For both Mistress and the sissy, sex, both pegging and oral sex are of course very intimate. During oral sex both are also somewhat vulnerable, Mistress, though thoroughly in charge surrenders some control to sissy so sissy can delight Her with her tongue. For pegging Mistress is firmly in control and sissy is totally emotionally vulnerable.
Sissy is often gagged with Mistresses freshly removed warm and moist panties, so Her cries and moans are muffled sweetly. Sissy can taste and smell her Mistresses arousal as she is penetrated, slowly but very steadily and firmly by Mistress. The length and girth of the oversize strap on will cause sissy to throb and convulse back against the exaggerated phallus. Which causes the clitoral insert of the pulse and vibrate to Mistresses delight. Both Mistress and sissy feel very connected and loving too, though for sissy in a totally subjugated way.
Mistress might sometimes wait before gagging sissy, until She is partially or nearly fully inside but sissy
is already feeling massively full. Like the old very sexist jokes about women parking cars and penis size, sissy just cant tell. She will be sobbing and telling Mistress how much she loves Her, and please Mistress be gentle Mistress, sissy loves You Mistress. And Mistress will tell sissy shush, and push the panties in sissies mouth. Often telling sissy She in not even halfway there yet. Sissies helpless moans will just excite and spur Mistress more.
The strap on will insistently enter & penetrate sissy and as it does so massage & inflame sissies prostrate gland. Causing sissy to become hot and desperate to release, but of course only Mistress will climax. Sissy will not even anymore be permitted the empty sensation of being milked periodically.
In earlier times and in some scenes, sissies were permitted the very occasionally usually ruined spasm of release. Or a very periodic milking stimulated by Mistresses latex gloved fingers, medical latex usually. Or by a milking tool, or sometimes a dildo stool that sissy was impaled on. Or during a vigorous pegging.
At one time sissygasms were popular variant sex option. Fashionable for a short time because at this time most sissies were no longer allowed to squirt or even a release with hollow void sensations of being milked. Sissy would be coaxed to reach an anal sissygasm when Mistress Herself reached climax. These so called sissygasms would build in intensity over time and were always very emotional for sissy. The feeling was one of total utter surrender to Mistress, a blissful subjugation rather than one of sexual pleasure for the sissy herself, although still a form of release. And she would feel herself so much more lovingly submissive and attentive to Mistresses afterwards.
Many Mistresses also used a hypnotic trigger word to make sissy sissygasm on command, triggered when Mistress was climaxing on sissies tongue, or during pegging or whenever Mistress pleased, or it amused Her. For example when sissy was sucking or being fucked by Sir. It was especially amusing to see sissy spasm helplessly in orgasm just at the point when Sir exploded in sissies mouth.
Of course once these sissygasms were triggered in sissy, the next step was to control and forbid these
except as a very occasionally treat or reward. Just as with sissies now forbidden, little squirt or leak, it was seen as best for sissygasms to be not an earned reward, but something granted by Mistresses as She pleased. Totally dependent on Her whim and will. Not something a sissy could or ever should think they were entitled to for good performance of her natural effeminine duties, domestic or intimate.
But then after some experimentation & research it was decided, that the desired effect of total subjugation and the post sex after effect of rapturously loving obedient attentiveness, could better be achieved if sissy was brought to the edge by sex, which incidentally She always was, but denied release or sissygasm. And the effect multiplied and amplified for sissy as her excitement dissolved like a burst bubble without satisfaction for sissy, just as Mistress or Sir reached orgasm. The more powerful the eruption for Sir, or the more multi orgasmic for Mistress the better. And in fact feeling sissy so hot and needy made the sexual pleasure that much more powerful for the superior, especially so for Mistress.
And sissy would be so helplessly loving and emotional afterwards sometimes it was actually necessary to punish or threaten sissy with punishment, she was just left so needy. Just as she could be at the special time of the month, when very emotional and tearful sissies needs firmer discipline than usual.
As such it was very pleasant after a pegging to have sissy immediately fetch a refreshing drink for Mistress then for sissy to kneel for cunnilingus, often preceded by a golden drink of urine from Mistress. This would often be very strong and smelly, yellow from Mistresses exertions and Her pleasure and contrasting nicely with the perfectly chilled drink sissy had just fetched for her superior. Also very appropriate is the sensation caused by the pegging, sissy will be quite desperate to pee, but is usually strictly controlled and only allowed to toilet in the morning and just before her daily evening enema. Contrasting with Mistress who may pee and do exactly as She pleases when She pleases.
