Grandfather Meets a Young Waitress

She turned at just the wrong time. She had the most wonderful backside and he had been admiring it, not for the first time, just as she turned. He was annoyed with himself. She was only a couple of feet away and she couldn't miss what he was looking at.

"Oh, I am so sorry. That was so rude of me, please forgive me. I meant you no harm."

Her slight surprised look turned to a lovely smile. At twenty years old, she didn't feel threatened by the man, who had to be as old as her grandfather.

"Consider yourself forgiven."

She wasn't quite sure why she added,

"Was there anything there that you liked the look of? I'll come and take your order in a minute."

He was so embarrassed, but appreciated that she had not got angry with her. Before she turned her attention back to the table she was serving, she gave him another smile, as if to encourage him to keep looking. She was wearing the uniform that all the female staff wore; a white blouse and a fitted short black skirt. It was smart and not intended to be provocative. She did seem to bend over a little more than she needed to, as she gathered the last of the glasses. He loved the way this tightened the skirt across her bottom, showing him a clear pantie line and a view well up her shapely legs. She was soon standing next to him.

He apologized again before ordering a coffee. She smiled kindly down at the old man, before asking.

"So did you?"

He didn't immediately realise what the question referred to. She gave him time before he remembered her question.

"In the old days, I would have been okay to answer that question honestly, but nowadays, I am told us males have to more careful. Am I allowed to say that you have a lovely figure, that even an old man like me can appreciate?"

"You most certainly can, but don't say it too loudly. I am Jill and will be your waitress today."

It had been a very short exchange, but it had lifted his spirit. He was delighted when it was the same girl who delivered his coffee, with a smile and a question,

"So, what does the rest of this wonderful day hold in store for you?"

"I shall probably go and sit in the park, and watch the world go by. I am meeting up with my two friends later, when we go down to the club for a pint. It is a highlight of the week, in my very boring, lonely life. Oh, I am sorry you don't need to hear me being all miserable. Anyway, you have brightened up my day by just giving me a smile, thank you. What does the rest of the day hold for you?"

"I shall probably go shopping and spend the money I haven't got. I am slightly at a loose end, as my boyfriend is not around. I am hoping to go out clubbing later, with my girlfriends. Anyway, if I keep chatting to you, I will get the sack. Good to meet you."

Jack was amazed at how he felt so much better, after a chat with Jill. The weather was warm and sunny and the park seemed a welcoming place. Jill had enjoyed the exchange too. She had felt sorry for the old man, but had also taken to him. He had looked sad, but by the time he paid the bill there was a happy glint in his eye, that she found strangely flattering and rather sweet. He reminded her a little bit of her grandfather, who had died six months earlier.

She finished her shift at lunchtime and decided to take the long way home, through the park. It was a lovely day to go for a walk, but she just wondered whether her choice was affected by the chance of meeting the old man again. When she spotted him sitting on a bench, she was shocked that she felt delighted. He didn't see her coming, until she said,

"Is there room on that bench for another bottom?"

She wasn't sure why she hadn't just asked whether she could join him, but was pleased when with a huge smile his reply was also slightly inappropriate.

"Only if it is a beautiful shapely as the one, I just saw in the café."

She matched his smile and sat close to him. They sat quietly looking across the park, until a young man and woman ran past in gym kit. Jack was very conscious of not following the woman with his eyes, due to Jill being next to him.

"How many out of ten for her arse then?"

He was tempted to pretend that he didn't know what she was asking, but realised it would have been stupid. Seeing his hesitation she said,

"I wish my boyfriend looked as good; well I actually mean as big as he did. He was really packing. I'll score him nine out of ten. I cannot really score him ten as I never really saw his face."

Jack was rather shocked by the comments. He got the meaning of what she had said, even if he had never heard the expression before.

"Well, I would have to score her backside eight out of ten, if we are playing that game."

"Core, you are very hard to please. Have there been any that you score higher since you sat here?"

Jack answered without really thinking, caught up in Jill's relaxed manner.

"No, the problem is the bar was set rather high earlier in the café."

Jill turned and smiled at Jack. He couldn't resist teasing the young woman who he had taken such a liking to.

"Did you see her as well, the girl serving at the other table?"

