Gary had been traveling almost all day. With the delays at the airport and the traffic getting there, he was on edge.
The location and reason for the trip didn't help either. It had been years in the planning stages. The person he was visiting was someone he had known for years and yet, had never met.
___________________________________________
They started out talking on one of those meet-up sites. Not that he had ever thought he would go on one. He had been with his wife for many years and theirs was one of the happiest marriages of all his friends.
But even the best of friends can eventually veer onto different paths as they walk side by side through life. It didn't mean that he didn't love her. It just meant that at some point, their roads had diverged and every mile they traveled took them further apart.
Being someone who had strong emotions, he craved companionship in any form. He needed the conversation, the laughter, the shoulder to cry on, the body to hug, and the ear to bend.
So, one night, in the wee hours of the morning, in a moment of weakness, Gary went online and found a site for adults to meet and chat. He wasn't going in to find someone to have sex with in his area. He'd seen those ads. He wasn't looking to just find a quick hook-up for sex. Not only was it against his personality, but he wasn't ready to have that betrayal hanging over his head for years to come.
Honestly, he just wanted someone to talk to. Someone who genuinely wanted to listen to what he had to say instead of only thinking about what they were going to say next as if his thoughts weren't important.
__________________________________________
Her name was Kathryn. Not Kate or Katie. She hated that and had made that known from the start. It was Kathryn and anything else would be met with sarcasm and mocking.
Gary liked her immediately.
She was funny and understood his brand of humor and the way he talked via the keyboard.
He had learned early on that not only does 'sarcasm' not always translate in the computer but his special brand of sarcasm and wit needed an extra interpreter in the corner of your screen to get across that he wasn't being mean, he was just trying to be funny.
His wit was so dry, it caused desserts to be jealous.
But, Kathryn got him.
She laughed at the right times and she gave as good as she got any time they were talking on the site.
It started with quick, guerilla-like bursts of comments.
He commented on her page about one of her postings and she fired back, making him snort in response.
This went on for a few weeks as they were in different time zones and they weren't always in the same place of their day. He'd be getting to work as she was heading to her lunch break. She'd be heading to bed as he was just getting home for the day and sitting down to dinner.
Then, there was the one evening that he had finished dinner and settled down for the night when he checked on the site and she was there.
The moment he logged in, she was there on his page with the comments and asking about his day. He was pleasantly surprised to be able to talk to her for more than ten minutes at a time and they settled down into a lovely rhythm of talking and sharing and making each other laugh. Before they knew it, it was one in the morning his time and almost five in the morning her time.
Gary apologized effusively for keeping her up so late but she assured him that she had been enjoying their conversations so much that she had planned on talking to him as long as he wanted.
They were both pleasantly surprised at how natural the conversation felt. It's one thing to spend time sharing one-liners but a whole other animal having a full, meaningful conversation with someone who you have never met in person.
From that night on, they made a point to reserve at least one night a week to stay up late together and chat. Throughout the week they still left messages for each other.
They commented often on how amazed they were that they had become fast friends and truly enjoyed every moment they shared.
They eventually knew everything that was going on in each other's worlds. Birthdays, gatherings, deaths. The small things, the big things, it didn't matter, they shared at the end of every day.
_____________________________________________
It wasn't a huge step to go from a great connection of friendship to true flirting and sexual innuendo.
The comments started innocently enough.
A comment that something during the day was hard followed by, "I bet it was, wink, wink."
Then leading up to flat-out sexual comments when the need arose, "Like your cock, probably."
Any conversation they started could and would end up with them turning it into sex talk which led to asking each other about their tastes and experiences.
At first, it was a more conversational style. They might as well have been talking about what they did last weekend for all the intimacy the dialog held. They were like two best friends who were comparing notes on their exploits.
But then, one night, late into the evening, she came right out and said, "I've been wanting to say this for a very long time but I didn't want you to think I was a slut or anything. Your opinion of me matters greatly. I have really enjoyed our talks and the blossoming friendship and I didn't want to damage it..." and here she paused her typing.
Gary waited for her to continue and when she didn't in a timely manner, he nudged her along.
"It's okay. You can say whatever it is you want to. Because I can guarantee you I am thinking the same thing." he typed.
He watched the little ellipses flash as she typed, and he waited, not realizing that he was holding his breath.
Finally, her reply came through.
"Would you consider using the video feature some night and..." she made him wait again.
"And?" he prompted.
"Playing cribbage with me? I've always wanted to learn and you mentioned once that you play." Then she posted a laughing emoji with tears rolling down its cheeks.
Gary sent a smile back, but in real life, he was frowning because he was hoping she would say something else.
After a few moments, he received a new message.
