How Can I Persuade You?

She walked into my office early one spring morning and within a week, her signature was on the deeds for a smart little apartment a mile or so out of town. There is this thing I do where I like to take my successful clients out to dinner. They don't always accept, but it is nice when they do as the restaurants I choose in the town square mean that the likes of Brett and Henrietta are likely as not to see me celebrating my success.

Luckily for me, Mallory Felder accepted my invitation. Even more fortuitously, I accepted her invitation back to her new pad. She had a lot more experience than me with women, but I was a willing and eager pupil and soon we were off all over the East Coast in search of conquests together. She still had lots of contacts in Boston and Portland - some of her old stamping grounds - and let's just say we did a lot of stamping together.

It was about a year into our friendship that she made a life-changing decision. We were in Vegas to let our hair down and go wild. As ever, Mallory was a little wilder than me. I took a very nice Canadian gentleman back to my room and we had a rare old time. The next morning I went down to breakfast feeling very relaxed to find my friend positively glowing.

"Nice evening, Miss Felder?"

She spooned maple syrup onto her pancakes with an impassive look on her face. "Maybe. It was either the most embarrassing, shameful night of my life or something that will change me forever."

I was intrigued. "Why so?"

In answer, she picked up her shoulder bag and opened the top a fraction. I did a double take when I saw it was full of casino chips. "What the fuck? Did you sneak back down and get lucky on the tables, lady?"

She snapped the bag back shut. "Uh-uh. Far too busy getting lucky upstairs. Jeez, the guy was worse than me and I'm a fucking nymphomaniac. I've been fucked a lot recently, but I've not been fucked like that for way too long." She looked at me over a forkful of food. "Taylor, babes - should I feel offended that he thought I was so good I must be a hooker? Do I really look like a Vegas whore?"

I spluttered into my coffee and almost choked. When I put my hand over my mouth to suppress a laugh, she scowled at me.

"Thanks girlfriend. The words left unsaid say it all. Mallory Felder, aged thirty-six, recently divorced and slightly desperate could easily pass for a Las Vegas call-girl."

We stared at each other for a long moment before she dissolved into laughter. "Oh fuck, Taylor - we were at it like animals and suddenly he checked his watch and I realised we had been going for exactly an hour."

I had to bite my lip the situation was so funny. I could barely speak for laughing. "And?"

She drained her coffee cup and poured another, her face once more impassive. "He calmly asked me how much for a second hour and how much to come in my mouth."

Suddenly, laughter seemed the last thing on my mind. "And?"

She gave a little shrug. "I said I was feeling generous and he was a nice guy. I was new in town. Just told him to pay me what he paid his regular girls."

I felt as if my eyes were out on stalks. I repeated my erudite response from her last two bombshells. "And?"

She picked up her bag and rattled it. "Said he'd had a great evening on the tables and a better one in bed."

I finally found my voice after another long slug of strong coffee. "Mallory - how much?"

She held her arms out. "No fucking idea. Taylor, do you know if Smuggler's Cove has any call-girls or escorts?"

I shook my head again. "Not that I know of. Hardly going to be in the common domain, is it? Why?"

"Because if this is only half as much as I think it is, I may need you to convince me that a career change would be a wise course of action."

I looked at her in amazement. "Tell me you're joking!"

She patted her bag. "Taylor - that amount of filthy cash for doing something I love? This is no joke, hon. I think I may have found my true vocation in life!"

When she later cashed in sixty-percent of her chips, she needed no convincing from me. The amount made my eyes water. We played the tables for the next two nights on the remainder and balled our brains out each evening with unbridled abandon. At the end of the second night, as we lay in a rumpled bed licking each other clean, I had no doubts that she would succeed. Hell, I was almost tempted myself.

That's when my nickname for her took life. 'VW.' My best friend Mallory, the 'Vegas Whore.'

Six weeks later, Mallory Felder became - as far as we were aware - the first call-girl and escort in Smuggler's Cove. Well at least she was probably the first since the days of the original smugglers that gave the Cove its name and if she wasn't the first, she surely had to be the best. Before long, she had a dedicated roster of committed devotees and given some of the A-listers on her books, discretion was paramount.

My best friend left her day job and never looked back.

