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Completely fictional* escort stories as told by some of our past and present ladies…


Volume 3: Pollie Wants a _ Clacker (PART ONE)

I’ve worked in lots of places (both nationally and internationally) and in a variety of ways – erotic massage, full service and have done both private and agency work or brothel work. People always ask me which option I prefer and, honestly, it really depends on where I am and what I’m feeling.

In certain places I tend to prefer working privately and others, I prefer agency or brothel work. They generally tend to attract their own different clientele (and their own accompanying positives and negatives) – this also varies on the location.

For this particular story, I was working privately in a luxury suite in a major capital city. The main clientele base I cater towards in capital cities are generally politicians, members of their staff and press. Due to the high-profile nature of these clients, they tend to book with private escorts only and require an NDA (Non-Disclosure Agreement) to be signed prior to service.

Why do they book private escorts almost exclusively? I’m not too sure, however, I would assume that the reasoning is that the less people that know, the less NDAs require to be signed and the less likely they are to be exposed?

One day I receive a call for an overnight booking, to be conducted entirely at my apartment the following night. Name used was clearly an alias, Andrew*, but I took down details, collected the deposit and noted his drink preference, favourite food, etc and took to planning the booking.

Overnight bookings generally go down one of two ways, they’re either very enjoyable and fun or they can be a complete drag and really feel like work for extended hours. The risk is usually mitigated if you have seen the client previously and clicked. For new clients, this can be 50/50, you may get along but not well enough to be able to talk and play for 8-10 hours.

This booking was by no means my first rodeo so I began to put things in place should conversation stagnate or sexual play finish very early or be unmemorable. It was the day of the booking and I had Andrew’s* favourite whisky available and ensured there were food options on the room service menu that were agreeable to his palate.

Arranging my workspace, I placed an assortment of sex toys in the nightstand drawer and selected my most luxurious set of lingerie to wear. I slid into my finest cocktail dress, the satiny material caressing my breasts and hips in all the best ways. I carefully glided my stay-up stockings up my legs and secured them with my sexy garters. Finishing up, I put on my best pair of designer heels and I was dressed to the nines, ready for Andrew*.

As previously arranged, 15 minutes prior to the booking time, I received a knock at the door. It was a member of Andrew’s* staff there to settle the formalities prior to his arrival. Once all papers were signed and payment made, the staffer curtly exited the room for the arrival of Andrew*.

Andrew* arrived punctually at my door for his booking. I glided to the door, looking every bit like the snack, main course and dessert. Walking through the door, his eyes devoured me, undressing me as he looked over my body. To be fair, the satiny material of my dress clung to my body like a second skin and did not leave much to the imagination.

“Like what you see?” I asked, my lips curling in a cheeky smile. “Yes,” he breathed heavily into my ear, “you look even better than your photos”. I laughed as I tugged on his lapels, drawing him closer to plant a soft, sensual kiss on his lips. He smelt absolutely divine, an earthy mix of cologne and a just a faint hint of his last cigar.

I ushered him further into the room, offering him a drink. He liked his whiskey neat, which I appreciated. I had done several tours around the world and had accumulated enough knowledge to at least have some understanding on the matter. I  playfully argued the superiority of Scotch whisky while he commented on his preference of American. We continued our small talk as we slowly became more acquainted with one another.

Suddenly he cleared his throat and moved closer to quietly ask if I was surprised seeing him. I told him that I had arrived on an international flight the previous morning and had no idea about local politics or who he was prior to him telling me. I lied. Even if I hadn’t already been aware of who he was, the bill he was trying to pass was generating massive interest over the news and was virtually inescapable. He seemed to calm at my apparent ignorance at who he was.

Trying to sidestep any follow-up questions, I slowly slid my dress up cheekily and softly grazed my calf between his legs. It seemed to work as all thoughts of work, of who he was, of any further questions seemed to completely escape his mind.

He stood up and with his hand reaching out, he began bringing me closer. Pressing my body into his, he hands began roaming my body, exploring my voluptuous curves and tight waist. I tilted my head up as my lips met his, with more urgency and fervour than before.

Breaking away from his hold but never losing his gaze, I slowly lowered the straps from my shoulders. The dress slid down my body, the material pooling at my feet on the floor.

Standing there, in my lingerie, stay up stockings and pumps, talk was over. In a swift move, the space between us closed as we were drawn to each other. My fingers worked nimbly, unbuttoning his tailored suit and sliding it off him.

I continued undressing him as we made our way over to the bedroom.

We were absolutely ravenous in bed, it was the most passionate service of my career. I came over and over during our heated session together.

Afterwards we made our way to the living room to pour another drink. We chatted away about life, economics and eventually got talking about politics. Already knowing he was prior to meeting him and being ever the social chameleon, I leant the conversation to favour his “conservative religious ideals”. I couldn’t help but laugh at the contrast between his public image and the man that I committed several delicious sins with immediately prior.

After many more drinks, I could see him start to get restless so I steered the conversation towards more naughty things he’s like to try. He asked if I had any toys to use and I seductively guided him back to my “office”.

We probably ended up using every toy in existence, in every way imaginable! A particularly hot session was where he penetrated me and then, holding onto a small toy of mine, double penetrated me.

We collapsed on the bed afterwards, still entwined, our bodies shimmering from the sweat. Andrew* turned to me and whispered in my ear. I could barely make out the words in my post-orgasmic haze but it distinctly sounded something like ‘if we could try fisting next’. At first I was a bit taken aback. Although our play was rapidly escalating, I did not expect this turn of events.

