Entertainment for Seniors

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Senior man finds an ideal pick-up place.
3.5k words
4.59
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Part 1 of the 3 part series

Updated 06/11/2023
Created 08/21/2022
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Entertainment for Seniors

Joe E Hartley

August 2022

Readers,

For most of us retired seniors, who don't stay up late or go out to bars and clubs, the grocery store can be an ideal pick-up place. There is no cover change and there are always plenty of women there.

This is the story of one man's approach to being older and single.

For those of you who do not like the idea of seniors, over 65, having sex, this story is not for you.

Joeehartley

Since Jack had retired, he found a way to keep himself entertained without spending too much money.

He lived in a lower middleclass neighborhood that had over half of the residents being retired and most lived alone, either divorced or widowed.

It took a few years but Jack found that the grocery store offered eye candy for men his age. At first it was not obvious, but there were good looking women who shopped most days; everyone needed an activity that was both cheap and outside the home. Walking around the neighborhood alone was problematic, (the older you are the chance of falling and causing serious damage is increased).

Jack learned that there were basically two types of women at the grocery store: those who wore multiple layers of clothes hiding the fact that they were female, and those who wore items that would show off their figure.

Wednesday was coupon day and the grocery store was always crowded, but with the overdressed women. Other days had a mix of the women Jack wanted to look at, and those he avoided.

He adjusted his shopping schedule from once a week to three times a week. Over the past several months he had spoken to several of the women he found attractive, He learned their names and a bit about them. He read their level of interest in him and kept notes on each of them. He hinted at the possibility of them getting together outside of the store without actually inviting any of them to get together. Their reactions to his teasing told him a lot and he made more notes.

After six months of his subtle flirting, a few of the women started to hint that it might be fun to spend time together away from the store. A couple had been wanting to walk around the neighborhood, but were afraid to walk alone and couldn't find any other women who also wanted to walk. Jack agreed that might be fun and that they should think about doing it, but no plans were made, (it was now a planted seed).

Jack had narrowed his selection down to three women, all attractive and willing to show off their curves. They were all fairly active, mostly exercising at home. They all were eager to get out more.

On Tuesday he saw Jane in the store and decided to make his move.

"Hi Jane. I was wondering if you were serious about wanting to go for a walk?" he asked

"I'd love to. Do you want to?" she responded.

It sounds like a great idea and would allow us to get out in the fresh air for a little while. Are you busy tomorrow morning around seven? He answered.

"That sounds perfect," she replied.

"Great, It's a date. I'll meet you at your house," Jack said with a wink.

"Ooh!" she exclaimed, "I haven't been on a date in years. What should I wear?" she teased back.

"Well, I'm not planning on taking you to the movies where we can make out in the back row. I was thinking we could either just walk around your neighborhood for about a half mile, or we can go to the park and try to avoid the joggers," he answered.

Jane ignored the making out comment, but Jack could tell the comment got her blood moving.

"The park sound fabulous," she answered once her breath caught up with her.

"Would you want to meet there or I can pick you up and drive us there?" he asked.

"Since this is our first date, it might be more appropriate if I meet you there," she answered with a smirk.

They agree on a place to meet and then both continued their shopping, but today they each wore a smile as they shopped.

Jack's plan was proceeding nicely. Going for a walk mandated fewer clothes than normal. He hadn't seen a woman in an exercise outfit in years. He arrived at the park ten minutes early and attempted to do the stretches he saw the people who did this often do. He gave up quickly afraid he might break something.

Jane showed up just a few minutes later dressed in a pair of shorts, and a Tee shirt. She was one of the women who had told Jack she exercised at home so she had exercise clothes.

"You look like you've done this before," Jack said to the limber Jane as she easily did the stretching Jack had given up trying to do.

"When I was younger, I walked at least ten miles every day," she shared.

"To tell you the truth, I haven't done any exercise in years. Maybe with your help I can get back into shape," he confessed. Jack was certain that women had a need to be helpful and liked to treat men a bit like children. He was giving her that opportunity.

