5. A Sissies Journey - Milked & Caned

 

The Ladies in the office were also less than sympathetic. They delighted in either perching me on the corner of their desks and teasing all the details out of me. Or sitting on my desk area, not that I ever did much sitting there,  suggestively close to hear every little detail.

Was He big sissy ? Did He cum a lot sissy ? Was Sir pleased ? Did you moan and sob prettily ? Did you struggle feebly and sweetly ? Did you swell pathetically  in your little chastity sissy ? Or did you get even tinier ? Sometimes when a Man is fucking you, or if you are sucking Him, you feel yourself swelling in the chastity tube & sometimes you feel incredibly tiny and soft. It must have been so lovely for you sissy pleasing a real Man like that ? And so sweet not knowing who your first was. Especially serving drinks and performing fellatio afterwards. Question after question and teasing me mercilessly.

That evening Miss had taken me home with Her before taking me to the club as usual and Her boyfriend had put me on my knees for fellatio while She was getting ready. I had never performed oral outside of the club before. Her sissy looked very squirmy and jealous performing her housework while I pleased Sir. I must confess I was secretly very pleased seeing her gagged at her chores while I made Sir cum. Miss was very amused but soon grew tired of it. The next evening Sir had us both on our knees begging to be allowed to be the one to suck His cock.

Miss exasperated had finally said

“For heavens sake just fuck one of the bimbos, and let me concentrate on getting ready.”

We were both caned and severely so afterwards. I did get a mouth & faceful of Sirs cum though, sissy

was positively squirming with envy. But then on another night sissy got to please Miss before we went to the club, and it was my turn to be very hot and jealous. This very petty rivalry and feeble vying for attention, was very effeminate and apt for sissies, under strict domination and discipline. And quite ruthlessly exploited by our superiors for their enjoyment and amused disdain. We felt both degraded and demeaned by our own jealous behavior yet gratified if we were chosen. Our superiors would play us off against each other relentlessly, teasing one then choosing the other, gagging us with each other panties, cleaning Sir or Miss after the other had pleased Him or Her intimately. Punishing one or both for the failings of the other. And we shamefully ached with hot need, powerless and in tears to be pleasing to be found to be pleasing, and more pleasing than the other, pathetic.

And at the club Ms knew so too, as Miss would delighted in telling Her, in front of me and then She deliberately not choosing to enjoy my tongue that evening. Instead I attended and served drinks while another sissy served Her intimately.

Now on the long hot evenings in the club I would be taken to the rooms regularly for fellatio and anal, sometimes by groups of men, but often just one Sir. That same hot effeminate jealousy, when another sissy was taken to one of the rooms, even for a gang bang, when another sissy got a slap on the bottom, or fondled rudely.  

We were sent to the rooms more than few times per night, the Sirs were very horny and often quite insatiable. For me and the other maids hurrying fearfully and serving with my face and panties hot and sticky most evenings. Ostensibly my uniform and appearance, spotlessly immaculately neat and tidy, sissy clean. On many nights Ms only called me occasionally to a room herself and some nights I didn’t attend or serve Her, or sometimes She didn’t come into the club at all.

Then one night She announced that because I was now fully pink pantied and was progressing learning how to please Men properly I would be allowed a little occasional release. As a little extra reward, She told me teasingly. The real reward for sissies in Her eyes was pleasing the Sirs and swallowing all their manly cum.

My head was swimming with silly fantasies and questions, could I still get firm outside of the chastity tube. Would we have sex ? Or would I just be allowed to masturbate ? Would She get on top, or would She just masturbate me ? How would it feel after so long ? would it be nice and powerful.

He next night She summoned me into one of the larger rooms and She and a few of the other Ladies were already sat there drinking champagne. Ms and the doctor were there and both were dressed in latex nurses uniforms, Ms in while, like an angel with Her blonde hair, and the doctor too in crimson latex. I was so pleased and flattered thinking that Ms was doing that to make my release even  more special for me. I later found out that Ms, the doctor and the other Ladies were going to a sexy fancy dress party  at another club. And the other Ladies were not dressed yet. Apparently there were lots of new sissies at the party who were going to get locked in chastity and pegged for the very first time.  

I had helped the other sissy serve fresh drinks then I was pushed down  over the padded bench. My

panties were pulled down, but not all the way to my ankles like the Sirs liked, or Ms liked when She was pegging me, just lowered. To my delight my chastity cage was unlocked then removed, but then to my surprise and dismay replaced quickly and expertly with an even tinier tube. The device still covered my cherries and had the urethral insert but was considerably smaller.

“Don’t fret sissy, your next tube will be much more petite and even prettier.”

In fact the next device would keep my cherries up and inside my body cavity, out of the way. Leaving just the tiny pink silicon chastity tube, nub really, and its lock visible.

“Yes Miss, thank You Miss.”

“Not that anyone will want to see it much sissy but it will be pretty for Sir and me.”

“Yes Miss, thank You Miss.” I blushed.

