Generation of Tarts Ch. 01

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Andy's fascination with older women gets closer to home.
5k words
4.39
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Part 1 of the 4 part series

Updated 10/07/2022
Created 11/18/2011
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This is the first story I have written. It is fiction, unlike other authors who will try and kid you that their tale is true. I hope you'll forgive me if this one is a bit of a slow burner. I often find that the build up to a sexual experience is as exciting as the experience itself. Stick with it and there is 'action' before the end of this episode, and the next episodes will get to the 'action' quicker, I promise. I hope you enjoy my story and feedback would be great.

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Andy had just finished the second year of his Sports Science degree at College. While he wasn't muscle bound, all the work he put in training and at the gym gave him a fine physique. He was putting that to good use during the summer break by doing gardening work. He hadn't been able to get a regular job during the Easter holidays and friends and relatives had helped out by suggesting he do garden maintenance for them. As often happens he was recommended to other people and gradually he was picking up more work. He was now doing the equivalent of about three days a week, and that was about right as far as he was concerned as it gave him plenty of time to relax and loaf around.

Relaxing is probably not the best way of putting it. He spent long periods in his bedroom, fantasizing about what he would do to his College girlfriend who lived at the other end of the country. He also spent plenty of time surfing for porn on the net. Either way, he was giving his prick a good workout by wanking, generally two or three times a day. He had become quite expert at sniffing out videos on the net that fitted his fantasies. Gradually he had developed a taste for watching videos of mature women in their 40's and 50's getting fucked, and if they were wearing kinky underwear so much the better. The minimum requirements were stockings and suspenders with high heeled shoes..

Even the thought of seeing an older lady dressed like that made his cock twitch and he had even begun to check out the women when shopping in town. The more attractive ones, those wearing a dress or skirt he would fantasize about. imagining what they were wearing underneath. In his mind's eye he saw a wonderful view of an exposed pussy framed by a garter belt, the suspenders and stockings.

The images in his mind would often start with the pussy being engulfed in a mass of curly pubic hair, but rapidly the vision would change to his favourite image where the pussy was clean shaven and the lips were distended by age and overuse so that they hung down, providing an exciting prospect for him to suckle on and nibble. He would then imagine his tongue sliding up between those gorgeous flaps to toy with the lady's clit, swirling his tongue around it in circles and flicking at the button. This he imagined would cause the old dame's juices to flow for him to lap upon, giving him the impetus to delve further up her love tunnel, flicking in and out, mirroring the thrusts of a good stiff cock.

He was in the process of daydreaming such a scene, his cock twitching and rising to attention, when he vaguely heard his mother calling him from downstairs. That was one of the problems of living at home -- the loss of privacy and ability to do just what you want, when you want.

The summer temperatures were pretty high, and even if the sun wasn't out he preferred to wear as little to cover his body as possible. So he was wearing a fitted singlet that clung to his abs allowing his relatively muscular physique to be seen. The singlet finished just above the top of his denim shorts, which he had cropped from an old pair of jeans. They we equally tight fitting, but that was good as it helped to prevent him getting caught up in bushes when he was pushing his way through shrub borders when gardening. His outfit was completed by a sturdy pair of suedette finished boots that extended above his ankles.

After a pause, in which he attempted to move his cock into a position where it wasn't too obvious, he ran down stairs to answer his mother's call. That was a mistake. His cock slipped from its 'concealed' position set vertically behind the zip front of his shorts and slid down over his left thigh. It was a good job he had not been fully erect or his helmet might well have pushed itself out of the leg of his skimpy shorts. As he reached the bottom of the stairs he met his mother who was coming to call him again. They met while he was still three or four treads from the bottom of the stairs., so her face was more or less level with his cock. As he carried on down to the floor level he noticed his mother staring at the bulge in his shorts with a slight smile on her face. Her eyes were clearly devouring the scene, and she even started to run her tongue around her lipstick coated lips. All this was momentary before his mum seemed to recover herself and moved away into the kitchen.

