When Sir cums sissies swallow obediently (with permission of course)

 

Mistress and Her best friend, & Sir were having drinks one afternoon, when Miss asked me if I thought it was time I learned how to please a real Man.

I had blushed and flustered with embarrassment looked at Mistress much to Her amusement.

Miss continued, that especially since I couldn’t take my eyes of Sirs erection when he came round. And especially since I kept teasing Sir with my shiny lip gloss. She  enquired coolly.

And especially as I always stood close to where Sir was sitting when He was visiting. Mistress & Miss had told me, that whenever there was a real man in the room I should stand near Him ready to serve Him.

“Please Mistress, no Mistress.’ I had begged

I was told to fetch Mistresses crop.

Then I was bent over Miss’s lap face down on Her leather skirted lap while Miss locked my wrist in the pink leather belt and cuffs, holding my wrists against my back.

Mistress often used the cuffs when caning me, or if I was between Her thighs and She wanted my hands locked out of the way.

Mistress had stuffed a pair of Her soiled panties in my mouth and I was given 6 severe lashes with the crop.

My rear was burning with pain. Sobbing and in tears I curtsied to Mistress and kissing the leather tab of the crop thanked Her for keeping me under strict discipline.

Then I was asked again.

Sobbing in pain through my tears I replied.

‘Yes Miss, Yes Mistress, thank You Miss, thank You Mistress.’

‘That’s better  Sissy, now curtsy to Sir and ask Him if He wants to let you please Him.

I curtsied awkwardly, still locked in the cuffs set.

‘Please Sir would you like sissy to please you Sir ?’

He looked down at me then told me to get across Hip lap.

Then pulled my panties partially down He spanked me hard until I was sobbing again.

He unlocked my cuffs and I was sent to fetch Him a cold beer and the Ladies fresh wine.

‘Maybe next time sissy.’ He told me curtly

‘Yes Sir, thank You Sir’ I blurted partially in relief and partially in humiliation

I was sent back to my chores, I could hear them laughing as I worked in the kitchen.

That night Mistress told me that if She is ever going to milk me again I would have to please Sir and other real men first.

And that the next time I hesitated I would be cropped again. Not only that but I would have to show Sir that I really wanted to please Him and strive to maximize his enjoyment. The crop will be an excellent tutor for you sissy She told me.

Then I was told to fetch the pink cushion and remove Her panties.

She was very hot and wet tonight and very loud when She climaxed.

The next time Sir came round with Miss I had to curtsy and to beg to be allowed to please Him.

Mistress cropped me again because I wasn’t effeminate and submissive enough in my pleading.

Sir had put me in the cuffs & over his lap again and spanked me.

I was always to be spanked or paddled before oral sex with a real man, it was to put me in my place under His discipline to serve His pleasure.

I was then sent to fetch Him  a bottle of beer and Mistress & Miss more wine, put back in the cuffs.

Sir pushed me to my knees in front of Him, then opened His trousers.

His erection was in my face as I looked up at Him. The smell of him and the warmth coming from his manhood dominating my other senses.

He was very big and hard especially looking up at Him with His erection right in my face.

I felt so tiny and soft in my cage. Mistress increased the size of my plug so it felt like it was filling me up and almost splitting my bottom cheeks.

I was told to kiss and lick Him slowly.

As my lips touched the crown of his glans the taste of Him was sickeningly fleshy and overwhelming. I felt like I was about to throw up at any moment.

“Look up at Sir, sissy let Him see that you want to please Him.’

‘Yes Mistress, thank You Mistress.’

I wanted to look anywhere else but up into His eyes, as He looked down at me expectantly, and expecting to be obeyed.

‘Suck His head in and out sissy, slowly and bob your head  deeper with each suck.’

‘Yes Mistress, thank You Mistress.’

He felt even bigger inside my mouth as I my head bobbed and the motion pressed my lips wider and wider.

I heard him sigh and smile. Then a hot spurt of precum in my mouth.

He pulled out of my mouth briefly

‘A little treat for you sissy.’ Mistress said

Sir and Miss both laughed.

Sir took a swig of his beer and said ‘You may swallow that little pretaste sissy’

I gulped and swallowed the precum ‘Yes Sir Thank you Sir.’

Then He pushed back between my lips forcefully and seized a fistful of my hair as He pushed deep into my mouth.

I was panicking and choking. He ignored my gagging and pressed deep until I could feel Him in the back of my throat. Mistress had been training me to overcome my gag reflex with Her strap on but having a real man push his throbbing pulsing manhood so deep and powerfully into my mouth penetrating me, was completely different.

“Suck him tightly and bob your pretty little head back and forth sissy.’

