Of Sugar, Pearls and Heels

This is my entry for the 2022 Hallowe'en challenge, an intertwined tale of a growing Then and a glowing Now. With the exceptions of Le Crazy Horse and the Île du Levant, which are both real and indeed truly exceptional, the people and groups in this story are of course fictional and any resemblance to those in the real world is entirely coincidental. No, really!

Please enjoy.

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Overture

"A Hallowe'en party? That sounds like fun! Thank you, Greg. I'd love to go."

I had a thought.

"Is there a theme for the costumes?" It seemed obvious that our costumes should be coordinated.

"I'll be wearing a tux."

"A tuxedo? What sort of costume is that?"

"One which will match your costume perfectly," he grinned.

He rose, went into his study. I could hear him at the wall safe. A minute later, he returned with a shallow box the length of his forearm. He sat down beside me, put it on my lap. It seemed quite old, the red leather covering it a crazed roadmap of fissures and cracks.

I looked at him, at the box, back to him. His hand swept over my hair, closed gently on my shoulder.

"Go ahead," he encouraged.

My hands fiddled with the catches, lifted the lid, then flew to my mouth. My eyes darted to his, down again.

"They were my grandmother's pearls," he said, "I think the Ball might be an appropriate time for them to be worn."

My fingertips slowly traced over hundreds of glistening spheres, trying to touch each one separately. I knew instantly that these were the real thing. Unlike the dull, sterile white beads in the stores I frequented, these almost had a life of their own. They seemed to purr as my fingers ran over them.

.

Sugar

I'd been 'with' Greg for three years now. Yes, ok, it'd started with a website-arranged sugar-baby, sugar-daddy relationship, but it'd grown from there. I thought so, anyway.

It had not been an easy decision for me. My marks had been good, but there'd been too much competition for the few scholarships in my field and it had become bitterly clear that the available McJobs were just not going to get me through to a degree. I wouldn't have starved; there'd been work, but nothing with hours that suited my class schedule and nothing paying enough in any case. And, without a family to help, I'd been on my own.

So, cut to the chase.

Lead-pipe Pragmatism left battered Pride groaning in an alley when I reluctantly opted to capitalize on a girl's last asset. Even after registering online, I still had very mixed feelings about it. For one thing, I knew a number of words for that sort of transaction and shrank from having any of them applied to me. I spent a long time looking at myself in the mirror.

Eventually, after much timid swiping left and right, I settled on one possibility, worked up my courage and thumbed the icon on the screen.

The website set up an initial meeting with him, a public spot, easy to get to and easy to escape from. It was like a blind date arraigned by a maiden aunt.

To my relief, Greg Finn proved polite, gracious and, indeed, charming. He kept his hands to himself and was almost as successful with his eyes.

And he looked even better in person than in his photos. In his 40s and quite tall, he had dark hair with just a bit of grey at his temples. He spoke well, dressed well and was 'in business'. After initial conversation over lunch at an open-air café, we spent an hour walking through the park, talking of this and that, of anything but the elephant in the room. I found his patience with my timidity encouraging; he found it amusing when I stepped off the path to kick my way through piles of fallen leaves.

I became confident enough to find his hand and take it in mine. He looked down at the touch of my hand and squeezed back, very gently. I found it comforting, but was glad he didn't press me for a straight-out answer when our time was up. He kissed my hand, like in a movie, then put me into a cab and handed the cabbie a bill. I could see him watching me as the cab drew away.

What? Well, of course I checked him out when I got home. Wouldn't you?

It turned out that the man even had his own Wikipedia page, not that it said much about him personally. Birthplace, early education, degrees in, worked for, invested in, promoted to, acquired this, merged that, appointed to the Board of, organized charitable, controlling interest in...

Everything I could find on him on the Net related to business; the personal firewall surrounding him lacked only barbed wire, landmines and snarling dogs to make it complete. There was no mention of a criminal record or personal lawsuits and that was comforting. He'd married twelve years before, but I could find no mention of a divorce or, come to think of it, any mention whatever of the woman within the past five years. A tabloid had run a photo of Greg and two supermodels on a yacht in the Adriatic, but that had been four years ago. He'd been seen at some charitable events, had had entered a thoroughbred in some high-stakes races, had been interviewed by a couple of prime-time economic commentators. It all seemed distant, remote and none of it brought me any closer to who Greg Finn really was.