At least she didn't until she decided to marry again a few years later. What possessed her was utterly beyond me, and mercifully soon beyond her. I told her it was a mistake to fall for a client, but she wouldn't have it. To me, he was a bit of a dickhead but utterly besotted by her. For a while, she was besotted too, but like every man in Mallory's orbit, she wore him out and he realised too late he was never going to tame her. However adventurous he was, Mallory was miles ahead and he just couldn't keep up. Unsurprisingly, her chosen career was not conducive to an idyllic home life and it inevitably came to an abrupt end when Leon Ventura decided enough was enough and retreated back to Boston to seek someone a little less 'out there.'

I welcomed my friend back into the fold and we resumed our previous activities as if there had been no hiatus - brief as it was.

Now, two years on from her brief second marriage, Mallory was a little older if none the wiser, and had her sights set on Scott Brooks. I couldn't wait to see his reaction when I presented her for her viewing. As she rightly said, if I were a shoo-in for Scott, he would be a puddle on the floor when he saw her. I loved her deeply and she was my best friend in all the world, but occasionally I envied her hold over men and women, despite my own not inconsiderable conquests.

Jealousy can be such an insidious thing.

I resolved not to give Scott any indication as to how this would all pan out. He would find out soon enough, and it would be all the more fun for us all.

We pitched up at his door a half-hour late. It was only right to keep him waiting, given what we had planned. Mallory had decided on a silent and enigmatic look and I could have wrestled her to the floor on his porch as she stood, dressed mainly in black, smoking one of her trademark dark brown cigarettes. I hadn't smoked in years, but the long, dark cylinder clasped between her fingers looked so sexy and elegant, it almost made me want to take up the habit once more.

When Scott opened his door to us, it was obvious he felt exactly the same about Mallory as I did. His eyes didn't know which way to turn as I smiled at him and Mallory ground out her butt under her booted foot, completely ignoring him, her eyes cast down onto the ground.

I deadpanned at him. "Good evening, Mr. Brooks. Apologies for our lateness. This is Ms. Felder who will be viewing the property this evening."

When I saw his slack-jawed reaction, I felt like I did back in Vegas as Mallory told me her tale. I had to bite my lip as I watched the guy that had ravished me so utterly and completely for the past two nights stare at my best friend like a goldfish that had just been scooped from its bowl by a cat's paw.

And that cat's paw belonged to the nubile, pneumatic and indefatigable Miss Mallory Felder. Once she had her prey in those dainty little paws of hers, there was no escape.

Oh yes, this was going to be a very special night indeed for twenty-two year old Scott Brooks.

And of course it would be pretty special for forty-somethings Mallory Felder and Taylor Whiteley.

Four - Scott

The way things panned out with Taylor were beyond my wildest dreams. I had a thing for older women that began when I did some volunteer work shortly after my eighteenth birthday. One of the organisers was in her mid-thirties, a large strident lady called Maxie that most of us had down as a bit of a bull dyke. On the third night after lights out, I was woken by the sound of someone crawling into my tent. I held my breath for a moment as soft fingers closed around my most intimate part. I almost cried out, praying it wasn't one of the guys coming on to me, when I heard a whisper in my ear.

"Hey it's me, Maxie. Sorry, very naughty of me, but I caught a fleeting glimpse of you in the showers earlier. Just a thing I do - a perk of the job, huh? Never seen one that big - no way I can pass up this opportunity."

For the rest of the fortnight, it was me sneaking into her room each night. Coming up between those massive tits of hers was a pleasure I would never forget and she did things with her mouth no girl had ever done to me. She was no looker, but she knew what to do and I learned a lot from her.

Since then it had been girls my own age and while some of them relished my size, others were less than enamoured. A few started out with enthusiasm, which quickly waned when my initially clumsy thrusting became painful for them and I soon learned that to be well-endowed was, to pardon a crude joke, a bit of a double-edged sword.

But there had been no problems with Taylor. When she came back the second night to do her 're-measuring' I had my first real, full-on bout of anal sex and it was utterly glorious, sliding into her well-lubed back passage. There were no moments of having to hold back or wonder if she was in discomfort. Just an endless tirade of pure filth from her cultured mouth as she urged me on and demanded ever-more depraved things from me.

At the beginning she giggled as she produced a tape-measure and began to unfurl it along my erection. "Don't think my electronic one will work."

