I got up early, way too early on Sunday. I had to drop Tripp off at the airport. It’s his first post-pandemic flight. I got up at the ungodly hour of 5:30 am to take him to the airport. In the past, when he had an early flight, he’d take an Uber, but you can’t get one anymore, and if you can, it’s ridiculously expensive. I don’t know why he booked such an early flight on my one day to sleep in. I’d say that was most inconsiderate, since he didn’t actually have to be there until the next day. Everyone who knows me knows that the thing I hate most in the world is getting up earlier than I have to. I have it timed to get up for work at the last possible moment to arrive on time. He should know better.
Anyway, I found myself with oodles of time on Sunday that I otherwise wouldn’t have, so I decided to put it to good use. After a good clean out and a shower, I set out all the toys, both the commonly used ones and the aspirational ones, made up a fresh batch of J Lube, opened a fresh bottle of poppers, and got busy. You see, I have a goal, and the fact that I both got up exceptionally early and that I had the house to myself made it easy to spend most of the day stretching my hole. My goal is to be able to take a fist again. I haven’t done that for years, and my ass has gotten tight. It’s not like riding a bicycle. Actually, it kind of is, because I rode a bike for the first time in 25 years not that long ago and it took a while to get my balance back and my ass hurt for days afterwards.
The reason for having this goal is…. I “met” someone. I use apostrophes because we’ve only texted, but we do have a date soon. He is a very Dominant Top, very handsome, whose kinks match mine almost one for one. He’s also a fair bit younger than me, but that doesn’t seem to bother him. He thinks I’m hot. Let me tell you, he is fucking hot. He is way hotter than I ever have been. He’s into gear, boots, impact play (I’m dripping already), and fisting. I want to please him, and I want him to be able to fist me if he wants, hence the week long plan to get back into fistability before our date this coming weekend. I know nothing may come of this, but if it does, I want to be ready. I’ve been more than a year without a Sir now, and that’s far too long.
I set out all the toys I planned to use, from the smaller plugs and dildos, the medium sized items, and the fist sized ones. I spent several hours stretching my hole. I also used my speculum, which is kind of difficult to use solo, but stretches me like nothing else. It opens up progressively larger and larger and it’s an awesome stretch. After some time with that bad boy, the bigger toys started going in more easily. Finally, after going larger and larger, the biggest plug slid right in. At that point, I started on the fist sized dildo. It took ages, but I’m happy to report it eventually went in.
After that, I went to Tripp’s dildos. Tripp used to be able to take a small SUV in his ass, and his toys are seriously large. I didn’t think I would be able to take one of them. With an extraordinary amount of lube, porn on the TV, more poppers than should be legal, and taking it slow (slow, slow, slow), I got it in. It hurt like a motherfucker. I was crying, but I was determined. As it slowly stretched me past anywhere I’ve ever been before, and as the massive dildo slid passed my prostate, I came. I came so hard, I think I may have passed out. The combination of pain and pleasure was overwhelming. I had absolutely no plans to orgasm, and I wanted to save it for my potential Sir, but it happened. I’ve never had something hurt so bad and feel so good at the same time. It was mind blowing.
I plan on spending a few hours each evening this week making my hole pliable again. Even if nothing comes from “meeting” new Sir, I miss being the type of sub with an easily used ass. It’s not been easy. As I get older, my body doesn’t cooperate quite a nicely as it used to. As they say, practice makes perfect, and I need a lot of practice. At least I have the time, an empty house, and a possible new Sir to motivate me
Stay safe and stay well.