A Black Night in New Yorkbymandywilluk2000©
Charlene first featured in the my story, From a Physio to a Gigolo, that has been published here on Literotica.
Sipping at her second glass of white wine in under half an hour and chain smoking her Marlboros, Charlene paced around the living room of her suite in the Plaza Hotel in uptown New York.
It was always like this. Every time she had the same feelings. The worry that the arrangements may have been screwed up, the anticipation of what would happen over the next few hours, the concern as to whether what she'd ordered would be matched by what turned up, the expectancy and the nervousness as to how things would go. Yes every time she used a male hooker she felt the same.
Charley, as most people called her, had a pragmatic view on love and relationships. She didn't believe in the former and hadn't got time for the latter. But she needed sex, plenty of it and often.
So this was her answer. Booking male escorts from high class agencies and spending time with them in her hotels or at her apartment in the Docklands area of London where she lived.
It was the only practical way she could get the sex she needed and maintain her incredibly successful job. There just wasn't the time for relationships and her career. She'd tried. Even to the point in her mid twenties of getting married. It lasted less than a year. Men found it hard to live in her shadow and be second fiddle to her job. As a Senior VP in the Merger and Acquisitions Department of one of the world's leading banks she regularly worked a twelve hour day, usually six and not infrequently seven days a week. She was based in London but traveled frequently in Europe and had to visit New York at least once a month.
So there just wasn't the time for relationships. Sure she had opportunities for casual sex and sure she took some up. But they were usually a dinner in a grand restaurant with a colleague or contact. A dinner or, occasionally, a lunch, followed by sex in a hotel. Rarely, even if they'd wanted was there the chance for a follow up. Both Charley and those types of contacts had such busy work schedules that finding the time to arrange a follow up was as good as impossible even if they tried hard and really they didn't. In the high finance, fast moving business of banking things moved at such a pace that people lived for the present. That suited Charley. She didn't want the encumbrances of having to think of others for that could affect her career and to her that was paramount.
Since joining the bank straight from London University with a 1st Class Honours degree in Economics she'd been on a fast track. She'd moved up the organisation spectacularly rapidly. She was smart, very smart and cunning. She had an analytical mind and a determination to succeed that precluded all other considerations. Her bosses had seen this and had used it to give her more and more responsibility until now she was one of their top M & A specialists. But there was still further for her to go. She had the ambition to become the first female MD in the M & A Division of the bank and was totally determined that nothing was going to get in the way of that.
The rewards, though, were as spectacular as the hours were long and the workload was murderous. Charley earned well in excess of £300,000 a year with that often being topped up by additional commissions and bonuses. The perks were equally outstanding. In addition to all the usual health care, pension and other benefits she had a car at her disposal whenever she wanted it to ferry her to meetings and the airports. She flew everywhere first class and stayed in absolutely the best hotels and ate at only the top restaurants. After all when you're working on a deal that's worth billions and with the fees to the bank running into tens of millions why travel club or stay in Marriotts was the attitude?
It had taken Charley some time to adjust her attitudes towards relationships from what young girls are taught. It had taken even longer for her to come to terms with buying sex. But her pragmatic and analytical mind had enabled her to take on board what one of her female colleagues in New York had told her a couple of years ago.
"Just buy it Charley, what's the fucking difference," she'd said handing her a phone number. "It's the best male escort agency in town, fucking expensive but they have the best stud around. Anything you want, young, old, pretty, aggressive you name it they'll have it I promise."
Feeling a little sorry for herself being alone in New York nearly two years ago on her twenty eight birthday and knowing that her meetings were going to finish early, by her standards that is, around nine, she'd recalled what her friend had told her and had called the agency.
It worked out so well she could hardly believe it.
The girl that took the booking treated her just as well if not better than the receptionists at the top hotels and after discretely asking a few personal details such as age and physical details enquired whether she had any preferences for the type of man.
"Or maybe I could e-mail you our questionnaire we'll then have everything on file for the next time won't we?"
