For a few days now, my agent Ada has been trying to convince me to accept an assignment with Jane, a forty-nine year old career woman, the high profile CEO of a major business organisation. Most people, both men and women look on her as an incredibly formidable woman, especially people working for her.
I was familiar with her work history, turning a start up into a large, successful business, her divorce, numerous media stories and profiles, some of the stories not at all flattering. The constant rumours and innuendo about her sex life or lack of a sex life were fascinating for me and many others, men and women. Did Jane even have a sex life?
Every time I saw her on TV I wondered about her, fascinated that such an unattractive woman could achieve so much. At first glance she was close to ugly, with her dark hair parted down the middle, though as soon as she spoke, her confidence and charisma shone through. Her wonderful, dulcet voice and hard to place accent always so easy to listen to with her confident smile and persona. She was a little taller than average, slim, skinny almost to look at, always immaculately dressed in expensive designer clothing.
“I think Jane would be dynamite in bed. I don’t think you would be disappointed at all,” Ada told me over the phone while trying to convince me into a highly paid one night stand with her. Over time I had learnt Ada was invariably a good judge of her female clients and their sexual foibles and abilities. Why was Ada was taking far more interest in Jane than she normally does when arranging my assignments, I wondered?
I am Michael, in my late twenties, 72 inches tall, 168 pounds, a toned, fit body and genetically lucky to possess a large, thick cock, ten-inches when erect. I live in Sydney, Australia and used to moonlight as a gigolo or male escort.
That was before Ada asked me to work for her ‘exclusive agency’. “We have a wide ranging client list, males and females, and lots of constant work,” she told me while she auditioned me. “And we provide for some very kinky people, even famous people with lots of sexual fetishes.”
I quickly learnt Ada did have a niche clientele of older women who enjoy a one night stand. watching their toy boy, lover or husband giving a blowjob to a younger well hung gigolo after they have watched her fucking him. It can be incredibly exciting for me if the woman is actively participating, a three-way, even more exciting if the woman has a sexy persona and a good body.
Ada had asked me to meet her in the foyer of one of the major hotels at eight on Saturday night, when she would introduce me to Jane. A far different and unusual arrangement than in the past for my assignments. As always Ada was beautifully dressed and made up, turning heads when she arrived, in heels, and an above the knee, white designer coat, looking very sharp with killer heels and black stockings. “This is very exciting for me,” she smiled without any explanation.
Ada is still a most attractive woman; I can still recall her wonderful naked body from when she first auditioned me. And from the rare assignment we shared with another couple. A brunette size 12-14 voluptuous body,, good skin, wonderful legs, a big firm ass, C-cup tits with big nipples and closely shaved pubes.
“I think you will find Jane is a very exciting woman. We were lovers a while back and are still firm friends,” Ada started to tell me, before the conversation was cut short when Jane arrived, the center of attention as she strutted through the hotel foyer, exuding self confidence and sex appeal, in her oversize shades, with her long earrings, she was a standout.
Ada and me both admiring the way she wore her knee length black skirt, with a long slit up one side. Her dark colour, double breasted blazer had me gaping, lots of bare flesh on show, making it obvious she was almost flat chested and wasn’t wearing a bra underneath.
Jane was sitting between Ada and me. Ada kissing Jane by way of greeting, before Jane kissed me. After a few minutes of small talk, while the two women crossed and recrossed their legs for me, or was it for each other?, Jane asked, ”Shall we proceed?,” holding our hands, turning heads as she led us to the elevators.
I was looking at Jane in a completely different light in the elevator with her new hairdo. Ugly, definitely not. Attractive to both females and males? Definitely yes, as I watched her and Ada kissing, their hands all over each other. An exciting woman? At that moment, very exciting for both Ada and me. Fuckable, most definitely. She had my cock reacting already.
“Did I forget to tell you Jane wants to have us both?,” Ada asked after we settled inside Jane’s suite.
“None of my lady lovers has ever been as good as you Ada, not one of them, you even know some of them,” Jane told her as they were kissing passionately, while undressing each other.
As I looked at Jane in a new light, she looked very fuckable, deciding I must have her. She was obviously proud of her forty-years plus, slim, shapely, body, good hips, a tidy taut ass, no dimples, a tucked in waist, a flat stomach, and by contrast was almost flat chested, with sexy, already erect nipples, with a small trimmed black triangle over her long, sexy legs. Her naked body had already given me a full on erection. So sensual, so feline, so fuckable.
