The Session

I arrive at the door of the hotel room, at the stated time. My feelings were mixed. Nervous, meeting you for the first time and excitement knowing that I would be in control of the situation, well at least for the moment. Just before the door opens I realise I will not recognise you! The only pictures I have seen of you, you are wearing a hood! The door opens just a crack and I see your made up face, you smile, fully open the door and usher me in. Nervously you curtsy.

"Hello Sissy Poppy" I murmur taking in your attire. Black six inch patent leather shoes, black fishnet stocking, a very tight, form fitting black PVC maid's dress, the hem of which is held out almost horizontal by the ruffles of lace petticoats underneath. I can see the edge of the frilly Basque you have on underneath and the false tits filling it. The outfit is finished off with White lace gloves. You are fully made up your hair hanging in large curls to your shoulders.

"You look fantastic" I breathe taking in your shapely form.

"Turn around" I ask. Smiling you perform a pirouette.

"Lift your skirt" I demand.

"Pink...sweet" I smirk.

"Are you erect?" I ask.

"Yes Master" You simper.

"Wow you are small *Laugh* I can hardly tell" You turn bright red, but the twitching of you cock lets me know you love the verbal humiliation.

"I have a present for you" With that I produce a bright pink collar, it has a pink heart shaped tag at the front with the words "Sissy Poppy" picked out in gold letters. You bow you head allowing me to fasten the collar around your neck. With a snap the tiny padlock secures it permanently in place.

"What's on your mind Sissy Poppy? Where is the key?" I smile. I look at my watch and realise that we have to go.

"Come on sissy let's go, the taxi will be here soon".

Your eyes open wide.

"Taxi! What do you mean? I was instructed to wait here.........for my Master.....you!" You state.

"Yes, and I was instructed to pick you up and meet the taxi outside in ten minutes" I state.

I can see the fear in your eyes and my erection hardens, this is a new feeling. The power over another person is very arousing. Despite your fears you follow me out into the corridor and we make our way to the lift.

"What are you doing Sissy Poppy?" I demand. You look questioning at me.

"A Sissy walks behind her master" You blush but fall behind.

We manage the corridor and the lift without meeting anyone but the lobby is another matter. Heads turn, men sneer and women tut and you my pretty sissy blush an even deeper red. I must point out my attire at this time, I am wearing black shoes, black trousers and jacket, white shirt with a black tie. Very conservative, and totally at odds with your attire. I smile at this thought.

"Hurry Sissy" I state loudly, getting a few laughs.

"Or do you want to miss our taxi and have to stand waiting for another?" You quicken your pace in answer.

The taxi is waiting and I can hear you sigh as I open the door for you. Once we are in the tax offi it heads with no instruction. Obviously it was pre-booked. Through the journey you sit with your head bowed next to me. I know you are battling with mixed emotions. Why did you let me humiliate you in this way? And the biggest question...........why does it turn you on so much you want more? We arrive some half an hour later outside a grand house. Out of the taxi he quickly drives away and I'm sure he called us freaks. I walk down the path and you follow at a submissive distance. The door is opened by a maid and we are welcomed inside.

"Mistress Elaine is waiting second door on the right" directs the maid.

At the door I knock and a strict demanding female voice bids us enter.

Mistress Elaine is a vision. She is the Mistress I would choose, she is my dream Mistress. A BBW, and dressed head to foot in leather. I stand in awe marvelling at her. Black patent leather thigh length boots encase her legs, a black leather leotard covers her ample body except her tits which are thrust obscenely through holes in the front. Her arms are encased in leather gloves. She stands smirking at my shocked stare.

"OK slave I think you have seen enough, time to play. Take off your clothes" she orders.

As I step into the room she notices you.

"Ahh what do we have here your Sissy maid? Ohh I do like the collar....Sissy Poppy...sweet".

You blush and curtsy eliciting a laugh from our Mistress. Once undressed she orders me to stand alongside you.

