Drain your swimming pool by opening the drains and pressure-relief plugs. Your pool owner's manual will tell you where on the pool surface to find these.
Clean the swimming pool using a mildly abrasive powdered cleaner. Sprinkle the cleaner on the plaster, then work the cleaner into the pool surface with a wet, soft-bristled scrub brush. Rinse the pool with water to flush the cleanser.
Sand plaster that's peeling before you paint the pool. If no plaster is peeling, skip this step.
Prepare an acid wash to clean the pool. A 1,000-gallon swimming pool typically needs 2 gallons of muriatic acid, dissolved in water. Follow the ratio on your pool-cleaning product to dilute the acid with water. Sprinkle the acid solution on the pool surface, scrub the solution into the surface of the pool with the scrub brush, then rinse off the acid. While you perform the acid wash, leave the hose running so that acid water being washed into the drains continues to flow out of the pool.
Clean the pool with a trisodium phosphate cleaning solution to remove any last traces of the acid. Use 1 cup of trisodium phosphate per gallon of water.
Let the pool dry to the touch before continuing.
Stir the pool stain with a paint stirrer. Paint the top edges and corners of the pool -- anywhere you cannot access with a roller brush -- using a 3-inch-wide bristle brush. Work your way around the edges like this.
Pour the paint into the roller tray. Fit your paint roller with a 9-inch-wide, half-inch-nap paint roller. Roll the roller in the paint tray to coat it with paint.
Paint the plaster using the roller. Work your way from one end to the other to apply a thin, even coat.
Wait the recommended drying time, as indicated by your product. Apply a second coat in the same way, then again wait the drying time. Apply a final coat if needed.
Let the pool stain set the recommended cure time, as indicated on your product.