Blind Date for Seniors Pt. 02

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I wrote Blind Date for Seniors a couple years ago and it received a high rating and lots of comments asking for more. So now that my medical treatments are done, at least for a while, I’ll see what I can do in way of a part 2.

BTW I edited Part 1 of this story to clean up a lot of the grammatic errors. I’m not sure if the edited version is active on Lit yet.

This story deals with seniors, over 65, having sex; if that is not your thing, then this story is not for you.


Ann reflected on the parts of her date with Jack that she hadn’t shared with her granddaughter. Jennifer would not understand that needs do not go away as you age, but the inhibitions can. There was no longer a line of men waiting to date her and playing the games she had been trained to play often did not produce the desired results.

She didn’t know what came over her to suggest they meet naked, maybe it was the wild woman thing that Jenifer used to describe her to Jack. She wanted to be that wild woman. She had spent too much of her life doing what was expected and never anything that could be considered wild. That is until yesterday.

Ann laid out her only piece of sexy lingerie thinking thoughts a wild woman would think. She found herself getting that tingling feeling, she had yesterday, all over again.

Jack relived his date with Ann yesterday. It had to be one for the record books. He had never met a woman like her before. He had sex on a first date before and even had a couple of one-night stands, but never in his wildest fantasies had he ever met his date for the first time naked and had sex with her before they even had a chance to say hello.

It was memorable, that much was certain. The more traditional date that followed was very good and even without the sex, and he wanted to see her again. He found her to be funny and intelligent. They explored all the topics most talk about over a week or two, all in one afternoon. He found that although they did not agree on everything, he found more in common with this woman than he had with any of the women he dated before, including his ex-wife.

He was not sure what to expect on his date this afternoon with her, but he was certain it would be interesting.

Jack called to verify that Ann was ready before he headed over. At the agreed upon time, he rang the doorbell.

Ann answered the door wearing her bathrobe. “Come on in Jack,” she greeted.

“Hi, Ann. Am I too early? Or did you have something planned that I’m unaware of?” Jack answered.

“Well, not exactly planned, but you’re not too early,” she stammered. “I’m not exactly sure how I want this relationship to go, but I can’t get yesterday out of my head.”

Jack stepped into Ann’s home, “Yesterday was a lot of fun, but I’m not sure if we can base a relationship solely on sex. Ninety percent on sex, sure, but not totally,” he replied with a laugh.

“Jennifer called me this morning and I told her that we were going to Cancun for a while to live the wild life. Needless to say, she was in shock. Oh, and by the way, if she mentions to you about your time in Africa, I told her that you had been there and had swum in the Nile,” Ann took a breath, before continuing. “Anyway, I ended up telling her that we had a boring date, like she expected us to have. I told her everything except the sex part, the walk, the dinner, the TV, and the fact that you left early. That seemed to make her happy.”

Ann looked at Jack as if that explained why she was only wearing a bathrobe and seeing his confusion continued. “That made me think about how freeing it was to meet you for the first time while we were both naked and having sex before we even said hello to each other. I felt alive and want that feeling again, but I know that we can’t repeat it.”

“Do you want us to be naked now?” Jack asked.

“I think the only reason it was so exciting yesterday, was because it was so unexpected and like nothing either of us have ever done before. We became the wild people Jennifer said we were,” Ann explained.

“Maybe we can find other ways to be wild. You said that yesterday was like nothing either of us had ever done before and I agree; I’m sure if we think about it, we can come up with a lot of things we have never done before. I like that it was sexual and there are a lot of sexual things I’ve never done because of one reason or another,” Jack offered.

“I like that too. I have always felt that anything sexual was off limits. My late husband was not all that interested in anything sexually exotic. He was only interested in getting his pleasure,” Ann confided.

“I never had a partner who wanted to explore either. Let’s make up our own sexual bucket list,” Jack agreed.

“Do you like lingerie?” Ann asked.

