Chapter 1 - Him
David Collins arrived in his hotel room at about 7:30, tired as usual, all the more so because he knew that he had a good 2 or 3 hours of work ahead of him. It was always like this when he was away on business – he had become rather used to it and had ways of making it less exhausting but whatever he did he always got home totally shattered and tended to spend most of his weekends asleep.
On evenings like this there were a variety of things that he might do. If there was not too much pressure of work and there was something good on television, some top class football for example, he would spoil himself, order something from room service and just relax in front of the box.
More often he would have to settle down with the laptop, log on to his work email and work away for most of the evening before finally collapsing into bed. To cap it all off, no matter how tired he was he often had a lot of trouble getting to sleep.
Over heated hotel rooms, unfamiliar noises throughout the night and getting into bed with work on his mind would often conspire to give him a night of little if any sleep. Then up early and off for another day full of meetings, negotiations and make or break calls.
Tonight was different though. Tonight he knew that whatever his room was like and however tired he was, he would be unlikely to get much sleep.
Tonight was one of those deadline nights.
The meetings he had had today, with a new client, had thrown up a fantastic opportunity but one that he had to close off tomorrow or it would just pass him by. Worse than that – having risen to the opportunity, if he chose not to pitch tomorrow the client would have no regard for him at all and would be unlikely to ever work with him again.
So tonight he had to put together a pitch from scratch. From background research on the client he would have to decide his approach, build a presentation capable of knocking them dead, rehearse until it is word perfect and all just him and his laptop; no head office support, no teams of Marketing experts and no brainstorming sessions with experienced colleagues.
Just him and his laptop in a hotel room.
Well not quite. On nights like this he would call on The Executive Office - his lifeline and saviour in impossible situations. When it absolutely has to be ready for the morning, The Executive Office was the only answer.
His company subscribed to a service to provide secretarial support where ever it was needed- at a pretty high price mind you. After all we are not talking about your average Temp here but top grade Personal Assistants any time, any place. And tonight was one of those times.
David had phoned the service when he left the last meeting at 6:30 and arranged for their local representative to meet him at the hotel at 8:30. That left him a short hour to freshen up, sort his papers and thoughts and phone home. Of these the last was the hardest and most…well, saddening.
Phoning home should have been a pleasure, if tinged with a little regret at being apart. Instead it was an awkward and fairly pointless exercise. His wife, Susan, would be more interested in the Soap she was watching – or at least so it seemed, and would clearly not be listening to what he said and there would not even be a hint of emotion let alone love.
Anyway, that unpleasant task out of the way, David immersed himself in the powerful flow of the shower and let the steam and hot water wash some of the tension out of his muscles and freshening him up for the task ahead.
With 20 minutes to spare he put the last touches to his smart but rather more relaxed, evening clothes, having carefully hung his suit and put his trousers in the press ready for tomorrow.
On working evenings like this he preferred a formal shirt, but open at the neck with no tie, and a pair of neatly ironed chinos. A formal approach was not only his personal preference but was also required in the contract with The Executive Office.
Once dressed, 5 minutes sorting his papers, and he was ready to meet his assistant for the evening. Another requirement of the contract, representatives are were to be met personally at reception.
The Executive Office is a professional and totally above board service, asking staff to meet someone from a client firm in their hotel room might be misunderstood. This is no cheap and tawdry escort service providing “executive relief” but a valued and valuable support service to businesses where and when needed.
Straightening his tie, David closed his room door and walked slowly and thoughtfully towards reception.
He was concentrating totally on the work that had to be done, no thought about the person he was going to meet. No expectation of anything other than a job well done, no interest in whether she would be pretty or young or anything, just clearing in his mind what had to be done and how best to do it.
Chapter 2 – Her
Caitlin was exhausted as she got into to her flat, keys thrown on the sideboard, laptop in the corner, flicked off her black heels and then slumped straight on the couch. It was only 4pm, so this was early by her usual standards but it she had felt like she had done 2 days worth of work already! It was the Johnson account again today and one of the toughest clients of the company.
None of the other staff, senior or junior, would touch this account with there being two reasons why, ‘Ruth Johnson’. Ruth was the MD and a pretty tough business woman at that, though to give her credit she had to be to get to where she was today. On the downside she was always far too demanding, arrogant and just plain rude to anyone around her. This was even more apparent when the pressure was on.
Caitlin had sort of built a special relationship, or more like an understanding, with Ruth over the numerous times they worked together. There was no shouting or arm waving, just an itinerary and jobs completed. Caitlin was the only employee of The Executive Office that could handle Ruth Johnson or at least demand some respect from her. Caitlin, young as she looked always spoke louder with her actions rather than her words, needless to say the Johnson account always went her way.
Caitlin finally musters enough energy to get herself up, time to freshen up and unwind after the days work. A nice long soak in the hot bath was what was called for. Caitlin made for the bathroom and ran a hot bubbly bath, whist she slid out of the days black pin-stripped skirt suit. She unbuttoned her black blouse and rolled off her sheer black hold-ups, removed her black lace bra and panties in the bathroom and slid under the hot foamy water.
An hour later Caitlin emerges wrapped in a white cotton dressing gown all rejuvenated. She goes into the kitchen to look for a snack now she has found her appetite back. She opens a bottle of Rioja, pours a glass and takes it with some chicken salad to the couch and switches on the TV to catch up with the day news. On this particular night she is quite happy to spend the night in with her glass of wine and the TV.
6:35pm mobile rings, ‘Office’ shows up on the caller display. Caitlin didn’t really want too but had to pick up, work is work. Word from the office is there is a new account with a priority job on for tonight, and they need someone experienced who could deliver on it. “OK, email me the details” Caitlin replied. Caitlin picks up her email whist she towel dries her long dark hair.
Ref: 889563 Collins Account
David Collins
8:30 pm
Grand Hyatt reception
“OK, at least I have a while to get ready” Caitlin thought. Better go and choose something to wear. Caitlin opened her double wardrobe “Right, new account, better make a good first impression”. Caitlin picked out a nice red skirt suit that she wanted to wear. “Hmmm, better look nice but not too sexy” she thought, since it was an evening assignment with a male client she had not met before. She put the red suit back and picked out a light grey business suit instead, the skirt was a nice length just above the knee. What to go with it, black blouse? No too dark, and not black again! It had to be something light, a white blouse maybe, but white is so boring.
Caitlin liked to mix things up a little when working in the evenings. She had more flexibility as it were, since working in the evening mean that only a handful of people would see you, at the most! So it was less important to look strictly business-like. Caitlin picked out a particular white blouse that she would normally wear when meeting up with some friends for drinks. The blouse was quite vintage/Victorian styled and had a high buttoned collar and also slight ruffles on the cuffs. It was sexy and cute yet formal and presentable, just the job!
Caitlin laid her blouse on the bed next to the light grey fitted jacket and matching grey skirt. She strolled over to her chest of drawers and pulled open the top drawer. “Hmm, had to be white” she thought as the last thing she wanted was her underwear revealed through her white blouse. Her hands started flicking through the panties section first going through the whites: cotton, sheer, lace mini, lacy low cut French. Her fingers flicked over some satin.
“Ooh that’s nice” Caitlin thought.
She picked a pair out, they were white satin thong, they had a couple of pink satin bows on both sides and one at the back, but were a bit on the skimpy side. However she liked them and felt like wearing them so that was that. Caitlin looked for a matching bra and found a white satin bra, decorated with similar pink bows on the shoulder straps. Hopefully the pink bows weren’t going to be too much of a problem with the blouse.
