Jesse's Long Wait

Chapter One

Jesse lay in bed waiting for Robert. It was Friday evening and the next morning they were going to a beach resort for a long weekend trip. She was wearing a dark pink short negligee and no panties. Her legs were a little apart and the bush of her pubes fully visible. Her pussy was beginning to get wet in anticipation. It took just a little longer than it used to, but she is seventy now, an age at which many couples have long left a sex life behind, but not Robert, who is a little older than his wife, and Jesse. Robert and Jesse have been married for more than forty years and Robert is the only man who Jesse had sex with over those four decades.

However, many, many other men had wanted to, and Jesse, encouraged and aided by Robert, had teased many men and let them think that they would have her, but none had. Robert loved to see his wife admired and desired by other men, and nothing turned Jesse on more than flirting and teasing, and occasionally flashing to other men. Robert would have liked Jesse to go further and have sex with the men she teased, but for all that she loved to flirt and tease and flash, Jesse had never wanted to go any further, and she was happy with Robert as her sole sex partner, and very much satisfied by him.

Jesse was thinking about the weekend. A beautiful beach resort to which they had been before and had fun. Nice lunches, nice evenings at the resort restaurant where the food was excellent; equally excellent wine in the restaurant with dinner, and in the pool side bar after dinner, long hot days on the beach: walking, sunbathing, a few photo sessions and, if Jesse caught the eye of anyone she liked the look of, and invariably she did, a little flirting and teasing, and because it was the beach, perhaps a little flashing too. These thoughts heightened her excitement and added to her sense of anticipation.

Finally, Robert came. He was naked and fresh from the shower. He stood beside the bed and looked down at his wife. How beautiful she is, he thought to himself. Jesse reached out and cupped his cock in her hand and closed her fingers around it and began slowly to wank him off. She felt him harden in her hand. He would have liked just to have stood there and let her continue, but he wanted to photograph her, so he stepped back and his cock slipped from her hand, He went to get his camera. A moment later, he was standing beside the bed again, camera in hand, ready to shoot. Robert photographed Jesse often and it excited them both and afterwards they always had a good session. Robert has pages on a couple of websites where he posts some of the erotic photographs he takes of Jesse. Her images get a lot of compliments from a lot of men, old, middle-aged and young.

Robert asked Jesse to sit up. She posed for some glamour shots in her negligee and, at Robert's request, ran her fingers through her long black hair and held her hair up high on her head. 'Now, baby, show me your pussy,' he told her. Jesse was kneeling on the bed, she leaned back and placed her hands over her forest of pubic hair, one hand each side of her not yet visible pussy lips. Robert took more shots. As he clicked away, he asked her about the men who would see her at the resort. 'There will be more beautiful women than me, and younger women,' she said.

'You are always the best', Robert replied. 'All the men will want you.' He saw in her eyes how much the thought of the picture he was painting thrilled her. Jesse loved to be looked at. She loved to feel the subtle yet devastating power that her sexiness and her good looks gave her. She loved the responses of the men she flirted with, and teased, and showed herself to. Robert went on, 'on the beach, they will see you in your bikini. You can go topless and all the men will admire your tits. In the restaurant and at the bar, you will wear a dress that is unbuttoned at the front one button too many, and just a little shorter than is entirely decent...'

As he teased and tempted her with these scenarios, which they had been in a hundred times, Jesse became more animated and let out a little squeal of pleasure. She leaned back further and as her body position altered, her pussy was pushed forward and her large dark lips became visible through her beautiful thick pubic hair. 'Open your pussy,' Robert said, a tone of command in his voice now. Jesse did as she was told, looked directly at her husband and smiled lasciviously. Her eyes shone and her lips wettened visibly. Jesse was enjoying herself and she felt like the camera was making love to her.

'Take off your negligee', Robert ordered. Slowly, she pulled the negligee up over her stomach, pausing as the hem reached her tits. Then, even more slowly, she pulled it over her tits until they fell out an bounced free. Jesse has incredible tits. Big but not stupidly big, the perfect size for her body, natural. Heavy looking but magnificently firm. There are women of forty who would kill to have tits as firm as Jesse's are at seventy.

