can make a feminized sissy cuckold go down on their pussies and rectums knowing that these well fucked holes are getting a delightful tongue bath and even a proper creampie cleaning if they have done a bareback regular prior to the sissy cuckold coming in for a session.

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SISSY CUCKOLD HISTORY 426.
It's a good job that Cuckoldresses know that the feminized sissy cuckold needs chastity!
Just looking at myself I was from the day I discovered that my tiny thing got hard and it felt nice when stuff dribbled out of it I was a chronic masturbator
Believe me I was at it all the time so much so at times I thought my penis was going to drop off so swollen and aching to touch it became.
And like I suppose lots of sissy cuckolds I used everything to stimulate my sissy squirt, dirty panties, hosiery, just about anything that would go into my sissy pussy, I even fucked cold rice pudding, used a vacuum cleaner, you name it I stuck my little penis in it.
Now when I think about it I understand the feeling of shame I had when I was doing these *********** things specially soiling superior women's delicates.
So when chastity came into my life there was as a feminized sissy cuckold an acceptance, understanding and a feeling of safety already in me as the lock clicked shut.

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SISSY CUCKOLD HISTORY 427.
One thing I know for absolute certain is that although as a Feminized sissy cuckold I strive for perfection everyday by our very natures that goal is never going to happen.
Once you take on that basic tenant in life it makes it much easier for you to accept the spanking's, the lash, the whip, the crop and the beatings that the Cuckoldress is fully in her rights to dish out due to some stupid thing you've done that has displeased her!
Also accept that she can do them things just because she wants to if she is feeling nettled by something or another?
Tania my second ex wife and Cuckoldress was very much in this camp with her sadistic leanings and she even went so far as to give me reason's for what ever she was dishing out like "Your breathing the wrong way!" and over time getting me trained mentally to accept that everything was my fault even if I was no where near the happing or incident at the time? (work that one out?)
Now you'll being to understand why so many Cuckoldresses seem to have a stash or even up to a dungeon full of gear more suited to a Dominatrix! this in my opinion is because when a woman becomes a Cuckoldress it seems to trigger off an in built need to punish her Feminized Sissy Cuckold husband or partner.
Maybe the basis of this need is how offended she is now about the wasted years the husband tried to man it up before breaking down and confessing about his true nature or she caught him out? how she had to endure crap sex with his inferior manhood for so long?
The list of why's a Cuckoldress ends up weaving her status with that of a Dominatrix is literally endless and as Feminized Sissy Cuckold who now has utterly no human rights you have to embrace this aspect of the one you worship and adore.

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SISSY CUCKOLD HISTORY 428.
As a Feminized sissy cuckold I have to confess that on top of being an addicted creampie cleaner both pussy and anal varieties I also over the years have become under the sway of smelly dirty pussy and anus.
I think you know full well when your out and about the type of women I am talking about that you know will be less than hygienic down below and believe me if you have the sissy cuckold balls you can get a lot of success in this area as these women can hardly believe you'd be willing to go down on them and want the proof!
Over the years I have met woman that have been in appalling states of unhygienic filth.
As a Feminized sissy cuckold I cannot help myself and have gone down on woman that by rights should have had toxic waste stamped on their pubis or buttocks and have had to swallow down bile as my whole being has fought not to be sick over what I can smell, see and then taste!
Shamefully I have licked clean women with UTI infection's, chronic diarrhoea and other inflictions that have made the woman reek.
Once done the feeling of pride I have is immense knowing that I am the sissy cuckold that will clean up anything as a woman has the rights to expect from us.

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SISSY CUCKOLD HISTORY 429.
Watching your wife have sex with another man is of course the pinnacle of being a feminized sissy cuckold but to make the experience totally electric one if lucky also see's the seduction of the guy or his seduction of your wife.
It humbling and lovely to see your wife when she gets that look of want on her face and the change in her body manner when she comes in contact with a guy who she likes and is obviously flirting with her.
Because you know her so well you see these signs and know your going to be cuckolded yet again and the fact she knows she can do it in front of you it empowers her even more making it even more exciting for her.
Of course if the man your wife is attracting is cool and confidant when he finds out that your a feminized sissy cuckold he will step up to the plate and show his masculine dominance over you as he and your wife start a highly sexual relationship.
With a man like this pleasuring your wife you as a feminized sissy cuckold can do nothing but serve and worship both of them helping in anyway possible to mask their time together as perfect as possible.

