Pegging and Penetration for sissy

 

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 19^th 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.

Pegging Stools

 

The pegging or sissy stools were somewhat of  novelty or curiosity. Either a low stool with a very long & very thick, very rigid silicon phallus attached, or a long stool without the seating platform and just the phallus. These are typically at least 14” with a matching girth, though the seats without the platform can be or definitely feel longer. They are generally a novelty because most sissies are allowed to sit down for too long. It can be amusing to see sissy squirm impaled while Mistress is enjoying Herself with Her lover, or if sissy is going to be entertaining a group of Men, or sometimes Ladies at a pegging party, to leave sissy impaled so sweetly waiting. But this can be impractical as who in this instance would be serving drinks. But most Mistresses will keep one or both variants in the  toy cupboard, usually stored in sissies bedroom along with sissies uniforms, strap ons, various restraints, crops, canes, and other essential sex toys for Mistresses pleasure.  

Sissy might also be instructed to practice fellatio on the stools, especially her deep throating technique. Sissy must always take a real Man all the way in her mouth no matter how big he is. All the way to His manscaped balls, most Sirs on the scene like to keep themselves trimmed, some even shave smooth. Unlike a sissies tiny waxed cherries and flaccid clitty. A real Man erect and swollen with lust can be quite impressive shaved smooth, or nearly hairless. Mistress generally likes to be smooth too, or a very light Brazilian style.

Pushing firmly past a spluttering sissies gag reflex is very enjoyable for Him. And sissy must  learn techniques to maintain His pleasure. Keeping suction and a swallowing method, This helps sissy to overcome the gagging somewhat but also seems to suck Him deeper and deeper, which increases the fucking sensation for Him but also increases the gagging sensation for sissy.

To enhance the training Mistress may squat on the phallus and coat it with Her own juices, although the size of the cock is just to big for Her to enjoy. Most real Men are between 7” and 9” which comfortable but a slight oversized delight for Mistress with Her boyfriends. For sissy though auto conditioning and the tightening but very slippery lubes make Sir feel intimidating at, at least 10”.

Sissies own plug equally straight and rigid is 10”, if She is to be cock gagged, for punishment or

mistresses amusement the gag is usually 7” so it totally fills sissies mouth. Again auto conditioning means that sissy cant tell the difference in sizing. Also auto conditioning, means that Mistress can make sissies plug feel bigger when She wishes. Typically larger when mistress is at home, larger again when female guests, even vanilla  are visiting. Larger again when Mistresses dominant lady friends are visiting, larger still and feeling very much more so with male guests who will be usually offered sissies oral and anal hospitality as well as refreshments served by sissy before and after her service. And then of course even more engorged & swollen when serving Mistress intimately.  

Mistress might of course tease and excite sissy by this display to enhance sissies training but more usually a special training liquid will be used. The thick sticky mucus like texture tasting and smelling strongly of a dominant male musky emissions. Sissy must of course lick and swallow all this clean afterwards.

A well trained sissy will usually bring Sir very quickly to climax. Her glossy pouted pursed lips inviting Him to enter her almost immediately. Sissy will usually be spanked first, unless waking Him first thing in the morning. Mistress usually insists on an over the knee spanking, panties pulled down to around sissies knees or stuffed into sissies mouth. Though Mistress prefers Her male guests to use Her own panties for this purpose. Or as is fashionable these day if a dominant couple is visiting, the lady might remove Hers for Her boyfriend to gag sissy with for her spanking, and then later for sex too.  

Sissy will usually bring sir and the Ladies fresh drinks after her spanking. Thanking Sir and begging Him to be allowed to please Him, while He enjoys His drink. This and the spanking has the gratifying effect of making Sir even more urgent with His sexual mores. Sissy will kneel between His legs, cuffed and using only Her mouth undo His trousers and releasing Sirs already engorged erection. Whilst kissing and licking Sirs balls and His shaft sissy will tell Sir how very big and manly He is, how He tastes so good and how thankful sissy is to be kept as a chastity maid  so she might have the privilege  to try please a real Man like Him.

