SISSY CUCKOLD HISTORY 759.
For the Feminized Sissy Cuckold torment is never just sexually based with a Cuckoldress that knows her onions!
Tania my second wife and Cuckoldress as well as being a Dominatrix and Escort foisted on me a never ending catalogue of mentally crushing events.
Of course it was humiliating (well not for me a born tranny) enough having to be dressed and made up as a woman all the time everywhere we went but say when we ate at a Bistro or such Tania would choose the order and she would always order for me the food I least liked.
What a waste I hear you say but under threat of punishment I was made to clear the plate and Tania would always insure that with my meal I had a glass of her urine to wash it down with. It was little things like this that over time made me incapable of any independent thought or action always turning to Tania to seek guidance on what to do and what to think and that in the world of my Cuckoldress also led to punishment for bothering her with as she put it stupid questions! (You can never beat the sheer logic of the Cuckoldress or avoid the outcome which is always painful and humiliating for the Feminized Sissy Cuckold!)

SISSY CUCKOLD HISTORY 758.
One of the things that always drove me to distraction and a sissy cuckold frenzy was and is the fact that every man that my cuckoldress wives or partners over the years has fucked touched places in my wives of these women that I never could feel (I am talking about the very few that acutally lowered themselves to have intercouse with me!)
The sickness you feel as your Cuckoldress describes graphically what it feels like to be fucked so deep and hard makes every sissy cuckold emotion rip through you knowing that for your Cuckoldress you are an abstract failure on a colossal scale and your only hope to be with her is to do her bidding no matter how degrading, shameful and humiliating
For us sissy cuckolds the best we are ever going to get is licking up and swallowing the sperm and cunt cream that oozes out of our Cuckoldresses pussy and anus and for that honour we should be eternally grateful!

I discovered something about myself yesterday that I never knew existed. I arranged a date with an old friend who's in the country for a few days. I dressed up to the nines just as I know he likes to see me. Bit more difficult these days sice I have put weight on since my operation. It didn't seem to matter what I did, I couldn't get much of an erection from him and I started to feel bad about myself as I felt like I had dissapointed him. Out of the blue, he asked if I had any punishment tools. We have a few things knocking about and at his request, I started to beat his bottom with a paddle. I've never done this and it felt quite alien, especially as I am deeply submissive. Of course Ive been spanked many times over the years and paddled. After ten minutes his bottom was nicely red and low and behold he had a nice erection that I took full advantage of. But my point is that I realised I was enjoying myself punishing him, which is not in my nature. I think I'd like to do it again and see if it was a one off thing. I'm seeing him again before he flies home to Spain, so I will pop the question.

SISSY CUCKOLD HISTORY 757.
Once a woman has got her talons into a Feminized Sissy Cuckold their will to experiment and push the boundaries knows no limits.
You can understand that any female would be rather shocked and unsure of what you are professing to be treated like, and your relationship change or new union could get off to a stuttering start as she takes little steps to see how far she can step over the line.
Little by little she will gain confidence, and she does things that she thinks would destroy any normal relationship from the first date, to the first creampie clean ups.
Slowly she will feel the release of power in her as you her feminized sissy cuckold willingly accept any humiliation, degradation and perversity she decides to inflict on you!
Once a woman feels that power in her she will know no bounds and believe me when it comes to making a Feminized sissy cuckold suffer a woman has a never-ending list of things she will do to you.

SISSY CUCKOLD HISTORY 756.
The most sensual sexual thing a Feminized sissy cuckold can see in its pathetic life is when it's Cuckoldress stripped down to her high heels, sheer black stockings and suspender belt stands over its head and slowly squats down.
As she makes the lewd position, she reveals that both her shaven pussy and anus have both been fucked hard maybe by multiple men and they are gaping red raw swollen and dripping and before she has chance to bring her holes to your waiting adoring mouth your face is getting drips of spunk hitting it.
The smell of sex is of course overwhelming, and your little sissy clit is agonized in its secure chastity device and as her fucked cunt gets near your mouth your tongue is flicking out desperate for the first taste.
And when your Cuckoldress is settled and your tongue delves deep into her it causes a cascade of the sperm that real men have fucked into her and cruelly as you clean her she relates how it got there and by how many sending you into a sissy cuckold frenzy with her taunts and teases and how utterly worthless you are to her other than being her clean up girl and slave.
Your Cuckoldress may well avail herself of a little climax on your licking tongue and after she has done so there is that little wiggle and movement and suddenly her asshole is centered on your mouth and you start to probe tasting the fact that anal creampie tastes totally different from pussy creampie as spunk now runs out from deep in her bowels into your mouth all musky and a faecal brown colour with a texture of blended sperm and her shit.
Many feminized sissy cuckolds whether in chastity or not often lose it at this point and shake and go rigid as an unaided sissygasm rips though them such is their excitement!