Charley completed the questionnaire. She had to answer a host of questions on herself truthfully inserting her height at 5 feet six inches, her weight at 125 pounds, black hair, short and green eyes. She chose her bodily description as slim and her figure as curvy with small breasts.
She mailed it back and was amazed when within ten minutes or so she had a reply with the details and photos of a dozen or so men that met the criteria she'd made. The mail asked her to nominate her 1, 2 and 3 just in case some were unavailable. After she'd done that she got another mail advising that her first choice wouldn't be available until after midnight but that her second choice was ready right now.
"Hi it's Ken," the voice said on the phone after Charley had conducted the credit card details with the agency.
Charley had been a bag of nerves waiting the hour or so for Ken and had several times thought of canceling. But at last he was downstairs in the lobby of the Pierre hotel. That was before the Trump organisation had retained the bank's services meaning that they transferred their allegiance to the Plaza.
He was as good looking as his photo and right from the moment when she'd opened the door he did everything to relax her and make her feel as if it was a date. There was no rush and with all the financial stuff already taken care of it wasn't long before Charley almost began to believe it was a date.
He didn't make any overt or pushy actions or gestures to her and quite tenderly made it appear as if it was a seduction. And that was how it had felt to Charley as gradually he'd undressed her while kissing her, after enquiring if that was ok? It still felt like a seduction as, when she was down to her bra and pants and he'd removed his shirt and trousers, he'd romantically picked her up and taken her to her bed in the room, (at that time her position in the bank didn't warrant a suite). And it still felt like a seduction when he completed it by fucking her three times over the next few hours.
So that had started her on the use of escorts to satisfy her needs. Clean, quick, no strings and usually bloody good was how she felt about it. No baggage afterwards, just fuck and walk away, perfect for her needs and life-style.
Things were a little different in London where she lived. If anything her hours were even more murderous there for usually she didn't get home until around ten and often, especially when nearing completion on a deal, not until the early hours. So opportunities even with escorts were less easy to arrange.
But her friend Gill had helped her there.
"I've found this amazing physiotherapist," she'd told her.
"Oh yeah, big deal. What do I want a physio for?"
"Actually luv to get your rocks off with in the most incredible way." Gill explained for Charley had told her about her use of male escorts.
Gill had gone on to tell her how when she'd gone to the physio practice not far from where they both lived in Docklands with a pain in her legs she'd had the most incredible experience for he'd made her cum on his massage table.
"What you mean he just did it, cheeky sod," Charley said surprised but interested in what her friend was telling her.
"No it wasn't like that. What happened, or so it seemed to me, was that he hinted that something more was available than just the electronic treatment and the massage. And that by itself was great."
"What's he like?"
"Really hunky, about twenty four or five, well built, good looking and oh he's an Oz."
"Mmmm sounds a good package. What do you mean hinted at?"
"Well as I was lying on my front on the table."
"What did you have on?" Charley interrupted."
"My panties and a towel covering my bum."
"OK, so what happened?"
"Well as he massaged the back of my legs he went nearer and nearer to my panties, often so it seemed, as though he was going to touch me there. It was incredibly arousing."
"So did he?"
"Eventually yes but not until I sort of made it obvious I wanted him to."
"And when you did that, what happened?"
"He made me cum."
"But that's not all."
"No there's more?"
"Yes I wanted him to fuck me but he wouldn't or couldn't there."
"But somewhere else?"
"Yes he came to the house and we had it several times."
"Was he good?" Charley asked her interest now fully perked.
"He was bloody good. He's hung like a fucking donkey and fucks like a rabbit. I haven't had sex like that for years."
"Hmmmm what a catch."
"I think so and I'm seeing him again tomorrow like me to mention you to him?"
Brad had suggested to Gill that her friend make an appointment at the clinic. Charley did, and she'd gone along a few days later. Gill wasn't wrong about him. He was a gorgeous young hunk and everything her friend had described about him and the massage was true.
The massage was superb both from a technical body toning point of view and from arousing her. As Gill had said the ever increasing closeness of his hands to her pussy, which she'd covered in the minutest of thongs, was outstandingly erotic. The orgasm those hands then gave her was strong and satisfying. And, just as Gill had explained, no matter how hard she tried, and she did try very hard he wouldn't fuck her there in his massage room. But no more than two hours later when he came to her flat he did. And that was every bit as good as Gill had said it would be and in Charley's view a snip at the two hundred pounds she'd given him.
