I find strap-on play hot and sensual in videos but I am not into stuff like FTT, TT or SP. Also I ain't sure if I will like strap-on in a real session.

Is there anything I can try myself before going into a session? I don't wanna find out during a session and ruin the experience.

Buttplugs that dilate. Use lots of lube!

Good advice.
That's the process I use and I get top reviews for cleanliness from my strap-on Dommes.

If you're unsure whether you'll enjoy strap-on in real life, try playing with yourself. You can use your fingers (clip your nails!) or buy some small toys. For the cheaper toys I recommend you use a condom, as sex toys are not regulated and the inexpensive ones are not necessarily made out of bodysafe materials. Also, easy cleanup if you have an oopsie on your butt plug.

Great advice and tips. Also I want to avoid any exchange of bodily fluids when visiting a domme/escort for this. What steps should we take to avoid this? Are there any other health concerns?

Thanks. You have an awesome website and list of activities to try. Also liked the intro video. Will plan to visit Atlanta Dungeon sometime.

Looks like people are suggested a bunch of reasonable things: try putting things in your butt first.

I didn't read everyone's comments so if I repeat someone that's the reason.

- know that the strap-on porn clip you see is not at all what your first experience will be like

- you can have a pro start you with training or you can do it yourself

I just finished a little intro guide to anal play, which may help you:

https://bdsmlog.mistresstissa.com/a-bit-about-anal-play/

Thanks for the article Mistress Tissa. I will check it out.

To check how it feels, I tried using this. I wasn't able to get it in. Maybe it is too big. (Note: Didn't get an actual toy as I didn't want anyone to find out what I am trying to do)

This is an excellent primer. In my many years of sessions I've never really been a fan, but I've had some funny experiences. As a college kid in my second session the legendary Mistress Belle de Jour ordered me to be a training sub. While I was worshipping Belle's fingers (yes, fingers) she was barking orders to the trainee on how to put a tampon up there. It felt like I was about to have a movement. Anyway, after a while the trainee was dismissed, Belle and I did roleplay which distracted me from my discomfort. At the end Belle told me, "Don't take that out until you get home!" I disobeyed when I freshened up in her bathroom, wrapping up the tampon and throwing it away outside.

A year or so later I saw an ad for roleplay. I called and mentioned the "Amazon/jungle" thing and this other Mistress loved the idea. When I got there the Mistress said the Amazon would "rape" Tarzan. Naively I thought I was to be the Mistress' stud. But as the session unfolded I was on the receiving end, being taken digitally... with that same uneasy feeling that something was going to come out. Anal was off my list.

Fast forward to a few years ago. I caught up with a Mistress I've known off and on for a couple of decades. She seduced me into worshiping her strap on orally (with all the precautions). She always wanted to take me "inside out" as she put it and one day took matters into her own hands without much warning. She did it digitally, nice smooth strokes... Soon after I bought my own butt plug and she's used that on me on occasion. But that's as far as I can go. At my age I'm not too flexible down there.

Oh that's a new and interesting DIY kink pervertable: a wood curtain filial!

I suggest you start with not even putting something in your butt, as I explain in my article. Then once you're ready start with something small, like a finger.