Chapter Text
There were some things in a relationship that were easy to bring up, but this was one that Raylan had never mastered the art of doing with any kind of grace.
There was just something decidedly off-putting about the words penetrative sex, but really it was what he was looking to do. With women it was easy, at some point they got to the point of, yeah, I am looking for a dick, and most of the time, even when it was a one-night stand, that’s how it went.
With guys though, there was a lot more…planning that went into things. In fact, most of the one-night stands Raylan had with men, ended up in hand jobs, or blow jobs, unless they were offering to be the one on the receiving end of things.
It wasn’t a macho bullshit thing either, despite what Trey had tried to convince him before they broke up. It was that Raylan didn’t like it, not the fucking someone, the being fucked. Trey said all men did, and it was internalized homophobia. Raylan felt it was more that he had never bottomed for a guy who got him off, but given Trey had taken so poorly to the suggestion that he ended things with Raylan, there was no confirmation.
Most of the men he had been with had not been receptive to suggestions, and Raylan felt a lot more sympathetic towards women’s complaints about guys not being able to find their clit with a map the more he had sex with other guys.
The only advantage he had was that men also had dicks, and they usually knew how to handle them. Well except that one guy, and Raylan wasn’t sure if Max was a sadist, a masochist, or had some sort of sensation issue in his own dick, but that had fucking hurt.
So, Raylan wasn’t exactly volunteering to get fucked, especially as he was aware that Tim had not done this before, well, with a guy that was. Where Raylan was bi, Tim was gay but had wanted to be entirely sure before he committed, so the man tried having sex with women, which apparently had gone pretty badly. Since Tim had been in the army, sex with guys had been out, so Tim’s experience was mostly limited to covert hand jobs. While Tim had been out of the army for a while now, the man had a raging case of PTSD and letting someone fuck you was kind of a vulnerable thing, so he understood why Tim wasn’t willing to let just anyone do it.
It had come up early on in their relationship, back when the relationship was still, we work together but occasionally exchange hand jobs when we are hard up. It took over a month of that for them to make it to friends with benefits, and the benefit was this new level of relationships had put blowjobs on the table. Tim wasn’t experienced, but he was a quick study, and if it came to it, Raylan would be alright if that’s as far as they ever went.
The thing was, while Raylan was okay with them never going further if Tim didn’t want to, he felt like Tim wanted to, but wasn’t any more sure about how to bring it up than Raylan was. It made sense, Tim was a “try everything once” kinda guy, and it’d be odd if that didn’t extend to sex. It’s why Raylan knew that if Tim did agree to it, that he would offer to let Tim top, even if it wasn’t his own favorite activity.
Raylan wasn’t into sharing, and really, the main reason he was thinking about taking that next step was they weren’t just friends with benefits anymore, they were together. Tim called them partners, but that just made Raylan squirmy when he went on assignment with Dunlop, and boyfriends made him feel really old, because that was something kids said, and when the hell had he gotten old enough to call teenagers kids? Lovers just sounded stupid, so Raylan stuck with “together”, and Tim humored him, most of the time at least.
It turned out Raylan didn’t have to say anything after all, because Tim was right there with him. Tim didn’t broach the subject over dinner, or drinks, like Raylan had been thinking of doing. Nope, that asshole decided to mention it over morning coffee while looking through a file at his desk.
Raylan had no idea what the hell Tim was thinking, seeing as they were trying to keep this whole affair under wraps, and Raylan choking half to death on his morning coffee wasn’t exactly discrete. Especially when Art popped out to check he wasn’t dying. By that point Rachel had shown up, and the subject was dropped. The ice however had been broken, so when Raylan invited Tim for “drinks” they both knew what the topic of conversation was going to be.
So here they sat, awkwardly at opposite ends of Tim’s sofa like they were teenagers trying to make sure everyone could see they left room for Jesus.
“You know, if you want to fuck, choking me to death ain’t exactly a good first step,” Raylan said, and wished he could take the words back, because that was NOT what he wanted to say, not at all.
To Raylan’s relief, Tim laughed. “I admit, I had not thought that one through to the end.” Tim stopped, face going blank, then he bit his lip. “I just, I wasn’t sure how to bring it up, so I said it before I could talk myself out of it. Timing coulda been better.” The tips of Tim’s ears were red, and Raylan couldn’t see the man’s face the way he was looking down, but experience said his boy was blushing all over.
It was time to come clean. “I’ve been thinking ‘bout it myself,” he said, and Tim’s head came around so fast Raylan worried about whiplash.
“Really?” Sometimes Tim sounded really fucking young, and Raylan remembered how big that age difference really was.
Raylan let out a breath, because if they were going to do this, cross that line, then they needed to be able to talk about it. “Ya, I have. I, well, I didn’t want to pressure you into anything, and I wasn’t sure how to bring it up without it sounding like that… I didn’t think about causing a near fatal incident in the office though, so you got me beat there.”
Tim ignored the joke. “I, you know I haven’t done.” The man stopped, and gestured a little, before continuing, “any of that before, right? We never really talked about if you had.”
“I have, and before you ask, yes, from both sides. I’ve never really. I’ve preferred being on the top of things,” Raylan admitted, and then quickly added, “But, I get you haven’t done this before, and that might not be what you are looking for. We could start the other way, if you were interested in trying, and then, if you are okay with it of course, try uh the other way around? We don’t have to though, I mean, if you don’t want to. I am good with what we got.” One thing Raylan was sure of was that he absolutely did NOT want to lose Tim.
“I would like to try,” Tim started, and Raylan accepted that they were doing this, mentally bracing himself for what was going to come next. “I mean I want to try both ways at least once, just to know, you know? But I, uh, would prefer to start from the bottom.”
Raylan blinked. That he hadn’t expected. He wasn’t dumb enough to look a gift horse in the mouth though, and just then his phone rang, Art needed him at the office. The conversation stopped then and there. Tim didn’t bring it up again when Raylan got back, and Raylan wasn’t sure if he was happy about that, or not…