Entertainment for Seniors Pt. 02

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Entertainment for Seniors Part 2

Joe E Hartley

August 2022


Part 1 of this story received good comments and a few asked me to continue, the overall ratings put it into the hot range so, this is part two of a retired man’s approach to picking up women.

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.

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


Jack and Jane watched the rest of the movie and agreed to get together for another date the following week.

The next day Jack again went to the store. He was not actually looking for another hook-up since he found Jane, but was surprised by how many women seemed to go out of their way to talk with him. Normally he was the one to initiate a conversation, but today several women were actively flirting with him.

He definitely enjoyed the attention, but could not figure out why today was so different, that is until April commented to him that Jane had told her that he liked to walk at the park.

“My doctor is always telling me to get out and walk, but I’ve resisted. Do you think you might like to walk with me? I’m sure I’ll be slow and not able to go very far, but it might be fun,” she asked Jack.

He could have sworn he saw her wink at him when she said it might be fun.

Jack said he would be willing to walk at the park with her later on in the week since he over did it yesterday and took the phone number, she gave him. He promised to call when he was ready to walk with her.

Jack arrived back home, knowing that Jane had bragged about being with him yesterday. He wore a smile thinking that, based on the women today who were flirting with him, his dance card would soon be filled for the next several weeks at least. April was not one of the three women he had identified as a potential date, but she did like to show off her curves.

He put away his groceries and headed into the bedroom. He had just taken off his shirt and prepared to take off his pants when he looked up. He had left the drapes open and could see into his neighbor’s house. Peggy stood in her bedroom with her top off. He had just seen her at the store. They must have gotten home at about the same time and had a similar routine that is to get out of their street clothes as soon as possible and get comfortable. He found himself staring at his good-looking topless neighbor.

Peggy danced around her bedroom as she removed the clothes she wore to go out. She often wore little around house, normally just a thin Tee-shirt not really suitable to wear out and about, but it was comfortable. As she danced by her bedroom window, she thought she saw Jack from his bedroom starting at her. She continued her dance into her bathroom and peeked out to verify. Yes, it was Jack. They must have gotten home at the same time and both went in to change at the same time.

Living in a lower middle-class neighborhood meant that the houses were packed in tightly leaving little space between them.

She knew their bedroom windows faced each other, but this was the first time both windows had the drapes pulled. She felt a tingle knowing that he was staring at her, and decided to go back out and pretend she didn’t know he was watching. It had been a long time since anyone wanted to see her naked. She danced back out in front of the window and removed her pants. She now was naked except for her panties and she bent over facing away from the window as she looked for her Tee-shirt.

She took more time than normal to get dressed, but finally slipped on her Tee-shirt and walked out of the room as if she was unaware of her audience. She knew that she could see into his living room if his drapes were open. She opened hers to make sure he could see in if he so desired. She had given up teasing long ago, but didn’t know how to let him know she enjoyed him ogling her.

She poured herself a glass of wine and seated herself out in her back yard to enjoy the day a bit before she made lunch. She was not seated more than five minutes when she noticed Jack step out onto his back porch. He, like her, had removed his street clothes and now only wore his boxer shorts.

It was unusual for them to see each other since both tended to stay in the house, but today both of their bedroom drapes were open and they were in the bedroom at the same time and now both were out in their back yards. It had been over a month since Peggy had been in her back yard.

She saw her opportunity, “Hi neighbor,” she greeted. “I didn’t get a change to say hi at the store, you seemed to be very popular this morning.”

“Hi. It did seem that way, didn’t it. I’m not complaining, but you’ve had thought that I just won the lottery or something,” he answered.

“There is a rumor going around about you and everyone wants to see if it’s true,” she replied.

“What Tüyap escort bayan rumor is that?” he asked. “By the way, I’m sorry for looking though your bedroom window a little while ago. I normally don’t do that.”

“I thought I saw you peeping at me,” she giggled. “I’m long past the time when that would offend me, now-a-days It’s a compliment. I might just leave my drapes open all the time if you are looking for a show.”

