Money Well Spent Ch. 01

"So wha'? You're like, like a dude or something?"

This was shouted. It was also slurred, and, just for good measure, a droplet of spit lasered past my face. My facial expression, one of suitable disgust, fell on a blank audience. He was in that state that a certain type of man gets to when in his cups, one that relies less and less on an opposing party to maintain a conversation. He was managing to blink with one eyelid at a time, and was focused on a point either just above my head or somewhere past my shoulder, it was difficult to tell.

It had been a fulfilling, three-day conference. Two days had been crammed with back-to-back presentations, keynotes and launches followed by cocktails and dinners designed to be more extravagant than any attendee had experienced before.

It was exhausting but so incredibly engaging. Most of the final day had been allocated to time in small breakout groups, drawing connections between amazing ideas that had been shared and presented over the first two days. Inspiration and experience married perfectly to provide a container load of new ideas to take back with me.

One of my companions through this final day was a ruddy complexioned, amiable moron of middling years. At the pleasant-seeming professional end of his spectrum, he'd appeared worthy enough to acquiesce to an offer of a drink in the hotel bar. He had managed to morph from pleasant-seeming professional with the occasional quarter-decent idea, to shirt out, gently swaying buffoon in four quick drinks.

To a backdrop of softly tickled piano, we'd chatted in a pleasant-seeming, professional way until towards the end of his second neat Scotch. At which point the inevitable question arrived.

"So, what does the second half of this evening look like?" he crooned. To add some gravity to his seduction, he attempted what I believe he thought was a suggestive eyebrow cock. In truth the look suggested less about seduction and more a man of middling years embarking on a stroke.

Viewed from without, I hoped that my facial expression conveyed the acute disappointment in my judgement that was felt within. Again, my displeasure went entirely unnoticed. I decided to discard pretense, and knowing this would be the last time we would cross paths, I told him truthfully.

"Oh for me, it will involve meeting the young man and woman I've paid for and taking them back to my room for sex."

As tonight was the last night of the conference, and as I am entirely without shame where my proclivities are concerned, I had no hesitation in boggling his quickly shrinking mind.

Part of me enjoyed the next part. His disbelief. The flabbergaster. The elbow that had been supporting him while he was waggling his eyebrows at me slipped off the edge of the table, narrowly avoiding a slapstick chin-to-table collision. I watched the cogs crunch together awkwardly while his brain tried to find the gear that would allow him to comprehend the reality I'd presented. I could see his mind's eye forming images of fantasy, referencing his sweaty late-night one-handed scrolling before his laptop screen. I watched with amusement as those thoughts then attempted to join enough dots to create a picture where he might insinuate himself, however long the shot might seem, into the evening's revels.

He dealt with it all quite stoically until half way through his third drink. He asked the sort of fascinated, chummy questions that one of the gals might ask. There were even a few nudges and one wink thrown in for good measure. My straight-bat, no-nonsense answers continued to fuel the fantasy section of his brain as the logical, reasonable part that was trying to keep up came to the realisation that in fact, no, the evening wouldn't be involving him.

As he drained the last drops of his Glenwhatever, he'd reverted completely to type; a drunken buffoon.

"Like a dude?" I replied.

"Yeah, you know, a duuuuude. Just in it for the fuckin!" He thrust his hips for me, in case I wasn't able to join the dots.

I glanced at my watch. My guests were due in a couple of hours, and I wanted time to prepare fully. It was time to wind this up. While entirely unnecessary, I felt the need to clarify my position for Gary. Or Geoff, or Warren, or whatever his name was.

"I travel a goodly part of the year, I'm often away from home. I enjoy sex in all its forms, and I won't be denied my desires purely because I'm on the road. So rather than reducing myself to hooking up with conference-goers on the final night, I pay handsomely to have my every sexual whim sated. So have a lovely evening, and do get home safe."

I said the last as I walked away, leaving him slack-jawed and swaying gently.

I had spent considerable time and energy researching my purchases for the evening. Scrolling through potentials, matching and cross-references likes, dislikes, preferences, hard boundaries, experience, as well as simpler things, like the sensations and feelings I got when I looked at each candidate. A good sign, I always felt, was if I needed to close the screen of my laptop and indulge myself.

