Anal Fascination Pt. 03

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Mature guy teaches a 25-year-old how to enjoy anal foreplay.
5.7k words
4.48
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Part 3 of the 5 part series

Updated 06/11/2023
Created 01/21/2022
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Young woman finds sex with an older man and anal.

Prologue.

his 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.

Car sex.

On the back seat of his car, Bob was tense with hope and anticipation. He so badly wanted to feel Jayne's tits, but then he badly wanted to feel any part of her. But was she up for it, was their relationship strong enough yet he wondered suddenly realising that his fingers were slightly further up inside her top? Somehow, without him being fully aware of doing it, his hand was on her side just inches down from her breast, so near, but yet so far, he grinned. Still though, he acknowledged, she wasn't stopping him or pushing his hand away. There was no resistance to him touching her bare flesh several inches now above her waist. Incredibly really at that miniscule point in time, there was nothing more important to either of them than how far Bob's hand and fingers went up Jayne's top.

Bob stopped kissing her and lifted his head up. He looked at her and Jayne turned and lifted her head so their eyes met in the dim light. Deep down, they both knew what was going to happen for they both knew what they wanted to happen and they both knew what was inevitable. Bob's hand slid slowly up her chest until it was just inches from her breast. He stopped with his eyes boring onto hers silently asking the question, enquiring, essentially saying. 'May I touch your tits?'

This was new territory for the blonde. In her 'normal' mid-twenties world, boys didn't ask, they didn't consider the girl's feelings, they took rather than shared. But she liked Bob's approach, she liked being asked, she liked it being mutual, she liked her wishes being respected. So, she gave him his answer by almost doing nothing. By not resisting, by not objecting and by not moving, Jayne accepted Bob's invitation. By simply lying there she in effect gave him her permission, her agreement, her authority to touch her tits. He recognised that and his heart started to pound. Although momentarily thinking 'Shit I'm only going to feel her up' it was still one of the most sexually charged and erotically exciting moments he could recall.

And then with no further delay and their gazes locked, Bob slid his hand up Jayne's body and closed his fingers round her breast, squeezing and squashing the shapely orb. It was incredible for both of them and exactly what they each needed and wanted, but of course they didn't and couldn't say that to each other. Instead, she sighed and he let a low appreciative groan.

The first time that a potential lover touches a woman's breast is always very special. And this was no exception. Even though Jayne had been aware that it was going to happen, that she was expecting it and that she wanted it, the feel of Bob's hand on her left breast sent a surge of desire and want through her. It also made her body jerk. She kissed him harder as if saying 'Yes. That's ok, it's what I want too."

Bob squeezed her beautifully pert breast and pinched her rubbery nipple at the same time. It felt amazing to both of them. To her, oddly, it was so much more erotic than when Jack did it and to him, Ok Sofi had bigger tits, but he paid to play with those; the one in his hand was being given freely to him by a young, gorgeous girl who was well young enough to be his daughter.

"Oh Jayne," he breathed.

"Shush don't say anything," she whispered back putting her fingers to his lips. He opened his mouth and took her middle finger between his lips. He sucked it gently as he continued caressing her tit.

They were like that for some time. Most of the buttons on Bob's white cotton shirt were undone and Jayne's other hand was softly stroking his chest. Her finger had now been drawn into Bob's mouth, 'just like a cock in mine' she couldn't help thinking, but then that is the idea of finger sucking, she smiled. Their mouths were squirming against each other and his hand was up her top, stroking, squeezing, pinching and caressing both her breasts and nipples.

"Jayne you feel so wonderful," he sighed as he felt her hand slip away from his chest.

It felt wonderful to her too. The pleasure, the arousal, the excitement and everything that was going on made her want more. It made her feel adventurous and bold. It diminished her inhibitions and she was ready to go further. In the back of her mind, she had accepted that if he wanted to she would let him fuck her. It was safe enough for any car would have to drive right across the car park and they would see the lights and would have time to adjust their clothing.

"Just a sec Bob," she whispered right into his ear as he felt her hands moving and going between them making him wonder just what she was doing. Then amazingly, incredibly and so outrageously sexily that if it had been possible he would have hardened even more Jayne slowly pulled the tee shirt up until she bared her breasts. She went on in a near croak. "And what do they look like Bob?"

