Hunky Waiter Works The Ultimate Cup Cake Party and Succumbs to the Pleasure and Pain

I’d never heard of a ‘cup-cake party’ – but assumed it was a gentle girls night in with a few tasty cakes and maybe a glass or two of wine.

So when my friend suggested I might like to earn a few extra dollars acting as – in his words – ‘a kind of waiter’ – I jumped at the chance. As a poor hard working student money was extremely tight and not having rich parents meant I had to earn every single penny.

I can tell you now there’s still a tiny piece of me somewhere (I think) that wishes I’d never agreed to go – let alone let what happened happen! But that leaves a whole lot of me loving every single minute of it!

OK I guess like all things it’s best to start at the beginning of my adventure into the darker side of sexual pleasure.  Until that night I’d been a pretty straightforward kinda guy. The closest I’d come to anything ‘kinky’ was fucking my girlfriend doggie style on a park bench!

I guess I should have known when I was asked to wear black tight fitting boxer shorts to the cup-cake party that something was not as it seemed.

I arrived at a rather grand house to be greeted by a plump and overly made up ‘lady of the house’ who eyed me up and down like she would a piece of meat in the supermarket.

‘You’re late and you’re friend isn’t coming’ she said and quickly turned on her heel waggling her finger to make me follow.

She pointed to a door and said:

‘Your uniform is in there – hurry up the ladies are waiting.’

Inside I saw what looked like a fancy dress costume for the Chippendales – white collar and bow-tie and little white cuffs.

I was wearing black trousers and a white shirt – my idea of a waiter at a so called cup-cake party – and slipped the cuffs and collar over my shirt. Checking myself out in the mirror I chuckled – I looked pretty stupid to say the least.

As I walked into the main room I was greeted by half a dozen over weight and equally overly made up and indeed overly dressed women of ‘a certain age.’ They all eyed me up and down curiously and the hostess sprang to her feet.

‘Are you purposefully being difficult’ she barked and clicked her fingers – ‘just your underwear – with the collar and cuffs..’

I was more than a little alarmed and was about to speak when something about the look in her eye made me blush furiously. Suddenly I was transported back in time to the state of being a naughty little boy who had once more disappointed his parents.

Embarrassed I mumbled something but she shoo’ed me out of the room.

I had no idea what the hell was going on – but two things I was certain of – I needed the money and the thought of parading around in front of a room full of women in just my underwear was making my cock twitch with interest.

‘Your friend isn’t coming’ said the woman through the door as I slowly undressed.

‘So it’s just you – let’s hope you’re worth it.’

Entering the room again and this time just in those ridiculous collar and cuffs and my tight black shorts I was strangely pleased to see the ladies eyeing me up and down with what I assumed was appreciation.

‘When would you like me to serve the cup-cakes’ I asked innocently.

‘On your hands and knees in the middle of the room now’ said the hostess ‘the ladies need a table.

I shrugged to myself – why not I thought.

Kneeling on all fours with my ass pointing away from the gaggle of cackling women I blushed furiously. I felt clammy hands on my shoulders and looked up but all I could see was a heavy pair of thighs as the hostess grabbed my ear painfully and pulled me so my ass was pointing towards them.

‘That’s better’ she breathed into my sore ear ‘we want to see the goods..’

There was a round of applause and more than few filthy compliments and despite blushing even more furiously and feeling like a total fool – my good old cock was by now getting very excited.

‘Now’ said the hostess ‘time to earn your money’

Pulling me by the ear she led to me to the huge sofa and I noticed all of the women had by now removed their stockings and shoes. In front of me was half a dozen bare feet – each one with gaudily painted toe-nails.

‘Lick them – lick them all’ barked my hostess.

My cock was by now doing the happy dance and seeing those naked feet I felt a surge of tingling in my loins – this might not be a bad night after all.

I placed my mouth on the first pair of feet and licked happily in what I hoped was a sexy and suggestive way. Getting right into it I grabbed the ankles to get a better grip and immediately felt a sharp slap on my ass.

I hadn’t been slapped like that since long time and unbelievably loved both he sharp pain and absolutely relished the surge of pins and needles racing from my stinging buttocks to my head. Wow I remember thinking – this is fucking hot.

‘No hands – just mouth ‘she snapped ‘I think he needs taming girls’ there was a murmur of agreement and I heard the unmistakable sound of a chain.

Worried now, I turned my head just in time to see a huge dog leash with large chain collar dropped over my head. Before I could react – my hostess pulled it tight causing me to gasp and scrabble at my neck.

Yanking it hard I stumbled – my face buried into the carpet and her foot in the small of my back pinned me down.

‘Bad boy.’ She said ‘bad boy needs a lesson’

I heard the creak of the sofa as the women slowly stood up and formed a surprisingly orderly queue behind me.

I first heard the swish and then stinging pain as what I now know to be a schoolteachers cane flashed across my buttocks. As intense as the pain was it was also quite beautiful a kind of savage sublime feeling that was like a thousand orgasms hitting my body in a single second.

How long the thrashing last I neither knew nor cared. I just remember aching for it to stop but as each delicious swipe struck my buttocks I never wanted that intense pleasure and pain to end. As if in agreement my already hard cock pulsated with a life of its own and throbbed hard against my underwear. I’d never known an erection like it and never wanted it to end.

After what seemed like an eternity I was dragged back to all fours by the jerk of the chain. I stole a peek at the ladies all of whom were flushed with excitement and all of whom had that wild eyed look in their eyes of total and utter sexual lust.

My eyes dropped to the carpet and body tensed both in hope and expectation of what glorious torture was to come next.

‘Lap – lap pussy like you’ve never lapped before.’ She barked and dragged be back towards the sofa.

Lifting my eyes I watched in total disbelief and amazement as each of the women lifted their skirts and slowly revealed their wet and hairy pussies.

I didn’t need a another invitation and buried my face in one glorious wet and musky pussy after another – each time the woman groaned as the orgasm shuddered through her body – the hostess would snap the chain back forcing me onto my knees my tongue licking the sweetness of pussy juice off my lips.

As the last woman moaned as the multiple orgasm swept over her body my hostess snapped the leash back so hard I feel onto my back.

In a flash she was upon me – the folds of her ample thighs and dripping wet sticky bulbous swollen pussy lips cut off the air to my nose and mouth. Undeterred at imminent suffocation, I plunged my tongue deep into her sex. She screamed as waves of pleasure ripped through her body and she sank deeper and deeper grinding into my face like a woman possessed.

Just as I thought I was going to pass out and the last sensation I would have would eb the taste and smell of succulent cunts – she pulled away and sat astride my chest.

I gazed up at her desperate to plunge my rampant hard on deep inside her molten hot pussy.

Hoping that any second she’d oblige my peeling down my pants and straddling me – milking my cock until I came – I smiled.

She slapped me hard across my face causing my head to spin.

‘Cup cakes don’t get any pleasure here.’ She said licking her lips –  ‘cup cakes only give pleasure.’

I saw the rest of the women standing over me. Each one was holding a dildo – each one smiled and licked their lips.