In the early period with Mistress before She had starting bringing Her lovers home, She would go out for the evening sometimes all night. I was still being teased relentlessly with the promise that I would be allowed a release soon. I desperately wanted to cum after months in chastity in cages that were only expertly removed to be replaced swiftly with a tinier replacement. She always brought home a few pairs of panties from work to wash. After all She said She couldn’t help Her mind wandering. And it was very pleasant sometimes to sit for few moments in the warm excitement, knowing and anticipating an orgasm on my tongue later. Much like I might once have enjoyed having an erection and knowing that I could masturbate later, She teased.
I had also heard Mistress talking about some of the hunky Men at the office, on the phone with Her friends, but I was trying not to think about that. Then one afternoon She had handed me a couple of pairs of panties to wash and one pair had a still damp cum stain at the crotch. Like a silly maid I had asked Her about it, and She had replied.
“I do not need to explain myself to my chastity maid.”
“No Mistress, Yes Mistress, thank You Mistress.”
“Curiosity is unbecoming in a sissymaid, go and fetch my canes.”
“Yes Mistress, thank You Mistress.”
“In fact fetch my new crop sissy.”
“Yes Mistress, thank You Mistress.” I had sobbed in misery.
The new crop was
so dreadfully painful, not just the heavy blunt but exceptionally sharp sting
of leather on soft flesh. But also the sharp crack as the blade sliced through
the air then the horridly wet sounding
thud of leather on skin. And the pain so unbelievably intense
immediately, causing you to literally try to involuntarily swallow and choke on
the gag. And the next timed deliberate stroke multiplying and spreading the
pain. Mistress had only recently acquired the crop a gift from
I was gagged with the panties and After six with the crop, I was instructed to kiss the cum stain, which was now clammy from my choked sobs of distress and pain. Then again holding the panties in both hands, curtsy & thank Mistress that She was confident and liberated enough to enjoy sex wherever, whenever and with whom whoever She pleased. And furthermore I was to curtsy and to thank Her absent, for now, lover, fort satisfying my Mistress in ways I never could.
“After all sissy, I do love your tongue, but are you able to satisfy me with that tiny thing in your pretty panties ?.”
“No Mistress, Yes Mistress, thank You Mistress.”
“Which is why is kept locked up, because it of no consequence to me, and being unlocked would not improve your attentiveness nor your housework, sissy.”
“Yes Mistress, thank You Mistress.”
“And sometimes I need a real Man and a nice big firm Man, inside me or to straddle ride.” Mistress did enjoy being on top with real Men too
“Yes Mistress, thank You Mistress.”
Some Mistresses used a large silicon cock over a sissies chastity for sex, if the Mistresses desired
penetrative sex. The device similar to a strap on but attaching over the bulge in the sissies chastity cage. Or some by a different design, sissy was still kept soft and flaccid but encased in the large silicon shape. And Mistress had teased me with images of these devices, letting it be known that this would be by far, to Her, preferable to my own little so called sissy stiffy. Or sometimes a dildo gag, where the sissy cock gagged but with a large 10” dildo protruding from the front of the gag as well, often the gag was equally as large. Sissy must bob and thrust her head until Mistress is satisfied. Mistress had one of these gags too but She only rarely used it and when She did She preferred only to sit on it while it was on my face, I was in no way allowed to thrust or feel like I was penetrating Mistress. But most if not all Mistresses eventually decide, or have already decided, on a variant on cuckolding or being a hotwife is the most satisfying option, for them.
Then I was again gagged with the still soiled panties for six more strikes with the crop before I was permitted to wash the now very soggy panties and thank Mistress again for the privilege.
She had also put sharp silicon punishment spikes, Kali’s teeth, in my chastity for the next few days.
“I think these little reminders.” She had told me showing the rows of sharp silicon teeth. “Will be an appropriate reminder of who is to pleased and who is to please, don’t you agree sissy.”
“Yes Mistress, thank You Mistress.” I had sobbed and sobbed even more miserably as soon as the tiny chastity cage closed and the teeth immediately started to dig in, as even my flaccid clitty began to swell in the chastity tube.
But fortunately had relented after a week of misery, as sissies shouldn’t be thinking about their pathetic clitties so much She told me.
That cum stain had also seemed so much thicker and bigger than anything I had ever produced. But this was auto conditioning too. My remembered little pre chastity squirts seemed so very weak and thin, even though I remember getting overexcited and squirting prematurely on a lot of occasions and being left feeling soaked. But they always seemed so pathetic compared to a real Man, even a real Mans precum was much thicker and voluminous compared to my own pathetic mess.