Ada still had the voluptuous body of the paramour she once was, wonderful ripe tits, forty-two inch hips, a magnificent big ass and the easy confidence of a successful business woman and a bi-sexual lover.
I had only ever seen Ada giving cunnilingus to another woman once, a tongue fuck to remember. I can still recall the occasion, she was dynamite, the center of attention, so good, so talented while the woman’s husband and me watched. There are still rumours circulating about Ada’s cunnilingus skills, and the men who were willing to pay her large sums of money to watch her pleasure their lovers and / or wives before she retired to concentrate on running her escort agency.
Ada had Jane and me in her thrall as she licked her clit, “You were always such a good lesbian fuck for me Jane and you still are, tell me what you want, exactly what you want.”
I do like a woman who can articulate her sexual needs and preferences, Jane was nailing it for me. The sound of Jane’s beautiful dulcet voice talking dirty to Ada, her lesbian lover was music to my ears, soaking in her every word.
“Your tongue on my clit Ada. Like that, just like that. So good. So fucking good. Lick me. I love it. Fuck my cunt with your tongue. Like you used to. I love it. Love it. Fuckamycunt, fuckamycunt, fuckamycunt.”
Watching Ada and Jane showering together afterwards was a voyeurs delight, Ada preparing Jane for me, teasing her with lesbian, bi-sexual foreplay, Jane holding my gaze, looking at my erection all the while.
I had never had an assignment quite like this one. Jane, the woman who had paid Ada my agent for me to make love her, to fuck her, while being seduced by Ada my agent, two exciting bi-sexual lesbian lovers with no sexual inhibitions whatsoever.
Jane was incredibly exciting for me, as I licked and sucked her nipples as foreplay while Ada watched. I had to satisfy my ass fetish, worship Jane’s ass, a wonderful, tidy taut ass, no dimples, lick and kiss it while Ada watched her clenching her ass cheeks for us both. Running my fingernails along her ass cheeks, almost hard enough to hurt her. Then pinch her ass, just lightly, then a little harder until she told me, “How did you know I would like that? Pleasure and pain, I love it. Some more, don’t stop.”
Kissing and licking Jane’s ass some more while Ada watched, nipping her ass with my teeth, leaving a small mark, without any complaint from her. Ada was tongue kissing Jane while I licked her clit, already so wet for me.
Ada and Jane were kissing softly as Ada watched me sliding my rock hard erection into Jane. She had obviously never had children, her wet cunt lips were so wonderfully tight around my erection.
Jane was so articulate for me, talking dirty to me in a loud whisper, deliberately loud enough for Ada to hear, telling me exactly what she wanted. A huge extra turn on for me from such a formidable woman. “Fuck me, fuck me, fuck me with your big ten-inch cock. All the way up to your balls. I love it. So does my cunt.
Jane was a sex machine for me, a formidable sex machine. Her formidable demeanour a huge challenge for me after my initial reticence. I couldn’t have enough of her. The reaction of my cock confirming how much I wanted to fuck her and keep on fucking her.
She was a magnificent fuck. How could I have possibly thought initially she was an unattractive woman, close to ugly, with her dark hair parted down the middle? Naked on the bed with my cock in her as far it would go while kissing with our tongues she was magnificent.
Her confidence and charisma shining through as I Iistened to her talking dirty to me and Ada in her wonderful, dulcet voice while fucking her slightly taller than average, slim body with her expensive designer clothing scattered over the floor.
A little over an hour later Jane was sucking my balls, then sucking my cock, while Ada watched. “I promised you Michael could get it up two or three times in a session Jane. Look at the size of his cock, he is already ten-inches for you, and so thick. Are you going to give him a head job? Yes? Would you like me to watch? Naked? Both of you?”
Ada was standing behind me naked, watching Jane, adding another dimension to my head job. Teasing my nipples, running ice cubes over them, pinching them, pleasure and pain for me, just as I had done to Jane.
The two women were so comfortable with each other. Ada talking to Jane while she watched her giving me fellatio, a wonderful head job from a forty-nine year old woman, her experience shining through as she teased and edged me. Edging me to the brink of orgasm, again and again before Ada and me watched her swallow.
A few weeks later the business media were running stories about the high profile CEO of a major business organisation which was subject to a takeover bid and follow up stories about a middle eastern company who wanted to take a major shareholding in the company.
