driving-miss-willoughby
CELEBRITY STORIES

Driving Miss Willoughby

Driving Miss Willoughby

by eloquentman
19 min read
4.74 (13900 views)
adultfiction
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*This is entirely a work of fiction. Any names used beyond the well known celebrities are chosen at random and do not represent real life individuals.*

*****

After an unexpected and rather wild twenty four hours looking after Carol Vorderman, Jack's life as a an executive chauffeur (his notional job title, though he was in fact a full partner in the business) had taken an interesting turn. Firstly, Carol had been true to her word and had shared with her celebrity friends her discreetly edited take about how Jack had rescued her and whisked her away to an awards dinner, but also hooked her up with an amazing dress from Miss Carlotta's boutique, both businesses were busy with celebrity patrons.

Jack heard about the comings and goings at the boutique from his regular catch up with Audrey, who not only worked there but was also a part of Jack's ongoing complicated love life. Usually on a Thursday evening where they had dinner with him and his girlfriend Angela, and more often than not, a long evening of fun frolics as a threesome. She sensed rightly that Angela paid more attention to these stories than he did, but descriptions of top television and film stars in various forms of lingerie were pretty entertaining. Carlotta had shown her thanks to Jack in a more practical way, firstly by letting Angela shop there with a very nice discount, but also by making sure that if a client needed a driver that his name was the very first to be mentioned, and it ensured that their burgeoning executive car service was doing rather well.

It had led to a rather long and complicated conversation with Julia, who though now married very happily to Natalie (his solicitor), still enjoyed an occasional "naked board meeting" with him. In truth he was always up for sex with Julia and occasionally Natalie together, after their epic trip to America when Jack's enhanced physical capabilities were extensively tested by the pharmaceutical company who had originally treated him for a urological condition. The treatment was completely successful, but had unexpected bonuses of doubling his penis size and gifting him exceptional sexual stamina, as well as producing vast amounts of pheromones when he was aroused. Which often led to some wild and unexpectedly fun sexual encounters.

It did help to explain as to why Jack had a beautiful girl friend that he lived with, as well as a handful of wonderful friends that they both regularly fucked. Complicated, unusual but all involved would tell anyone that they were very satisfied with the situation.

The other factor in the growth in demand for specifically Jack's services, was a picture of his erect cock that Holly Willoughby had snapped and shared round a very discrete circle of friends. Her domestic arrangements included a free pass for fun with her friends and selected invitees at her London flat. She was undoubtedly a doting mother and wife, and played those roles to perfection, but in addition her sexual needs went beyond the capabilities of her husband, and his choice was to allow her to express herself discreetly. They were on occasion hinted at such as on her appearances on Celebrity Juice, but she and her PR machine very carefully managed her image to perfection.

Out of the spotlight, Holly was a bisexual submissive, with an almost limitless well of sexual desire. That inner circle of friends included less well known names such as her PA and her stylist, but ones that were much better known such as Davina McCall, Fearne Cotton and Kelly Brook. From time to time they would add one to their circle, perhaps a professional dancer from the Strictly Come Dancing series or an actress from one of the soaps. Regardless all were sworn to secrecy and agreed to provide pictures or evidence that would have career ending consequences if any of this were ever to leak out. None of that was ever needed, and the ladies enjoyed access to a wonderful time spent with each other, and the occasional guest.

Once Jack's picture had circulated round the RF Club (now called the Recreational Fucking Club after a comment Jack had made to Carol the morning after their first meeting), bookings were in high demand, though as of yet, nothing beyond his professional services had been requested. Jack was perfectly fine with that, but in the back of his mind he knew that there was inevitably more to follow.

That happened on an evening recording of Celebrity Juice, where Jack was to collect and deliver Holly and Carol from her discrete London apartment, and be on tap to take them home after the recording. The pick up was routine with Jack lugging garment bags and a couple of small suitcases to the car, while Carol and Holly chatted over a hot beverage. He returned to inform them he was ready to depart when they were, and went to return to the car when Carol stopped him.

"It's our fancy dress special tonight Jack, and we might have an extra guest to bring back with us. I take it that will be okay?"