I had to admit that he'd been gracious and personable and he had certainly intrigued me. In any case, my bank balance was never far from my mind; it was evaporating with the same rapidity as my hopes of seeing my commencement ceremony.

We met again a few days later at a small Italian café. The atmosphere was relaxed and so was our conversation. When we went for our walk, I whispered that one word he wanted to hear. He smiled, pulled an envelope out of his jacket and handed it to me. He surprised me by hanging onto it as my hand began to pull it away.

"Think on this, Leah," he said. "Don't rush."

Having said that, his fingers fell away, leaving me staring down at the envelope.

I found his consideration warming, but I wasn't sure what was next (well, next  next, if you know what I mean) and hesitated before looking up. He surprised me again by kissing my forehead lightly, just once, then turning and blending into the fast-moving crowd on the sidewalk.

Inside the envelope was five hundred dollars cash. I stared at it, more money than I'd had in my hands in much too long. Wrapped around it were two sheets of paper with, well, I guess you'd call it a contract. Maybe a list of expectations? I would spend three nights a week with him and three weeks each year traveling with him to his choice of destination at his expense. At least one concert or major social event a month, selected by mutual agreement. An allowance for personal care, clothing and such, specifically including clothing and accessories suitable for formal and semi-formal events. Tuition, books, computer and phone, student fees, etc, etc. Rent and utilities. Spending money.

My jaw dropped a little. I'm not sure what I had expected, but it was hardly this. A week ago, I was wondering how far I could stretch half a dozen oranges and carton of pasta. Now, it was like I'd suddenly emerged from a dark cave into spring sunshine.

Except...

Except...

I was hardly a virgin and certainly wasn't proud of some of my choices in past, but this situation was on an utterly different plane of reality.

I thought about it. A lot. Then some more.

Inevitably, I invited him to my place for dinner. I cleaned the apartment three times, then used his money to buy one good New York strip, organic veggies to roast, a bottle of reputable red wine and some decent coffee beans. The rest of his money I put back into the envelope, licked its flap and sealed it.

+

His eyes examined me over the rim of his coffee cup. I'd avoided discussing the obvious while eating. He'd been too polite to raise it himself, but he was clearly wondering what I had to say.

"This is very good, Leah," he smiled. "Thank you."

I took a deep breath, fumbled for my courage.

"You bought it, Greg," I said. With that, I pushed the envelope across the table. "Here's your change."

"Change?" he said, then realized what change I must be speaking of and what that implied. His face fell somewhat.

"Ah. Well, I'm sorry that that's your decision, Leah." Hands on the edge of my table, he started to rise.

"Wait. I haven't turned you down, Greg, but I haven't said Yes, either. And in the meantime, I don't take money from a man..."

It was my turn to pause. I wasn't entirely sure how to finish that.

He sank back into his chair. His eyebrows rose.

"'Ah' again," he smiled. "I see. Well, I think I see."

His smile turned into a roguish grin. "I suspect this is where she says, 'We need to talk!'."

My lips dry, I tried to chuckle. "I suppose."

So, we did. It was weird in one sense, as unemotional as discussing a wallpapering contract with a painter, yet I was certainly aware how high the stakes were for me.

So, sex. Well, of course sex, but nothing terribly kink - I asked. I would keep my own apartment; he would get a key and I think that worried me more than the thought of actual sex.

We discussed money, snoring, the requirement to maintain my grades at school, faithfulness, dress, visits, medical tests and contraception, hairstyles, grooming, diets, tastes. I found the discussion almost surreal, but stuck with it.

The conversation didn't end; it just gradually wound down, leaving the two of us staring at each other, all talked out.

Sitting there, thinking, I was still not ready to actually commit myself. His eyes lingered on mine. I found him handsome and was pretty sure he was honest and such, would treat me well, but I wasn't even a little bit turned on.

That wasn't really necessary, of course.

I looked out the window, took another deep breath. Moment of truth, Leah. Close the deal or tell him you've changed your mind.

"Um, OK then," I whispered.

I stood, reached for the top button of my blouse, unfastened it. My fingers slid down to the second button, opened it, moved to the third. For some reason, my fingers were shaking a little and I couldn't raise my eyes above his knees.

"Stop." His voice was soft, but it wasn't a request.

'Stop'? Maybe he wants to unwrap his new toy himself?

