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Approach a new contact like you would any new person you meet, online or offline.
This can create problems, especially if one partner is fascinated by the idea of anal sex while the other is either opposed to it or scared of trying.
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.
Since you don’t know this person yet it may be wise not to interject humor into the message unless it’s obviously meant to be funny, while humor can often be useful in breaking the ice it can also backfire if the recipient takes it the wrong way.
Once you have established two-way contact with a new partner the next step is often an online chat, sites like Anal Dream Date have a feature that allows you to do this safely without revealing any personal information.