He awoke the next morning with an erection as hard as he could ever remember. He didn’t sleep well with thoughts of Jenny, the naughty looks she had in her green eyes, her sexy body and the sound of her moans all running through his head.
It was 6:30am, around the time he usually woke up and he stepped into the bathroom to relieve his bladder. He washed his hands and emerged and changed into his running clothes. He’d go for a quick and easy 3-mile run to keep his motor running for the marathon in just two days now. His phone pinged and it was a message from Jenny. “Probably not gonna be able to talk today. It’s gonna be one of those days.”
He sighed to himself. He didn’t have a lot to do today and had hoped for some chatting with Jenny to pass the time, and now he didn’t know how he was going to get through the day without jerking off several times. He’d have to burn off some of that sexual energy on his run.
He had scouted nearby places to run and settled on a quick trip along the lakeshore to really experience Chicago. The run was uneventful. Just a nice little shakeout as part of his taper. You don’t want to go into a marathon running full bore; he’d been gradually easing off his distance and intensity for a few weeks now to help his body recover from the punishment of the most grueling part of his training. Feeling fresh and raring to go, he felt an ease as he jogged to loosen up his muscles and joints.
He thought back over his whole relationship with Jenny. The time they spent at that retreat 10 years ago, going for morning runs together. He thought of the time when they hung out as friends and briefly worked together on a project for their companies, and then the long gap in meaningful conversation as she got married, had a couple of kids, and moved overseas for a while.
Things heated up last year as they got a little flirty, which grew to being a lot flirty. Both of them married, taking some chances with dirty texts to each other. Although she was always worried that her husband was suspicious, and even reported that they would need to cool things off for a while because he had been checking her phone and computer, they always found their way back to indulging in their baser desires and giving in to the undeniable connection that they had always had.
And then, after she had returned to Chicago without her husband, she decided to cool things off even more. She cut off communication entirely, saying that she needed time to figure things out there; settling into a new life with a new job, as a single mother to two young kids.
Those months were agonizing. His heart was broken and he was finding it harder and harder to relate to his wife. He knew that he didn’t love her. He doubted he had ever loved her and now knew that it had been a mistake to marry her. The time without talking to Jenny really helped him understand his own marital dynamic and why it would have to end sooner rather than later.
But it didn’t hurt any less. He really felt that even a friendship with Jenny was better than the silence. And the friendship was always a bedrock of their relationship, even when he had pushed his feelings towards her way down because of her boyfriend who became her fiance, who became her husband and father of her children.
The months ticked away and, when he sent her a gift for her birthday, they resumed some chilly contact. He never knew where he stood with her. Finally, they had spoken on the phone a couple of months before and had a long conversation where they put some of the cards on the table. Some, but not all. He wondered if he would ever tell her how deeply he felt for her and how much she had hurt him with her silence. He didn’t want to scare her away and he didn’t want to be that honest with himself. He knew that she was the love of his life and he didn’t know what he’d do if the slim hope of them being together in the future was taken away from him.
A honking horn broke him out of his reverie. He looked around and saw there was almost a collision in the nearby street. He glanced down at his watch and saw that he had run about one and a half miles and he turned around to run back to his hotel. He was more aware of his surroundings this time as he breathed in the brisk October air.
He returned to his room, grabbed a granola bar he had brought for his post-run snack and hopped in the shower before heading down to a diner across the street for breakfast. He decided on a fruit-heavy breakfast that also included a couple of poached eggs for protein.
He looked over Jenny’s message again and decided not to reply. He knew that it likely wouldn’t get a response so he didn’t bother to put any energy into crafting a response. Things were hot and cold with Jenny and if she said that she wasn’t going to able to talk, she really wasn’t going to be able to talk.
He decided that it was time to do the one thing he had to do that day and headed over the race expo to pick up his race bib. This was one of the most exciting times in a race weekend. He could feel the energy radiating off the other runners and he got to check out some cool gear. He would stock up on some energy gels for the marathon and check out the latest advancements in shoes at all of the vendors. There were usually speakers including Olympic distance runners, ultra-marathoners and previous winners of this race. They were talking about all kinds of topics ranging from conceptual things like their inspirations for running or how they overcame illness to win Olympic medals to mundane but highly necessary things like what to eat and when to use the restroom before (and during) a race.
He went to the race check-in and signed and submitted his waiver and picked up his bib which included the electronic timing device that would enable people to track his progress in the race as well as keep his official time. The race kit also included a shirt, some samples of various things that the sponsors were selling: vitamin-infused water, electrolyte gummies, a sample of an extra-strength laundry detergent that was supposed to get the smells out better, and other such sundry items.
The conference center was full of bustle despite the fact that they were strictly controlling the number of people allowed in. The energy was quickly draining him and he wanted to get back to the hotel to rest. He needed to marshal his energy in the days before the race.
He looked at his watch. It was 11:30 am. He figured he’d grab some lunch, take it back to the room and chill out for the rest of the day. Touring a city by walking for hours and hours was usually his idea of a good visit, but he had discovered that when running a marathon, any energy expended in days leading up to the race would sap him on the day of.
He found a local sandwich shop and got a turkey sandwich and a side salad, with a bag of chips on the side. While “carb-loading” was a thing. It was more about making sure that he ate enough carbs in relation to other macronutrients rather than overdoing it in the days before the race. He also grabbed a big bottle of water. Hydration was key.