A very long time ago now, when I was milked for the first and last time. Mistress had been teasing me
for months, telling me that I could expect a release next week or the beginning of next month, as long as my housework was impeccable & Her orgasms were equally if not more so. Mistress had taught me exactly how She expected me to perform, but I was also to learn new techniques and tongue strokes & rhythms to surprise and delight Her. She would nearly always have multiple waves of climaxes, or a massive orgasm, and would expect nothing less. But for months now She had been half promising and teasing me, only to find a reason at the last minute to postpone. But then to my surprise I was told the night had arrived, but also that we were having guests.
Mistress had invited Miss & several of her other lady friends, for the occasion. In that respect I was quite fortunate as sometimes the women bring their lovers along too. I was expected to serve drinks then told to bend over a padded bench in front of the guests. It was the same bench Mistress used for pegging or punishing me but in this case my chastity was not pressed onto the bench but pulled slightly downwards and rearwards and a wine glass placed underneath.
I feel so foolish now not realizing at the time what was happening as Mistress snapped on the medical grade black latex gloves behind me. But then again I was extremely naïve and inexperienced up till a couple of months ago I didn’t know what pegging, queening or a butt plug was.
All I felt was an extended liquid sensation until Mistress withdrew Her finger and told me all done, pushing my very phallic butt plug back into place.
Mistress had laughed and scolded me in front of Her guests, for the look of disappointment in my face, when it dawned on my the realization there would be no orgasm, or any cumming sensation at all, sissy squirties as Mistress called them.
“Did you really expect a little squirt sissy ?.” She scolded amused “Well never mind, you can still give me a lovely orgasm later.”
“Yes Mistress, thank You Mistress.”
“And we can have a little chat after my guests leave cant we sissy.” She said sweetly but icily.
“Yes Mistress, thank You Mistress.” I had curtsied smiling sweetly to hide my misery knowing the little chat would involve a caning first.
One of the Ladies had giggled at the expression of fright on my face.
Later that evening, She had already been so wet, I could smell the sweet waxy smell of Her heat, when
She sent me for the cane and the cuffs. The Misses and Mistress say they enjoy that sense of dominance and power, and our powerless fright, as much as the discipline itself. Mistress tells me that often when She sends me for the canes or crops it makes Her so wet and hotly aroused, that She must be very determined to continue with the punishment, which serves to make the punishment that much fiercer.
It was the thicker rod like cane, and She had also gagged me with Her soaked panties, while putting on a dry pair. Then after six with the thick cane She sent me for the thin springy cane and gave me six with that too, Until that time She had used these canes separately. Preferring the thin cane as a general purpose cane, for a quick punishment or almost as a reminder if She was trying to emphasize a point. But after this night She always used the two in conjunction if She wanted to punish me. And She gave me twelve with the springy cane that night.
She had paused after the usual 6 but I could sense Her excitement as She told me
“Six more I think sissy.”
Afterwards as She sat down and I removed Her 2nd pair of panties they were quite literally soaked, nearly dripping.
Her multi climax orgasm was so powerful, and She immediately demanded a follow up, after I had fetched Her a glass of chilled wine of course, and a third before She was finally satisfied and exhausted enough to sleep. She had allowed me to assist Her as She changed into a fresh night slip and the discarded slip was soaked with Her sweat and arousal at the hem. As were Her silk sheets which I had to change, before She allowed me curl up beside Her and spoon Her as She drifted off to sleep satisfied and content.
My only consolation was that She hadn’t chosen to use Her crop, and of course feeling and hearing Her orgasm was always so exciting and fantastic for me
The next morning after She had left for work I had been so excited in the laundry room hand washing Her intimate lovelies and the sheets, I had to stop and squeeze my thighs together several times just to continue.
Later after She had returned home She came down into the laundry room to watch me as I ironed the sheets and Her panties.
“Whatever is the matter sissy.” She had teased very happily
She had actually had me kneel down ion the laundry room for cunnilingus there and then. But later that evening She had gone out again, although it wasn’t said, with Her then boyfriend.
