Anal Fascination Pt 01

The difference between a young buck and an experienced lover

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.

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

Thanks

Jayne.

Pre anal.

It was the third time they had fucked that afternoon and evening. After a long session in the pub with their mates, they had gone to his rather grubby bedsit in Bethnal Green in East London. In the pub he'd drunk pints of beer and she'd drank vodka with a touch of water, something she'd heard that Ginger Spice drank. They were both pleasantly pissed and but for that it was unlikely she would have accepted his invitation to 'come back to my place for some pasta and a fuck.' It was also unlikely he would have asked her if he hadn't been half drunk. They lived in the same block of flats and that was how they had met and became friends, but until today, not lovers.

Jayne was the tastiest bird in the group of twelve that met most Wednesday evenings and Sunday lunchtimes in The Crown pub in Bethnal Green Road. It was an old-fashioned pub that sold good beer and lousy food, had no canned music or one arm bandits, but had a darts board and a pool table. It suited their crowd down to the ground. Urban rumour had it that it was a favourite of the Kray Twins back in the sixties, but then everywhere around the East End of London has such rumours.

Jack was just an ordinary bloke. Averagely good looking with a reasonably vibrant personality, he was well liked, got on ok with nearly everyone and pulled his fair share of birds. Alright, it may be that the ones he got tended to be fat or plain, or both, and were rarely of the class of Jayne, but he was a pretty good fuck. He had bags of stamina and his recovery powers were awesome, often being ready again almost before he pulled out of the girl, which more than compensated for his lack of finesse and patience. This had become almost folk lore amongst the small group. Although generally they didn't fuck each other, but then mates don't do they, some of the girls knew other girls who had been 'sorted out' by Jack, they passed it on and thus, he was held in some esteem by the group?

"You really up for a fuck?" he asked as they wandered arms around each along Roman Road towards their homes. Jayne alternated between the small flat in Roman Road and living with her mum at a palatial pile in Chigwell, Essex, some eight or so miles away.

This wasn't a normal sort of exchange between them and never had they gone so far. However, in their near drunk states it seemed perfectly reasonable for him to ask that and for her to giggle that she was.

Jack pulled the long, blonde-haired, blue-eyed beauty into a narrow alleyway. He pushed her up against a wall and kissed her, almost knocking her glasses off in the process.

"You sure?" He asked cupping one of her C cup boobs. He couldn't really believe his luck.

"Totally," she replied letting her hand fall down between them so it brushed across his erection.

Although Jayne had been with a few pretty virile, young guys with whom she'd fucked several times in an afternoon, evening or night, that hadn't happened recently and currently she didn't have a boyfriend. Apart from being a little tipsy, which was why she accepted Jack's original invitation to 'pasta and a fuck,' they were fully paid-up members of the mid-nineties, 'now' generation and they could do anything!

He kissed her, hard and lip squirmingly, shoving his tongue deep into her mouth and pressing his hard-on right into her belly. She pushed back with her pubic mound and took the tip of his tongue between her teeth and sucked on it. Reaching down, Jack grabbed the hem of her white tee shirt that she was wearing outside her tight, blue, ripped jeans. He pulled that and the covering dark blue, vee necked, cashmere, sweater up baring her tits. As he and most of the group knew she was a follower of nineties fashion and often didn't bother with a bra. She didn't really need the support for her C cup tits were still youthfully pert but, of course, they jiggled and wobbled deliciously when she moved!

"How about doing it right here."

"Fuck off I need a bed."

He laughed. "Come on then let's find one."

The first fuck was quick, urgent, quite dirty and very satisfying for both of them, but it wasn't in or even on a bed. It was with Jayne bent over and Jack fucking her from behind.

Once inside his 'studio apartment,' he grabbed her, they kissed and quickly were pulling each other's tops off. He had a hairy chest that Jayne loved and she had full breasts capped by prominent, deliciously pink, nipples that sent men in general and him in particular fucking crazy. Once he had her top off and her tits were bare, he turned her and positioned in front of a floor to ceiling loft mirror. With both of them following the action in the mirror, Jack squeezed and cupped Jayne's tits and pinched and pulled on her nipples. Slowly he moved his hands downwards, fiddling his fingers just inside the waistband of her jeans before cupping and rubbing her mound. She watched fascinated as he slid her zip down and got his hand inside. That made her grab her own tits exciting both of them.

