SISSY CUCKOLD HISTORY 836.
I will never forget the first time Tania my second wife and Cuckoldress and practicing professional dominatrix made me go into her dungeon and prostitute myself with a homosexual client to earn her money.
I even remember his name Simon a painfully thin lanky tall guy with glasses, I was as nervous and scared as hell greeting Simon as like I have explained before I am not a natural sissy cock sucking queer due to historic abuse.
But I had had more than just a few gay experiences prior to this session Tania had booked me to do.
Remember there was no privacy in what I was having to do as Tania’s dungeon was rigged with spy cameras, and I knew she would be watching make sure I satisfied the client and acted and reacted in the proper whore like manner that she had taught me.
Simon got the tribute out of the way first handing over to me the sixty fee, I left him for a moment to go and give Tania the money while Simon stripped naked and was shaking all over as Tania ordered me back into the dungeon to do my work.
Seeing Simon naked waiting for me in the dungeon made me almost pass out with terror as for a tall thin white guy he was very well endowed his semi flaccid cock hanging almost to his knees.
Simon could clearly see I was a mess of nerves and as I tried to do a slow sexy strip down to my lingerie, high heels and stockings he pressed me with questions about my gay experiences and finally that he was my first punter since my wife had enforced my career change into becoming a feminized sissy cuckold prostitute.
Simon talking did help to calm me a bit and next I was squatting in front of him like a slut holding and caressing his large smooth balls as I suck as much of his huge cock as I could all the way into my throat where I struggled to breath properly and let him face fuck me as he held my head in his hands.
I had a really good taste of Simon as he leaked a huge volume of pre cum and took himself to the edge in my throat three times before getting me up and leaning me over the massage table in the dungeon.
Via the mirrored wall I could see Simon lubricating hugely erect cock up his eyes greedily scanning my lingerie clad sissy cuckold body, strangely Simon before taking me used on of his hands to caress and manipulate my in scared little penis to an aching erection so skilled was his hand.
So, it was with the delightful feeling of my sissy clit being fiddled with that I gasped when the bulbus head of Simon’s hard erect cock pressed against my twitching spasming tight little sphincter.
With more and more pressure being applied by Simon his cock head finally popped into my rectum making me wail in pain at the huge intrusion as my ring was broken into by gay cock.
Simon luckily was a thoughtful guy and knew his cock was something that not many could handle and the next minute one of his hands came in front of my face holding an open bottle with a heady scent in that soon had me spinning my mind and body experiencing a delightful sexy thudding and throbbing and my tortured sissy pussy opening relaxed and I groaned in a shameful slutty manner as Simon eased his large cock all the way into me till his balls slapped hard against my one tight little testie.
Over the next hour Simon showed me what an experienced gay man can do as he fucked me to oblivion with long hard strokes that sent me wild and aided by a few more inhalations of the aroma from the bottle
Tania later told me she had watched ever filthy sordid moment of me servicing a gay punter and teased me unmercifully about how sexually excited I must have been for queer cock as I forgot totally to get Simon to wear a condom so I felt the lot when is cock exploded all the way in me as gout after gout of his hot spunk filled up my bowels and triggered off a sissygasm that Tania saw as my weak watery sissy milk hung like strings from the tip of my hard quivering little penis dropping to the floor once the over stretch had been reached.
To my further shame the session ended with me sucking Simon’s slightly shit soiled and smelling cock clean and he actually kissed me thanking me stating he would be back for more.
Good to his word Simon from then on would come for a session about once every six weeks thus I earned Tania a good whack and like any good Cuckoldress Pimpess I was never allowed to keep any of what I had pedaled my ass and mouth for!

SISSY CUCKOLD HISTORY 835.
For want of a better phrase I suppose I was lucky being caught out evolving into a transvestite early on by my mother who liberally for back then encouraged me dressing up and then via gossip with Pam, Fran and Wendy revealed to me what I was destined to become in life a Feminized sissy cuckold.
At the time when I was exposed, I was in stark terror thinking the world was going to end when my little penis erected against my mother’s silky hot nylon foot when I was massaging her feet one evening whilst we were watching television.
Then came her cutting humiliating remark over how insignificant my little penis was and her going on to say she knew was stealing her tights and panties to wear out of the laundry basket and ordering me to go and put a pair on that were freshly dumped ready for washing.
I obeyed how could I not being in utter fear being caught out and I felt less than an inch tall a while later standing in front of her in the dirty tights my little penis so hard it was hurting.
From that evening onwards I was encouraged to wear her dirty hosiery and panties and over time it was all the time and the rest of female apparel and make up.
Now many Feminized sissy cuckolds I have spoken to do end up getting exposed one way or another mostly via their cuckoldress wife spilling the beans to Sissy Cuckolds mother and contrary to popular opinion in many, many cases the sissy cuckold shaking with fear of it’s wife exposing it to Mummy turns out to be the fact that Mummy has known for a very long time that her son was a crossdressing perverts but preferred not to say anything and shockingly will side with her sons Cuckoldress wife in the lifestyle.
This deep meeting of minds between Mother and Daughter in law is the closest and most meaningful in law relationship that can develop, as both Mother and the wife both want what’s best for the Feminized sissy cuckold.