I originally wrote this article for my website dirtydianasdiary.com but it's a question I get asked A LOT so I thought I'd share it here on tuscl. It sounds like a simple question of etiquette but it's actually much more complicated. Here are the fine points.
Be clear about what you want. You want to be polite and respectful but not vague. Make sure that you know what you want before you start talking. Do you want a particular girl to meet you for dinner? Do you want sex? Do you want it inside the club or outside? Are you willing to pay her and if so, how much? If you are looking for sex, just say so. If you are paranoid about a law enforcement situation, you can use a euphemism like, "Do you do private parties?" or "Would you be interested in doing a dance outside the club?" The answer will likely be "no" but the question won't offend the dancer. If you're too vague, the dancer will assume you're just trying to ask her out and unless you're Ryan Gosling, she will be annoyed.
Be prepared to pay. A lot. You know what's insulting? Being undervalued. Do not offer her an insulting amount of money to leave the club and give you a blow job. Whether she would be willing to or not, at least show her that you would value the experience.
Maybe you're not looking for a blow job. Maybe you just want a little extra contact in the V.I.P. In that case tip her on the front end. Guys are always promising us more money if we "do more" and they are always full of shit. Tip her a $20 each time you see her on stage. Tip her an extra 30-50% of what the dance you're buying costs before she starts dancing. All women like to feel appreciated and in the strip club, money is how you communicate appreciation. If she feels like you appreciate it, she will likely give you more than the minimum requirement. Keep in mind that this is a gamble, and don't get pissed off if you don't get what you want. You don't have to keep buying dances from that particular girl. You can try someone else.
Pick an experienced stripper. Look for a dancer with a couple of years under her belt. You don't get an employee handbook when you get hired at the strip club so most strippers walk around clueless for the first little bit.
Don't take it personal. At most clubs I've worked at the girls are not allowed to do OTC dances. Even though lots of dancers do it, it's pretty taboo.
Keep that in mind and don't take it personally if the dancer declines to meet you anywhere but inside the club she works.
Don't be pushy. Women in general, including strippers, will do surprising things when they feel truly comfortable with you. You will never go wrong if you focus genuinely on making her feel comfortable and safe.
Men are from Mars and women are form Venus – i.e. we often see most things differently and often as far as 180 degrees apart – we are often wired differently thus process and view things quite differently.
w.r.t. “undervaluing a dancer” - let's say the dancers in a particular area or club will usually have sex for $300 (as an example) – for the dancers that do this all the time; they take $300 w/ no fuss; for the dancers that does it sparingly; she thinks she deserves b/w $500 and $1000 or else “she feels undervalued” - why is s customer going to pay 2x+ b/c the dancer thinks she deserves it – if there are other dancers willing to do it for the going-rate then why would a custy feel compelled to overpay in order not to make the dancer “feel undervalued” – i.e. when it comes to sex from dancers; a custy can get quotes from $200 to $1000; why would he choose the $1000 option if he can get what he wants for $300.
w.r.t tipping extra – it sometimes feels as if most dancers think custies have a stack of $$$ 4 feet high in their house – that we have unlimited funds and don't have responsibilities such as children; mortgages; car payments; college payments; etc – dancers come across as if a custy does not have a right to to hold on to his $$$ and spend as he sees fit – strip clubs are expensive as it is – lap-dances in most places are $20+ for about 3 minutes of entertainment that fly by – add to that overpriced drinks; cover charge; etc; and a SC visit is a big hit to the average guy's wallet (and most SC goers are average guys; not independently wealthy guys).
A tip is to be earned not paid up front ahead of time since you yourself mentioned is no guarantee you'll get any better service; thus the tip should be post-dances once the proper service has been rendered – most of us that have SCed for a while have gotten burned by a dancer at one time or another; so precautions w/ one's $$$ are def in order – e.g. a couple of weeks ago I struck up a convo w/ a custy at a local SC; he was relating me a story how he went w/ a dancer to VIP where they had both agreed to have sex – he gives the $$$ to the dancer and she bolts out of the room w/ his $$$ and the douchebag management said there was nothing they could do – I know I know – you are not that way and most dancers “are not that way” - ok – but it does happen - dancers trying to outright rip-off custies is part-and-parcel of the biz and thus why you don't pay upfront hoping to get a bone.
I find it interesting how dancers think customers should be as generous w/ their $$$ as possible – it strikes me as interesting b/c these same dancers often seem to be super tight w/ their own $$$ where many will flip if you by chance underpay them by just $5 – and many a dancer does not want to pay for shit in the club; they want drinks; food; cigarettes; etc; all bought for them; so they seem to have one view of a customer's $$$ (spend spend spend it all) and a different view of their $$$ (it's mine mine mine).
SCing is like shopping – when a woman goes shopping; she usually has a set amount she can spend or is willing/able to spend – thus she will not buy everything in the store nor the first thing she sees nor what a salesperson is trying to push on her – she will buy what she wants; when she wants; and at a price/value she thinks is fair – she will try to find the best value and not overpay. The SC custy is similar – he has a set amount he is able to spend and he will spend it on whom he likes and how he likes; not on the first dancer that walks up to him nor spend how a dancer wants him to spend it – dancers spend their $$$ how they see fit; so should custies in the SC.