oh my GOSH!!!!!
First some context – in general I’m an impatient, stubborn person so when I’ve tried solo anal play over the last four years, I haven’t really felt anything that unbelievable. Sure, having something up my butt when I came felt better than usual, but it was it really worth the extensive cleanup? For me, the answer was no.
So despite owning both a prostate massager and dildo, they rarely saw the light of day. Now, that doesn’t mean my thoughts and desires had changed. I’d get extremely horny reading this sub and hearing others describe the most unbelievable orgasm of their lives. I would try on and off many times to no avail, and had all but sworn off anal play.
That is until yesterday. With my girlfriend out of town, I was edging for a couple hours when I wandered over to the sub. I started to read some recent success stories, all of them preaching getting to the right state of mind, focusing on the pleasure, and not touching your penis.
With no threat of being walked in on or caught, I decided I was going to give this a fair shake and really do it properly. I got all set up in bed, towel down, prostate massager/dildo out with condoms, lube and headphones. Now one thing I did differently than other times was I wore a thong (my own, I just bought it) so I wouldn’t be able to touch my dick. I pulled it to the side when it was time to start playing and had no issues.
Now with my favorite sissy hypo video playing, I was all ready to go. I started with a finger to warm myself up and for the first time ever, finally felt my prostate. I was obviously really excited but remembered to take it slow, enjoy the pleasure. After that I moved onto my prostate massager, which felt good but nothing crazy, though I did start to suck on my dildo at the same time to enhance the mood.
Then came the dildo. My dildo is quite big at 7″ but I was feeling really good and determined to take it. I rolled the condom on and started on my back but quickly moved to riding it. And let me tell you, riding it felt INCREDIBLE. All of the sudden, I felt these sensations I’d never felt before. So I just kept going, moaning through what was an amazing wave of pleasure. It was at this point I began to feel my dick twitching, so I decided to take it out and play with it. And when I jerked it, I couldn’t cum like normal. I would get to the point of no return and feel these unbelievable things from the dildo. Cum would start flowing out of my cock but I could keep going.
I came about five times, with the last orgasm being on another level. I was absolutely spent afterwards and must have stared at the ceiling for what felt like forever. This time, the cleanup was absolutely worth it.
I’m already thinking about the next time I can do this! I’m so excited to have finally gotten here, especially when it felt like I never would!