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SISSY CUCKOLD HISTORY 430.
It's shameful for the Feminized sissy cuckold when the day arrives that it can no longer get an erection and go through the stage of premature ejaculation.
And believe me it comes to all of us through denial, chastity, penis punishment and the strap on cock or real dick.
I of course have also had some medical issues that have not helped leaving me totally unable to get hard unless my sissy pussy is filled and fucked the sissy gland being my avenue to hardness.
This constant state of floppiness is shamefully pathetic because inside there is no reduction in the sick sexual urges I feel all the time! urges that should have me rampantly hard.
Tania used to laugh her stocking off offering me sexual intercourse her legs open playing with her wet pussy and I would be kneeling there in front of her unable to get hard while my mind was slavering until she would say "It's a good job I got fucked earlier and filled with spunk with you not capable! now get licking I need to cum!"
As you can imagine that sort of thing is emotionally damaging to the feminized sissy cuckold and although nasty and hurtful we also crave these intimate moments with our Cuckoldresses.

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SISSY CUCKOLD HISTORY 431.
With the hot weather at present it will be driving us feminized sissy cuckolds to distraction over the thought of so many hot sweaty dirty feet out there of the goddess female that needs our mouths and tongues kissing,licking and sucking away the days aches and pains
The thought of sweaty soaked hosiery coming out of high heels for worship has me all in a tizzy of sissy cuckold desire.
At this time of the year I do not even mind seeing bare feet in strappy high heels with beautifully painted toe nails.
I am sure when I am out that plenty of ladies who see me the sissy in a frock know that I am looking at their feet and get a thrill out of it as many a time I have been having a coffee in a cafe and some lady has been wiggling her toes a bit more than you would do if no one was looking.
Even worse many a time they catch you looking and give you that knowing grin that's says they have spotted a weak and pathetic feminized sissy cuckold.

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SISSY CUCKOLD HISTORY 432.
There must be something in the water in the City of Leeds as today I am going to have a day with a lady Called Susan who is utterly kinky dishing up the putrid smelly pussy and ass that so captivates me.
Leeds was also the place where I met Tina that lady I served after being dumped and divorced by my second ex wife and cuckoldress Tania.
Tina as my readers will know was huge lady in her sixties who was utterly unhygienic had stoma bags and suffered from Manila Yeast infection, she even had a pig like perverted face although in a strange way with make up there was something strangely sexy about her
What I do know is that Tina should have come with a warning that she was toxic waste site as that first time I knelt in front of her as she splayed out on the bed and eased her huge knickers down the mess from her red raw dripping cunt was like a punch in the face.
Manila yeast infection smells like a dirty trash can of dead fish left in the blazing sun for a week and this grey cottage cheese like discharge dribbles out constantly.
Only my weak pathetic feminized sissy cuckold personality had me terrified of Tina and had me get my face to her pussy and lick her swallowing down the awful mess and when Tina heard that my body was starting to reject the vile filth from her she took my head in her hands and held me tight to her pussy making me continue licking her clean as I vomited into her pussy and only after she had massively orgasamed did she allow me to pull away.
Unlike any sane person I did not flee from her house but stayed with her in a state of trauma as things got worse as soon Tina removed her stoma bags and had me sucking on the artery's that protruded from her lower gut cackling like a hag when a torrent of her filth filled my mouth and I swallowed it all down.
This episode with Tine stands as one of the top five most perverted things I have ever done and it was not just a one time affair as I visited Tina often after that and she foisted every sick need she had on me.