That had been the start of a business relationship with Brad that had gone on for over a year now. Not every week and not, sometimes, even every month, but always she came back to him and they'd have great sex. They even continued doing it after Brad stopped being a physio and set himself up as a full time escort. And even now when he was running a very successful escort agency of his own, based on young Aussie masseurs that he trained himself, he still serviced Charlene from time to time for the same two hundred pounds they'd started at.
"Hi it's Carl from the agency," the rich, velvety voice oozed into Charley's ear as she grabbed the phone in her suite. "Is that Charley?"
"Yes, yes it is."
"How are you ma'am?"
"I'm fine thanks. Can you wait a few minutes?"
"Sure of course I can."
"Look stay right where you are and I'll either meet you there, you're by the house phones right? Or if I haven't inside ten minutes call me again. OK?"
"Ok, sure that'll be just fine."
Although the agency that Charley used in New York was ultra dependable she still liked to check out "the goods" before final purchase. So she'd developed this way that in a busy hotel, as the Plaza certainly was, she'd get her escort to wait downstairs while she took a surreptitious peek at him.
She whizzed down the twenty five floors in the newly installed high speed elevators that had been put in for the users of occupiers of suites and wandered past the showcases of Cartier watches and Bulgari jewellery. Closing in on the area behind reception where the house phones were located she saw what she guessed was her man for the night.
He fitted the agencies description and the e-mailed photo perfectly. Tall, around 6 4, muscular but lean and with a taught build, about 190 pounds. Smartly dressed in a black suit and gleaming open necked white shirt he looked to Charley to not only be precisely what she'd ordered, but also to be almost perfect. Ruggedly handsome with sparkling eyes, a square chin and the most lustrous, black skin she'd ever seen on a man.
Charley had never been with a black guy. Not through any prejudice or anything for she'd fucked a couple of Arabs and had been with two Pakistanis. No it was just lack of opportunity. After all in the rarified air of upper organisation banking life not too many blacks are around are they?
It had been her friend in London Amanda Williams who'd said to her about black men being all they're rumoured to be. Amanda had divorced her husband and had become very involved in chat rooms. In them she'd met a number of black guys who'd sent her photos of their gigantic dicks.
"It's hard to believe Charley but there really is something awesome about being stretched to the limit by one of them," Amanda had explained.
"Oh you met someone from on there then I thought you always said you wouldn't?"
"No not from on there, when I was on holiday in LA. But its not just the sheer size, although looking at, say, ten inches of thick, hard, black cock and imagining it up you is an incredible feeling, that's so amazing about sex with black guys. They're also considerate, imaginative, adventurous and by God can they cum and cum and again. But mostly I guess it's also how they make it fun." Amanda had told her just before Charley had left for this trip to New York.
On Concorde on the Sunday that Charley flew over she found her mind frequently slipping away from the briefing documents about the two electronic businesses that were in the middle of a bitterly fought takeover. Instead of reading about their P/E ratios. ROCE, PBTID and all the other financial criteria she found her mind thinking, ten inches long, eight inches girth. So after checking into her suite at The Plaza she'd called the agency she now used.
"Oh hi Charlene, yes this is Marie. How can we help you today?"
"I'd like to schedule a booking for Tuesday evening if I can?" Charlene had learned to plan ahead for the classy guys on this agency's books were in high demand.
"Of course what did you have in mind?"
"Er well do you have any black guys at all?"
"Of course how many would you like?" Marie joked.
"Just the one please," Charley replied a little coldly not taking easily to making the selection of a sexual partner a lighthearted matter.
"I see from the records Charlene that you've never booked a black guy from us before."
"Er no, no I haven't, in fact I've never been with one."
"I see may I ask if there's any special reason you now wish for one and whether you're looking for anything particular from him."
Even Charlene with all her balls and confidence found it difficult to say that she just wanted a great big cock. This wasn't though a new situation for the agency.