He managed to keep a straight face, for just long enough for her to wonder, if he was being serious. She pretended to punch him on the arm before replying.

"Well, if you think she has a better arse than me, I will just have to make sure she serves you your coffee tomorrow."

They sat watching the world go by, commenting on people as they passed. Not many scores were awarded and no one scored over seven. Jack asked her about her boyfriend. She told him that they had been together a year, what his work was and that he was away, as he was every month for a week. She asked him whether he was married and saw his eyes sadden as he said that his wife had died six months earlier.

"You must really miss her?"

She realised that it was a silly question, so quickly added,

"Do you get to socialise with many women? It must be very hard in your situation."

"Funny you should ask that. The answer is, that I get very little chance to, but I am faced by a very difficult dilemma right at the moment."

He hesitated for a moment and she asked him to carry on.

"My closest friend has made me an offer. Well, I think it comes from him. He has asked me whether I want to sleep with his wife. She is lovely and we have always got on really well, but my friendship with him is so important to me. My initial thought was, I was not prepared to risk the friendship, but then it hit me that I might never sleep with a woman again in my life. That is really scary."

Jill was fascinated to hear Jack's dilemma.

"You know I can't answer that question. He would have to be a special friend, to make that offer. Talking to my gran recently, I was shocked that before my grandfather died, they were having sex at least twice a week. Gran said that her orgasms were stronger than at almost any time before. I had no idea that at their age that they would be so sexually active. Maybe I should introduce you to her."

Jill wasn't sure what he was laughing at until he responded with,

"I can assure you, young lady, that sex doesn't stop, when you reach thirty. Even men like me, can get their little soldier to stand to attention. Although, I must admit that not having had sex with anyone since my wife died and nobody other than her for decades, it is for the first time in my life, a slightly scary thought."

"I had never really thought about what sex would be like as I got older. I am sure you will be fine, if you do sleep with your friend's wife. Do you have a strong erection when you masturbate?"

"My god, girls were never direct like that when I was your age."

"I am so sorry. I just feel so comfortable with you talking about sex. Let's play a little game. The running couple are coming past us again. I want you to watch her as she comes past and then fantasize about what you would like to do with her. I am going to fantasize about him, particularly about his cock. They are running circuits, we have until they come round again, then we have to tell each other our fantasy."

They sat not saying a word until the runners pass them again. It is Jack who broke the silence.

"She has the most amazing arse. I would have her on her knees and I would bury my face between those wonderful cheeks. I would lick her until she pleaded with me to fuck her. I would enter her fully from behind, but hold still, telling her if she wanted to fuck, she needed to do the work. I would watch as she pushes herself back on my big prick gradually increasing in pace and urgency. Her hand would find her clit and my balls just before she exploded in orgasm, tipping me over at the same time."

"Fuck that was hot. My fantasy is that he does have a huge cock, and after briefly enjoying a bit of 69ing he wants me on my knees. I position myself on the bed, so that we can use the mirror to watch each other, as he slowly stretches me with the biggest cock I have ever seen. He fucks me slowly, very gradually getting deeper and deeper. I try and find my clit with my fingers but his cock is pushing it into my pussy as he stretches the whole area. His cock is playing havoc with my clit, so I give up and find my nipples instead. It is many wonderful minutes, before his balls finally graze my pussy. As soon as this happens, he starts to fuck me more firmly. This is too much for me and my orgasm overwhelms me within seconds."

They sat in silence again almost as if recovering from their fantasies, before Jack whispered,

"That was exciting, almost too exciting. I was going to walk home, but that might prove unwise for a minute or two."

Jill laughed as she saw that he was trying to cover up the fact that he had an erection. Even when he repositioned it, it still remained very noticeable.

"In your fantasy you referred to her pushing back onto your big cock. It looks like that particular detail is not fantasy."

It was Jack's turn to laugh.

When Jack was ready, the two walked through the park to Jill's apartment. She considered inviting him in for a coffee but was worried he might misread the offer. Instead she gave him a big hug and said,

"I said I could not advice you, but I have changed my mind. Take your friend up on his offer, fuck the living daylights out of his wife and come and tell me all about it. I am sure you can find me at the café."

