SISSY CUCKOLD HISTORY 815.
As a budding Feminized sissy cuckold how many times did you get caught out fiddling with yourself?
For myself it was five times and there was never any abatement of the shame and humiliation in being caught out!
The first through to the fifth times it was my Mother who caught me out the first time I was in a pair of her used tights that she had already started to let me wear at home and I was in my bedroom my little penis all hard erect in the nylon and I was caressing it when she just came through the door catching me fiddling with myself!
On seeing me she jeeringly sort of snorted and snapped “Pathetic!” as my body shook and I filled the front panel of the tights I had on with my little creamy dribble under her gaze.
Afterwards before she left the doorway, she informed me that I was to keep the tights on and suffer my mess for the rest of the day!
Second time again I was naked apart from tights and this time she caught me out looking at a dirty magazine I had got from somewhere I did not do cum, cums this time, but I did later on get a spanking for being a dirty pervert looking at women in nudie books!
Time Number three was in the bathroom in her dirty tights and this time even worse as she caught me out licking and sniffing a pair of her filthy worn panties as I pulled my little clit!
Standing there with me frozen in fear at being caught again and in this manner, she laughed and said, “Don’t let me stop you get it over with!” as she crossed her arms and watched as I rubbed myself off with the taste and aroma flooding me from her dirty gusset and the sight of her nylon coated legs and high heels bringing me off so hard and quickly.
Time four was on another level as I was starting to experiment with make up as well and thinking she was out I was in her bedroom with a pair of her high heels on, testing the waters with a suspender belt and stockings I had found in her drawers and naughtier still I was laying on her bed legs in the air admiring myself with my hand pushing into my bottom a vibrator that I had also discovered in her bedside cabinet.
Thus, in she walks to see me sissygasm with a sex toy in me and my hand rubbing my little clit in a blur of new perversion for me.
Time five I did not even get the luxury of privacy as I was attempting to sneak away to my bedroom for some alone time one evening and it was like she could read my mind and as I tried to make an excuse she cut me off and informed me that if I was going to play with myself like some freak I could think again and just get it over with then and there in the lounge instructing me to hook the band of the tights I had on under my hairless little balls and to wank off into my hand.
This I did as I gazed at her stretched out on the sofa her nylon clad legs and feet addling my pathetic brain making me shudder as she intently watched my masturbation wiggling her red painted nylon clad toes at me and making some very disparaging remarks about how little and puny my penis was until I squealed like a big girls blouse and did the mess in the cup of my spare hand so as not to soil the carpet.
This was the first time I heard the order lick you hand clean! And so, I did as I was utterly fearful of disobeying my mother.

SISSY CUCKOLD HISTORY 814.
The sign of a truly pathetic feminized sissy cuckold is one that’s kneeling or sat next to the bed its wife is on with another man having sex with sissy being all dressed and made up watching avidly.
Of course the Feminized sissy cuckold may or may not be in chastity but it matters not when as it’s watching its wife in utter sexual bliss the man she is dating the one with a truly massive cock eases it into her wet glistening ready pussy and sissy cuckold without even touching itself has a nasty sissy accident and little dribbles of its sissy cream ooze out from the tip of its sissy clit.
Tania my ex-wife and Cuckoldress loved to see this reaction out of me when she was making love to a real man one that could give her the deep hard satisfying sex that I was incapable of giving her saying that the uncontrollable sissy squirt I had watching her get pleasure from a real man was a true sign of my love and adoration of her.

SISSY CUCKOLD HISTORY 813.
Like many Feminized Sissy Cuckolds, I am very poorly endowed with a just under three-inch erect sissy clit! That has never done me or any woman any favors.
Once upon a time in the mists of time it was an uncontrollable scraggy bit of meat and was forever stiff but once my true sexuality started to bloom and more and more females in my life started to humiliate me about its smallness and how worthless it was my male ego started to rapidly crumble.
By the time I was actually cuckolded by my first wife I was having penile disfunction (in my twenties) and chronic premature ejaculation issues and what with the feminization and seeing my wife fuck other men I was in serious deep dark waters.
Over the years along came chastity regimes enforced on my and a never ending cascade of verbal put downs and mostly my little sissy clit stopped getting hard with Tania my second wife working hard to make sure I only achieved sissygasm anally and only ever making me erect if she wanted it to be so which was not something very high on her lists to do as she always stated that a sexually denied feminized sissy cuckold is the most compliant sissy cuckold so mostly my sissygasms were accidents when I could not control myself for many various reasons even though I knew harsh punishment would be the result of me making a dirty sissy mess!
Now as a dumped and divorced feminized sissy cuckold my sissy clit is almost totally a floppy worthless little piece of meat, and I can only have a sissy dribble with lots of anal fucking to hit the sissy love bud just right!

My stars aligned last night. Lois was staying at her clients house for the night and my secret boyfriend told his wife he was away on a course, but he stopped the night with me. I cooked him a nice dinner and then we went to bed and made love and he was still here when I woke up. I'm feeling very loved up today. I would have loved to have woke him with a blow job, but I drained his balls twice last night.

SISSY CUCKOLD HISTORY 812.
It’s always fascinated me as a Feminized sissy cuckold as to how women love to see the sissy cuckold abase itself doing the most humiliating, degrading and disgusting things just because it has received an order.
The woman does not even have to be the cuckoldress wife or a Dominatrix as all women have in them that seed to see a mere so-called male totally servile to the whims of womanhood.
I recall being exposed to one of Tania’s girlfriends once who had come round for a coffee with Tania and was shocked by being served by this well presented French Maid and so the avalanche of questions started to which as always Tania replied to openly exposing me as her husband and what I was and that I was locked in chastity and I did everything I was told to do without question of I would be punished!
Maxine the woman was enchanted and asked to see my chastity device which of course I had to expose to her and Tania not being happy with that also made me show my anal chastity device.
By the time Maxine left she had asked to see Tania punish me and watched while Tania flogged my bottom with a riding crop fifty times. Maxine then still not totally believing I did everything I was told brought back from the bathroom the worn panties she was wearing and had me lick this slime from the gusset that had leaked out of her and also drank from the jug of urine she had filled till it was empty.
Maxine was never going to be a Dom or a Cuckoldress but just because she found herself in a situation where she could make a sissy cuckold do things to amuse her, she was more than game!

