Helpful Uncle Jimmy Ch. 04

More weeks went by and Uncle Jimmy realised that Chloe had taken her final "lessons" from him. He was and is not a jealous or possessive man, and was happy that she could move on in her own life: after giving him real pleasure as well. They met from time to time at family events and some holiday times. They gave a quick hug on these occasions, as befitted a niece and uncle, and no one else was any the wiser about their earlier erotic contacts.

Some months later, at a family wedding reception, Chloe came to him with another young lady alongside. "Uncle Jimmy, this is Nicola; we call her Nicky. She's my dad's sister's husband's brother's daughter. It took us ages to work that out," and they both giggled, "I think that makes her my second or third cousin or something. But anyway, here's Nicky; she's a distant niece of yours we think. She's a year older than I am," and they both giggled again.

"Hello Nicky. I'm very pleased to meet you although I can't work out how we are related; if at all," he smiled back and gave her a quick uncle-like hug. Nothing too intimate.

Chloe continued, "Nicky is a school teacher. She does languages like French, Spanish, Italian, Portuguese. Clever girl, yeah? " and Nicky blushed.

There was a two minute conversation about Nicky's work and that was the end. They all drifted off to hear the reception speeches.

Later, Jimmy found himself sitting alone with a drink on the hotel balcony, when Nicky came to him and sat down with her own glass of white wine.

"Hello again Uncle Jimmy," she started and then gave him the shock if his life, "Chloe told me you could help me with some personal matters."

"Really? What has she been saying?" he asked as casually as he could manage.

Nicky knew that she should be careful and non-committal; even though she'd actually had a detailed account from Chloe. "Oh, nothing in detail. Only that she asked you for advice about growing up and some womanly things. She thinks you're a great expert," she spoke as coolly and directly as she could, and smiled into his eyes..

Jimmy realised that this girl was either a superb diplomatic liar, or else Chloe had actually kept their secret.

"OK, so why did you two discuss it?" he asked maintaining his cool voice and manner.

Nicky decided to take the initiative. "Well, I've a problem too, and I wonder if you could help me sort it out, Uncle Jimmy," and again she looked him straight in the eyes, smiling and with lips slightly open.

Jimmy realised that the "superb diplomatic liar" explanation was probably the correct one and Chloe had "spilled the beans" as we say.

"What can I do to help?" he asked, looking her straight into the eyes in return, and smiling. He had a feeling something exciting was brewing inside this girl's brain and body.

Nicky continued with her build-up to her main requests. "Did you know that I'm living in Reddington, and Chloe tells me you're at Osborne Heights. That's only three stops on the bus route. So can I call on you one day next week, and tell you what it is?" she asked and she had her stratagem worked out.

"Of course, dear," he replied, "You tell me what evening suits you, or the weekend."

"How about Saturday early afternoon?" she offered and so it was fixed. Nicky didn't want to appear too interested in the sexual aspect of the meeting, and gave him another innocent hug although she pressed her breasts against him. "I wonder if he'll get the message?" she thought to herself.

As she walked away, Jimmy gave her a detailed look over from behind. He thought to himself, "Nice bum, hips and waist; and moves well on her wedding-event high heels." If this young woman was going to ask for his sexual "assistance" he was going to enjoy holding that shape and doing "things" with her.

Eight days later, at 1.30 pm, Nicky rang his apartment bell and he let her in carrying a big holdall bag. She gave him a somewhat bigger hug this time, and pressed her lips against his cheek. Her plan was clear in her own mind.

"Thanks for seeing me, Uncle Jimmy," she said with a wide grin on her face.

"Come in, sit on the sofa with me and have one of these little drinkies I've poured for us," he replied and led her to the seat.

They clinked glasses and each took a sip, before Nicky launched straight into her reason for visiting.

"Uncle Jimmy, I've got a sort-of boyfriend but he's not my man and I'm not his woman. We spend times together and do the sex together. But I have other men friends and he has other girls. I hope you're not shocked and can keep this between ourselves, please," she pleaded in an innocent smiley sort-of way. "How can this sound innocent?" she silently asked herself, "But he'll soon discover my wishes."