She was on her bed, naked, with her arse in the air, within a minute of closing the apartment door. She watched herself in the mirror as she masturbated fantasising about being fucked from behind. It shocked her, when she realised that it was not the runner in the park fucking her with his big prick, it was Jack. Her long violent orgasm was the best masturbatory one she could remember.

She thought about Jack a number of times, before he turned up at the café nearly two weeks later. She was shocked, that seeing this old man sitting there was enough to flood her mind with the fantasies they had shared. His smile, when he saw her, was warm and happy. She wanted to hug him, as she took his coffee order, but she knew not to do something so inappropriate. She couldn't resist asking him how things had been with his friend since they last met. He laughed and said,

"I will tell you all about it, when your shift finishes, if you want me to."

"I can't wait. See you in the park in an hour."

She was out of the café a minute after her shift finished. He was waiting on the same bench, as they had sat on previously.

"Well, don't keep a girl waiting, spill the beans. Did you, if you did, was it good?"

"I certainly did. Both my friend Bob and his wife Carol, were very excited when I said I wanted to take them up on their offer up. It was very clear that Carol was not being coerced into it, in any way. She had it all planned out. I wondered what he had told her about me as she seemed very keen to find out what I was packing, as you so delicately put it."

"Was Bob with you when you fucked Carol?"

"No it was one thing I was very firm on. If Carol and I were going to have sex, it would be just the two of us. I learned many years ago, that men can get very worried if they see their partners enjoying a big prick, too much. It was a good decision as Carol was, let's just say, very smitten."

"Tell me all about it. Don't spare me the detail."

"Well, a man shouldn't kiss and tell, but I suppose that given you will never meet Carol or Bob, there would be no harm. We got naked without any fuss. Carol has a lovely figure, smallish boobs with wonderful large, nearly black, nipples. She keeps herself very fit and, on the scale, we were using the other week, her bottom would score seven. That is hardly fair though, and I score her 9.5 when allowing for her age.

She was determined to take the whole of my cock into her mouth, as she said that she saw it as a challenge. I love licking a pussy and therefore we enjoyed pleasuring each other in this way for rather too long."

"Sorry, explain what you mean by "too long"."

He told the story without interruption as Jill listened totally transfixed.

"Well, I didn't intend to, but her orgasm caught me by surprise. I think it surprised her too. I was worried that this would bring things to a premature end, but it certainly didn't. Carol was far from finished. Her orgasm seemed to galvanise her, and she said she wanted to fuck me. Initially, I was disappointed that we would not do what I had hoped we would, but I shouldn't have been.

She got me to lie on my back and sat on top of me. She teased me by rubbing my erection along her wet pussy, trapping it against my stomach. It was surprisingly pleasant, particularly when she told me how wonderful the head of my cock felt, as it rubbed against her clit. When she finally sank down onto my cock she said the most wonderful compliments about my erection.

I expected her to simply ride me, but she had other ideas. When my balls finally felt her bottom, she settled all her weight on me and said that I was not to move unless she said so. She then placed my hands on her breasts and started to squeeze and release my cock with her pussy. Ridiculously, she actually asked me if I was alright. She laughed at me when I told just how alright I was.

She explained that, the only time she had ever had the pleasure of a really big cock, was when she lost her virginity. Her first lover was older than her and had been anxious not to hurt her. He had got her to ride him just as she was me. She had been uncomfortable with his size, that first time, but had ridden him until she had been exhausted from having numerous orgasms. She had always wanted to relive the experience, seeing herself as the innocent virgin.

We both laughed at this idea. She asked me for permission for her to play with her clit, so that I could concentrate on her nipples. She used her pussy to squeeze and release my cock with little or no movement up or down. I was delighted that this kept me fully erect. It was lovely, but it was not getting me close to orgasm myself. This was clearly her intension as after a few lovely minutes she very quietly said, 'I am about to have another orgasm. I would love it if you would stay erect and allow me just one more, before you fuck me however you wish.'

I loved watching her enjoy what I can only describe as the gentlest orgasm I have ever seen a woman have. Her eyes widened and her pussy tightened and relaxed eight or ten times, in quick succession, as she rubbed her clit. Her nipples felt like granite only softening after she thanked me.