"We've just started a new feature Charlene I don't know whether you're aware of it?"
"Oh what's that"?
"We now include the size of their penises both flaccid and erect on their details."
They agreed that Marie would e-mail a few over and even before Charley had unpacked she'd chosen her "date" for Tuesday.
The newly installed high speed elevators "for the exclusive use of the mid level suite occupants" were not all they were supposed to be for it seemed to take Charley an age to get back. She was hardly inside the door when the phone was ringing.
She gave him the suite number and waited nervously for his arrival.
"What can I get you to drink?" she asked after they'd made their introductions.
"May I ask what you're drinking Charley?" Carl asked very politely.
"Probably white wine."
"Then that'll be perfect for me too."
Sitting in the enormous luxury of the suite chatting about a wide range of topics the situation, as it usually did, seemed unreal and so incongruous to Charley. It hardly seemed possible that this was purely a sexual encounter for as always they danced around that subject building the pretence that it was more than that. More than Charley just wanting to get her rocks off. More than Carl being a male hooker. And more than the fact that Charley had ordered a "seven inch soft, eleven inch erect" black man to fuck her tonight.
Sitting in her smart, white trouser suit her long slim legs crossed as they chatted about the relationship between Bush and Blair, Charley's mind kept focusing on what lie between Carl's legs.
"Could it really be almost a foot long? Could she really take the nearly eight inches of its girth? How much of it would actually go up her for her insides surely weren't a foot deep?"
"Would you like another or…………..?" Charley asked letting the sentence hang unfinished.
Carl stood up and walked over to her. He slid his arm around her narrow waist and put his face close to hers as he replied softly with an appealingly mischievous glint in his eyes. "How about another and an or…………..?" as his mouth closed over hers.
Most escorts waited for the client's permission to kiss. It was an odd etiquette and some escorts didn't like to do it at all. As equally, Charley assumed, some clients didn't like the added intimacy and tenderness brought about by kissing preferring merely straightforward sex.
Not Charley though. Although she was a hard nosed businesswoman with a very pragmatic attitude towards relationships she still liked her time with her escorts to be as special as possible. It was as though they became an oasis of loving, erotic tenderness in her arid desert of loveless meanderings through life. During the two or three hours she was with a man he became the most important thing in her life and it was almost as if they were real partners.
As Carl's lips pressed against hers and as his arm slid round her waist so Charley responded. Her mouth opened to his probings, her tongue pushed back against his and her arms went round his neck. They kissed for some time. They weighed each other up, probed and researched each others mouth, tested out each others lips and teeth and gums. He was a great kisser. He knew it and prided himself on it and Charley rapidly learned it. She'd never been kissed like it before. Alternating between almost filling her mouth with his tongue and licking and kissing her lips and cheeks he pulled her body hard against his as he varied the intensity. One moment he was grinding and squirming their lips together the next he was licking along her lower gum so gently and softly. And then he'd start to pump his tongue in and out of her mouth.
He clearly had a long tongue and he bent it so that it was more like a tube. He then used that tube to simulate fucking her mouth. Having a surrogate cock coming from his mouth into hers created an almost surreal experience for Charley, as Carl had known it would from previous experience. She just couldn't understand the effect it had on her. It was as if she was sucking his cock in some ways but in others, as her eyes were closed it, was more as if her mind was imagining that she was really being fucked. He'd slither the tube of his tongue across hers, running it along the roof of her mouth until the tip was right at the back of her mouth. After a brief moment when he just left it there he'd then start thrusting in and out of her opening and closing the tube as he did. Charley found herself responding to this. She found this amazing tonguefest becoming the entire focus of their lovemaking. Nothing else seemed to matter as Carl fucked her mouth so acutely with his tongue. She sucked on it, she held it between her lips and then bit gently on it between her teeth. She pushed the point of her tongue into the orifice created by Carl curling his and then started pushing in and out of that. Her mind was reeling a little from this odd and unique oral sex. She felt as though she was being fucked but at the same time she felt as though she was also fucking him and that she couldn't get her mind round.