Thursday, October 29, 2026

Caleb/Rylee: Living Truthfully in Extraordinary Circumstances (Part II)

Let’s rewind a bit from before the start of my last post.

Paige and I were at the gym doing a cool down run as I relayed the events from my card tournament “date” with Joshua. I had expressed my ambivalence about going any further with it, being a little vague about the details of why. Paige, of course, seemed to think things were easy.

“Just do it, what’s the problem? He’s cute, he’s available, and clearly into you if he went out of his way to indulge in your nerd hobby. Honestly, surprised it took this long for him to make a move on you. Practically glacial paced compared to everyone else.”

Yeah, apparently theater people worked fast. It hadn’t taken long before our theater major cohort became a complicated network of relationships. Most of it has just been some hook-ups, a couple developing relationships, and I think there’s at least one poly throuple in there somewhere of two guys and a girl (lucky her?). As one of the few straight guys in the musical theater concentration – which isn’t 100% gay but, like, it’s definitely a higher percentage than the normal population – Joshua apparently had been approached by some of the other girls. Made me feel kind of bad about apparently holding out for me.

Still, just because everyone else was horn dogging it through the start of the semester didn’t mean I had to, at least that’s what I thought.

“Didn’t realize class was meant to be a dating show,” I snarked back.

Paige just offered a shrug.

“I mean, it’s not, but put a bunch of horny extraverts together and it’s only a matter of time till people take advantage of it. The tight clothing and physical intimacy of some of those exercises totally doesn’t help.”

“Yeah, well, not sure I’d describe myself as either of those things.”

At least, if I was in my regular body I’d be confident in saying I was neither horny nor an extravert. While Rylee’s body wasn’t unbearably craving sex, the feelings I was having and the, uhm, dreams that had occurred at times suggested that it was at least open to negotiations about it. I also didn’t feel as tired dealing with people for prolonged periods of time as I did before either, though I wasn’t exactly making myself the life of the party like Rylee’s journal entries suggested she liked to be. If I was Kaitlyn I’d probably go on some kind of tangent about nature vs nurture here, but point is my certainty about my identity was still rather loose as my mind and body kept trying to find a new baseline.

“Still, sounds to me that there’s at least a little spark there, so hey, why not?”

“It’s…complicated. Like, I’m just really having trouble envisioning myself with a guy.”

She raises an eyebrow, and remembering there were lesbians in our cohort I clarified.

“I mean in a sexual way. I’ve dated guys before.”

Well, Rylee had, at least. As Caleb I was romantically drawn to women, but so far I can’t really say that had carried over to Rylee.

“Oh, so are you ace or something?”

“Probably not. There’s, uh, feelings there but not sure I really want to pursue them?”

“Maybe demi, then? Or maybe you just like taking it slow. Not everyone’s a Mia and Naomi after all.”

Two girls from class that had hooked up literally the first week of school and got a dorm room switch approved of right after. People were already joking about them being the college equivalent of U-haul lesbians.

“Point is, sooner or later I’m sure Joshua’s going to expect that if we’re dating he’s going to get something out of it, and I’m not sure I really want to deal with that right now.”

“Easy then, just tell him you want to just be friends, duh.”

“…yeah, I guess I could try that.”

At least, that was the plan till my conversation with Dr. Price, which leads us back to where the last post ended.

“Ok, just one date isn’t going to hurt anything. You got a body that wants this, so why keep fighting it? Just experiment a little?”

While I had the courage to do so, I texted Joshua if he was up for that dinner he owed me tonight – admittedly relying on the fact that there was now a new 42 card banlist to talk about as an excuse. I had barely finished hitting send before getting confirmation he was totally up for dinner. Clearly he was excited.

“God I hope this isn’t a mistake,” I muttered to myself.

Wanting to lean into the idea of this being an actual date, I tried to throw together something nice. There was this kind of sweater-dress thing in Rylee’s clothing, with a belt to help show off the waist. It had apparently thrown him off a bit as he did a double take to confirm it was me when we met up. To be fair that was basically the first time he’d ever seen me in anything that wasn’t jeans and a t-shirt or workout clothes. Funny it got such a reaction out of him when, in terms of showing off skin, it was still more clothing than what I wore to class. Guess context means a lot.