It had never really been a thing for me to know the size. It was just something that was part of me, like size fourteen feet. Something that seemingly could give pleasure or pain in equal measure. Sometimes I thought it a curse. Maybe it was time to think differently.

When she reached the tip, her face fell a little and she put on a pet-lip. "Aw shoot - Mallory told me the biggest she'd ever had was almost eleven inches." She held the tape up to me. "Fucking lightweight little boy - barely a scratch past nine and a half!"

She spent the next few minutes trying to 'coax it past ten,' as she put it, but it was soon significantly less than that as my cum dripped from her chin onto her breasts and I looked on in awe as she toyed with it.

When she told me about the viewing the next evening I was initially disappointed, thinking that maybe we would not be getting together. The sex had been utterly stellar - far and away the best I had ever had, and it occurred to me that the quicker the sale went through, the quicker I would be back home and a long way from her undoubted charms.

Then for the second time in three nights, I opened the door expecting disappointment and ended the night wondering how things could get any better.

I barely heard Taylor speak as I took in a tall, black-clad woman with jet-black shoulder-length hair. Everything about her was dark other than her pale skin and blood-red lips. Even the cigarette she smoked was dark brown. She stared off into the distance, an arrogant look on her face as if what she was about to do was beneath her. Smoke curled up from her parted lips and I recalled Maxie having her post-coital cigarettes as we lay together in her log cabin. I had never smoked and nor had any of my girlfriends, but something had stirred in me lying there with Maxie. It was a little thing of mine - a guilty pleasure and I often felt pangs of regret that I hadn't the courage to ask her to go down on me while she smoked.

I could barely take my eyes off her as Taylor's words sounded like the buzzing of bees in my ears. Finally, the woman ground out the butt under the heel of a pair of black leather ankle boots and merely stared at the ground, looking bored. She looked like a forty-year old woman impersonating a bratty teenager and I was utterly smitten at first glance.

In a complete daze, I let them in and she brushed past me, gazed around the foyer and once more completely ignored me. I am pretty tall at six-two, but she was only a few inches shorter and had to be at least five-nine or ten. Silver studs on the shoulder of her tight leather jacket caught on my upper arm and sent shockwaves through me. It was obviously a deliberate act and elicited the first word I heard her speak, even though her gaze was anywhere but on me.

"Sorry."

Given her distracted and irritated tone, sorry seemed to be the last thing she was and I was surprised Taylor allowed her to get away with her rudeness and ignorance. Instead, she merely said, "Please go on through to the living room, Ms. Felder. I just need to speak with Mr. Brooks a moment."

The woman continued her distracted gaze as she moved out of the hallway. "Yeah, ok."

I expected a dismissive wave of her hand and a bored, "Whatever." I whispered to Taylor. "Is she for real?"

She gave me a big shrug and kept her own voice low. "Clients, huh? Sorry, we'll be out of your hair before you know it. I'll show her round if that's ok. You did clean up after last night, didn't you?"

I nodded, smiling at the memory of our night together. "Took all morning. That woman is insatiable!"

She grinned like the cat that got the cream. "Well someone got very nicely sated. Right enough of this dirty talk - time to work. Catch you in a few. Hopefully, she'll like it - I'll use my charms."

"Ok. I'll give you room." I handed her a spare key. "I'll head up to the Dockyard. Fancy joining me for one afterwards."

She shook her head. "Nah, been a long week already and I may need to get into discussions with her afterwards. Enjoy your drink - I'll put the key under the doormat. You good for tomorrow night?"

"Betcha!"

"Ok, great." She inclined her head towards the living room. "I'll call if there's any news."

Disappointed that I wouldn't get another glimpse of this enigmatic dark-haired potential buyer, I wandered up to the Dockyard, also a little deflated that there apparently wouldn't be another night of passion with Taylor. I sincerely hoped the woman would not put in an offer. A few days earlier I had been itching to get it all done and be free of Smuggler's Cove. Now I wanted things to drag on so I could stay for as long as possible.

As I walked up the riverside, I realised that Taylor had told me the woman's name when they were at the door, but it never registered with me. Her appearance certainly had - the tight leather jacket, short boots and even shorter leather skirt over deep red tights were etched into my mind. Throw in her mass of naturally curly hair, the dark eye makeup, blood-red lips and that cigarette and it all added up to an incongruous mix. A forty-something Goth wannabee. I couldn't get her out of my mind as I ordered a burger and beer and sat watching the sun go down on the terrace overlooking the harbour.