"Just kidding. Honestly, I was going to say, that I have enjoyed our time chatting and you've been such a gentleman and I would be lying if I said that I haven't thought more than once about verbally jumping your bones. So, I was wondering how you would feel about that some night?" she asked.
It was his turn to make her wait.
Partially for the cribbage comment and partially because he had been thinking about it too but wasn't sure how to approach it. Now that it was being offered to him, was he ready to cross that line? He wasn't used to this whole digital flirting thing. He didn't mind meeting and talking to people he'd never met. He did that in everyday life while waiting in line for a coffee. But she was asking him to go a step beyond what he'd do normally.
'Was it cheating to have the equivalent of phone sex in today's day and age?' he asked himself. He reasoned that it was emotional cheating but not physical. Is one the same as the other? Could he do it without feeling guilty around his wife? The woman whom he had married so many years before and who had since let their marriage dissolve as if you took a hand of sand and placed it under water. The grains of sand would erode off your palm, leaving nothing of the original pile behind.
There were still feelings there, on both sides. But they had become more roommates than husband and wife. The intimacy had faded away like the sand as well until they were cordial but no more than they needed to be. Neither one wanted to admit that their marriage had run its course.
As he sat there, watching the screen, as well as the clock tick the seconds by, he realized that he wanted this too.
It felt like he had been making her wait forever on the receiving end of his reply when all this had gone through his head in a matter of moments.
As he saw her begin to type again, his fingers hit the keyboard with a staccato tapping and he typed three words.
He saw her response pop up as his became visible to her.
Hers said, "If I have overstepped, I am sorry. I didn't mean to assume that you felt the same way. I wanted to put it out there but I completely understand and we can keep things the way they are if you'd rather."
His reply said, "Yes, I would."
Then, they both just stared at the screen for a few moments and there was silence between them.
They waited for the other to make the first move.
And waited.
And waited, till they both thought that the other had fallen asleep.
Finally, those three little dots started to blink indicating that she was responding and his heart started to beat again.
A photo appeared.
They had shared some snapshots of each other early on, but only selfies and headshots. It was always nicer and easier to find a connection when you knew what the other person looked like. At least for Gary, it was.
She was hard on herself, but Gary thought she was beautiful. She had the best smile and it lit up her eyes when he made her laugh.
This photo was everything those previous photos were not.
Kathryn was standing, hips cocked to the side, one hand on her prominent hip, the other softly resting fingertips against her chest just above her breasts, which were sheathed in a lacy burgundy bra.
She had a matching pair of panties on as well and they hugged her hips as if they were painted onto her body.
He had only seen photos of her in baggy clothes or the occasional night-shirt that was usually just an oversized t-shirt.
Gary honestly had no idea of the shape of her before this moment.
His heart stopped for a moment. The two of them had built up such a great connection in their conversations since they met. In the real world and growing up, Gary had always been attracted to looks first and then learned about the person as they spent time together. That was the one advantage of meeting people online. You got to learn how compatible you were with someone first and looks were secondary.
But when the image reached the photoreceptors in his eyes, his brain almost overheated and his heart almost exploded.
He knew that time was ticking away and that Kathryn was waiting for a response. He didn't want her to think for one moment that he was disappointed in what he was seeing.
"All I can say for the moment is, Wow!" he typed.
"Is that a 'good' Wow or a 'holy cow, my eyes are burning,' Wow?" she asked.
"Are you kidding me?" he wrote back. "It's a "Fucking incredible how did I get so lucky" Wow," he replied.
This gained him a smile in return.
He didn't have a photo to share with her, but he promised her that as they progressed, he would reciprocate.
_______________________________________
With the encouragement he had given her, she started to send him some more photos, each one a bit more seductive than the last. She knew he was married but also knew the state of the marriage. Plus, she enjoyed knowing that she was making him happy. She never assumed they would meet in real life and what harm could come from making him smile and have a better day. Not to mention, and not that she had told him, but she thought he was incredibly handsome and sweet and unlike any other guy she had met on the adult site. So many of the other guys just started out sharing their penises as if she was supposed to fall madly in love with them for it.
Gary hadn't done that. He had told her that, yes, he found her attractive, but he had asked about things on her profile, and that had granted him access past the first gate. After that, it was simple chemistry. They clicked like no one else she had met so far and he made her laugh and smile and their conversations were something she looked forward to every day.
They had even found time to talk on the phone a few times, and it was like meeting up with an old friend. Not awkward at all. They picked up right where they left off the previous night typing and it was nice to not have that delay while the other person was working on their response.
If she were being completely honest with herself, if Gary lived closer, he would be just the kind of guy she would try and seduce.
She had been told before that she was attractive and she guessed she was a bit. But she never really believed it. The few guys that had said so, had fooled around with her and then moved on spouting some crap about it being them, not her.