Making sure that I didn’t mishear him I asked him to repeat what he said. “Fisting, can we try it together?” he answered back clearly.

Now, I don’t typically try providing services that I am not experienced in, especially with new clients, but at this stage we were several hours (and drinks) into the booking and had developed quite a rapport and understanding of one another. Against my better judgement, almost as though without permission, the words escaped my lips, “sure.” I cleared my throat as reason flooded back to me and I continued, “BUT, we will need to use gloves, plenty of lube and go slowly as I have not done it before”. My mind was absolutely racing, worried about if he’d injure me but at the same time curious and kind of titillated by the thought.

[You might want to stop here, dear reader, should you not wish to hear the events that resulted in possibly the most traumatic night of my career – you have been warned!]

So, I excused myself and gathered all that I thought we’d need. I made sure to grab my extra lubricant along with larger toys I stow away in my suitcase should a client wish to be extra adventurous. Nerves melted away and I started becoming excited of exploring this untapped activity – something I could possibly add to my repertoire.

Entering the bedroom again, Andrew* started shifting in the bed, settling to position himself on all fours. In that moment, I must’ve gone through a thousand different realisations and emotions. Firstly, the realisation that we weren’t trying fisting on ME but that we were doing it to HIM. Secondly, that it would be anal fisting we were trying. Thirdly, from the enthusiasm and the position he quickly moved himself into, he had definitely done this before. Fourthly, was the fact that I had absolutely no idea what I was doing.

I stood there frozen for a moment, in sheer terror, staring at this man’s asshole wondering how the events of the night descended into this. It wasn’t the fact that he was into ass-play or that he wanted a fist there, it was just that, generally, you’d like a bit of notice before you have to put your fist into someone’s asshole.

I composed myself and gave myself the biggest pep-talk of my life. Imagine Rocky Balboa’s trainer amping him up before a fight – except instead of putting fists to faces, I was putting fists to assholes.

Finally I moved closer, “you got this,” I said to myself, trying to remind myself to breathe. I started gloving up and moved into position behind Andrew*. I’d given the occasional prostate massage before, but only ever a finger or two, so I thought I’d start from there. Coating my index finger in a thick layer of lube, I paused for one last apprehensive look and slowly slid the sheathed digit into the abyss.

A soft, almost inaudible sigh escaped Andrew’s* lips as my finger delved in. Slowly moving, I expertly positioned the pad of my fingertip against his P-spot. A second finger joined it’s mate as I began applying pressure to his prostate in a slow pulsing tempo.

I liberally applied more lubricant as I readied a third finger’s entry. Andrew* became more animated in anticipation of what was coming. Teasingly, the next finger grazed the rim, swirling around but not entering. He squirmed on the bed, fucking himself on the two fingers already buried in is ass, trying the lodge the third with the others.

His enthusiasm was soon rewarded as another finger plunged into him. Groaning in pleasure, I continued the pulsating motion against his prostate.

And so it continued, a drawn out dance of teasing, tempting and rewarding him as I slipped in finger after finger. I was glad that I had brought extra lube as each digit was eagerly accepted into his asshole with almost no difficulty.

Eventually, all five fingers were housed snugly within his ass, his cries of pleasure becoming louder and louder with each addition. I no longer needed to do much within him, the pressure already doing most of the work. Every slight motion appeared to send shockwaves of bliss throughout his body.

Now, the final step, I thought to myself as I began curling my fingers into a fist within him. The added sensation against his prostate seemed to thrill him to no end as he began shouting his moans. I noticed how hard he had gotten in the process, seeing his rock hard member swinging below him, slick with precum.

I reached under him to grab his erection with my available hand as my other one was now entirely engulfed.

I wondered why I was so worried in the first place, everything was running so smoothly and it was going very well (I must admit, I was quite surprised how much I was enjoying things up until this point).

My gloved fist moved in short, jerking motions within his ass as my other hand expertly gripped his member, delivering sensations that had Andrew* almost speaking in tongues.

Suddenly, Andrew* tensed up, signifying his impending orgasm. When he finally came, I was not expecting certain things. The vice-like grip his ass had on my wrist startled me and instinctually, I withdrew my hand from him. He blew what seemed like the biggest load I have ever seen and crumpled to the bed, sweating and panting at the exertion. Meanwhile, I stood behind him, once again frozen and terrified.

I looked down at my hand, aghast, the blood draining from my face. I wasn’t sure if I was going to faint from the shock of what had just happened.

Slowly sitting back up, Andrew* was absolutely beaming, a grin from ear to ear and his eyes sparkled. He stopped short when he saw the look on my face, “Are you okay?” he asked, “you don’t look too well”. I must’ve looked absolutely horrendous, I felt like I was going to be sick, like I wanted to scream and like I wanted to die, all at once. “I, umm.. I maybe, umm..” I stammered.

“You did incredibly for your first time,” Andrew offered in encouragement, I blanched even further.

“I think… I think I lost the glove,” I finally forced out.

Stay tuned for part 2…

The “Escort Diaries” segment is for entertainment purposes only. All characters and events appearing in this segment is entirely fictitious, any resemblance to any persons either living or dead is purely coincidental.

All key identifying aspects have been either removed or changed (character names, professions, specific dates and locations) to protect anonymity of these fictitious characters.

More Escort Diary Entries

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Read our other published entries:

ESCORT DIARIES – Vol 1: The Crossdressing CEO

ESCORT DIARIES – Vol 2: The Rockstar Wizard

ESCORT DIARIES – Vol 3: Polly Wants a ****** Clacker

ESCORT DIARIES – Vol 4: Family Ties

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