Mistress and Her lady friends often find it very amusing watching their boyfriend squirm slightly in His chair seeing how long He can resist, before parting & pressing open sissies lips with His glans. Sissy looking up obediently and in awe of Him  as She sucks and licks Him in and out of Her mouth. He will usually spurt a hot spray of precum within a few moments, sissy will be allowed to swallow that, but isn’t often given the opportunity to thank Sir before He immediately and very urgently now pushes deeply into sissies mouth, into the back of her oral cavity and throat.

He will usually cum very strongly and quickly after that, but for sissy it will feel much longer and while she gasps and splutters on His shaft, will be gagging with fright expecting to be choking on His thick cum when He explodes massively in Her mouth.  

He will always fill her mouth and sometimes splatter in her face too, on the  front of her uniform. If she is fortunate enough to be allowed to grow breasts Sir will enjoy splashing cum on her cleavage. Mistress often finds this blowing in sissies face vulgar and sissy might be punished later for her immodest behaviour and encouraging Sir.

In any case sissy is not allowed to swallow until Sir gives permission. Sissy must maintain eye contact

with Sir until He gives that permission. Sissy will usually need to swallow 2 or three times and still be left with a sticky mouth. But after She tahnks Him the final time she must immediately look down. Sissies must normally keep their eyes below a superiors belt line at all times unless performing intimate services.

Mistress particularly enjoys having sissy look up at Her when having Her panties changed. Sissy will be kneeling between Mistress thighs and Mistress will sometimes comment that She hopes sissy isn’t getting too excited, or excited at all in her tiny chastity cage, unless sissy wants to fetch the canes that is.

Although fellatio is over relatively quickly if sissy is training on the stool She must often perform for an hour or so at a time in Her tiny bedroom. These rooms usually without windows are little more than walk in wardrobe sized with sissies bed which serves as a pleasure mat for Sir or Mistress if they want to enjoy sissies ass. Often the door opens directly onto Mistresses bedroom and sissy can also be locked in the room whenever  Mistress sees fit. The tiny room also serving as a ‘toy’ room for Mistress. Has a patent leather curtain over the inside doorway, which sissy may not open without permission. The mattress of the bed is covered in a similar fabric so it is easy to wipe down after sex. Although when sissy is sleeping She may cover the mattress in pink satin sheets.

Sissy will often be allowed to sleep with Mistress in Her bed when Mistress is feeling affectionate. But at other times, and when Mistress  has a lover staying over sissy must sleep in her own little room. In these instances the door will be left open but the curtain pulled closed. In case the pair want sissy to bring fresh silk sheets, lingerie, or to fetch drinks and otherwise attend on them. On other occasions when Mistresses lover isn’t quite comfortable with the presence of a sissymaid, sissy might be sent to sleep in the laundry room downstairs out of the way. Often Mistresses more vanilla lovers be like that at the beginning.  

After sissy has spent some time training on the stool or being taken to the room for sex Mistress will often comment disdainfully on the now stale waxy damp smell of submission and sex. There will in actual fact no such smell or wetness, but sissy will be small and taste it nonetheless.

The stools are not used that often, really for practicality reasons. Sometimes if sissy is entertaining multiple male guests, She can be left squidging and squelching  penetrated on the stool, while the Men take a break with a smoke and a drink, in between bending her over. Or some Mistresses do share their sissy for pegging session with other Ladies, and sissy can be left similarly impaled and on display.

A much more practical and satisfying solution is auto conditioning sissy to always feel similarly impaled and displayed on Her own plug. Chastity sissies are nearly ways kept butt plugged at all times. The latest trend in the design of the phallic plugs, is realistic but highly exaggerated and oversize. The rigid base covered in a thick estrogen infused silicon layer. That is completely dry to the touch, but feels incredibly slippery and wet, inserted and locked in sissy. This combined with the new and even more intense upcoming lubes which make sissy feel incredibly tight but buttery smooth for Mistress or Sir.

Make sissy feel at the same time massively penetrated and being split on the thick shaft. But also so incredibly impossibly slippery. Sissy is unable to keep hold of the massive shaft no matter how much She squelches and clenches around it. All She manages to do is squidge and grind on it as it keeps Her penetrated. Also the lubes make sissies ass feel tight all along the full length of the shaft, not just the sphincter, making sex for the penetrator feel incredibly pleasurable.

