Sunday, August 16, 2026

Caleb/Rylee: Never liked pool parties anyway...

Hanging around the house getting used to being Rylee was starting to get a little suffocating, so when one of her friends reached out to hangout I decided “fuck it”. Even if the time to head out to college was coming soon, where I theorized that I could be a lot more myself without raising any eyebrows, it was still the case that sometimes I was going to have to be “Rylee” around people who know her more intimately. A casual hangout seemed the perfect time to practice that, so I sent the confirmation, made sure I looked presentable enough (still very tied to the “jeans and tee” look for now), and headed out.

With the lack of good teen “hangout” spots, we had agreed to meet up at some local sit-in restaurant and get some lunch. Heading inside, I spotted a girl sitting at a booth waving me down. Thank god for social media and caller ID having given me both the name and face to connect to this stranger. Her name was Grace, and from the photos I took it that she was a schoolmate of Rylee’s and fellow drama enthusiast. Plenty of pics of them from practice, messing around in costumes, that kind of thing. I think I had a couple inches over her, balanced out by her being a bit more curvy. And girly, sporting a nice summer dress and well maintained blonde hair over my androgynous clothing and simple ponytail.

“Wow, you look like a mess,” she says as I slide in across from her.

“Sorry, I’ve been, uh, packing for the move,” I say, giving the best excuse I could think of for why I was dressed down.

“Uggh, don’t remind me,” she groans. “I can’t believe we’re going to be split up. But you know my parents, wanting me to keep up the family tradition of…”

And that’s how things went for the first few minutes, exchanging complaints about the whole college experience. If I hadn’t been the one in Rylee’s shoes right now I’d feel bad for two friends getting split up over silly things like alumni status and such, but being her I couldn’t help but feel a little glad that it seemed Rylee was the only one of her friend group heading to the particular college she was in.

“Anyway, I think I got the perfect idea of how to forget about it all, at least for a little bit. If, you know, you’re up for it,” Grace says, eyeing me warily.

“Shoot?”

“Well, Evan is apparently holding one last pool party at his house before everyone splits up. If you don’t want to go though I’d totally understand.”

I still haven’t exactly gotten over my aversion to wanting to be in a swimsuit, but seeing as Rylee did have some conservative enough one piece suits and I was really starting to feel the cabin fever, I figured if I wore some shorts and a top over it and went in if I felt like it I could probably make it work.

“Yeah, I got no problem with it. Sounds like fun!” I say, digging into some of those exercises to try and up-regulate myself into sounding actually excited.

“Wow, good for you! If it was me I’d totally avoid going to a party my ex was throwing.”

That threw me for a loop as I did not, at any point, recall Rylee mentioning an ex. I could already feel the awkwardness of having to navigate that situation, but I couldn’t back out now that I had agreed to it and gotten praise for it.

“Pfft, yeah, of course. We’re all adults now, right? We can stay friends and hangout and stuff,” I say to save face.

Once I got home, however, I immediately started texting Rylee wondering who this Evan guy was. The response I got back felt a little dismissive:

Yeah we broke up a couple months ago cause going to different colleges.
It was mutual so should be cool, don’t sweat it!

So that was the situation when the weekend arrived and it was pool party time. I ultimately chickened out of going for a swimsuit. Even with a one piece, I still wasn't quite feeling up to it. Perhaps having had high school friends gawking at swimsuit issues or girls getting in and out of the pool while bothering me for my opinion on things had just soured the idea of swimming like this in general. Still, it was hot enough outside I had at least relented to wearing a pair of shorts and a white tank-top. That by itself was fine, but the decision to go without a bra, thinking it would be more comfortable, would in retrospect be a bad one...

I had been hanging onto Grace as a social life line for the party at our little station at a poolside table. She had been facilitating most of the conversation with the rest of Rylee’s friends and acquaintances as they filtered through, my chiming in only when I could comfortably say something about college worries or some random bit of pop culture I recognized. My age gap with Rylee was small enough that we theoretically would have similar spheres of recognition, the gender and personal preferences being the main thing keeping me unaware of some of what got brought up. 

Still, I must have been giving a bit of a vibe of not wanting to be bothered as it was all quick, and most people eventually let me be there in presence even if I wasn’t talking much.