"Of course Nicky, everything you say to me is top secret to us," Jimmy confirmed, "You seem to have your adult life sorted out, so what's your problem?"

"Well, Uncle Jimmy, I'm not really experienced with this sex thing. I do it with some men I know, as well as Keith [that's his name] and it's always the same. Just 10 minutes for them to get their best moments - you know, squirting into me - and then they go away, saying "Thanks a lot." And I want more but I need to know a lot about doing the sex thing," she had rehearsed this speech ad infinitum and spoke quietly as if someone may overhear, but still looking at him directly into his eyes.

"Nicky, I'm not sure I can help. Have you spoken to Keith about it? He seems nearest to you," Jimmy suggested.

She dug a little deeper into her plot. "Oh yes; I mentioned it to him and he said something I don't understand. He said he would arrange something really special. He says it is a gang bang, where we all get together and enjoy doing the sex in different ways. I like the idea of different ways but what is this gang bang he talks about," she asked with all the appearance of innocence, carefully prepared.

"Well, Nicky, it can mean various things. But it's important that you don't get pregnant, so are you taking precautions - you know, the Pill?" Jimmy enquired.

"Oh yes, of course, I've been on the Pill since I was 18. No problem Uncle Jimmy," she confirmed and that part, at least, was true..

"Righto; let's talk about gang bang. First it could be a mixed group of men and women having sex and swapping around for different techniques and positions. Or it could be a group of men with one woman, and she pleases all of them as they try different methods and techniques on her. Or it is a group of women with one man, but that is unusual. Has Keith given you some idea what he has in mind?" Jimmy was beginning to feel out of his depth with these questions.

"Oh yes, he says himself and a group of his friends will spend time with me," she confirmed, still trying very hard to appear innocent. In reality, she wanted Uncle Jimmy to do things with her [preferably to her] as if she was being gang-banged; if such a thing were possible for one man. But Chloe had suggested that this uncle had hidden depths of sexuality; maybe of depravity.

"Hmm; do you know these friends of his? I mean how many are there and do you like them?" Jimmy asked.

"I know some of them 'cos I've done sex with them. Maybe 4 or 5; he doesn't have a big circle of friends," she explained, although she hade a secret wish that there would be more than 4 or 5..

"So how can I help you, Nicky?" Jimmy was genuinely uncertain where the conversation was going, and that he was losing control of the conversation.

"Uncle Jimmy, this is a big ask, but I would like you to show me what it will be like with a number of men on me at one time. Is there a way you can explain that and show me a little of it, also?" she replied, edging towards him and still looking straight into his eyes..

Jimmy thought for a few seconds to himself and began to construct his own plan of action with this young lady, but had the sense that she knew what she wanted.

"Nicky, can you come back another time when I've thought over this and got things ready for you. It is a big question that you've asked me," he adopted a bank-manager tone of voice and a concerned-uncle expression on his face, "I would like to help you in the best way I can. We need another day. When can you come?"

"Next Saturday, if that's right for you, Uncle Jimmy. Keith is fixing the gang thing for next month," she offered and it was fixed.

+++++++++++++

Jimmy spent the next week getting together some "equipment" he thought he would need to show Nicky what a gang bang could feel like. As a man with diverse previous sexual experiences, he already had some of the "equipment" but he got more to be sure.

On the agreed Saturday, Nicky arrived at the time she said in the late afternoon. Immediately, Nicky took the lead, "To show me these things, we need to be mostly undressed. Is that all right with you?"

"Of course. I expected that," replied Uncle Jimmy, and he followed as she went to the bedroom and started to do it.

They each undressed themselves, not each other which might have suggested an intimate relationship. It was too soon for that. Nicky left on only her bra, and Jimmy realised again that Chloe had some hand in this matter, from her own experience, passed on to Nicky.

Nicky led the way to the bed and lay down across it, with her head near one of the sides of the mattress. Obviously, she was looking for oral and probably throat activity.

Jimmy was surprised at Nicky's forwardness but had his own surprise for her. He brought two strange-looking straps from his collection on a nearby chair.

"I think you will be tied up a little, so let me try this on you," he offered.

"Oh yes, Uncle Jimmy," she complied. Her obedience had the immediate and obvious effect on his erection, which began to grow from that moment.