Because the rigid plug constantly presses against and massages sissies G-spot or prostrate, sissy feels constantly on the edge of cumming, and of peeing. Chastity sissies are not allowed to cum, and peeing is only allowed with permission first thing in the morning and before bedtime when sissy has her daily enema.            

   

                       

More Mid Afternoon Teasings and Musings

 

Mid afternoon Mistress had come  home from work with one of Her friends, well actually from shopping and drinks after finishing work at lunchtime. Her senior position meant She could choose Her own office hours. The pair had arrived by the chauffeured taxi service and the driver was smirking at me as I opened the door and curtsied to the Ladies. Already  knowing about sissies and sissy maids were, Mistresses friend had actually patted His bottom and told Him to stop staring.

The chauffeur taxi service was just that,  an exclusive taxi service for the wealthy and in this case the wealthy Mistresses, Sirs and Masters on the scene. Most of the male staff were vanilla as were some but not all of the female staff. They wore very formal uniforms although the female drivers wore leather miniskirts and very sexy figure hugging jackets. The male drivers were well built and their uniforms well cut to show off their physique too. These drivers  were also used transporting sissies around, usually in the back of a van or SUV

minibus, with darkened windows so the sissies could see out. But Mistress also enjoyed the eye candy. On more than one occasion She had brought a driver for sex, male or female. And on occasion for a BJ from me. Today though it just the ordinary chauffeur service, though they were also very aware of their more decadent indulgent wealthy clients and their chastity sissy maids.

Most people no matter how vanilla would have attended stags, hens, events &  parties where a sissy had been booked to perform intimate services, after they had watched a very highly paid female stripper or lap dancer, who did not perform such personally demeaning services with strangers, for fees or otherwise, but  rented a sissy for just such a purpose, for Her shows as an extra entertainment for the patrons or  Her guests and increase Her earnings. Many seasoned Mistresses were pleased to send their sissies out to earn tips, to partiers or with sissy Masters/pimps even if they themselves didn’t have any financial need. Serving real Men made sissy much more delightfully pliable and submissive than usual for Her and the cunnilingus was delightful.    

Inside the door I had taken their shopping and jackets and curtsying again, twice, once on each leading knee, in greeting I also kissed their bottoms. Miss (the visitor) on each cheek softly and respectfully. Most of the Ladies like to lean back and wiggle slightly teasing me when I kiss their bottom. And Mistress on each cheek and then between the cheeks very intimately. If we are alone often I am allowed to kiss Mistresses pubic mound through Her skirt but not today. Both Ladies smiled as I stood up again and smoothed down my apron, my fingers hesitating every so slightly over my tiny chastity bulge.

And then watching me again after I had served them drinks in the lounge.

“I do hope you didn’t get too excited in your little chastity kissing my bottom sissy.” Miss said smiling.

“Yes Miss, no Miss I didn’t Miss, thank You Miss.” I curtsied feeling very excited now.

“Yes you don’t want to be fetching the canes again later, do you sissy.” Mistress said icily but amused

too.

“Yes Mistress, no Mistress, please Mistress I don’t Mistress, thank you Mistress.” I almost whimpered, blanching with fright at the mention of the canes.

“They are so sweet & pathetic when they squirm so.” Miss laughed

“Of course I preferred the chastity tubes with spikes for my sissy in the beginning.” She laughed and paused thoughtfully “It didn’t really stop him trying to get erect but it was very enjoyable to watch him try.”

Miss’s husband had cheated on Her & when She found out She had put him in chastity and cuckolded him with a very dominant alpha male. Then She had found She enjoyed having him so tamed and subservient She decided rather than take all his money and assets then divorce him. She decided  instead to take all he owned & then feminize and sissify him. The wedding contact was legally converted into a sissy contract which was totally binding when it came to Her control of him & everything ‘s/he’ had once owned. Not

only that but She did it in front of all of his and their friends, his work colleagues, and even the lovers he had cheated on  Her with. She even then made a play on cheating on, or cuckolding  him with His male colleagues & friends but that was actually just a pretense, not that he knew that. And it was not that any of them talked to him again after they found out he now lower case she had been sissified. 

