1 – A Chance Encounter

Just for a change of scenery, Alex would sometimes turn right out of his street and walk up the hill past the cemetery on his morning walks. This was an alternate path to the beach which he’d take if he wanted a slightly shorter walk, or just if the mood struck him to do so.

The cemetery was well populated along the main street, but turning west around its corner, there was a large as-yet unused area where there was a road leading to the other areas and stairs taking you up to a raised area where all plots were ‘in use’. Being on the same hill Alex walked on, the cemetery had several levels allowing for various uses of the uneven land, but he always thought it strange that the top area was raised as much as five feet higher than street level, a retaining wall around three sides keeping the ground in place.

It was this area that caught his attention this particular morning as he noticed a woman sitting on a marble bench presumably visiting a loved one. He was on his way home at this point, so she was facing him as he walked by, and they briefly caught each other’s attention making eye contact. He had a sudden feeling that he knew the face, but at the same time, it wasn’t familiar, just a face he’d seen somewhere before. This thought may have been sparked by her seemingly having the same reaction to his, although she looked away quickly as though she didn’t want to see. Dismissing it as likely a faulty memory, Alex continued home to prepare for his day’s work at home.

In his late fifties now, Alex loved that he’d been able to keep up this practice of daily walks and appreciated the ability to work from home giving him that flexibility in the morning. He never did like the office politics that seemed to intensify with a physical presence and managed to avoid it altogether by keeping his distance. It didn’t provide the same kind of opportunities for meeting new female companions but given his age and especially his desire for mates with an interest in giving each other sore, red bottoms, that wasn’t happening anyway.

For this reason, an appropriately named dating site, ‘Spanking Seniors!’ grabbed his attention. Presumably, a place where like-minded naughty ‘girls’ and ‘boys’ of advanced age could find each other without all the subterfuge involved in finding such mates. As is typical of such sites, one created a profile description that hopefully attracted others, and uploaded a photo so you’re not a faceless entity. The unusual part of this site was a list of ‘interests’ that one could check off that apart from the obvious ‘spanking’ included the usual relationship types like long-term, hookups, phone/chats as well as darker stuff like Dom/sub, bondage, pegging and the like.

Alex had looked over the site as much as a non-member could and decided to sign up for the free version. However, he quickly realized the limitations of free membership, primarily that you could not reply to emails sent from interested members, so he paid an annual fee and could now reply to the surprising number of ‘likes’ and messages he received. It didn’t take long to realize the shortcomings of the way this site worked.

First, very few people he ‘connected’ with were paying members, so they now couldn’t reply to his messages. Second, a non-member could ‘say hello’ with a system-generated message to someone you liked, but again they couldn’t reply should you respond, and the messages were a poor attempt at sexy come-ons, that the sender didn’t even see, again unless you were a paying member. Finally, although the name would seem to imply older members who were into unusual sexual practices, there were many non-seniors and a surprising number of young people using it as just another dating site with no interest in any of the fun activities and often looking for their lifetime partner. In fact, it was an exceedingly small percentage of members who were interested in spanking at all, regardless of their age.

That’s not to say it was a complete waste and Alex did manage to find a few people with whom he tried to communicate, one of which was a paying member. An attractive woman with the intriguing screen name of ‘URGonnaGetIt’ seemed promising as one who wanted only to give, not get spankings. When he’d come across women who wanted the dominant role, they usually wanted more of a full domination experience including the darker side of BDSM, so someone who was just into spanking was a real find in his mind.

She was sixty-one years old (about four years older), but her main photo showed a much younger-looking face that was pretty and friendly. Other photos showed a sterner side, including one with her pointing a hairbrush at the camera, the threat implied being obvious. She lived in the city of St. Pete which bordered the town Alex lived in and her profile was simple with ‘hookups’ and ‘spanking’ listed as interests and a description that seemed perfectly suited to him:

Single senior woman misses her husband/naughty boy who needed frequent spankings to keep him in line. Are you a naughty boy? Do you need to have your pants taken down for a good, hard spanking across my knee? I’d love to spank your bottom, but I do NOT switch! The only red bottom in our relationship will be yours, and I promise you … it will be very red!

Alex found himself getting hard as he reread the description several times, so he fired off a message:

Loved your description and we live in the same county! I can be very naughty at times, but it seems like you’d know exactly how to deal with me!? Want to chat?

He clicked ‘send’ with a bit of nervousness. He’d never done this before on any dating site, let alone one that claimed to have a focused on his favorite pastime. Though he couldn’t imagine how someone would misuse his information, his secrets, he was still uneasy about sharing something he’d been very careful about revealing.

Hoping for a quick reply he checked the site often and while he knew people often went days without looking at such sites, he still felt like he was being rejected. He’d gotten to the point where he was only checking every other day or so when finally, there was a quite simple reply, ‘Yes, I would’. He wrote back asking to arrange a time when they could send messages in real-time to make it more interesting and waited for a reply.