Just before finding the matching bra set Caitlin also found a matching satin suspender belt. She had forgotten that this was a 3 piece set, and remembered that it was a present from a previous boyfriend that she didn’t really have time for due to work commitments, and never did get round to wearing for him. That was the downside of working for the high powered sector, you barely had time for yourself let alone any kind of relationship. There are only so many times you cancel on a date at short notice and still be in the ‘sweetest thing in the world’. Anyway, the suspender belt looked particularly cute being all white except for the little bows, and Caitlin thought it was going to look great.
Hmm, suspenders though to an evening assignment with a male client. This was defiantly NOT acceptable with the office. But hey, it was an evening assignment and they would not be there to check up on her. Caitlin just couldn’t resist, she picked out some silk nude coloured stockings from the drawer also.
Caitlin made her way to the dressing table in her bathrobe and began her routine of moisturising followed by applying her foundation and a light face powder. She chose a blue shade of eye shadow and worked in a lighter shade of blue and white being careful not to over do the make up. Caitlin applied a rosy blusher then chose a medium violet shade of lipstick, and finished off with a splash of lip gloss and black mascara.
Looking quite pleased with her make up Caitlin made her way over to the bed. Caitlin sat on the bed next too her office outfit, she was quite pleased as she knew it was just going to look great all together.
First she picked up her nude silk stockings which just seemed to flow across her fingers as she did so. She took one of the delicate stockings and rolled it together, then rolled the stocking over her foot, up her calf and then up to her thigh. Caitlin loved the smoothness and cool feel of the stocking on her smooth slender legs. She rolled the other stocking on and stretched her legs out as she sat on the bed, admiring her legs for a moment. It had been a while since she had last worn her silk stockings she thought to herself. Now with her stockings on, Caitlin picked up the matching suspender belt and wrapped around her waist and fastened at the back. She started to fasten the stockings to her suspenders, one on the front and one on the back for each leg.
Caitlin un-wrapped her towel and put on her white satin bra, fastening at the back and the straightening the shoulder straps. Finally, she took her white satin thong and slid those over her feet and up her silky legs, she loved the way they caressed her legs as they brushed over them. Caitlin stood up made sure her thong was on properly, adjusting the front and back so it was tight across her front making sure her modesty was well hidden. It felt a bit bare at the back but she liked it that way, especially if you have a good quality skirt next to your bare skin.
Once that was all done she walked towards the long mirror in the corner of her room. Once in front of the mirror she began to adjust the tops of her stockings, and straightened the suspenders making sure the fastening was on properly and covered by the little piece of satin so it would not protrude from her outer clothes.
Caitlin walked back over to the bed, and picked up the blouse she had chosen. She slipped her arms through and buttoned it up, all the way up the high collar. Next she slipped her grey skirt up to her waist, again the cool feeling of the skirts lining caressed up her legs and she liked that feeling. The feeling of the cool lining against her bare bottom also felt great. She fastened a button and a zip on her side and picked up her matching grey jacket. She slipped the jacket on and fixed the cuffs of her blouse so that some of the little white ruffles were shown out if her sleeves, perfect.
Caitlin opened her wardrobe door to look for some shoes to go with her outfit. Caitlin’s eye caught a pair of silver-grey satin shoes. They were a pair of round-toed satin shoes which had a wide satin ankle strap and a diamante buckle. The heels were 3.5” too so not overly high. Caitlin loved high heels anyway, they way they made her walk so elegantly and so sexy. Also the way they sounded as she walked, every step on a cold hard surface was like a musical note. This particular pair of shoes that Caitlin chose had previously been worn with long dresses to parties and was not part of her usual working wardrobe, but they seem to be just perfect for this occasion.
Caitlin took her shoes back to the bed, sat down and slipped the shoes on. She wrapped the straps around her ankles and fastened the buckles on the sides. The shoes felt so comfortable, and very expensive. Caitlin did have a weakness for nice (but expensive) shoes.
Caitlin stood up and walked confidently towards the mirror. She looked great, not over-dressed like for a day in a client’s office, but not too casual either. She especially liked the shoes she had chosen, it gave her a feeling like she was going out somewhere special rather to an evening work assignment.
Caitlin walked back to the dressing table to look for some accessories. Whilst doing so she decided to leave her hair down in her natural styled way. She chose a pair of drop down silver earrings, medium in length. A black choker caught her eye; the choker had a white porcelain broach that she thought would fit in with the style of her blouse. One silver bracelet with a heart, one spay of l'eau d'Issey. That should do, wouldn’t want to over do it.
Caitlin picked up her red silk clutch bag from the side and popped into it her essentials: face powder, touch up lippy, lip gloss and her credit card. She walked back over to the mirror to check her complete look, and was pretty satisfied with it. She turned around and bent over slightly to see if the top of her stockings showed, but luckily they didn’t. Perfect!
With time ticking on, Caitlin thought she’d better be off in order to be punctual which is always a sign of professionalism. She picks up her laptop bag on the way out and leaves her flat closing the door behind her. The Rioja will have to wait till she gets back.
Chapter 3 – The Grand Hyatt
Caitlin arrived exactly on time as she always did. She was dressed in a smart business suit, a well cut grey skirt just above her knee, a close fitting matching jacket that worked well with her slim figure without over emphasising her natural sexuality and a plain but crisp white blouse with a high neck buttoned all the way up with a choker on the outside with a simple porcelain broach.
She was confident that the look was right, The Executive Office were very particular about looks and asked to vet all their staff’s work wear. Particularly for staff like Caitlin.
Not only was she younger than most of her work colleagues, younger by some distance than some of the very capable but rather dried out matronly types that they liked to employ but she also had a look about her.
In all honesty she had had this look since she entered puberty. No matter how she dressed and no matter how little attention she paid to herself she had a natural, innate attractiveness. We have all met people like this - its impossible to define or distil it down to figure, or dress, body language or any one factor.
She is just very attractive.
So for her, working for The Executive Office in some of the best hotels in the country, in gentlemen’s rooms for sometimes many hours, was perhaps rather high risk. Except that she has never had any trouble being in control of any situation she has found herself in. It’s not as if she can turn off her sexuality, it would be easier to stop raindrops falling, it’s just that she seems to command respect and men just seem to accept that they must behave with the utmost professionalism when with her.
So, as she walked across the limestone flags of the large reception area, past the old, deep red leather sofas, punctuating the silence with the crisp clack of her heals, she was on the outside the picture of the office professional. Only she was privately aware of the near silent rubbing of sheer silk as her stockinged thighs touched each other ever so gently – almost a caress – with every step.
When she had left her car she had discretely checked herself and she was confident that everything was in order, suspender buckles – or anything else for that matter – did not spoil the straight lines of her skirt. She didn’t wear them for others, not to provoke a reaction, especially not in her client for the evening.
Like the plain satin thong she had on, they were for her. She simply loved the feel of expensive, simple but erotic lingerie.
The thong in particular felt delightfully; tight across her front, slightly constraining like a loosely cupped long fingered hand over her private and secret self; while at the back it ever so gently pulled between her haut buttocks which were free under her skirt, no lines to spoil their perfect roundness. Every step was a tiny pleasure, a private indulgence just for her; a small treat for having to work in the evening when she could have been curled up with glass of wine and a good book or luxuriating in a hot bath.