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SISSY CUCKOLD HISTORY 433.
Over the years as a Feminized sissy cuckold I have been interfered with by many a dirty old pervert.
This sort of thing truly horrifies me to this day because of the sexual ***** I suffered at the hands of my Step ******.
A not very nice episode in my life as I was developing as an already secret crossdresser with some strange idea's about sex in general.
Bill the Step ****** took it on himself to ***** his cock into my mouth and fuck my throat till he ejaculated in me balls deep that afterwards had me spewing up.
Then as the weeks went by not only through threats he got his cock sucked more he went on to bugger me slaking his lust in my anus which was very painful at first.
To my eternal shame and self disgust even to this day as Bill screwed me because that's what it was I got a little erection and climaxed myself not the first cum I ever had but one of the very early ones.
Of course this led to me being very anti homosexuality but here was the problem? as a developing Feminized Sissy Cuckold want to be (even if I did not know these words back then) the thorny issue of queerness kept rising it's ugly head.
The question was simple to me? how could I claim to be straight if what was turning me on was dressing up as a woman and dreaming of licking a woman clean after she had been fucked! and I also found myself when dressed up experimenting with inserting things inside of me!
Then came my second incident with a male when dressed as Carla I slipped into a porno movie theatre in Soho and in the dark I had eased my skirt up and was fiddling with myself watching the sex on screen when suddenly a guy sat down on the chair next to me and reached out knocking my hand away and taking over masturbating me.
I was scared stiff and terrified and was like a stone statue but the effect of the dirty movie and his hand defeated me and I moaned through gritted teeth as my sissygasm shot out all over the place leaving me a shuddering mess.
Soon after the squirt ended I was up and fled from the cinema utterly ashamed and full of self disgust over what had happened.
Then there was the ex step ****** Bill part two when I was out shopping one day and I literally ran into him in a store and through my horrified reaction he realized who I was.
By then I was dressing nearly all the time I was eighteen or nineteen and in a very submissive place in life already having experienced some solid sissy cuckold stuff via Pam, Fran and Wendy and even a couple of prostitutes.
I was still in the early days of being out in public so not to make a fuss I allowed Bill to lead me away with him and ended up in his car and being driven back to his house.
Now I have to admit Bill this time was different not so pushy and demanding but he was still what one would call masterful in a courteous way and he wanted to fuck and I was in no position to say no.
I still felt disgusted with myself as I submitted to him even more so as he acted like a teacher this time making me get into all sorts of positions to be fucked or to suck him off and this went on for the entire weekend.
It was not until I was married to Tania my second Cuckoldress wife and dominatrix that I became lets say more at ease with the occasional interference by men and the reason for this was that the decision was taken away from me and I was ordered by her under threat of punishment as her feminized sissy cuckold to engage in homosexual acts for her entertainment or money.
Of course Tania knew all about the ***** I had gone through and how I felt about it all but that just delighted her to be able to make me wallow in torment as I did sick gay stuff under her guidance and orders and to this day I can remember clearly Tania beating it into me that even though I might not like what was happening I had to as her feminized sissy cuckold look like and act like a cock slavering slut.
Now a dumped and divorced feminized sissy cuckold I still do the queer stuff for various reasons, one Tania when talking to me will often say sissy Carla you need some cock and will expect the next time I talk to her an account of what situations I have been in, then there is me as a feminized sissy cuckold with shame and disgust mixed in with sexual excitement I at times put myself into situations that horrify me.
The worst of this was via a dirty old man I know called Reginald who *****s me once in a while, he is seventy now but still active and he conspired to get me to attend a party he and some of his pervert mates had one summer evening and I ended up sucking and being fucked by all eleven of the dirty bastards leaving me feeling utterly ******** and ashamed as during the cock sucking and ass fucking my little sissy clit had two anal sissygasams.

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SISSY CUCKOLD HISTORY 434.
One thing i noticed with both my ex wives was their insane jealousy when it came to other women looking at me the feminized sissy cuckold and believe me there was never any of the fantasy lending out of the sissy cuckold to their girlfriends.
That's not to say that with both Anne and Tania their friends knew about me or at times invited round to the house to see and even participate in things like me being punished.
But when these moments occurred both Anne and Tania were fully in control of the situation.
Thinking about it these days makes me proud and gives rise of feelings of love and adoration for both of them as they obviously valued me as their Feminized sissy cuckold maid and slave so much that they kept a tight reign on me and what access others could have to me.
In conversations with both Tania and Anne I asked about this observation and both gave the same sort of reply in being that when they had come out with their Cuckoldress lifestyle to their girlfriends there grew a frenzied envy and Both Anne and Tania said that there had been women so called friends who wanted me for their own.