The young man I arrived at was simply gorgeous. The smile that beamed out from his head-shot would stop traffic, and his bio and description had me quite giddy with potentiality. I imagined all things I could do to and with him as I lay in bed, and came much more quickly than I had anticipated.

The other half of this evening's revels was somewhat an exception to a personally held, if somewhat rubbery rule; a second interaction, a return experience. It's not that I avoided revisiting the same purchase out of any particular rationale, other than the fact that I had never had a bad experience so far. Why stay in one room, I figured, when there is an endless hallway of doors that hide new encounters. But I made an exception for Sabine. She would be, despite the plethora of possibilities, the perfect foil for Alexander.

As I closed the door to my penthouse and slipped out of my shoes, I recalled the long, hot evening with the enchanting and delightful Sabine. She could do such wonderful things with her tongue and fingers, and she had raised begging and whimpering to a beautiful art form. I drifted into the reverie of our previous tryst, my body remembering the string of orgasms she extracted from me as I held her beautiful hair tightly in my fist. She was the perfect combination of supreme ability in her chosen field and insatiable nymph.

I raised a good sweat as soaked in my extravagantly large tub, weaving the two of them together in my mind's eye, and delighted as my pulse quickened. Beneath the water I could feel slickness between my engorged outer lips. After a soak, I let some of the water out and grabbed the handheld water wand. Setting it to prickle, I fired needles of cold water across my nipples, moaning aloud. I swung my feet out of the bath, changing the shower head to a slow pulse. I used one hand to part my cunt lips, exposing my already throbbing clit. The pulse was slow and deliberate enough to make me swear and groan without any danger of pushing things too far.

To ensure a proper level of preparation, I allowed a single finger to slip into my wet folds and my pinky to penetrate my asshole, just for a moment. The touch activated all the correct nerve endings, and for a second I came far too close to climaxing. I turned off the tap, my cheeks flushed both from the water and from my arousal. I had to jump into the shower and run the water cold for a moment to gain ascendancy over my desires. To equalise my mind with the cooling of my blood, I reflected on the interaction in the hotel bar.

I hadn't lied to Terry. Travel was a major component of my professional life, and there had been plenty of years where there had been more months abroad that months at home. My role is such that there are always fires that need extinguishing, palms that need greasing and egos in need of cuddles and soothing words.

I am ever the early arriver to meetings, the most bright-eyed to breakfast the morning after late dinners, and I always over-deliver on key measurables, create synergy and cross cultivate vertical integration. Whatever crap is the buzz speak of the moment, I make sure I doing it. In short, I am bloody good at what I do. But the suitcase life is boring, lonely and tedious. Early on I learned to bring my vibrator. Then vibrators. Then butt plugs, nipple clamps, suction cup dildos and an ever-expanding comfort with, and exploration of, my own sexuality.

But, like the suitcase life, solo exploration got boring, lonely and tedious. Perhaps that's a little harsh. I love masturbating. I am an avid, enthusiastic and frequent masturbator. But I came to realise that I missed the human element of sex. I craved the warmth and tingle of skin. I longed for the smell, taste, feel of someone's arousal. I wanted the feel of a real cock sliding into my asshole, real fingers in my cunt, a person's hand around my throat.

So I dabbled, briefly, with the Kevin's of the travel circuit. There was a Darren. He was forgettable. One Michael was ok until he called 82 times and left more messages than I could count. Marguerite was by far the best of the bunch, she knew how to laugh and how not to be stalky. As we lay in languid bliss, she told me about adventures she'd had when engaging with what she called 'a purveyor of promiscuous perv.'

"That's not what they're called?!" I asked, smiling.

"No, I just believe that one should always use a literation where possible," she laughed and it sounded like waterfalls. "Forget the Tony's," she told me. "Call, say what you want, indulge, fly on to the next city."

She recounted experiences and escapades.

"What the fuck are you doing here with me then?!" I'd asked her incredulously.

