Jesse The Stripper

Chapter One

Several months after Jesse had her first experience with her three boys, she and Robert were spending another evening with them: Paul, Michael, and James. This was the fourth time they had all got together. Jesse had enjoyed herself immensely every time, and Robert loved watching her with the guys more and more.

It was late and after three rounds and a lot of wine, everyone was tired. They were all going to sleep in the hotel suite they had hired together, but Jesse wanted to strip for them one last time before they called it a night. She had showered, and she had returned from the bathroom wearing a black bra and panty set, with black stockings and suspenders. The guys were all sitting around naked. That is the way Jesse liked it. She liked to see the effect she was having on her adoring audience as she danced and stripped.

She put on some slow music and began to dance. Her body swayed to the rhythm and the guys watched her. She danced and slowly took off her bra and after her bra, her panties. When she strips for her boys, Jesse likes her shows to be very explicit. She loves to show herself off. She sat back in a chair and spread her hairy pussy as wide as it would open. She was wet and her red cunt flesh glistened in the soft light of the room.

From the table beside her, she picked up the dildo she had placed there, ready for when she needed it. it was a large dildo, about eight inches long, but not too wide. A woman loves to be stretched; not too much, but she loves to be filled and feel the end of a cock deep inside her. Jesse had been fucked by James' monster cock many times, and an eight-inch dildo she can now take with ease. Her hungry pussy swallowed that lewd toy in one go. she fucked herself with it and gasped with pleasure as she pushed and pulled it in and out of herself. The boys watched but Jesse could tell they were not as excited as they are at the beginning of an evening together. She was not surprised, because they had all been going for hours. They had all fucked her many times that evening. Jesse, however, loves to be desired and she needs to see the desire in the men she performs for. She had an idea.

She pulled the dildo out of her pussy. She went to the kitchen and came back with a bottle of olive oil. She poured some of the oil onto her hand and then she leant against the back of the chair she was sitting on. She oiled her finger and pushed it into her arsehole. She finger-fucked her arse for a minute and then pulled her finger out. She picked up the toy again and poured olive oil over it. She lowered herself into a chair and leaned back so that her arse was raised. She held the dildo at the entrance to her arsehole and slowly pushed it in. She gasped with pleasure and pain as her rubber cock penetrated her virgin arse.

She watched the boys watching her. 'Whoa!' shouted Paul.

'I have your attention now', she said. All four men watched as Jesse fucked her own arse with her toy. Robert could barely believe his eyes. They had never done anal much, and on the few occasions they had tried, Jesse had said she found it too painful. Tonight, though, she was gasping and crying out with pleasure as she pushed her toy up into her arsehole until six inches of it had disappeared into her dark hole.

As she pushed and pulled it in and out, Robert said 'look at the way her ring moves in and out as she fucks her arse'.

Jesse liked that and told Robert to film her. He grabbed his camera and started filming. Jesse's excitement intensified when the camera was on her. She beckoned to James to come over. She told him she wanted to suck his cock and he positioned himself so that she could get his cock into her mouth. The others watched as Jesse fucked her arse with her toy and sucked James' big black cock. She reached orgasm and cried out, and in the same moment, James shot his first shot of cum into her mouth. She took everything he had in her mouth and sat up and let his spunk dribble from her mouth down her chin and drip onto her magnificent tits; her dildo still up her arse.

When she returned from the bathroom after refreshing herself, Jesse sat down with her boys. Everyone was tired now. They had gone three rounds and a strip show finale, and it was almost two in the morning, but they chatted a while longer before they slept.

'You know,' said Paul, looking at Jesse, 'you'd make a fantastic stripper'.

'I thought I was a fantastic stripper', she said, a little annoyed.

Paul sensed her had offended her a little and he quickly added, 'I mean in a strip club. The audience would love you.'

'At my age?' she said, incredulous but excited at the idea. 'Are there professional strippers of my age?'

'All ages, shapes and sizes,' said James.

'But an audience of strangers,' said Jesse, almost as if she was thinking aloud. The thought quickly took root and she liked it. she would leave it to grow.