“It was definitely a compliment; you are quite lovely. I can assure you that if your drapes are open, I’ll be looking,” he said trying to flirt.

“I’ll keep that in mind,” she replied.

“So, what is this rumor going around about me, that is causing everyone to want to talk to me today?” Jack asked.

“Apparently you and Jane had a date yesterday, and several other women want a shot at you too. Most of us can’t even remember what to do on a date,” she answered.

“Do you?” Jack teased.

“Ask me out and find out,” she cooed.

“I’m past the point where I ask a girl out for dinner and a movie. Jane indicated she liked to walk, but couldn’t find anyone to walk with, so I offered to walk around the park with her,” Jack clarified.

“The way I heard it, there was also a movie involved,” Peggy commented with a smirk.

“So, you are interested in the movie?” Jack intimated.

“Maybe,” she teased

Jack noted that the thin Tee-shirt she wore did nothing to hide her arousal. He also noted with interest that her eyes were focused low on his body. He knew that he was getting aroused and he thought she was too, but he wasn’t sure where to go with this information.

“Unfortunately, I don’t have any movies, nor do I have a means to play any. Do you? Or is the movie actually necessary? You could come on over and I can refill your wine glass and we can continue this conversation to see where it goes,” Jack said taking a chance.

“That is an option. It does shorten the date aspect and just cut to the chase, so to speak,” she countered.

“Is that a problem?” he asked.

“I’m not sure yet,” she said eyeing him closely. “Is that what you’ll be wearing?” she asked pointing more to his bulge than his boxers.

“Too much?” he asked.

Peggy laughed. “I’ll be right over.” She stepped back into her kitchen and set down her now empty wine glass. She toyed with the idea of removing her panties, but decided she’d allow Jack the honors.

The fence between the two properties had an adjoining gate, so she did not have to go to the front of her house. Jack had stepped inside, but left his back door open.

As soon as she walked in, he handed her a glass of wine.

“We have known each other for a couple of years now and it was just in the six months or so that we said more than hello to each other. Why do you think it took us so long to consider getting naked together?” she asked.

“Old conditioning takes a long time to overcome,” he offered as a reason.

“We’ve never even hugged,” she commented. “I have always enjoyed hugging, but don’t get a chance that often anymore.”

“I’d love to hug you, but based on how little each of us is wearing it won’t be a hug like you get from your grandchild,” Jack shared.

Peggy smiled as she set down her wine and opened her arms, “I should hope not, after all we are starting this date three-quarters of the way through a normal date and you got me back to your place and out of most of my clothes.”

Jack wrapped his arms around her with one hand placed low to squeeze her butt.

Peggy placed her hands on Jacks naked chest, “I love caressing a man’s chest,” she announced.

Jack moved his hand from her back to the front of her chest and onto one of her breasts. “And I love caressing a woman’s chest,” he announced.

Peggy smiled, enjoying the fondling she hadn’t experienced in many years. She lowered her head and began licking his nipples. She remembered from years past that some men really enjoyed having their nipples played with as much as most women did.

Jack appeared to be one of these men, to Peggy, as she watched him squirm under her stimulation. She was also reaching her limit of his stimulation of her. She dropped her hands to caress his erection and move them both to the next level.

Within just another minute, Peggy dropped to her knees in front of Jack. His budge that strained against his boxers less than an inch from her face. She licked her lips and lowered the fabric that hid his organ. His cock bounced up and rested on her lips. She looked up and smiled. She opened her mouth as she watched his reaction.

Jack looked down at the woman poised to take his cock into her mouth. He leaned forward resting his cock on her lower lip. He tried not to rush things any faster than they were already moving, but that effort was taking all of his resolve.

Peggy licked the tip of Jack’s cock and felt him again push forward. She took him into her mouth and relaxed her jaw.

Jack had just had sex the day Escort Tüyap before, so he felt more in control of his orgasm, but with Peggy sucking on him the way she was, he wasn’t certain he could last much longer. He pushed her back and helped her to her feet. Taking her hand, he guided her into his bedroom. He wasted little time stripping her and positioning her onto the bed.

