AYQ: How Do I Ask. . .

“Hey ValleyScott, Need some advice Dude.  Been seeing this escort almost every week for the past two months.  She is hot. Solid 9.5 in looks.  And she is damn good in the sack.  But she doesn’t do anal and I really like it that way.  How do I convince her to let me f*** her in the a**?  Do I need to just offer a bunch of cash?  Any advice would help.” — AssLvnDude

Well, Mr. AssLvnDude, this is an easy question.  How do you get a Sex Worker to do something that she doesn’t normally do?  Easy.


Your question states that this provider “doesn’t do anal”, which means that you already have the answer.  The fact that you already know she does not provide this service means that either you read it on her website/ad/listing/etc. or she told you herself that she doesn’t do it.  Either way, you clearly know it.

To ask her to engage in anal sex with you would be rude.  To attempt to bribe her into it is down right insulting.  Now I am sure there are some providers out there who would go for it, but to attempt it is completely inappropriate.  If you are seeing her as often as you claim, then you have likely developed a certain level of trust with her.  To attempt to influence her to cross a boundary that she has put up would destroy that trust.  Don’t do it.

Now I am not saying that you cannot bring up the fact that you enjoy anal sex if you two are ever just talking about sexual desires.  If you are having a conversation about the things you like and don’t like, there is nothing wrong with being honest.  A conversation is a conversation.  But do not ask her for it.

So, to make this abundantly clear to all clients:  If you already know a Sex Worker does not provide a certain service or sexual act—DO NOT ASK FOR IT.  We clear?


If You Don’t Know

Okay, there is also the situation where you do not know.  Unlike Mr. AssLvnDude, you may easily find yourself spending time with a Sex Worker and not know what her “No List” does and does not include.  Can you ask then?

Yes.  But only in person.  And politely.

It is generally considering inappropriate to ask about services over the phone, text, email, DM, etc.  You go with the information that you have.  Once you are in-session, you can ask questions.  I find it is a very good idea to ask a lady about her boundaries once we are together.  Many ladies will lay out their rules for you very clearly once you are together.  And if you have a question, this is the time to ask it.

But here is the big rule: If she says no, it means no.  Her rules.  Period.  This is the way it goes.  If you cannot abide by a Sex Workers rules, then just walk away.  You shouldn’t be there to begin with.  

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