And as I had remembered from that night that total lack of orgasm or even a squirting sensation for me,
just a rather sticky leak and a vaguely emotional emptiness and totally unsatisfied. Still very horny and desperate to be attentive. I was given the wineglass half full of my discharge to drink. As I stood in front of Mistress and Her amused guests sipping the little glass of weak liquid in front. One of the ladies teased me, not Miss, this time ‘don’t worry sissy, my own maid tells me it tastes much thicker spurting from a real Man.’ Naively I had blushed not realizing what She meant & not knowing that I would be starting fellatio training the following week.
Miss had been teasing me for week about lip gloss and pouting. Telling me that real Men a soon as they see lip gloss on certain types of Ladies they start to think of fellatio, and Mistress insisting that I put on lots of very glossy lip gloss, and maintain a pretty pout. Especially when Miss was bringing Her boyfriend over with Her. He did come over with Her quite a lot. And unlike some of Mistresses other male friends at the time, He seemed very confident and dominant around me. Patting or slapping my bottom as I served drinks, especially after Mistress insisted on lots of lip gloss.
then that afternoon Master & Miss had arrived, and without much ceremony after I had served drinks, Master had told me to fetch the pink leather cuffs that Mistress usually used for pegging me, and expertly locked me in the restraints. He pulled me over His knee and spanked me, While Mistress and Miss watched. Spanking me so hard with the flat of His hand, then temporarily releasing my wrists from the cuffs told me to fetch Him a cold beer. Mistress & Miss had wanted fresh white wine too. Then He had pushed on my knees between His open knees and opened the zipper on His pants. He was already hard and massive, my face was in His crotch, in the heat and the smell of Him.
Before this moment I had only knelt before Mistress & Miss while they wore a strap on and performed fellatio on the strap on. Miss never penetrated me incidentally, just Mistress for now. But She was the only other woman Mistress allowed to use the crop or canes on my behind. In my naiveté I had assumed that this was fellatio training, but I was to be rudely awakened today.
“Look up sissy, let Him see how much you want to please Him.” Mistress had told me.
“Yes Mistress, thank You Mistress.” I whispered frightened and confused
“Pout prettily sissy, part your glossy lips ever so slightly, ready to be pushed wide open by Him.” Miss coaxed.
“Yes Miss, thank You Miss.”
“Ask Him prettily to be allowed please Him sissy.”
It was the last thing I wanted to do I wanted to look away and run and hide, but didn’t dare disobey my superiors. Mistress, had already told me to fetch the crop for my special training.
“Yes Mistress, thank You Mistress.”
“Please Sir, may sissy please You Sir.” I whispered at this point He was still Sir.
“Speak up sissy, don’t you want to please Sir.” Miss told me.
“Yes Miss, thank You Miss.”
“Please Sir, may sissy please You Sir.” I said a little louder.
“How would you like to please me sissy ?.”
“Please Sir, may sissy kiss You and lick You Sir, and suck You Sir.”
I wasn’t allowed to say cock or use any rude words, sissies must always be polite and respectfully
demure
“For my pleasure or for your needs sissy.”
“For Your pleasure Sir, always for Your pleasure Sir.”
“You may kiss me sissy.”
“Yes Master thank You Master.”
And the taste of Him was so much stronger than the smell of Him, as I kissed His shaft and then His balls in turn before returning to His shaft up to His glans, I was rising on my knees to kiss Him.
“Tell Him how big and manly He is sissy. How glad you are to be in chastity so you can please Him. How excited it makes you feel, even though it is always for His pleasure.” Miss coaxed me
“You may suck sissy.”
“Yes Master thank You Master.”
And then the taste of His swollen glans in my mouth as I bobbed my head taking Him slightly deeper each time. Just how Mistress and Miss coaxed me using a large very realistic dildo. He was very well endowed even for a Sir. Miss says sometimes She cant decide whether He is a little too much, or if She is so lucky. And of course Her four household sissies fear & love His cock as much as they fear & love Mistresses strap on.
Then the splash of hot somewhat sweet precum, with a hint of His cum and urine too. But then spluttering and gagging followed by the thick sticky spurting in your mouth until you are full and He splatters your face too, before His is finished.
And waiting on your knees not even allowed to swallow until He gives you permission. Choking on the thick wad of cum gagging on the taste in your mouth as you struggled to breath. Then the thick, slimy and sticky taste of a real man, and struggling to swallow, knowing you must swallow prettily& appreciatively. Gasping and panting between gulps, the thickly warm and sticky moist taste of Him and
humiliation as you thank Him for being allowed to swallow being allowed to please Him. & how wonderful it is to taste His thick manly cum.