“Just, you know, figured I’d dress up a bit when you’re going through all this trouble to take me to such a classy place,” I say, giving a smile and getting up next to him, trying to initiate some physical contact as we start walking.

“Yeah, it, uh, looks nice on you,” he said, apparently a little unsure of how to handle the situation at hand as we headed towards a diner that was just off campus.

Which, to be fair, I think was totally on me. It’s easy to say you’re going to just try and go with the flow and follow what your gut says, another to actually do it. Even if I knew my body could get excited about Joshua, I had figured that to get myself mentally in line with it I needed to try and fake a little excitement and energy. You know, act the part of the girl looking to get with a guy and, well, we all know how bad my acting grades are. I’m sure he could sense it as we chatted through dinner, laughing a little more at what I presumed were his jokes or leaning forward a bit to tighten the dress and make my chest look more prominent. I’m sure the more experienced guys-became-girls from the Inn would get a nice bit of nostalgic cringe looking at me try and figure out how you flirt as a girl.

Still, we got through the dinner ok enough, but when we started the walk back to campus and I tried cuddling up again he finally spoke up.

“Hey, uh, can we talk for a second?” he said as he backed away from me.

“Let me guess, I was coming on too strong?”

“Yes? No? I mean, don’t get me wrong, I was hoping eventually you’d try coming on to me, but like the vibes were just kind of weird, like you were forcing yourself to do it.”

“Yeah, guess you see why I got a C+ for the acting midterm,” I say, trying to defuse the tension a little. “But, I mean, I do like hanging out with you, and I know you’re into me so, I don’t know, I figured I was obligated to at least try and see if I was into you like that?”

“…I mean, are you into me?”

I look him up and down, taking a pause at his eyes, a mix of confusion and desire.

“I…don’t know? Look, I just got some hangups around dating and sex right now and – “

“Whoa, hold on a moment, I didn’t say anything about wanting sex.”

I just give him a flat look. Even as an ace guy, I was still around other guys who weren’t. Sex was definitely something most of them were quite adamant about desiring.

“Ok, so I wouldn’t have been against it either, but it’s not any fun if you’re not into it. So, like, don’t feel like you got to throw yourself at me just to keep me around to talk nerdy card shit. I can live with keeping things slow, or even just being friends.”

I cross my arms as I think, keeping them low to not boost up my bust.

“Yeah, I think I’d rather stick with just friends if you’re fine with that. I’m just trying to work some stuff out right now, and like I guess if I had to fool around with someone I guess I’d pick you- “

“Wow, super flattering endorsement,” he said, clearly find it more amusing than an insult.

“Oh shut it. Point is, I got some shit to work out, and I’d be hesitant to throw myself at any kind of guy. But who knows, give it a few months and maybe I’ll be cooler with it, I don’t know. It’s a weird deal.”

“Well, hey, if in a few months you want to upgrade to friends with benefits or something I won’t complain, but don’t be surprised if in the meantime I get snatched up by someone else,” he says, giving me a smile and a self-confident wink.

“Hey, if you do, glad you got laid. No point hanging around for me if someone else calls.”

Honestly, it would be a whole lot easier if he just hooked up with someone else instead of waiting on some Trading Post Inn victim to sort out their gender and orientation dysphoria. Maybe I could throw him Sydnee’s way or something?

“Anyway, sorry to make the night all weird. Was trying to follow some advice Dr. Price gave me about loosening up and just going with my gut instinct more often. Since I thought maybe there was something between us it was worth trying but guess still couldn’t quite override whatever nonsense is going on in my brain right now.”

“It’s cool. I like that you try and think about stuff instead of just winging it.”

After that, the rest of the walk slid back into random small talk about Halloween plans. Paige was going to be dragging me to some off-campus party. Since it was open invite I gave him the details, figuring maybe he could find someone to hook up with there to help assuage a little bit of the guilt I was feeling, and we called it a night.

So, yeah, all that anxiety ended up just leading nowhere. It’s probably for the best. As much as this body’s making me feel sensations I’m not used to, at the end of the day I’m still me. I’m sure given enough time some kind of equilibrium will be established, and I’ll actually want to try and experiment a little, but for now just going to go along for the ride.

- Caleb/Rylee

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