Never Too Old To Learn Ch. 02

Brett let her legs go while he went off to retrieve the butt plug from a drawer. He was back in a flash, holding the odd shaped item and a tube of KY.

She used her own arms to willingly draw both legs back again, holding them up high while she felt his fingers coating liberal amounts of KY on the inner cheeks of her arse and inside her anal opening. Jennifer let out a gasp as she felt the tip of the butt plug go round and round the rim of her anus before Brett centred it and pushed it gently forward, pressuring her sphincter to accept it.

"Push out like you want to take a shit," he told her. She did as he suggested and found it worked. Her anus seemed to suck the cone-shaped tip up inside her. "I will take it slowly, so don't panic. Just try to relax your whole body. Think about sucking my cock or something good like that."

She attempted a feeble laugh at his suggestion, but after about a minute she did seem to relax her body. Brett knew that the next stage would be difficult for her. The butt plug was like a triangle and now he must force the body of the object into her arse. It would get thicker and thicker the further he pushed. She just had to tolerate until he could get the bulk of the butt plug inside her and then the narrow part underneath, with a flat flange below, would hold it in place.

Brett began to push it slowly but steadily into her, encouraging her with words, "Going great, Jen … that's the way … stay relaxed … not much more…"

She coped quite well, but when the thickest part was stretching her tiny anus wide, she reacted, "Oh God no … Brett, it hurts … no more please."

"Not much more, honey … hang in there … just an inch … you've almost got it."

"Oh God!" she screamed, her fingers clawing at the sheet as the thickest part of the butt plug snapped through her tiny opening and her anus was able to shrink back and close over the narrower base of the plug.

"Good girl, you've done it. That's it, no more pain. It's snugly in place now. How does it feel?"

"I'll tell you in a minute. I'm still getting over the pain of the thickest part going in."

"You can let your legs go for me, Jen. We don't need you so stretched now."

Jennifer released her hands from her legs and gingerly stretched them out on the bed again, making little whimpering sounds as her anus tightened around the intruding plug.

"How's that, Jen? What are you feeling now?"

"Well, I can certainly feel it, but it's not really painful … it's just an odd feeling … perhaps a bit uncomfortable, that's all."

"Good, that's how it should be. You will know it's there, but it could even make you horny. And as you walk, it will shift around a little, might be quite sexy."

"Umm, we'll see about that. Let me stand up, see if I can cope with that."

He got up from the bed and helped Jennifer slide across to the edge. She grimaced when she slid on her bottom because her weight on the bed pressed the butt plug tighter inside her. She stood up carefully and took a couple of steps. "Feels funny, Brett."

"Yes, it will take a bit of getting used to. The idea is that if you can leave it for 24 hours, it will open you up a fair bit and I should be able to get my cock up your arse next time."

"What if I want to go to the toilet?"

"You can pee normally, but obviously you're going to have to take it out if you want to take a shit. Then you'll have to put it back in yourself."

"Oh my God, I don't know if I can do that. It was hard enough having you push it into me. To inflict that much pain on myself, I think I'd want to give up."

"Try to do it for us, Jen. Trust me, you've got to give anal sex a go some time in your life. There's no time like the present."

After walking through his house a bit more, even walking up and down the stairs, to test out the wearing of the butt plug, they returned to his bedroom and spent the rest of the afternoon enjoying oral sex. Brett did Jennifer first, and then she sucked him, although she was only able to get the head of his cock inside her mouth. She did it well though because he blasted a surge of cum deep into her throat, and she swallowed for the first time in her life.

She wore the butt plug the rest of the day. She felt odd at work, talking to the people that worked around her, knowing that she kept a little secret from them. That a butt plug was beneath her clothes, stretching her tiny anus to later admit her work colleague's large cock for an illicit bout of anal sex. The thoughts excited her and the evening passed quickly.

When she got home and changed into her nightdress, she wondered if she should remove it, for fear that her husband might see the shape of it beneath her nightgown. But with nothing sexual from him in three years, Jennifer decided it was safe to walk around in his presence … he would never notice her – or it. Besides, he was already in bed, it would only be at breakfast that he might spot the shape of it. She could stay in bed until he had left for work.