No wonder she had such a naturally sensual walk, with nothing touching her perfect bottom other than the smooth satin lining of her skirt.
As she crossed the lobby she noticed a reasonably tall middle aged man with an athletic build, just under 6 foot she estimated, leaning against the back of one of the sofas and facing towards the far side of the room. He seemed lost in his own private thoughts. A pensive and rather intriguing look on his face; he had the look of someone who was comfortable with himself.
As there was no one else in the reception she assumed that this was who she would be working with this evening. She walked up behind him.
“Mr Collins?”
He looked up and looked directly at her, eye to eye – fairly intense but not unfriendly.
“Yes, that me; you must be from The Executive Office.”
“I am, my name is Caitlin and I’m at your service.”
“Hello Caitlin, and thank you for being prompt; we have a lot to do before my meetings tomorrow. I’m David by the way – do you mind if we are not too formal.”
“Not at all, David”
“Here, let me take that for you.” David took Caitlin’s laptop case from her hand leaving her with just her small Chinese, red embroidered silk clutch bag. “Shall we go to my room and get straight to work or would you rather have a drink here first and I can quickly brief you before we settle down to the work proper?”
“As you like, David, you’re the boss.” Caitlin wouldn’t have minded a drink, having missed the Rioja she promised herself earlier, but was aware that this was not a social meeting in a hotel but a working assignment and as The Executive Office pays the best money in the market she didn’t want to do anything to compromise her professionalism.
“Well, I’ve been working for about 14 hours straight so I think a short break would be good and would give me a chance to give you an over view of the work in hand” David’s suggestion was music to Caitlin’s ears. David moved toward the hotel bar, leading the way across the reception area.
The bar was beautifully decorated like a library in a stately home, all deep leather sofas and book lined shelves all a round. They had managed to create quite a cosy atmosphere in what was a really large area. There were very few people there, perhaps four of five couples and a group that looked like your business trainees who were having pre dinner drinks.
David lead the way to a corner with two small sofas set at right angles with a low table in between; he helped Caitlin to a seat and put her laptop case beside her.
“Well, what can I get for you; I think I will be a glass of wine but please, have whatever you would like.”
“You know David, I think a glass of red wine would be just right but a small one please, we have work to do and I will need to drive later.”
“Of course; do you have a preference, I tend to prefer something Spanish but please, say if there is something else you would like.”
“Spanish would be fine, perhaps a Rioja”
David turned to go towards the bar and almost knocked over the waiter who had appeared behind him as if from no where.
“Oh, goodness you surprised me. Could we have a couple of small glasses of Rioja, 1997 if you have any.”
“Certainly Sir, charged to your room?”
“Yes in deed.” David handed his room card to the waiter and settled himself down in the other sofa near Caitlin with his legs almost touching. David passed Caitlin a single piece of paper that she hadn’t noticed him holding.
“This is the brief for the work tonight – we can talk it through after you have had a chance to read it.
David was feeling a little surprised with himself. He didn’t normally choose to drink with the staff from The Executive Office, indeed normally he would not want too. They seemed to specialise in the oldest and, well, least attractive, women possible – all very capable of course but nothing that would set a man’s pulse racing.
Caitlin however was different. There was a kind of understated sexuality about her. In fairness it was not that she was “obvious” in her dress or demeanour; she was not trying to be sexy or to play on her femininity it was just that she could not hide it.
She was the sort of woman that just made some men want to spoil them, look after them and get all protective and chivalrous. She had a beautiful, husky voice, almost deep; not too sultry but rather confident and self assured.
Although he had tried not to, he had noticed her lovely legs and how her high heels made her pert bottom demand his attention. She was sat now not 3 feet from him concentrating on the briefing with her legs, clearly silk covered, crossed and showing just a little above her knees. Not far enough for him to play guessing games but far enough to show that she really did own a pair of dangerously attractive legs. She should require a licence for legs like that.
DAVID – get a grip on yourself – you are here to work and have a vital and valuable brief to complete before tomorrow. Stop this lechery right now and focus.
Fortunately for David the drinks arrived and broke his daydreams; Caitlin finished reading the brief and took her glass from the waiter.
“Is there anything else I can get for you Sir?”
“No thank you; could you please get a couple of bottles of cold water sent to my room for me – as I will be working late tonight. And could you please ensure we have some privacy while we are here please.”
“Certainly Sir”
The waiter withdrew leaving David and Caitlin in the quite corner of the bar with no distractions or unnecessary noises.
“Well Caitlin, as you can see there is very little to go on. It’s a new client to me and I know very little more about them than the information you have there. My brief is to build a PR strategy and media management programme for then for the launch of a new product expected at the end of the month – only 14 days.”
“I have no specific details about the product but have been told that there may be significant negative public reaction to it, particularly from what they called “The Hairy Left” – whatever that is. I suspect that they are not a very pleasant company and I very nearly did not take the brief but sadly that is no way to may a mortgage.”
“What are your reactions to it.”
Caitlin was unsure how honest to be, was it really her place say what she really thinks? David’s openness and apparent honest swayed her. “To be quite frank David, I would have to agree with you – they don’t seem very nice but we don’t always get to choose our bed fellows. What specifically do you need to put together tonight and how would you like to do it?”
“OK, good for you – lets go for it. Firstly let’s finish these drinks and get to my room where we can work away in privacy. Secondly, I need to build a PowerPoint presentation as an overview of my strategy to deliver to their board tomorrow morning and a more detailed briefing document outlining the individual elements. This is the part that will take longest but I have done this sort of thing before so it is mostly planned out in my head anyway”
David stood up and picked up Caitlin’s laptop then offered her his hand to help her out of her seat. A gentleman, she thought – how rare these days. Just as well this is business and that there is a lot to do otherwise she might start thinking naughty and unbusinesslike thoughts.
Caitlin followed David across the bar and through the plushly carpeted corridors of the hotel until they reached his room. She rather enjoyed watching him from behind without him knowing – not a bad bum either!
He opened the door and held it for her to go in first, she turned sideways to pass him and in doing so accidentally brushed against him – really, it was accidental – or at least that’s what she tried to convince herself.
David in the meantime reacted as it he had been touched by a cattle prod and nearly jumped when she brushed past him – this was going to be a difficult evening. Caitlin looked positively edible as she walked away from him into the room.
David’s room was large enough for a small 5-a-side tournament – plus the spectators. Caitlin had been to some nice hotels in her time but this was something special. The room they came into contained a antique desk with a green leather top, a pair of small sofas with an occasional table and a curved arch into the sleeping area.
Through this Caitlin caught a glimpse of the most beautiful room she had ever seen. The bed was an enormous four poster on a raised platform with tied back curtains, there was a dressing table with mirror, a drinks cabinet with a leaded glass front and a couple of book cases with leather bound books in it. A small door in the corner opposite the entry arch, she assumed, when to the bathroom.
Feeling totally disinterested in work and more than a little goosepimply, Caitlin moved over to the table and started to get her laptop out of its case.
“I’m sorry,” said David looking a little embarrassed. “I should have said; the client is so concerned about “industrial espionage” – (total nonsense as far as I am concerned) that they insisted that all work is done on their own machine and have provided the latest wireless enabled model for our work tonight – for all I know it will regularly transmit a copy of what we are doing to their head office.”
