A few days passed and she inevitably heard from Craig again. She told him she was annoyed with how that night had gone down, and without actually apologizing, he was able to make her forgive him. She was notorious for lowering her boundaries and standards when charmed.
She realized that if she wanted to pursue this with him, she would just have to go in to this with an equal level of commitment. He wasn’t someone so important to her that she would want to drop everything and make herself available for him at any time. But if the opportunity presented itself that they were ever able to get together, she knew she wouldn’t turn it down. After another week of chatting, they both decided that they really did want to meet up. So again, they had to figure out when and where. They ended up settling on just getting a hotel room.
Now, there are two ways to look at that: one way would be to see it as a sleazy, Pretty Woman type thing. “No respectable girl would meet a guy at a hotel for sex,” is a phrase she had played over in her head more than once. On the other hand, she knew this experience didn’t have to be so “dirty”, and that it could actually be a really fun and exciting thing to happen to her. It was better than fucking in the back of his truck, that was for damn sure!
She was in control of the situation. This entire experience was in her hands. Craig told her he wanted her to be happy and gave her free reign to choose the hotel and the date. All he wanted to know was the address and the room number, plus her e-mail address so he could send her money for the room. Not in an sleazy escort way but in a fair, equal partners type way. So, it was up to her where they would go. She knew she wanted something nice, but she also knew she couldn’t go all out because she was definitely not flush with cash.
She ended up finding a beautiful hotel that was about a 15 minute walk from her work. She booked the room on a Sunday, and they were getting together the following Friday. She gave him all the information but then they didn’t speak for the rest of the week. By the Thursday she was sick of the anxiety she had been feeling so she sent him a simple, “hey stranger” text, to which he replied quickly. She confirmed their plans and even said, “just to be clear, this is a sleepover, correct? I don’t want to be paying all this money for a room for you to make me feel like a whore by leaving in the middle of the night.” He scoffed at the suggestion, and confirmed that he was staying over. Can never be too sure, though, so she was glad she had asked him.
When the day finally came that they were to meet up, she left work and went immediately to the liquor store. She knew she would need some liquid courage for the events ahead. Then she headed over to the hotel. She walked in and was impressed with the lobby’s marble flooring and high ceilings. She went to check in, and the man at the front desk offered her an upgrade with a nice corner view of the river. Yes, please! She finished checking in and headed up to the room. She knew Craig wouldn’t be there for another hour or two, so she had plenty of time to work out her jitters.
She opened the door to the room and was immediately taken aback by the gorgeous view. This was definitely not some shady, back alley tryst. This was classy! She changed out of the clothes she had worn to work and into just a tank top and leggings, something comfortable. She and Craig had been texting the entire time she had been there. Then, all of a sudden, he was breezing in through the door. A smile grew across her face immediately and her stomach felt a rush of butterflies.
The first thing he said was, “ah, I’m so nervous!”, which completely put her at ease. He was as weirded out by this as she was. He also couldn’t deny the connection they had built, either. She poured some wine into the complimentary paper coffee cups in the room (see? Classy.), and they sat down on the bed and talked for a little while. He caught her up on what he’d been up to lately, and he talked about high school as if it were yesterday. He even went as far as to mention that he had seen a different girl from high school on Bumble. “She’s still a smoke show,” he added. She agreed that that girl was obviously beautiful, but um, hello! Maybe not the right time to be talking about other women when he was about to have sex with her?! Men are so dumb.
Soon enough though, he kissed her and she was sure she was in for a good night. As the kissing progressed, she realized why she had gone down such a bad shame spiral after sleeping with Ginger Beard. She recognized that she wasn’t the type of girl who could just hook up with random guys like that. Sure, she had made out with countless guys throughout her drunken youth, but she hadn’t had sex with them. In her 30 something years, she had only slept with a handful of guys. She needed that intimacy that only comes with an emotional connection – a comfort level that she just couldn’t reach with someone she barely knew.
As hopeful as she was that this would be an amazing experience, that feeling didn’t last long. The sex felt great, they were both really enjoying themselves, but when they finished and he stood up, they both realized that she had just gotten her fucking period all. over. him!
