Deep Tissue massage is a combination of pin point and broad strokes in combination with other techniques to release tension and adhesions in deeper layers. It is applied to relieve musculoskeletal pain. Pressure can vary from light to deep and may be uncomfortable at times but not painful. It has sometimes been described as a "hurts so good".
Deep pressure is just that, deep pressure. If someone is having difficulty feeling my deeper massage applications it may be a sensory deficit and I will not work beyond what I feel is appropriate.