I knew this because Mistress and Miss often chatted about this in front of me. Either not caring what the maid heard or more likely to titillate and tease me. Mistress titillated Herself would often send me for the  little patent leather heart shaped cushion after Her guests had left. Not so much to protect my knees as I squirmed so intimately, but rather to protect my stockings, my uniform had to be immaculate at all times.

Miss had actually enjoyed being dominated by the bull, as terminology in that cuckolding/hotwife scene

goes. At first Her sissy was just left at home while Miss went out with Her lover. Cut soon sissy was the attendant maid, while Miss cuckolding Him in their bedroom. Her sissy wasn’t actively participating the sex at the time, but She was expected top serve drinks and change sex soiled sheets. Or sometimes if the bull needed to  leave after sex sissy would sleep in the very large wet patch besides Miss who wasn’t.  Afterwards sissy would clean her Mistress, Miss with Her tongue. And later as the relationship developed sissy would also lick the well endowed bull clean too.

Sissy was always very aroused by this. It is quite interesting that often couples who had no prior interest in cuckolding find it very satisfying if they accidentally or deliberately find themselves experimenting. Satisfying for Her at least and increasingly very satisfying for Her, not allowing or delaying any satisfaction for sissy. Eventually curtailing it completely for him.

“Oh I did allow Him a little squirt, and it was a tiny squirt occasionally.” She had told Mistress.

“At first maybe once per week, then once a month and then every few months.” She had continued with complete disinterest. “Oh do look at your sissy blushing.” She laughed

Mistress had looked on with an air of disdain & indifference.

“More wine sissy.” She told me sharply, just to watch me blanche at Her tone. Both of the Ladies  glasses were more than half full.

“Yes Mistress, thank you Mistress.” I curtsied, feeling that horrible very warm but also cold sensation of total fright between my upper thighs.

“Of course you have never allowed your sissy a little squirt have you.” Miss said.

“No of course not, she is much better without.” Mistress replied

“Or at least you are.” Miss said “And I do quite agree, nowadays.”

Mistress had insisted, even before we first met in person, online that I stop masturbating until Her device arrived. I didn’t have long to wait. The next day a courier arrived with my package. It was one of the chauffeurs performing special carrier duties. She was wearing a leather mini skirt as part of Her uniform and was so utterly sexy, I had wanted to masturbate as soon as She left before putting the small chastity cage on. But She had stayed and supervised me as I locked the device taking the key with Her. She had made a point of trying to decide where to put the key before opening a small leather purse containing lots of other keys and dropping it in there, as if it was completely unimportant, which to Her and Mistress I suppose it was.  Much how Mistress often makes  appoint of displaying the ever present tiny key nestling in Her cleavage, or dangling from an ankle chain, or a on waist circlet, if She is wearing an outfit that shows Her exquisite midriff. The d

river had patted my bottom almost comfortingly but definitely patronizingly after that. I was lucky, often this carrier service is a woman and a male chauffeur just to add extra sexual humiliation for the sissy. And sissy once locked might get a firm slap on the bottom from Him. I’m told, or teased rather, that in these cases the Man often will wear quite tight trousers showing His very evident bulge. And on at least one occasion the drivers have decided to have sex while sissy attends them in sissies own apartment, before leaving with the keys, but I think this might be somewhat sensationalized retelling.

The driver had also given me a catalogue and list of shops from where I was to buy a selection of panties from, at Mistresses instruction. Even the pictures in the brochure made me swell in the locked chastity cage, as was Her lovely perfume, as She leaned in,  not at all caring or minding my personal space, knowing I was just a sissy. The panties and the chemise style slips I was to purchase were glossy cream satin because I was still a virgin, to Mistress She had commented rather gaily.

And at first I had very much hoped & foolishly expected this situation to change shortly. It did of course

but not at all in the way I so longingly anticipated. To be allowed a release every so often as a reward, especially as my feminization regime improved. And then later when I entered domestic service as Mistresses maid and sissywife, I had hoped and longed fruitlessly in vain for the occasional squirt. But Mistress had never allowed this. Moreover after around 3 months or so, of teasing and half promises,  I was milked & shamed in front of Her friends. But this only made me immensely more desperate to cum or squirt. But even that very limited empty disappointing  release if you can call the total empty feeling of a successful milking that, this too was for the last time.