But Gary seemed genuine in everything he said. His reaction to her photos made her feel wonderful and warm inside. Knowing that he first liked her for her personality and not her body helped. Also knowing that they were somewhat far apart, and the chances they'd ever meet were slim to none meant that he had no reason to lie just to get in her pants.
Kathryn wanted to reward him as well. He had been very patient over the last year. They had been playful and he had intimated that he would love to see more of her, but she always changed the subject. It was time he got something special.
So, she was playful and sexy and flashed him as much as possible and ended with a photo of her sliding her bra off, draping it around her neck so the cups still covered her nipples but her cleavage was on full display.
_________________________________________
Gary saw the latest photo and he almost came in his pants. He had seen breasts and bodies before. He even got to see his wife's every day. But she hadn't let him touch her in years. It was like a permanent strip joint—all the turn-on with none of the satisfaction.
But seeing the body of someone whom he had grown to know and admire and even start to care about, it was like he was a teenager again, seeing a girl's body for the first time. The excitement, terror, and arousal he feeling, felt like the first time and it was so refreshing, he had forgotten how wonderful it was to anticipate something to do with sex. Even if it was over the computer.
All he could do was send Kathryn photos of him smiling a big, stupid, admiring grin after each shot.
What he wanted to do was unzip his pants, pull out his hardened cock, wrap his fingers around the hot, hard shaft, and stroke till he did shoot a load of cum in the air to land back down on his stomach and he wanted to show it all to her so she could finally see that he wasn't just saying that he found her beautiful. He knew she had self-esteem issues. Hell, everyone did. But he did find her stunningly gorgeous and sexy as fuck.
Unfortunately, he wasn't alone and couldn't take the chance of getting caught with his dick in his hand stroking off to photos that weren't simply a porn site.
Personal photos were better for his arousal but much worse for his health if he got caught looking at them. Weird how that worked.
__________________________________________
That all happened four years ago.
Since then, Gary and his wife have separated. It was mutual and amicable and they went their own ways.
Gary had continued to talk to Kathryn and their evening chats had taken on a whole new tone as he didn't have to worry about getting caught with his pants down, quite literally.
They had spent many evenings arousing each other with words, photos, and even video chats on those evenings when she could stay up late.
Having sex online was very freeing as they could play in any way they wanted to. They might not both be into restraint, but they could pretend.
They were adults and had fantasies about things they wanted to try at least once in their lives, and they both agreed to be honest if it came to something that they simply didn't want to do or explore.
One of her fantasies had always been to have a stranger enter her place and take advantage of her. Nothing violent, purely sexual. When they played out that fantasy, she always got the wettest and came the loudest.
He loved hearing her orgasm. She was incredibly vocal and verbose when she was exploding. Not to mention her vocabulary got extremely dirty when she was climaxing.
That was what usually pushed Gary over the edge. He had some of the most productive cums of his life with Kathryn. Even at his age, she coaxed more cum out of him than he had ever had, including when he was stroking to porn as a teenager.
Now, here he was, after many years of talking and playing and fantasizing, on his way to Kathryn's home, to see her for the first time.
They had been tossing the idea around for about two years since the separation became final. But their schedules would never mesh or something came up.
Gary finally had some time off and some extra money to make the trip. Here was, sitting in the cab, both anxious and terrified of what was about to happen. She would be the first woman he had been with in any carnal way for over thirty-five years. No pressure.
______________________________________
He had been following his journey on his phone and when he got within ten minutes, he sent her a quick text letting her know. According to their plan, this was to be their only communication before his arrival.
Tonight was all about her.
As the miles passed, Gary was getting harder and harder in anticipation. His heart was also beating faster and faster and his palms had started to sweat. He popped a mint into his mouth so he didn't have travel breath when he arrived.
The cab pulled up outside the address and he prayed that it was the correct one or this was going to go pear-shaped very quickly.
He got out, grabbing his bag as he slid across the car to get out on the sidewalk side. As he leaned over to pay the cab driver, he noticed her eyes staring at his crotch and the large bulge that had grown there in the last few miles.
"Sorry, it's been a while," was all he could say to her.
"You should get that looked at," she replied. "Even if you are on the way to get that checked, I would be willing to be a second opinion for you later if you like," she said, smiling mischievously.
"Thanks, I'll let you know. Keep the change," he said, smiling back.
She handed him a business card and said, "You keep that. Just in case. I get off at 11. I can get you off by 11:30," and then she drove away.
Gary stood up and thought to himself, 'Well, that didn't calm my situation any. I'm going to be done before I even enter the house.'
___________________________________________
He walked toward the home. He had been given very explicit instructions. He was to go around to the back and when he got there, he was to go to the fifth planter to the left of the door and search for the key to let himself in.
Thankfully, the key was there, which was a pretty good sign he was in the right place and wasn't about to get shot for breaking and entering.