Anal Fascination

Mature guy teaches a 25-year-old woman how to enjoy anal foreplay.

Prologue.

This is set in the nineties before mobile phones and email when I was in my twenties and finding my way as a sexual woman. I made two major discoveries that are covered in the story; sex with an older man and anal.

There's quite a lot to cover so it's a multi-part story that I will publish every few days. I recommend that you read the parts in numerical order but that's not essential as each stands alone as a story.

Please enjoy and do let me know of any comments or observation both positive and negative.

Thanks

Jayne.

"Turn over Jayne," Bob said after they had laid down again, with him still soft and naked and her still in her jeans.

She turned onto her front, put her arms under her forehead and rested her head on them. She closed her eyes. Bob looked at her slim, lightly tanned back with the patch of freckles across her shoulders, her narrow waist, her boobs poking out from her sides where they were flattened on the bed and her white denim covered legs. Most of all he looked at her bum. It was like a ripe peach. The jeans were very tight and clung to her accentuating the symmetrical roundness of the twin orbs that merged together to form one mass of delicious anal fullness. He could hardly wait to see that naked and to indulge himself with its soft mounds and musky crease. But he would wait, he would leave that pleasure as something to anticipate. Patience, Bob thought, was an essential attribute for great lovemaking, particularly as one aged and the three or more performances in an evening were things of the past.

He lifted Jayne's hair away from the back of her neck. He kissed and licked that making her shiver with pleasure.

"Mmmm," she mewed.

Quickly realising how much she liked it, Bob continued to kiss and lick her neck as he slowly slid his fingers down her spine. She was so soft, smooth and lithe; her flesh felt gorgeous under his fingertips. He reached her waist and ran his fingers from her spine round to one hip then all the way round to the other. Softly, gently and caressingly he massaged her waist slipping his fingers slightly inside her jeans again.

"Nice?" he asked huskily."

"Mmmm lovely," Jayne muttered reaching down and placing her hand on Bob's bare leg just above his knee. Her touch felt wonderful and this time he didn't restrict her. She was pleased for she wanted to feel him, she felt that she needed to, in fact her mind and body were demanding that she did. She moved her hand upwards. Bob guessed that she wanted his cock, that she wanted to feel it and hold it and he wanted that too, but he knew she would be disappointed. And she was for as she closed her fingers round it, she realised he was only semi-hard. She had never experienced that before and wondered why, was it him or her?

"This ok?" Jayne asked stroking Bob's cock and rubbing his balls.

"Yes it is, it takes time now and then."

Now in totally uncharted waters she could only croak. "Oh."

"But don't worry, it gets there in its own time."

Bob knelt beside her and rubbed both of her cheeks at the same time. He squeezed them, kneaded them and pinched them. He ran his fingertips over them in decreasing circles and he pushed them together and pulled them apart.

"Has anyone told you young lady, that you have a gorgeous arse," he muttered feeling more stirrings down below.

"Mmmmm, yes it has been mentioned a couple of times," she replied loving the attention it was receiving and this, to her, completely new and different sort of lovemaking. "And I did win a rear of the year at college." As that thought hit her other ideas came into her mind. 'Fuck, it is lovemaking and not just fucking, does that mean anything?' she wondered

Bob moved behind Jayne straddling her legs just above her knees. That meant that she was unable to reach his cock, but instead was forced to focus completely on what he was doing to her, which was his intent.

With the lightest of fingertip touches, he started to massage her shoulders. Jayne loved it. It wasn't a massage, of course for it was far too soft and sensual for that, but that was exactly what he felt was apt for the occasion. Bob roamed all over her back and down the sides to slip along the flattened flesh of both of her breasts all the time moving downwards back to what had become a magnet for him -- her great arse.

Leaning forward sliding both hands into Jayne's armpits he trailed each of them down a little way until they enquiringly pressing against her breasts. He smiled and felt a surge of excitement as she lifted her body up allowing both of his hands to slip under her body and cup her pert breasts. They both enjoyed the moment; Jayne grunted and Bob started to harden again. He squeezed and caressed them and found her nipples that he pinched and pulled quite hard.