Mistress tells you to fetch the crop and you kiss it on all fours in front of Him. Tasting the leather tab pressed to your lips, the taste of sex and fear on the whip mixing with the thick taste of His pleasure on your lips. Before either She or Miss bend you over for six lashes, then tells you must perform much better, next time show Him how much you want to please Him, how at that moment all that matters is His enjoyment. How fervently you adore His cock.
You are sobbing in pain and shame, but curtsy and thank your superiors sweetly. A short time later He calls you over again, and maybe again, until He is satisfied, or bored by your fervent but still blossoming performance, for today at least . My bottom swollen red & raw from the crop but Mistress was so turned on that She sent me for the strap on. And She and Miss had gone out shopping for a new
and bigger strap on the next day. The training went on like this daily for over a week until Mistress decided She was satisfied with my progress, but I would have to improve each and every time, She warned me as I knelt and sobbed kissing the well used and still warm from my beating, crop.
For the next month Miss and Sir came round most afternoons. But then one afternoon Sir lat me swallow then while I was still in cuffs told me to go my bedroom and wait face down on the bed. I had looked round in shock, only to see Mistress and Miss watching me with amused curiosity. There was no reproach for Sir.
“Please Mistress.” I had tried to sob, Mistress pressed a finger to my lips to silence me then slipped
down Her panties and pushed them into my mouth, they were very damp already. In the future if Sir wanted to fuck me, Miss would remove Her panties and if it was another guests boyfriend often the guest would give me Her panties. I would hand launder the panties for them afterwards thanking them while I worked and when they visited again I would hand them the scrupulously washed ironed, scented and perfectly folded garments. Or Mistress might put them in an envelope which I would kiss before posting. Often receiving in return a thank you note with a pressing of the woman’s vagina as a signature. I wasn’t allowed to read the greeting as that was for Mistress and only if She decided for me to share too, which wasn’t very often.
Sir then decided to hurry me along standing up and slapped my bottom, then the rear of my legs, as I struggled to. I wasn’t sure what I was trying to do, did I think I could somehow run away, hobbled by
the ankle strap and heels. Not to mention the massive 10” phallic but plug. To escape, or to hurry up the stairs that seemed so very precarious now, in front of Him, preceding Him.
More slaps and squeals of muffled pain and fright, then in my bedroom He pushed me face down unbuckled my ankle strap and lowering my panties unlocked my butt plug and tossed it contemptuously onto the bed besides my face. He was very well endowed anyway, more so than a lot of the Sirs, and I am told it was natural not enhanced. If He felt big in my mouth, which He did, He felt enormous as He penetrated me. Where only Mistress had previously enjoyed me.
He had felt so big penetrating me, inside me, like He was splitting my ass in two. I had struggled and
moaned helplessly into my gag, but that only increased His enjoyment as He pressed me down until He was ready to cum, massively inside me. It honestly felt like an explosion or eruption, both physically and emotionally.
Then afterwards on my knees as I licked Him clean He was still rather hard His cock towering over me, even though I had risen up still on my knees to lick Him properly. He put His hand in my hair, holding a fistful not unpleasantly, rather gentle if a little forcefully still, and for a moment I thought He might want another BJ. But He just wanted to direct my tongue for a moment. Also I was to suck His shaft and suck out every last drop of cum. Often Men would have a final spurt at this point but not today for me at least, though again He did have a final shudder.
Downstairs again I served drinks to Him, Miss & Mistress curtsying, while they laughed and chatted casually as if nothing had happened, even though my whole world had just shifted forever. I felt so totally used and shamed. But He allowed me to sit on His lap for a moment and cling to Him in tears, to thank Him.
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“Yes Sir, thank You Sir.”
“Oh I think a chastity sissy you should call me Master.” He told me.
“Yes Master, thank You Master.”
“That’s better, and eyes down sissy.”
“Yes Master, thank You Master.”
“You may run along to your little chores now sissy.” He told me pushing my from His lap.
“Yes Master, thank You Master.”
I hurried off downstairs in tears, not just from the stinging slap on the back of my thighs. But also in shame and humiliation, but also because after penetration, especially and more so with Mistress I ached to cling close to them, even if it was Him.