After Mistress has cum again, or after pegging or cunnilingus on sissies tongue, sissy should be dismissed at least initially back to her chores, starting with washing the panties Mistress removed to enjoy sex with sissy. After sissy has fetched Mistress a
clean fresh pair and another refreshing drink of course. Mistress might and often does feel quite affectionate & loving to Her sissy after sex. But even if sissy will be allowed to sit or kneel with Mistress for some special time, after that most special time. It is seen as desirable that sissy is first dismissed even if only for a short time, to put and keep sissy firmly in her place. For that same affectionate after sex loving feeling & reasoning Mistress mighty often go and sit in the laundry room with sissy, smoking and watching sissy as she washes Her panties. Even though Mistress, has no intention or desire to assist or particularly observe sissies menial chores usually. Especially in that stuffy smelly little room. Though Mistress will open the usually locked window when She is present and sit in its cooling breeze as well as being cooled by the refreshing adaptive AI controlled personal AC.
Similarly Sir or Master enjoys dismissing sissy after sex, especially penetrative sex. No matter how forced the BI, is. After kneeling in front of Him, licking Him clean, then when He is again sitting comfortably drinking the chilled beer or refreshing drink sissy has just served Him. Sissy will be desperate with submissive need to cling in tears to Him. Mostly He will slap Her bottom and tell
her to hurry off to her chores. But very occasionally sometimes delay the dismissal for a few moments allowing sissy to sit on His knee and clutch at his arm and thank Him for His penetration and for being permitted to serve His pleasure.
She will of course thank Him whether she is permitted to dally a few seconds or not. Before He lifts her off His lap and again with a loud slap to Her bottom or the rear of Her thighs. Dismisses her, mincing away tearfully.
Mistresses will often be endeared by this so much that sissy will be summoned for intimate service soon after the Man has left. Or Mistress might call Her boyfriend, or masturbate as She pleases of course. She might decide that sissy was too helpless and pathetic serving Sir or was unsatisfactory in some way, whether Sir has said so or not. Or just because it pleases Her to. She might send sissy for the canes, then possibly have sissy kneel intimately for Her afterwards.
Sex is always for Her intimate enjoyment pleasure and sissy is there to please Her when and how She
desires.
Pegging parties can take several formats its entirely up to the sissies owner. Many sissies are kept exclusively for their female owners intimate sexual pleasure, and sometimes any lovers, boyfriends, male visitors She may have. Many Mistresses are turned on by seeing their sissy serving a real Man sexually, Also sissies who perform so called ‘forced bi’ are that much sweet and submissive in their intimate service to Mistress after being dominated sexually or otherwise by a real Man.
Some Mistresses allow and enjoy group pegging for their chastity maids, especially if sissy was feminized because he was unfaithful or unsatisfactory as a lover, either by sissies current Mistress or a sissies previous, original owner. In fact many an inadequate ‘man’ may find himself feminized for pestering His
girlfriend or wife for oral, or anal, threesomes, when his own little cock is already unsatisfying, and his own performance stultifying. A sissies oral service is never allowed to be dilatory or unsatisfying, sissy must strive to and constantly improve on her oral service, learn all the new techniques and to delight her Mistress every time. And serve Mistresses lovers with that same fervent desire to please and delight Him. Corporal punishment and the constant fear of the cane or crop has a wonderful aphrodisiac effect.
Often these discrete pegging parties wont be held at Her house but at one of the clubs in a privately booked room maybe with 4 or 5 other invited friends. And either one sissy or they might each have brought their own sissies to the party. Sissy will serve drinks, snacks and other sundries before being put over the bench, or into the sex stock. Sissy will usually be cropped beforehand, but only by her own Mistress. Most owners prefer only themselves to use corporal punishment on their property, in their presence at least. It is seen as very intimate. Even Mistresses lover will often only be allowed to spank or paddle
sissy, maybe if He is a long term lover He might also use a thick rod like cane. In the clubs and hotels where sissy is serving male guest the Sir or Master has the choice of a crop or the horrid tawse, the crop is equally horrid though.
Sissy will be enjoyed in turn, then might serve more drinks and be left facing the wall. While the Ladies chat and otherwise enjoy their evening Or left penetrated on a very large dildo affixed to a thin stool. Or sometimes just the dildo stool without the base for sissies bottom to settle on.
