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Work Hard, Play Hard

Category: Lesbian Sex
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I love banking. I love it. The adrenalin. The buzz. The intellectual demands. And – the money.

Wait a moment – why did I use the present tense?

I should have said, “I loved banking.”

I loved it until the discrimination suit which went in my favour, but which also meant I was out.

The payoff was huge. And, to be fair, my legal team were persuasive. Keep quiet, they said, and I wouldn’t have to work again.

Not strictly true, but my people spoke to their people and then spoke to me again, and we did a deal.

The bank denied any discrimination against gay women – then let me go.

While the Frankfurt banking community quietly closed ranks.


That was two years ago.

I left Europe and moved back to Australia.

Still, my new business is doing well, very well indeed.

I should explain – I’ve become a personal trainer. Very personal. I’ve always enjoyed a high level of fitness: I’m not one of your gym bunnies, and I relish my slim, hard body and the good feeling that goes with a high level of stamina.

So I decided to make the most of my assets, so to speak, and combine business with pleasure.

I took an accelerated Masters in Sports Fitness at the University, and when I graduated I approached my future business plan as I would have done when I was in banking.

I knew I had to find a niche. And, as it turned out, it didn’t take long.

So I now specialise as a fitness trainer for gay women. Professional types – bankers, TV and so on.

They pay well.

And – they pay very, very well for the extras I provide.

Per-lease – I’m not your stereotype prostitute, slagging on the street or in some grimy, cheap, back bedroom.

If clients come to me, they arrive at a smart address with protected parking. The concierge points them to the express elevator and calls ahead to let me know they’re on their way. As they step out, they see the discreet business plaque: WFF Inc. (Women’s Fitness First, by the way. It’s incorporated in Bermuda.)

But I often work in a client’s own premises.

And today my afternoon is cleared for one of my favourite clients: Jackie.


“Fuck me in the ass.”

“I’m going to.”

“Ahh – hhh – ”

“Do you need more lube?”

“No – oo – keep pressing like that…… harder…. no, don’t stop…. ah-hhhhhhhh”

“I’m going to make you so wet.”

“You’re doing pretty well… ah – hhh”

“You OK?”

“As if you care…. keep moving with me…. yeah…. harder….. go on…. go deep…..keep playing with my clit…. really rub it…. go ON!”

“Oh Christ – ”


“The fucking strap….. Wait…. Shit – I’m going to finger you…”

“Quick – I was so near the top…. C’mon…. Finger fuck my ass.”

“Like that?”

“Yeah… ahhh hhhh hhhh – uuhhhhh – Go deep again…. GO ON!”

“I don’t want to hurt – ”

“Fuck off – you know I can take it…. Keep rubbing my clit like that…..”

“You’re so wet – you’re so slippery.”

“That’s because you’re so damn good, you slut…. Uhhhhhhh – ”

“Can you feel that?”

“Ahhhh-hhhhhh – I LOVE IT!”

“Both fingers?”

“Ahhhh – hhhh – Don’t stop…… Don’t stop!…..DON’T FUCKING STOP!!”


Jackie loves ass play. She’s a damn good banker as well. She specialises in obscure derivative trading for a hedge fund (even I don’t understand a quarter of it.) She’s one of the main shareholders, apart from the institutions. It can get very rough. Very demanding. Very stressful.

“So, you were in banking?”

“That’s right. In Europe.”

“I know all about that. Liz told me. She said you were good?”

“Liz is one of my clients, yes.”

“She said that you do more than just fitness training?”


“You mean sex?”

“I mean making my clients feel really good.”

“Do you do anything?”

“Pretty much.”

“Ass play?”


“On what?”

I paused. “On the ass.”

Jackie looked at me, and suddenly relaxed. Turning around, she looked at me over her left shoulder.

“How about my ass?”

I smiled at her. “I think I can tick the box.”


Jackie has a great body actually.

We were warming down after our first session. She took off her top and I could see that she took good care of herself. She’d spent enough on her own gym equipment as well: it would have looked good in any club.

Right now she was still breathing hard after the workout, and there was a sheen on her tanned skin. Even though she was wearing a sports bra her nipples were pressing firmly against the thin white cotton fabric.

If I played it right, Jackie would be a blue chip client.

“Let’s take a sauna,” she said.


Our towels were thrown onto the smooth wooden bench as we started to kiss each other. It wasn’t complete professional detachment on my part either.

I know exactly what my job entails, but it’s less work when you begin to like the client.

Jackie’s body was hard as I held her to me, her chest pressed against mine. I ran my hands down her back slowly, then around her waist, and finally over her firm ass and the top of her thighs.

She began to push her pussy against mine, and forced herself against me, shifting position slightly so that she could slide her thigh between my legs.

I cupped her ass with my hands and then slowly stroked and massaged her cheeks.

“Mmmm – keep doing that,” she said.


That was almost a year ago. Now she’s scheduled in for two workouts a week.

“You know what? You make me so hot!”

“That’s what you pay me for.”

“Not the training, smart ass. The sex.”

“I said, that’s what you pay me for.”