He stepped towards me. His hand eased mine away from my blouse before gently lifting my chin to make me look at him.

"I want you to think about this, Leah." His voice was as caring, as gentle, as respectful as I could have ever dreamed of. I knew then that he viewed me as a person, not just a convenience for his libido.

"You might eventually come to despise me for this, Leah, and while I suppose I could live with that, I won't risk you despising yourself, too."

That rather left Mama's little girl speechless. Every man I'd known...

"Thank you for a very pleasant evening," he smiled. "It was a good meal, made better by lovely company."

He leaned down, our faces an inch apart. Seeing no reluctance, he lowered his lips onto mine. His kiss — our first kiss — was as gentle as its promise was fierce, soft yet laden with strength and purpose and future vision. I felt my body melt against his, felt an instinctive glow start inside me. I leaned up, tried to meet his kiss properly, but felt him pull away, leaving me almost breathless.

His hand cupped my cheek, his thumb swept over my chin.

"Call me when you're sure," he said and I was left in my apartment, alone with my confusion, my childhood teddy bear and the bottle of wine he'd presented me as a house-gift.

+

An e-transfer came the next day, a surprising amount. I didn't deposit it, for I hadn't accepted, not really.

Two days later, there was a knock on my door. A grey-haired woman in a delivery uniform stood there, a long box in her hands.

"Leah Holmes?"

I nodded.

"This is for you, then."

She handed the box to me, turned and left, her tablet already cuing her next delivery.

The dozen long-stemmed roses were perfect, simply perfect. I looked for a note. Unsigned, all it said was, Thinking of you, thinking of that kiss.

I knew then.

I texted him.

Me too. And my answer is Yes.

+

His apartment was huge, high ceilings, light and airy, flowers and pleasant artwork on the walls.

He took my coat and my small suitcase, placed them in a closet by the door.

"Any problems getting here?"

"Only with the doorman," I smiled. "I think he had his doubts about me."

"Ah. I'm sorry. I'll make sure that doesn't happen again, Leah."

"It's OK, I guess." In truth, it wasn't, not really. The dismissive scorn in the doorman's eyes had been clear enough when he'd seen my suitcase.

"Well, you're here now. I hope you're hungry."

I wasn't that either, but I smiled and nodded. Get your game on, girl.

"May I help?"

"No. I'm done, just now." Only then did I realize he actually was wearing an apron. I giggled, which made him look down at himself and, a moment later, join me.

The dinner was superb -- salmon, grilled asparagus and a tiramisu so light it almost floated off the table. Despite that, despite his charm, I was still uneasy. I declined seconds, passed on his offer of coffee and sat quietly, looking at my hands in my lap as he cleared the table.

He waited a minute, a long minute, then spoke very softly.

"Am I that frightening, Leah?"

I realized how I must have looked. I put on my Happy Face and looked up at him.

"No. I'm sorry, Greg. I was just thinking."

The ball was in my court now. I knew that. There could be no pretence of courtship or seduction; both of us knew how the night would end. I put on a good smile, rose to step around the table and took his hand, pulling him to his feet.

"It's time, I think."

He looked outside; the sun was barely down.

Had he planned on our playing backgammon first?

"All right, then."

My hand rested lightly in his as he led me down a hall, into a bedroom, masculine in décor and very clean. A king-size bed with a rich duvet dominated the room; I found it hard to look away from it. He released my hand and pointed to a door.

"There's a bathroom you can use, Leah. Take your time."

Fifteen minutes later, I emerged timidly, having left my clothing on a hook. The sun had set, but he'd lit dozens of candles - big ones, little ones, tall ones, stubby ones, in every possible style of holder. Their flames danced on mirrors and glass and windows.

The duvet had been pulled down and Greg was sitting on a low chair on the far side of the bed, wearing a short gown of some sort, blue with ornate dragons embroidered in gold thread. His eyes ran up and down my body as I stepped out of the bathroom and into the flickering light. I shivered slightly, managed to avoid that pointless gesture of trying to hide breasts and sex with my hands. Instead, I stepped to the bed, climbed onto it and slipped between the sheets, watching his eyes running over my form again. The silk sheets offered little more concealment than a coat of paint; I looked down to see my nipples clearly evident under them. Embarrassed in spite of myself, I rolled, lay on my side facing him. Candlelight flickered in his eyes now.