“They really are a pretty cynical bunch aren’t they – I didn’t think that that sort of thing actually happens outside of films. Maybe I’m just a naive little girl – but I must say I rather my world to be blissfully ignorant of such nastiness.”
“I’m with you there Caitlin” said David taking her gentle by the elbow and turning her towards the desk – lets get on with this assignment from the company from hell and if we are quick with this we may yet have time for a quick glass of wine. For now though its water for me – how about you?”
“Mmm yes, I think I’ll join you.”
David opened a large bottle of sparking water, from the sideboard, that was glistening with condensation and poured to large glasses. Taking one over to Caitlin he put it beside the client’s laptop which he had set up earlier and sat himself on the sofa nearest the desk.
“Right. PowerPoint first I think.”
The next 2 hours passed very quickly with them both totally focused on the work in hand. Well, not quite totally focused; without realising it they each both stole occasional glances at the other and enjoyed private and slightly voyeuristic thoughts. By 11:15 they had broken the back of it when unexpectedly the phone rang, rather loudly breaking both their concentration.
“Who could that be?” said David more to himself than to Caitlin. “Excuse me a moment.” He picked up the phone. “David Collins”
Chapter 4 – An Unexpected Turn.
David hung up after just a few seconds, he turned to Caitlin with a slight frown on his face.
“I hope that this is not going to be a problem. That was reception to say that there was someone there with a package for me. It can only be this client as no one else knows I’m here – I’d better go and get it and lets hope that it will not require us to make any changes. Back in a minute.”
With that he picked up the room key and left in the direction of Reception.
As David walked briskly to reception he was wondering what on earth would be sent to him this late at night and what impact would it have the on the work already done.
There was no one in Reception except for a fairly tired looking man probably in his sixties.
“Hello, I’m David Collins – did you call me just now about a package.”
“Ah yes sir, the gentleman has gone back out to his car and asked that you join him.”
Rather unusual thought David but OK, lets just get this sorted and back to the work to finish. He walked out through the front entrance of the hotel and immediately saw a car parked, facing away from him about 20 feet away. The boot was open and there was a man in a suit bent over getting something out.
As David was a couple of feet away he introduced himself.
“I’m David Collins do you have something for me?”
As he arrived at the back of the car the man turned and stood up – David registered that he was bringing something round in his right hand and that he was wearing a mask. With the grace and strength of a natural predator the man held him firmly by the throat with his left and pressed the barrel of a stubby gun into the middle of David’s forehead with his right hand.
David was propelled back without either the grip slackening or the gun barrel moving. He was now walking backwards quite fast until his back slammed into the side wall of the hotel where it was recessed from the rest of the building and therefore in deep shadow.
“Don’t move” – pretty clear that; actually David had no intention of moving, the whole thing had happened so fast and so smoothly that he was really acting on instinct alone, no real thought process and right now the instinct was survival.
“You need to watch the company that you keep and be more selective when choosing your clients. Stay away from the filth that you met today – don’t complete whatever they asked you to do, go back home tomorrow and count yourself lucky that you’ve been given a chance.”
The static mask and complete lack of facial movement made the message that much more chilling. David had no doubt that this guy was serious. He had never been in this sort of position before – surely this sort of thing only happens in films.
Just as he was starting to get his thoughts together and regain a little composure – as much as you can when pinned by the throat with a gun to your head – the gun was removed, the man reached behind his back and brought it around again but the a small canister instead of the weapon.
Before he could react he was being squirted in the eyes, mouth and all across his face with a burning liquid. His head felt like it would explode and he could hardly breath. He bent over and the hand on his throat relaxed allowing him to fall to the floor coughing, gasping and in massive pain. He thought his chest was on fire, his eyes felt like they had acid in them and it seemed like his head would explode.
“Don’t worry its only pepper spray – you’ll be fine in 20 minutes or so.” With that the man stepped back and made to leave but then spun quickly round and drilled his right fist into the side of David’s face.
David rocked back against the wall, knocking the back of his head on the brickwork and collapsed barely conscious. He was bent double gasping and in pain all over, he heard foot steps retreating and car doors slamming and then the car calmly and quietly pull away. “Cool bastards” he thought, didn’t even feel the need to hurry away.
It took David at least 5 minutes to regain his feet and another 5 minutes to be able to move back towards the hotel. When he arrived the reception was empty, not that he really felt up to company or any great desire to share is pain and humiliation with the hotel staff. He realised that he really had no options, the Police would be no help and he was sure that professionals like this would have checked out CCTV cameras etc so leaving no trace or evidence.
As he left reception he suddenly thought of Caitlin – what would she think, he must have been away for some time, what of all her hard work and then he went instantly cold; he had heard more than one car door close but had only seen one person. Where was the other when he was being very professionally turned over?
He started running, unconcerned for how he looked or felt and ignoring the pain that short through his head with every step, he started charging through the corridors towards his room.
As he neared the room he felt some relief to see the door was shut as he had left it. He inserted his key card and opened the door. The room was quite and in semi darkness only faintly light by the light coming through the arch from the bedroom. The living area was empty, no sign of Caitlin anywhere. He moved cautiously towards the bedroom, his recent experience making him cautious where previously he would have been confident and self assured.
He walked to the middle of the archway and looked into the bedroom. The first thing he noticed was the papers scattered around the floor as if someone had just emptied a brief case from a height without any regard for the mess. Whilst he was taking this in he registered movement on the bed followed immediately by shock.
There was Caitlin, fully dressed but tied up and nearly immobile. She was lying on her side facing away from the doorway with her ankles and knees tied tight. Her hands were tied behind her back and connected to her leg ties. In her mouth was a tight gag, she was moaning and occasionally wriggling, as if she was testing the limits of her bindings.
David recoiled then rushed over to her side, sitting near her head he immediately untied her gag so that she could breath better. She gasped and drew several deep, desperate and somehow satisfying breaths.
“My God Caitlin are you alright?” she seemed to be near hysterical, her breath coming in ragged almost sobbing gasps. “Let me untie you” He reached behind her and started trying to loosen the on the knots on her wrists.
“No – please don’t. Undo my ankles first – they hurt the most” She sounded close to tears and near panic.
He stopped and moved down the bed and started working on her ankles. Once they were free he reached up for the knots on above her knees holding her legs together. As he did so she yelped and started panting in a rather desperate way
“Don’t worry I’ll have them undone as soon as possible just try to relax.”
“No, you don’t understand, it’s my ankles - they really hurt. Oh please help me.”
David stopped, and moved his hands back down her legs to her silk covered ankles and there he could see for himself the marks left from the ligatures and the laddering in her sheer stockings. The tightness of the ropes must have cut off her circulation and the returning blood was causing more yet more pain.
He gently took her left ankle in both hands and started to slowly and tenderly rub it; his thumbs massaging the front and the top of her foot while his fingers curled round to the back by her Achilles tendon and the bottom of her calves.
She gradually regained control of herself and started to calm down. Her breathing was still shallow but now did not have the panicky edge to it. Funnily enough to David it seemed to have more of an erotic and aroused sound. Caitlin was still weakly moving on the bed, slowly arching her back as she lay on her side and stretching her arms against their restraints – even this movement seems to have a sexual element to it.
Get a grip David he thought – what nonsense to think that she was aroused by this experience – the knock on his head must have done more damage than he thought.