"Take off your knickers Sissy, you won't need them...then lift your skirt" she orders

"Well I can see why you are the masterful one" she points at me with a smirk.

"But you are only just bigger than your sissy...just think but for half a centimetre you could have been standing here in your sissy outfit.....no doubt you have one."

We both stand before our Mistress, our faces burning red with humiliation, our tiny cocks throbbing with the thrill of it. She moves over to a chair and sits.

"Time you insignificant wretches worshipped my boots" she points to her feet and we both cross the room and kneel before her. I begin the worship of her right boot you begin on her left. As we progress up Mistresses legs we glance across at each other, you smile, I wink and both our cocks throb.

"Enough........Slave would you like to suck my tits?" She asks.

"Yes please Mistress" I quickly answer.

"It does of course mean punishment" she states.

"Yes anything to touch your wonderful body" I breathe.

"And it won't be you it will be your Sissy who gets the punishment"

"My answer is still Yes Mistress" I answer quickly.

Glancing across at you I see you looking hard at me. Yes I am to get the pleasure and you the pain, sweet humiliations. As you meet my gaze and think this thought your head drops in supplication.

"So quick to sacrifice your Sissy" she laughs.

"Up slave" Mistress commands as she offers me her right tit.

I kneel up and lean into Mistresses body, feeling the soft caress of the leather against my lower body. My cock throbs in anticipation. As I take her nipple in my mouth she sighs loudly and her head falls back. It seems her nipples are very sensitive. The nipple responds immediately growing to the size of a raspberry. I continue my ministrations eliciting gasps from Mistress when I use my teeth to softly rake her nub. Glancing across I see her twisting her left nipple so I switch to that side. As I do I glance down and see you watching intently, no doubt wishing it were you suckling on the ripe teats. As Mistresses left nipple erects in my mouth she gives a gasp.

"Suck harder...slave" she gasps.

I do as commanded and her breathing becomes more ragged. Soon she is moaning, and her chest heaves. Then with one big gasp Mistress climaxes. I slow my caress of her nipples as Mistress regains her composure.

"Not bad Slave.....but you are greedy...fifteen minutes sucking on my tits. That means fifteen strokes for Sissy".

I glance across to see your reaction but you kneel, head bowed like the good Sissy you are.

"I think the punishment will be a ball whipping.....get her ready slave....there is a cock and ball harness over there" she points to a table covered in retraining devices.

We both rise and go to the table.

"There is a smaller harness on the left" laughs Mistress.

You don't blush this time but I see you cock twitch. Is it the jibe or the thought that another man will be touching and restraining your cock and balls I wonder! I take the device and then take hold of your balls, you shudder. I fasten the first strap around your balls causing them to swell obscenely. The second strap fastens around the root of your cock, which means I have to take hold of it. You look up and stare longingly into my eyes. I shake my head, I know you so desperately want to cum, but we both know that would be disastrous so I quickly finish.

"Slave kneel on the floor all fours!" Mistress orders.

"Sissy on all fours behind him.....I want your nose in his arse crack, whilst I whip you" she smirks.

"And no licking! You slut!"

I hear the rustle as you get down on all fours then feel your nose nestles into my behind. I shudder with lust as I hear you breathe in my musky scent. I know what you're thinking. I know your cock is throbbing for release, because were the roles reversed I would be feeling the same, the joy of humiliation! Without any warning Mistress begins the punishment. Mistress uses a cat 'o' nine tails to flagellate you bulging balls. As the first stoke hits you yelp and your face rubs across my pink rosebud, your lips touch the forbidden area. Six strokes later and the temptation is too much. Your tongue snakes out and caresses my tight bud. I almost yelp in surprise, but just manage to control it. Now as you endure the whipping torture I endure your tongue caressing and teasing without groaning and letting Mistress know what you are doing, a punishable offence no doubt! All too soon your punishment and my sweet torture ends.

