He closed the trunk of the car, having extracted his bags and slung his backpack over his shoulder. He extended the handle of his rolling luggage and waved goodbye to his wife with one hand, turning towards the entrance to the terminal.
As he stepped across the threshold and the doors slid closed behind him, he could feel the weight of responsibility lifting off of him. The burdens that his wife was constantly placing on him, her perpetual demands; all were melting away as he took his steps into the airport.
He found the check-in desk for his airline, showed his boarding pass and got his tag for his carry-on bag. He went to security and was just as frustrated as usual, removing his belt, taking his laptop out of his bag and removing his bag of liquids. He was glad that he was packing lightly for this quick trip. When he was through security, he went to grab a bite to eat before he sat down at the gate. He got a turkey sandwich that shouldn’t have cost him $17 but it did and he tried to enjoy it despite the dry bread and lifeless lettuce..
It was Thursday evening and in just three days he’d be checking something off his bucket list. An avid runner for years, he was going to run the Chicago Marathon, one of the World Marathon Majors. With six marathons in the series, Chicago was the most accessible to him, especially considering the nervousness around travel as the pandemic dragged on for a second year. The New York Marathon had hundreds of thousands of applicants and used a lottery system, making it tough to get into, and Boston had a firm qualification time that he was nowhere near achieving. It was already a big enough deal to travel to the United States from his home in Canada, so he would put London, Berlin and Tokyo on the shelf for a while as his overseas travel would be on hold for a little while longer.
But the real reason he was getting excited is that he would be seeing Jenny for the first time in over a decade. Jenny, the woman for whom he had fallen hard when they met at a corporate retreat over 13 years before. Jenny, with whom he had gotten back in touch over the pandemic, with her marriage breaking up and him being profoundly unhappy in his.
After over a year of talking online, things heating up and then cooling off, they were finally going to meet again. She had been somewhat distant, keeping things very cool with him for a while after a steamy few months in the late summer and fall the year before. He never knew what she was feeling for quite a long time. But they finally talked some more on the phone and resolved some things and agreed to meet up for coffee, at least to start with.
For well over a year, his heart had been beating only for Jenny. And while it wasn’t the only cause for the decline of his marriage, his realization of his feelings for Jenny was what made him understand his lack of them for his wife. The moment that it dawned on him how little he felt for his wife and how much he was feeling for Jenny, he realized the huge mistake he had made when he got married.
He still wasn’t quite sure of how Jenny felt about him, though. He couldn’t help but replay some of the things that Jenny had said to him at different points over the last year and a half and try to read into them. Did she really mean it when she said that that she was ready to illegally cross a border to see him? Was just about anything really on the table sexually? So many things had changed since then and her coolness towards him didn’t make him too optimistic.
At least he had something to keep him occupied this weekend and it wasn’t all about her. If things didn’t go they way he wanted with her, he’d still have something big to cross of his “to do” list.
His stomach was in knots as he waited for the plane to board and he needed to temper his emotions while waiting for the plane to board. He tried to distract himself by reading his book on his phone but his thoughts kept coming back to her. He tried to focus on his running. He went over his game plan for the race. He went over his fueling strategy. He looked at the weather to better plan what to wear. He looked over the course map, trying to visualize what he’d see and hear and feel at ground level.
Time both stretched and flew. but before he knew it, it was time to board. He found his seat on the plane and got as comfortable as he could. Since losing 30 pounds training for the marathon, he definitely fit better into the tiny airline seat. He had the window seat and there was a young looking couple sitting in the two seats next to him; definitely a big improvement on the squirmy baby sitting on the well-built father’s lap he had next to him on his last flight, several months back. He pulled the inflatable pillow out of his bag, blew into it to inflate it and put against the aircraft bulkhead. He leaned his head against it, closed his eyes and let his thoughts wander.
Of course they wandered to Jenny, wearing a feminine, yet somewhat conservative dress as she approached him for the first time. Kissing him deeply, her tongue exploring his mouth as her hand caressed the back of his head, running her fingers through his thick hair. He could almost feel the curve of her hips and as he put his hand on them and pulled her close, the feel of her tongue in his mouth, the warmth of her body next to his and the smell of her scent as he inhaled. Then they were in his hotel room and she was backing him up and pushing him on the bed, pulling his pants down, the warmth of her hand and mouth on his cock as he got harder and harder.
