Gary and Jane Go on Holiday Ch. 01

Story Info
Gary remembers the first date with Jane.
3.3k words
4.3
22.5k
32

Part 1 of the 15 part series

Updated 06/11/2023
Created 02/01/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
ColonelB
ColonelB
246 Followers

Dear reader. I have been reading the stories on Literotica for many years and now I have decided to join and write some of my own thoughts. This is the first part of the story of Gary and Jane. I hope that this will be the first of many episodes of their adventures together. Please feel free to leave any feedback, even if it is bad. I like to learn and know what people would like to read about. It is intended for an adult audience so if you are under 18 please do not continue reading. All of my stories will be about a married couple who love each other deeply whilst pushing the boundaries of their sexuality.

-----------------------------

Gary woke up to the amazing sensation of feeling his penis enveloped in someone`s warm and active mouth. It wasn`t just any mouth, as he easily recognised the technique of his wife of the last 10 years.

Jane was an accomplished protagonist of oral sex and she was proving this very aptly at this point. Gary lay there just enjoying the moment as he took in his surroundings.

They were in a large bungalow in a hotel Kenya, where they had arrived late last night, in order to celebrate their upcoming 10th Wedding anniversary on the following day.

At this point Jane withdrew his rapidly hardening cock from her mouth and gently stroking his shaft she slowly used just her tongue on the sensitive head paying special attention to the slit at the top where pre-come was already seeping out. She knew this would please him. Gary just lay back, enjoying the moment, and counted his blessings and his mind wandered back to how he had found this beautiful and sexual creature all those years ago.

Gary was a CFO at a very successful West End publicist and had worked there ever since graduating from University and had climbed rapidly to his current position.

Gary`s father was a successful lawyer in the City and the two had a very good relationship. This was mainly due to his mother dying when he was very young and his father taking on both parenting roles.

It was on one of his frequent visits to his father's office that he had first seen Jane.

She was sitting at her desk, her long black hair in a prim bun, staring at her computer through black rimmed glasses. She was dressed in a conservative charcoal grey suit with a pristine white blouse buttoned up to her throat. As she walked to a nearby colleague's desk he also noted the comfortable flat shoes and her straight trousers. Gary could see she was pretty but this "uniform" was designed to hide her figure and any femininity was seemingly suppressed.

She definitely did not fit into the category of any of Gary`s previous girlfriends who were 99% "short skirts, tits out and shag in the toilets" as his father liked to scold him.

Gary was now 26 and was starting to think about having a woman as a companion rather than a fuck toy, but as of yet he was unable to meet someone that he felt comfortable with, so it was just a case of a different warm body every Friday and Saturday night. He had plenty of options as he was a very handsome man with a body toned in the gym twice a week, plus he owned his own flat in West London and had a 6 figure income.

He glanced at Jane once more before popping his head into his father's office. His father was on the phone and mouthed at him to get a coffee and 10 minutes.

Gary knew where the breakroom was from his previous visits and quickly entered and pushed the necessary buttons on the posh state of the art coffee maker to get his desired cappuccino.

The machine finished and he took his cup and turned to sit at one of the tables and walked straight into Jane spilling coffee all over her brilliant white blouse.

He hadn't heard her enter as her flat pumps had made no noise on the thick carpet. Jane jumped and a small squeal left her lips as the hot liquid seeped through to the skin. Gary grabbed a cloth from the counter and without thinking started to rub at the soaked area which just happened to be Jane`s pert, more than a handful is a waste, breasts. She squealed again, but this time a little louder and Gary, realising that his actions were not very PC, turned bright red and started to apologise profusely whilst Jane also blushed a deep crimson but giggled and stammered that it was fine.

A few moments passed before Gary could speak. He offered to pay for the cleaning which was demurely declined and then he said at least let me take you to dinner.

Where that came from he was not sure and the pause that followed seemed interminable before Jane cocked her head to one side, looked him in the eyes for the first time and said "OK" very quietly.

Gary had plans with friends that evening and tomorrow was Friday so he offered Jane to meet in a Chinese restaurant that he knew was close to both his office and his fathers.