"Oh, oh," Jayne whimpered simply loving what he was doing.

Bob moved his hands back to her bum and squeezed and kneaded that for a while experimenting with how far Jayne might go by pressing quite hard right where the denim was covering her crease. She didn't demur or move or do anything that said to Bob that she wouldn't play. That made him feel good so he continued with the firmness of his anal, sexual massage.

He slid both hands round onto her hips, under her body and onto her soft stomach. He pressed and squeezed her there as he moved upwards back onto her waist. He found the brass button on the waist band and fumbled it undone. Using the softness of the bed to get his hand completely under her, he eased the zip down a little, not all the way for that wasn't necessary. He brought his hands back to her waist and held the waist band. He pulled it. It moved downwards onto the swell of her bum. The back of her white thong came into view as slowly Bob exposed those gorgeous round orbs of such sexual delight. He stroked them and Jayne sighed for it felt so lovely and different to the clumsy fumblings of her previous juvenile lovers. He wiggled the waist of the jeans over her cheeks and just a little way down her legs, just enough to expose her bum.

"Mmmmmm yes Jayne a really, truly gorgeous arse," he muttered trailing his fingernails all over it and down onto her upper legs still inside the denim and up onto her waist. He used his fingernails to lightly scratch it. He repeated all the movements he'd made when it was covered with her jeans. Without them, the sensations for both of them were magnified enormously.

Jayne was squirming with pleasure as surge after surge of such sexual excitement flowed from his fingers, over her bum, round her body into her breasts and down to her clit. It was such a new experience for her that she was getting wonderful and different sensations from the somewhat bizarre situation. To be lying on a married fifty-something-year-old man's bed still in her jeans and thong having had a massive orgasm was totally new to her. But then so was the lovemaking, sex or whatever they were doing.

What also was new was the amount of attention he was paying to her behind but more so was the pleasure, excitement and anticipation she was getting from what he was doing to her. Nobody had done anything like it before, nowhere near! A couple of guys had fingered her crease and kissed her cheeks and one had briefly tongued her there, but nobody had made love to it with the focused intensity, imagination and sheer eroticism that he was doing. And, she realised, she wanted more. She'd read about anal sex, rimming and buggery and the like and had been somewhat fascinated about it.

Bob leaned forward, slid a hand under her chest and cupped her breast. He had learned years ago that the stimulation of two or three erogenous zones at the same time more than doubles or trebles the excitement and pleasure for the other party; it provides synergy. As he cupped the flesh of her pert breast and pinched and pulled the nipple so she gained more than twice the delight. But when he added the third erogenous stimulation by running his fingertips from the base of her spine, through the crease between her cheeks, across her anal opening and onto the wet gusset covering her lips the pleasure simply multiplied so many times. He ran his fingertips back and forth along that wonderful valley, pausing and pressing enquiringly each time they passed her entrance.

Jayne didn't know what to do. She wasn't sure how to react. Nothing quite like this had happened to her before and she was well outside her area of familiarity. That was, for want of a better phrase, far more 'wham bang, thank you ma'am' albeit often several whams and bangs, but nevertheless severely lacking in the subtlety and sophisticated patience with which Bob was making love to her. She didn't know whether to moan with excitement, squirm with delight or push her bum back against the pleasure giving hand. What she did know for absolute certainty was that she wanted more of whatever Bob was prepared to give her. But she also knew that she would not be able to hold out much longer. Almost since she had lain on the bed and certainly since he had opened the button and slid the zip down on her jeans, she had felt the stirrings of yet another orgasm and whilst that was wonderful, it also made her feel embarrassed. Would he be thinking 'what a stupid little bitch' she pondered feeling terribly confused?

'Oh fuck,' she groaned to herself when she felt him rolling her thong down. The gusset momentarily sticking to her lips due to how wet he had made her. Thankfully, it then slipped from between her cheeks exposing that delicious crease and revealing the puckered entrance to her taboo place; 'or is it' she thought to herself remembering all the stimulation that he had been applying to that so intensely sensitive area? Is it a place that grown-ups play with she wondered her parents flashing into her mind with the vision of her dad bent over her mum's bum with his tongue between her cheeks.