Robert reached towards Jesse and fondled her left tit. Jesse reached for Robert's cock and stroked him again, faster this time. Robert began to breathe harder and he was about to put the camera down and enjoy the magnificent cock sucking he was about to receive. Jesse gave fantastic blow jobs. She could keep a man on the brink for hours, if that was where she wanted him to be, or she could suck his balls dry and have him shoot his all into her mouth in under a minute. 'Photograph me sucking your cock,' she said, 'and post the pictures on the web.' Robert put the eye piece of his camera to his eye and aimed the lens at his wife. Jesse met the gaze of the lens and held it. As she sucked her husband's cock, her head moving slowly and rhythmically back and forth on his shaft, she stared unblinking at the camera, making eye contact with it, and with everyone who would look at the photographs online.

Half of Robert wanted to continue as they were; him photographing his wife as she sucked his cock all the way to his climax, and getting images of Jesse taking cum shots. The other half of him wanted to fuck her, and it was this half that won.

Jesse lay back on the bed and Robert positioned himself between her legs, held his cock in his fist and guided it to her waiting cunt. Her pussy was very wet and she received him with ease. He thrust at her and she met his thrusts, raising her ass from the bed. Robert reached down and pushed a finger into her pussy alongside his cock. When his finger was sufficiently wet with her pussy juices, he pulled it out. As she thrust up to meet her and her ass lifted off the bed, her slipped his hand under her and found her anus with his wettened finger and pushed it inside. As he felt the soft velvet flesh inside her asshole caress and hug his finger, he heard Jesse gasp with pleasure. She loved it when he pushed his finger into her asshole when he was fucking her. 'Fuck me. Fuck me hard,' she cried. They were both close and Jesse came first, her orgasm made her shake and Robert felt the gush of hot juice flood out over his balls. In the next moment, Robert's cum shot into his wife's pussy, four good strong spurts.

They were tired now, and soon they would sleep. Neither went to the bathroom to wash. They lay together in the glow of their fuck, sticky and wet with each other. Robert could feel the stickiness of Jesse's juices on his cock, slowly drying in the warm late evening air. Jesse thought of Robert's spunk in her pussy. She slipped two fingers into herself and then after a minute of fingering, she pulled them out and raised her fingers to look at them. In the soft light from the bedside lamp, her fingers glistened with her juice and her husband's cum. She slipped her fingers into her mouth, tasting herself and her husband. They fell asleep, breathing softly in harmony with each other as they slept contentedly through the night.

The beach resort they were going to was about a three-hour drive from where they lived and they set off before eight. They arrived shortly after eleven, checked in and went to their room. It was at ground level and well-positioned close to the pool and the bar, with a little yard that served as a patio-balcony, and it had a large glass patio window. It was the same room they had stayed in on their previous visit. Robert had found this resort following a tip from an online friend, who was an admirer of the photographs of Jesse that Robert posted. Robert's friend told him that although this place was simply a beach resort and not a lifestyle resort or swingers' venue, there was a very discreet scene that the management were aware of, but turned a blind eye to, as long as it stayed very discreet and other guests did not see any evidence of it. And it worked, because those who wanted to participate in that scene, and wanted a change from the usual lifestyle resort scene, were experienced and knew how to play by the rules, because they did not want the resort to shut it down.

When Robert's online friend had spoken of the scene, he had meant full on swinging, not just the flirt and tease and flash that Jesse enjoyed. Robert's friend was a cuckold and liked to watch his wife with other men. Robert wanted this too; Jesse knew, but she has never yet wanted go that far. Robert, though, has not given up hope. By coincidence, or perhaps due to mysterious forces at work in the universe, Robert's online friend had told him about this resort a few days after Jesse had told him, one evening after a particularly hot wine-fuelled fuck, that the places where she most enjoyed playing her flirt and tease games were places where you really should not be doing that. It was the thrill of the forbidden that excited her; giving men to believe that she would give them what they were not supposed to have, and show them what they should not really see. Therefore, being at a place where you could play the games more discreetly, and where you had to be a little fearful of being caught, added greatly to her excitement.