"You smiled, I melted, and suddenly the thrill of the chase trumped convenience."

I smiled myself. Her advice had made the travelling life so much easier and so much more enjoyable. The first time I'd called the number on the card, I was more nervous than when I lost my virginity. Here I was, a strong, confident woman, who was paying for sex. All the stigmas and connotations contained therein provided a mental hurdle before I'd even had the chance to consider the exorbitant cost.

I'd nearly fallen off my chair when I saw the prices next to the young men and women I could choose from. But it had been my birthday, and I'd been stood up by an old friend who'd promised to meet me. So I'd purchased a young man named Seb, who had instantly assuaged every concern I'd had. He was sweet and charming, and by the time his wonderful cock was sliding into me, I wondered why I hadn't tried this before.

That first night was rather vanilla, a string of orgasms courtesy of tongue and fingers and cock while he fucked me with expert control. The second time I logged on, I was still nervous, but in a completely different way. Seb had been amazing, but what if he was a fluke? So I erred and ordered a second helping of Seb.

He was like lasagna, better on the second day. There was less awkwardness from me and more assuredness from him. There was still the flush of the new, combined with excitement of a cherry already popped. I leaned into the pleasure he drew from me the second time, and I remember a sensation of abandon that was unfamiliar. He pounded into me with both ferocity and tenderness, and it was incredible.

We'd taken a break for a glass of wine, then he'd pushed items on the dining table aside, shifted me onto it and begun more energetic fucking. Then, as my stamina was beginning to wane, I had been taken by an impulse. Not knowing entirely where mine, or his boundaries, were meant to sit, I took a punt.

"I want you... I want you to come on my tits," I'd ventured.

"My pleasure," he'd replied.

Then, as he'd pulled out of me and taken his raging erection in his hand, and with the thought of his come splattering on my chest, a second impulse took me. I slid off the table onto the floor in front of him, and opened my mouth. He growled and pumped his cock inches from my face. I couldn't believe how turned on I was, so a final impulse sprung me.

"Call me your whore," I said.

He grunted, and preceded to ask a string of redundant questions about my desire to be his whore, which thrilled me more than I ever could have imagined, before unleashing a torrent of semen all over my face, mouth, chin and breasts.

I farewelled him with come still dripping off my chin and a sense of sexual satisfaction coursing through me that was hitherto unexperienced. It wasn't like the BDSM room of my sexual house hadn't been ventured into; I'd always dabbled in mild kink. It was just that I'd discovered a seedy back room beyond my familiar proclivities, one behind a red curtain.

The hours, days, weeks and months of chairing panels, facilitating groups, managing logistics and leading teams were exhilarating but exhausting. When I retired to my own private world, I came to realise that the last thing I wanted or needed was to lead and control. I found that all I wanted was to cede control to someone else. To be told what to do, to have the burden of making decisions removed so only the bliss of physical sensation remained.

I spent the next 12 months exploring my submissive impulses. I instructed my partners that I wanted to be taken and used and punished, and I loved every minute of it. In a cocktail bar I was finger fucked, trying my best to maintain my composure while ordering more Manhattans. I sucked and stroked two thick cocks at once, replete with mascara staining my cheeks. One night, a particularly enthusiastic young man spanked my buttock extremely hard while ordering me to climax around his cock.

That stinging mark had left an impression long after the heat had gone. I blushed when I reflected on how much I'd enjoyed being spanked. It was strange that in all the scenarios and situations I'd indulged I'd never thought to explore sadism. The next time I was alone, a glass dildo filling my pussy and a vibrator on my clit, I'd given my own bottom a smack. That wonderful scrambling of the pleasure pain receptors in my brain made me shiver with added arousal. I'd found a hairbrush in my toiletries and dived into corporal punishment.

I'd required spanking from then on and started exploring implements at a sex shop in one town I'd visited for only one night. A leather flogger had my mouth watering and breath quickening as I paid for it, and the stunning woman who I'd purchased to wield it left me a drooling and ecstatic mess. I was spanked into another dimension, and I was lucky the second day of the conference had been mostly stand-up presentations because I couldn't sit down.