So far it had all been slow and smooth, measured and calm, but almost immediately he found and pressed her clit they both seemed to explode. Her jeans came down, his hands plunged into her panties, he pushed his jeans down and pressed his hard, fully erect, youthful cock against her arse. Pushing her forward and making her bend at the waist to support herself with her hands on the mirror they both watched fascinated as he pulled her thong down so it was tight around her thighs, six inches or so beneath her pussy. She was relieved to see him take a condom from his jeans that were rumpled round his ankles and put it on.

Holding his cock in one hand and her hip in the other he slid his condom covered cock into the crease between her pert cheeks with its length pressing firmly against her bottom. Moving his hips a little caused the end of it to press right against her hole making her think for a moment or two that he wanted to go up there. Jayne had not really experienced full anal although once a tongue had strayed there and a couple of times a finger had pressed against it. But so far it had been cock free.

But he refocused his angle and pressed his cock right on her lips and without further ado plunged through them and surged right into her cunt.

It didn't take long before she was writhing against his cock and he was ready to shoot his load into the condom. That they were able to create a mutual orgasm was more due to the wantonness of the situation than anything else, but they ended up with her face down on the carpet, her bum in the air with his cock buried deep in her.

It hadn't been much longer before they were both completely naked lying on the bed. Jack was between Jayne's legs, which were drawn up, wide open and wrapped round his waist. He was slamming himself into her loving both the depth of his penetration and the feel of her legs around him.

The third time, a couple of hours later after they'd had a cup of tea, the promised pasta and a couple of large vodkas each, wasn't a fuck. It was her wanking him as he sucked her tits and finger fucked her.

They did it once more when they woke up in the middle of the night. This time they were on their sides and he fucked her from behind squeezing and pinching her tits and rubbing her clit.

Shrugging into her jeans, tee shirt and sweater, but not bothering with her thong, around three in the morning, Jayne went to the door leaving Jack in bed.

"I guess I'll see you Wednesday at the pub," she said as she slipped out of the door.

*

"Jayne, it's Jayne Cannock isn't it?"

It was the following Wednesday. Jayne was at home with her mum in Essex. She spent about half her time at the small flat in Bethnal Green rather slumming it compared to the near mansion her mum had got as part of her recent divorce settlement, where she spent the other half of her time.

She was in her local gym when she'd heard a man's voice call out her name. Turning she saw a guy in a suit staring at her. She didn't recognise him until he moved closer and said.

"Hi Jayne, you were my daughter's friend, Emma, Emma Roberts."

"Oh yes," she replied recognising him as the father of a girl she had been friendly with up until they were both seventeen or so or so. "Mister Roberts, how are you?"

"I'm fine Jayne and you?" he asked shaking her hand.

"Great thanks, how's Emma?"

"She lives in New York now, she's fine."

"Oh yes, that's right I heard that from her Facebook."

"And your parents Jayne, how are they?"

"Well unfortunately there's been lots of problems there Mister Roberts."

"Bob please. Mister makes me feel even older than I am."

Jayne laughed. "Bob then."

"Oh dear, I'm sorry."

"It happens I guess; they are getting divorced, dad lives in Spain."

"Is your mum still in Chigwell?" he asked recalling Jayne's mother who he and his wife had got to know through school functions. As most men did, he particularly remembered her splendid pair of tits and quite fancying her.

"Yes, I live with her most of the time, but also have a little flat in Bethnal Green, where I stay during the week, it's easier for work."

"That sounds a good arrangement."

"It works for me and mum, we love each other of course but two women need their own space. Anyway, what are you doing here at a gym in a suit?"

"I work for the group that owns the gyms and have to visit them from time to time, but not much longer."

"Why?"

"Well I retire in a couple of months' time, that's early retirement I might add," he smiled.

"So what do you do Mister er Bob" she smiled.