Sometimes sissy might serve His Mistress orally, and then the other guests but that is rarer still, as a Mistress might decide to share penetrating Her sissy, intimate oral service is often just that very intimate between Mistress and Her sissy. But on
occasion her hot eager little tongue might be shared in turn by the group of ladies. Sometimes if all the Mistresses bring their own sissy to the pegging fun, the sissies might serve their Mistresses orally afterwards, or similarly take turns. After all a sissies cunnilingus after a pegging or her penetration is quite heavenly.
Similarly and especially if its just one sissy being shared, sissy might be sent to the next room where the Ladies boyfriends will be waiting eagerly. Again fellatio is especially superb after sissy has been penetrated. Or the Men might be invited to be at the party but to not partake, until later when it is their turn and the women are fully satisfied and are otherwise socializing and enjoying the evening .
Some time later sissy, after cleaning Her face and the top of Her uniform, will begin to serve the Mistresses and boyfriends and the rest of a clubs clientele more generally in the main area of the club.
The pegging events, or party pegging nights, are much bigger and more fun, for the superiors that is as
always. They tend cater especially for the younger newer Mistresses who may only have pegged their own sissies and who want to learn and experiment, and for older Mistresses who seem to very much enjoy such events. But many Mistresses may just pop in for the fun too. It is entirely Her prerogative.
These events such as they are, are in their own unusual way quite boisterous w with a uniquely female dominated twist, as one might expect. Often it is just Ladies and sissies but sometimes there might be a few Sirs drinking and whilst not partaking still enjoying the show in a corner or at one end of the bar.
There are usually around 10-15 sissies and between 100-200 guests all Ladies and most if all Ladies will there to enjoy the fun. There are also around 20 or so sissy maids who are there not to be pegged but to serve drinks and serve in general.
The sissy maids who are there to just to waitress on & serve drinks to
the Ladies might also be pushed under the tables by the Sirs. That is quite usual & seems only fair. Sissy maids whether waitresses chambermaids or simple maids are of course is kept in chastity at all times.
The sissies who are for the main event usually arrive an hour or so before the event starts along with the serving sissies. They will prepare the tables and all the equipment, sex stocks, cock stools , strap ons and harness. Before being seated, on the stools and displayed. For the event theses sissies will be wearing rather than their usual maids attire, very glossy tight fitting nightwear. Such as is worn when intimately serving, or at bedtime in general. However panties are not worn, sissy may hold on to them throughout the evening to wipe Her face down if permitted. She is cuffed, hands or wrists rather secured in the small of her back. And even if she is gelded as most are, she will still be wearing a pink silicon chastity cage. Auto ghost suggestion will give the
sensation of a flaccid but full & swollen cage. On arrival she might still be in her maids uniform and plugged. But once dressed for the evening, and cuffed Her plug is removed and she lubed and is penetrated atop and astride on one of the rows of phallic stools.
Her normal dildo plug, inserted at all times and enlarged for intimate service, will be used as a very deep cock gag for the evening. Actually this isn’t quite strictly true anymore. Most plugs these days are very deep 10” if not 12” and stout too. Sissy can just about accommodate this in Her mouth, But the plugs also often have an attachment that makes the sissy feel there is a huge pair of swollen manly balls attached. Embarrassingly for sissy, she also cant tell is this enhancement is at the front or rear
whilst She is plugged. This is actually very small and discrete, visually but considered a bit unsightly or vulgar. Instead a similarly sized cock gag is used to silence sissy, with a non visual attachment that serves the same purpose, increasingly as is becoming the fashion this type of device will be used every day for both daily anal penetration and for cock gagging when desired by sissies owner. The gag has an exaggerated set of very plump glossy lips, usually with a keyhole as a detail, indicating that sissy is locked, but the superior has the keys. The other feature of these party gags is that although they are equally deep and stout as the daily plugs, sissy is not completely muffled. You can still hear her moans and whimpers of submissive sexual distress & misery as you penetrate her. The effect is very appealing similar to pantie gagging sissy for sex or punishment.
Some of the sissies are also wearing ring gags. A gag that keeps her mouth wide open in an O shape. The ring is covered, or decorated by a pair of glossy plump lips in that exaggerated fellatio ready shape. Which is
exactly what the gag is designed for if desired. The cock gag is then inserted in the O ring and locked.
These O ring gags or a minor variant are also sometimes used on a sissies anus for the same effect. Sometimes popular with the Sirs, but not really much with the Ladies and not that popular with the Sirs too much as a well lubed very tight ass is much preferred, although the O ring can be a nice occasional novelty.