"Glad to help. It would be good for me to get out into the fresh air and around trees again," she responded.

They walked the paved path around the park, past the playground that only had a few preschool aged children and their mothers there. They passed the vacant picnic tables and past the large grassy area. They only encountered a few joggers. The park would be much more active on the weekend, but on a Wednesday, this was it.

They chatted and laughed as each shared jokes and more details about their past and current lives. An hour later they were back at the parking lot and ready to head back home.

"That was fun," Jane said.

"Well, it wasn't a movie in a dark theater, but not a bad first date," Jack responded with a grin.

Jane laughed. "I'm not sure I'd like any of the movies playing now, but I do have Netflix at home, plus I have wine, if you are interested?" she offered.

"Now that sounds like a date," Jack answered.

"Well..." she hesitated, "how about we call it a couple of new friends watching a movie together?"

"We could," he said with a sly grin, "or we can call it Netflix and chill?"

Jane's face turned a deep shade of red, "we'll see," she answered. "Want to come over about 5 and we can find a movie to watch?"

"It's a date," Jack replied.

"Whatever you say," she said laughing, "see you then. Maybe we should exchange phone numbers, just in case something comes up."

"Sure, but you're not going to get cold feet, are you?" he answered.

"Honey, my feet have been cold for as long as I've been alive and if you're really lucky you may find that out first-hand latter on tonight," she stated with a sexy smile.

They ended their walk on that note and each headed home.

Jane enjoyed the flirting with Jack; it had been a long time since she flirted with a man. She enjoyed getting the chance to talk with him more in-depth than she had during their brief visits while grocery shopping. She thought of him as attractive before, but now he seemed both funny and exciting.

She, like many, had used the grocery store as a means of interacting with people in a safe and affordable way. There were a few men who also shopped and were willing to chat, but Jack was the first to ask her out on a pseudo-date.

She arrive home and went about her daily chores. She went about her normal activities with a spring in her step; she knew that her excitement was due to the possibility of actually having a real date after so many years. She allowed her fantasies free reign, knowing that the reality might not live up to the events playing out in her head, but they were fun nonetheless.

As the day progressed, she started to think more seriously about the quickly approaching evening and movie watching with Jack. She thought that the flirting this morning was harmless and not genuine; they were both old, after all.

She knew that Jack hadn't dated in several years and neither had she, but did that mean that had forgotten how. She now had to decide what she wanted. She wasn't certain if Jack was serious about his suggestive comments or not, for that matter, she wasn't sure if she was serious about hers either.

She had to decide what to wear when Jack came over, that could tell Jack a lot about her intentions once she figured out what her intentions were. She hadn't had to make decisions like this in too many years, but it was stimulating to think of his reactions to whatever she chose to wear.

After just a few minutes of indecision she eliminated the idea of wearing her thick bathrobe. She also nixed the idea of wearing her street clothes, she rarely wore them when she was home anyway. Her simple, yet modest, dress sent, what she thought might be, a message she wanted to send. It did not indicate she wanted to just hop into bed, but also that she hadn't totally rejected that idea either. It was a relaxed, yet not erotic, look, with just a hint of sexy.

She scanned what was available on Netflix to get an idea of what she thought he might like. She did not want a typical, violent, testosterone fueled movie, and she didn't want a typical estrogen dripping, soap opera type movie either, but she did want something that involved an interaction between two people that would lead the characters into the bedroom. That means romance, but it had to involve more lust, than undying love. It also had to have a fair amount of nudity; she knew that most men were very visual.

She verified that she had an ample supply of wine, then went to take her shower. At 4:30 she was freshly showered, dressed in a simple sleeveless shift that did not quite reach her knees, and sitting at her kitchen table in front of her laptop.

Her doorbell rang right at 5 o'clock. She appreciated his promptness and quickly checked herself, making sure she would not be exposing too much too soon, then went to the door.

"Hi Jack, you're right on time. Come on in. Would you like a glass of wine?" she welcomed.