Bob had never had such a thing done for him before in such circumstances and it made him feel stupendous. He simply gazed at the two medium sized breasts capped with the prominent, coral pink nipples that he could just about see in the dim light. He ran his fingertips slowly over each one across each nipple into the wide cleavage and up the slope of each boob and muttered almost in a trance.

"They are so beautiful Jayne, they are wonderful. You have gorgeous breasts."

He moved his head forward and licked the hardened tip of each of her nipples. That made her grunt with pleasure and let out a deep sigh.

"Suck them Bob," she groaned as suddenly there was light everywhere.

"What the hell?" Bob said sitting up."

"Fuck," Jayne said pulling her top down to cover her tits as they heard a voice saying.

"This is the forest rangers here, please get out of the car."

They looked at each other. "Bloody hell, we're in the shit," Bob muttered. "I'm sorry Jayne, come on we'd better get out," he said as they sat bathed in light from the powerful torches from both sides.

Jayne smiled at him. "Don't say sorry it was my idea we go somewhere quiet. It'll be ok, don't worry."

There were two average sized men dressed a bit like, well as you might expect forest rangers to dress and look, whatever the hell they are?

"Thank you, sir and madam," one of them said as Bob and Jayne stood bashfully before the pair of them. "We would like to ask you a few questions if you don't mind. I have to tell you that you do not have to answer them, ok"

"Look what do I call you ranger?" Bob started.

"Yes, that'll be fine."

"What is the problem, we haven't done anything wrong, have we?"

"Well technically probably not, but that sort of behaviour in a public place may be illegal."

"What do you mean that sort of behaviour?" he said rather fiercely.

"Look sir, my partner and I saw exactly what was going on in there."

"What you were spying on us?"

"No not at all when we see a car with no lights parked in the dark it's our job to investigate."

"So why were you looking in on us?"

"Because we need to establish if there is anyone in the car."

"Ok so once you had done that, why keep looking?"

"Because," the other ranger chimed in. "We could not avoid seeing what you were doing."

Both of them looked from Bob to Jayne and back again. Bob was sure that they were thinking 'what on earth is a young stunner like her doing with an old fart like him?'. He was partially correct.

That got Bob's temper up a little. "And what the hell has that got to do with you?"

He was getting worried the way the conversation was going for the last thing he needed was the police knocking on his door for a statement. "I'm sorry for speaking so sharply," he said.

"That's ok sir, but we do have some more questions."

"Sure, that's fine."

"Would you tell us what relationship there is between the two of you?"

"Why on earth do you want to know that, isn't it obvious?" he asked squeezing Jayne's hand reassuringly.

"Actually, no it isn't obvious, I'm sorry."

Jayne noticed Bob's difficulty.

"May I speak please?" she said beaming a smile at the two rangers.

"Of course."

"Bob is my boyfriend, that's all, is that a crime?"

"Is what a crime?" one asked."

"Having an older boy friend?"

"No of course not, but where the crime may have existed and please forgive me miss, was that there have been numerous incidents of prostitutes using the forest."

Jayne almost giggled. "Oh, I see."

"Well, I can assure you that Jayne is not a prostitute," Bob said rather pompously.

"No, I am sure you are correct, but we would like a note of both of your names and addresses for the file."

"Is that really necessary?" Bob asked.

"Well unless we get that we have to pass your car license number to the police who will then obtain your name and address and then they will write to you."

"Oh."

"I've got nothing whatsoever to fear" Jayne said rummaging in her bag and finding her driver's licence. "Here's my address."

Bob gave them his as well.

"I assume that ends this sorry tale, does it?" he asked.

"Yes sir it does, but I would advise you to be careful where you and your, er girl friend park and well you know."

Feeling totally crestfallen and really a little guilty, Jayne and Bob got back in the car and watched as the rangers walked into the forest.

"Jesus Christ, that was a mess, I am so sorry Jayne."

She leaned over and kissed him on the cheek. "No need to be, we came here because we both wanted to didn't we? Equal blame."