Mistress had often told me that She would envision  a future utopia or femtopia, where sissies would never have been allowed to masturbate or cum nor ever even be allowed a full however tiny erection. Chastity & flaccidity strictly and legally enforced.

But femtopia aside,  it was as Her friends laughed and speculated around this ideal for them at least. Very enjoyable to have sissy long for what they once enjoyed so inappropriately, when they should have been dutifully busy with effeminate housework and chores. Even if it was a tiny pathetic squirt or splash. And it seemed that the tinier and weaker the splash the more desperately sissy longed for their return.

Even when as most sissies are, she was gelded or snipped, She still ached and hoped to be permitted to masturbate, just one more time, constantly. The tiny inadvertent often nocturnal leak or splash in her panties was  a humiliating reminder of that.

In fact that was one of the reasons the physical snip has fallen out of favour. Not to be confused with circumcision or frenectomy (to improve oral agility and intimate service for Mistress) incidentally as all generally sissies have these both these procedures as standard. However after a physical gelding a sissy often loses her libido and just becomes unsatisfying, for Mistress, and very docile. So nearly all

these procedures have been reversed and reverted to the chemical process where no such docility or loss of libido occurs. In fact the libido is dramatically increased in chemically snipped sissies, seemingly in inversion to them being able to ever satisfy their denied needs.

The physical procedure can always be revered as it is part of the sissy legislation, that any physical change must be at least theoretically reversible even if the dominant party rarely, never, permits it. There is no stipulation that can this be compelled, incidentally, just that it is a possibility. Similarly it is perfectly legal to cane or whip a sissy, as punishment or just if it pleases the dominant, but no permanent physical damage or change is allowed. In fact on this scene drawing blood is seen as vulgar or distasteful  and any wealing  or welts are usually subcutaneous. Although it is quite pleasing to see sissy wincing ever so delicately and still perfectly, fearfully graceful as She minces prettily. With Her bottom and upper thighs puffy and pink smarting and stinging from a canning spanking or cropping. The only permitted legal physical  change and  commonly used is a very discrete ownership brand or tattoo

on sissies rump or upper thigh. It is discrete but if sissy has been marked as Her owners property very evident to anyone who knows or suspects what it is.         

Miss had also eventually disallowed Her sissy, her releases, substituting them instead for milkings. Which left Her sissy feeling vacant and vaguely numbly unsatisfied, but still very horny and desperately attentive, as if somehow she might still be somehow granted a reprieve or release. At this point Miss had insisted that sissy perform fellatio on Her boyfriends and sissy could only earn a release by satisfying the bull and swallowing the bulls often considerable wad. Then when Miss had insisted that sissy also bend over for Her bull, She had completely curtailed the milking too. After all sissy was no longer by any description a male and did not deserve to cum, squirt or be milked. It was all just too messy, inconvenient for Her and now inappropriate.

It was also around this time this Miss had stopped being totally submissive to Her bull and insisted that if He wanted oral or anal He should call sissy.

“It was just too submissive and degrading I began to find, even though the sex was still enjoyable.” She told Mistress.

“And after all sissies do love submitting to a real Man sexually.”

“Or at least we enjoy watching them perform & do so.”

Mistress & the other dominant Ladies and Hotwives who kept a sissymaid or chastitymaid insisted that when sissy was pleasing a real Man at least orally, sissy should look up obediently and submissively. Smiling and showing loving devotion to pleasing Him and being flattered & gratitude for being allowed to suck Him. And awe at his size and the thick load as if sissy had never seen such a big erection, such swollen balls or a thick load of cum. Even if sissy hated it as we did, or at least we tried to keep telling ourselves, even as we felt our tiny clitties swelling in our chastity at the thought of His huge throbbing erection.