All sissies will also have their anal intimacies bleached pink so as to be appealing to Sir or for
pegging. And the design of the bleaching can make the pucker shape appear like a pair of very full, very expanded lips when sissy is penetrated. For some reason having this procedure done and being told the reasons why for it being done can be very distressing for sissies. Even though it does look very pretty and they should be grateful to be pretty for their superiors. The procedure does sting and smart for few days afterwards but that is not a concern as it does not interfere with sissies
housework or her other duties.
The sissies are very well lubed for the evening. The new highly engineered lubes make sissy feel exceptionally tight but for the penetrator also tight and as slippery as if a hot knife through butter for Him or Her. For her part sissy feels like she is being opened and split, and she cant help but struggle feebly and squelch and squidge back against the cock, silicon or flesh. This resistance
often in spasms feels lovely and thus is very enjoyable for the penetrator.
Complemented by sissies lovely muffled helpless moans of distress and protestation. Ignored of course, just encourages Mistress or Sir to go deeper and harder.
The new lubes have been so popular that they are being used for sissies daily enforced plugged penetrated state. sissies have reported that even a little finger constantly feels like a hugely swollen cucumber or bigger down there. Mistresses have commented jokingly that if sissy were long enough and allowed to be hard enough to penetrate another sissy even her own tiny thing might just about be noticeable, with these lubes.
And as such the lubes are constantly being refined for the superiors sexual pleasure, tighter and more slippery still. The lubes completely prevent tearing, ruptures or infection, but do not stop
the sissy feeling very tender afterwards, but this is to be expected.
When all the sissies are on display so to speak. They are left on display but themselves in semi darkness until the party really starts. The sissies constantly struggle haplessly to stop themselves slipping too deeply down on the stools. But they are so slippery that all they can do is squelch and squidge around the huge cock stool. Actually there is hidden safety feature to stop them going too deep and causing physical damage but the sissies aren’t told this. There is sexualized muzak with gasps and moans of female orgasmic ecstasy piped from the speakers in the gloom to accompany the muffled moans and wet squelching.
Over the next hour or so the attendees will arrive and be served drinks and refreshments by very anxious serving sissies. Theses sissies will mainly be new inexperienced sissies, so they will be very nervous and flustered, in addition often at these evenings one or two of the serving sissies will be unexpectedly joining the main
entertainment. Adding immensely to the delicious frisson of sex and fear amongst these serving sissies.
As the event gradually fills up, the bar and seating area will become very busy and loud with the carousing. The happy sounds of dominant Ladies enjoying each others company drinking and laughing.
The Ladies will come over in small groups or individually to inspect the sissies. Fondling and slapping their bottoms and squeezing their chastity cages, whether imaginary full or not, the effect is the same. There are crops and paddles provided if Mistress wishes to use them. The sissies are all numbered, with a round tag on a choker around their throats. At other occasions the numbered tag has been attached to a penis/clitty piercing, or an exposed nipple.
Then after a brief inspection the Ladies will continue observe from
the bar or their tables until the evening really gets going. It will be long evening and there is a fun atmosphere before the pegging gets properly in swing.
Because this is very much a dominatrix themed event the Ladies mostly dress the part either very sensual latex clubwear or Domme type clothing. The sissies wait squirming helplessly, and although the music is very loud all they can hear is the sound of their own and each others moans and squidging. The dance lighting high lighting the sissies in lurid colours for the watching guests. All the sissies can see is a mass of Ladies as they party and gee each other up for the main event.
It will start informally as a group of Ladies will
select one of the sissies and have her lifted from the ‘pole’ with a very wet sounding slurp. Sissy will immediately fully tighten up, both because of the lube and her fright as she is led to the sex stocks. By this time other groups of Ladies will probably have selected a sissy for their entertainment too.
The stock keeps sissy facing the wall so she cannot see behind her. Some events have mirrors so the sissy can see who is pegging her but not discern the dominants face properly. But in this case just the blank wall. Sometimes the sissies might be in tight leather bag hoods too.