A jolt of turbulence broke him out of his reverie and he realized that his pants were fitting just a little tighter than when he dozed off. He took a quick look around to make sure that no one noticed (they hadn’t) and he checked his phone to see how much time had elapsed. Just 20 minutes or so had gone by since they had taken off. It wasn’t a long flight, Toronto to Chicago, but he almost couldn’t wait until he landed.
He passed the rest of the flight reading, watching a TV show he had downloaded to his phone and just otherwise trying to distract himself from the real reason he chose to run the Chicago Marathon. Ok, it was a dream to run it, but his desire to see Jenny easily overpowered the allure of a big event like the marathon.
Soon enough the plane landed and pulled up to the terminal. He exited the plane and caught a taxi to his downtown hotel, close enough to the start of the race that he’d be able get to and from pretty easily. He rode up the elevator with his minimal baggage and checked the clock. It was only 9pm. He had to keep reminding himself that Chicago was an hour behind his accustomed Eastern time zone.
He was exhausted. But first he pulled out his phone and connected it to the hotel WiFi. He could easily afford the fees his cellular provider charged for roaming in the US, but he hated himself for relying on that, and since he didn’t expect to be leaving the hotel tonight, he didn’t want to incur charges for that extra day, even if it was only $10.
Once connected, he checked his emails. He texted his wife that he had landed and arrived at the hotel and did the same for his parents. Even though he was 45 years old, his parents still insisted that he check in whenever he traveled. His duties completed, he turned to his next task. He texted Jenny. “Landed in the Windy City,” he typed. “Hope the wind is at my back on Sunday!”
He put his phone down and went to the washroom to grab a shower and wash up. He didn’t expect Jenny to respond right away (if at all). Their communication had been tenuous since reconnecting after he wished a happy birthday back in June. She told him she didn’t want to have full blown text message conversations they way they had before and she would write to him once in a while. Sometimes he’d write back and go unanswered for a week or two. The frustration and emptiness of this treatment had had him on edge for months. Every once in a while, she’d tease him with a morsel of friendliness. An occasional comment on the crossword they both did every day, or a passing thought about running (a pastime they bonded over initially), or something about their shared line of work. He would be careful, trying to stoke these shards of connection into something that resembled a conversation but she would always pull back. She used her busy schedule, trying to be a single mom, trying to figure things out with her husband as excuses and he really tried to see things from her side of it but was frequently just left sad and lonely to have lost this incredibly deep connection and long-time friend.
He had avoided any sexy talk as it seemed to push her further into her shell. But he remembered vividly how just a year before, their conversations were enough to get his heart racing and the blood flowing to his penis in seconds.
As he finished up in the shower, he heard his phone ping. Usually he kept it on silent when he was around his wife, but now that he didn’t have to worry about her, he let it make whichever sounds it made.
He picked up the phone and noticed that there were three messages from Jenny. “Welcome!” the first one said, followed by, “I think I can find some time for that coffee on Saturday.” A few minutes later a third message had come in, that ping that he had just heard coming out of the shower. While seemingly innocuous, this third message was even more interesting, “What are you up to?” she asked.
That was more like the Jenny of yesteryear. Lately she never asked him about his life. Just random comments that were rarely connected to anything else. “Just got out of the shower. You?” he replied.
He went back into the bathroom and started to brush his teeth when he heard another ping. He finished brushing, taking his time to make it seem like he wasn’t jumping at his phone. he tied his towel around his waist and went back into the main room. While he wasn’t as thin as he had been in his 20s, he certainly felt much better about how he looked after losing most of the weight he had put on during Covid when he started to take his fitness more seriously in training for the marathon. “Just got into bed ;)” she had written.
Oh, it’s on, he thought and smiled to himself. While he was fairly sure that she was down for some sexting, he didn’t want to make a move unless he was 100% sure and he gave her the perfect opportunity to back away. “Early night?”
“Not yet… gonna unwind a bit first first,” she replied. He recalled the first time she had mentioned “unwinding” the year before. That conversation came with some very naughty messages on her part.
“Maybe I should unwind too. I’ve had a long day.” he wrote.
“It could be,” she wrote back. “Are you dressed to unwind?” she asked.
“Well, I’m still just wearing my towel.” He added a winky emoji to add a little extra flirtatiousness.
“Show me.”
He opened a chatting app, changing the setting to let the photo disappear after she viewed it. Then he turned on the lights and stood in front of the mirror. He held up his phone and snapped a photo, sending it to Jenny.
He settled himself in the bed and waited for her to respond. When it came, he instantly got hard. She sent a picture of herself in a blue bra and panties set with one hand down the front of the panties, her eyes staring right into his soul.
He wrote back, “you just made a tent in my towel.”