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SISSY CUCKOLD HISTORY 435.
When you were outted as a want to be Feminized Sissy Cuckold was it because you'd been caught out? or did you find just enough balls to confess to your wife how you felt?
I having been married twice have experienced both, with Anne the first Wife she caught me out dressed up masturbating and all hell was let loose.
The aggro got so heated that I did actually think the marriage still in the early days was over, but in the end Anne cooled down and accepted my dressing up needs and so I was able to do it at home.
I think it was Anne herself who pushed things on as one night when she got home from work we were chatting in the kitchen as I was doing some ironing I was made and dressed up at the time in a pair of sheer white stockings, bra, suspender belt, panties and high heels under a filmy white nightie.
That evening Anne seemed to be agitating for some reason and at one point she got round to my dressing up hobby and that she felt left out?
You know when your having a conversation and you can feel something explosive is going to happen at that moment I felt that so thick like smoke in the kitchen and said to her "What did she want to do then that interested her?" and I was stunned by her reply "Sex!"
I was in a state of shock because the way things were said Anne was not referring to sex with me!
This was the point I gathered up all my nerve what little I had standing there in front of my wife all sissied up and stammered out "I could understand that and would not stand in her way if she had boyfriends!"
I think at that moment I was expecting another tirade of anger and shattering of our marriage but the opposite was what happened and Anne smiled and said what I had just said was very kind and thoughtful and she would think it over?
I think things were already at the point of Anne taking a lover because mid the following week she announced that she had met someone and was going on a date with them.
Now Tania was a whole different kettle of fish as she knew I was a crossdresser before we even started seeing each other and from then on things just escalated, Tania because of how she looked and comported herself as a woman attracted men like bee's round a honey pot so from day one the dire need to be a feminized sissy cuckold was uncontrollable in me.
Then Tania started to work the chatline so I was hearing her being so sexual all the time, after a while it was Tania herself who informed me that she wanted to become a Professional Dominatrix something we were able to put into action when we moved into our new home.
I was by now writing short stories for her to telephone record and a lot of them were on the sissy cuckold subject and she sort of picked up on this and when we were having sex she would tease me about my small penis and fantasy chat about fucking real men!
Of course Tania could not help but see how super turned on I was over this sort of talk and in the end we had a long chat about everything whilst out walking the dog in the park one day where I begged her to lock me up in chastity and because I was useless to her in bed that I wanted her to have lovers!
There was no resistance to this what so ever from Tania and in short order I was locked in chastity and then she went out on a date with one of her old flames and so her being a Cuckoldress began.
Crazy time was when one evening Tania picked me up from work and she said she had something she wanted to tell me so she pulled into this layby and I was stunned when she got me to ease my trousers down and she took off the cage to the chastity device I was in freeing my little penis which erected straight away.
Tania then told me that she had released me because she did not want the locking up fetish to get in the way of what she was going to tell me?
Promptly Tania now told me that she had decided on top of her work as a Dominatrix to also become a prostitute!
I was stunned and so was Tania because as her words hit me my little penis just exploded shooting my nasty sissy milk all over the interior of the car.
In the end Tania laughed at the sight and said "Well I got my answer as to whether you want me to be a prostitute or not!"

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SISSY CUCKOLD HISTORY 436.
Once I found out that certain monthly publication included stories about Cuckolding I became an avid collector of Magazine's like Fiesta, Penthouse, Escort, Miss Sadie Stern and so on and I had mountains of them and felt deflated if a issue did not have a letter or two on the subject.
The best was the periodical release of the Fiesta or Forum letter collections!
For the lone alone budding feminized sissy cuckold there was nothing better than an evening alone all dressed up with something to stick up your sissy pussy and read and wank yourself to pleasurable oblivion.
Of course progress has seen the end of these delicious publications but the advent of the internet has given us every aspect of Cuckolding we could possible want and I think with the open availability these days many more people are coming out of hiding with their desires making the Cuckoldress led relationship much more desired and normal for both women and the budding feminized sissy cuckold.
Even the Bulls (I hate that term for the guys) are so much more learnered and switched on about the subject and their role with the Cuckoldress wife and Feminized Sissy Cuckold making the experience so much more electric for all concerned