Of course it was ok to struggle feebly with distress when Sir or Master bent you over and spread your bottom before splitting you  with His very evident manhood. Moaning and whimpering in humiliated misery as He forcibly penetrated  you. It wasn’t rape of course because Mistress allowed it. Because He so enjoyed sexually dominating you,  as you whimpered into the panties stuffed into your mouth to quieten   your pretty little protestations. Much as Mistress also relished pegging you in a similar fashion.

Shortly after that Miss had also stopped enjoying being dominated by Her bulls. Her increasing domination over Her sissy had completely changed the dynamic for Her. On the scene there were still dominated Ladies who enjoyed being occasionally dominated by their lovers. And lesbian situations where one lady dominated the other always or occasionally and sometimes switching. But in all cases sissy was always at the bottom and in strict enforced chastity.                          

In fact some Men who start out as bulls or lovers can also be gradually cajoled or otherwise tricked or enticed into being feminized. Some dominant women really enjoy this as

well as seducing cheating boyfriends and husbands and making them into good obedient sissies. The hormones, treatments and auto suggestion techniques work just as well on them  too if they are found to unsatisfactory in other ways. In this scene for the main the emphasis is on Her pleasure, His is secondary, and for the chastitymaid, sissy simply does a she is told.

This had been the case with Miss’s first lover although it hadn’t been Miss who initiated and finished the process. Miss had however been invited to a very special pegging party though where all the former very hunky bulls former partners enjoyed taking turns pegging the now very petite submissive sissy.

“You still ache for a little splash, don’t you sissy, especially when you are kissing my bottom.” Mistress teased

“Yes Mistress, thank You Mistress.” I curtsied

“And mine too I think sissy.” Miss laughed

“Yes Miss, thank You Miss.” I whispered frightened but not daring to fib.

Mistress knew this and often teased me rather testily about kissing Her visitors bottoms in greeting as She insisted I always do, unless the visitor forbade it. And often She might send me for the canes afterwards feigning or sometimes not feigning jealous annoyance. But in any case nearly always enjoying intimate service after my punishment. She would gag me with Her panties so I knew how aroused She was. The injustice and unfairness of the situation adding to Her enjoyment of my piquant distress. 

“And it is so sweet sometimes sissy, I just love sending you off to wash my panties post climax.” She paused “Mine of course.” Both women chortled.

“Knowing you are aching so, is just so lovely, anticipating your tongue and your loving attentiveness, but also enjoying feeling the dominance & power of holding the key.”

“Yes Mistress, thank You Mistress.”

“Such a little splash too, even when we milked you it was a weak little squirt at the bottom of the wine glass, wasn’t it sissy.”

“Yes Mistress, thank You Mistress.”

It was a very small puddle in the glass, I was surprised how little there was after at least 3 months of teasing and frustration.

One of Mistresses friends had laughed, watching me purse my lips as I swallowed.

“Don’t worry about the weak taste sissy, my own sissy informs me that its much thicker and stronger fresh from  a real Man.”

“Yes Miss, thank You Miss.” I had answered naively not realizing what She meant. It was shortly after that that Mistress and Her friend had started my fellatio training. Although until that point I had lost my oral and anal virginity to Mistress, there was still all that to come, or cum, with the Sirs before I was pink pantied.

And in fact when Mistress had first decided to take a lengthy vacation, I was fully pink pantied by then, and nearly fully feminized. Although I was still to be snipped and to grow small breasts under my uniform. When I was sent to the sissy hotel, where I was  to serve as a sissy chambermaid whilst Mistress was away.

Mistress had teased me that the sissies chambermaids  spend so much time on their knees and swallow so much real cum and testosterone. That the house Misses very generously give the sissies their own pee to counter this with their own female hormones. To drink in glasses at room temperature of course, rather

than hot and direct from Mistress as at home. This is not really true of course as we are on a regime of very strong hormones and estrogen and our dildo and chastity cages are infused with strong estrogen. The pee myth is just to tease us, not that empty headed sissies know any better. And that sissy should be very submissive and grateful to the Misses for this kindness. And do their very best to earn good tips, from intimate services, for the owner of the hotel, the house Misses and Mistress to share.