“Yeah – I wonder if it would be the same if we became lovers?”

“I wouldn’t intellectualise about it. You’re a banker. You earn too much and play too hard to have to think.”

We were lying in the sauna.

“Really? And how about you, then?”

“The difference,” I said, “is that I really work for it.”

I got up and knelt beside her. “Would you like me to remind you just how hard I work for you?”

Jackie turned her head towards me and smiled into my eyes. “I think I would.”

“Then pile up those towels.”


I’ve learned to give Jackie exactly what she likes.

And, best of all, she likes finishing off a thorough workout with ass love in the sauna.

She grinned and pulled a couple of thick towels off the stand and stacked them against the end of the bench before turning over and lying on her stomach.

Her body glistened under the soft lighting and I massaged her neck gently. After a moment she stirred and slowly arched her back until her ass was high in the air, her knees bent, her legs splayed on the wide wooden bench.

I could see that she was wet – and it wasn’t just the fast four miles we had run, or the weights afterwards, or the sultry warmth of the sauna. Her purple labia were gorged and swollen with anticipation, the coral wet pinkness of her pussy open. And inviting.

I knelt behind her and kissed her left cheek, licking it slowly, tasting her salty perspiration. I lingered for a second, knowing that I was teasing her to a new contour of expectation.

Then I trailed my tongue across her behind. Jackie’s dark, puckered ring had a delicate sheen and I blew gently on to it, watching the muscle flinch and contract instinctively as my warm breath caressed her intimate sensitivity.

I decided to tease her a little, and lowered by mouth to kiss her pussy, first one side, then the other, before suddenly thrusting my tongue deep into her wetness, my face pressed between her cheeks, my nose buried against her anus, drowned in the intoxicating muskiness of her scent.

“Ahhh – hhhhh.”

I heightened the tension by fluttering my tongue up and down, up and down her pussy and ass, never pausing, just lightly licking and flicking each lip, then diving into her pussy, then quickly over her perineum again, then around her ass, lingering teasingly over the mallow centre of her ring, before surfing away again down her cleft towards her pussy lips again.

“Uhh – hhhh – go onnnnn,” Jackie groaned.

I heard Jackie whimpering softly as she pushed back against me, the better to force my tongue even further into her. As she did so, of course, her ass widened, which gave me perfect access.

Drawing back, I trailed my tongue along the smoothness of her perineum, pressing flat against the taut skin, following a slight skein that led inwards to the rougher, darker edges of her sphincter.

I took my time to circle the dark aureole of her ring, tonguing her wetly, before I began pointing inwards, softly at first, and then more insistently, battling with her to let me in, knowing that she was besieged by a multitude of exquisite sensations that were massing to assault her.

She was rocking backwards and forwards now. Grasping her slippery ass I pulled her cheeks wide apart and thrust deeply and suddenly, my tongue hard and forward, as far inward as I could go, her sphincter squeezing it tightly.

Then I pulled away.

“Don’t stop now, you bitch,” she panted, “Go on…”

I didn’t answer, because I knew what she wanted.

Lifting my arm, I reached up into the cool box and took down the small round tin of lube. Because the cupboard was insulated, the lube was still hard and waxy, although it was already beginning to gel in the heat. The point was, however, that it would still feel exquisitely cold on a hot ass when I applied it.

“Ahhh – ye-ssss – go on…..”

I had scooped some more lube and was smearing it around Jackie’s splayed anus, around and around, circling inwards towards the centre, and then around again, pressing generous amounts into her ass until it was wantonly slippery and I could slide my fingers in and out with sluttish impunity.

Her hand had reached back to her pussy as she started to stroke herself.

I didn’t think she could take any more arousing, so I took down Jackie’s anal necklace that she told me she had made especially for her in Singapore.

The strong silk cord was intricately woven, and the heavy, lustrous, lacquered beads were all of a slightly different size, the better to enhance the exquisite release when they were slowly withdrawn.

“Take you time with these,” she had told me soon after we started working together. “It really turns me on.”

I took the first bead between my fingers and pressed it against her anus, lightly pushing it inwards just a little to test her resistance.

I could feel the muscle relaxing – but not enough – so I kept pressing…. and pressing… and then – it was in.

I am always entranced by the way that an ass seems to swallows beads – one moment there is a taut resistance; the next, all has returned to normal, and only the limp string emerging from the pink centre betrays the pleasurable entrance.

Jackie’s fingers were moving faster now; I bent forward and kissed her ass, tasting the sweet neutrality of the lube, probing with my tongue where the cord emerged, and pulled away so as to insert the next, slightly larger, bead.

Again, the ritual of yielding resistance.

Jackie’s breathing was becoming more ragged, and I could tell she was nearing her climax.

“Don’t stop,” she panted. “Fill me up with them,” as she reached and pulled her cheek wider again.

I took the other beads and pushed them one by one into her slippery ass. I could imagine the exquisite sensation of fullness she was experiencing as she approached her orgasm.

Pulling on the white cord, I watched her anus swell outwards. I released the tension slightly before I slowly pulled the first glistening bead out, and then another, as Jackie groaned in pleasure.