Bob felt such warmth and gratitude and thanks to Jayne that he held her face in both hands and kissed fully on the mouth. "God you are so wonderful Jayne" he sighed.

"Mmmm I seem to recall you saying pretty much the same thing about something else when we were so rudely interrupted," she said pushing her upper body towards him.

He kissed her harder and cupped her breast. "What can we do?" he asked.

"Well, there's always Bethnal Green assuming we can't go to your house.

"Mmmm that would be wonderful, but I can't this evening, we have visitors."

Bob dropped Jayne at the station and she went to the pub. She slept with Jack, but all through their sex she was thinking of the way that Bob had kissed her and wished that Jack could do it like that. She missed the gentleness and patience, the skill and the technique. Both times he fucked her she imagined it was Bob doing it, but each time she had to feign her orgasm.

She got up around two and went upstairs to her flat. Her mind was pretty much made up that she and Jack would have to end soon.

Directly Jayne got out of the car, Bob had phoned Philippa and told her he was running late. He got a real earful.

"Why the hell didn't you call earlier, I could have slowed the dinner down."

He nearly replied with 'Because I was in the back of my car with my young, soon to be lover,' but wisely refrained.

Despite the row and the lateness Bob stopped at the massage parlour. He was feeling so horny after what he and Jayne had done in the car that he needed more than a quick hand job by himself. He rang the parlour and learned that Sofi would be free soon so he booked her for a short session of thirty minutes.

He had to wait a while for Sofi to finish with another customer. When she eventually came into his room he was feeling edgy. He was worried about how late he was going to be and how he would respond to Philippa's inevitable interrogation after their guests left later this evening.

"Hi Bob," she said walking over and kissing him on the lips as she did now each time he visited her. He kissed her back imagining he was still with Jayne. "Lay down baby" she said pulling the towel away from him. He went to the bed watching her as she undid the coat, took that off and unclipped her bra freeing her great breasts.

"On your back first tonight I think" Sofi said lying beside him. "Want me to massage you or what?" she asked, again kissing him full on the lips, pushing her tongue into his mouth and grabbing his cock that was semi-hard.

"Let's just play," Bob said cupping her full breast and bringing it to his mouth. He had never had a nipple of two different women in his mouth in the same day before, let alone almost the same hour, he was thinking as he sucked hard on her big, hard bud.

Sofi was worried for as he they kissed and he sucked on her tit, his cock wasn't hardening as it usually did. "You ok?" she asked.

"Just a little tired I guess" Bob replied as she slithered her head and shoulders down his body. As she saw his cock she realised he had lost his erection completely. She tried hard, but it was to no avail. In fact, the more she tried the softer it seemed to go.

"It's no fucking good," he groaned after ten minutes or so.

That was a salutary lesson for him. A couple of times in the past with Philippa he'd had brewer's droop, but this was the first time he hadn't been able to get it up when sober.

*

"Phillipa is going to Portugal on Sunday to play golf," Bob told Jayne when he called her the next day.

"Really?"

"Yes, and I wondered if er, um, perhaps, well maybe," he mumbled.

Jayne's pulse had started to race when he'd said about his wife going away. She giggled down the phone. "Wondered what? If I would like to go with her?"

"No silly come here for dinner," he blurted out.

"Ooooo is that what I think it might be Bob?"

"What?"

"Never mind. What time?"

"Well she flies at seven in the evening so just in case anything goes wrong with the flight, which has been known with Ryanair, how about seven or so?"

"That'll be fine. Where do you live?"

"Oh don't worry I'll pick you up somewhere."

"Ok how about at Grange Hill station, I'll come down from Bethnal Green."

Although she probably could get out of it the crowd had arranged a darts competition for Sunday lunchtime so her plan was to play in that, pop home and change and then get the tube back to Essex.

"You mean it?" Jack asked as they walked away from the pub.

"Yes Jack we just aren't going anywhere are we?" Jayne replied as they went through the main door of the block where he had a bedsit and she had an apartment.

"But why split up? We have good sex don't we? Be truthful."

"Yes luv we do, but oh you know."

Jayne had told Jack that she wanted them to split after they left the pub and were walking down Bethnal Green Road.