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SISSY CUCKOLD HISTORY 437.
It's strange being a Feminized Sissy Cuckold as one of the main urges for the sissy cuckold is the desire to have a sissy squirt but the rub is that the feminized sissy cuckold loves that feeling of denied sexual frustration that leaves it in a tizzy all the time.
And that feeling of swimming in a sea of never ending perversity is one of the main parts of the feminized sissy cuckold life and many a Cuckoldress wife recognises this thus in comes the chastity device and the switch over to anal prostrate milking so as to lessen as much as possible any relief the feminized sissy cuckold gets via the draining.
The knowledgeable Cuckoldress will also comport herself and change her lifestyle to make her feminized sissy cuckold live in a world of feminine beauty and overt sexuality so basically Sissy Cuckold will live with never ending stimuli and little tricks at night restraining Sissy Cuckold making him ***** with soiled panties over his head or more extreme with a piss gag on attached to a piss tube attached to sissy cuckolds little clit so urine is recycled all night.
All of these sort of things will have the Feminized sissy cuckold in a frenzy all the time and I would dare to say with my experiences of this that when it comes to a milking sissy cuckolds can get to a state that they actually feel disgusted with themselves if they are made to squirt.

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SISSY CUCKOLD HISTORY 438.
There are many up sides in being outted as a Feminized Sissy Cuckold to all and everyone instead of living in the shadows.
Take birthday's and Christmas for me a delightful surprise came as I started to get two lots of presents from my ****** and a couple of my Aunts.
I would get the usual hum drum male present of aftershave or such like but now I also received girlie things like hosiery and lingerie specially panties.
And believe me when everything is out and known and that there is an acceptance of what you are it's thrilling to know that a very important (maybe the vital part of you in acknowledged)
One thing I have noticed is that over the years the male presents have really dropped of something I am not to worried about as friends and family seem to forget that I was born a male!
Maybe they just refer to me as the sissy cuckold or faggot when my name comes up in conversation?
I do not get to hear obviously their inner thoughts and what they gossip about it might be all demeaning stuff but as a feminized sissy cuckold I have to accept that I will always be regarded as freakish to most vanilla people.
The male members of the family are the most openly spiteful towards me and in jocular ways they call me the shirt lifter or bum boy to my face where's the women are much more sly and teasing when they get me to talk setting me up for ridicule and in many ways I believe they rather like the thought of being Cuckoldresses themselves.
Now I do not advocate that you should jump in and out yourself as it could lead to out and out disaster but if fate has it in store for you exposure then you have to cope with it with a smile on your lips.

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SISSY CUCKOLD HISTORY 439.
The crazy risk's I am sure you like me took when we were growing up getting into a sexuality that none of us at the time understood? before suddenly finding one day through a myriad of sources that we were to be classic Feminized Sissy Cuckolds.
Up to that point I know all of us thought we were freaks in a lonely world and that no one would understand us or our needs.
Can you recall the sheer terror you felt over even the mere thought of being caught out and having to explain yourself?
But the pull in you was so strong and could not be denied that maybe you like me would steal and filch women's hosiery and panties from their dirty laundry baskets to not only wear but also to sniff on and masturbate with.
Then the close shaves when you had dressed up and someone came home early and you only just managed to get out of the things you were in and tried to act normal as your heart hammered away and guilt was written all over your face.
In the long run getting caught out as bad and terror filling as it was, was really a release of tension when you came to understand that the woman or women you had to confess to over the years did not explode like Mount Etna but in many cases were sympathetic to your plight!
The one thing all budding Feminized Sissy Cuckolds should never do and I wish it was common knowledge is when you have to confess do not in any way shape or form lie as that is what really makes the **** hit the fan!

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SISSY CUCKOLD HISTORY 440.
Thinking back to the time I was married to my second wife the Cuckoldress/Dominatrix and Escort Tania some of the most humiliating but thrilling times was the little jobs that are expected of the feminized Sissy Cuckold maid.
I always found it extra humbling having to drive Tania to her outcall jobs to Hotels or the clients home with me having to drop her off and then wait for her to return after and hour or so knowing as I obediently sat there that she was in some room in the building being fucked by another man.
Of course there was not danger that I would sit there with an erection as my silly little clit was locked in chastity and hidden in my silky frilly panties under my dress or skirt.
It was tormenting sitting there as of course the car was filled with Tania's perfume cloying scent and if the punter was a regular she knew teasingly she would as she alighted from the car open her handbag and dump the condom box on the passenger seat so I knew that she was up there doing bareback sex.
And do not think for one minute that the angst eased off when she tottered on high heels back to the car looking like a ravaged slut that the drive home got easier because it did not as the car now filled with the stench of a fucked woman that made me sissy cuckold giddy and Tania relished relating to me as we headed home all the filthy gory details of what she had done with the man so by the time we got indoors I was literally begging to do creampie clean ups!