“Keep doing it,” she panted, “I’m nearly coming…Ahhhh – faster…”

Her fingers were dancing hard over her swollen, soaking pussy.

I pulled the cord taut and tugged rhythmically so that she would feel each release to maximum effect.

One by one the lubed, shiny beads seemed to explode from her ass.

At the same moment Jackie arched and bucked as she reached her climax, sweat dripping from her legs and back.

“Ahhh – hhhh – hhhhhhhhh” she yelled, before slumping onto the bench, her dark hair wet against face, her chest heaving.

I trailed the sticky, heavy beads between her cleft for a moment, and then gently massaged her legs, running my palms up her thighs, my fingertips becoming wet with her cum.

She turned round and leaned on her elbow.

“Wow,” she smiled. “That was a hard workout!”

“I knew you were up for it,” I said. I loved back to the other bench and we lay still for a few minutes, basking in the afterglow of sexual release. Then, “How about a shower?” I said. “We’ll cook if we stay in here much longer.”

“Yeah – but don’t think you’re finished. I’ve got a tough sales call tonight and I need to be really relaxed. It’s a key deal for the fund. I’ll pay you for another hour?”

“The customer is always right,” I replied. “But you’ll get my invoice later.”

That’s the deal, you see. If you’re in this business, never forget that it’s a business. OK, a service business, so make sure you provide great service.

I think I knew what Jackie would want to do after we’d cleaned up and, frankly, it would be more about her, than me.

I watched her get up slowly and stroll out, admiring her long legs and firm body, making a mental note to maybe work on her arms a bit next time we exercised together.

The thing is, with the work Jackie does, she needs to be wholly focused. Even her body needs to be aligned with her deal making – banking isn’t just an intellectual thing with her. She needs to do her deal making from a place of profound physical calm – all passion spent.


Jackie was already lying on the bed when I came out of the shower, her head propped on the rich Egyptian cotton bolsters, one hand toying lazily with her pussy, the other with one of her nipples, rubbing it into hardness.

The thin wooded Venetian blinds were down, and the slatted sunlight played across her body.

“Get on top,” she said.

I climbed over and leaned down towards her neat dark bush as she pulled my ass back towards her; as my pussy lips brushed against her mouth, I felt her tongue lap hungrily at mine.

For a few moments we just kissed each other’s pussy.

She tasted good, with a hint of expensive lotion before her own juices overpowered the lingering scent of the shower.

I could feel her beginning to writhe underneath me, and I guessed that it would only be a few moments before she wanted me to move.

“Sit on me,” she groaned, pulling me backwards so that I was squatting over her face. “Sit on my face.”

I reached back and squeezed one of her nipples.

“Lick my ass, Jackie,” I said roughly. You know you love it.”

As if on cue, her wet tongue suddenly pressed so hard into me that I was almost pushed off balance, and I pressed down on her, hard, squatting on my haunches.

The sound of her grinding and pushing into my ass was smothered by my weight, and her hand reached down to rub her clit fast.

I was turned on by the sight of her tanned body constrained underneath me, her legs spread wide, her brown nipples erect with excitement, and I started stroking myself at the same time, knowing my wetness would run between my legs onto her face.

Jackie was forcing herself into me now, tonguing my ass so forcefully that it felt she was right inside me and I could actually grip it with my muscle.

I felt shocks of pleasure dancing within me, and I could imagine the darker wonder that she was experiencing as her toned body writhed under mine, squirming one way and then the other, the better to gain a deeper entry.

I was more slippery by the moment, becoming more aroused with every stroke.

After a moment Jackie’s other hand broke free, and she reached down and started fingering her ass, twisting sideways so that she could push two fingers deep within her, wildly stroking herself at the same time, still thrusting upwards into my anus with her flesh-hard tongue.

The eroticism was overpowering. I held her underneath me firmly as she writhed and twisted, the better to push her tongue further up my ring, the deeper to finger her own ass, the harder to rub her clit.

“Uhhhh- hhhhhhh – hhhhhhh.”

Her muffled groans were louder and more insistent, and I knew that I was on the brink of coming.

“Lick my ass, you slut,” I shouted, riding her hard, “Go on, lick me deep!”

I swear that I was almost impaled on her tongue when she came.

With the strength that comes with tumultuous release, Jackie arched her back, fisting her flared, swollen pussy, three fingers thrust deep within her own tight sphincter.

“Ahhhh – hhhhh – hhhhhhhhh!”

We came almost simultaneously, unable not to cry out as our bodies were rocked by seismic waves of orgasm that crashed against our senses.

I slumped down on the bed as Jackie’s body sagged beneath me, our breathing ragged and shallow, our hearts pounding, our minds overwhelmed.


I got up late next morning, and was half watching the business channel. “…Finally, the late breaking news is about a Sydney-based hedge fund that has racked up a billion dollar deal earning its main shareholder……”

I didn’t need to hear the rest – I knew who the story was about.

I smiled to myself.

You see? I still do my bit to help the financial sector.

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