She and Whistler Man chatted for hours the night they matched. We need a better name for him… Jason. Let’s call him Jason.
She and Jason chatted for hours the night they matched. He was funny and charming and showered her with compliments. It was a Tuesday night, so they arranged to meet up for a date that coming Friday.
She had started her new job the day they connected. She was still struggling with her decision to change careers and was feeling a lot of stress and anxiety. So when Friday rolled around, she really wasn’t in a social mood. The thought of making small talk and, once again, briefing some new guy on her traumatic dating history was the last thing she wanted to do. However, when he texted her about it, she was reminded of the connection she felt towards him, even if it had only been via text, so she decided not to bail.
Luckily, his family lived in her end of town so they were able to meet up at a little pub close to her house. She arrived before him and was sat a high top in the bar. It’s so awkward being the first one to arrive for a date. Do you get up and hug when they arrive? Do you wave them down if they don’t see you? If they’re running late, you just sit there like a loser for however long it takes them to arrive. So annoying. Fortunately, she was just a tad early, and he was right on time.
Their eyes met from across the crowded restaurant. Shew knew he was tall, but she didn’t realize how tall. He must have been 6’5, minimum. “Yaasss!” she thought to herself. He had his mask on, but she could see his gloriously thick and well kept beard peeking out. He wore a flat beak skater hat, a zip-up hoodie, and a pair of jeans. His “fancy jeans”, he would mention later on. In all fairness, he didn’t pack for dating, he packed for family relaxation. His style definitely screamed, Man/Boy, but she reminded herself that he was a snowboard instructor in Whistler. How else would she have expected him to dress?
He approached the table and sat down quickly. Phew! No awkward hug. They both stared at each other, giggling awkwardly. She didn’t know why she was so nervous! It’s not like this was her first date since her ex or anything. Maybe his nervousness was rubbing off on her? Whatever it was, the longer their stared and sat awkwardly, the more the sexual tension mounted between them. They had had some racy conversations over that past week, and it seemed they didn’t even need to speak for that chemistry to boil up inside them.
The server came over and they ordered some drinks. That seemed to break the tension a bit. He asked her about her job, her family, her life post-breakup. She asked him about his passion for snowboarding, his life out in Whistler, and his family whom he came to visit. Once they got to chatting, the conversation flowed like water. She was so comfortable and he was so easy to talk to. They compared dating war stories, he told her about the crazy surgeries he’s had to have due to snowboarding injuries, and she told him about how she chipped her tooth at that exact restaurant when she was drunk one time. Same, same.
Their drinks came and they ordered food. The food wasn’t great, but the conversation still was. Once they were done eating, they decided they would walk over to a little pot shop around the corner. They split the bill (which she wasn’t used to, but also wasn’t offended by), and headed over to buy some weed.
Unfortunately, it was 11:05pm when they arrived, and the dispensary closed at 11pm. They stood out front for a few moments, figuring out what to do. As they decided, she just stood there shivering. It was then, with his hands in the pockets of his sweater, he opened his arms wide and offered to keep her warm. She cuddled up to him and he just enveloped her up in his hoodie, his arms wrapped tightly around her. She just melted in to him. There are few things in this world that can top being hugged by a tall, warm, sweet guy in a hoodie. It was one of the best hugs she’d had in recent memory.
It was then that she looked up at him, the top of her head barely reaching arm pit level. He was gazing down at her, that look in his eye. You all know the look 😏… He leaned down, she reached up, and they kissed. It was sweet and soft at first, but the passion grew the longer they stood there lip locked. Their make out sesh was paused as they heard the bell of the nearby pizzeria door open. They both turned as a pizza guy walk out.
She looked, and did a double take. What are the friggin chances?! Not only did this pizza guy happen to be someone she had matched with on Hinge many months prior, this particular guy was actually someone she had gone to high school with! He looked over as he walked out the door, and there really was no getting around it, he definitely saw and recognized her. She was hard to miss with her blue hair. She turned and hid her face in Jason’s chest, and through muffled laughs told him that they had to leave there, post haste!
They walked around the corner, now holding hands, and he invited her to come back to his place. By his place, he meant his parent’s place. No judgement, obviously. She still lived with her parents (lived with her parents again, rather), and he was just visiting. Who was she to say anything? Still, parents are not typically conducive to a sexy good time.
“They’ll be sleeping,” he said as he tried to convince her. She weighed her options, and was actually leaning more towards just going home, but then he hooked her in with the promise of a massage. After all the stress she was dealing with in regards to her job, she actually really did need one. So she agreed. He had taken a cab to the restaurant, so they headed over to her car and she drove them back to his place.
They snuck in quietly, the sound of the TV blaring from the basement. Jason told her to run upstairs, as he went down to investigate. She scurried up to his bedroom, sitting awkwardly on the corner of his bed. A few moments later, he walked in and closed the door. His parents were still awake watching a movie, so no funny business could be had. Instead, he set up his laptop to watch a movie, and he crawled in behind her on the bed, positioning himself to give her the massage he had promised.