Eventually, though, he made his way over to us and…look, even as a guy I could appreciate on an aesthetic level if a guy was handsome. Dirty blonde hair, white teeth, a physique fully in line with his status of a student athlete (think Rylee had said basketball), and in just his swimming trunks he was making sure everyone was seeing it. Magnifying the effect was the glistening of water dripping off him, a quick run of the hand through his hair to get the excess out managed it leaving it a mess of curls.

Point is, he was out, he knew it, and I was not appreciating the warmth in my face that was starting to creep in as I watched him approach. 

“Glad you two could make it,” he says as he takes a seat across from me. While he said two, the way he looked at me made it clear he meant he was glad I made it.

“Y-yeah, of course, wouldn’t have missed it for the world,” I spit out as my mind races to figure out why all of a sudden I was feeling warmer. Had to have just been some kind of residual memories of Rylee’s body’s feelings towards him or something, right?

I did my best to not look like I was drooling over him no matter what Rylee’s body wanted to do, but it was eventually clear he must have noticed. Directing the conversation towards me, attempting to playfully touch me, eye contact. If Rylee was under the impression he was over her, I’m pretty confident in saying she was dead wrong.

“I, uh, think I’m going to get me some more soda,” I eventually say, wanting the excuse to leave the conversation.

In my rush, however, I didn’t notice another partygoer coming by, and in a sitcom-esque loss of balance I found myself tripping into the pool. Quickly surfacing, I glance down and see that the choice of white tank-top had been a bad idea. As soaked as I was, it was turning translucent, and with no bra or swimsuit to provide a second layer of coverage...

Grace and Evan were quick to act, getting a towel and helping me out of the pool before escorting me into the house and into the bathroom.

“I’ll grab some clothes from my sister’s stuff. I think you’re about the same size,” Evan says as he shuts the door, leaving me to dry myself off.

As I was just finishing getting undressed and starting to dry off I heard the door open. Thinking it was Grace, because who else would it be, I turned around, having just finished drying off a leg, and gave the clothes-handling Evan a nice flash of…well, everything.

“What the fuck dude!” I yell out as he quickly shuts it again with a million apologies.

“Sorry, I did not think you’d get undressed that quick,” he says from the other side of the door. “Though let’s be honest, it’s not like you showed me anything I haven't seen already.”

That froze me in my tracks.

I guess it should have occurred to me that Rylee and Evan, both being perfectly healthy, attractive, likely allosexual teens and dating meant they likely would have had sex. Considering my personal baseline, however, it had just never crossed my mind, and now that the fact Rylee's body was up for it was something I wasn't quite mentally ready to process half-naked in a stranger's bathroom.

“Oh shut up, Evan, and just let me handle this” Grace says, shooing him away from the room entirely before politely opening the door a crack and handing me the change of clothes Evan had brought.

Once I was ready I gently opened the door and peeked out.

“Don’t worry, it’s just me. Can’t believe he pulled that shit. I mean, he’s usually a nice guy but guess even he has his moments of stupid boy brain,” Grace says, giving a death glare to the door as if trying to telepathically fry Evan.

“Yeah, well…yeah,” I say. In my head I had thought of maybe making some kind of quip or whatever. Rylee felt like the kind of self-confident and theatrical person to respond to faux pas like this with a quip to reassert herself. Perhaps I was going to need some improve classes or two cause I was coming up blank. Even now, writing this up, best I could figure out was maybe something about how for bragging about seeing anything he still couldn't get my sizes right cause his sister's clothes were just a little tight.

After that, the rest of the party didn't really matter. Evan gave his apologies again but otherwise kept away, I mingled a bit more with the rest of Rylee's friend group and took the appropriate pictures for the social media, and then we left. 

What does matter, though, is the implications of it all. 

Having read through the blog, I know it’s pretty much the case that whatever body you end up in you eventually start to find yourself sharing the original person's sexual tendencies. Maybe not in the exact preferences and such, but the overall orientation. Kaitlyn made some comments about how it relates to a biological basis for orientations and such, but, I don’t know, I guess I still had it in mind maybe it’d just be a thing I wouldn’t have to worry about? After all, sex was just a thing that never really interested me as a guy, but even I have enough awareness to know that the way my body was reacting to Evan, well, it definitely had a curiosity about the idea.

Then again, it all could have just been a one off, a remnant of the fact that this body had been intimate with Evan’s. Once we’re off at completely different colleges I can just hunker down on making sure I don’t screw up classes and I won’t ever have to worry about this stuff again, right?

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