Robert saw that she was interested, but he sat silently, listening. Watching Jesse strip in a strip club would be fantastic, but again, how could that be made it happen.

'Would it be so different from flirting and teasing at a casino? The men there are strangers, and if anything, stripping at a strip club is even safer than playing flirt and tease games at a casino. You'd be nude, but everyone knows the rules, look but don't to touch, or touch only if you're invited to,' said Michael.

'There are strip clubs where the men can touch the strippers?' asked Jesse.

'Oh yes,' said Paul, 'touch and much more. After hours private parties.'

'I never imagined,' said Jesse, but she began imagining now, and she went on imagining over the following days.

Chapter Two

A few evenings later, Robert and Jesse had sex and afterwards Robert told Jesse she had surprised him when she stuck the dildo up her arse. 'I didn't think you liked anal. Whenever we tried it, you said it hurt too much. And I don't even have a big dick. I thought you were going to ask the boys to fuck your arse.'

Jesse laughed and said, 'James! With his cock, he'd rip my arse to pieces'.

Robert smiled and said, I think he would.'

The conversation ended there, and Robert did not give anal sex much more thought, but he was very excited at the idea of Jesse as a stripper. Jess was excited about being a stripper, but following what Robert said, as they lay there side by side, she was thinking about anal sex. It was true what he had said; she had found it painful, and it was also true that Robert's cock was not big. However, since she had begun having sex with other men, she had become more and more adventurous, and she had wanted to try more and more things, to see what she enjoyed.

One evening, when they were all together, after they had all had sex a couple of times, James asked Jesse to give him a golden shower. She had to suppress a giggle. Piss and pissing had never excited her sexually, but she had thought, why not? She had seen it in porn, but Robert had never asked her to piss on him, and she didn't fancy having someone piss over her. She had gone with James to the bathroom. The others had followed them to watch.

James had laid on the tiled bathroom floor and Jess stood over him, squatted, and pissed over his chest and face. She had been unable to stop herself from giggling, but that did not seem to spoil it for James. She had looked down and watched him open his mouth. Spontaneously, she had stopped moving, so that her jet went straight into his mouth. Watching James drink her piss really excited Jesse. It gave her an incredible feeling of power. A man desired her so much, he was willing to drink her piss.

She had enjoyed the boys' reactions when she had fucked her arse with her dildo too. She had felt so deliciously filthy and slutty with that lewd toy up her arse. Anal sex seemed very exciting now and she imagined her boys taking turns to fuck her arsehole, as Robert watched. At the same time, she was wise enough to know that the idea and the reality are not always the same. To fantasize about an anal fucking did not hurt her arse but doing it might. She wanted it, but she would wait for the moment to do it, if that moment came. However, she did practice when she was home alone, using olive oil as a lubricant to ease her toy past her tight sphincter and into her equally tight rectal canal. With practice, it became more and more comfortable, and her anus opened more and more readily, and became more and more sensitive to stimulation. She knew she was ready to take cocks up there, and she knew that one night she would. It was simply a matter of when.

Chapter Three

Robert knew Jesse liked the idea of being a stripper as much as he liked it, but as always he left her to decide what she wanted to do. He knew she knew he would want her to do it, but how to set it up? He did not know They had not known how to set up Jesse's first time with her three boys, but fate had intervened, with a helping hand from Paul and Robert, so who could say what might happen.

Fate did indeed intervene again, but this time it was Michael, not Paul who called, and it was Jesse, not Robert who picked up. Jesse did not recognise Michael's voice at first. Usually, Paul called. Michael seemed hesitant. He asked if Robert was home. He would be more comfortable talking to him about what he wanted to propose, but it was Jesse who had answered his call, and Jesse he would speak to, and it was Jesse he wanted to talk about.

'Robert's out, but you can talk to me.' It did feel a little strange. Here she was talking on the phone to a man she had met four times, and had sex with him, and now something as normal as a phone conversation seemed something unusual.

'Ok,' he said, 'what I wanted to suggest to Robert is about you, anyway.'

'Ok,' said Jesse, 'you've got me curious.'

Michael recovered his poise and he spoke confidently. 'Do you remember we joked about you being a stripper the other night?'