Jennifer felt the pressure of it a couple of times when she rolled over in bed through the night. But after breakfast, she felt movement in her bowels and realised that she would need to go to the toilet. The butt plug would have to come out. In the bathroom, she squatted down on her haunches on the floor, trying to stretch her arse enough to make the plug's exit easier. She got a firm hold of the flange base and pulled on it, but quickly realised this was going to be much harder to do. It was tapered from the tip so that it gradually got thicker as it entered her. But to pull it out, she would suddenly feel the thick base pulling through her anal opening. She pushed her bowel muscles, wary of pushing too hard for fear of shitting at the same time. At last, the thickest part of the plug passed through her tiny anus – it hurt - and she emitted a huge sigh of relief. "It's not going back in," she told herself as she washed it in the bathroom sink.

Brett was very disappointed when she told him later that morning that the experience wasn't for her. She said that she hoped that her reluctance to have anal sex with him didn't spoil their newfound sexual relationship. But his reaction implied to her that it might. He immediately told her that he didn't have time for sex with her today and that they should have their meeting and she should leave then.

'How shallow is he if he only wants me for sexual experiment?' she thought as she drove her car back from Brett's house, her arse still a bit uncomfortable from having the butt plug up inside her for 20 hours. 'Hopefully, it's just a display of childish petulance that he didn't get his way.'

It did seem like that's what it may have been. He was extremely warm and friendly to her through the show and at midnight, he came to her to urge her to be at his house at 10 the next morning for their regular meeting.

"Should I be expecting extras too?" she asked.

"Of course," he told her encouragingly. "Dress appropriately!"

Chapter Eight

Wednesday morning, Jennifer was up early, feeling so good about her new sexual relationship with the young man with whom she also worked. She hadn't realised just how much she had missed having regular sex over the past three years. She wasn't hungry so she skipped breakfast. 'Why don't I go over early and we can get some fucking in before and after our regular program meeting.'

She drove quickly down the Canyon Road and found herself at Brett's house just after nine. She let herself into the house and hurried down the short flight of stairs to the bedroom floor. Even as she peeped into Brett's bedroom, noting that his bed was neatly made, apparently unslept in, the sounds from the floor below were loud and unmistakable. Jennifer was about to be exposed to watching another live sexual coupling.

She had lost her haste. The way things had been going between them, did she really want to see this? And why was he doing it with someone else? Her feet moved slowly, taking her down the hallway, closer to the frantic sexual sounds coming up from the living area. Reluctantly, Jennifer edged closer to the railing and peered over to the floor below.

Up on the lounge was a woman on her hands and knees, Brett also on his knees, was behind her straddling her body, his chest over her back, his hands around and under her, obviously fondling the woman's breasts. The activity was hard and heavy, the woman sort of screaming with each hard thrust from Brett. Perspiration ran down Brett's back, it looked to Jennifer like they had been at it for a while.

She watched fascinated … and despite her believing she was now Brett's lover, she was nonetheless, excited and turned on by the sexual conquest that she was witnessing. She watched as he straightened his upper body, his hands withdrawing from under her to rest on her hips, gripping her firmly. Jennifer was above the copulating couple, virtually looking over Brett's shoulder. She could see exactly what he could see of the bent over woman beneath him. She knew that he was looking down, watching his own huge cock penetrating this woman's…

"Oh my God, no … he's in her arse. I wouldn't do it, so he's picked up a woman who would. Oh no, please don't hurt her with that big thing of yours," she begged quietly to herself, amazed that she seemed more concerned at the physical hurt that this woman might feel than her own mental hurt at having to watch it.

The sexual exhibition below took on a new significance. Jennifer was racked with a hundred questions. Was he doing this because he was desperate to try anal sex – and she had denied him? Was he doing it with someone else to show her that it was possible to do in spite of his remarkable size? Having resumed picking up women in nightclubs – was this a signal to her that he and she were through as a couple?