“You mean to wear, or to see you Escort Haramidere in?” He responded with a slight laugh.

“I meant would you like to see me wearing lingerie, but if you want to add you wearing lingerie to the bucket list, I won’t complain,” she replied with a grin. “I might like seeing you with some skin exposed,” she added running her hand over his chest.

“Let’s start with you wearing some. Do you have any?” Jack asked.

“I do. I bought one outfit years ago and wore it once, but my late husband ridiculed me for buying it and I never wore it again,” she confessed.

“Do you have it on under that robe?” Jack asked.

“No, but it will only take a minute for me to put it on,” she responded with anticipation.

“I’ll wait here, but not patiently,” Jack answered.

Ann hurried into her bedroom, removing her robe on the way, Jack got a nice view of the back of her naked body as she disappeared into the room.

She returned less than a minute later wearing a pair of black bikini-cut panties and an open top that hung just above her hips and was tied together with a black shinny ribbon between her breasts. The top was simi-sheer, showing off her breasts. This outfit displayed a lot of flesh.

Jack’s response was everything Ann had hoped for. She noticed the lustful look in his eyes and the open mouth. All he said was “Wow!” but that was enough.

When Jack regained his ability to speak, he said, “That is hot. It really shows off your sexy body.” He reached over to caress her nipples though the slightly cloudy material. He felt her nipples harden under his fingers while at the same time felt his pants growing tighter.

“We may have to get you some more lingerie. It makes you look enticing. I want to add that to our sexual bucket list,” Jack offered.

“Sounds good to me. I’m not sure where to get the really sexy clothing anymore. The store I bought this at is now out of business,” Ann replied.

“I think there are a lot of on-line stores. We could shop together and have fun when you try them on. Let’s see what we can find and what we like,” Jack offered.

“Would you like it if there were more skin showing?” she asked exposing one breast.

“I like that a lot. I forgot what we had planned for the day, but we can fire up your computer and see what we can find in way of sexy clothes for you,” Jack suggested.

“Would you like it if I was not wearing any underwear?” She asked turning around to show off her butt.

“Very much,” Jack acknowledged.

“I’m not sure why, but I think you like looking at my butt,” she stated.

“You have a very lovely butt,” he answered as he stroked her panty covered ass.

Ann led Jack into the room she had turned into an office of sorts. That’s where she kept her computer, printer, and other office type supplies. She pulled up a second chair for him and turned on her computer. She stared a google search for lingerie and was surprised at the variety she found.

Jack, seated next to her, stroked her back and shoulder as she navigated her search.

They quickly bypassed the bra and pantie sections and started looking at teddies and baby dolls, much like she currently wore. Some were see-through, but most were not. Jack suggested she modify her search to Sexy Lingerie. Once she did that, almost all she found was either see-through or had the breasts completed uncovered.

Jack modified his strokes as well. He now played with her nipples as he saw the bared breasted models.

She focused on the sets with at least the nipples exposed and a throng remembering Jacks comment about seeing more flesh and how that made her feel. The images on her google search blocked out the model’s nipples and any part of the genitals that the outfit might expose, but they did give a general idea of these items exposed.

“What do you think of these?” Ann asked Jack. “Do you think I will look as good as these models if I wore any of these?”

“Better,” he responded.

She smiled and pointed out a few she liked and asked Jack’s opinion. She placed an order for two items she and Jack booth liked. “Should I get more, or wait for another day?” she asked.

“Have you ever thought of maybe getting a little kinky?” jack asked.

Ann perked up and stared at him with a sexy grin. “What did you have in mind?” she asked as Jack started to pinch her nipples.

“Change your search to Sexy Leather Lingerie,” he directed.

She was not expecting the new images. They were much more revealing and some of the models, held whips.

She focused on one model wearing a shelf bra, a garter belt with no panties and holding a whip like item. “What’s that?” she asked Jack.

