I came on here to ask the same question as the OP but found this thread before posting a new one.
On a punt earlier this year I had asked the girl to do a toy show for me which she got quite into. After a few minutes she told me to put a condom over my finger and put it into her bum. I did this - it took a little while to locate her hole and the feeling as it opened to accept my digit was very horny as was the effect it had on the girl who came spectacularly and then instructed me to fuck her which I did
This girl was a tourer who has not been back since but I would like to recreate it with a girl local to me. There are quite a few with Anal Play and Toys ticked on their AW profiles.
In members experience would most girls with those services ticked be happy with this scenario? I know the answer is to probably ask when booking but I sometimes find it difficult to do so despite having punted for 10+ years.