Her reply was that she would like to go home and change after work so could they do it later?

It turned out that she lived very close to him on the West side of London so they arranged to meet at eight thirty at a restaurant they both knew in Hammersmith. At this point she left the room to change into a spare blouse that she kept in the office, and Gary went to meet his father and to find out more about the woman he was apparently going to dinner with tomorrow evening.

His father was surprised by his son`s request for information but informed him that Ms. Jane Greenwood was a very good real estate lawyer that had been with the firm for nearly 3 years after graduating from Durham University. As far as he knew she was single, lived alone and was liked and respected by all of her colleagues. With that sparse information Gary left for his office, glancing once at the empty chair that had once held Jane, but who was obviously cleaning herself up in the toilets.

For the next day and a half Gary was trying to compose a plan to get the required meal and small talk out of the way and depart to some club in the West End. He could not imagine that this obviously introverted young lady would hold his attention for long and his chance of getting a hand job under the table were next to nil. He would however make the appointment as penance for the coffee incident.

The next evening Gary arrived at eight twenty as he was trained by his father that it is better to be 1 hour early as 1 minute late. He sat at the table he had reserved earlier and ordered a glass of White wine.30 minutes later he was looking with annoyance at his watch as it ticked towards eight forty five when the door opened bringing with it some cold air, the customary London raindrops and Jane.

Gary nearly had a heart attack there and then. Jane was dressed in a short leather skirt that came to maybe three inches above the knee. Her legs were encased in black nylon that Gary prayed were stockings. 4 inch heels added to her height. She wore a short cut leather jacket over a purple silk blouse with the top four buttons undone and her fantastic black hair was dropping free to her shoulders. Her makeup was subtle but the dark red lipstick complemented the black leather attire and the smoky green eyeshadow gave her a cat like appearance. Every male head, and some of the women, turned to take in this apparition oozing sex appeal as she made her way through the restaurant towards him.

Gary`s mouth still hung open as she apologized for her tardiness by saying that it took an age to decide what to wear.

Gary just about managed to stammer something about it being worth the wait.

After ordering a full bottle of wine of the same wine he had been drinking whilst waiting they ordered quickly.

For Gary the evening seemed to fly past as they talked about their lives, music, family.....everything. She was so easy to talk to and even if he occasionally glanced longingly at the silk wrapped breasts that were staring out at him from the open blouse it was the conversation that captivated him. His thoughts of making excuses and going to a club quickly disappeared as he was captivated by this wonderful creature sitting across from him.

One of the first things that Jane explained was the difference in wardrobe. She told him that her work persona and her private life were like 2 different people to her.

Gary could only mumble his approval whilst she talked and explained her strict up bringing by devout Catholic parents and her rebelliousness once she had left home to go to Uni.Gary nearly spat his wine over the stiff linen table cloth when she expanded this to say that this had led her to a sexual exploration were she had tried many things including women.

Her openness and frank way of talking just captured Gary from the first minute and he was already imagining spending the rest of his life with this woman. A feeling that he had never ever experienced in his life.

It was shortly after the "women" revelation that the waiter arrived to say they were closing and could they settle the bill.

Gary looked at his watch for the first time since Jane had entered and saw that it was nearly one in the morning. He was amazed, paid the bill and helped Jane on with her jacket. He didn't want the evening to finish so suggested they go somewhere for a drink.

Jane seemed to be enjoying the evening as much as him and readily agreed. The next question was where to go. Gary didn't want to go to a noisy club as he was enjoying their conversations.

Jane must have read his mind as she enquired how close his flat was.

Instinctively Gary hailed the next cab and less than 10 minutes later they were entering his flat with a view of the Thames. Thank God that Friday was cleaning lady day so the place was immaculate. Wine he enquired and she agreed with a nod. Gary left to get the bottle and 2 glasses.

On his return Jane had kicked off her heels and had those gorgeous nylon clad legs pulled up under her body sitting on the large 3 seat sofa that dominated the room. Jane really was a beautiful woman he thought to himself. Gary poured the wine and handed her a glass. They clinked glasses and each took a sip. Gary told her how much he had, and still was, enjoying the evening and Jane replied that she too had had a great time but now was the time for the finale.