Again, Bob only pulled it away sufficiently for him to do what he needed to do next. He rolled the waistband down so it was around her legs just beneath the flare of her bum. Taking hold of Jayne's legs just above her knees he eased them further apart, which caused the crease between her cheeks to open further, which in turn provided him with the room he needed.

'God what is he doing?' Jayne asked herself feeling slightly apprehensive, but enormously aroused as she was enjoying the subtle domination with which he was controlling her and the situation. Oddly, she was also getting a big kick from the situation he was creating. It was the sordid and wanton nature of it that was turning her onto levels that she rarely reached during foreplay and never had with Jack. In his marital bed, him naked, her with her knickers and jeans around her thighs about to cum from merely being touched! But she knew, deeper down, that it was not the touching and other things by themselves that were having this intense effect on her. Guiltily she acknowledged that the main influence was that Bob was focusing his attention on her bottom and in her mind that was somewhat taboo.

Bob stared intently into the gorgeous blonde's bum crease. It wasn't a thing of beauty, after all how can a dark ring of puckered skin round a small hole be that? Men don't lust after it because of its appearance as they do, for instance a pair of tits or the roundness of a bum. No, it was something else; the taboo nature, the mystery, the curiosity, the beautiful shape of what surrounds it, the feel of that passage around a finger or the desire to fuck it, were the appeals.

He ran his fingertips through the crease again and once more paused right on the hole. He pushed and Jayne grunted. Again, though she did nothing to object. His heart pounding with excitement and nervousness, Bob bent his head; he kissed each cheek and then the base of her spine. He licked that and then slid his tongue slowly downwards across the narrow patch of skin separating her spine from the start of her crease. Then it went into the crease. It was no distance from the start of her crack to his destination and within seconds Bob's tongue was pressing against Jayne's arsehole.

This was another first for Jayne. But then it would be a first for many women. After all bum licking is not that popular or acceptable a pastime, well not in the UK. Popular it may not yet be, but it is amazingly stimulating for man or woman. She could feel that Bob was holding her cheeks apart and that the tip of his tongue was probing at her hole. It was opening it up a little and sliding slightly inside that tight passage. And that felt fantastic.

None of this was planned by Bob. He wasn't like that. When having sex, he was very much a sixties guy; 'go with the flow' and do what feels right and if it feels right then it probably is right, being his mantra. Whilst obviously not fool proof, that philosophy had served him well not only with Phillipa who was now quite an anal fan albeit only occasionally, but also with his numerous short flings, one-night stands and longer-term affairs. He very much felt the flow with Jayne was between the cheeks of her lovely, youthfully, pert bottom than between her legs although, of course that area would not be ignored.

"Oh Bob," she sighed, feeling fully deliciously aroused and almost delirious with the need for sexual gratification and satisfaction.

"You ok with this?" Bob asked, his erection now gaining full strength.

Jayne grunted. "Yes."

She was amazed. Both at Bob who, although she fancied him, she had thought might be rather unadventurous and at herself. That she was lying face down on his and his wife's bed, naked above the waist and now with her jeans and panties pulled down almost to her knees was crazy enough. But that this middle-aged, at least, man was now starting to lick her bumhole and push the tip of his tongue into it and that she was allowing him to do that was simply beyond belief. Beyond the belief she had before she met Bob, but now very much within it, for he was doing it and she was loving it. She wanted more. But she felt restricted. The jeans and panties around her thighs were restraining, she didn't like that and now he had uncovered her most intimate places why keep them on she was thinking? He's seen everything so why should I be wearing anything? He isn't. On top of that Jayne had this adventurous, sort of slight exhibitionist streak in her, the one that had prompted her to do some glamour photographic modelling. That streak was telling her to reveal all to him, to expose everything she had to her mature lover, for that is what he now was. It was telling her to flaunt her body at him and she wanted to do that. She reached behind and tried to push the jeans and thong further down, but she couldn't. At first Bob had thought she was trying to stop him, but he quickly realised what she wanted to do.

