Deflowering sissy maid

 

Mistress still hadn’t milked me again more than 3 months later and Her boyfriend & Miss’s Sir were now coming over regularly for oral sex before they went out.

I had to call all real men Sir.

Mistress told me that soon Her boyfriend would soon be stopping overnight & when he did I would be waking him up with my soft lips.

‘Wont that be  a lovely way to start your day sissy ?’

‘Yes Miss, thank You Miss.’ I replied haplessly, almost in tears.

‘Do you want to go and fetch my crop sissy ?’

‘No Miss, Yes Miss, please no Miss.’

‘Well show a lot more eagerness then sissy.’

‘Yes Miss, thank You Miss.’

‘In fact you may go fetch my crop anyway sissy.’

‘Yes Miss, thank You Miss.’ I had sobbed.

One afternoon Mistresses boyfriend, came round even earlier and Miss came round too.

After Sir had cum and He had given me permission to swallow, Mistress said. ‘I think Sir wants that tight little ass you have been teasing Him with sissy.’

I looked round horrified, I was still in the cuffs and my mouth was still sticky with His cum.

I opened my mouth to demur, feebly, but I couldn’t speak and Mistress took Her panties off and stuffed them into my mouth. They were very damp, quite soaked in fact.

‘I think Sir will love your little pink sissy pussy wont He sissy.’

Mistress had, insisted that I had my anus bleached and coloured pink, for when She started pegging me

I had looked at them in tears of humiliation gagged and muffled into silence as I was.

‘Take sissy to Her little room, you can fuck spread that tight little ass of hers in there.’ Mistress said.

“That way she will think about  you when she goes to sleep at night, or your nice big cock at least.’ Miss said

Open handed Sir slapped my bottom and the backs of my thighs to hurry me along. I could tell He was quite eager and excited . Almost as much as  I was quite flustered and numb with fright.

In my room Sir pushed me down face down on my bed, onto my glossy satin sheets and pulled my panties slightly down and slapped my bottom again.

My buttplug was unlocked and removed and with another slap He started pushing inside me.

The more I tied to push back and wriggle free. Crying and whimpering into the panties gagging me. The harder He just pushed me face down onto the bed, enjoying my struggling.

‘Sometimes they moan and whine, just ignore them.’ I heard Mistress say.

 ‘She never learns, she struggles just a sweetly, when I’m pegging her. The more she does the more I enjoy  it.’ Mistress said

‘Oh they never do, my sissy is just as pathetic.’ Miss laughed.

Then Sir started breathing and thrusting very quickly. The panties in my mouth choking me as I struggled to pant for breath.

He exploded inside me massively, I felt like He had suddenly filled me up completely with His cum as He lay on my back breathing heavily.

Mistress later told me it was very sweet that I felt like real men  always came so massively, in my bottom or my mouth, even though it was just a little more than average. It was obviously so much more than I could manage if I was ever allowed. And it showed that I wanted to please Sir and was thinking about His pleasure. 

As Sir pulled out He pushed my butt plug back in and locked it in place.

I was pushed  down onto my knees and His sticky still swollen manhood was pushed into my face.

Mistress pulled Her panties from my mouth and put tossed them aside nonchalantly. ‘Lick Sir clean sissy.’

‘Yes Mistress, thank You Mistress.’ I whispered still gasping ‘Yes Sir thank You Sir.’ I was suddenly very glad of the hot enema that Mistress made me have every day.

As I was licking Sir He suddenly had a spasm and a last spurt of cum, shot into my mouth.

“Oh look sissy another little treat for you.’ Miss laughed.

After I had finished licking Sir clean we went downstairs and I served my superiors fresh drinks, then I was dismissed back to my chores.

Miss had commented on my squelch and mince of shame, as I curtsied and hurried away.

‘Yes Miss, thank you Miss.’

‘Hurry along now sissy.’

‘Yes Miss, thank you Miss.’

‘Sticky panties sissy.’

‘Yes Miss, thank you Miss.’

They had all laughed as I blushed and squirmed, then curtsied again and left the room.

Later I was told to start preparing snacks and drinks for a little party this evening.

When Miss & Sir  had left in the late afternoon Mistress had thankfully allowed me to change my sticky panties and clean my myself and my uniform.

Mistress had laughed about me squelching and mincing about with my sticky knickers, saying how She always enjoyed leaving me in sticky panties after a pegging but a real mans cum is so much more intimate and humiliating for me.