Mistress had taught me, using the strapon, that the best way to overcome the gag reflex was to swallow as He pushed. The swallowing was extremely pleasurable for Him. And just pulled Him deeper and deep and excited Him so he increased His the tempo of His thrusting .

‘Look up at Sir, sissy, let Him see how much You want Him to cum in your mouth.’

I struggled to look up at Him all I could see was His stomach and feel His manscaped but still hairy balls on my chin. With each swallow He thrust still  harder & deeper forcing me to gag and splutter and swallow Him deeper.

Then with a final push and groan of pleasure He exploded in my mouth. Spurting and thrusting filling my mouth with his thick sticky cum.

When he had finally finished spurting into my mouth and pulled out from my lips.

I had to suck lick the remaining semen from His meatus until He was totally clean  

Mistress said ‘Open your mouth sissy’

I opened my mouth

‘What a lovely thick load sissy, what a treat for you.’

‘Do not spit sissy and do not swallow until Sir gives you permission.’ Mistress said.

I looked up Her unable to speak with my mouth full of Sir cum

I waited on my knees with my mouth full looking up at Him while Sir fastened His trousers and sat back relaxed, chatting with Miss & Mistress.

Then after a few minutes He said ‘You may swallow sissy’

It took me two sticky gulps

‘Remember to say thank you sissy.’ Mistress told me.

‘Yes Mistress, thank You Mistress.’

‘Yes Sir, thank You Sir.’

‘Tell Sir how much you enjoyed tasting His manly cum sissy.’

‘Yes Mistress, thank You Mistress.’

‘Thank you Sir,  For allowing sissy to please You Sir and to swallow your Your cum Sir. It is so sticky, thick and manly Sir, Thank You Sir.’

‘The pleasure was all mine sissy.’ He laughed patting my head.

‘See sissy I told you a real mans cum is so much thicker and creamier, especially when its hot and fresh sissy.’ Miss told me with evident amusement.

‘Yes Miss, thank You Miss.’

‘So much better that your pathetic thin leaks sissy.’ Mistress told me

‘Yes Mistress, thank You Mistress.’

‘Fetch Sir a fresh beer sissy and wine for us  sissy.’

‘Yes Mistress, thank You Mistress.’

I brought them fresh drinks with a curtsy.

‘Hurry along back to your little chores now sissy.’

‘Yes Mistress, thank You Mistress.’ I curtsied.

Sir slapped my bottom loudly as I turned to leave.

‘Thank You Sir.’ I squealed as he always managed to hit the base of my plug.

That evening Mistress told me to fetch the pink cushion, She was very excited tonight. After She had climaxed with multiple orgasms, She kept me between Her wet thighs kissing Her lovingly, as we talked.

Next time Sir came over I was to flirt, coquettishly and stay close to Sir. I was to ask to please Him and He would always put me over his knees and spank me before fellatio.

He was always to cum in my mouth and never all over my face, that was Mistresses preference, and while I was sucking Him I was to squirm & grind on my plug as I sucked. Keeping the rhythm, just as i did when i was between Mistresses thighs kissing Her intimately. And although my performance had been adequate today I was expected to improve greatly and excel so that Sir would want lots of oral pleasure.

‘Dress me for bed now sissy and when you have your little nightie on you can please me again. I do so love watching you on your knees before a real man.’

‘Yes Mistress, thank You Mistress.’

The next time Miss came round She had a present for me. A wide pink leather paddle. With a raised detail of little lovehearts and pursed lips. For when Sir didn’t want to spank me.

Sir was a regular visitor but even more humiliating was when Mistress started having Her own boyfriend over for drinks before they went out together. One evening Mistress told me to get between his knees and please Him, while She was getting ready. That way he wouldn’t  be horny all evening when they were out.  After that first time Mistresses boyfriend would often collect Her from home and enjoy my oral service.

Although Mistress had told me I would only be milked again only after I had learned to please a real Man properly I was still waiting and desperately waiting to be milked again 3 months later.

Mistress also gave Her boyfriend and Sir a copy of the key for my chastity devive. It was only proper, She said, that if I was to please them they should know that I was properly locked up.

Although Mistress had told me I would only be milked again only after I had learned to please a real Man properly I was still waiting and desperately waiting to be milked again 3 months later. Mistress enjoyed teasing me saying it would be that day then postponing it at the last minute, or bringing Sir or Her boyfriend round and telling me it was much more important that Sir came then my little leak.

Even though I knew I wouldn’t be allowed to cum, after 3 months so needy, emotional & tearful all the time that Mistress said it was like I was on my sissy period permanently.

Mistress said that it was quite lovely for me to be so vulnerable, submissive and attentive.