The same day Ada phoned me to tell me, “Jane wants to meet you again. She also wants you to meet the negotiator for a middle-eastern company she is having talks with. Does Friday night work for you?”Friday night in the Hyatt did work for me. A luxurious suite on a high floor with wonderful views over the city.
“Hello Michael, I want you to meet Omar, his middle eastern company is interested in buying a major shareholding in my company. You know middle eastern business men always expect some inducements. I want you to be part of my inducement and help me with the negotiations and convince him to invest in my company.”
When I settled down and focused Jane looked magnificent. Stunning make up, heels, a short, black cocktail dress with slits up both sides almost up to her armpits, obviously naked underneath. So sensual, and feline for two much younger men to admire and lust after.
Omar, the middle eastern negotiator was an exotic looking man around twenty-five, wearing traditional Arab arttire, a sparkling white. tailor made thobe, the traditional long robe, the top cut like a shirt, ankle-length and loose without any head gear. A completely new and challenging situation for me.
“I promised Omar you were well hung,” Jane told me as he watched her undress me while standing in front of him while he was sitting on a high stool. I always enjoy showing a new male my naked body and large, flaccid cock while watching their reaction.
Omar’s reaction confirmed what Jane had arranged for him was to his liking as I posed hands on hips for him. “Oh wow,” Omar moaned and smiled as Jane used her fingers to give me an erection.
“I want to fuck you while Omar watches,” Jane told me in her wonderful sexy, dulcet voice, the fuck word had never sounded better. I was sitting on a chair facing Omar when Jane lowered herself onto my erection, my fingers teasing her ass as she used me. Deliberately teasing Omar, “You could be arrested and even worse in your country for watching a woman my age fucking a much younger man. Do you like watching us fucking? Yes?”
“Do you like the way I shaved my cunt for you Omar? Just a small trimmed black triangle over my long, sexy legs for you,” Jane asked as she reversed her position. Do you like watching Michael fucking me this way around. He has the biggest cock I have ever had in me. He is huge and so thick.
“I promised you I would organise a western man with a huge cock for your sexual pleasure Omar. You have probably guessed Michael is bi-sexual, he is looking forward to receiving a head job from you while I watch,” Jane told him as she slid up and down my erection while Omar watched with a noticeable tent under his white. tailor made thobe, So good, an Arab man younger than me, watching Jane using me before she used two hands to masturbate me to a climax for Omar while he watched, the look on his face priceless and full of lust.
A little later Omar was watching Jane and me showering with his sparkling white, tailor made thobe resting on his erection. My gender-fluid side was looking forward to the excitement of a head job from an Arab man, five years younger than me. Aware that it was part of Jane’s negotiating tactics to obtain a better price from Omar.
“You are a sex machine Michael, look how thick and hard your cock is again,” Jane told me as Omar watched her wrap my cock ring around my balls. I was thick and hard for both Omar and Jane.
“Your big cock is magnificent, just fucking magnificent,” Omar told me in perfect Oxford English as he teased and licked my balls before Jane watched him lick, kiss and suck my erection.
“You could be executed in your country for doing that to another man. Sucking his cock like that. Does that make it even more exciting for you Omar? Yes?”
Omar was good, incredibly good and obviously very experienced with more than half my erection sliding between his pursed lips. Jane was standing behind me, kissing me over my shoulder, grinding her pubes against my ass, whispering, “Make Omar work for it, make him want your big cock even more.
“Michael is a wonderful challenge for you Omar. Look how big and thick his cock is for you? Do you want him to ejaculate for you? I do. He does. But not until I tell him. Did I hear you correctly, five for forty-nine per cent? And I remain CEO? Yes?”
I had my hands behind my head, wanting to maximise my sexual pleasure while I climaxed for Omar, Jane and me kissing with our tongues as Omar edged me, my knees trembling as I ejaculated in great gobs. What a woman, what a blow job!
In the afterglow Omar told us his negotiation skills had led him to expect and enjoy what Jane had organised for him, a male to sexually pleasure. The offer of a female as a negotiating tool had become common place.
So exciting and challenging for him, Jane and me, when Omar risked death back home for the thrill of giving another man a head job.
A week later the business media were full of stories about the female entrepreneur who had sold forty-nine per cent of her company for five million to middle eastern oil interests and remain CEO,.speculating about her negotiation skills. Urging other companies to chase middle eastern oil money.