"I'm a Regional Director."

"Wow, big time tycoon," Jayne said smiling and recalling that when she was friendly with Emma he was always travelling.

"Not really, just a small cog in a very big machine. I manage the gyms in London and the South East and I'm setting up the regional headquarters here as my last job really before I work on my golf handicap," he grinned.

"Well good luck with that, mum still plays."

"Yes I recall she was pretty good."

Smiling, Jayne quipped back. "At what was that Bob?" remembering thinking back then that they fancied each other.

"Now, now Jayne. Look, how about popping into my office and having a coffee or a glass of wine so we can catch up," Bob asked not really thinking of the consequences or what his PA would think.

"Sure when, now or after my work out?"

"Up to you."

"Well let's do it after I've worked out a bit, I doubt I would be up to a work out after a coffee or a glass of wine."

"Great, just come through that door up the stairs and I am the second door on the left."

Bob went to his office and slumped into his big, black leather chair. His mind went back to the days when Emma and Jayne would come to his house. Even at fourteen or so she'd been ravishingly pretty in a blonde-haired, blue-eyed way whilst his daughter Emma with her dark hair, green eyes and voluptuous figure had been sultrily attractive.

He hadn't seen Jayne for several years, but had bumped into her and her mother in Waitrose a few months ago. He couldn't understand why, but he fancied the young blonde immediately. He didn't often lust for younger women although he saw plenty at the gyms and in all truthfulness, he would have thought he would fancy the mother with her fuller figure and gorgeous big, tits more than Jayne. But that wasn't the case, well it was sort of as he rated his chances of scoring with her higher than with Jayne, but seeing the daughter in her skin tight jeans with her pert bot so clearly outlined did something to him.

Those thoughts, or so he had believed, were well behind him as were any ideas of anything happening with Jayne. But seeing her now in her tight, black gym gear had rekindled them. Her white singlet under the tracky top with a black sports bra moulded to her breasts, her lycra, mid-calf-length, cropped pants clinging to her bum and thighs very tightly accentuated the roundness of her pubic mound and the symmetrical pertness of her gorgeous arse, had brought the lecherous, wanton thoughts that had occupied his mind all those years ago bubbling to the surface.

He had always thought of himself as a tits man, and being truthful it was her breasts that had made him fall for Phillipa in the first place. But as he had got older and especially since taking the job at the gym company, he had found his eyes more frequently straying toward girls' bums than their boobs. That had coincided with him asking the masseuses and hookers he visited fairly regularly for anal and paying the hefty surcharges they demanded for selling their bums. Luckily for him Phillipa had, a few years ago, surprisingly, taken to letting him into fucking hers.

He sat behind his desk pleased that Pauline, his PA, was at a meeting at the gym in Chelmsford for he had an absolute raging hard on. And at fifty-five such things didn't happen that often without some significant stimulation and young Jayne Cannock and her gorgeous bum was certainly providing that.

Bob was at a crossroads in many ways. Obviously, his impending early retirement was the main one, but also the state of his marriage was up there in the levels of significance and importance. Things were not good between him and Phillipa, his wife!

Jayne worked out with a range of stretching exercises, then ran for twenty minutes and finished on the rowing machine or a bike. As she did, her mind went back to her schooldays and to Emma and her family. She and Em had been close friends and they'd had good times together. Bob hadn't been around a lot when she was at the house but had sometimes given them a lift somewhere and a few times her alone a ride home. He had never said or done anything at all out of line. That wasn't because he hadn't had thoughts for like most middle age men he did, he had lurid ones, it was because like most men he was scared of being rejected and frightened of the repercussions. He and Phillipa had still been sort of in love at the time and the family, Emma and two brothers had been close knit. Things had changed when Emma had moved to the US with her derivative trader position with a Swiss bank and the two boys had left home. Although they were still very close Phil's sexual appetite and her interest in sex had declined in the past few years being replaced, or so it seemed to Bob, by golf. He often wondered if there was more to her close friendship with her 'golfing girls' than simply the sport and tried fathoming out how her enjoyment of anal play fitted in with this 'new' her.