She managed to tell herself that none of the above might have any significance because she had arrived early – very early. She convinced herself that Brett had not actually meant for her to see this sex act at all. His bed was unslept in because it was being kept fresh for her 10am arrival. She now believed that he would have this woman out the door by ten. She should just go and get into Brett's bed and wait there for him … pretend that she never saw him sodomise this young woman.

But as much as Jennifer wanted to do just that … to walk to Brett's bedroom and lay down to wait for him, her feet were stuck to the floor, her hands would not release their grip on the railing. She was fascinated to watch her young lover fucking this woman in the arse. Jennifer leant over the railing, craning to see more closely, watching avidly. She felt her own anus twitching, clenching – almost as if she herself was feeling every carnal thrust of Brett's hard cock into the woman's tender rectum.

She watched – and she listened – as the woman screamed out in pain or pleasure, or both, "Oh Brett, fuck me in the arse … yes, fuck me!"

And Jennifer watched his final hard thrusts, heard his anguished gurgling exultation of lust as his body jerked and spasmed over the woman's back, his cock by now obviously spewing its creamy cum deep into her arse.

Only when the noise below had stopped, when all movement had ceased … only then did Jennifer tiptoe away to Brett's bedroom, closing the door behind her, removing all of her clothes and slipping under the sheet to await her lover's arrival.

Jennifer lay there nervously, wondering what was happening downstairs. Surely by now, Brett would have withdrawn his hard-on, still dripping with his cum, from out of the young woman's arse. Would he be telling her she had to leave now because he was expecting someone to arrive at ten? Jennifer looked at the bedside clock … 9.40.

She had a sudden fear that maybe Brett wasn't going to push the woman out by ten. What if he didn't care about hurting Jennifer … what if any moment, the bedroom door would open and he would bring this woman to his bed? How embarrassed would Jennifer be lying there naked?

Jennifer was racked with mixed emotions. How could Brett do her in his bed at ten when he had just fucked this woman in the arse? He was going to need some recovery time. Just as she was determining that getting into his bed naked was a bad decision, she heard voices outside the bedroom door. Jennifer's hands gripped the sheet and pulled it up tightly over her naked body, just her hair, eyes and nose visible.

Then there was silence again and the door suddenly opened. Brett walked in alone and Jennifer breathed a huge sigh of relief, her hands relaxed their grip on the sheet. She even threw it back, exposing her bare breasts as Brett walked toward the bed. His cock hung limply, but even in that flaccid state, its size was impressive and she longingly admired it.

"Well, well, who's been sleeping in my bed?"

"That's the second time you've quoted from that book, you must be a big fan of The Three Little Pigs."

"I'm not a great reader, that was the last book I read. You see, I don't get much time to read, there's always some woman around who wants my body. Why are you here early?" His question was almost aggressively accusatory.

"I woke up early, wasn't hungry … at least not for food. All I could think about was having that monster penis of yours again."

"How long have you been here? Did you see what was happening downstairs?"

"Saw it and heard it, you both put on quite a show. Looks like you found a woman who would let you use her arse."

He smiled, "Yes I did."

"Was it all you thought it would be?"

"And more … she was so fuckin' tight. Shit, it was good! You don't know what you missed."

"I wonder if she was as enthusiastic as you."

"She sounded like she was."

"Yes, she did indeed. Did you use a condom in her?"

"Of course."

"Then what are you standing around talking for? I would like you in me now, it's ten o'clock."

He smiled again, "You have become quite a sexpot, Jen … just give me five minutes."

Brett turned and retreated to the en suite bathroom and Jennifer heard the shower running. The water was only on for two minutes, his body was still quite damp as he returned, approaching the bed. His cock was half-rigid now, Jennifer assumed he must have worked on it with his own soapy hands.

"Are you going to need my help with that?" she offered.

"No, I'm about to go down on you. I love the taste of a woman's cunt, that should have me up in no time, and you can expect to reap some side benefits from me doing it."