I was just about to order a second drink when my phone rang. It was Taylor. My heart sank at her first few words, then I began to perk up a little.

"Oh, Mr. Brooks - some good news. Ms. Felder is very keen on the property, but there are one or two things she would like to discuss. I'm back at my place talking to her now. Any chance you could swing by?"

I quickly paid for my meal and drink and set off back to the condos wondering once more what was about to play out. Taylor let me in and I was astonished as to how odd it felt to walk into a mirror-image of our condo with all the different decorations and furniture. It looked familiar but strange at the same time.

Taylor kept her voice low again. "She's keen but wants to discuss the price. You ok talking to her? Maybe get a quicker agreement than with me there."

She led me through the living room and up onto the balcony where the woman leaned against the rail, a cigarette in her left hand as she gazed out over the now rapidly darkening scene.

"Ms. Felder, Mr. Brooks is here. I need to make some calls, so can I leave you to discuss things?"

She turned and stared hard at me, pulling on her cigarette. "Yeah, fine."

She was clearly a woman of few words.

"Ok, I'll leave you to it then."

I found myself alone with this strange woman as she took a final hit on her cigarette and flicked the butt over the edge of the balcony. I thought it was a rather rude and disrespectful gesture in a stranger's home and hoped she hadn't done anything like that next door.

She tucked a stray wisp of hair behind an ear and ran a hand over her face. Her voice was a bored drawl, as though she could barely be bothered to make her point. "Scott, is it? I'm Mallory. I'll make an offer if you drop by twenty-five."

She was certainly to the point. I was utterly bewildered and felt very out of my depth. "What, twenty-five thousand?"

I was greeted with an expulsion of air and a roll of her eyes. "No dumbass, twenty-five fucking million." She shook her head and her curls swirled around her face which was now set in a pained expression. "Of course twenty-five thousand. So - are we good?"

I was speechless. "Erm, I think we have some wriggle-room but I'll need to call my Dad, but it won't be until tomorrow now."

Her exasperated sigh rent the night air. "Oh, fuck that shit. I can't wait until tomorrow. Apparently you've been sent up here to seal the deal, so seal the fucking deal. I'll ask once more and once more only. Can... you... drop... by... twenty-five?" She punctuated each of the last few words with a step towards me and my heart began to race. Now almost in my face, she looked up into my eyes. "Yes or no. It's a deal-breaker or deal-maker for me."

When I stayed silent, still unable to answer her, she gave me a wicked little smile. "Tell you what, you seem like a nice boy. How about I give you a little incentive?"

She sank to her knees and looked up at me, her dark-rimmed brown eyes burning into mine. Her words echoed Taylor's from a mere two nights earlier.

"How can I persuade you?"

When Taylor came back onto the balcony two minutes later, my head was rocked back, my mouth wide open. My erection slid between those blood-red lips and my hands gripped that thick black hair in huge bunches.

Taylor stood with her hands on her hips and surveyed the scene with an amused expression. "Well, I'd say our new neighbour on the left would be getting a fine old show if it wasn't for the fact that he is central to the action!" She pointed at the vision in black on her knees doing incredible things to me. "Scott darling, this lady is my best friend in all the world, Miss Mallory Antonia Felder. She is forty-two years old and as you can see, has amazing talents."

The woman stopped her work for a moment and held up a hand. "Delighted, Scott. Heard all about you from Taylor and decided to have a little fun."

For some reason, given the weird situation I was in, it felt perfectly natural to shake hands with a woman who was in the process of blowing me. "Delighted too, Mallory. You're making a very convincing case."

"Should think so." She looked up at Taylor and waved my erection at her. "Nine and a half is my best guess."

Taylor grinned. "Spot on as usual, give or take a tiny scratch! Now - do you think Mr. Brooks will need additional persuasion or can I leave you to it?"

Mallory rose to her feet and pondered for a moment. Close up, she really was a spectacular sight. She ran a finger along her lips then along mine. "I think in this case, maybe two heads are better than one, Taylor. I'll go and get the handcuffs ready and we shall soon have this young man at our not-so-tender mercy."