More anal with the masseuse and going further with Jayne.
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. 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.
Getting to know each other.
Jayne and Bob 'bumped' into each other several times over the next few weeks. That wasn't a coincidence for Bob had checked the records that showed when a member checked in and out of the club and he saw that she tended to visit on Saturday mornings and Monday and Wednesday late afternoons. He made sure he was there particularly on the Wednesdays when he gave her lift to the station.
He knew that she was becoming an obsession and knew that he would have to take care not to make a total fool of himself. That said he felt so strongly that he didn't feel that he could just let it go. There was always that outside chance, that one in a million bet that somehow, she would agree. But agree to what? In his mind Bob would have been happy if she just agreed to spend more time with him, maybe the occasional dinner or letting him see her body, hold her, ogle it and touch and stroke it. In his fantasy ramblings, there didn't have to be full sex, he'd had plenty of that over the years and just a few fucks with her didn't seem that necessary. Being with her and seeing and feeling her young body did though!
Jayne didn't work out that he planned their 'bumping' into each other, why would she? After all he worked for the group so why wouldn't he be there? It didn't bother or even intrigue her that much, but the lifts to the station did. They were alone then, completely alone and usually in the dark. They would sit outside the station until they heard the train coming and then both would get out, she'd kiss him on the cheek, then run into the station.
They talked a lot in the car. About her parents break up, him and his wife Phillipa and daughter Emma and a few other mutual acquaintances. They chatted about his and her jobs and her studying at college, she didn't mention her part time work of glamour photographic modelling. He told about his pending retirement and how he had no idea how he was going to fill his time.
"Why don't you and Phillipa travel more, go and see Emma and travel round America."
"It's not that easy."
"It is, just book the tickets and go."
"Phil has lots of other interests, golf, tennis, some lady's clubs that sort of thing."
"I'm sure she'd be pleased if you whisked her off her feet."
"No, she wouldn't Jayne, things aren't too good between us."
He didn't expand on that and Jayne didn't want to pry so they left it with her assuming, correctly, that his marriage wasn't too good.
Jayne was surprised how easy it was to chat to a man some thirty odd years older than her. But then she shouldn't have been really for with many of her clients there was a similar age gap. They, though, paid for her to undress as they took photos of her, Bob was just a friend. 'Fuck I have a friend who's nearly mid-fifties' she mused to herself knowing deep down that he wasn't really a friend, more a suitor.
Bob was as amazed as he was pleased and excited at the time he spent with her. As it happens so was Sofi, for each Wednesday after dropping Jayne at the station he went to see her and most Wednesdays he fucked her. Sometimes, though, she sucked him to conclusion, now not using a rubber, but understandably not letting him cum in her mouth; it was almost as good for Bob though to do it onto her full tits. She also now let him kiss her and that was also nearly as good as a fuck. He often wondered what it was he was after with Sofi, for it certainly wasn't just the sex; affection, intimacy, just being with woman maybe? He now booked double time sessions, two hours, with her!
Although he now saw her often, roughly every couple weeks or so, they hadn't got round to full anal sex. This was mainly her doing as she found it quite uncomfortable. So, when their action moved towards her bottom she promoted something else, such as a blow job or her rimming him which Bob found almost as satisfying.
The usual menu of services that she provided were some long, lingering kisses as he fondled her body, both of them undressing well more him undressing her as he would be clad in just a towel when she came into the massage room. She would then fulfil her duty with a soft, slow and sexy massage. Recently, they had then taken to him giving her a reverse massage that included clit stimulation, fingering her and then oral during which she would cum, although at times he felt that might be rather exaggerated.
The night he told Jayne that things were not good between him and Phil, things with Sofi went slightly differently. As she lay naked on her front, he let some oil seep into the unusually deep, in his experience, cleavage between her bum cheeks and then slid his finger along it. Naturally pausing when it pressed on her hole he was surprised, but very pleased when she grunted and her body lifted up from the bed a little. He pressed harder, she almost growled and her legs opened slightly more. Bob went for it and pushed so his finger up to about the cuticle went into the puckered, almost brown skin surrounding her anus. She pushed back and let out a deep sigh. He gripped her hand and squeezed.
"Ok Sofi?"
Squeezing back she murmured. "Mmmm, yes but be gentle."
Bob would never be anything other than that and was indeed very gentle as he edged his finger further and further up her arse until it was well past the second knuckle. Leaning forward and kissing her he asked if she was sure and she whispered that she was as she reached back and gripped his cock that she started to masturbate. Actually, as the pumping movements necessary for her to wank him were difficult she held her hand still to provide a surrogate cunt that he fucked. And then, being well lubricated with the oil he finger-fucked her arse until she came and he shot his lot all over her waist and hips.
On Wednesdays he was also contriving to meet Jayne and give her a lift to the station. The chats and times in the car, though exciting due to the, probably forlorn, potential made him feel rather foolish and he often thought 'no fool like an old fool.' On the other hand, they excited and aroused him. Just seeing her did that and being with her when they occasionally chatted in the gym and always when she was in his car did it even more. There were numerous times when they sat there with him sporting a full erection.