"Of course, though if there is any body paint or the like then I've a blanket in the boot to sit on to protect the seats. Please just let me know if we have a third passenger, I'll be very happy to accommodate them."

That just brought giggles from both women, which was the first of a number of hints that this was not going to be a vanilla pick up and drop off evening. They grabbed their coats and while both were stylishly dressed, it was a casual and comfortable look under long jackets when they stepped into the car. Jack knew the route to the studios well, and they arrived comfortably on time.

When they arrived, Carol and Holly were met by a production assistant who greeted them warmly, while Jack got the luggage from the vehicle and followed them inside. They made their way through a maze of corridors and arrived at named dressing rooms, with Jack depositing each woman's items accordingly. He saw Holly's PA, a young woman in her early 20's named Rachel and she waved at Jack, and after making sure Holly was happy with her set up, came out of the room and escorted him to the craft services area, where there were snacks and beverages available. Rachel told him he could wait here during the recording, and after moving the car to a suitable parking spot, he returned inside and helped himself to a nice cup of tea and a scone.

He settled down to relax, knowing that the recording might take a couple of hours, unlike the final edited version. He still wasn't sure who else might be on the show, and was mostly focussed on catching up with messages and emails on his phone, while occasionally glancing at the monitor showing the set.

He heard a hubbub down the corridor and saw the guests making their way towards the stage. Carol was in a very form fitting sparkly dress and long purple gloves, and an enormous red wig as she had chosen Jessica Rabbit for her costume, and was filling it out nicely. He was certain Carol was using some of Carlotta's now legendary lingerie to support her beasts, which seemed to be swaying along of their own accord. It took a decent amount of self control to not sit there open mouthed and drool at this vision, but the smile and wink from Carol caused an immediate reaction in his crotch.

Next to appear was Holly, who was rocking a very sexy Harley Quinn look akin to that shown off by Margot Robbie in the recent movie. The tiny shorts and stockings showed off her long lithe legs, with little boots on a 4 inch heel accentuating everything, her hair was tied up in bunches and had a the customary blue and pink colour through it, but the tee shirt with "Daddy's little monster" was struggling to hold in Holly's boobs, and her nipples were clearly visible even at 10 to 12 feet which had Jack wondering if they might need to do something about that in the studio. Holly completed the illusion in passing, by shouting at Jack in a pretty decent impression of the character.

"Hey Mr J!"

Of course Jack was thrilled at this, and his cock grew even larger at the thought of possibly having Jessica Rabbit and Harley Quinn to play with later. He was still unclear on who the mystery third guest might be. He thought it highly unlikely to be a man, given the circulation list of the picture of Jack that Holly had sent out, but was still unsure. He got his answer a few moments later when he saw a completely outrageous sexy schoolgirl strut - that was the only way to describe it -down the hallway. 6 inch heels were topped by black hold up stockings and a tiny tartan mini skirt so short that he could clearly see the gap at the top of the stockings. On top was a white blouse tied off to show the mid-riff and barely holding in a very large pair of breasts, topped off by bright red lipstick and heavy but not excessive eye make up. There was no mistaking the incredibly hot Kelly Brook who was turning heads with every step.

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Two things occurred to Jack in that moment. One, he was a ridiculously lucky man to be that close to her in real life, with his cock pretty much now fully and uncomfortably erect in his trousers. The second was a flight of fancy that wondered if she might be the mystery extra guest? His heart was thundering in his chest at the prospect, but just about managed to retain a cool veneer until she passed, though it didn't stop him from watching her sway her hips as she walked away from him. She paused, turned and looked over her shoulder and gave him a big wink, then made her way to the studio.

Rachel planked herself down beside him.

"O.M.G. If that isn't the sexiest woman on the planet then I don't know who is. Holly is fabulous, and yes I've seen her naked and she is utterly gorgeous, but gosh that would give you a heart attack."

Jack agreed, and pondered if Rachel's interests were in women as opposed to men. He took a moment to look at the young brunette, who was slim and rather pretty, but most importantly seemed to be very organised and totally on top of making Holly's life easier. It was routinely Rachel that booked him for the car service, and so they had spoken a number of times, but this was the first that they had actually met. They got chatting and Jack enjoyed hearing about her work and escapades working for a very well known TV presenter.