After that day Mistress had allowed any of Her male friends to enjoy Her sissies services. After all it
was simply hospitality. And She like most Mistresses became very competitive about my fellatio performance, and the Sirs satisfaction. I was to serve each and every Sir or Master as if I were serving Mistress and try to give them the very best BJ they had ever had, each and every time. Looking up at them submissively but also to make sure I was pleasing them a s much as I could and that I wanted to and loved pleasing them, and also anxious to be so. If there was any hesitation on my part or dissatisfaction on theirs I would be fetching the crop, for Mistress to punish me
Master was the only Man I was to call Master for now until I was snipped, or if I was serving at the hotels and the guest preferred Master. Also Master was the only Man Mistress allowed to use the crop on me. But most Men were expected to and enjoyed spanking me before fellatio. Mistress also sometimes allowed Her regular lovers to cane me using a variant an the thick rod like cane, though never the springy cane as that was very intimate between us.
And although for oral I was expected to be an ardent fervent participant. For anal it was enough that they enjoyed my futile but pretty struggling and muffled protestations as they enjoyed my pretty ass. After all part of the enjoyment was the fact that for a sissy no, means yes, it just required a little forcefulness. It was never rape because Mistress not only allowed it, but enjoyed watching as foreplay for Her own pleasure. And just like the pretty slavegirls who get terribly aroused that their Masters knew they were distressed by anal and insisted on it anyway, gagging them with their panties to make their cries even prettier. It was intensely shameful and arousing to me too. And how lovely it would be to cum at such a moment.
Part of the pleasure after all was my pretty struggling and cries of hopeless distress, rather than my active participation during fellatio.
I was expected to swallow all the cum, rather than have them blow in my face in Mistresses company, She thought it was rather vulgar to have cum on my face and uniform and I would be punished for it. But Master and some Men still enjoyed cumming in
my face, and although Master said He didn’t really care if I was punished or not for being ‘iced’ or ‘creamed’ He and lots of the Sirs still seemed to enjoy it when Mistress told me I would be punished for being such a bimbo.
There was a little element of disgust and discomfort on their part too I suspect. Because even though the hormones and treatment had made my already slight body, very petite and soft, effeminate, I had still once been a Man or rather a girly boy. But I was softly curved and very soft, and the treatments gave me a lovely soft skin and hair and a pretty face. Punishment had quickly trained me to be delicate and graceful, until it became instinctive and natural.
But the Sirs did still enjoy obedient and submissive oral and anal. Very much so indeed and Mistress and the dominant Ladies rarely if ever indulged these desires. It was just too messy or submissive feeling.
Some couples do initially at least indulge in the dominance dynamic popular in the hotwife/cuckold scene. Where sissy is always submissive and the wife is also submissive to the bull. She might get spanked, perform oral and receive anal while sissy watches or is similarly used & treated. But the wife might find this exciting at first but soon becomes bored of this play. Some if not most bulls can be rather boorish, and conceited. For sissy of course this isn’t play and she is for His pleasure as much as she is for Mistresses pleasure and domestic service.
Also at this point if sissy had been allowed the occasional release, or at least a periodic milking. In this scene it is common that sissy is only allowed to cum, or more rather (likely to) be milked while the bull is penetrating her ass, or whilst Mistress is pegging sissy. However at the point where Mistress becomes bored of the play, chastity is soon strictly enforced.
For me though as with a lot of sissies chastity is strictly enforced as soon I had met Mistress, and the
milking, usually after a few months and only once or maybe twice is final, just part of the sissification process.
For some dominant Men enjoying sissies sexual services can also be confusing because oral & anal is so enjoyable, and for some they would love this to be with the Mistress but Mistress generally prefers mutual sex. This can be very passionate and satisfying. But also the sissies totally obedient and submissive intimate service is very desirable. Often a relationship might be ended if Sir seems to enjoy fucking sissies to much the detriment of Mistresses pleasure. And some dominant Men might find themselves tricked into feminization as revenge or punishment. After all the hormone regimen and treatments are very effective, and the dominant male who enjoyed anal so much will soon be getting plenty of oral & anal.
It can be quite satisfying to think of former Sirs being made sissies and getting what they deserve, for just a moment. Until you remember that you wouldn’t recognize them anyway and that you are being treated exactly the same as they are as you deserve to be.
Now that I am pink pantied, my satin panties are a very light pastel shade of pink, or baby pink, with white or sometimes pink ribbons and lace too. Not that any of the Men need to see my panties to know I am available for their exploitation and enjoyment. The news is soon spread by Mistress and gossip in general.
And being pink pantied and put under male discipline makes sissies serve both Him and their Mistress so much more attentively and perfectly. That sense of penetrative vulnerability is so appropriate & perfect for chastity sissies
.
At least that what Mistress says and She always knows best, curtsy.