They went to lifestyle resorts sometimes, and Jesse sometimes would go naked, or more often wear a bikini or go topless, and take off her bikini or her bikini panties at strategic moments, when she knew she had the attention of a man, or a few men, who she wanted to flash to. And she enjoyed it, but these were lifestyle resorts and it began with eye contact and progressed to teasing and flashing, and then to people hooking up and going to playrooms and the like, and she had never felt moved to go beyond flashing and teasing. Robert attributed her unwillingness to go with another man to shyness.

Jesse herself did not know why she had never done it. She had been tempted more than once, but always stepped back. Robert had asked her if she wanted to come to this place again, because the first time they had gone there was the closest she had ever got to going beyond just flirting and showing herself. They had a good time the first time and she said yes, she wanted to go again. She did not mention what they had done on their first visit, but Robert knew that she would have remembered. Robert had told her about the place, and the discreet scene and she had liked the idea of it.

Three Years Earlier

They had gone for a walk along the beach, some way from the main resort. They walked for an hour until they reached an area of the beach that had dunes that provided seclusion. Robert had correctly guessed that this was where the scene was played out, the exhibitionism and voyeurism games enjoyed, encounters had, and room numbers exchanged in setting up further night-time liaisons. They had turned and walked slowly into the dunes and just behind the first one, they had come upon a couple. They looked to be in their fifties, good looking people in good shape, and both naked. As Robert and Jesse approached, the women reached across her man's body and took his cock in her hand and began to masturbate him. Robert grinned conspiratorially at the man, and Jesse smiled to the woman, but they walked on by. Other couples is not their thing.

They made their way through the dunes where saw more couples, but none as bold as the first. They even came upon a lone woman, a rare thing in a place like that. She looked a well-preserved sixty or so and was probably on the look-out for a younger man with a taste from the mature lady. Jesse was not particularly focused on men of a particular age group. She would flirt with and tease any man who responded to her and whom she found attractive. She did more often though, choose men, in their forties and fifties, as her targets. They were coming towards the last of the dunes when they found a man alone. He smiled when he saw them and Jesse smiled back. 'Let's sit here,' she said to Robert, who nodded agreement. They had light, portable beach chairs with them and they set those up and sat on them. They sat facing the man. They had chosen a spot about twelve yards from him; not so close as to be intrusive, but close enough to show him that they were game. The man looked to be in his late forties or perhaps early fifties and he was a good looking chap. Jesse said as much to Robert, who was pleased to hear her say so.

Jesse took off her sarong before sitting in the beach chair and swung her foot up onto her knee. Her crotch, covered only by the gusset of her bikini panties, was pointing straight at the man, and lying on a towel on the sand as he was, he had a very good view. When she was sure she had the man's attention, Jesse began making her moves. She was subtle. There was always enough ambiguity about what she did, where her hands touched, that she might just unself-consciously be scratching an itch or brushing away an insect that had landed on her, or she might be teasing her watcher. She slipped a hand down between her legs and let it rest on her inner thigh, close to the gusset of her bikini panties.

The man watched. He did not stare in a way that objectified her and he did not leer. But he did not pretend that he was not looking. One hand on her inner thigh like that could mean something, or not, but when she reached down with her other hand and let it rest on her other inner thigh, there could be no ambiguity. The man knew that she knew what she was doing and she was enjoying being watched doing it. She left her hands like that for five minutes or so, until Robert took his camera from his bag. He took a few shots of her sitting on the chair and then asked her to stand. The man watched. Jesse sat back down on the beach chair and threw one leg over the arm of the chair. This was a provocative pose and the man's attention sharpened. He sat up.

Robert knew it was time to stroll over and talk to him. He would ask him if he would take a photograph of Jesse and Robert together. The man said yes, stood and took the camera and walked with Robert to where Jesse was waiting. Robert and Jesse stood together, each with their arm around the other's waist. The man took a few shots. Jesse asked him if it was ok with him if she took off her bikini top. He said 'please do', and she did. Her hands reached around to her back, so that she could unfasten the clip. She brought her hands back round to her breasts and cupped them, to take off her bikini top slowly.

