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.