After a minute recovering, she started to move her hips very gently. She asked me whether I wanted to change position. I would have liked to, but instead I asked her how things had finished the night she lost her virginity. She told me that her lover had allowed her a number or orgasms before gently taking hold of her hips, as she sat on top of him, and fucking her to one final climax.

I didn't think for a moment that, the now much older, Carol would orgasm again, but was delighted when she urged me on when I took hold of her hips. Within a minute she was more than matching my thrusts and it was her screaming out her orgasm that triggered mine."

Jill was stunned. She had seemed to live the story as he told it. At times it was her sitting on top of Jack, her pussy filled by his large cock. She was shocked, that now it was her sitting in the park, with a pussy soaking her panties. Jack looked like he was still deep in his memories, so deep that he had not noticed that his erection was very obvious to anyone within ten yards of him.

"Fuck, that was so exciting. How much has Carol told Bob about it? Are you going to be able to get together with Carol again? What did she say afterwards?"

"It was only last week. I have not heard from either of them. I am rather dreading meeting up with Bob for a drink tonight. Carol seemed very keen to meet up again, but she said she would have to, as she put it, "manage Bob"."

They agreed, that as soon as Jack's erection had eased, they would leave the park. Jack asked Jill what the rest of the day held for her. She surprised both of them when she replied,

"I will probably go home and masturbate. Your story has got me rather excited and I don't think I will be able to concentrate on anything much until that particular itch is scratched."

As soon as the words were out of her mouth, she realised that she should not have said it. She had just found talking very personally with Jack so easy. She had on this occasion gone way too far with her honesty. Jack didn't say anything immediately but she saw him trying to process it.

When they reached her apartment, she hesitated, and looked him in the eye, before she said,

"Would you like to come in for a coffee?"

He looked at her as if asking a question, before he laughed and said,

"I don't need another coffee, but when I was young, that was not what that question suggested. If it is an offer to help you scratch that itch, the answer is, I would be delighted."

She gave him a huge smile and he laughed slightly nervously.

"The meaning of an invite in for coffee is one thing that has remained unchanged for years. I wasn't envisaging much scratching going on, but I rather hoped you would be up to giving me the sort of experience Carol clearly enjoyed."

"My god, I wish girls had been so empowered when I was younger. Are you sure about this?"

"I am a little nervous about it, but my pussy is sending me very clear messages. Let's just take things slowly and see what happens."

By this time they were standing in her lounge. Jill moved towards Jack and held out her arms, offering a cuddle. Jack was pleased to be able just to hold the young girl, while he collected his thoughts. Jill had not intended the cuddle to be anything more than a friendly relaxing gesture, but was delighted when Jack's cock made its substantial presence felt. Jack sensed that his fast-expanding cock was clearly not a problem to Jill and reached round to take hold of the bottom, that he had so appreciated earlier.

"I was wrong, 9.5 doesn't do it justice. Before I declare my final score however, I think I need to get to know it much better."

He now reached under her skirt, and moved both of his hands inside her knickers, at the back. The action shocked Jill. Not because he did it, but because it aroused her way more than she expected. Sex with her boyfriend was good, but always started when they were both naked. There was something exploratory, unpredictable and kind of old fashioned about this. She buried her face into his chest not wanting to think about what it might be expressing, not wanting to see what he was thinking, just enjoying the strange thrill.

His hands simply caressed the cheeks not exploring further. The gentle caressing did pull her against his now erect cock. She wanted to grind her pussy against it, but decided to let him set the pace, as she felt almost detached and distant from what was happening. It felt wonderful and she didn't want to spoil the moment, or as it turned out the many moments.

Jack was delighted, as the Jill seemed to melt into his body. He couldn't quite believe what was happening, but decided to let things just play out. The skin on the cheeks of her bottom felt like a baby's. He would have happily stayed there, caressing them for hours. Instead he eased the panties down as far as he could, while they were standing as they were. It broke the spell that had seemed to hold them, and Jill pulled her head off his chest and looked up into his eyes. His eyes were always bright and lively, but now they were positively ablaze.

"Fuck, that was incredibly sexy, thank you. It feels like your cock agrees with me."