She started to talk to him over her shoulder but Andy wasn't paying too much attention -- he was admiring the rear view of his mother. She was dressed ready to go off to work at a local bank, and was wearing a grey hounds-tooth check pencil skirt that reached down to several inches below the knee. The skirt followed the lines of her hips and was cut to be fitted over her thighs and legs. He noticed that the skirt had a slit up the back to above the knee line that helped her walk easier in the fitted garment. As she walked her hips swayed in that arousing fashion that happens when a woman is wearing high heels, and the heels of the black court shoes she was wearing were certainly higher and more slender than was practical for a day in the bank where much of her time was spent on her feet. Her legs were encased in sheer black tights. He assumed they were tights, but he couldn't be sure. On her upper body she wore a silky white shirt together with a wide black patent belt.

Andy watched closely as she walked into the kitchen. The heels caused her hips to sway in a most sexy and suggestive manner, the sexiness was heightened by the 'clack -- clack' of her heels on the floor tiles, combined with the 'swish' as her hosiery rubbed against the lining of the skirt. Andy new it was wrong, but he couldn't help getting turned on and his cock took another jump as it became harder still.

In the kitchen his mother turned to face him and Andy was treated to a full frontal view. The silky shirt was quite fitted and clung to his mothers curves, becoming a little more tight over the swelling of her breasts. She had undone the top couple of buttons to show a good deal of cleavage. But for whose benefit? -- not for his surely? His mother's tits looked pretty full, but then she was obviously wearing a push up bra as her boobs were pushed together creating a deep cleavage. She looked fabulous -- for a woman of 45 she had a great figure which Andy fully appreciated.

Her outfit was stylish and sexy, causing Andy's cock to twitch and try to rise further up in his shorts, but it had difficulty doing so because his shorts were pretty tight. As a result he was becoming a little uncomfortable, to the extent that he had to turn away and go into the hall. There he pushed his hand into his slip briefs and adjusted the position of his knob, to make it more comfortable. Touching his cock was not the best idea and he struggled to resist the temptation to give it a couple of strokes. He got it back into the vertical position where unfortunately it caused his zipper to bulge out, If he became any harder he was sure his helmet would start to try to escape above the waistband.

When he returned to the kitchen his mother obviously caught sight of his bulging shorts, as she stared momentarily, and a half smile crossed her lips again. But she immediately composed herself and began to tell Andy what she'd like him to do.

"I've been clearing out your fathers wardrobe and sorted out a couple of bags of stuff your Gran can have for her church bazaar on Saturday. It's been three years now since Dad died and keeping his clothes in the wardrobe isn't going to bring him back, much as I'd like it to. In fact I've been thinking lately that I should be getting my life back on track, I've got plenty of years left yet and don't want to end up old and lonely."

So that was probably the reason for the sexy attire, Andy thought, "She's got her eyes on a guy at work, that's probably why she's wearing black tights on a hot day like today." He also realised that she worked in an air conditioned office so the outside temperature wouldn't make any difference to her. As much as he was pleased that his mother was thinking ahead, he was also upset that it wasn't him she was lusting after, although he new that was a ridiculous notion, he was her son after all. "Oh, well," he thought, "I can still dream".

"I know you're working over in the Devonshire Way area today. That's fairly close to your Gran's house. Would you be a darling and drop these bags off at her house?"

"OK." he said, cheerily enough to hide his recent disappointment.

"You'd better take the spare key, in case she's out, I wouldn't want you to have a wasted journey."

Andy took the keys, and while he did toy with going back to his room to have a wank while thinking about his mother's sexy outfit, he knew that his mother would encourage him to go to work straight away, and that was really the sensible thing to do. He would then be able to get in a couple of hours work before the sun became higher in the sky and the temperatures rose.

After about three hours work in the garden, the sun and temperatures started to irritate Andy and he decided to take a well earned break. He went to his beaten up banger of a car and settled in the front seat with a flask of coffee and a sandwich, and also got a magazine out of the glove box. Andy had responded to his growing appreciation of older women by buying a soft porn magazine with stories and pictures of mature women in their 40s and 50s. He read a few of the readers letters which started to make him horny, and he started to massage and rub his cock through his shorts as he flicked through the pictures of the various 'girls'

He had already established his favourite, and he lingered over the pictures of her wearing stockings and suspenders with a black satin corset. The cups had been folded down to expose her ample tits, which must have been at least an E size and due to their sagginess flopped down over her corset. She must have been at least 60 but Andy found the images very erotic and he couldn't help sliding his hand inside his shorts to give his cock a good rubbing. He gave it a number of strokes, which made it harden considerably and it would have been so easy for him to increase the tempo to bring himself to orgasm.

