Would suggest the following.
Don't go too big too soon. I have play mates who can take my arm past my elbow up their arses. Not a nice feeling for me, and I'm sure in later years they will have a prolapse.
So, not junk food for 12-24 hrs before the session. Eat Weetabix or bran for breakfast. go to the loo approximately an hour before. Follow this, and there's no need for douching.
Use a nice lube like super slik, if nothing else it tastes nice. Try a finger, but covered especially if you use contact lenses. Personally I hate a finger because I've been scratched.
Toys, only use butt plugs (dildos with large flat bases), it'll save a trip to A&E.
Try a number of toys, maybe one a bit longer, thicker than a finger to start. DON'T ram the thing in. Present to the anus, push slightly, then allow long, slow breathing, and the toy will slowly enter. I never, ever push. The angle determines how much pleasure is gained.
If you're doing full strapon, don't get a harness with elastic, as it dulls the reaction time. I had mine made bespoke for me. Very soft leather, well sown, therefore with 10 years of strapon, still looks good.
Position is up to you, but easier for me as a short person, I have the guys generally on their backs so I can see if they are struggling, I can lube them and wank them, they can spunk over my boobs.
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