Find out what his/her level of experience is, are they an anal sex veteran with years of experience or are they new to the game and out to increase their sexual awareness. Partners with different levels of experience often adapt “teacher-student” roles in the relationship, while those on equal levels can comfortably explore their fantasies together.
So the magic day has finally arrived, that person you have been getting to know online has agreed to meet in person.
This is especially true for men approaching women, as even openly sexual women can often be turned off by the mere suggestion of anal intercourse.
Are they dating other people as well, or do they prefer exclusivity?
These are real people with real feelings just like you, yes they do happen to have an interest in exploring their anal fantasies but likely won’t respond well to a blunt or crude first message.
An opening line (or in this case, an opening Wink) like “hey baby, you have a hot ass - I’d love to sink my dick between your delicious butt checks” will likely end your chances before you even get started!
Anal sex has had a long history of being “taboo”, a subject that “nice girls and guys” wouldn’t dare talk about.
In recent years this situation has changed, yet despite the growing popularity of anal sex in all adult age groups it is still not that easy to broach the subject when you first meet someone, either in person or online.