Brett grabbed a hold of the sheet and threw it back, exposing the rest of her naked body. Under his probing gaze, she let her legs slide wide apart. "Don't hold back," she told him as his head dipped down between her spread thighs and she felt the flat surface of his wet tongue painting up her pubic slit, all the way to her clitoris.

They had a good session in bed together. After bringing her to orgasm with his tongue and lips, his body hovered above her and she could look down and see that he had fully recuperated from the episode in the other woman's arse. Brett gave her one of the most solid work-outs that they had yet enjoyed. Having used up so much cum in his prior encounter, he was in no hurry to finish and he brought her off four times before at last he could muster up enough fresh supply to make a deposit in her juicy cunt.

When they lay there in the after-glow, Brett surprised her by talking about his family. He had mentioned them only once before … they all lived out of town. But he had never talked to her in detail about them. It seemed that his mother had died of cancer two years ago, leaving his father to run the family farm with Brett's younger brother. It turned out that Brett was only talking about it now because his dad had asked if he could come to town and visit with him.

"He's coming in on the 8 o'clock train tomorrow night. I will of course be on the radio at that time, so I have mailed him a spare key and told him he's going to have to get a cab over here from the station.

"A cab ride could be expensive, it's a fair distance, Brett."

"I mailed him fifty bucks too. I'm just telling you about his visit, Jen, because it's going to curtail our stuff for a few days. I'm sorry, but he's family."

"Sure, that's okay," Jennifer told him, but thinking to herself how embarrassing it might be. "Brett, your dad is probably around the same age as me, maybe a couple of years older. I'm worried about what he may think of me, having it off with his son."

"Jen, don't stress over it. I have actually told him about you."

"Oh my God, what? Have you told him about us having wild uncontrolled sex?"

"No, don't worry about that. No, I've told him about how good you are at work things, how you've taught me all this stuff about doing talk back radio."

"Oh, that's alright then … and you've not said anything about us doing this sort of stuff."

"Well no, not really."

"Brett, what does that mean?"

"I just sort of said that we had become quite close, good friends … and I left it at that."

Jennifer was not totally at peace with Brett's reassurances, but she would have to wait and see how much his father seemed to know about them.

Chapter Nine

The next morning - Thursday, Jennifer arrived at his house at ten. She did not intend to make any more early surprise visits. It was the first really warm day of summer and she figured that at some time that day she would christen Brett's swimming pool. When she walked in, she was surprised to find Brett dressed and looking like he was ready to go out.

"What's with you, I thought we'd have some play time before we work?"

"Sorry Jen, I've got some chores to do this morning. Dad's coming in on the train tonight and I haven't got any proper food in the house. Plus I need to buy a few things for the second bedroom, make it look a bit livable. Honey, make yourself comfortable, I'll be about two hours. When I get back, we'll do the program preparation for tonight and then after lunch, what about we have an open air fuck out by the pool.

"You are such a romantic, Brett."

He grabbed his car keys and was gone, leaving Jennifer standing there, wondering how she would fill in the next two hours. She had thought about a swim, now it was definitely on the agenda. She had not brought a costume with her, but then she wouldn't need one. No other property could look in on Brett's hillside pool.

Jennifer swept down the stairs, confidently shedding her clothes as she went, eventually getting down to only panties and a bra by the time she reached the wide open doors of the living area that opened out onto the pool. She stood for a moment looking across the pool taking in the superb ocean view beyond. Then she reached behind her to unclasp her bra, easing it off her breasts, and then hooked her thumbs into the waistband of her panties and pushed them down over her hips.

Jennifer stood resplendently naked and alone in the doorway, then she took five steps across the patio to the pool edge and dived in to the cool water. She swam several laps, then hauled herself up the side, walked over to a poolside chair, straightened it so that it was more a bed than a seat and lay face down to soak up some sun rays on her pale back. She hadn't brought a towel out with her, so she could not dry her back, leaving her skin very damp with beads of water.

The only sound was the waves breaking on the rocks below the house and the occasional call of a bird flying by … and then suddenly the sound of a male voice she didn't recognise. "You would have to be Jennifer … Brett was right, that's the finest arse I've ever seen … a perfect ten."