Jill moved away slightly and went to finish the job of removing her panties, that were still right at the top of her legs.

"Please my dear, let me finish taking your panties off. It would give me the greatest pleasure to discover the joys that they contain slowly, very slowly. If that is okay with you."

She didn't know exactly why, but it was far more than okay with her. She loved how Jack was clearly appreciating her young body, and wanted to offer him the chance to do exactly that. He moved her across to an arm chair and turned her so that she could hold on to each arm while staying standing. He took his time kneeling behind her, before moving her uniform skirt up out of the way without removing it. He kissed each exposed cheek once before starting to pull the panties down her legs. Again, Jill was stunned how this functional action could feel quite so erotic. Having removed the panties completely, he repeated the single kiss on each cheek before standing up. She was surprised when he offered his hands to her to allow her to stand up fully again.

"You look so fucking hot. Knowing that you have no panties on, while otherwise looking beautifully dressed, is so erotic. It will be exactly how I image you when you serve me coffee in the café."

Jill laughed at this and said,

"I want to be able to image you fucking me, next time I serve you in the café. Fuck me now, fuck me the waitress across the table, as if we are in the café now."

He led her to the table and she stretched across it with her arms as far apart as her legs. He eased the skirt up to her waist so that the view of her arse and pussy was unhindered. The view was perfect, flawless skin, shapely legs and arse, not a hair in sight to obscure the black crinkled skin of her anus or the red swollen lips of her pussy. He marvelled at how, even in its swollen excited state, her pussy looked impossibly small. He knew that he ought to lubricate himself before entering her, but she urged him on.

"Fuck me with your huge cock, in front of everyone in the café."

He did coat his cock with spit, before offering it up to her pussy. After a small adjustment to help the angle, the head of his cock stretched her as it lodged an inch or two inside her.

"My god that feels big."

"Are you okay, I don't want to hurt you."

"You are not hurting me; you are stretching me beautifully. I want you to stretch me where I have never been stretched, reach places never reached. Please fuck me as deeply and thoroughly as you have ever fucked anyone. Give me it all."

Her enthusiasm thrilled him, as he took hold of her hips and gently thrust into her, going gradually deeper each time. She commented on nearly every new deeper thrust, urging him on. When she reached through her legs she was amazed that he was nowhere near fully inside her. He was firm, but she was happy that it was not as rigid as it might have been, as she suspected that this was why it was so comfortable.

"That is amazing, every time you push into me it is as if your cock is stroking my clit. I have never felt so thoroughly fucked, and there is still more."

It took more than a minute before his balls brushed against her clit. She had begun to wonder whether she would be able to take all of him, but was determined that she was not going to back down. It was a relief when she realized that she had accommodated his whole wonderful cock. She felt him ease himself out of her before stroking the whole length back into her. It was like a piston pushing into her and it took her breath away.

Jill had always considered herself very fortunate. She aroused quickly, lubricated easily and rarely failed to orgasm strongly. She did however always require her clit to be played with. This was different to anything she had experienced before. Her excessive lubrication was never more appreciated and her arousal never in doubt. The position did not allow for either of them to use their fingers on her clit, but his prick was doing a great job caressing it every time the length of his thrust was sufficient.

"Please fuck me long and hard, it feels just perfect."

He lent back as he eased himself out of her, until only the head remained embedded. The view took his breath away. His cock was coated in her liquid arousal. Her anus was beautifully framed by her round firm cheeks with their perfect skin. He almost reluctantly pushed back into her, watching her anus respond as he did. He did not stop until her tight pussy had fully yielded and her clit was buried along with his cock. She had asked him to fuck her long and hard, he was happy to oblige with slow strokes.

"If you keep doing that, I am going to explode all over your beautiful cock. I would love it to last for ever, but fuck I can't take it, I'm going to cum, fuck me, fuck me, fuuuuuuucccckkkk, fuuuuuuck."

He didn't change anything, as he felt her pussy squeezing him rhythmically, as her violent orgasm hit her in wave after wave. It wasn't until he sensed that she was nearly finished that he increased the speed of his thrusting and allowed himself to cum strongly, announcing it as he did so.