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SISSY CUCKOLD HISTORY 441.
Practice makes perfect as the old saying goes and for the budding feminized sissy cuckold nothing is more true!
Like I once was when time allowed I started to experiment with make up when I was dressing up in my ******* hosiery, lingerie, heels and dresses and like all of us it was a rocky start ending up looking more like Coco the clown.
But inside each time I made up there was that need to do better and I realized that one of the essential things to do was to watch females applying their war paint and to also source my own cosmetics.
Once these two things were done things started to improve and by the time I got my first own place to live and was able to do my face up many times daily I was looking more and more feminine as the days passed.
So it really does come down to practice to get it to the best you can possibly get! also for budding sissy cuckolds all the hair needs to go from your body and legs, your not a man your a sissy cuckold and have no right to masculine tufts so get it gone and keep it gone.
For the standard small dicked feminized sissy cuckold nothing says Pathetic and worthless that a shaven smooth little penis and testicles no hairs show off just how truly small you are and will make women laugh when ever they see it!

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SISSY CUCKOLD HISTORY 442.
Although I personally never wanted kids I read at times about couples into the Cuckoldress led lifestyle who do and it interests me about this step a couple can take!
I truly hope that it's just not the kink that makes them take the step of getting impregnated by the black lover but more of a natural progression of a superior male and the wife doing a loving thing.
Of course it maybe a shock to the feminized sissy cuckold husband or maybe not if this is all a planned parenthood step.
It must also be delightful if none of the families know or the medical staff and when the baby is born and it's black the truth comes out!
The squirm factor for the feminized sissy cuckold husband would be horrendous specially if the wife makes him for the first time come out to his family as a feminized sissy prior to the birth.
Realistically looking around society these days there seems to be many coffee coloured kids who are with white parents so this sort of Cuckoldress led marriage must be on the rise.

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SISSY CUCKOLD HISTORY 444.
As a Feminized Sissy Cuckold I have lost count of the times when out shopping and have gone into some Emporium or other type of outlet selling female Lingerie or Hosiery and have literally witnessed the Proprietor rubbing her hands together at my entrance!
These days Feminized Sissy Cuckolds, transvestites, drag queens etc are doted on and for good reason!
All these ladies who own shops such as these learn early on that us feminized beings out there stop at nothing when spending on the things we want and these propreteresses love us for it.
I have spoken to many as I have been shopping and all of them say we spend far more than your average woman specially on things like Hosiery, it seems us dressers just cannot get enough nylon in our lives.
Even looking back to when I first started buying hosiery at a place called Tight Spot in Lincoln many years ago the lady owner who gave me a gratis suspender belt to go with my first pair of Stockings after measuring me up for leg size knew what she was doing and captivated my tights and stocking purchases for many years.
In fact I recall never being able to go into town without stopping off at her place and buying something.
These days there is no need to worry about hitting the shops for any female item you want as retailers know where their bread is buttered! but I admit that as much as it's nice just to be accepted I used to love the weight of being sussed out, shamed and even humiliated at times when out buying.

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SISSY CUCKOLD HISTORY 445.
One of the things you quickly grow to accept and then become addicted to as a feminized sissy cuckold is the taste and tang of urine!
Specially if your initiation into sexual contact with women has come from the hands of a mature lady.
As is well known the older a woman gets the more issues she has with leakage of the bladder and with variations of what she is wearing and weather she can become very pungent!
Of course women over the years have rushed to wash and freshen up all the time hoping to be sweet smelling and tasting but over the long term unless she is with a real man its all to much bother if she just wants a sexual explosion.
Women are not stupid and learn early on that there are species of humanity out there that will go down no matter how smelly and dirty they are.
And this is one aspect of what attracts Ladies to the Feminized Sissy Cuckold!
From the Cuckoldresses that I have spoken to over the years they all told me that it's so refreshing to be in a position to be able to open their legs anytime they please and have the sissy cuckold service them with their tongues.
Most get a erotic thrill in having another lick what they certainly would not because of the state it's in and the climax is all the more intense watching sissy cuckold get munching.
Of course it's does not stop there as now they know they have someone who will do what they are told they feel the devil in them and will relax and dribble pee into the sissy cuckolds mouth as its licking and once there its just a short step to just openly pissing in sissy cuckolds mouth and making it ***** it all.
From that moment the Cuckoldress will start looking upon her sissy cuckold as her toilet and all to soon she will say to herself "If sissy Cuckold can take what's from my bladder as a toilet there is no reason why sissy cuckold cannot take what comes from my bowels!"