Since she’d shown some interest, he expected a quicker response than last time but was disappointed again when more than a week went by. He sent another message saying he was looking forward to hearing how she’d ‘deal with him’. Again, no response so he sent another message, hoping to entice her, telling her how much he’d love to have a strong woman put him across her knee for a long, hard spanking.

Weeks went by with no response, so he gave up on her and the website as he only found women who wanted to truly abuse him or to be abused. He never found another profile that so matched his desires even when he opened his search up to anywhere in the state.

Amanda sat on the marble bench in front of her husband’s grave as she often did but with decreasing regularity of late. She felt she was mostly over her grief, but still found it comforting to sit and have these one-sided ‘conversations’ with him. Sometimes it was small talk, or remembrances of special days, but lately missing a very specific aspect of their life and finding it difficult to move on, she sought his approval.

A mildly spiritual woman, Amanda imagined she could hear or sense an answer to the questions she’d pose to him. She knew in her heart he’d want her to be happy and find someone with whom she could enjoy what she was missing so much now, but she needed something more in order to feel right about pursuing this interest.

“Oh, Dan we were so good together!” she said aloud, “Whenever you needed to be my naughty boy, you’d find a way to get me to take you over my knee for the spankings we both loved so much. Do you remember how horny I’d get when I was the one who initiated a spanking with you? I’m getting that feeling a lot lately and I may have found someone who needs and wants to be disciplined, but I’m having trouble taking the decisive step. Do you think I should do it, Dan? Would you be okay with it?”

Imagine her shock when at this instant, the very person she was talking about walked by the cemetery and looked right at her! She looked away quickly, but looked back when he continued walking by and was nearly certain it was ‘LuvSpnkng’. She looked at the gravestone as though he’d given her the answer but was truly shaken by the extraordinary coincidence of his appearing at that exact moment. She hadn’t replied to his messages on the ‘Spanking Seniors’ site because she was still torn about whether to take that step. Was this the answer she’d been looking for?

She went home and looked the person up in “Spanking Seniors’ she’d found and started a half-hearted dialog with. She too found the site more frustrating than helpful or informative and didn’t want to lose what was the only connection that seemed to fit with her needs so well. She’d get mildly aroused, sometimes more than mildly when she’d read his description:

I’m a single, unattached, straight man looking for a woman who knows how to handle my frequent naughtiness, the only cure for which I’ve found is a trip across the knee of a willing and capable woman for a well-deserved spanking! I can be most appreciative when I’ve been dealt with properly, the result being my very sore, red bottom and your lust dealt with properly as well. Message me if you’re now imagining my bare bottom in your lap awaiting your punishing hand! I am also quite adept at taking you over my knee for some harsh discipline should the need arise, but honestly, I prefer to be the one unable to sit on a freshly punished bottom.

Like most profiles it went on to list likes and dislikes; music, movies, walks on the beach (who doesn’t?), etc. but reading this first paragraph, as she had many times always started that familiar stirring in her crotch and usually dampening panties as well. She decided to reply, weeks late though it was, with ‘Was that you walking by the cemetery this morning?’ She was certain it was given how often she’d looked at his picture while reading his nearly perfect profile, the only imperfection being the suggestion that she might like to get spanked as well, which she most certainly did not!

The message sent, she now waited for his response and now felt the same frustration he had when she’d delayed so.

Alex had a separate email address he used for the kind of messages he didn’t want someone stumbling across, which he didn’t check often unless he was expecting something. He’d given up on ‘URGonnaGetIt’ weeks ago and there wasn’t anything else he was waiting for at that address. It was only his need for a tidy mailbox that made him look and find she’d finally responded several days ago.

Looking up her profile again he suddenly realized she was the woman in the cemetery. That’s where he’d seen her before, her profile picture on this crazy dating site. He’d only thought about it a few times since, trying to place her face but lacking success, had given up. He typed a harmless response ‘Yes it was! Would you like to get together for a cup of tea?’ and clicked ‘send’.

This time he thought he ought to get a quick response, or at least not wait weeks for one, but a few days went by, and again he was frustrated. He wasn’t going to chase her again like he had before, but rereading her profile he thought that being a widow, perhaps this was hard for her to take these steps and just needed time to sort out her feelings and decided to be a bit more patient.

It was a gorgeous late winter day with a perfect sky and cool temperatures when he started today’s walk. Although going past the cemetery was his least common path, he was doing so more frequently now hoping to see her again, although not sure what he’d do if he did. He’d just turned the corner to the side street when he saw her sitting there again. Having a sudden idea of how to move this along gently, he turned quickly and headed back home before she could see him again. He only hoped she’d still be there when he returned.

As he approached the cemetery in his car from the back entrance, he was excited to see her still sitting on the bench. There was a park bench under a tree directly across the cemetery road and from the stairs leading down from that raised area. He spread the beach blanket over the weathered wood of the bench and placed the open box of donuts and cups of coffee and tea he’d hastily run out to get on the bench next to him. Now he waited. Fortunately, it wasn’t long.