He grabbed the takeout bag and headed for the hotel. He put on his mask, entered the lobby and his heart just about stopped at the sight of Jenny (he instantly recognized her even with the mask covering her pretty face) sitting on one of the sofas, apparently waiting for him. Her shoulder length brown hair was pulled back behind her ears and her eyes had a playful glint in them. She was wearing a dress that went down to her lower thigh, her legs crossed and he could see her toned legs encased in black nylon. She was wearing low heels, practical for walking around and still pretty sexy to him, especially on her.
She stood up and walked over to him and they hugged. He practically lifted her off the ground, he hugged her so tightly. “What’s this?” he asked in a whisper, his lips right by her ear, albeit separated by the cloth mask. “What happened to ‘not being able to talk’?”
“Surprise,” she said, the smile on her face audible to him. “I took today off,” she whispered back. “I needed to see you.”
Lightly perfumed, her scent hit all the right buttons for him as their heads met, masks still in the way of any further physical contact. Holding their embrace, they pressed their bodies together and he could feel his cock starting to rise with her warmth pressing into him. He whispered, “We should get upstairs.”
With his race bag containing his lunch, his bib, race shirt and other samples and goodies in one hand and Jenny’s hand in the other, he led her to the elevator. When the doors closed, she put her head against his chest and closed her eyes, enjoying his nearness. With his arm around her and his chin on the top of her head, she felt like she was home.
They reached his floor and they both separated a bit and stood up straight as the doors opened. He led her to his room, let go of her hand and fished in his pocket for the keycard. He swiped the card and they heard the click of the lock and he swung open the door. He let her enter the room first and watched as her coat dropped to the ground immediately, her hand reaching to pull off her mask. He dropped his bag and took his mask off too. It seemed like he was floating as the space between them disappeared and her mouth was on his, her hands on the back of his head and his around her back, pulling her close.
Her lips were soft and soon she opened her mouth to let his tongue hungrily explore hers. He swirled his tongue around hers, pulled it back and her tongue chased his into his mouth. His hands roamed around her back, to her waist, her hips, sliding around the soft cloth of her dress. Her hands were in his hair ruffling it as their tongues played. The broke the kiss and both inhaled. “Wow,” they said simultaneously. He put his hands to either side of her face and kissed her again, he gently sucked on her bottom lip before pulling away.
She tore off his jacket and pulled his sweater over his head, his t-shirt coming off with it, leaving him bare chested. She ran her fingers through the sparse, dark hair on his chest, kissing him from his collarbone down the center of his chest, over his stomach. She pulled open his belt and unbuttoned his jeans and pushed them down, taking his boxer-briefs down at the same time. “God, I’ve been wanting this for so long,” she said, taking his quickly engorging cock in her petite hand. “It’s even better than the pics you send,” she breathed, her mouth getting closer and closer to the throbbing head of his penis.
He was trapped in the best way possible. His pants and underwear around his ankles, keeping him rooted to one spot. She was sitting on the bed, leaning over. She extended her tongue, licking a drop of pre-cum from the tip of his erection, curling her tongue back into her mouth and swallowing her prize. She moved her head closer and opened her mouth, engulfing the tip of his penis, sucking inwards. He groaned and leaned his head back. She released his cock and swirled her tongue around the swollen head of his cock before sucking the head and another couple of inches into her mouth again. “Ohhhhh,” he groaned. He felt light headed and as if he was going to be carried away by the pleasure that her mouth was giving him.
She noticed his knees buckle slightly and let go of his rod. She got up and let him step out of his pants, freeing him up. She guided him as he turned around and pushed him back on the bed. She reached down to the hem of her dress and pulled it upwards, over her head. She swayed her hips from side to side sexily as she discarded the dress. She was wearing a light blue bra and thong set, with a pair of black stay-up stockings. When he didn’t think his cock could get any harder, she goes and does this, he thought to himself. Stockings were his kryptonite. His cock twitched, more pre-cum dripping from the tip.
She hungrily approached and grabbed the base and admired his above-average length and girth. She lowered her head and slurped up the pre-cum, sucking as much as she could into her mouth. She started to bob up and down, coming within a couple of inches of getting the whole thing into her mouth. “Fuck, you taste good, Rick,” she said as she pulled her mouth off him momentarily. She stroked up and down, using her saliva and his pre-cum as lube as he lay back on the bed, mind going blank in ecstacy. He propped himself up on his elbows because wanted to watch this. The woman he had been in love with for over a decade, at long last, devouring his hard cock and giving him more pleasure than he could have dreamed of.
“Oh fuck, Jenny,” he said. She started bobbing her head up and down faster, taking in as much of his cock as she could in each stroke. Her hand at the base of his cock, moving up and down with her mouth. “Holy shit,” he breathed. “That’s so good,” he said. “I’m cumming.” She looked up at him with a mischievious glint in her eye, continuing to work his cock up and down.
She felt his cock start to twitch as he started to unload his semen in her mouth. She started to suck for all she was worth, trying to capture every drop. She collected it all and swallowed it, his cock still spasming as his orgasm passed. He flopped back onto the bed, eyes closing, catching his breath, feeling his heart racing. She took off her shoes, got onto the bed with him and curled up to him, his arm around her, holding her to him.
“Fuck, Jenny. That’s the best blowjob I’ve ever had. Ever,” he said.
She nuzzled him closer, stroking his chest, her hand going lower and lower. “That was just the warm up,” she said. “We’ve got a whole marathon in front of us,” she said with a wicked grin.