Her reply was just a winking emoji.
He went to his bag and grabbed his wireless headphones and initiated a video call, hoping that she would answer and that they would have some fun. The call connected and he saw her face there on the video screen. His heart melted and his breath caught in his chest. “Hey Jenny,” he said in his deep voice, trying not to betray the shakiness in his stomach. “It’s so good to see you.”
She smiled coquettishly at him and then, as she panned the camera down her sexy body, his cock rose. She whispered, “I can’t really talk. The kids. But I still want to hear you and see you.”
He panned his phone down so that his the towel was now taking up the bulk of the view and he slowly opened it, revealing his smooth, freshly shaven cock, erect for her.
He could hear Jenny start to breath heavily as he moved the camera around to highlight his throbbing cock from different angles. A small moan escaped her lips. He started rubbing his cock and a drop of precum escaped and he rubbed the slick fluid around its head. “Oh my god,” she breathed. “I want that…” and her voice trailed off as he saw her eyelids flutter in pleasure. “I want it in me,” she whispered.
“Show me where you want it,” he replied, letting.
She took her turn to lower her phone down to her groin area…. her hand was still under her panties, rubbing. He continued to guide her. “Pull your panties to the side.” She did as he told her, pulling the panties to the side and exposing her pussy lips and a small tuft of hair protecting the top. “Now rub it.” She rubbed it, he could see her pussy glistening with juices and he could hear her breathing increase. “I can’t wait to see it in person. I’m going to lick it and get it so wet for my cock, Jenny.”
While she may not have been able to return his dirty talk with her kids sleeping in the next room, her heavy breathing got him so hard. He watched as her fingers rubbed her mound. She dipped her fingers into her pussy and showed the slick juices on them to him. “Oh my god, Jenny, do you see what you do to me?” he asked as he panned down to his cock, rigid and swollen with pre-cum lubricating the head. As he rubbed the head of his dick, he imagined her lips surrounding it, her tongue swirling around it. He heard small moans accompanying her breaths. “I wish you were here sucking my cock, Jenny,” he breathed.
“Oh yes,” he heard on the other end of the line. “Oh yes,” she said between her moans.
“Take off your bra, Jenny,” he said, slowing down the rate that he was stroking his cock. “I want to see all of you.”
She put her phone down and he could hear some rustling sounds form her end. When she picked up the phone, her breasts were free and on display. Her small areolas were so cute and her nipples were hard. She caressed one with her free hand and he enjoyed the little bounce when she pulled her nipple outward until her fingers popped off, her breast rebounding. She moved her hand back to her pussy and her moaning continued.
“You sound so sexy Jenny, you get me so close.”
“I want to see that,” she whispered, “Mmmm.” Her breathing became faster, more ragged.
“What do you want to see?” he asked.
“You know what,” she hissed. “Let’s finish together.”
He maneuvered his phone to a position in which she could see him start to stroke faster trying to keep the device out of the inevitable path of hot cum.
He stroked faster, responding to her quickening breaths, and moans that got louder and less controlled. “Oh god, Jenny. Look what you do to me,” he said.
He heard her breath catch, accompanied by a small little squeal that was barely audible, pushing him over the edge. “Now,” he heard in his headphones. “Now.”
He increased the rate that he was pumping his cock. He was sure that Jenny could barely see anything but a blur but the hungry look in her eyes was intoxicating. “Mmmm. Oh, let me see it,” she breathed.
“Uhhh,” he groaned. “Fuck, Jenny.” His cock was twitching now and he felt the orgasm explode from deep within him. The first jet of cum rocketed from his cock, landing on his upper chest while the second wave was a smaller but a thick wave oozed out. The third was almost as strong as the first, landing on his stomach and then his cock just continued to trickle thick white cum for a few more seconds. He lay back, bringing the phone back up so he could see her pretty face.
She mouthed the word “Wow” and he smiled. “Wow right back, Jenny.” She blew him a kiss and hung up the call.
He leaned his head back and tried to catch his breath. He used his towel to mop up the copious amounts of jizz that had flown all over his torso. His phone pinged.
“Thanks for that, Ricky. That was fun. So I can meet up with you on Saturday for coffee and I think I’ll have some time for dinner too. My mom’s gonna come over to watch the kids around 4.”
“Awesome. And after dinner?” he replied.
“That’s going to be a whole other story,” she wrote. “Night night, Ricky.”
“Night night, Jenny.”
Rick lay back on the bed and his eyes closed momentarily.
This marathon weekend was off and running.