Just before the evening & just before I dressed Mistress for the party. I had been given a new set of panties to wear in the future these were now pale pink. I didn’t realize it but this meant that real men visitors  would know that I was there to please them fully if they wanted it, which they usually would.

I was allowed to keep the panties I had been wearing unwashed but folded carefully in my pantie drawer.

That evening Mistress organized a little party to celebrate the taking of my virginity. We hadn’t really celebrated the first time Mistress pegged me, or the first time I had orally pleased Sir, Mistress had had  a drink with Her friends naturally.  But this was a special celebration, She told me. I was now Her fully effeminized  sissy and there was no going back.

She also later told me that, that after today, She would not be indulging the messy pointless business of milking me. Instead my anxious desire and denied need for release or milking would continue to keep me in a constantly submissive and attentive frame of mind. Meaning that I would serve Her and Her friends so much better, and so much better intimately.

Not only that but She had noticed the tiny leaks I had when I was squelching on my dildo, when I was between Her thighs or on my knees before Sir and that was more than enough, even though I never felt the slightest thing, until I noticed the very faint wet patch. And She would decide whether or not She wanted to punish me for such infractions and nocturnal infractions according to Her whim at the time.

The party was for Her and Her friends. I was as you would expect just there as Her sissymaid serving drinks. None of the guest spoke much to me except to order me to fetch fresh drinks or to comment on how sweetly I minced now, now that I had, had a real man inside me. There were a lot of pats on my bottom too, and smirking comments on my pretty pink panties.

I had been so helplessly hot, needy and and tearful for Mistress after Sir & Miss had left. And although none of ladies at the party wore anything particularly exciting by their standards at least. I couldn’t help but be totally and helpless aroused and frustrated just to see them and be in their presence. I had confessed this to Mistress, fearfully expecting to be punished, but She had laughed saying that was only natural now, that I had been penetrated. The further I was away from having real sex , as a man or boy, the more I would be unable to control my feelings of arousal.

 

I had been a little surprised that Mistress didnt send me for the pink cushion earlier because although I could tell She was very aroused. She said She could orgasm at  any time & when She felt like it. So She was savouring Her enjoyment.

That night though after all the guests had gone She was very demanding & rampart She came several times with multiple orgasms, and the next morning too.

Not only did the aftermath of having a real man inside me make Her very horny, but it also made my intimate service so much devoted and hotter somehow She said.

The next day Miss brought Her boyfriend round and He fucked me too. He didn’t take me to my bedroom though but into the laundry room and used me on top of all the clean laundry which I then had to clean all over again.

Mistress had told Her male friends not to worry about my struggling and protests. It wasn’t coercion or rape because She allowed and enjoyed my forced service. Besides which effortlessly overwhelming my feeble struggling added to the enjoyment.

My wants & needs, or my protests & objections were completely unimportant compared to Her wishes and Her enjoyment, and the enjoyment of Her male guests.

Miss was always teasing me about my curtsy and how I would smooth my apron prettily down in front of me after I straightened up. My fingertips would stop, just for an instant  at the very slight bulge of my chastity cage, then I would continue. Miss said it was very cute & that if I were Her sissy I would be hurrying to fetch Her strap on very frequently indeed. This made me blush every time I did it after that, which delighted Miss & Mistress and embarrassed me even more.

Miss said that Her boyfriend thought that my curtsy was very cute too, but that seeing me hesitate and squirm when my fingers brushed my cage made him think about fellatio first. It was watching me bend over, and exposing my bottom, as Mistress had insisted I do,  to serve drinks, that made him want to bend me over for other purposes.

Mistress told Her that I fetched the strap on quite a lot with Her anyway. And Miss said, the strap on or Her crop, as I was so cute, too cute not to be kept under strict discipline. Mistress said She agreed with that too. Although Mistress usually preferred, but not at all exclusively, Her canes. 

Mistress and Miss constantly teased me about the way I would squirm and visibly tighten my bottom on my plug in whenever a real man was mentioned. Just the thought of such a visit made me feel flustered, totally vulnerable and defenseless. They said it just showed how excited I was to please a real man, like a good sissy should be. And just think how lovely it will be when Mistresses other friends brought their boyfriends round, to see my pink panties.

After I had served them snacks and drinks I had been dismissed to my housework. I could still hear their laughter and amusement ringing in my ears. 

Mistress nearly always hurriedly sent me for the pink cushion after one of the Sirs had finished with me and left