"How about a goodbye fuck then?"

As it happened, they didn't have a goodbye fuck, they had two in quick succession. One, standing up just inside his front door when he pulled Jayne's skirt up, pushed her thong to one side and bent her forward. It was good, but fast and uncaring and she didn't cum. The second was with Jayne on all fours on the floor with Jack fucking her from behind doggy style. That was also good but lacked finesse and the technique she imagined and hoped Bob would have. It was only as he made her cum on the second fuck that Jayne remembered she was seeing Bob that evening.

"I'm at Stratford," Jayne said to Bob as the tube came out of the tunnel at just before six thirty.

"Where's the train going?"

"Hainault."

"Ok I'll pick you up there."

"Hi," she said opening the passenger door of the BMW and climbing in.

"Hi Jay, you look fabulous," Bob replied kissing her on the cheek.

That made her feel good. In fact, seeing Bob made her feel good, she hadn't seen him since the rangers situation a week or so ago. She wasn't quite sure why, but she felt comfortable and secure with him. She felt relaxed, yet aroused. More than anything she was expectant of what was to come. She anticipated having sex with him as being something very special.

"Thank you, kind sir," she replied just before they kissed on the lips.

"Let's go," Bob said.

"You are sure about taking me to your home aren't you?"

"Yes Jayne I am."

It was as grand a house as Jay's mums although not in quite such a desirable location, but that didn't matter. He drove straight into the garage and they went into the house, where they were in each other's arms almost immediately. Deep kisses, tongues plunging, bodies squirming and hands roaming set the agenda for the evening.

Bob had assumed they would have dinner first, but that didn't happen. Good food and nice wine might be important, but the call of the flesh was even stronger. He was as worked up and aroused as he could ever remember being, but even in that state he knew full well he would only be able to cum once in the evening. That of course, though, to a seasoned, sexual campaigner like him, would not restrict the action!

He had pushed Jayne against a wall and squashed his body against her flattening her tits and pushing his partial erection into her soft, flat stomach. They were kissing as passionately as they had done so far and their hands were roaming uninhibitedly over the other's body. It was as if them being alone with the prospect of sex before them had unleashed an enormous surge of desire and want. It was like a dam bursting. There was no longer a need to be conservative, discreet or reserved. They both knew why they were there and what was going to happen.

Bob slid his hand between them, cupped her breast and squeezed it through the scooped neck, short sleeved black top she was wearing under the long, pink cardigan similar to the one she had worn on Wednesday. He pushed the cardigan off her shoulders and they let it drop to the floor. Sliding his other hand behind her and slipping it down her back he gripped her deliciously pert bum through the thin denim of her tight, white jeans. In turn Jayne fumbled the buttons undone on Bob's long sleeved, blue, heavy cotton Ralph Lauren shirt that he was wearing with beige chinos. Without thinking she pulled the tail out from his trousers.

Having his chest bared while Jayne was fully covered felt unusually and surprisingly erotic to him. Moving slightly away from her and reluctantly taking his hands from her body he looked right into her eyes and shrugged the shirt off. He had no worries about exposing his body to her for he was slim, fairly muscular and very fit playing tennis and squash most weeks and working out in the gym regularly.

"Mmmm nice," Jayne murmured running her fingertips across his fairly, but not excessively hairy chest.

"Okay ma'am," he smiled as he closed the small gap between and went to take her in his arms again. Jayne stopped him by putting her hand against his chest.

"Just a mo," she said softly holding his gaze. Bob watched with utter fascination and desire as she took the hem of the black top in her arms and in one movement pulled it up, over her head and off.

"Oh my lord," he gasped seeing clearly the beauty and eroticism of the young blonde's breasts for the first time other than in the dimness of the car in the woods. "Jayne they are so gorgeous" he groaned taking her in his arms and kissing her again. The feel of her breasts against his chest was sensational for both of them and the almost animal like passion that had temporarily abated returned with full force.

Bob squeezed and pinched, squashed and cupped her tits and nipples. He grabbed and squeezed the cheeks of her bum, singly and both at the same time. He pushed them together, lifted them and pulled them apart visualising doing that to her again when she was naked as shortly she was sure to be.

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