Peggy felt in a daze as Jack took charge and suddenly found a tongue massaging an area of her body not touched by a male in several years. She remembered the warm wet sensations and felt the electricity flow throughout her body.

Peggy’s arousal had been building since she noticed Jack watching her strip out of her street clothes; she was now ready for what she remember normally happened after a very good date. Her body moved with him as if her hips were dancing with his tongue. He did not focus on her clitoris, but came back to it often. He, unlike so many men she had known, knew where her little pearl was and knew how to ring her bell.

She tighten every muscle in her body and quivered, before collapsing like a rag doll.

Jack moved away from her, pleased that he still remembered how to please a woman. He told her that he’d be right back before walking back out to his living room to retrieve their wine.

He walked back into the bedroom; Peggy had not gotten up yet, but her eyes were now open.

Jack handed her the glass of wine she’d left in the living room. “I assume you want to catch your breath before we continue,” he commented.

“It has been a long while since I felt anything like that, but yes I do want to continue,” she muttered. It was obvious that she hadn’t had this level of exertion in a long while.

Jack could relate; this was exactly how he felt yesterday after Jane drained him. “How about if we take a break for a little while? I’m in no rush, especially now that I know you’re interested in getting together naked,” he answered with a sly grin.

“You can look through my bedroom window whenever you want and if you want a closer view just come on over, and bring that magic tongue with you,” she flirted back. Her energy was quickly returning and she looked forward to round two.

“I’ll definitely take you up on that offer, but since neither of us are that young anymore, do you mind if we take it a bit slow?” He asked, but his cock was ready now.

“Your body isn’t listening to you. Your cock does not want to take it slow. You just gave me a very intense orgasm, how about if you allow me to return the favor?” she offered. ” I can take you in my mouth, but if you want to fuck, we’ll have to take it slow because it’s been a long time.”

Peggy stood up, set down her wine, and instructed Jack to take his position on the bed. She started to address his stiffened cock with her tongue. She, like Jane before, missed the taste of a male member. She licked his raised appendage top, bottom, and tip. She loved the taste of his pre-cum, it energized her for more. She engulfed as much of his cock into her mouth as she could, savoring the fullness. She caressed his balls with her hand as she stroked his cock with her mouth noticing that he enjoyed that sensation.

She gripped his cock and pulled it from her mouth so she could lick his balls and up his shaft to the tip, she retreated back down to his balls and repeated the cycle. After about half a dozen of these long licks, she felt him stiffen and quickly took all of him back into her mouth. She sucked hard until he took over the rhythm and started to pump her mouth franticly.

He unloaded his pent-up desire into her mouth while she sucked every drop from him.

Jack recovered after several minutes and Peggy handed him his wine, “That was fantastic,” she said.

“For me too,” Jack replied breathlessly.

“That is probably enough fort a first date, we want to leave something for date number two. I’ll head on home now, but now that you know I’m usually in the mood, don’t hesitate to call. By the way, I’ll be leaving my drapes open from now on,” Peggy said as she went to gather her clothes.

She made sure to give Jack’s, now soft, cock another deep kiss, before she left out the back door.

Jack needed to regain his strength, so he prepared a lunch for himself. After an hour of relaxing and getting bored, he remembered his encounter with April at the store this morning. She asked him to call her to schedule a walk at the park.

He picked up the phone and entered her number.

“Hello,” a woman answered

“Hi April. This is Jack. I thought I’d touch base with you about when you want to take that walk around the park,” he answered.

“I’m ready any time. How about tomorrow?” she asked.

“Tomorrow sounds good for me too. What time would you like to meet there?” he asked.

“Since this will be my first time there, why don’t you come on over here and pick me up around nine,” she responded.

They agreed on the plan and Jack made sure he had her address before ending Tüyap Escort the call. He considered himself the luckiest man on the planet right now. All that prep work he’s done over the last six months of getting to know these women and slowly introducing flirting was paying off. He’s already had sex with two women, and April seemed to want to be the third. She didn’t seem that athletic and she even commented that she hadn’t walked in a long while.