SISSY CUCKOLD HISTORY 811.
Queerest thing being a Feminized Sissy Cuckold, fancy feeling the total expression of your sexuality seeing the woman you love and adore in another man’s arms on the cusp of having sex and you know and see that the man your wife has chosen to fuck is everything you are not!
As you watch her seduce this hunk your raging with the green eyed monster of jealousy but you are to meek, spineless and pathetic to do anything about it and over that angst everything in you wants your wife to be fucked by an alpha male as you can hardly be called male as your dressed and made up as a female and you have a minuscule penis that never did your wife any good.
In many cases when the sissy cuckold first see’s a huge cock slide into it wife’s pussy it will have an uncontrollable sissygasm in it’s silky panties even if it’s locked in chastity such is the intensity of the moment and it will be the feminized sissy cuckolds most powerful dribble it’s ever known totally sealing the chains that captivate him to what he is.
Of course the Cuckoldress wife will know and understand all these weaknesses in her Feminized Sissy Cuckold and that is why from starting to get ready for the deed she has involved sissy cuckold in helping her bathe and dress in the most sexiest provocative lingerie, hosiery, Heels and outfit lovingly teasing and tormenting her sissy cuckold so before the date her sissy cuckold is in frenzy of sissy cuckold desire and angst.
And of course The wife will use everything in her feminine arsenal with the man she is going to fuck becoming a hot wild slut doing things she has never done with her husband really letting herself go into the morass of sexual pleasure and in doing this she will in front of her Sissy Cuckold have the most explosive orgasms of her life thus chaining her forever to be a Cuckoldress.

By chance, Mother and I were in a bar in our home town and her friend and husband were in there. I have shared on here that I am in a sexual relationship with her husband. She made small talk with her friend whilst I got us drinks. Her friends husband joined me at the bar and whispered I can't wait to fuck that tight little ass of yours again. I said I can't wait to have you inside of me again. I so so wanted to kiss him, but obviously couldn't in such a public place, however I managed a quick snog in the toilet with him later. I do like this man he's so much fun.

SISSY CUCKOLD HISTORY 810.
Have you noticed as a Feminized sissy cuckold how your brain never shuts down your whole thought process is about your being’s version of sex!
You think about women and sex the way they dress and how they control the men that buzz round them like bees to a honeypot.
The denial of you engaging in any participation in the act of pleasing a woman in the normal way does nothing other than make you humbler and more submissive literally groveling at their high heels and don’t they know you’re a pathetic sissy cuckold.
And of course, your captive to the need and desire to dress in women’s clothing and to look feminine.
Once your chained in for life to being a Feminized sissy cuckold you will obey sadistic commands from any woman, any cuckoldress and any Mistress no matter the consequences
Worse still you’re so under the heel of women and your fetishes that even men, master’s or bulls can do what they want with you because you have no spine as a feminized sissy cuckold and will submit to the grossest indecencies from any man that makes you serve him! If it might just, please and entertain your Cuckoldress

SISSY CUCKOLD HISTORY 809.
Still on the subject of Prostitutes I as a humble Feminized sissy cuckold had the great honor of being married to Tania my second wife and Cuckoldress for eleven fantastic years serving her.
She is an amazing woman first when we got together becoming a chatline operator/dominatrix then a real-life professional Dominatrix and finally adding to her curriculum vitae Lady of the Night/Prostitute.
By then I was already well and truly Cuckolded by Tania who saw a string of men and had me living as her chastity locked Feminized sissy cuckold maid totally controlled and dominated by her.
The pride I felt when she informed me that she was going to start having sex for cash was so intense that in the car where we sat my little sissy clit free for the first time in months just exploded hearing her words telling her in the most graphic fashion that as her sissy cuckold I would support her every inch of the way in her new endeavor.
And it was an endeavor that went more than well seeing her fuck hundreds of paying clients some she detested and some she really liked mostly she worked with condoms, but she did start having a little book of punters who she fucked bareback.
There was also nothing that Tania would not do all her sex holes were for purchase and for me this was emotionally wild and pain inducing locked in chastity as I was.
And because for security we had spy cams in the studio she worked in I was able to watch her having sex as a prostitute hundreds of times knowing that I had helped her get ready for other men and after when she came into the house I would kiss her high heeled feet in gratitude or if she had done a bareback she would have me creampie clean up from whatever hole she had taken the spunk in!

SISSY CUCKOLD HISTORY 808.
Over the years of being a feminized sissy cuckold I have had periods between marriages when I have seen quite a few Ladies of the night and all of them have after I have explained what I was looked kindly upon my visits.
Not only have they given the sweet taunting teasing humiliation I need, the foot worship, ass licking, pussy eating and denial I spoke of all have on subsequent visits advised me on what time they wanted me to come to them as all working ladies have certain clients they do bareback and they all want to have a feminized sissy cuckold lick them clean which I of course am more than happy to comply with.
My other craving to serve as a toilet for the Cuckoldress is also liked as many working women have a side to them that needs to take things out on men and there I am ready for them to piss on, spit on and shit on or in and all of them afterwards have spoken about what a delightful grudge easer my submission is to them.