He kept working on her ankles for a couple more minutes and then noticed that Caitlin was very lightly moving her thighs against each other, in fact he could hear the slightest sound of silk rubbing against silk.
She sighed slightly. “That’s really nice David but could you untie my knees now as they are hurting too.”
“Oh God, I’m sorry I quite forgot.” David settled a little further up the bed and worked the knot loose on the rope just above her knees, really at the bottom of her thighs. As he released the tension on the ligature Caitlin moved her left leg, the one on top, back a little opening a gap between her legs and allowing David to see the top of her stockings.
“Would you help with the circulation in my legs too please.” Caitlin’s husky voice now definitely had a sensual element to it. David could not help finding himself aroused and was himself thinking less than gallant thoughts as he slid his hands up her lower legs, over the smooth roundness of her calf muscles.
He moved both his hands on to her left leg just above her knee and gently started to ease the tightness there. He slowly moved his hands up her leg using little circular motions. He was now definitely enjoying the smooth feel of her silk stockings and was sure that she was experiencing similar emotions. When his hand reached the hem of her skirt, which itself had risen somewhat, he moved both hands over and started to do the same for her right leg. As he did so Caitlin moved her right leg forward widening the gap between her legs and causing her skirt to tighten across the top of her thighs; she whimpered and moaned clearly now. No mistaking it.
“Is this helping Caitlin?” he asked in almost a whisper, fearful that if he spoke too loud the spell would be broken and she would stop him.
“Oh yes, but please don’t stop; I need your touch and reassurance – I am still quite shaken.”
Caitlin then moved. David thought the worst but found that she was just getting more comfortable. She was now lying on her back with her arms still tied but underneath her now causing her back to arch and pushing her flat stomach and waist up and forward.
Caitlin’s legs were far enough apart now for David to move and kneel between them, still with his hands on her lower thighs massaging where the rope tie had dug into the flesh leaving clear marks.
He looked slowly up her body; her head was thrown back with her eyes shut, fluttering slightly and her hair dishevelled in a halo around her head.
Her chest was tight in her Victorian laced blouse and was rising and falling as she took little gasps of breath sending tremors all the way down her body.
Her skirt and risen slightly but he could no longer see her stocking tops. He could however see a noticeable bulge or mound at the front of her skirt a little above where the top of her thighs would be and thought that he saw what looked like a darker area in the grey material of her skirt; almost as if it was wet.
He could not tear his eyes from her, she was simply stunning; a picture in vulnerable, needful and hugely erotic womanhood raising all his manly desires to the surface in a breath-taking surge that caused him to gasp audibly. He wanted to lift her to his chest and hold her firmly but gently, stroking her hair and covering he neck with soft kisses.
Chapter 5 Confusion
This was a total surprise to him, not the reaction he was expecting at all. Until this he had admired her beauty but not felt any real desire or need in himself, almost as if he was looking at a work of art.
Its not that he was unmoved by beauty or that he was not attracted by women but in recent months there had been a significant change in his life. Something unlooked for, unusual and challenging. It had come out of the blue about 3 or 4 months ago when staying in another hotel somewhere, he had forgotten where.
He was feeling rather lonely and if truth be known a little depressed and when on the internet doing some research on a client he had accidentally come across an erotic fiction site – he didn’t generally look at pornography, although he was not prudish about it; but on this occasion he was in a strange mood and decided to explore a little.
When looking at the story categories he saw pretty much what he expected, teen stories, loving couples, a few gay ones, bondage – all the usual suspects. Then he saw something that he did not understand – transsexual stories. It was not a word he had heard before although with hindsight he could have worked it out. Anyway his curiosity was aroused and he looked a little further.
The story he looked at first was about a businessman in a hotel who picks up a beautiful woman in the hotel bar, is captivated by her and manages to draw her to his room where they start some pretty intimate foreplay. As they get more passionate and start undressing each other he suddenly discovers that she is rather more than he was expecting.
The story was illustrated with pictures of two gorgeous young models playing out the scene, step by step, touch by touch. When it came to the man’s discovery of the woman’s surprise and the accompanying picture, David found himself very aroused indeed. It shocked him; there he was a “normal” heterosexual male in his late prime, attractive to women and not unsuccessful with them, fascinated and sexually excited by…well…a penis. A very beautiful one it had to be said but a penis all the same.
David was stunned. He had never found men attractive before, indeed he was sure he still did not find men attractive but this was something different; it took his breath away. There was something about this that was not just attractive, it was absolutely irresistible. He was totally drawn to the images and to the story.
That night he revelled in his new found interest. He surfed for hours, reading story after story and finding websites, contact areas – a whole world that he did not know existed. He had never been this turned on in his life and masturbated until the morning light started to creep around the curtains and the morning bird song began in the manicured gardens outside.
Over the next few months David’s interest developed into a grand passion. He passed through times of denial – sometimes for a number of days – but always back to the same fascination. He came to accept that this was perhaps a natural part of him; something in his hard wiring. Not gay – although it caused him to reappraise his opinions and be more understanding – and definitely something in the context of great and intense femininity but something so much more powerful that his interest in “ordinary” women.
So it was in this context that David found himself aroused to the point of loosing his breath as he gently and tenderly caressed Caitlin’s legs. Now he really was confused as he had felt no feelings like this for women since finding his new passion.
These thoughts were all running around in David’s head as he gently and sensuously rubbed the front of Caitlin’s thighs up to the edge of her skirt – but not beyond. Caitlin groaned and seemed to wince.
“Could you do the backs of my legs please as they still hurt.”
“Of course, why don’t you roll over.” Caitlin did; rather awkwardly as she still had her hands tied. David didn’t move to help her and she didn’t ask for assistance or for the rope to be untied. David somehow understood that she did not really want them loosened, that she was actually rather enjoying them.
As she settled in a comfortable position she slightly opened her legs again and again David knelt between them. This time they were not parted far enough for the skirt to be tight across her legs.
David began to gently massage her thighs again, first one then the other, moving up her legs and stopping slightly higher each time. Now he was rubbing where he skirt met her stockings, now his fingers had slipped smoothly under the edge of her skirt and even onto the bare flesh of her upper thighs.
Caitlin was near panic. She had never been this aroused before, so turned on that all common sense and logical though was pushed from her mind. “What am I thinking, this can not be happening, I must make it stop – oh God please don’t stop.” Caitlin had never ever allowed herself to loose control like this. Never when working for The Executive Office, not even when she was out with her girl friends.
His hands were just so good.
She had been really caught off balance when the thugs had crashed into the room shortly after David left. One pinned her to the wall face first while the other tied her up. They had very quickly and efficiently searched the room, spilling the contents of David’s brief case and then had left as quickly as they had come taking with them both her laptop and the one that David had been given by the client.
She was still in shock when David returned and found her and really not thinking straight. Why she had not immediately let him untie her she didn’t know and that is really what had led to this terrible and fantastic situation.
Being tied up but with gentle hands working her tender muscles was a feeling beyond simple pleasure; a delicate balance between restraint, loss of control and eroticism. She had been close to climax a couple of times already and what was worse, she thought that David must know this.
But it had to stop – she must not get caught. It was beyond what The Executive Office would think, beyond loosing her job – she would easily get another one. It was far worse than this…it was the discovery of her secret.
For a number of year now Caitlin had enjoyed playing the part of a demure but sexy office girl, had even relished the reactions she sometimes caused – always in control of course (until tonight). The reality, however, is that Caitlin herself had only existed for a few years. Caitlin wasn’t simply Caitlin.
