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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.
Approach a new contact like you would any new person you meet, online or offline.
Send out a first message that simply introduces yourself as someone who finds them interesting.
While the latter situation can be dealt with by openly communicating and gentle persuasion, the former can drive a wedge between people and can result in the decline or even the outright ending of the relationship.
When one partner harbors a desire that the other one refuses to fulfill it can only lead to bad things - frustration, cheating or even break-ups.
If you find you are both looking for something different you will probably want to move on, but please don’t be rude to the person - she/he has feelings too, and it is courteous to at least leave on a friendly note.
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.
Talk like you would on a real “date”, start off chatting as if you were meeting over a cup of coffee and getting to know one another - which in effect you are (minus the coffee).
It’s important to find out at this stage why your new sex interest has joined a dating site.
Wish them well in their search for someone, they will likely extend the same wishes to you.