"Holly is totally sweet and wonderful to work for but you need to be available at the drop of a hat and always have her schedule up to date. She pays well, but let's say there are a few nice fringe benefits..."

Jack paused and briefly wondered where she was going with this.

"...like the RF club. You couldn't organise Holly's life without knowing about that, and she's generous about letting me join in sometimes. Like the staff party that's happening tonight."

Jack head was spinning at this point. Rachel knew about Holly's secret sex life, but that sort of made sense. How could you get hold of Holly at little or no notice unless you knew where she was going to be? Staff party though, what was that about?

"Jack, I've been asked to see if you would like to join the staff party back at Holly's place tonight? Of course Holly and Carol will be there, and they're hoping to have Kelly come and join us too. Then there's Sarah her stylist, Greta her make up artist and little old me. Drinks, nibbles and some party games. How about it?"

Jack pondered only for a second before accepting, and made sure to message Julia to let her know he and the car would not be available until the following afternoon. He then spent 10 minutes on the phone to Angela trying explain what was happening.

"So you've just been invited to a party with Carol, Holly and a bunch of women? We kind of knew that this was on the cards Jack."

"Yeah I know, and although I don't think they'd drop the service if I said no, I'm treading a delicate line here. Oh and there's a chance we might be joined by Kelly Brook."

There was a few moments of silence at the other end of the phone.

"Lucky bastard! Dammit she's on my free pass list too you know!"

Although neither Jack nor Angela had actually come up with their free pass list, as in truth both were free to express themselves sexually with whoever they wanted as long as they told each other about it after. Both however had made admiring noises about the actress/model on a number of occasions, so it made sense that Angela would be a little jealous at his possible opportunity. She told him to have fun and that she would see him whenever he surfaced, but to remind him that Debbie was coming over that evening.

"I promise I'll take good care of her Jack, so don't worry about me finding something to amuse myself with tonight."

Jack knew that Debbie and Angela shared a close bond and would undoubtedly spend almost the entire evening fucking each other until they were unconscious, so had little doubtthat his girlfriend would be properly entertained. They said affectionate goodbyes and Jack sat back down with Rachel.

"Your girlfriend? That is one very understanding woman you know."

He did indeed know, and they made small talk for a few more minutes.

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"You know they've got about another 45 minutes or so before the interval. How would you like to pop into one of the dressing rooms and have a lie down, take it easy for a while?"

Rachel was unambiguously squeezing his cock through his trousers, so Jack didn't think that taking it easy was going to be the plan. They waited for a quiet moment, then Rachel led him back along the corridor to Holly's dressing room, which had a large couch in addition to clothing racks and a large lit mirror. Rachel closed the door and turned the lock, before pouncing on Jack, engaging in a long and enjoyable tongue led snog. His jacket was pushed off his shoulders and the tie ripped from his collar. He reciprocated by removing the light cardigan and unzipping the skirt so that it fell around her feet.

Jack immediately noted the absence of any panties and that she was wearing hold up stockings. She carefully but quickly unbuttoned her blouse while he shed his belt and trousers. They stepped apart briefly, Jack noting and admiring the small but perky breasts that were now on show after Rachel shed her bra, quickly removing his shirt so that all that remained were socks and his black silk boxers, a luxury for sure but it was one he was accustomed to and as he was packing more than average in that department, very little off the shelf was comfortable. Rachel wasted no time in pulling the boxers down and letting his cock loose. She paused, admiring it in the flesh for the first time, then pushed him onto the couch and set about licking and sucking his cock.

Rachel was enthusiastic but only able to manage a few inches in her mouth, which seemed to frustrate her. Jack pulled her up from her knees beside him and they kissed more, then he worked his way down her body, getting very happy sounds as he paid attention to her firm and sensitive nipples. Jack parted her thighs and kissed and licked his way all round her pussy, before starting to thrust his tongue in and out, supplementing this shortly with a couple of fingers while he teased her clit.