'Yes,' Jesse replied and laughed.

'It can be arranged, if you want to.'

Jesse was surprised, but the thought of it immediately excited her. 'Wow, how?'

'I know a guy who owns a strip club. If I asked him. He would put you on the bill one Saturday evening, or you could do an after-hours private party.'

There was a pause before Jesse said, 'A private party. What would that be like?'

'An invited audience of regulars at the club. Some friends of the owner and manager. Me, James and Paul, Robert. A few strippers. The shows are raunchier than the regular evening stuff. You could go as far as you wanted. It would be up to you.' Another pause. 'I'd make sure you were top of the bill,' added Michael.

'Definitely top of the bill', Jesse said and laughed.

'I'll leave you to think about it. And think of it as an open invitation. You can do it whenever you want, if you want to.'

'Do you think I should?' she asked him.

'I know I would enjoy it, but only you know if it's for you.'

'I'll think about it,' said Jesse, 'and I'll ask Robert and see what he thinks'. She was sure she already knew what Robert would think.

Michael was about to say goodbye and ring off when a thought came to him. 'If you're not sure, there's a woman I know, on the scene. She wanted to do it and I arranged it for her and she had a good time with it. You could talk to her. I will ask her and if she's happy to talk to you, I'll give you her number.'

'Ok,' said Jesse, 'yes, I think I would like to talk to her.'

'Ok, see you,' said Michael.

Jesse was interested in stripping at this club, but she thought she would first like to talk to this woman who had already done it. She would also like to talk to her about swinging and what she had done and what she got from her experiences.

A few hours later, Michael called back and told Jesse that his friend would be happy to talk to her, gave Jesse the number and told her that the woman was home most evenings, and Jesse could call whenever she wanted to.

Jesse called the woman, who was called Helen, a few days later. They chatted for about half an hour. Jesse told Helen her story and Helen told Jesse hers. Helen seemed to enjoy the opportunity to talk to another woman who shared her fondness for swinging. She told Jesse that she and her husband had started about twenty years ago, when they were in their early forties. Children had grown up; their sex life had become routine and got a little stale. Helen had been tempted to take a lover; she liked younger men, but she had decided not to. Instead, she had suggested swinging to her husband, and had been pleasantly surprised when he responded enthusiastically. She told him about her interest in younger men and he said he had often fantasised about watching her with other men, but he had never imagined she would be interested in doing it. They had begun by going to nudist beaches and then swinging clubs. Over the years, Helen had done everything she had wanted to do; gangbangs, group sex, threesomes, she had experimented with having sex with women and enjoyed it, and she had discovered a love of watersports, and she loved pissing over her lovers. Recently though, she and her husband had slowed down a little and she had now two regular younger partners and met them every month or so, sometimes one of them, and sometimes both together. Her husband always came along and watched. He did not join in so much anymore.

Jesse told Helen about her pissing experience. She said she had not been turned on by the act of pissing on a man itself, but by the man's reaction. Helen responded by saying that on the swinging scene, the important thing is only to do things you enjoy. If you don't want to do something, tell your husband, 'no'. Jesse agreed and explained to Helen that she felt that her happy marriage had become happier and stronger since she and Robert had started swinging, and she told her of how she felt even more confident about her looks, her body and her attractiveness than she had before, and she was feeling more and more adventurous sexually and wanted to try new things.

'Like strip at a strip club,' joked Helen.

'Yes,' said Jesse.

'Are you going to do it?'

'I think so,' Jesse said.

'I enjoyed doing it,' said Helen, and went on, 'I asked Michael to set it up because I knew his friend owned a strip club. It was an after-hours private party. They called it 'Granny Hour'. There were two other women. One was a professional stripper. She was about sixty and she'd been a stripper all her life, and then me and another woman from the swinging world. Michael must have invited her to do it too. The pro stripper went on first, to warm up the audience. Then the other woman, and then me.'

'What did you do? How far did you go?' Jesse was getting excited as she asked.

'When we were preparing, the club owner told us we could go as far as we wanted, as long as it was legal! Going into the audience was fine, and so was interacting sexually with members of the audience. We could also bring men up on stage and have sex with them.'