Of course there is no fear of that not being the case as on arrival, usually in small groups the sissies are given the hotel uniforms to wear, tight glossy, wet look satin maids uniforms. And then taken out and paraded for the guests. The new maids have to 

each of the guests present and offer Her domestic and intimate services to each in turn. Sometimes rather embarrassingly the Sir might already have a maid between His knees when I introduce myself but that didn’t seem to spoil His enjoyment of her service or of my blushing introduction.

The chambermaid debutantes, so to speak, spend most of the afternoon swallowing cum and with sticky panties. On the first afternoon even extremely healthy tips are earned. As do they spend most afternoons, mornings evenings and nights. In between chambermaid & hotel duties. The Misses do seem to enjoy bossing and hurrying us a round with the aptly named very springy stinging hurry crops. And on occasion, though very rarely we might see the hotel owner, although only Her own sissies, who also serve as chambermaids are ever permitted to attend Her. There are female guests too but most sissies are not permitted to serve them intimately, although we do perform domestic and laundry duties. Mistress has teased me that because I loved hand washing Her panties so much I would enjoy hand washing all the other Ladies panties as part of my duties. In fact part of the ‘pleasure’ in the laundry room was that in the mornings at least one or two of the guests would come in and push one of the sissies face down into a mound of still to washed panties. Pull her panties down to gag her with,

then penetrate sissy, in front of all the other maids who would have to keep on working dutifully, the Misses would usually come and watch too. To add to sissies humiliation She would serve the misses and the male guest coffee afterwards before being dismissed, back to her pile of panties .

As such the atmosphere in the stuffy laundry room, was always one of expectant sexual excitement, even though we didn’t dare admit this even to ourselves, and fright, sex and fear. 

The sissies boarding actually pays for itself with the guest paying premium fees for the luxurious hotel and service, And generous tips for the intimate service of the sissies making a nice profit to be shared. The sissies should always bear this is in mind while being permitted the privilege of serving and pleasing the male guests. Grateful that their superiors will be enjoying holidays of their own and luxuries with the tips earned. When we return home we are given a tiny pink leather handbag no bigger than a purse, containing a receipt of the breakdown all our tips and Mistresses share. The purse is locked and only Mistress opens it after we hand over our ‘pin money’ to Her.

We are teased that an additional benefit accrued from the experience of serving all those different Men and sharing experience and techniques with the other sissies. When the sissies are allowed to chatter, sometimes when working they are limited in the topics permitted, to serving their Mistress, domestic service and serving the Sirs as well as their own little slave girl fantasy stories. A well trained and subjugated maid has little room in her, pretty head for anything else anyway, even though she is also an air headed little bimbo too. So that when sissy returns to her owner house sissy will be able to please her own Mistresses boyfriends and male guests with all the new tricks she has learnt. Which is lovely for her, as she wants to be a good girl or good maid for her superiors especially during sex, but more importantly for Him and His sexual enjoyment of course.  And for Mistress the cunnilingus is fantastic for the next week or so.

“Ah yes.” Mistress sighed happily thinking about Her vacation and Her welcome home.

I glanced down seeing Her wiggle excitedly which made me suddenly even more aroused.

“More wine sissy.”

“Yes Mistress, thank You Mistress.” I curtsied

“And lots more lip gloss sissy my boyfriend will be here soon sissy.”

“Yes Miss, thank You Miss.”

Mistress also increased the size of my dildo. It was so engorged now So I felt like it was throbbing and I was about to burst.

“Nice and squirmy sissy, so you will mince & squelch prettily for Him.”

“Yes Mistress, thank You Mistress.” I curtsied feeling myself squidge and squelch wetly.

“So sweet, I could fuck you myself sissy.” Miss said.

“But I will just have to settle for gagging you with my, I must quite frankly say soaked panties when my boyfriend fucks you, sissy.”

“Yes Miss, thank You Miss.”

“Are you getting a little exited in that tiny chastity cage sissy,” Miss teased

“Oh that is very flattering sissy, but you can fetch the canes later sissy.” Mistress said.

“Yes Mistress, thank You Mistress.” I gulped &

curtsied, knowing that Mistress was aroused Herself and would be even more aroused caning me before and afterwards.

“Life is just so wonderful, especially my sex life.” Mistress said happily,

“Yes Mistress, thank You Mistress.”

I love you Mistress, curtsy xx