Caitlin was really a man. No, that’s not tight. Caitlin was all woman, very much so, just look at David’s behaviour. It’s just that Caitlin lived in a man’s body. Caitlin, whilst curvy and beautiful and feminine and alluring also had the “extras” of a man.
It is very hard to explain, even harder to live with. This body, this person only really came to life and lived in full colour, surround sound and high definition when Caitlin was allowed to flourish.
And now it was all at risk and might all be discovered. But still those hands were on the back of her thighs and moving higher and higher. “Oh God please don’t sop”
Caitlin was now making very quite noises in the back of her throat – as if she was trying to stifle her moans. David’s hands now seemed to move of their own accord, his thumbs between her legs almost up to her bottom, his palms passing from her thighs onto her bare buttocks. All pretence was gone now, Caitlin was clearly moving her hips up and down as it making love to the bed.
“Please…oh my God…please, yes…oh help me. STOP. Oh please you must stop.”
David stopped immediately.
Caitlin felt a deep loss. “He stopped !”
“Please, David; would you just hold me for a while. Just wrap me in your arms and hold me.”
“Of course I will – I’m sorry I really am – I have taken advantage of you and I feel ashamed. Please forgive me.”
David moved next to Caitlin and gently enveloped her in his arms, stroking the back of her head with his right hand and softly pulling her head down to the top of his chest. Caitlin tentatively snuggled into him and slightly lifted her left leg so that his right leg could move forward into a more comfortable and more intimate position between her thighs.
Caitlin sighed – more relaxed this time and less sexually charged.
They lay like this for some time – it seemed like hours to Caitlin but was probably only minutes feeling very comfortable with each other; physically close, more controlled and less edgy.
“David, this can’t happen. I’m sorry that I let it begin.”
“I know, you have your work to think of, it was wrong of me to take advantage of you like that and put your job at risk too.” David was struggling to say the right thing – his mind was resisting, wanting it to continue.
“No, David, you don’t understand – its nothing to do with work – it’s me, totally me. You don’t know me – if you did you wouldn’t want me. You would reject me anyway so its best if it just doesn’t start.”
David pulled back from her so that he could see her whole face better. “What nonsense are you talking about? I can not imagine anything that would cause me to do that.”
“David, I’m not the sort of girl for you, please just accept that.”
“I’m sorry but your going to have to do better than that – if it was the work I would understand but this…this is not on; you’ll have to explain.”
“Oh David, don’t make me do this.” David was silent, just looking calmly at her. “Oh God David, I’m not like other girls – there’s more to me, a surprising amount more David……how do I put this; Caitlin is just part of me. There is another part of me too – a …..male part.”
Caitlin turned her eyes down, she couldn’t look at him any more. She was braced for his reaction. He started shaking slightly, then rather more, gradually it took over his whole body and then it happened.
David burst out laughing, he leaned his head back and almost howled at the ceiling. Caitlin was shocked; definitely not the reaction she had expected. She didn’t expect his next action either.
David leaned towards her and took her chin in his right hand. He lifted it up turning her head upwards so she had to look at him and he kissed her fully on the lips; fully and deeply. Once she got over her shock she softened and allowed him to capture her mouth and tongue; then her neck, her ears, her nose and cheeks.
He released her chin and ran his hands hungrily over her back, up to the sensitive skin of her neck under her hair and back down to the base of her spine where the welcoming roundness within her skirt drew him as if magnetically.
After an age he pulled away from her. “Caitlin, you are everything I have ever wanted – no wasted extras – whole complete and beautify.”
Chapter 6 – Naughty or Nice
Caitlin shuddered, she felt a wave of relief wash over her – immediately followed by concern, a different type of concern. Until this moment the Caitlin side of her had been limited to her working for The Executive Office – she had found years ago that a PA of the standard they required really had to be female due to old fashioned and close minded thinking.
That was not why Caitlin was “born” – she had always existed – but it was the extent of her public appearances. Caitlin had never actually “met” a man and certainly not been intimate with one. Oh, she had fantasised many times and many different scenarios and had very strong desires, even longings, for Caitlin to become a complete woman but had never really thought that it would happen.
Now, because of the violence and physical threat of the thugs tonight and the care and tenderness of David, she found herself on the edge of being able to complete herself….and she was nervous; more nervous than she had ever been in her life.
What would it be like, would she enjoy it, could she give pleasure to a man, would her dreams remain in tact or, by the end of the evening, would they lie broken on the floor. She had never felt more vulnerable, more exposed and yet more excited and aroused.
What was more, her hands were still tied behind her back and she could not even return the embrace, could not touch or stoke this kind and gentle man!!
“David?”
“Yes Caitlin.”
“Could you undo my hands please?”
“Oh my God, I’m sorry I have forgotten…..and anyway I thought you were rather enjoying them being tied.”
“You are right of course but I really would like to be able to touch you – if you don’t mind that is!”
David moved away from her and gently turned her onto her front. She looked beautifully vulnerable lying there with her head turned to one side, her hands behind her back and her skirt halfway up her thighs revealing her stocking tops and suspender buckles.
He put his hands on both of her elbows and slowly drew them down towards her hands, took her wrists firmly and slightly lifted her arms up and off her bottom. He removed his left hand and stroked her bottom through her skirt, underneath where her hands had been and then round and down the side of her left buttock and gently down the side of her thigh.
He let go of her wrists and now moved both hands to her thighs below her skirt hem. Caitlin shivered and sighed. As he moved both hands up her legs together, lifting her shirt and exposing the bottom of her buttocks he spoke to her.
“And what if I didn’t choose to untie you? What would happen then?”
Caitlin replied but her first effort came out as a croak, her throat was so dry and she was so…coiled… that she had to lick her lips and clear her throat.
“Well, I suppose I would be totally in your control and I would be unable to stop you from doing anything you wanted….I would of course be unable to touch you and make you feel good.”
“All in good time, all in good time.” Was his rather cryptic reply.
He hands had now reached the top of her thighs and his thumbs were right at the base of her bottom where her thong disappeared between her rounded buttocks. He widened his hands and started to push the material of her skirt up the front of her legs.
Caitlin, understanding what he was doing, pushed down with her toes and raised her midriff off the bed so that her skirt now smoothly rode up over the front of her thong to settle eventually at her waist.
“Good girl, now you seem to understand.”
David was now able to admire the full beauty of her rounded bottom unobstructed by skirt or underwear. He sat back on his haunches and openly admired her. She pushed her bottom up in the air displaying her self in a very obvious and provocative way.
Then he knelt down and ran his open hands over her buttocks pushing them apart and exposing her thong nestled in between; as he separated her cheeks Caitlin pushed herself up off the bed widening the gap and fully exposing the rose of her bottom to his gaze.
David, fascinated by the sight, found himself drawn down until his lips brushed sensuously across the skin of her checks passing over the crevasse in between to grace the other side. He had never actually consummated his desire for “the third sex” as he had seen t-girls described and was entering new ground but it all felt so natural and comfortable. To have said that he was aroused would be a massive understatement – he was harder than he had ever been.
He was now placing tiny and delicate kisses across her smooth skin, occasionally nibbling and teasing her with his teeth. Caitlin moaned again and slowly rotated her backside causing his face to pass across and enter the musky heaven of her private and virginal sanctuary.
