There are far too many aspects of cupping to cover in this one post so I will be focusing on vacuum pump cupping and fire cupping. Many look at this as a completely safe activity but keep in mind that it was a medical procedure long before it became a kink and can have many negative side effects and ramifications. First and foremost is it should not be done on pregnant women without a good understanding of acupressure as it can induce labor. Adhere to SSC (Safe Sane and Consensual) Practices and utilize RACK(Risk Aware Consensual Kink) practices. Understand the risks, discuss them with your partner, and make certain it is understood and consented to.
Mechanical vacuum cupping is probably the easiest and safest to get started with even though there is specific equipment

Fire cupping doesn't create as much suction but is much more dramatic to watch. This one is fraught with dangers though and a firm understanding of fire play techniques, safety, and protocol is highly recommended before you try this. Make absolutely certain that all of the dangers inherent to fire have been addressed before starting this procedure.
Instead of using a vacuum pump, a vacuum is created by air (heated by fire) in a glass cup placed flush against the recipients skin. As the air cools in the cup, a vacuum forms that pulls up on the skin, stimulating the desired effect. There are several ways of heating the air in the cup with fire:
- One can swab rubbing alcohol (70% or 90%) into the bottom of a cup, then light it and place the cup immediately against the skin. By creating the seal the immediate loss of oxygen puts the fire out, preventing the person from being burned. The smaller the amount of alcohol, and the quicker the flame is extinguished by application of the cup, the better, so long as there is no risk of the cups falling off due to lack of a proper seal.
- One can hold the cup inverted over a flame (e.g. a lit candle), heating the air, then place the cup immediately against the skin. Care must be taken not to heat the glass itself. Even so, the person to whom the cup is applied will feel distinctly more heat than in the previous method.
- One can ignite a flame with a small alcohol-soaked cotton wad resting on a small pad of leather or other insulating material that rests directly on the recipient's skin, then place the cup immediately over the flame, putting out the fire. The quickness with which the flame is extinguished depends on the size and shape of the cup.

Baby oil massaged onto the skin first causes a better seal to form, making it possible to use this technique with less heating of the cup. It is often possible to slide the adhered cup around on the skin, preserving the suction seal as it glides. Care must be taken not to move the cup over protruding moles, skin tags, scabs, etc. This can prove to be an interesting sensation.
The longer a cup is left on, the more of a circular mark (like a hickey) is created. The skin pores are more open, and the patient may have a feeling like sunburn. There are, of course, more techniques and ways to apply this. Which ever way you choose to play, make certain it is as safe as it can be made and that all risks have been assessed. Surprises with fire are never a good thing.