"Whipping a slave always gets me horny slave.........how would you like to lick my pussy?"

"Oh yes please Mistress. It would be an honour" I almost shout.

"Same rules apply....someone gets the punishment" She says with a smile, looking straight at you. You in return bow your head in resignation.

"Yes Mistress" I answer.

"Mmmmmm if you lick my pussy....then Sissy here will have to take a fucking...."

"Yes Mistress, I accept" I quickly sell your arse for my pleasure, I know you are both seething and lusting inside, the state of your cock and your trembling gives that away.

Mistress retires to a couch and lies out on her back. There is a whirring sound and her legs are slowly parted and her hips drop slightly. The couch is now in position for a slave to kneel before Mistress and worship her pussy. I take my position noticing as I do the zipper at the crutch.

"Use your teeth Slave.........You Sissy.......make me a drink. A gin and tonic....The bar is over there in the corner" she commands.

I take the metal tag of the zip between my teeth and pull down. As the zip slides down I am met with the heady scent of Mistresses excited pussy.......Bliss! The crutch seemed to be cleverly tailored because when the zip is fully down her pussy is laid bare giving easy access to my craving tongue. I immediately dive in, pushing my tongue in at the top to find the hard nub of her clitoris. I am rewarded with a contented sigh from Mistress.

"That's good slave" she murmured as she slid lower into the couch. As I look up I see you standing obediently alongside Mistress with her drink on a tray, you glance longingly at me.

My ministrations on her clitoris soon take effect and her breathing quickens, as I sense this I slow down and Mistress groans in frustration and pleasure.

Yessss Slave don't let me cum....keep me on the edge" she sighs.

I know she is very close so I switch to languidly lapping her pussy. The taste is exquisite and I groan in pleasure. Once again I move up to her clitoris and start the process again. I do this twice more before she can stand it no more and demands release. Her climax is hard and long and she howls her pleasure. Some minutes pass before her breathing returns to normal and as we wait you and I exchange glances. You stand there shaking with the exertion of holding out the tray not daring to put it down. I shake with the exertion of the long pleasuring of Mistresses pussy. I can see in your eyes that you long to be where I am and also the haunted look because you know what's coming next. Mistress finally leans across and takes the drink from the tray not even noting you existence.

"That was good Slave you have real talent....I suppose it makes up for your lack on manhood" she smirks. Lifting me up and then smashing me down and I love it I shiver in humiliation.

"So let's give Sissy the fucking she deserves.....Would you like to fuck her pussy slave?" Mistress asks.

"But Mist....." you start.

"Shut up Sissy! If you are a boy that dresses as a girl, then you deserve to be fucked like a girl.......Well Slave" she demands.

I look across at you, you stare back and shake your head slightly. I know your limits but I also know you want to push those limits but are you ready?

"No Mistress" I state and I see the relief in your eyes.

"Well tough, you will be" she commands.

I see you eyes widen as you realise what is about to happen.

"Sissy go fetch the bag of ice from the bar".

You quickly fetch it wondering why on earth it is needed.

"Now place it on Slaves crutch".

You step towards me and the look of puzzlement soon turns to one of glee as you place the bag against my cock and balls and I gasp with the cold. Once my erection has shrivelled Mistress hands you a leather restrainer.

"Quickly Sissy before the pervert gets hard again" she advises.

The restrainer is a complete cock and ball sheath which is secured at the root of my cock, you do this quickly. The top end of the sheath has a long strap which when pulled between my legs effectively pulls my cock and balls out of sight. This strap is then fastened to a waist belt.

"You didn't think you would get the pleasure of sex in my domain did you slave?" she smirked and I notice you doing the same. With that she produced an eight inch strap-on.

"Your cock is too small to give her a real fucking, but you will still be fucking her........Put this on him Sissy" She hands the strap-on to you. You kneel and strap the false cock over my restrained and frustrated cock. Once completed Mistress orders....