David gasped and flicked his tongue ever so quickly and boldly across her rose bud tasting the earthy promise of her sex.
He could hold back no more. He reached up and nearly ripped the ties off her wrists, releasing her hands and almost throwing himself up the bed he took her in his arms and kissed her deeply and passionately. Now released Caitlin was at last able to hold David and express some of the pent-up emotion she had.
She put one arm between them and explored his muscular chest enjoying the feel of his strength and masculinity, her other hand reached behind him and moved across the expanse of his broad back. As she moved it down she clawed her hand and allowed her nails to mark their course through his shirt causing him to arch his back and draw a sharp breath.
Meanwhile both David’s arms are behind Caitlin’s back and he slowly lowers the zip on the back of her skirt. Rather pathetically he tugs at each side of the now open zip trying to remove the skirt but to little effect. Caitlin lifts her hips and she herself helps to take the skirt down as far as her knees from where he manages to take it off.
Having helped with this she takes her hand off his chest and releases his belt and zip to start removing his trousers. It is now his turn to help so he raises his thighs and allows Caitlin to remove them with a few extra kicks to help. They now face each other with just a thong and a pair of briefs between them.
The impact of what could be about to happen seems to hit them both at the same time and the urgency is replaced with caution laced with anticipation.
They kiss again, less urgently but more intimately, exploring each others limits and gradually raising the temperature of the contact. Their legs are now intertwined with David’s right thigh pressing between Caitlin’s legs and rubbing against the front of her thong causing her arousal to increase and encouraging her to thrust back against him.
They are both aware of each others arousal, of the prominent bulges in each other’s underwear and of how much that turns them on. Next, David slowly and gradually rolls further over until he is between Caitlin’s legs, taking most of his weight on his knees with his firmness pressed against Caitlin’s front reaching towards her stomach and pushing against her own obvious excitement.
They push against each other, still passionately locked together. Then, as if by some unwritten agreement, David draws back slightly and Caitlin pushes her hips further back into the bed so that they disengage.
David takes the opportunity to move slightly down and then push forward boldly. His proud manhood, still encased in his briefs now pushes against the string of her thong and touches her eager rosebud.
“Oh God yes.” Caitlin can not stop herself, all reserve gone and feeling as wanton as a £30 tart, almost desperate to accommodate and satisfy her man, to take him, envelop him and to revel in his masculinity.
“Oh Caitlin, I want you so much. Are you ready for this, really and honestly?”
Caitlin pulls back from David and looks at him, with a slight smile and then an impish grin she nods. “Don’t you try to stop me now – just you dare. But before we go further…shouldn’t we be safe?”
David gets up and goes through to the en suite where he has left his toilet bag. He comes back after no time holding small box in his hand which he puts on the table beside the bed.
He bends over Caitlin and kisses her lightly on the lips. As he is bent over her she reaches up with her left hand and takes hold of the top of his briefs. .He stands up but she doesn’t let go. She pulls him towards her in the process pulling the front of his underwear away from his stomach.
David’s manhood, which is standing strong and proud almost leaps out, a very visible symbol of his state of arousal.
She pulls the material down and takes hold of him with her other hand, at the same time swinging her legs off the bed and sitting upright on the edge. She is totally focused on David now as she starts to move her hand steadily, exploring his length and increasing his arousal.
She can’t take her eyes of him, not because she does not want to make eye contact but because she is completely fixated on what he has to offer. For the first time in her life she grips and stimulates an aroused man and gets a real buzz out of the obvious pleasure that she is giving.
She gently pulls back his foreskin exposing his deep red end which is already lightly lubricated with his juices. She finds herself moving on the bed, squirming in her own arousal and with anticipation for what she hopes will come.
Caitlin stands up, still holding David, so close to him that they are pressed together along their whole length. She can feel his freed cock against her belly and can feel herself straining to be released. David puts one arm around her waist and with the other traces a line down her stomach, over her suspender belt and to the top of her tiny thong which is trying and failing to restrain Caitlin’s secret.
David points his hand down and presses it against her willing midriff enabling him to slip his fingers into the front of her thong. Caitlin stands frozen with anticipation and he tentatively and tenderly touches her. She almost jumps at the first contact, then relaxes as he touches her again and then wraps his fingers around her.
He bends down and kisses her in the corner of her neck where it meets the top of her chest; she leans her head back revelling in the moment. David starts to move his hand up and down her length, she matches the movement on him. With his other hand he takes her thong down and lets it fall to the floor.
She puts one arm around his neck taking some of her weight as she lifts her right foot off the floor. She lifts the leg, bent at the knee and curls it over his left hip and around above his bottom, still holding him with her other hand. She stands on the toes of her left leg and at the same time pushes his erection down until she can place it between her legs so that the end is touching her just below her rosebud.
David starts to gentle trust his hips backwards and forwards simulating sex and rubbing his sensitive end across the smooth and shiny satin of Caitlin’s thong. She responds by leaning up and kissing him passionately on the lips, moaning into his open mouth.
David is now gripping Caitlin’s engorged clitty and rubbing her rhythmically as he continued to push himself between her legs. His other hand moves down off her waist and curls over her buttock with the fingers exploring the exposed, hot and sensitive skin around her puckered ring.
She is very aroused and sweating freely but he is surprised at how moist she is and he is able to easily slip his middle finger into her love channel – she gasps and almost looses her footing at the wave of pleasure that washes over her. David kisses her deeply and passionately.
“Oh my God, this is amazing, too much” She is now sure that not only does she want to loose her virginity and consummate her feminine side but also that she will and that it will be tonight, with David.
Chapter 7 Coming of Age
Caitlin is lost in a whirling storm of rising passion. She does not know what to do; David’s hard cock is firmly planted between her legs as if she is riding it, her bottom is on fire with his middle finger stimulating its entrance and he is gripping and stroking her hardness all at the same time.
She literally does not know which way to turn.
She desperately needs to gain some control over both herself and the situation or she will be spent, literally spent if this goes on much longer.
Caitlin reluctantly pulls back from David and breaks their kiss, she lowers her right leg back to the floor and David moves his hands back to her waist, he still has his manhood firmly lodged between her legs.
“I’m thinking that you seem rather overdressed” said Caitlin putting both her hands on his chest and starting to unbutton his shirt. As she undid the last buttons she ran her hands back up over his exposed chest and pushed his shirt back over his shoulders and down off his arms.
There he stood now, naked in front of her. She lent into his body, placing her nose almost on his skin and inhaled deeply. She held her breath momentarily and then exhaled in one long go, slightly ruffling his chest hair as she did.
David also unbuttons Caitlin’s blouse and pushes it back off her shoulders until it falls down her arms to the floor, leaving her with a white satin bra that matched her thong, both with little pink bows.
Caitlin then sat back down on the edge of the bed, took hold of David’s manhood in her right hand and looked up to his face. Looking at each other eye to eye she slowly dipped her head forward and slightly opened her mouth until he was just about to enter her. David involuntarily closed his eyes, leaned slightly back and pushed his hips forward.
Caitlin closed her lips over the end of his cock, creating some resistance for him and using her lips to push his foreskin back. As she did this he felt the moist warm heat of her mouth envelop him, increasing his arousal even further.
Gradually she took more and more of him into her mouth, when she was comfortable she started to move her head backwards and forwards, slowly at first and then with increasing speed.