Now, not only was he contriving to give her the lift, even cancelling meetings so he was at that gym rather than any of the other ten on his patch early Wednesday evenings, but whenever she was in the gym he found reasons to wander through and take surreptitious peeps at her gorgeous bottom and pert tits swaying and bouncing on the running machine or the cross trainer. Even her friendliness was attractive and exciting and he was beginning to feel she was becoming a little flirty, or was he kidding himself? 'Was she feeling something?' he continually asked himself, torn between the absolute fascination he had for her and the natural reservations of a man of his age about a girl of hers. He wanted to make a move, try it on, ask her to go out with him, well more to the point to go to bed with him. He desperately wanted to fuck her as he fucked the masseuse each Wednesday making out the body under his or the one bent over as he took her doggy style from behind or, latterly whose arse he was now finger fucking, was Jayne. But his concern at being rejected or, worse laughed at by the girl who he sometimes thought may have no idea of his fantasies, were stronger. Not only would the embarrassment he would feel if she told him to fuck off and not be a dirty old man be terrible, the concern that she would tell his daughter who in turn would pass it onto Phillipa, was just too much to contemplate. So, he did nothing, well nothing overt, but it didn't stop him thinking and wishing and using the masseuse whore as a Jayne substitute!
Jayne and Jack were now constant lovers, well fuckbuddies. Each Wednesday and most Sundays they would fuck. Yes, fuck not make love for with neither of them was there any pretence that they were anything more than fuckbuddies, no more and no less. And it was good. Jack was still rather poor at foreplay and didn't seem to have any interest in oral, but boy could he fuck. He was sometimes as hard as rock for a couple of hours fucking Jayne to orgasm two or three times before he came. And even after that he was ready again very quickly and during a late Wednesday evening and night or a Sunday afternoon and evening, he would usually fuck her three or four times.
Jayne had never 'been serviced' like this. She'd had a few longer-term boyfriends and a couple of them had similar, but not as powerful recovery powers as Jack. She had never regularly been fucked six or seven time a week and, although she was often a little sore, she was enjoying it, although she was disappointed at Jack's lack of subtlety and his seeming aversion to oral as she loved both giving and receiving that. But whenever she tried, he managed to change it so they did something else.
Despite her having absolutely no reason for feeling frustrated she sometimes did. Not for wanting more sex, that may well have been impossible, but for wanting different sex. A gentler, relaxed and languid sex that might include soft massages, maybe candles, bathing together and revelling in the joy of having a man's head between her wide-open thighs. And she was happily more than prepared to return the pleasure by having a man's cock buried deep in her mouth. In some ways worryingly to her, but in others very arousing for her when she imagined holding a dick and wrapping her lips round it, it was Bob's body that was on the end of the cock and not Jack's.
She was totally confused with herself and her attitude. Sexually more satisfied than she had ever been in her active life, with a young virile lover, she had persistent thoughts of being naked and having sex of some form or other with a man older than her father.
*
"Bloody rain, why not sit in here until the train arrives?" Bob said a couple of weeks later.
"Good idea and don't you get out and get wet," Jayne replied.
"And what, miss my kiss?"
"I am capable of kissing in a car," she smiled, leaning across and pecking him on the cheek, her top gaping he noted and she realised!
Over the past few weeks, also without discussion, they started leaving a little earlier meaning that they could talk more and they covered a wide range of topics. This surprised her as much as it thrilled him for chatting to 'old guys' was not really Jayne's thing. She even started to let a couple of trains go by claiming 'it's early.' Then she would peck him on the cheek and get out with his eyes taking in every wiggle and wobble of her pert bum as she ran the few yards into the station.
Tonight was no exception. Recently, he had taken to parking just past the station in a side road. That was darker than the main road and didn't have double yellow lines. They had let several trains go by when they heard the rumble of another.
"Ah well I'd better go," she said turning and looking at Bob. He also turned and leaned across the centre console stretching his left arm along the back of seat, his hand falling onto her shoulder. She was wearing a long sleeved, tee and a sleeveless cardigan that was unbuttoned. It was very evident to him that she had not bothered with a bra and that had given him crutch tingles since she'd got into the car especially when he wondered if her underwear omissions also included panties. The tingles were not just due to the sight of her unfettered breasts under the thin tee, but also the message he speculated and hoped that they were sending to him. In his middle aged, frustrated yet hopeful mind it was a signal of availability that she was transmitting.
Jayne also leaned forward. Their faces were close and he was about to brush his lips against her cheek when something came over him. The combination of her lack of bra and closeness was too much of a heady cocktail for the older man to handle. Burying his hand in her golden locks he pulled her face towards him and kissed her full on the lips.
Jayne's first reaction was to pull back and she did a little, but not completely to break the kiss. His lips felt good on hers and his tongue rubbing against her upper lip sent shivers through her. It was Bob that broke it.