Gary, thinking she meant that she was leaving could not hide his crestfallen expression which was greeted by the most exquisite and loud laugh he had ever heard from a woman.

I am not leaving silly she chided him and stood up.

Gary went to stand as well but she told him to stay seated.

She slipped back easily into her heels and walked across the room to stand by the picture windows. "Can you put some music on please" she said and Gary clicked the CD player on and Alicia Keys started to sing quietly from the two large speakers in the corners.

Jane started to sway to the music then slowly undid the zip on the side of the leather skirt, by breathing in deeply she allowed the garment to drop to the floor around her ankles.

Gary inhaled deeply as Jane stood there in a black suspender belt with little rose buds sown onto it, sheer stocking with lacy tops attached by four straps to the belt and the biggest surprise of all was the fact that she was wearing no panties.

Gary`s heart was beating and he could hardly breathe as he stared unashamedly at her naked pussy. Naked was the word as there was not one hair to be seen. Again he started to rise but was stopped by a hand movement from Jane that could only be interpreted as wait there.

The silk blouse was soon also deposited on the floor revealing a bra to match the suspender belt. At this point Jane turned to face the window away from him, stepping out of the clothes on the floor as she did this. Now she bent completely double and grasped both of her ankles giving him a glorious view of her now glistening and obviously aroused pussy.

Gary was unsure of what he was supposed to do until Jane informed him that he can do "anything" he wanted as long as he didn't leave the sofa.

Jane then used her right hand to slowly ease her labia apart and started to run her fingers up and down the crack. Once the wetness started to run down her legs to the tops of her stocking Jane started to rub her clit. Softly at first, but building up the speed and the hardness of contact until her legs started to shudder with the impending orgasm.

Gary couldn't take it anymore and freed his by now rock hard cock from his pants and started to jerk off.

Jane turned to watch whilst never stopping playing with her clit and occasionally slipping first one and the two fingers deep into her, by now, sopping cunt. As she came loudly, so did Gary. He shot large spurts of come all over the sofa and the floor.

He had never been so turned on in his life.

This only increased as Jane now crawled towards him on all fours and dipped down and licked all of his come from the wooden floor leaving it clean and shiny. She still wasn't finished as she climbed onto the leather sofa and liked that clean too. Finally she took Gary`s now flaccid penis in her mouth and licked that clean as well.

Gary really thought he had died and gone to heaven. Jane took Gary`s hand and led him to the bedroom. To cut a long story short they never left the bedroom for the entire Saturday and Sunday until Jane left for home at midnight. They tried every position known to man. There was oral, Anal, masturbation and even a little S & M as Gary had a slight dominant streak and, he discovered, Jane had a slight submissive side.

Through all of this and in the rest phases they talked. About everything, but especially about what they liked sexually and this just enhanced the compatibility for them both.

Every weekend was virtually the same for the next five months until eventually Gary popped the question and Jane eagerly agreed. They were married in the autumn and bought a very nice three bedroom house in West London with the proceeds of the sale of their two flats

Gary could feel his orgasm growing as his wife started to suck in earnest on his by now rock hard cock.

He tried to pull her up to him but she shrugged him off with a mumbled "This is payment for last night".

Eventually Gary could contain himself no more. The sound of the ocean plus the salty smells of Africa coming through the open double doors that led to the beach was too much and he shot his milky load into his wife's waiting mouth. She captured every last spurt but did not swallow it all immediately as was her usual custom but turned away from him to look at the open double doors and the ocean beyond.

Gary looking over her shoulder was surprised to see a girl in her early twenties standing there just staring at the sexual encounter she had just witnessed. Gary could see that she was white with long auburn hair a great figure that was enhanced by the tight bikini bottoms and cropped t-shirt that showed off her emerald navel piercing to perfection. She stood there in a trance like a deer in the head lights as she realised that she had been spotted.