She liked the feel, a sort of spongy firmness with a slightly salty taste. Most of all she liked the effect it was having on David. His eyes were still tightly shut and his face had a look of intense pleasure. He was very definitely moving his hips, towards her and away from her, exaggerating the movements she was making with her head. One of his hands slid to the back of her neck – not to force her head forward but to gently stoke the soft hair where her head and neck met.
Caitlin could not help herself. With her free left hand she reached down between her own open legs and started to stroke her balls, lifting them and touching the smooth skin underneath them and then reaching further through her legs to the very sensitive area around her virginal anus.
“Oh Caitlin, that’s fantastic, oh wow.” David was clearly very much enjoying himself. “Oh God, stop, please stop or I’ll cum.” Reluctantly David pulled back away from Caitlin and she let him withdraw although she would have been happy to take him to completion.
David bent down and started to kiss Caitlin on the mouth, tasting his own saltiness on her and finding it rather erotic. He took her by the shoulders with both hands and firmly pushed her back onto the bed without breaking the kiss.
He moved around until he was between her legs which were wide apart like a love struck teenager wanting her first man – indeed that is exactly how she felt. She could feel his thighs pushing her legs apart further and felt a thrill at the prospect of satisfying him as well as some anxiety about the act that would surely follow next.
David broke the kiss and moved his mouth down to the base of her throat leaving gentle little kisses on the soft skin at the top of her chest. At the same time he reached down with his left hand and started to stroke her firmness, as hard as it had ever been, and willing in his hand. She started to move her hips in time with his hand.
His mouth moved further down her chest, over her bra and on down to her belly. He flicked his tongue into her belly button giving her the feel of butterflies in her stomach right down at the base of her hardness.
He then dipped his head further and took her into his mouth, returning the favour, moving his tongue up and down its length and taking her as far into his mouth as he could without choking.
He did this for a few minutes, teasing her from her smooth balls to her sensitive end. Just as the pressure within her was rising to the point of no return she felt something cold and wet between her buttocks as his fingers started to explore her bottom. Initially surprised and confused, she realised that this must be some jelly or lube of some sort.
It was only now that she realised that it was really going to happen, she was really going to take this man, to envelop him, bring him into her and allow him to penetrate her. She was not frightened, a little nervous perhaps, but was keen with anticipation. She felt an ache inside her bottom; an intense desire to be taken, filled and completed.
David lifted his head and body up, letting her fall out of his mouth. He leaned forward, keeping his hands on the edge of the bed and his arms hooked behind Caitlin’s knees. This pushed her legs back with her knees coming close to the side of her chest. Of course it also raised her bottom invitingly and totally exposed her rosebud to him.
Feeling delightfully vulnerable and totally ready for his, Caitlin smiled at David. “Yes David, I want this, I want you. Please be my first.”
David leaned even further forward and to her great pleasure she realised that they would be able to kiss like this – she had always felt a little saddened that if she lost her virginity doggy style she would loose all the intimacy of the moment as she would not be able to see her partner.
She felt something hard and slightly cold and wet touch her anus. David had somehow managed to put on a condom and some lube while he was giving her the blow job. He pushed against the resistance of her, he pushed firmly not accepting the resistance.
Initially it hurt and she thought she would be too tight but she relaxed a little and all of a sudden David’s end was past her entrance and was in her. She felt a great fullness and an intense pleasure and he gently and smoothly entered her to his full length.
So this is what women feel. No wonder they like it Caitlin thought. She was feeling wave after wave of pleasure as David started to build a rhythm.
He was now standing upright, which had eased the pressure on her hips and legs a bit. She could see him standing erect before him as his cock pushed repeatedly and deeply into her. She was now lifting her hips with his rhythm taking him as far up her as she could. She hooked her heels behind him at the base of his back and encouraged him further.
On her belly her cock was hard as steel. David reached down and took it in his hand stroking it in time with his thrusts, he was now also grunting slightly with each movement. Both he and Caitlin were sweating freely.
“Oh God Caitlin, you’re fantastic, amazing. Does it feel nice? I’ve always wondered.”
Caitlin laughed – as best she could in the circumstances. “Nice? It’s fucking wonderful but I want you to cum. I want to totally satisfy you, to leave you spent deep inside me.”
David increased his pace, slapping his balls against Caitlin’s bottom, then after a couple of particularly deep thrusts he pushed really hard and then froze as far into her as he could get and sighed as his cock spasmed and he came. Even though she knew he was wearing a condom, Caitlin could swear that she could feel him come and felt intense satisfaction.
David leaned forward again and kissed Caitlin fully and deeply on the lips. After a few minutes he started to soften and eased himself out. There was a moment of soreness as he withdrew which was totally dominated by the feeling of satisfaction and completeness. She was a virgin no more, she had fully come of age.
Caitlin rolled over on the bed giving room for David to lie beside her; he snuggled up next to her and enveloped her in his arms pulling her close. He kissed her again, less passion now but more intimacy.
“Thank you Caitlin. That was fantastic but I fear that it was a little one sided and you have not yet come.” Indeed between them there was now a different position from the one a few minutes ago. Where David was now soft and sated, Caitlin was still hard and unrequited – and prodding into David’s stomach.
“Well I hope your not going to fall asleep on me just yet.” Caitlin joked.
“Weeell” teased David shutting his eyes and pretending to snore.
Caitlin agilely grabbed both of his wrists and quickly turned on him pinning his arms above his head and sitting astride him with her erect sex like a flag pole between them. David started to wriggle under her and apply his own strength, Caitlin soon found herself in a weak position when sitting so upright so she lay flat along David’s stomach and tried to pin him down like this.
They playfully struggled with each other for a few minutes, Caitlin then ended up between David’s legs which had parted in the mock fighting. David had freed one of his hands and was tickling her mercilessly causing her to wriggle about a fair amount.
They both seemed to realise at about the same time that this had caused Caitlin’s hard clitty to push between David’s buttocks.
“Oh, goodness me, you are hard still – that must be rather frustrating for you.” David started to move his hips a little making Caitlin rub against his bottom. “Mmm, that feels good but its not really what I had been expecting.”
“Have you tried that before.”
“No, Caitlin, you are my first and I have never tried that with anyone before. Is it something you want to do?”
“Well,” she teased, “with you vulnerable like this it is tempting…but I hadn’t really thought about it before. I am still coming to terms with being in a feminine role – and really loving it I must say.”
David gently pushed Caitlin off him to one side so that she lay on her back.
“Don’t worry about it just now, enough new experiences for one night but I can do something about this.” David had taken Caitlin in hand again and was stroking her back to maximum hardness.
He moved down her body and for the second time that evening Caitlin found herself in his mouth, with his tongue working wonders on her, tantalising her and bringing her up to new heights of arousal.
She could feel the pressure rising in her and she was openly thrusting herself in and out f his willing mouth.
“Oh God, I’m going to come.” Her head lifted off the bed so that she could see his head bobbing up and down, her hips pushed forward suddenly and quite beyond her conscious control, she grabbed either side of his head and simply exploded in his mouth.
Her orgasm seemed to roll on and on until it finally stopped and she lay back, exhausted. As her breathing started to return to normal she realised that David was again cuddling her and holding her close.
It was like this that they both fell to sleep, content and spent on top of the bed in his luxury hotel room. How would they both react in the morning, how would they feel in the cold light of day?
That will have to wait. For now they are happy with their dreams.
THE END ?