He collapsed forward onto her nearly fully dressed body. His cock stayed lodged deep inside her for a couple of minutes, until he stood up and eased it out with a plop. She didn't move, until he had kissed both of her cheeks. When she did turn, she saw his cock for the first time and gasped. He had lost his erection, but both the girth and the length were still very impressive, as it hung heavily. It mesmerised her and she knelt in front of him and took it into her mouth, licking their mixed juices off its entire length. He smiled down at her and gently held her head, as if to support it.

Her attention felt lovely to Jack, but he knew that it would have no effect on his flaccid cock. The days of getting his huge cock erect for a second time were long gone. His inability to become erect, however did not signal the end things for the day. She was delighted when he said,

"My wife used to love me giving her a back massage. I would love to give you a massage, so that I can enjoy the whole of your beautiful young body. Would you like me to give you one?"

She ignored the easy innuendo and said she would love a massage. She loved the way he undressed her, kissing every new inch that he uncovered, until she was completely naked. The sight of her near perfect body delighted the older man, and he couldn't wait to start the massage. It only took him a minute to strip himself, naked. It was clear to her very quickly that this was not going to be a deep massage of her muscles, but an erotic caressing. This was confirmed when, after briefly massaging her back, his attention turned fully to her bottom and upper legs. His hands covered the whole area thoroughly, including her anus. The contacted varied from the lightest of touches, use of his nails to scratch gently, through to kneading the firm cheeks. He got close to her pussy but left it untouched.

Jill loved the feel of his hands and confirmed this as he asked,

"Are you alright my dear? My wife particularly enjoyed this, let me know whether you are okay with it."

Without waiting for an answer, he moistened his fingers with spit and found the dark crinkled skin of her anus with a single finger. He used just the pad to caress the very sensitive skin all around the dark opening. Jill had enjoyed limited anal play with boyfriends, but this had tended to be the insertion of a finger briefly at the point of orgasm. This was quite different. Her positive response to his question was delayed, but he accepted it as meaning she was happy with the anal play.

When she realised that his teasing of her anus was not just a brief chance occurrence she relaxed. She initially, consciously, stopped herself from pushing her hips up to encourage him to explore further. Slowly her need for his fingers to penetrate became too strong, and she pushed herself up against them. He allowed just the very tip of one finger to open her tight orifice, but even this was enough to cause her to groan in pleasure. He controlled the depth and speed of the penetration, even though her hips refused to stay still.

Jill wondered why she had never done this before. His single finger in her bottom felt almost as good as any cock had felt in her pussy. Jack could tell by the noises she was making and how her body was reacting that she was very aroused. He played her arousal, before easing his finger back so that she had to lift her hips to keep his finger buried. His other hand reached under her and found her clit. She panicked as her clit was very sensitive from her earlier orgasm.

She was just about to tell him it was too much, before she decided to try and ride it out. The sensations were extremely intense and she was far from sure she had made the right decision. He sensed her concern and widened the contact around her clit, and softened the direct contact with her clit. It was as if he could read her body perfectly. He fucked her anus with his single finger, assisted by her hips thrusting up to increase the penetration, while working her large very sensitive clit. She wasn't sure whether her clit would become too sensitive to carry on, or whether she would climax again. The pleasure, although slightly uncomfortable, was far too much for her to ask him to stop.

She didn't experience her usual gradual ascent to orgasm, but was instead hit hard by the first wave of indescribable pleasure. He loved how her body exploded into violent spasms, that meant he had to use all his strength to ensure he kept the stimulation to her arse and pussy going throughout her climax. Her arse demanded to be penetrated as deeply as his finger could reach, and her clit wasn't sure whether it was demanding to be released or rubbed harder. She had enjoyed many wonderful orgasms but this was one of the most violent. After the first violent spasms, that were finished within seconds, her body settled into more gentle waves of pleasure.

He reduced the stimulation as her body's reactions became less violent, until she said "thank you" in such a way that he knew it also meant please stop. He was amazed to discover, that while not fully erect, the excitement of her orgasm had led his cock to become far larger. Jill couldn't fail to notice this and asked whether he wanted more action. He thanked her, but confirmed that he was sure not even she could restore his erection as one orgasm was all he could manage in a day.

Well that was what he thought, until the next time they met and she offered him a little blue tablet.