But unlike her, Bob was unable to go without full and varied sex. Like many fifty-something middle-aged-guys he had started looking elsewhere and now visited both massage parlours and hookers, though he far preferred the former as there was a degree of romance about being massaged before fucking the masseuse. He still had a strong sex drive and appetite and almost permanently felt frustrated and up for it. He knew that if the right opportunity came along, he would take it and an affair was more of an inevitability than a possibility.

'Oh my fucking lord,' he said to himself as he walked through the gym, ostensibly on an inspection tour, something he did several times a day. In reality that was only part of the reason. The other reason generally was to check out the talent and the specific reason today was to check out Jayne who he had just seen on a cross trainer. He stood off to one side against a wall out of her sight line and simply ogled the great sight.

As most girls did, she had put her hair up into a pony tail. As she power walked and ran, that was flying around bouncing off each shoulder and occasionally snaking round her neck and dropping down to rub one or another of her tits. Sometimes it snuggled between them, making Bob imagine it was his cock. Her boobs were bouncing up and down with each stride she took, the soft flesh jiggling and wobbling most wonderfully inside the black bra and white top. She was wearing the singlet, which was like an athlete's vest, outside her lycra pants. As she ran the singlet kept riding up giving him wonderful flashes of her tanned skin just above her waist. It was her arse though, that was the main feature. With the black lycra moulding itself to and between her twin, rounded orbs like a second skin and with those swaying and rolling around, it was a sight that really should have been censored, he thought smiling to himself.

And then he felt as if he was punched in his groin when he realised he couldn't see a VPL. 'Fuck, a pound to a penny she's naked under that' he thought as his cock started to harden again. Wow twice in half and hour he realised joking to himself 'I'm becoming a stud,'

It was then that Jayne for no reason glanced over her shoulder and saw him. Bob quickly turned and made out he was examining a piece of equipment, but Jayne knew, as women always do, that the only piece of equipment he was examining was her arse. Why the hell that made her emphasise the rolling, swaying undulations of her, slightly fuller than she liked, yet still, pert butt she didn't know, but she did.

After seeing Bob leching her, Jayne's mind, for some unfathomable reason, turned to the coming evening when she would be going to Bethnal Green to the pub and would see Jack. They hadn't spoken since Sunday and she wondered how things would be between them. They certainly weren't in love or anything like that, but they really had got it on big time on Sunday and, she had to admit it was bloody good but lacking in something, finesse, subtlety, technique, she wasn't quite sure what. She had no more idea what he wanted from the 'relationship' than she did. Perhaps we'll just become fuckbuddies she smiled thinking it would be quite nice to get some regular sex. Like many single young women Jayne got far less sex than many would imagine and often it was the wrong kind. Rarely was there any real affection or romance involved and most was animalistic in approach and unsatisfactory in fulfilment.

Then for some daft reason she found herself trying to recall how many times he had made her cum on Sunday. She always found running on a training machine hellishly boring and she needed something to occupy her mind and remembering orgasms certainly did that.

She remembered that the first time they fucked she was still partially dressed. They hadn't messed around much before he was in her from behind so she only had one climax, but it was a big one. That, she thought as she ran on the boring machine, was likely to be due to the attention Jack, probably unwittingly paid to her bum. The next time when they were naked on the bed, he'd made her cum very quickly after entering her and then again when he exploded. Later in the evening after they had eaten, sobered up and then got half pissed again on vodka, they had started kissing and he undid the tie on the dressing gown he'd lent her. He opened it and started caressing and then kissing her tits. Jayne found his cock under the towel he'd wrapped around his slim frame. He was reassuringly hard and she pulled the towel away, but they left his tee shirt on. As she stroked him so Jack licked and sucked her nipples and found her clit with his fingers. Rubbing that sent such powerfully, sexy feelings through her that it made her cum. They stopped for a while as they sipped their vodkas and then rolled together on the floor squirming their bodies together. Jack rubbed Jayne's clit again and then shoved two or three fingers up her and started to use them as a surrogate cock by finger fucking her. She responded by rubbing his cock harder and faster. She remembered him muttering.