They agreed to watch The Addams Family (Halloween was the next day, after all). He rubbed her shoulders and her neck as they watched Wednesday Addams try to behead her younger brother (That’s true romance, right there). But as his hands went back and forth in very PG areas of her body, slowly, they moved their way down. Soon, she was leaning back against him as he felt her up over her shirt. She could feel his excitement in the small of her back. The tension just kept growing and growing. They both wanted to just rip each other’s clothes off, but couldn’t risk getting caught by his parents. Eventually, though, his hands moved further south, and he began undoing the button of her jeans. Unzipping the zipper. Slowly reaching his hand down when –
KNOCK! KNOCK! KNOCK! “Jason? Are you up?” his dad’s voice rang in from behind the door. “I’m sleeping, dad. Goodnight!” Jason, the 40 year old man, shouted back (😆).
They froze there for a few moments. His one hand on her boob, the other lingering just outside her jeans. They heard his dad’s footsteps head back downstairs, and it was in that moment that they just couldn’t hold back any longer. Within seconds, he flipped her around, both their shirts came off, and they began a crazy intense make out sesh.
He rubbed her outside of her jeans, she did the same. Soon his pants her off, hers on but fully unzipped now. She sat on top of him, straddling him, grinding slowly. Without her saying anything, he reached up and started choking her gently, but with just enough force that she felt her entire body tingle. She wanted nothing more than for him to rip her clothes off and just take her. But they couldn’t. They just kept teasing each other, the sexual tension building and building. Fuck. It was so hot.
Eventually, there was nothing more they could do in the situation they were in. They tried to just cuddle for a while, but they always ended up fooling around again. Around 2am, she decided she had to go. Jason was still in town for a while so they agreed to get together again. It just so happened, his parents were heading up to their cottage the next day. However, the next day was Halloween and she already had plans to go to her friend’s Halloween party. She invited Jason to come, but he opted not to. So they agreed that she would just go over to his place afterwards.
She thought about him the entire next day. He texted her to come over earlier, but she had a bunch of stuff to do before the party, and had also promised her friend that she would go over early to help decorate. The anticipation just made things even hotter.
Night fell and the party was in full swing. It wasn’t a huge turn out considering they were still smack dead in the middle of Covid, but it was a fun time nonetheless. This group of friends happens to be really in to the rave scene, and they love all that EDM music. Definitely not her cup of tea, but she always tried not to be a Debbie Downer. It wasn’t until whichever DJ came on the playlist who played really bass heavy type stuff that she finally had to say something. She had been drinking, obviously, but was also able to get her hands on some shrooms, no thanks to Kyle. But maybe this wasn’t the best place to do that, after all? The bass was heavy and it felt like it was penetrating her soul. The other party goers graciously changed the music when they realized how fucked up she felt, but even still, she just felt like she was on a different level than the rest of her friends. She texted Jason and told him she was leaving the party early (if 1am is early?).
Surprisingly, the cab arrived in no time, and she was on her way. Dressed as a School Girl, short, pink, plaid skirt and a white, midriff bearing tie-up top, she hauled her giant duffle bag with all her clothes and Halloween costume supplies and headed over to his place. He was waiting for her at the end of the driveway when she arrived. She drunkenly stumbled out of the cab, lugging her duffle bag behind her. He chivalrously took it from her and carried it inside.
As soon as the front door closed, they were all over each other. He had her up against the wall, leaning on the stairs, and they even, somehow, ended up on the kitchen floor. She was fucked up but she was definitely aware enough to know this was fucking hot. They moved the party upstairs and just ravaged each other. Kyle was still the best sex she’d ever had, but she remembered thinking that Jason was definitely a close second. She loved a guy who could anticipate her desires and embrace her freaky side without her having to say it.
Eventually they had exhausted each other and needed a well deserved break. They cuddled and talked, not that she could remember the conversation, and after a little while they went down to the basement to watch a movie. He poured them each a glass of wine (oh yea, like she needed that…), and they put on The Addams Family Values (because, of course!). He sat on the couch and she cuddled up to him, laying her head in his lap. Not sexually, believe it or not. However, as they watched the movie and she inevitably readjusted herself, he began touching her all over again. Teasing her, revving her up and then slowing down. It was torture. The best kind.
They fooled around like that for a while until they noticed the movie had finished. It was about 5am at this point and they both agreed it was time for her to go home. She called a cab and they waited together in the kitchen, watching for her ride from the kitchen window. As they waited, they, again, just couldn’t keep their hands off each other. Neither of them could get enough. Unfortunately, the cab didn’t take very long. They shared a long, deep, passionate kiss and they said their goodbyes. She got in the cab and watched Jason watch her drive away. It wasn’t until that moment that she was truly disappointed that he didn’t live there.
They messaged a bit the next day, but their conversation dwindled throughout the rest of the week that he was still there visiting. He had told her which day he was going home, so she texted him to have a safe flight, but didn’t get a reply. It wasn’t until a few days later that he responded. He was still the same sweet, funny, charismatic guy she had connected with, and she was happy to not get ghosted again. Even now, they still text here and there, or he’ll comment on her Instagram stories. For now, that was enough for her. But she was definitely looking forward to him visiting again… even if it’s not until next year.