"I've heard you're a legend with your tongue, but we only have a little time and I want to feel that monster inside me."

Jack needed no further invitation, and sat back on the couch, his cock pointing skyward, Rachel straddled his lap, and carefully positioned his cock at her now rather wet pussy, and lowered herself so the first inch or so was inside her. She let out a shuddering gasp as she felt the breadth of Jack's member, but only paused briefly before edging slowly until she was appropriately half way down his length.

"Of fuck that's all I can manage for now, it's so bloody thick. Maybe later I'll try again, but just let me enjoy this for now."

Jack was doing nothing to rush her along, and let Rachel edge up and down slowly until she was comfortable enough to get a decent rhythm going for herself. He made sure he was doing plenty other things to help her along, so played with her nipples, let his hands explore her body and generally made sure that she was having a great time.

Rachel was working towards what appeared to be a nice orgasm when they both heard a key fiddle in the lock of the door, which immediately froze them both in place. The door swung open, however they were largely obscured from the corridor by the open door itself. In strode Holly and a couple of women who glanced over at the couch, but paid next to no attention to what was going on. The door swung shut, and Holly swung around in the makeup chair staring straight at Jack. Rachel had buried her face into his shoulder, so all that could be seen was the star and what Jack presumed were her make-up artist and stylist mentioned earlier.

"I see you couldn't wait for the party Rachel...you naughty thing! Well don't let us stop you darling, we've got a thirty minute technical break while they fix... something, so at least we'll be entertained while we wait."

Holly was practically licking her lips watching the naked pair on her couch, whilst her companions seemed surprised but not shocked.

Rachel raised her head and turned around to face Holly, who merely smiled and told her to get on with it, as waiting like that wouldn't be good for either of them! Jack, who'd been in more than a couple of unusual sexual encounters in the last year since his surgery, shrugged his shoulders and tweaked a nipple to rouse Rachel back into action. She resumed her thrusts up and down, but Jack sensed she was quite disturbed by the interruption.

"Holly I think Rachel needs a little time out, and possibly to be told that she isn't getting fired for this."

"Oh good lord no darling. I honestly don't mind that you decided to amuse yourself with Jack while we were shooting, but I think he's right, take a moment for yourself. Now I have to go back on camera, and frankly everyone will know I've been a naughty girl if I go back out there after a quickie in here...but perhaps since Sarah's work for the evening is done she might enjoy it?"

The tall willowy blonde to Holly's left was perched on the corner of the desk, and was impeccably dressed. Stylish blouse, long skirt and heels, all perfectly accessorised with bangles and a large sparkly watch. Jack correctly guessed this to be Sarah the stylist, who was completely focused on Jack as Rachel clambered off him and pulled on her clothes, still rather flummoxed at the turn of events. Jack's cock seemed none the worse for the interruption and still bobbed in his lap at full mast.

"Fuck him Sarah, but I want to see your face as he fills you up. It's a divine experience darling, and I haven't seen someone do that for the first time."

Sarah nodded at Holly and unbuckled a large belt, then unzipped and slid her skirt to the ground. Jack noted again no underwear (and briefly pondered of this was a RF a club thing), and locked eyes with Sarah as she strutted across the room towards him. She pivoted and turned to face Holly, but bent over so her torso was almost parallel to the ground, and pulled back her cheeks to expose her pink pussy. Jack grasped her hips and guided her backwards, until she felt his cock pressed against the entrance of her pussy. Sarah guided him inside, very slowly, and although Jack couldn't see her face, he heard gasps and moans that usually indicated a very pleasurable experience. He could see Holly's face though, and she seemed fascinated with Sarah's experience as she impaled herself on his cock. The other woman who Jack hadn't been introduced to yet sat there slack jawed as the whole performance proceeded.

"Oh Holly fuck me it's so big, so thick... I thought you had to be exaggerating when you described Jack to us, but if anything you've undersold him."

"See darling I don't disappoint! Don't worry about making the most of this. Jack has amazing staying power and recovers like a horny teenager. But we're going to put that to the test later. Now Jack, let's see you give Sarah a good time."

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