One each thigh, Jimmy wrapped a broad strap, about 2 inches wide; very high up; against her pubic region and almost touching her labia. He buckled them with firmness but no so tight as to constrict her movements or to pinch her soft skin in those areas. On the outside edge of each of the straps was another strap, so they formed a figure-of-eight. Into each of these external straps, he lifted and buckled Nicky's wrists. Now her hands were attached to her thighs and she could not move them expect to clench and more her fingers. Otherwise, she was immobilised in her hands.

"Will they really do this, Uncle Jimmy?" she queried with a rising tone of apprehension but also excitement.

"Maybe. I've heard of this before," Jimmy lied. He was intending to take every advantage he could obtain with this attractive and compliant young woman.

"Now bend your head back over the edge of the bed. I'll help you," and he tugged on her shoulders until her head hung down. They both knew exactly what he was going to do.

He pressed on her jaw and it opened and he presented his erection between her lips. To his surprise, Nicky opened her mouth further and started to suck him into her throat. Within a few seconds, Jimmy was shagging his full length into her mouth and past her tonsils. Any moment, he could have ejaculated but he was careful to conserve his energy and his fluids for what he had in mind in the near future. He pulled out slowly and noticed that Nicky kept hold of his erection until the very last moment as it escaped her lips.

"You're very good at this, Nicky," he said softly, reaching round to remove her bra. That wasn't so easy and he ended up just tugging on the hooks at the back so that the bra disintegrated in his hands and he tore it off her body since her arms were attached to her thighs. Nicky made a little whimper sound but then looked up into his eyes and smiled, as if to say, "That's new, how exciting."

"I heard about all this and been practising with bananas," she replied, returning to the throat sex; clearly lying and revealing her prior conversation with Chloe.

"More of this later," he said and began to swivel her around so that she lay on the bed with her head in to correct place at the head board.

"Uncle Jimmy, please look in my bag and bring the two long ropes.," she asked.

He brought from his chair two soft ropes, each about one metre long.

"Now tie my ankles to the bed somehow, Uncle Jimmy" and she spread her legs.

He attached the ropes first to her ankles and then over the side edges of the bed to the castor-feet both sides. Her legs were now spread out a long way and unable to move, and her arms fixed at her thighs.

"Someone will put this into you, I'm sure," he said and spread lube gel around her pubic region; all over the area between her splayed legs. And he pressed the pump so that some worked its way up into her vaginal opening; and pushed a little with his fingers into her bottom, past the sphincter.

"And they'll do this, probably," he spoke softly as he produced a blindfold from his collection and slipped it over her head.

Nicky was silent but inside she was even more excited and roused by the knowledge that Jimmy would do things with her and to her, that could come as surprises in her blinded state.

With little preparation, he lay on her and edged his erection between her labia and up into her vagina. She was open and smooth and wet, even without the gel he had applied. "This lass is ready for anything," he thought to himself.

Lying on her and handling her every way he could, he shagged into her with increasing vigour while Nicky was forced simply to lie there, restrained, staring blindly at the ceiling, and feeling her body bounce around under his; and wondering what would happen next. But she was excited, she knew that, and was hoping for more than she had experienced before; which hadn't happened so far.

Again, careful to contain his excitement and fluids, Jimmy held off from his climax and limited himself to a rough shag for 5 minutes or so,. He handled her body all the way from her throat, to her breasts, to her waist, to her thighs, to her buttocks and so to the straps on her thighs.

Jimmy thought to himself, "She seems ready for anything, and there's one more hole to go, before I move to the next stage."

Leaving her vagina, Jimmy went to her ankles and undid the two ropes. Then he pushed her feet upwards and backwards so that her knees were pressing against her breasts. Jumping off the bed, he attached the two ropes to the corners of the bed head, either side of the main headboard. Now Nicky was spread out and open in a new way, and her perinaeum totally exposed. Her labia also were spread slightly be the sideways pressure of her leg-spread.

Jimmy reached over to his collection and brought a medium sized butt plug; about 2 inches across and 6 inches in length. Slowly he felt his way into her anus with it; in and out; gradually getting deeper. In a short time, it was full length into her rectum with her anus closing round its stalk; and he had felt the slight resistance of the shit which also occupied her lower bowel. "This girl isn't new to this," he realised, as she accepted the plug and relaxed to his movements; even at both sphincters, "She's not so innocent as she pretends. So why is she here, pretending to learn something?"

