SISSY CUCKOLD HISTORY 976.
The Feminized sissy cuckolds sissygasm will always have consequences attached to it that are never nice.
Take for example one instance I suffered when back in the day I was kneeling in front of Pamela sucking on her sheer black nylon coated big toe and she suddenly came out with her decision to wank me off.
Of course, my hopes soared to untold heights as although I had been seeing Pamela on a semi regular basis to serve her with foot worship, creampie cleaning and being her maid dogs’ body, she had never not even once touched my little penis.
That promised masturbation by Pamela did happen but not till a few weeks later in the most humiliating circumstances for me.
As previously explained I was early on caught out being a cross dresser by my Mother and then my first experiences of sexual contact came via Pamela and Fran both close friends of my Mother and the three of them along with another woman called Wendy were back in that day were known as fun time divorcees and were as thick as thieves as the saying goes.
The promised masturbation happened early one evening when Pamela, Fran and Wendy were at my mother’s home getting ready for their weekly Friday night out and they were having a few glasses of wine before the taxi arrived to pick them up so all four of them were glammed up ready for a wild night.
It was there in the lounge when Pamela called me in she informed me in front of Wendy, Fran and my mother that she was going to masturbate me as she had promised and ordered me over to stand directly in front of my mother and then Pamela came up behind me ordering me to lift the hem of my dress.
Once I had complied almost passing out with the humiliation and fear Pamela got Fran to lower the band on the tights I was in tucking it under my tight tiny sissy ovaries.
I was already so hard and aching even under the withering gaze of four women who all knew I was pathetically endowed and of course the worst of it was that my little offending penis was pointing straight at my mother.
Readers will already know it was my shame that I had erected against my mother stocking clad foot one night as I massaged her peds which was the cause of me being outed as a crossdresser and my mother’s choice to allow me to dress at home.
But here I was facing her as Pamela reached round and took my leaking little scrap of meat between her thumb and forefinger and informed the girls that she was going to bring me off!
It was then horrifyingly that my mother sort of hitched herself forward thus my penis that Pamela was manipulating was pointing to her deep lush cleavage and then the consequence was voiced “If you dare squirt all over my tits you are going to be spanked and whipped you filthy little sissy beast!”
I promise you I was terrified filled with fear shaking in horror not only from the warning but also the delight of Pamela’s fingers and what she was doing to my sissy clit, I tried to stop myself in every way but with the room filled with their sensual perfume and the sight of stocking clad legs, high heels, sexy dresses and plunging necklines and the non-stop salacious comments mixed in with the threats it was never going to be a winning situation for me specially when Fran and Wendy joined in with Fran reaching up and caressing my aching sissy ovaries and then Wendy easing her hand down the back of my tights and inserting one of her fingers into my tight little anus as Pamela continued her relentless masturbation of my little sissy clit.
It was a long scared horror filled wail of hopelessness that came from my red paint lips when the sissygasm started to rise and I was pleading, begging and offering my apologies to my Mother who was staring at me in a stern saucy way as I lost all control and Pamela’s fingers brought out little jets of my sissy milk that shot out all over my mother’s breasts running into her deep cleavage as I wailed with terrified relief my whole body shaking.
I did my best cleaning up my mess when Fran pushed my face into my mother’s cleavage, but she still had to rush and go and change the dress that I had soiled and was left for the night when they went out that my punishment would take place the following day.

One of my favorite cum play tricks to is to cum in my drink. Then I sip my beer or whiskey with the cum in it while I edge up another orgasm. I like a nice jizz cocktail. What's one of your masturbation or cum play methods?

SISSY CUCKOLD HISTORY 975.
For me as a Feminized sissy cuckold one of the shameful acts that I enjoy but feel utterly humiliated by is when on the rare occasions I am ordered to masturbate in front of a woman or women.
With me being so poorly endowed even just the sight of my smooth-shaven little clit brings forth an avalanche of hilarity and mirth from the watching female and then the snide put downs and comments that sting like acid.
Of course, the first hurdle for the feminized sissy cuckold to get over is to actually achieve an erection under such a tirade of verbal abuse and withering condescension and having to tug on a floppy nonentity brings more shame and a torrent of hurtful comments from the watching eyes.
For the feminized sissy cuckold what really helps is the look of the watching woman or women and also their stressed words on how they only fuck men with big cocks that really open them up none of which even remotely resemble your toothpick like penis.
When and if you can achieve your sissy squirt you might be lucky to be permitted to do it on a stockinged foot or high heel, even the gusset of a pair of filthy panties or just the palm of your hand, what ever way the Lady or ladies deem you should place your filthy little dribble you know that the next step will be that they will order you to accomplish will be the licking up and swallowing of your own mess.