He rose, stepped on cat-silent feet around to my side of the bed. I waited, unsure, then heard his robe fall away. The mattress shifted slightly as he sat down behind me and I could feel his firm hip against my bum.

I started when his hand touched my head, tried to relax, let him drive. The hand continued moving down my body, slowly, very softly. It lingered on my hip, squeezed softly, then moved to stroke along my thigh, returning to my head and beginning all over again.

"Leah..."

His voice was soft.

I rolled back towards him.

"I'm sorry, Greg. I'm..."

No more excuses, girl. You made a deal.

I found a bright smile somewhere and held my arms out to him as I shifted over to give him room. The movement pulled the sheet down off my shoulders and chest. His eyes dropped, examined me for a moment, then, clearly pleased, rose back to mine.

"They're beautiful," he whispered and my spirits rose a little at that.

"I was being silly," I replied. I made a come here  motion with my hands. "Please."

He swung his legs up onto the bed, lay down beside me. This kiss was even better than the last one; I found myself wishing I could say thank you to whatever women had taught him, for I was in their debt. I totally hadn't anticipated actually enjoying this, but now, his lips on mine, his tongue slowly finding its way between my lips, I realized that I wasn't chained to that expectation.

His hand touched my hip again, under the sheet now, palm flat on my tummy. I felt goosebumps as his fingers swept over my navel, found my rib-cage, lingered there for a second, then gently enfolded a breast.

He didn't squeeze, just cupped it in his palm. The weight of his large hand was calming, almost comforting. His head pulled away and, silent, he looked down at me with a soft smile before lowering his lips to mine again.

His hand shifted from one boob to the other, exploring now, sweeping soft flesh under it, caressing and squeezing with tender fingers; I felt my body respond, nipples warily hardening, belly tightening, a small swelling in my sex. His lips shifted on mine, his tongue working deeper into my mouth, his kisses full of promise, full of need.

I'd had girlfriends say they wished their boyfriends would spend more time on their breasts, that boob-play is the absolute best. I won't say that it was the best  thing that night, but it was pretty amazing. Knowing, caring, endlessly patient, Greg cast a spell on the Girls, hands fondling and kneading them as his tongue spiraled in towards my now-taut nipples, barely touching them before circling out again, then back in before leaving with a gentle tongue flick, a teasing nip of his lips.

There was no question of not being aroused now. I'd tried to touch him, please him back, but the man had rolled onto his stomach, his manhood underneath him and all I could do was to stroke his head and back with my hands as he gently, slowly, expertly pulled me higher and higher up that erotic slope, heart pounding, breath catching, thighs quivering, labia slick now with happy moisture.

The candles were shorter when his teeth caught a nipple, pulled away gently, stretching my bud before releasing it, instantly dropping down again it to tease with tongue and lips. Again.

And again.

I'd read of breast orgasms, had discounted them as fanciful.

Don't.

They're real.

He'd touched nothing below my waist and my shout was one of surprise as a rolling joy burst forth in nipples and pussy both, drawing from me a low, ragged cry and leaving me shuddering and breathless under his still-fondling hands, the pleasure growing more and more, filling my world with honeyed bliss. I've had stronger orgasms, but I can't remember a sweeter one, one given with such devoted, extended gentleness.

His hand stopped moving and he lay beside me, his hand on my chest rising and falling as I panted in the night.

He lifted his head, looked at me, smiling.

"How's Leah?"

I hadn't the breath to answer and my smile was weak, but it brought a knowing, happy sparkle to his eyes. His hand caressed the side of my face; I leaned into it, kissed his palm.

He slipped out of bed, returned with a tall, heavy glass of some unfamiliar juice over ice cubes and it was the most delicious thing I had ever tasted. I gulped, spilled some on my chin and throat and learned that his laughter had its own magic.

He reached out for the glass and took a deep drink himself before setting it on a side table. I smiled at him, but he was gone and I shrieked happily at the feeling of cold lips on my inner thighs, moving up to still-swollen, still-slippery labia, tongue probing, circling, licking, lips kissing and I was off again, my cries louder this time, deeper, more primitive and joyous joyous exultant as he lifted and moved, his full weight pressing me down onto the bed, a soft probing at my sex and in, entering, stretching me as a woman is meant to be, filling me to my depths with his meat and joy and I bucked up against him each time as he fell, a chorus of wordless cries filling the candlelight.