I watched in the mirror as She snapped on a pair of glossy white latex gloves. Heard the scary snap of the gloves as I watched Her in the mirror over my back just behind my trembling bottom. In the mirror I could also see that  some of the Ladies were watching amused but most were just enjoying the champagne and chatting. I was very much a side event. Ms later told me She was considering postponing but thought my milking would be amusing and set the tone for the party afterwards. The wet lube on Her already glossy white latex gloves was somehow even sexier than it was on black latex, I squirmed with arousal confined so perfectly in the tiny chastity tube. She pulled out my dildo with a loud wet embarrassing slurp and Her finger pressed inside me. The lubed glove felt cold then warmed up sensuously inside me, pressing Her fingertip up on my prostrate, rubbing it firmly, but steadily, so that I never felt any build up or excitement, it really just felt just very invasive. In the mirror I could see Ms and some of  the other Ladies, paying a little more attention now,  watching and enjoying the spectacle. Then after a minute or so I felt a very faint dribbling sensation that went on for a short while. And She pulled Her finger out and pushed the dildo back in place.

“All done sissy.” She announced. “More wine sissy.”

I was in tears

“What did you expect sissy ? Only real Men get to cum not sissies.” She said sweetly but patronizingly and patted my bottom.

“And only I get to orgasm with you sissy.” She said handing me the gloves still glistening and slick  with lube.

“Yes Miss, thank You Miss.” I curtsied, I was still so desperately hot and horny, so attentive and obedient. And incredibly even more so now.

“And you do have a little drink as a treat sissy.” She said holding up a small wine glass half filled with weak looking precum.

It even tasted weak and a little sour.

“But don’t worry and never mind sissy at least you can suck one of the real Men later and He will taste so much better, than your little squirt.”

“Yes Miss, thank You Miss.” I curtsied.

“and you can go back to the club now sissy.”

“Yes Miss, thank You Miss.”

After they left for the party, She didn’t say goodnight incidentally, She didn’t come back that evening,

nor for the next couple of nights. But when She did come to the club a couple of days later I was summoned to Her room late that evening. She had caned me for looking so disappointed after my milking and put me between Her thighs for a fast and quite furious licking. She was pressing and thrusting on my face while I struggled to maintain a pleasing firm rhythm with my tongue. Then She put me between Her thighs again for a much longer slower orgasm, which was much more intense with multiple waves of blissful climax for Her. I got to hand wash Her panties after She left. It was nearly time for my taxi home, I would iron the black silk panties for Her tomorrow.

The next night She showed me some photos and videos of the party. On a few of the pictures there was several sissies lined up and bent at the waist in some sort of stocks, in a row. Panties down and bottoms bright red from the paddle, you could tell it was the paddle because  their tight little bottoms although puffy and inflamed didn’t show any cane lines. Usually Ms and the other Ladies prefer canes or crops, leaving spanking and paddles to the Sirs, but this was a party and the sissies were very new. They all clearly had well lubed bottoms ready for pegging. Ms showed me a

video of a line of sissies getting pegged multiple times by several different Ladies. While other Ladies in various very suggestive fancy dress costumes, laughing and drinking mainly champagne. Having a merry time served by the sissies who weren’t currently being pegged. All the Ladies appeared to be having a good time, quite tipsy and merry but in control. I so longed to be there but only to get pegged by Ms. Ms incidentally reserved my pegging and cunnilingus just for herself. There was another video of a couple of the sissies being caned later and them all curtsying after cleaning the club and thanking the Ladies sweetly for a lovely evening. Ms laughing pointing out how gingerly the sissies were mincing now as they curtsied and cleaned up, as She fondled and patted my bottom quite affectionately.

 

Now I was pink pantied Ms also started to keep me penetrated new a new estrogen  infused silicon dildo on me, as well as estrogen it was infused with lube that kept me feeling very tight, much tighter even than my very first time but so slippery for Ms’s strap on the Sirs cock. And made me squelch and squirm even more as I  tottered about on my platform heeled maids booties. Like my chastity the dildo plug was locked too only the superiors could remove it. Although unlike the chastity tube which was never unlocked, my ass  would be regularly for my superiors pleasure. It was 10” and 2.2” in diameter, for my normal day to day duties, but through auto suggestion could be made to feel bigger, bigger when performing fellatio or domestically serving Ladies and much bigger 12-14” when serving Ms intimately. Because it was locked my ‘sissy erection’ as Ms called the phallus  also seemed to feel much thicker and stiffer. And because of the estrogen lube and hormones my bottom felt like I was squeezing and squelching along the whole shaft tightly, grinding,  and trying feebly to clench my muscles around the shaft in fright and embarrassment. It had very much the same effect as very large kegel balls, making me feel so tight but slippery and smooth for Sir or Ms. I would moan and whimper so helplessly and sweetly when being enjoyed anally, usually gagged with my or Ms’s panties.

Effeminized and sissified pink pantied sealed by the Sirs cum in my mouth and ass, and by swallowing
my own weak tiny mess. I was never to be milked again. Ms decided my last dribble was so pathetic it
was barely worth the mess. And in case denying me that too made me even more desperate to please and devotedly attentive to Her. So much so that it was necessary in Her opinion and amusing to cane me for being too attentive and needy. And enjoyable for Her.