“That is called a flogger and it’s used to spank,” he explained.

“I like this outfit. İkitelli escort Does the flogger come with it?” She asked and after a quick check found that the answer was no.

She ordered the outfit and changed her search to Floggers. She found one that Jack said would be fine to experiment with. She ordered that too.

She turned towards Jack. “I think that’s enough for me to start. Should we look for something for you?”

“We could,” he agreed.

She modified her search and quickly found male models wearing a collection of straps and a cod piece.

She was about to order one of them when she noticed a his and her set of straps and the male cod piece was open to allow the penis to be uncovered. She ordered the set. Both the male and the female items were crotchless. She liked that.

Ann shut down her computer and turned towards Jack. “Now I can hardly wait to get these new sexy clothes. It was fun shopping with you, but now all I can think of is sex.”

“Nothing wrong with that.” Jack replied as he again started caressing her breasts.

“I thought we agreed that we would not base our entire relationship on sex,” Ann answered, enjoying the attentions Jack was paying to her breasts.

“It’s not all about sex, we just did some online shopping,” he retorted.

“That’s true, and I can tell that you actually like me in lingerie,” she answered wrapping her arms around him. “Maybe we can talk about what we want to put in our sexy bucket list, now that we started it.”

“That’s a great idea. You already mentioned that you noticed that I like looking at your butt, and that is very true. I would also like to spank you,” Jack confirmed.

“Spanking? Really? No one has ever spanked me before, but I have heard that a lot of women like it. I did say I wanted to experience things. Would you use the flogger we just bought?” she asked.

“I could if you want, or I could just use my bare hand. We’d have to start gentle to see if you like it and how hard,” Jack answered. He noticed how aroused Ann got as he spoke about spanking her.

“I did like it when you pinched my nipples earlier. I want that in the sexual bucket too,” she added.

“I think it goes without saying that we both enjoy oral and I’m getting so turned on right now I can only think of licking you all over,” Jack confessed.

That announcement spurred Ann into action. She grabbed Jack’s hand a led him into her bedroom. She promptly removed her lingerie and stood naked in front of a fully dressed and yet highly aroused Jack. It took him only a minute to remove all of his clothing.

Ann crawled onto the bed as Jack landed a soft smack on her exposed derriere. She paused for a moment and received another.

“Ooh,” she said, “I think I like that.”

“You have a gorgeous ass and later I want to explore it,” Jack commented.

Ann rolled over, “Aw,” she sighed her disappointment that she’d have to wait until later.

Jack leaned over and caressed one of her breasts, then pinched her nipple while taking the other into his mouth. Her reaction told him she liked her nipple being pinched. He pulled away to test this new insight. He pinched both of her nipples and watched as she arched her back and moaned her pleasure. He increased the pressure slightly and she let out sounds similar to her pre-orgasmic sounds. He would remember this and went back to licking her torso.

He licked her stomach and across her hips. He progressed down her legs and worked his way back up her inner thigh. She spread her legs to give him greater access to her sweet spot.

Like yesterday he buried his face between her thighs licking high and low. She was extremely responsive and soon started to buck and grind her pelvis into his face. As her orgasm overtook her, he slowed down, but continued to lick up and down her creases.

She recovered enough to speak and asked, “Do you think I could be on top?”

“By all means,” Jack answered, “that position gives you the most control.”

He helped her into the classic woman on top 69 position above him and as soon as she lowered herself onto his waiting tongue set to work. He now had limited control of where his tongue explored, but she made sure he licked all the areas she wanted. She sat up straight forcing his tongue inside of her and began to gently bounce on top of him.

She seemed to him as if this was the first time she was ever on top and was enjoying the sensation. After her second orgasm in this position and as she rested. Jack asked, “Have you ever tried it facing the other way?”

“No,” she replied. “Can we try it?”