SISSY CUCKOLD HISTORY 446.
All my life firstly as an unknowing and then an aware Feminized Sissy Cuckold I have suffered in my opinion with the lack of intercourse sex with women!
Of course having been married twice I did have sex but very soon into each marriage that was stopped once the good lady wives got over the novelty!
As for other women there have been one or two but only one time basis as I think they must have felt it was to late to say no or they did not have the guts to laugh at my miniscule size, for sure neither got off on my pathetic efforts and it was only by mouth they got off.
So is there any wonder feminized Sissy Cuckolds slide quickly into any and all sorts of deviant sex with many even though they are not in anyway homosexual slipping into that area just to have some sort of close sexual contact.
And thus comes the reason the Cuckoldress wife needs to have strict control over the feminized sissy cuckolds needs and desires, it should always be the Cuckoldress that decides what if any sex her sissy cuckold gets and a Cuckoldress with her head screwed on right will always opt for relief for the sissy cuckold which is least liked or terrified of!

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SISSY CUCKOLD HISTORY 447.
Was just thinking back to a lady of the night I dated for a good while after I was dumped and divorced the second time, she was really into transvestites so after the first session I went to her for we started dating, we met in a department store when she spotted me purchasing some hosiery and we got chatting and she gave me a card.
Anyway soon after we started dating I was called up to her apartment and she had a guy there a friend of hers and things went on from there.
Lucy liked watching homosexual sex and under her commands this guy had me sucking his cock and then rimming him before he fucked me in the ass under the delighted gaze of Lucy.
After the guy had showered from screwing me he got into the action with Lucy and when she was riding her ass up and down his meaty cock she had me on her clit and when she hit orgasm she squirted massively making me ***** her all down as she shuddered in pleasure.

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SISSY CUCKOLD HISTORY 448.
The many ways a Cuckoldress wife can humiliate but also thrill her feminized sissy cuckold.
Back when I was married to my second wife the Cuckoldress, Dominatrix and Escort Tania we would as a married couple go out for lunch or Dinner at times.
Of course by then I was pretty much living as a femmed up sissy cuckold all the time.
Anyway first time this happened at a lunch time in this gastro pub we were shown to a table and the waitress took our food and ****** order.
When the ****** came we sat chatting as you do and of course we were being noticed not just for Tania's stunning beauty and sexy mode of dress but also folk could see that under all the make up and pretty skirt and blouse I was a transvestite.
To my surprise Tania then got up and took my glass of soda water and vanished not to return for about five minutes when she did come into view again from the Ladies restroom she was followed out by a gaggle of women who were all looking over at me as Tania came to the table.
In her hand was my glass and it was now filled with what could only be her urine which she placed in front of me and I squirmed in *********** as I knew then the looks I was getting from the looking women was because Tania must have told them it was a glass of piss for her feminized sissy cuckold husband.
And so I raised the glass to my lips and took a large mouthful of Tania's hot salty urine right there in the dinning area with knowing eyes mirthfully looking at me an act that humiliated me and thrilled me at the same time.

evilwife
3#3. That's a beautiful pussy. May be the best I've seen on the net. It must taste delicious!
D

Thank you for your comment bobbye

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SISSY CUCKOLD HISTORY 449.
Of the few times my second ex wife and Cuckoldress actually brought me off by her own hand the experience way uncomfortable to say the least?
Tied down on a bench in her dungeon she hooked my frilly panties under my sissy ovaries and caressed my little clit to hardness.
I then watched her don a pair of latex gloves and take up a Chilli which she split open and spat into so it was all juicy.
Tania then held my little clit and proceeded to rub the chilli all over the dome till I was coated in sap from the fruit.
Next step was to place me in one of the extra small condoms she brought for me and then start to jerk me off.
Already the chilli sap was burning and I am whimpering and moaning as the pain overtook any pleasure I was getting from her hand.
The fire just got worse and worse but there was nothing I could do and the impending sissygasm was coming as it felt like my sissy ovaries were turning to stone.
I was actually sobbing in pain when I squirted into the condom with the searing heat, Tania then using her thumb and forefinger took her time massaging all my weak watery sissy mess into the dome of my clit which set off the fires of hell ten times worse than it had already been.
She left me to go and have a coffee as my body flexed against the restraints I was bound down with as my sissy penis was burned by the chilli sap driving me insane with agony something that took hours to die away.