"I was afraid I'd be too early. I haven't done this in a while, so I had to sit out in my car for the last ten minutes," he confessed.

"Sorry you had to do that. You could have come in. I've been ready and waiting for the last half hour. I guess we are both overly anxious. At least next time you'll know that you can ring my bell early if you want," Jane sudden recognized the dual meaning of the phrase 'ring my bell' and as her face started to reflect her awareness, she hoped that Jack hadn't caught on.

Jack's smile indicated that he also caught the double entendre but he chose not to comment. He was already nervous enough. "I'd love a glass of wine, Maybe, that will relax both of us," he answered.

He followed her to her kitchen table and took a seat. "You have a nice house," he said making small talk.

"Thanks," she replied as she set down a glass of wine in front of him. "It's nothing special, other than the fact that is does not have a mortgage payment," she answered.

"That is a big deal. I paid off mine a few years back too," he shared.

They chatted for a while about the houses in the area and what their respective homes were worth and why it would be stupid to sell now.

Jane asked, after a good half hour of relaxing small talk they both needed to ease the tension, "Do you have a movie in mind that you'd like to watch?"

"I really hadn't thought too much about the movie, but a lot about how I could be with you this evening without embarrassing myself," he shared.

Jane laughed, "That's what the wine is for. It's been a long time since either of us has had a real date, so lets just take off the expectations and try just to have fun this evening. I have picked out three movies that I'd like to see and they are not chick-flicks, but they are not macho guy flicks either. Would you like to pick one of those?"

"Are they comedies?" Jack asked.

"No, one is funny, but I wouldn't call it a comedy. I guess, in all honesty, I'd have to say they are romance, but I think you might like them," she answered turning her laptop for him to see the movies she had chosen and their descriptions.

Jack made his decision and Jane walked over to hook up her computer to the TV so she could stream the movie. Jack enjoyed the view of Jane in her casual wear and commented, "I like your dress. What do you call it? It's not a nightgown, or a house coat. It reminds me of a sun dress, but aren't those backless?"

Jane responded without turning around, she knew that she was bent over and giving Jack a good view of the back of her legs. Her dress was not short enough to show off her butt, but maybe if he liked this so much maybe she would get a shorter one, "it's called a shift and it's just a simple dress that is loose and comfortable."

"It looks really good on you," he replied.

Jane blushed a bit and hesitated about turning around too soon, but she couldn't stay as she was if she wanted her color to fade. "Thank you," she said, returning to the couch where Jack was already seated.

Jane had the remote and started the movie. They sat close, but not touching, so far. Hopefully that would change soon.

After a half hour into the movie. It was time for a bathroom break and another glass of wine. Jack found that he really enjoyed the movie and found it more erotic than had initially thought it would be. They took turns in the bathroom, then met back in the kitchen for a refill on their wine. They both commented about how much they were enjoying this movie. When they went back to the couch, they sat closer to each other; this time allowing their thighs to rest up against each other.

Jane turned on the movie and didn't mention the fact that she'd noticed the budge in Jack's pants, nor the fact that she had noticed him staring at her erect nipples pushing against the thin material of her shift. She was having a very good time and she thought Jack was too.

They continued to watch the movie and after a while Jack slipped his arm around Janes shoulders. She returned the gesture by snugging up against his chest. She lifted her feet off the floor and onto the couch in the classic snuggle pose. The hem of her skirt rose higher, although not quite high enough to be considered pornographic, but close. Soon she felt Jack's hand caressing her back and shoulder. The movie was showing some intimate scenes and that was encouraging both Jack and Jane to become more physical. Janes hand caressed Jacks chest.

She was not certain how far she wanted to go with this man, but she wanted him to be wearing fewer clothes. As soon as the characters had stared to remove their clothes, Jane knew she had to act, regardless of the consequences,

She stopped the movie again and turned to face Jack. "I think you would be more comfortable if you were wearing less," she blurted out. "It's very warm today and I don't have air conditioning. You can take of your shirt and pants too," Jack had taken off his shoes when they first started the movie.

