As physical as my relationship with Shelby was, I’ve had the time now to look back and realize that’s pretty muchallit ever was. We never bonded the way Adrian and I have as friends, and we obviously didn’t want the same things or share the same values. But Adrian and I already have that connection. If I’m right that we could use that foundation to build a romantic relationship, I think it would be so much stronger than any other I’ve had.
And I already enjoy spending time with him more than I do anyone else. I’m sure that adding anything sexual would only increase our bond. Whether that means penetrative sex, or blow jobs, or even if we just end up making out like teenagers, I think that it would be enough for me to be happy.
All that being said, the idea of being inside of Adrian, or hell, even him being inside of me, sounds really fucking hot. And I have the beginners kit I ordered… so I might as well use it.
I had already opened up the kit and cleaned everything when it was first delivered, but as I pull it out of my nightstand, I realize I might need to relocate.
One of the things included in the kit is a douche, and if I’m going to do this, I want to commit. During my research, I learned I already follow a pretty bottom-friendly diet, but I still like the idea of feeling clean if I’m putting anything up my ass.
The instructions that came with it warn that you’ll need some time between the clean and any fun activities, so I only bring the bulb with me to the bathroom, holding it under an extra towel butnot exactly hiding it as I walk through the hall with only a towel around my waist.
It doesn’t matter though. It never does. Adrian always stays in his room for the night once he’s in there.
I brought my phone, too, and do a quick internet search, again, to make sure I don’t mess this up.I got this. Don’t use water that’s too warm. Do use lube to make inserting it easier. Relax. I’m so used to putting my body through hell for hockey, pushing myself through injuries, fights, illness, whatever I need to, to play. It’s all a mind game. This is just another thing to add to the list of potentially uncomfortable things I’ll go through to get what I want.
Checking that the water seems okay, I fill up the bulb, grab the lube from my shower, and position myself with one leg up on the toilet seat. Kind of an odd position but better than trying to stick my hand in the toilet.
I take some deep breaths, and then some more, just in case. I do feel pretty relaxed, so I carefully push the tip in. I’m not preparing for a colonoscopy here, so everything I saw online said not to go in too far, but even the smallest bit feels strange. Not bad, so I think the breathing and lube did their jobs, but definitely a new sensation for me. I’m very aware of it, so that’s probably in far enough.
The water is an even stranger sensation, but I continue following the instructions, holding it in until my body is clearly done. It said to repeat that a few times, but after one more round, I’m no longer feeling like this was a sexy, fun new experience for me, and I think it did what it was supposed to. My ass feels cleaner than ever. The rest of me though? Well, I’m ready to wash my entire body after being so focused on the toilet.
I’m supposed to wait anyway, so after cleaning the douche, I opt for a full-body shower, really taking my time to wash everything, even doing some light manscaping while I’m at it.
Feeling way more confident than I was before I got in the shower, I finally focus on why I was doing any of this in the first place. I want to be with Adrian, and I want to not seem like the completely inexperienced thought-he-was-straight-a-few-months-ago man that I am.
I don’t think he would judge me or anything, but I already feel like I’m waiting long enough with my plan to hold off until we’re no longer roommates. If the time comes, I want to be ready.
Thinking about physically being with Adrian has blood rushing to my dick again, and I finally feel like I’m back in the right headspace to use the other, hopefully more fun, toys that I got.
Back in my room, I lay down on my bed with everything out next to me and decide to start simple with my finger. I saw someone online recommend you begin with breathing exercises while working your finger in, then as you continue the breathing, to apply pressure rotating around your hole as you do to stretch out the different areas.
My dick is still hard, so I give it a few strokes as I start my deep breathing, feeling like I’m relaxing into the bed. I bend my legs up for easier access to my freshly cleaned hole, and lube up my finger. After teasing my hole for a few moments, spreading the lube around, on a deep exhale, I slowly push the tip of my finger in without any resistance and work on the rotating stretching out technique, glad that I have a plan and didn’t jump into shoving things inside of myself blindly.
Again, this isn’t some magical, new experience for me, but it’s fine, nothing uncomfortable. I continue to stretch myself as much as I can with my finger, going deeper as I do, until the whole thing is comfortably inside me. I could probably repeat that process with two fingers, but I think I’m ready for the first toy.
There are three silicone plugs, all different sizes to work my way up to the biggest one that’s almost as wideas my dick. Starting with the smallest, I add more lube, and I’m impressed to find my finger did its job because it goes in easily. I take a moment to evaluate how I'm feeling, continuing with my breathing, clenching and unclenching a few times.
It’s a good feeling, I think. I’m very aware of my ass, and nerves I’ve never really paid attention to are suddenly all I can think of. The feeling of being full is pleasant, and I quickly find myself wishing there were more. I wrap my left hand around my cock, tugging a few times while I try to focus on the dual sensation of jerking off while also having something inside me. The combination is surprisingly hot, the pleasure of both combining to have me already climbing toward release.
Fuck, not yet.
I back off from my dick, and add lube to the middle-sized plug before I remove the first. My hole clenches around nothing, and I’m immediately disappointed by the sensation of feeling empty. This plug is a little more work to get in, but I take my time, continuing with my breaths, and before long I’m enjoying a more intense fullness.
I definitely like this. My dick is really fucking hard now, straining toward my abs, but I continue to ignore it in favor of the plug. This one sits deeper inside of me, and as I shift my hips, mostly involuntarily at this point, I think my prostate is finally involved as the pleasure intensifies with each movement. There’s another plug to try out, but I don’t think I can wait—there’s another toy, a prostate massager that suddenly has all my attention.
It’s curved and rounded, and a few minutes ago, it seemed very intimidating, but now that the plug is inside of me, teasing me with random jolts ofholy fuck that feels amazing,I think I’m ready.
Feeling even more empty after removing this plug, my hips are constantly moving now, desperate for something to fill me upor touch my cock. It takes a second to figure out the curve, but having something back in my ass is a huge relief. I know there’s even more this can do for me now though, and I adjust the angle until I’m moaning loudly with how fucking good it feels when it finally rubs over that perfect spot.
How have I never done this before? I’m clearly in the group of people who enjoy having something up their ass, because this is the best solo session I’ve ever experienced, and I haven’t even finished. I’m being so obnoxious with the loud moans and whimpers escaping my throat right now, but I can’t find it in myself to care. I want Adrian to hear me. I want my sex sounds to be all he can think about as he falls asleep.
I finally grab my leaking dick, spreading the precum around the head before stroking the shaft as I picture what would happen if he came to investigate. Would he want to watch? Would he drop his pants and offer to show me what a real dick feels like? I’d be ready for him and more than willing.
My orgasm hits so intensely that I swear I black out for a moment, completely consumed by the euphoria.
My breathing is more labored than during any hockey game as I wait to calm down from that high. The whole sexuality label might still be confusing to me, but right now, as I think about how great that felt, the label of “bottom” is feeling like one I could easily embrace.
22