He was sorely tempted but realised that if he came he would be very messy with little available to wipe up his come. That would make him uncomfortable for the rest of the day, and he still had to go to his Gran's. There might be stains on his clothes that she would see. So he reluctantly put the magazine away and decided that he would be best to go to his Gran's now before returning to do some more gardening. She lived only a few streets away so he didn't think it would take him long.

As he drove the few hundred yards, in his mind's eye he continued to imagine the photos that he had just been looking at. The woman named as 'Dolores' might have been a bit on the old side but she still looked pretty hot. His thoughts turned to how he had clearly developed a 'taste' for older women, and thinking about this maintained his boner of an erection. On reflection he even thought his Gran was very attractive for her age. She was in her mid sixties and still had a good figure, with no obvious signs of spare tyres, muffin tops or the like, but then she had always tried to keep herself in trim. In her younger times he knew she had been a keen cyclist. Now she participated in gentler activities such as yoga, Tai Chi and a little gentle Pilates.

When Andy reached her house he parked on the drive, got the two bin bags out of the boot, and let himself into the house using the key his mother had given him, shouting out to his Gran at the same time. Within a few moments she called back that she was in the living room. Andy went in, to find his Gran coming to meet him. That was how they managed to end up face to face only a few feet apart. Andy's cock was still straining at the zipper of his shorts as a result of his daydreaming about 'Dolores' and a single look at his Gran did not result in a slackening of the pressure as might be anticipated, it only lead to his cock becoming more engorged. Now it was fighting to work its way above the waistband of his shorts.

"Hello ...... Andy." Her voice faltered and seemed to get stuck in her throat as her eyes could not help but focus on the bulge in Andy's shorts. She seemed to overcome her initial surprise at what she was looking at and carried on talking, saying it was nice to see him and asking, " What are you doing here?"

Andy was equally distracted. There was something different about his Gran, what was it? His Grandmother was looking fantastic. She had had her silvery grey hair cut short into a spiky 'pixie' cut that Andy found very beguiling. She wore a silky dress in a watery shade of blue that seemed to change colour as she moved. Simply cut with a vee neckline and cap sleeves it was difficult to know whether to describe it as a shift or a sheath dress -- in truth it was somewhere between the two. It was cut to follow the curves of her tall slender figure, not too tight but clearly clinging to her body, finishing at the tops of her calves. Andy noticed that there was a short slit at the back to about four inches above the knee. Her legs were bare but showed the tan that comes from a careful attitude to sunbathing -- golden rather than mahogany. She wore gold high heeled strappy sandals, probably a bit too high for someone of her age, but she walked effortlessly and elegantly in them.

"Gran -- you look amazing." He complimented her somewhat haltingly, and then with growing confidence. "I love your new hairstyle -- and your dress -- it shows your figure off to perfection."

She was not used to receiving such fulsome praise from a young hunk. Her eyes flickering back to his swollen cock, she realised that she was seeing Andy in a new light. He was tall, muscular in an undefined way and good looking with that collar length shock of blonde hair. And that cock! It was enormous! Or so it appeared to her. She was surprised to feel a sudden wetness between her legs as her pussy moistened in response to the thoughts that were starting to enter her head -- thoughts that a Grandmother should not have about her Grandson. Nevertheless she continued to allow the thoughts to run -- she never did have much willpower where sex was concerned.

"So do you like my new look? I thought it was about time I started to try and roll back the years. Although some things you can't do much about -- all these lines and wrinkles."

Andy had noticed the crowsfeet around her eyes and the laughter lines around her mouth -- they were not that pronounced, in fact Andy thought they were quite attractive, similarly so the stretch marks on the small area of her boobs that he could see. Andy hadn't really thought much about it before but now he realised that as far as he was concerned they were an added attraction -- they showed that this was a woman who had lived life and enjoyed it, her lines and wrinkles were the result of a lifetime's experience.