"It is getting warm, but aren't you afraid we might go too far if we are half naked?" he asked. The budge in his pants told Jane he really wanted these pants off.

"We're both adults and I think we are both capable of making decisions. Don't tell you hadn't thought of what might happen if you came over for a Netflix and chill night?" She replied. She stood up giving Jack an unimpeded view of her stiffened nipples.

Jack stood, "I have, but I didn't want to appear too forward," he answered.

"Go for it," she answered.

Jack stood and took off his shirt. Jane just barely stopped herself from drooling. She'd always loved the sight of a naked male chest. Jack then lowered his jeans making known the sizable budge in his boxers. Jane took in a deep breath and emptied her wine glass.

"I think we need more wine," she announced, and walked into the kitchen.

Jane poured them each a glass of wine and after handing Jack back his glass, she stroked his now naked chest with her free hand. "Shall we watch the rest of the movie now?" she asked.

"The movie is starting to get pretty hot and I don't think that we are far behind," Jack commented.

"Do you want to stop?" Jane asked.

"Hell no," Jack responded and he used his free hand to caress Janes protruding nipples.

They found their way back onto the couch and snugged more intimately than before. Jane restarted the movie and as it started, she caressed jack's naked chest. She allowed her hands the freedom to travel low and Jack did not stop her.

The characters in the movie were now naked and in bed together. As is typical of R-rated movies only the woman's breasts are shown, but that was enough for Jack. His arousal grew and Jane's hand got closer.

As the heat on screen increased Jack felt Jane's lips on his chest. She kissed and licked the heated flesh working her way down until she had to shift her position. She hovered over him on her hands and knees, licking his stomach and down to the waist band of his boxers.

Her breasts were now within easy reach and he took advantage of their proximity to encase them in his hands. Jane's breathing increased and she stood in front of Jack. She had forgotten all about the movie and eyed his boxers. She wanted them gone. She reached out to him and griped the waist band of the offending clothing and slipped them down to the floor. She now had an erect cock within inches of her face and she leaned forward. She continued her kissing and licking routine, but this time on the head of Jack's cock instead of his chest.

She slowly slipped the head of his penis into her mouth and tongued its tip. She heard him moan. She took all of his organ into her mouth and stroked it with her lips up and down. She was ready for him to orgasm, since it had been such a long time since she had tasted essence of man, but he pulled her up and removed her shift.

He pulled down her panties and sat her back on the couch with her legs spread. It was his turn to drive her to the brink. It had been a while for him too, but the technique quickly came back to him and soon she was squirming her body back and forth.

He gripped her hips to hold her in place as she rode out her orgasm. He then released her and once she caught her breath said. "Okay, my turn now," and reversed positions with him.

She again had an erect and throbbing male member in her mouth. She used one hand to grip his ass, holding him firm, and her other hand gently scratched his balls. She took him deep then set a pace meant to cause him to lose control. She was not disappointed and soon her mouth was full of the elixir she craved.

She pulled away slowly and sat back on the couch. "I think that's as much as I can handle after so long. Wanna watch the rest of the movie?"

Readers,

Thank you for reading my work. Remember that I, like most writers on this site, receive no compensation for our work. The only reward I get is the votes and comments I get from you, the reader.

If you choose to contact me through e-mail or a comment, make sure to check your junk folder, because I always respond.

If you enjoy my work, please give it a 5-star rating.

joeehartley

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19 Comments
AnonymousAnonymous3 months ago

Very informative and entertaining!

AnonymousAnonymousover 1 year ago

Fantastic, loved the progression towards the movie night date and its eventual erotic coupling with the lady. Karl

vodiodo69vodiodo69over 1 year ago

I want to find this neighborhood! I want to get to Jack before he gets worn out. I have to find a different store!

AtrampboyAtrampboyover 1 year ago

Another winner Joe! Thanks!

Mesabi64Mesabi64over 1 year ago

If only! I don't know any single women over 60 who still have sex lives.

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