Sissy is either on all fours low down in the stock, they are adjustable. Or stood up but bent at the waist in the device. The sissies ass in the device can be raised or tilted for convenience. Sometimes the sissies hands are locked in the stock, in the traditional style besides her head, or mostly just left locked in the cuffs. The sissy might have her legs split widely with a spreader bar, or locked closely together for extra tightness. The strap ons for these occasions are very generous 12-14” and correspondingly thick. They all have the delightful clitoral extension or bulb for Mistresses pleasure and climax. And
sissy will be fucked or pegged in turn until all the Ladies are fully satisfied. The Ladies take it in turns until all are sated for the moment, however sometimes they might swap sissies with the group along side them. The Ladies take sexual enhancers all evening to maximize their stamina performance and of course sexual enjoyment. By the end of a night they will have al least fucked most or all the provided sissies at least once and will be quite exhausted but completely happy and satisfied. Its usually best not to have a work day after these parties. There is lots of cocaine and other performance enhancing and energizing drugs, so there is an electric buzz amongst the Ladies. The sissies of course have their housework and chores for their owners as always the next day.
The Ladies sated, for the time being might sit down for more drinks, handing over their well used strap ons to the serving maids to lick clean who will be very nearly choking with fright themselves. The pegged sissies might be given a slight respite and put back on the stools, but it is only the briefest of such, as it as always is a very popular busy event and there is a throng of
Ladies who want to enjoy pegging the sissies nice, tight fuckable asses.
By around 4 or five hours of pegging, drinking and relaxing and then more pegging and more socializing the evening will die down. The sissies will be allowed down from their ‘seating’ properly plugged again now, for a more relaxed intimate service.
There is usually a core of around 5-10 Ladies usually amongst them are the sissies owners, who want to stay behind and drink whiskies, brandies and expensive liqueurs, as well as smoking cannabis cigarettes late into the night. The well pegged sissies will attend these Ladies performing oral sex, which after such a thorough pegging is exceptionally heavenly. Also at this stage of the evening the sissies will regular oral peeing duties for the Ladies, in between cunnilingus. The sissy will spend most of the rest of the night under the hem of a leather skirt or several. All of which will be very warm and moist with the excitement of the event.
The atmosphere at this stage is very much that of a 19th century
gentleman’s club, or cigars and brandy after the ladies have retired, with an obviously highly erotic touch.
The Ladies will sit about chatting happily, only interrupted when one of them gets overcome by pleasure and climaxes, much to the amusement of the other Ladies. Sissy will then be passed along or around. The serving sissies will run and mince around serving drinks and cleaning up. Bringing the Ladies fresh clothing and panties if required, until everyone has decided to go home or on for the night.
After the night finishes sissy will go home with her Mistress and will often spend the night in bed with Mistress. Most Mistresses will be both coming down from the party drug cocktail and be feeling very affectionate towards their sissy and want to be spooned by the loving sissy maid. Some very lucky sissies even get spooned by their Mistresses.
A sissy is always especially vulnerable and attentive after penetration for a few days after such parties. Their oral service for the next few times is even more superb, if you cant imagine that, you would need to experience it to believe it. And in the following days the parties the sissies are in that lovely pliant state and so very eager to please.
Any of Mistresses male guests or her boyfriend will enjoy that superb oral service as well as Mistress. The Mistress will usually indulge Her lover, after all She has had Her fun and its only fair that He should too. Sissy of course remains in chastity.
And If any the sissies are owned by Mistresses who host private guests for tips, the fee will be at least double for the next day. This is usually advertised in advance and sissy will find Herself booked up & on her knees for most of the next
days.
The Mistresses club owners and party organizers all share the takings for the pegging nights and Mistress will usually buy Herself a nice treat with her share, some exclusive designer lingerie or an expensive crate of wine. Sissy might get a new babydoll to serve Sir in, or a new pretty uniform. One sissy was told that she was helping to pay for her new breasts by these nights. A slight tease because her owner always intended to pay for sissies buxom cleavage anyway.
It has been suggested that the sissies might be rented out for men’s parties after the nights finish to earn even more tips. But in all honesty the pegging parties themselves finish so late, its just not that convenient.
In any case let poor sissy take a little rest, she already had too much fun for one day/night or week. Mistress might say.
Sissy will typically receive a covert pick-me-up in the morning, concealed in her tea. She may even be permitted to bring Mistress breakfast in bed, kneel next to the bed, or even sit primly and respectfully on the side of the bed and sip her tea.
This is not always the case, though, and the next day the sissy will usually just go back to work as usual. The pickup or pep is fairly typical, though, because a tired sissy is not a pretty sight.
Naturally, sissy will continue to be extremely sensitive and tender for the next few days or so, but she must always be careful to be graceful and pretty, smiling obediently while submissively carrying out her housework. However, occasionally a quick caning will be required, or perhaps just desired, to wrap up a fantastic occasion for the
superior. Until the next time.
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