So typical of her to have something like that ruin a good thing. Her period wasn’t that heavy and she wasn’t really embarrassed by it, but damn, such an inconvenience. Craig, however, was even less impressed. He didn’t really get upset or anything. He half-heartedly joked about it and he seemed fine. But immediately after he cleaned himself up, the energy between them shifted. It felt like they were just buddies now, not “lovers” (for lack of a better term). That was a huge bummer for her but she tried as best she could to ignore that feeling and continue to enjoy their night.
He had to go put money in the parking meter and they both wanted to smoke a joint. So, they got dressed and went downstairs. They realized they were both pretty hungry, as well, so they went for a walk to smoke their joint and find something to eat. As they walked, they talked about all sorts of things and she found herself getting more and more worked up by everything he said.
She fundamentally disagreed with literally everything he believed in. She found out he had lived in Florida for many years during his 20’s, which explained a lot about his twisted way of thinking. But instead of getting angry at him for all the dumb shit he was saying, the way he delivered all his absurd thoughts and opinions actually just made her laugh. He didn’t force or push his opinions on her, and was open to hearing her thoughts. Never wavering, however, from his backwards way of looking at the world. This back-and-forth banter created that sexual tension again though, so she was feeling better about how the night was unfolding.
After walking for a while, they realized it would just be easier to order Skip the Dishes from the hotel room, so they headed back. When their food arrived, they settled in at the small desk that the giant TV was placed on, and enjoyed their meals as they watched home reno shows on HGTV. It was so comfortable and relaxed. She didn’t feel nervous or anxious or insecure. It was like they had been hanging out for years.
After they ate, they were both so full and tired that they just climbed in to bed to watch more House Hunters, and whatever else was on. His breathing got heavier and slower and she knew he was falling asleep. She tried not to be upset, but fuck, they paid all this money for a hotel room, and they’re just going to have sex once and that’s it??
She knew it was because of her period that he wasn’t trying anything else, and she called him out for it. He really didn’t have an argument because he knew she was right. In his typical sweet, charming way, he pulled her close and they cuddled as he successfully brought her back down from her somewhat frantic and annoyed state. Still, she wasn’t letting it go and after some time had passed, she just took it upon herself to get things going a second time. This time was much better, and much less bloody. She got more out of the second go than she had the first time, and was finally satisfied. He was definitely not as in to it as he was the first time, but who are we kidding, he enjoyed it too.
It was already midnight at this point so she understood why he wanted to sleep now, but she was still wide awake. They talked and cuddled, and he told her how happy he was that they had finally gotten together as he gently kissed her shoulder. He also told her how beautiful she was, among other sweet compliments. Soon his breathing got heavy and he was out cold. She lay there in his arms, happy to be there, yet acutely aware she would be getting no sleep that night. She was definitely not used to sleeping with someone anymore.
And then it was morning. He had to get up to go do a flooring job. He offered to drive her home but there was no way she was leaving that hotel room at 8am. They talked a bit more and she apologized for her period, but explained that because of her infertility issues, she never knew when she’d be getting it. That seemed to make him feel better, for some reason. As if he thought she knew she was getting it but didn’t tell him, or something? It was still a bit awkward, but she figured it was because they were coming out of their sex bubble and back into reality.
Then he kissed her goodbye and told her to text him when she left. And that was it. He was gone and she had the whole king-sized bed to herself. She grabbed her leftovers from dinner and opened her laptop to immediately write up a rough draft of her night. She felt like a modern day Carrie Bradshaw. A couple hours passed and she got herself dressed and ready to go home. She texted him when her Uber arrived and he replied by “liking” her message.
She knew they wouldn’t be chatting for some time after that, but even two months later, she has yet to hear from him again. At first she was disappointed. How perfect would that have been if they had become Friends with Benefits? She knew him, she was comfortable with him, she trusted him in the sense that she knew he was Covid free and from what he had told her, she felt that he wouldn’t have been out hooking up with a bunch of other girls if things had actually taken off between them.
She knew he was grossed out because she had gotten her period, but then she got the sinking feeling that she herself turned him off. Like once he saw her naked he realized he had made a huge mistake. She hoped that wasn’t the case. She tried to tell herself it was just her period – he’s immature, he’s not worth obsessing over… And it’s not like she even wanted anything more from him than what had happened. Still, the stinging feeling of rejection pierced through her fragile little heart.
“Oh well,” she told herself. On to the next…