While Andy was mulling this over his Gran had continued talking, as much from nervousness as anything. " but I can at least update my style and my hairdo. Do you like it?"

Andy replied, with a rather dry throat, that he did.

This emboldened her and she blurted out "Do you think I'm sexy?" Whilst saying this she pulled the classic model pose -- hands on hips, a little wiggle then putting one leg in front of the other, her foot raised on the tip of her toe, such that her leg bent at the knee. Another little wiggle. one arm reached up to hold the back of her neck and she pushed out her tits, giggling as she dis so.

While shocked at his Gran's precociousness, Andy was feasting his eyes and brains on her. She did look good. "Yes, Gran you look fabulous -- very sexy -- any man would want you."

She smiled a little wickedly, focussed her eyes on his cock and ran her tongue around her rouged lips before making a licking motion. Andy shuddered at the thought of what those lips could do.

The fact that Andy was still looking at her with widened eyes and a slightly faraway look, encouraged her further. This had gone beyond a light-hearted game -- well beyond. "Would that be any man in particular?" she asked. Andy failed to reply, but his eyes said it all.

Emboldened by Andy's lack of discouragement, his Grandmother abandoned herself to the developing passion of the moment. She sashayed forward, wiggling her hips in an exaggerated fashion and lifting her heels up high -- just as runway models tend to do. She came face to face with Andy, put both hands on the nape of his neck and gently pulled him forward so that their lips touched. In that moment there was an inner spark of heat in both of them, and their lips mashed together in passion. Tongues extended and entwined. Seeing that Andy was as worked up as she was, she dropped one of her hands onto his crutch and started to gently massage his cock, while still pulling his head forward in a passionate embrace.

She deftly opened the press stud at the top of his zipper and then slowly pulled the zipper down, By sliding her hand inside his shorts, and sliding it around towards his buttocks, she eased the shorts over his hips and they fell to the floor, becoming entangling on top of his boots. This allowed her greater access to his cock and she massaged with more vigour. Andy started to breathe heavily as her ministrations caused his cock to swell, engorged with blood to the extent that Andy felt he would burst. Another quick flick around inside his pants by his Gran caused them to swiftly tumble down to join his. shorts.

Now his cock was fully exposed, the internal heat caused the air around his cock to feel cool, a delightful sensation. But that soon disappeared as Andy's Gran clasped her hand around his cock and began wanking him.

His Gran broke off the kiss long enough to whisper, "My you're a big boy, aren't you?" Indeed he was. His cock had now expanded to its full size, and the throbbing caused by his engorgement was an almost ecstatic pain.

Andy's hands were roving uncontrollably over Gran's body as if restless and not sure which was the most sensual place to stop. At first his hands were on her hips, partly to steady himself -- he was in such a state of ecstasy that he felt partly outside of this world and he was in danger of staggering and falling. His hands moved up to her waist, pulling her dress up with them as he slid upwards. Then one hand moved up to rest over her left tit, gently squeezing and massaging through the silk of her dress and her soft bra.

As his Gran continued to move her fingers up and down the length of his cock, pulling back the foreskin to expose his helmet, Andy began to moan involuntarily. " You like that don't you." his Gran asked, somewhat unnecessarily, as Andy obviously did.

Andy's answer was limited to a series of rising moans - "Aaahhh ....... ooohhh ........ uuuunnnggg," he breathed with deep sighs between. Gran took this as some sort of cue, or perhaps it inflamed her own desires. She slid down his body, pressing her tits against his torso as she went.

He felt her breath on his cock. It came in short gasps as though she was as excited as him. The pumping of his tool slowed to a gentle tidal motion. Her tongue ran up the underside of his shaft from near its base in a slow and deliberately teasing motion. It seemed to Andy to take forever to get to his helmet and he squirmed trying to get his Gran to move on quicker. She did, but in a slow sensual way, first flicking her tongue up and down the underside of his bulb and then, as Andy's torture mounted, her tongue slowly swirled around the full circumference of his head. This meant that her mouth was directly over the top of Andy's member and he felt the rasps of hot breath again. Andy raised up on tip toe trying to force the head of his cock into her mouth but she was wise to that and went back to gently 'nibbling' the underside of his cock with her lips,until he lowered himself again.

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