I'd say start with a training kit. If you get the right one you get the lube different size butt plug and a anal dildo to work your self upto
I’ve tried vibrating toys with my wife but she has always preferred dildos, large dildos. Heat up a nice big latex cock in hot water and she is squirming all over when she cums.
We went through a bunch of extenders and vibrators. When my wife liked sex we used the rabbit vibrator. I used it on myself more than she did. Some of the extenders felt real and made me feel like a man ( I am but am very small ). My wife thought all of them were too rigid. I still fantasize about fucking her with the extenders.
I’ve had a lot of toys, the fleshlight is probably one of the best. I was skeptical at first but won’t disappoint.