Anticipating her need he whispered. "Hold on Jay," taking hold of the material. He moved away a little, closed her legs and slowly eased her clothes off until she was naked. She looked fantastic and he went to turn her over and ogle her front view, but he didn't, that could wait. "Ok now?"

"Mmmm that's a better, I felt odd like that."

"You looked fantastic though."

"What with my jeans and panties round my thighs?"

"Yes, it was enormously wanton, you looked like my slut."

At first that annoyed Jayne a little, but when he added. "My adorable, sexy slut lover," she realised it was an adult type of dirty talk. It appealed to her.

"And is that what you want me for Mister Roberts to be your slut lover?"

"Yes, Miss Canton it most certainly is, will you be that?" he asked rather roughly grabbing her ankles and pulling her legs apart.

Finding the phrase quite a turn on she grunted. "Yes." realising that now he would be able to see her soaked, blood engorged lips between the top of her legs as well as the hole he had just been tonguing. That excited her more as did Bob asking.

"Well tell me what you'll be Jayne?" as he knelt between her legs, just by her knees.

"I'll be your slut lover Mister Roberts," she replied as she felt his hands slip under her hips and start to pull her.

"And what do you want me to do now Jayne?"

"Oh Bob," she groaned as he lifted her hips up from the bed until her stomach was ten inches or so above it, with her face buried in the bedclothes. He wrapped his arms round the outside of both legs with his hands slid between her legs from the front. He wiggled forward so his face was close to her gorgeous arse.

"Tell me Jayne, tell Bob what you want him to do?" he asked as he licked each cheek and pressed his fingers against her pussy.

"I don't know," she answered honestly.

She didn't know for a number of reasons. She wasn't quite sure why he was asking, how broadly he meant the question and how detailed he wanted her to be. Also, she didn't know for sure what she wanted for she wanted anything and everything this amazing older guy could give her. And as she lay on his bed, her face pressed into the high-quality bedclothes that she suddenly realised would have to be washed before Phillipa's return, with her bum in the air, her legs wide open and his arms round her legs so his fingers could reach her clit and pussy as he stared at her anal passage, she suspected that what he could and would give her would be very special indeed.

With such a sight just in front of his eyes and the prospect of him tonguing her again, Bob's mind went off dirty talk. 'Why talk it when you can do it' he thought to himself pressing the tip of his tongue against Jayne's hole.

"Jesus, oh fuck," she groaned quite loudly as she gripped the bedclothes tightly and pushed her body back against him as a strong surge of arousal shot from her bottom and throughout her body. Bob licked and probed with his tongue on Jayne's bum hole and then at the same time brought his fingers on both hands into play. He found her clit and rubbed that with one finger making her almost purr with pleasure. He slid the fingers on the other hand around her slimily, but deliciously wet and engorged lips letting two slip inside her.

Jayne would not have believed that such sexual stimulation was possible. Nothing she had experienced so far had come anywhere near to what this 'maestro' as she suddenly thought of him, 'a maestro playing me like a violin,' she momentarily thought as the sensations from her clit, her lips, the inside of her cunt and her arse all combined. She knew she was grunting, groaning and moaning, sighing deeply and maybe nearly screaming, but she couldn't help it so intense were the pleasures he was giving her.

But Bob wanted more. He wasn't quite sure just what yet for he had no idea how far his young, blonde lover would go with him or, let him go with her, but he suspected quite some way. One thing he didn't want just yet, he thought as he forced his tongue into Jayne's gloriously tight hole wondering whether it had ever been penetrated by finger or cock, is to her fuck her. He knew that if he did his desire would disappear and his ability to recover would deteriorate significantly.

Still fingering and licking her he sat down with his legs to the side. Slowly he turned them, laid against the pile of useless cushions his daft wife left on the bed and slid his legs inside and through Jayne's opened legs. At the same time, he pulled on them moving her body up his so that the back of her legs beneath the knees slid under his arms and those just above her knees pressed against his armpits.

Jayne didn't work out what was happening when Bob first moved as she wasn't thinking very straight. But then, when a girl is having her clit rubbed very expertly, she has two, three or maybe even four fingers up her cunt and her lover has got his tongue up her arse, how can she be expected to think clearly!