Both Robert and the man watched intently as her boobs fell from her bikini top as she pulled it from them. The man said 'wow', and Jesse smiled and thanked him. Robert and Jesse stood side by side again and again put their arms around each other's waists and the man took more photographs of them. Robert asked the man if he would like to be photographed with Jesse. He said yes, and Robert took the camera and the man took Robert's place beside Jesse. Jesse put her arm around his waist, looked at him and smiled, and he put his arm around her waist. Robert took several shots and the man made no attempt to touch Jesse in more intimate places, and she made none to touch him, other than to hold his waist.

Jesse sat down and invited the man to come and sit with them. She remained topless and as she chatted with the man, who was sitting on the sand at her feet, she leaned forward to give him a good show of her boobs. He was emboldened and remarked that she had very firm breasts. 'For my age?' she asked, flirtatiously.

'Perhaps', he said, but I don't know your age.'

'A woman must have her secrets,' she said and smiled.

Robert was certain that the man was at the beach looking for a couple like him and Jesse, and that he was looking for more than a game of flirt and tease. And Jesse had done enough already to allow the man to think that he was going to be having sex with Jesse soon. He made his move. He said he was going to take off his swim shorts and jokingly said, 'don't worry, I'm not naked underneath.' He stood and pulled down his shorts. He was wearing tight-fitting speedos and clearly visible as it strained against the thin material was a large and very erect cock. The head was visible above the waistline of the speedos. Robert and Jesse feigned not to have noticed, and exchanged a knowing look. The man sat down and then lay back on the sand, displaying what he had to offer to Jess.

Like Robert, Jesse knew where they were heading, and she also knew that she had flirted and teased enough to have made this man believe that she would go all the way with him. She saw in Robert's eyes that he wanted her to. Half of her wanted to, but the other half was unsure. She decided to play for time. 'You said you don't know my age,' she said.

'No, I don't,' he replied.

'But you like older women.'

'Yes.'

Robert was almost certain now that she was going to invite the man to touch her and his cock was rock hard inside his shorts. She found the man very attractive. She loved to see his large cock fully erect and she loved knowing it was hard for her. She could feel her pussy juicing up, but the half that always said 'no' won out in the moment, and instead of inviting the man to fondle her tits or caress her fanny through her bikini panties, she said, 'you have a lovely big cock. Would you like to jack off while I watch you? She saw a momentary flash of disappointment in the man's eyes, but he said, yes, and pulled off his speedos and took his cock in his fist. He gazed at her intently as he slowly pulled his shaft up and down over his cock head. She looked over at Robert and she saw that he had pulled his shorts down to, and he was also masturbating.

Jesse was wildly excited at the spectacle of two men masturbating over her. She wanted to join them and masturbated herself. She felt confident now that the man understood her and knew that masturbating in front of each other was as far as they would go, so she took of her bikini panties to reveal her very hairy pussy. She placed her hands either side of her pussy and spread her lips wide open. 'Lovely,' said the man and jacked his cock more vigorously.

'This is what a sixty-seven year old pussy looks like,' she told him.

The man watched as Jesse slipped a finger into her pussy, pushing it all the way in. Then, she adjusted her sitting position to allow her other hand to reach under her leg. With the tip of her middle finger, she tickled the rosebud of her asshole, and as it slowly opened, she pushed her long middle finger up into her asshole. She moved her finger in and out of her pussy, but the one up inside her asshole she just moved a little and only softly. That was how she liked it. The man could hold back no more. Four, then a fifth generous spurt of cum shot from his cock and flew into the air and landed on the sand at Jesse's feet. Robert shot his load shortly afterwards. Both men watched as Jesse finished herself off. When she was done, she pulled her fingers from her pussy and her asshole and took each into her mouth, sucking long and hard on them, and especially the one that had been up her asshole.