'Wow,' exclaimed Jesse.

'Before I went on,' said Helen, 'I really didn't know what I would do or how far I would go. For sure, I was going to dance and tease and give them some spread cunt, but I had no idea whether I would go into to the audience or get men up on stage.'

'So, what happened? What did you do?'

'the pro stripper had kept it quite tame. She did some spread cunt sitting on a chair on stage.'

'That's tame!' laughed Jesse.

'Yes, compared with what followed. The woman who went on after the pro and before me did the same as the pro, and then she went into the audience, and gave hand jobs and let guys suck her tits. Then, she got two guys up on stage and gave them both blow jobs. She took them all the way and they both spunked over her face.'

'And what about you?' asked Jesse, 'after that.'

'I knew I had to go further, because I was top of the bill, and that's how it works. The acts get hotter and hotter. The moment I got up on the stage, I knew I would do anything to please the crowd, anything I had to, to make them desire me more. I danced, stripped, did the spread cunt thing, and then I went into the audience, I had a toy and I invited guys to push it into my pussy. I did some hand jobs. I let some guys suck my tits and finger me. I did a few blowjobs. Then, I picked two guys from the audience, both young, and got them upon stage. I had sex with them both. We did everything! For the grand finale, they dp'ed me, one in my pussy and the other up my arse. I love that!'

Helen ended by reassuring her that it would be a safe environment to live out the fantasy of being a stripper. Jesse said, 'you've persuaded me. I'm going to do it.'

She would tell Robert when he got home later in the afternoon.

Before ringing off, Helen told Jesse that Michael has asked her if she wanted to be part of it, if Jesse decided to go ahead, and said she would, if Jesse wanted her to.

Jesse thought for a moment and then she said, 'usually, I'm a greedy bitch and I want all the attention, but I think I would like you to do it too.'

Jesse was so excited at the thought of what she was going to do, she went to the bedroom and masturbated and fantasised about stripping before a crowd of a hundred men and feeling their desire for her, and sucking cock after cock and being fucked and fucked over and over again, by every man there, in all her holes.

It was after dinner when she told Robert that the strip club date was on, if he wanted to do it. she knew he would. Robert called Michael and asked him to set it up. An hour later, Michael called back and told Robert that it was all arranged and it would be on Saturday night; that was two days away.

Chapter Four

A stripper on a stage is an actress, which is why strippers often wear themed outfits. Jesse gave a lot of thought t what she would wear for her big night and in the end, she chose to go as herself and she wore her favourite and most daring casino flirt and tease outfit. A red bikini top, a matching red blouse that was open at the front down to her belly, a long wrap around chiffon scarf in a lighter red, a black mini-skirt, and red very high-heeled shoes.

The strip club was close to a casino, and they were asked to arrive late. The show would begin at midnight. They would go to the casino first. Jesse would get herself in the mood with some flirt and tease there, and she would drink some wine, to calm her nerves, for she was a little nervous. However, she was not going to back out; her excitement at what she was going to do was stronger than any fear she had.

Helen had called Jesse the evening before, to say that she was going to go on first and she said she would do a spread cunt show, but she would not interact with the audience.

'That should leave you plenty of room to go further than me as the headline act',' she had joked.

Jesse had decided what she would do, and wondered how far she might go beyond that, if the mood and the moment took her. She would do spread cunt, dildo in pussy and, prompted by her growing interest in anal sex, dildo in arse, as she had done for Robert and the boys. She did not yet know if she would go into the audience, or if she would bring any men up on stage. She knew that she would not know whether she would do any of that until she was on stage herself.

Jesse is an intelligent woman, and she likes to think about herself and why she wants to do the things she does. She also has great self-insight, and she is very honest with herself. Being a stripper for a night felt like the natural culmination of the journey she and Robert had begun decades ago, with flirting and teasing. All along, Robert had wanted her to show herself to other men, and to have sex with them. The latter had only come quite recently, after years of waiting. Was it waiting, she wondered. Had she always meant to do it one day, before it was too late. She did not know. She had done what felt comfortable at the time. Saturday night at the strip club would be no different.