Together they slowly positioned her into the proper position and she explored the new sensation this new face sitting position offered. She again found herself in almost total control and Çapa escort bayan took advantage of that. She rubbed her sensitive regions back and forth across his eager tongue.

She came easier in this position and was soon exhausted. She fell over onto the bed away from him mumbling something about that being the best she ever experienced.

Jack got up, stroked her ass and gave her a quick smack, “I’ll get us some wine. I’ll be right back, don’t go anywhere,” he said giving her ass another quick smack.

He heard her moan something about more, before he left the room,

Jack returned with two glasses of wine to find Ann sitting up on the side of the bed. She took her wine then commented, “Well, at least this time we waited a bit before jumping into bed.”

Jack laughed, “It does seem that we start our dates with sex, doesn’t it?”

“It does, and regardless of what we said before, I don’t see a problem with that,” Ann reacted. “But now we have to decide what we want to do now. Just so you’ll know, I told Jennifer that we might go to a museum. You did say you were an artist, didn’t you?”

“I did, but that was a while back and I only sold my art on ebay and never for what it cost me to produce,” he shared. “I think the most I ever made on a piece was $25 and that’s why I quit trying to sell any. Each piece cost me over $40 in materials alone.”

“I’d love to see some of your art,” she replied.

“If you like, we can get dressed and stop off at my place after we get back from the museum,” he offered.

“I know Jennifer will ask about our date at the museum, so we should go, but I really do want to see some of your art,” Ann acknowledged.

They finished their wine as they reluctantly put on some clothes that would be acceptable to wear in public. There was a museum not too far away, that they both knew of, but didn’t visit very often.

They arrived and noted that it was not too busy. This was no surprise to either of them, since they were both retired, they tended to do things when most people were at work. They paid their entrance fee and started their self-directed tour.

Two hour later they had had all they could take of this; they did have a pleasant experience discussing the displays with each other, but there is only so much education they could handle at one time.

Jack drove them to his house to show Ann some of his art as he had promised. He didn’t plan on spending too much time there since it had been several hours since either of the had eaten.

Ann was impressed with the pastel drawing/paintings Jack showed her. Most were figurative pieces of nude models, both male and female, but he also had a fair collection of still life pieces.

“You have quite a few drawings and you are very good,” she commented after seeing a couple dozen pieces of his work.

“It was a hobby of mine for about seven years and I went to open workshops two or three times a week. I enjoyed it a lot, but when the workshops closed, I couldn’t find anywhere to practice, so I just allowed my hobby to lapse,” he shared.

“I’ll pose for you,” Ann offered.

“When you are naked, I can’t focus on anything but sex, so that won’t work,” he replied with a grin.

Ann joined him in the sexy grin, and changed the subject. “Wanna get something to eat? I’m sure you’re as hungry as I am,” she asked.

“Good idea. There are a couple of casual dining places close by, or we can go back for pasta at the same place we ate at yesterday,” Jack offered.

They settled on Mexican food and had an enjoyable meal before ending their second day together.

The next morning Jennifer again phoned her grandmother to ask how her date went. “Hi Grandma. Did you go to the museum with Jack yesterday?”

“Yes, we did and have a very enjoyable time. He even took me back to his place to show me some of his art, then had a lovely dinner, before calling it a day,” Ann shared, taking care not to mention the online shopping for sexy lingerie or the fabulous sex.

“That sounds like fun. Do you think you’ll sleep with him?” Jennifer asked.

“Jennifer! Do I ask you about your sex life? Who I choose to sleep with is no concern of yours,” Ann chastised her granddaughter.

“Sorry grandma. It just seems that you two are hitting it off and I hate that you are all alone,” she apologized.

“Jack and I are having fun together and that’s all you need to know,” she answered.

They chatted for another half hour with Jennifer trying to get information out of her grandmother. Ann loved talking with Jennifer, but she was not about to admit anything about her kinky relationship with Jack, or what she planned to do with him the next time they got together.


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