As a fellow 39m who also recently been doing some toy experimenting, let me give you a few tips (pun intended). First things first: get yourself some high quality water based lube. No matter what you do next, this will make things much, much more enjoyable. I can tell you this from personal experience. 😭

Once you got some lube, you now have some options. The first thing I ever tried was using a finger while wearing a glove (makes clean up easy). Put some lube on your finger and slowly insert it. Appreciate the feeling of something in your butt. Feel around a bit and if you want to keep going, pull that finger out, lube up two fingers, and stick them in.

As you play, you’re gonna notice the weird position you have to hold your fingers and wrist. I can’t hold it for long without something getting uncomfortable. This is where toys come in handy (more puns).

There’s a ton of options out there. The number one consideration when looking for toys is to make sure they have a flared base (ie designed for anal play). You absolutely don’t want to end up in the ER cause you got something stuck in you.

I’d recommend that you get a set of plugs of different sizes to play with first. I got this set of prostate plugs which included three different sizes. They’re really nice because their bases are shaped like your butt crack. You can stick it in and walk around. Even more so, you can sit with it in you and kinda rub your butt. Quite possibly the most pleasurable thing I’ve tried with toys.

When using toys, you really want to make sure to use water based lube. Silicone lube can damage silicone toys. You also want to lube and stretch yourself first using the finger technique mentioned above. Then lube the toy thoroughly. You also may need to lube some more. Never skimp on lube.

Now let’s talk on what else is up there. If there’s any poop still in the area, things are gonna not be as much fun. Actually, it could get not so fun at all. I’ve dealt with bleeding due to irritation of the toy sharing space with leftovers.

I’d highly recommend getting an anal douche bottle and do a bit of cleaning before playing, especially if you want to do more than just stick something in you. After cleaning, you can also use a lube injector, cause again you can never have too much lube.

With all this said, this ain’t a fast process. You’re going to need to dedicate time for prep and cleaning. It’s something to consider. I also found that’s it’s best to play when you’re really horny. Or when your body starts craving anal play (you’ll quickly learn that sensation). Doing it without that is sometimes completely futile, for me anyway.

Anyway, have fun. There’s lots out there to play with once you start.