This was also around the time that I fell in love with my bum. It was the depths of winter, and my fun for the evening had been struck ill. When I was called with the bad news, I was offered a full refund, and a replacement should I still intend to have my appetites sated that eve, compliments of the house. What an offer that was.

A mysterious dark-haired young man arrived, dripping wet and breathtakingly gorgeous. Though there had been little time to arrange the particulars, he had clearly read my brief. He was a gentleman of few words, preferring his actions to do the talking.

He began with a luxurious massage, and I quickly melted in his hands. Once passed the relaxation stage of his ministrations his fingers began to weave magic along the inside of my thighs before gently teasing my cunt. I was in such a state by the time he drizzled oil along my anus and began massaging there, there wasn't a resistant impulse in my body. He had penetrated my anus with his elegant finger after teasing it for an age. He had prepared me so well that I opened and accepted him without a hint of discomfort. When he slid two fingers into my cunt, I had never felt so deliciously full and slutty. I actually reached back to hold myself open for him, begging to be fucked in the asshole. He went right on fingering my needy holes with an easy grace, like he had all the time in the world. He knew just the right moments to reapply copious amounts of lube or oil, so that the experience became a miasma of pleasure.

When he slid his cock into my anus, he stretched me in the most delightful way. I came to love that sensation of a feeling that could be just this side of pain; an acknowledgement of the body of this taboo invasion. I screamed my first anal orgasm into my pillow, while his pace never deviated. As my second climax began to ripple through me, he grunted, and emptied himself up my arse.

It wasn't like I needed another kink to indulge, but there I was. Cum dripped out of me, and I felt so wonderfully dirty. He had done such an incredible job of my first time that I had none of the pain and unpleasantness that seemed to be part and parcel of exploring anal sex. To make the whole thing even more enigmatic, I was never able to secure that young man's services again after that. I tried, several times, but it was like he'd vanished from his employers' books. He still fuels many a sordid fantasy to this day.

So my tastes and proclivities expanded and evolved. Being submissive was truly incredible, and I strongly believe that I became more effective in my many roles. Being able to 'turn off' the alpha part of my mind each time I indulged myself was welcome respite from being the person who was forever looked to for leadership or guidance. Like everything, however, the flavour grew same-same, a little bland and predictable.

Feeling I had risen to every submissive temptation, I began to explore my dominant side. I experimented with it in a way that allowed me to drop out of my daytime attention to the minutia and into an escape. I was nearly late to the official launch function for an event at which I was keynote speaker because I was busy seeing how many times I could bring a gorgeous consort to the edge of orgasm without allowing her to tip over. I pegged a man for the first time, his cock twitching and dribbling while the lube I used ruined the very lovely couch I had bent him over. I directed complex and layered tableaux from my fantasy, with one in particular dissolving three of us into fits of laughter with the absurdity of it.

I had pulled back after that, keeping the scenarios simpler, even as the complexity and layered played out in my mind. I had plans for Alexander and Sabine that had taken shape during the previous day's break out session. All that was needed were a few props and a couple of willing bodies.

I glanced at the clock and realised it was time to get dressed. Dressing was a simple affair as in these circumstances as 'dress' was a relative term. Stockings, garter belt, choker, earrings. I considered lace knickers for a moment, then decided against them. There had been odd occasions where guests had been nervous and tentative when they arrived, perhaps unsure of exactly what their brief was. Inexperience perhaps, but I was always able to put them at ease. I wanted Sabine and Alexander to see what the thoughts of them had done to me already.

With a glass of champagne in my hand I began arraying my implements for the evening. A collar and leash, a cock ring, a crop, a selection of brand new and very lovely lingerie. Other playthings, still in their packages, were arranged neatly and evenly along the glass dining table. I applied scent and lit candles, and as the finishing touches were placed, there was a knock at the door.

"Sabine!" I greeted her with genuine excitement. She greeted me with a warm hug and a kiss, telling me how delighted she'd been to get my invitation again.

"I've been talking with 'Xander on the way over here about what we got up to last time you were in town. I confess that something has come over him!" she giggled, a faux Southern drawl touching her accent.