In fact, until this point, Nicky had started to get frustrated; nothing very new seemed to be happening. She was starting to feel disappointed in Jimmy and in the idea that Chloe had passed to her. But now, the bondage and the positions were new to her and she began to experience new sensations in her lower abdomen. "Perhaps he will do more exciting things from now on," she thought to herself.

Almost as she had the thought, Jimmy brought another object from his pile on the chair. It was a penis shaped dildo; 8 inches in length and 1¼ inch in width. It slipped between her labia easily and up into her vagina. As a special effect, Jimmy had thought this through beforehand and attached a very broad piece of rubber band to the two leg bonds, on her thighs. It kept the dildo in place and he complimented himself on his ingenuity.

Inside the blindfold, Nicky was feeling full and wondered what would come next. She had a feeling that he was moving to something more complicated; maybe scary and outrageous.

Jimmy untied the bed head ropes and turned her round on the bed again, with her head over the edge of the mattress; leaving her thigh and hand bonds in place.

"Now Nicky," he said softly, "in a gang bang, you'll be taken by three men at once - at least. So try this!"

He entered her mouth and throat again with his erection and leaned forward to press on the two objects penetrating her from between her legs. This was his extra surprise; he pressed on a small switch on each of them and they sprang to life with pulsing vibrations.

Nicky was unable to speak or express any opinion or feeling, because Jimmy was deep in her throat, but she tried with a series of grunts and mumbling sounds as he withdrew on each stroke. Also, she tried to move her body around but that was impossible because of the bonds and his hands on her breasts.

"There, Nicky, you're being shagged by three men at once," he said, "and they'll keep at it until they are all satisfied."

This went on for some time and Nicky began to work her way to orgasm. The vibrations and the excitement of the situation were overwhelming. She was tied up and restricted and stretched but the orgasm came from her lower body and she would have cried out but could not. And Jimmy controlled himself to prevent his own ejaculation. But Nicky bucked around on the bed, arching her back and trying to move her feet and hands; as the wave of pleasure coursed its way through her.

And she expelled a huge volume of urine and squirted over herself and the "toys" inside her body, and onto the bed sheets. Fortunately, Jimmy had foreseen such an event and had laid down another waterproof sheet across the full width of the bed.

In the end, Jimmy pulled himself from her throat, his erection covered in mucus and maybe some regurgitation. He leaned forward and switched off the objects inside her. He was pleased that she had reached an orgasm but also was satisfied to have done something new for her. He decided to release her and see how she would handle the situation.

Accordingly, he removed the plug and dildo, and released her hands and legs from the ties on her thighs.

From inside her blindfold, lying released across the bed, she spoke more of her own plan, "Uncle Jimmy, please go to my bag again and bring the broad belt."

Jimmy found a leather belt about 3 inches in width and with sets of double holes around it, fitting into the double prongs of the buckle.

"Put it round my waist, Uncle Jimmy, and pull it tight, please," Nicky instructed.

Jimmy did this, feeding the belt under her body and adjusting it to her waist position. He closed the belt with some tension and buckles it.

"Tighter, much tighter," she instructed and he obeyed, using all his strength to force the belt as small as possible on Nicky's waist.

"In a few minutes, make it tighter still," she said, "I like the feelings inside me when it is really tight."

While the minutes passed, Jimmy turned her round with her head on the pillows, and lay beside her. He ran his hands over her and played gently on her breasts, mound and vulva: not wishing to interrupt her relaxation after the orgasm. "I wonder what she has in mind?" he asked himself, "if her waist is made very small."

He kissed her nipples and down to her pubic area, and soon Nicky spoke again; still blindfolded. "Tighten it again, Uncle Jimmy. Make it very tight indeed. Tight as possible," she said.

Jimmy raised himself and undid the buckle, which had come a little loose over the minutes. By using all his strength, and forcing the belt through the buckle, he was able to take another four holes against the prongs. Nicky's waist looked minute, tiny, impossible.