 After another spiritual conversation with Dan, she’d decided to move forward and with a combination of arousal and nerves she headed home to respond to his message; and she wouldn’t delay responses any longer. Every step had her increasingly excited to the point of wanting to run home and get the ball rolling.

Running wasn’t something she did much anymore, so it was with careful steps that she walked down the stairs and across the road heading home. Looking up when only halfway across the road, she stopped suddenly, seeing Alex and the impromptu picnic he’d set up, bringing a happier smile to her face than she’d felt in an awfully long time.

“Hi! I’m Alex. Would you like some coffee or tea?” he asked in such a sweet way holding the cups out for her.

“Yes, I would love some,” she said quietly and taking the tea, sat on the other side of the box of donuts. “Amanda,” she said holding out her hand and feeling only gratitude when he took it in both of his, a very comforting gesture. She looked back only briefly towards Dan’s grave and felt completely settled on her decision. “What a lovely thing to do,” she said with a friendly smile, but added with a slight edge to her voice, “and not very naughty, I might add.” They both laughed, feeling instantly more comfortable in each other’s presence.

“Well, you never know when that might change,” he said but quickly changed the subject to a ‘getting to know you’ type of conversation. Alex started giving her a brief history of his life, mentioning spanking occasionally, although, to a knowing ear, it was clearly woven throughout his story. He finished with the one thing they had in common so far: the Seniors Spanking website.

“I don’t know if it’s the same for the men listed, but it always surprises me how many young women there are … on a site for seniors! … most of whom are just looking for a long-term relationship, with no interest whatsoever in spanking, and if spanking is in play, they’re looking for the whole BDSM experience, especially the ‘seniors’! Was it the same for you?”

“Not many young men at all, but the same as you’ve described in the other areas. Those who list spanking as an interest also have all the other submissive desires as well. I know I clearly don’t understand that mindset, and I believe in ‘live and let live’, but the idea of leashes, cages, whipping, and chastity? Yuk! Some of them made me sign off immediately in disgust.”

“I agree. I never would have thought my interests would be considered uncommon in such a community. So, tell me about you,” he suggested knowing she might be reluctant.

“I don’t think you want to get me started on me and my husband, do you?” she said doubtfully.

“I don’t think I can know you unless you do. I imagine you had a very special relationship; one I may be quite envious of, but as long as you don’t compare us to each other, I’d like to hear about him.”

“You’re very sweet, you know. Are you trying to make it difficult for me to spank you?” she said smiling, almost giggling.

“Certainly not!” he replied, getting a very hopeful outlook on his chances.

“Dan was a very special man,” she started but took Alex’s response as hopeful as well. She went on to describe their history together, eventually giving special attention to the more than weekly spankings she gave him. Some playful, sexy foreplay initiated by either, some role-playing punishment, and occasionally real punishment though still with a role-playing side to it. Alex took this hopefully as well, seeing their compatibility increasing the more she said.

“If this is a painful question, just ignore it, but … how did he die, Amanda?” he asked more suspecting that it had to come out if the story were to be complete and allow him into her life.

“It was very sudden and unexpected,” she replied sadly but with a resignation showing she had come to terms with it. “It was early morning … a Saturday so we were still in bed when he got up and just collapsed on his way to the bathroom … still naked. It was a brain aneurysm we had no knowledge of. I was obviously devastated, but I’ve gotten myself together over the past years even to the point of seeing one good thing about the way he died,” she finished with a surprising smile.

“What was that?” he asked, his curiosity peaked.

“He died with the bright red and severely bruised bottom I’d given him the night before! You should’ve seen me trying to explain that to the paramedics!” she said laughing in a way that made it clear he could laugh along with her. It was both a sad and funny memory that put an appropriate period at the end of her story.

“So … I like you Alex, and I’d like to get to know you better, but honestly, I’m already picturing your bare bottom across my knee. Is that too forward of me?” she asked with some doubt.

“Oh … I am surprised, but pleasantly so. I hope I’m not being too forward when I say I’d take my pants down for you right here if that’s what you wanted,” he said also worried he’d gone too far.

“Mmm, that would be nice, but while I don’t think your behavior warrants an immediate punishment, I do want you to come to my home tonight at eight o’clock prepared to spend a considerable amount of time across my knee with your pants down getting a long overdue and very painful spanking on your naughty, bare bottom. Do you understand?” she said in a voice between playful partner and stern mistress, her arousing demand already having its effect in Alex’s pants.

“I’ll be there, Miss. Is there anything you’d like me to wear?”

“It hardly matters as the only thing you’ll have on very long is your underpants, and they will likely come off rather quickly as well,” she replied smiling broadly this time.

They said little else, both feeling a new story had just started very nicely, so they packed up the picnic, exchanged addresses and contact information, and went on their separate ways after a brief but affectionate kiss. It had taken a while to get together but they both realized the delay had been for the best as they were both now in the right state of mind to genuinely enjoy this evening.