"Over the couch Sissy and lift your skirt".

You adopt the position presenting you cute bottom to my lusting gave. I step closer and Mistress hands me a tube of lubrication. I apply a large blob to your arse crack and you flinch at the cold. I massage the lubricant into your pussy, first with one finger...then two....then three. Once you are fully lubed I press the end of the strap-on against your tight puckered pussy. There is a slight resistance to start with then the head pops in. You utter a cry of pain, which changes to a groan as I slowly slide the full length into you. When my hips meet your bottom I stop. You shiver under me and it feels fantastic. I control you now and the feeling of power is an aphrodisiac. Slowly I withdraw, almost pulling out and I see you clench to keep the big intruder inside you. "You slut!" I think. I take up a steady rhythm and your groans quickly change from pain to pleasure. The head of the strap-on as it rubs over your sensitive prostrate sends a shiver through you on each stroke.

"Look up Sissy" commands Mistress.

As you do, so do I, our eyes meet in the mirror facing us. I see the lust on your face your loving this. You see the lust on my face I'm loving this! Then you smile and turn bright red as Mistress whispers in my ear.

"Make her cum Slave".

So I reach down and pull your shoulders up. We are now both standing facing the mirror. The strap-on is buried deep in your pussy.

"Lift up your skirt Sissy Poppy" I whisper in your ear.

You do so and as you do I reach round and begin to stroke your cock with my lubricated hand. Your eyes glaze over, your mouth becomes slack and you head towards climax. Your head drops back against my chest and to my surprise you begin to thrust back against the strap-on. I match your thrusts and with a wail of joy you shoot your cum all over the floor and my hand. As your climax subsides I withdraw from your pussy.

"Clean that up Sissy" orders Mistress.

You fall to your knees and begin to lick up your cum. Finished you look up at Mistress.

"Don't forget Slaves hand" she points out.

You lick the cum from my hand and then begin to salaciously suck on my fingers. I look down with raw lust in my eyes. My cock is aching in its tight prison.

"Getting some payback Sissy?" Mistress laughs.

"Well it seems Sissy has had all the fun.....time for slave to have some."

Mistress then proceeded to undo the strap holding my cock in place and it immediately springs forward.

"Up against the couch Slave and take hold of your tiny dick"

As I do this I see Mistress hand a wicked looking cane to Sissy Poppy.

"Now Slave for each stroke you can stroke your cock...understood Slave?"

"Yes Mistress".

"But only when Sissy tells you can you cum" she smirks and hands the cane to you.

She then places a blindfold on me.

Swish...........Crack! I stroke my cock, and immediately realise I am ready! In fact, I almost cum from the sting of the cane and the pent up emotion!

Swish............Crack! I stroke again and clench my free hand. What exquisite torture. I so much want to cum, every fibre of my body is shouting for release. You must have realised this because there is a long pause before the next stroke.

Swish............Crack! Fortunately my ardour has dropped so I manage to hang on. You notice this and increase the stroke rate, driving me to distraction.

After what seems like long tortured hours you whisper my ear.

"You can cum now slave".......

I wait..........and I wait......and I wait. Finally.....

Swish.........Crack! I stroke but the moment has gone and I don't climax.

"What's the matter Slave.....don't you want to cum?" you whisper I can hear the mirth in your voice.

Swish......Crack! I stroke.

Swish......Crack! I stroke.

Swish......Crack. The tempo increases and my climax builds. Finally I howl my release and spray my cum onto the floor and my hand.

The blindfold is removed and I see your beaming face in the mirror, I smile back.

"Clean that up" Sissy commands...and Mistress laughs.

Mistress states that our time is up, she leaves the room and the maid enters. She helps us get dressed and sees us to the door.

"Goodnight Sir.......Sissy". She smiles.

Back in the taxi we sit in content silence.

At your hotel door I bid you goodnight.

"I hope we can do this again".............are my last words.