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SISSY CUCKOLD HISTORY 450.
It was a humbling experience that day Tania came into the kitchen from her dungeon and told me to follow her, I stopped the housework I was doing and followed.
And suddenly there I was in her domain in my pretty maids dress and there was this guy restrained to the St Andrew's cross.
Tania with riding crop in her hand tapped on the guys rather large erection making him groan and spoke in a kind loving voice.
"This slave has paid to have a blow job! unfortunately for him he did not ask for a specific person to do the sucking so here you are sissy cuckold squat down in front of him and take his cock into your mouth!"
Of course I obeyed as the crop could all to easily be turned on me as it had been many times before!
This was the first time Tania by her command had me perform a homosexual act in front of her and she gleefully watched knowing what fears and terrors I have about contact with men.
With mouth full of cock I listened to Tania instruct me how she wanted me to suck this guy off as she teased him playing with his nipples at times caressing him and then inflicting pain.
When the guys started to lose it Tania then took my head in her hands and ****** my mouth onto every inch of the cock so his balls were on my chin and I was gagging as he shot his load all the way down my throat.
Afterwards Tania threw me aside ordering me back to the kitchen and my tasks as I struggled to compose myself!

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SISSY CUCKOLD HISTORY 451.
One thing I know for sure being a Feminized Sissy Cuckold is that when your good lady wife or other significant woman in your life knows about you and controls and dominates you a deluge of things will happen to you?
One of the main things women like doing is fucking the feminized sissy cuckold and in doing this they let their inhibitions totally vanish and their main aim is got get the biggest of phallic objects up the sissy cuckold ass!
Tania my second wife and Cuckoldress would go into heavy duty fetish shops when we were shopping and literally become transfixed on the largest most evil strap on cocks that were on display and of course I would have to purchase them for her.
Not that she started straight away on the big stuff, it was sort of gradual if you could call it that with ever increasing sized of butt plugs and hand held dildo's until the strap on's went on and whether I liked it or not the lubrication was applied and the strap on cock was ****** all the way in and her idea of screwing commenced (unusually ****** anal assault)
Sometimes after one of her sessions I could hardly walk she had fucked me so hard and for days my puckered little sissy pussy would throb from the battering it had taken.
And of course there came the different types of lubrication from the normal stuff to tiger balm that had me screaming in agony and crying as I was deeply shafted.
And there was no escape as Tania would ensure I was bound down on a whipping bench or other piece of bondage furniture.

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SISSY CUCKOLD HISTORY 452.
Any one who has become a feminized sissy cuckold will tell you that once you've had that hands free sissy squirt while watching your Cuckoldress wife fuck with another man you are lost for all time and there is no way back for you to any sort of normality!
I read some place years ago that the sissy squirt seeing another man fuck your wife is called sperm competition? your body is trying to show your wife that your still worth something? well do not worry your pretty little feminized sissy cuckold head your wife will love seeing you abase yourself in front of her and her lover.
The intensity of the sissy squirt in front of your rutting wife will be the most draining and powerful in your life! for the sissy Cuckold it's the culmination of years of yearning breeding and shame all coming together in one divine moment as you watch your wife's pussy or other hole get ******** by a cock that your little thing could never compete with in a million years.
And that look on your wife's face as she is totally filled and fucked the man going places in her that you could never ever get near with that thing of yours.
To see your wife orgasm wildly on a real man's cock as she screams for his spunk and pledges herself to anything he wants her to do for him literally shouting the house down that he is so much better than her pathetic husband and she will be his slut from now on!
When she then hears her sissy cuckolds panting humiliated shriek and looks over and sees his tiny penis explode and the weak watery sissy mess shoots out just from watching her get pleasured it gives her a feeling of utter power that she will never want to lose.
And now the sissy cuckold is drained from the massive out pouring of defeat at the hands of a real man and the Cuckoldress wife is shaking in delight her cunt full of his potent cum the sissy cuckold is then ripe for bringing to lick clean her creampie pussy and to suck clean the lovers cock.