Then to Gary`s surprise Jane opened her mouth wide showing the girl his creamy deposit before making an exaggerated show of swallowing it all.

Jane crooked her finger as if to say "come here" to the girl, at which her trance broke and she ran off in the direction of the beach.This had obviously been her destination before Jane distracted her with her oral skills.

They both giggled uncontrollably and Gary got up and headed for the shower. As the warm jets rained down on his body he smiled as he remembered the "Last night" that had required payment in the form of a fantastic blow job from his lovely wife.

They had caught a late flight from Heathrow to Mombasa that landed at two in the morning in Kenya.

Jane was wearing a very short denim skirt that Gary had insisted be worn commando. This was their Dom/Sub sides coming out.

Jane had readily agreed and as they cruised at 33,000 feet with the cabin lights dimmed Gary had edged his hand up under the hem and eased her legs gently apart and found her pussy with ease. He was slightly surprised that it was soaking wet and his finger glided in easily to be followed quickly by a second one.

It was only when Jane whispered in his ear that she had been anticipating this for one hour that he understood her apparent arousal.

They were still four hours from arrival so he took his time teasing her slit, rubbing and pinching, her by now, engorged clit and sliding one, two or three fingers into her wet cunt. As the captain switched the seat belt sign on indicating their decent into Mombasa Jane let out another deep sigh as orgasm number 6 hit her.

She was literally trembling as they arrived in baggage claim, grabbed their bags and went outside to find the pre-booked driver named Andrew. Luckily Andrew was there and waiting and they quickly stowed their bags in the trunk and left for the hotel which was about an hour away.

Gary made sure that Jane was sitting behind the driver and as they stared out into the darkness his hand started to play under the denim skirt again, with the desired effect.

Jane`s orgasm this time could not be stifled as she came loudly for the seventh time which brought a quizzical look from their friendly driver, but he said nothing and just continued to drive. On arriving at the hotel the check-in was fast and efficient and they found themselves in the most beautiful bungalow directly on the beach.

Jane couldn't wait any longer and stripped off her clothes and lay on the bed with her legs splayed in the most wanton display.

No red-blooded man could refuse that invitation and Gary`s hard cock slid easily into her demanding pussy. Unfortunately all of the foreplay had also excited him and after only ten or twelve thrusts he was spurting his seed deep inside her as her body shook with orgasm once more. They took a quick shower together and then they collapsed exhausted into bed. Snuggling up to each other and with Jane held tight in Gary´s strong arms they driffted off to sleep

ColonelB
ColonelB
246 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
9 Comments
26thNC26thNCabout 2 years ago

1 Star

Voyeur is a cuck

26thNCuck Disapproved

WargamerWargamerabout 2 years ago

Glad to hear it isn’t a cuck tale

I’ve enjoyed what l read so far, keep up the good work.

Scores 5/5/thus far

dannyboy1958dannyboy1958about 2 years ago

great so far looking forward to part 2.....

patilliepatillieabout 2 years ago

Decent start, hope you are submitting these daily as you have the story all written. Otherwise, readers lose interest and forget what has happened.

iameaseliameaselabout 2 years ago

Well for the record it was a decent tale.

Sadly as its your first story and you included this line in your prelude "All of my stories will be about a married couple who love each other deeply " which around here is generally the clue that a writer is setting up what we've all come to expect and its him diving into the deep end of the cuck pool and that includes wife sharing, as they are the same damned thing now. That line is usually there so the writer can fend off the readers who, correctly state, 90% of cuckings do NOT involve love or respect.

Keep it up but we'll see if you can keep from going where it always goes around here.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Neighbor Chronicles Pt. 01 Amber submits to the neighbor for her husband's fantasy.in Loving Wives
My Wife wants to Date Other Men My take on the "Honey we have to talk" story.in Loving Wives
Fallout 01: Wife's Office Party Wife learns hard lesson about cheating.in Loving Wives
Camping Trip Turns Wife Into Slut Wife turns into slut in the shower for big cocks.in Loving Wives
Wife Needs More Pt. 01 Lustful revelations ignite and transform a couple's sex life.in Loving Wives
More Stories