He knew her request for a walking partner was a ruse, but that was okay. He considered her cute and the only reason she hadn’t made it into his top three was the fact that he couldn’t think of anything to do with her, other than sex, that is. He was actually surprised that sex entered into the equation so soon with these women. He expected a few dates with Jane and a lot of flirting before he could get her into bed. And never expected anything to happen with Peggy, much less April. He hadn’t had sex with April yet, but that seemed to be just a detail.

The next morning, Jack, dressed in shorts and a Tee-shirt, rang the doorbell of the address April had given him. He heard her call out from inside the house, to come on in. He opened the door and stepped inside. About ten feet in front of him stood April, not dressed for walking. What she wore was geared more towards a different activity.

April appeared before him in a bra and panty set. The bra was more of a harness with a thin vertical strap barely covering her nipples. The panties were high waisted and likewise minuscule with a vertical strap trying to cover her intimate parts.

“I’m not quite ready yet, would you like a glass of wine before we go?” she asked.

“You look more than ready to me,” Jack responded, “Just not for walking out in public.”

“You like?” she asked taking a sexy pose, then turning around to show him that her panties were even more revealing from the back; one thin, barely visible, strap separated her cheeks and attached to the waistband of her lingerie.

“I like it a lot,” Jack answered as his shorts displayed the truth of his statement.

Alice walked into her kitchen slowly, putting a little extra sway in her stroll.

She returned with wine for both of them.

“You were never planning on a walk today, were you?” Jack asked as he took the glass of wine from the sexy nymph’s hand.

“That’s not exactly true, but the walk I had in mind was much shorter,” she said indicating her bedroom door. After I talked with Jane about your date with her, I thought it would be a welcomed opportunity to be with a real man, rather than my toys, if you’re in the mood.

“With you dressed like that, how could I not be in the mood?” Jack answered.

“I thought so,” April said looking directly at the budge in his shorts. “Why don’t you get more comfortable, that looks painful?”

“These shorts are becoming a bit restrictive,” he answered as he removed all of his clothes.

“Jane told me, that you are really good at oral, and I like that too, but would you mind if I just wanted to fuck? I’ve had nothing but replicas of cocks for so long, I just want to feel a real cock inside me,” she asked.

“I’m good with that, but you really don’t want a slam-bang-thank you, do you?” he replied.

April led him into her bedroom directing his gaze to the sight on top of her bed. About a dozen different vibrators and dildos decorated the top of her bed.

“I’m already primed for you,” she announced. “I’ve been preparing for our date since seven this morning, if you’re ready, so am I.”

Jack hadn’t expected this and it took him a minute to understand that April had already taking care of all the foreplay she required. He now had to come to grips with the realization that he needed a bit of foreplay too.

April seemed to notice Jack’s hesitancy and gripped his cock. She dropped to her knees and licked his cock. “This is just an appetizer to get you in the mood,” she announced.

It took very little to get Jack’s mind at the same level as his cock and he pulled her up to him. He stared to lick her nipples removing the bra like harness covering her. His hands went low, pushing the wannabe panties down.

April assisted and her panties were suddenly on the floor and she lay back on the bed surrounded by her sex toys and Jack positioning himself above her.

Jack entered her easily; her reaction was that of a person long denied this pleasure. She immediately turned into a wild woman eager to take as much as she could. She thrush her hips upward increasing the tempo of Jack’s strokes.

Jack had cum twice in two days, so he was not concerned about coming too fast, and April’s reaction indicated that she was close.

April stiffened and then with a sudden shudder, relaxed. Within less than a minute she changed positions. She got up onto her hands and knees allowing Jack to take her from the rear.

Jack had not used this sexual position in many years, but fond memories flooded his mind. Gripping her fleshy globes, he entered her and with a renewed enthusiasm, pumped into her, increasing the pace with each stroke. He heard the pants of pleasure from April in sync with his own.

The sudden intake of air followed by the very audible exhale signaled their mutual release. They both collapsed onto the bed.

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