Chester Mainard's Anal Massage on a Woman

Chester and Leila prepare for an anal massage session. Leila demonstrates several comfortable positions. Chester stresses the importance of communication and including full body touch.

“If I had only five minutes to get someone as deeply relaxed as I could, it's right around the sitz bones where I’d do the massage.” Chester Mainard

Chester shows us how to find the “resilient edge of resistance,” where the most relaxation and pleasure is available.

Never underestimate the pleasurable effects of simply holding still.

“Goosebumps and deep breathing is a good combination.” Chester Mainard

The anus likes a variety of strokes, including vibrations. Chester demonstrates the use of a towel to catch drips of lubricant.

Keep the massage alive by varying touch: stretching, holding, vibrating, gliding, stroking, and pulsing.

Chester demonstrates strokes for stimulating and relaxing the anal sphincters.

“I think it’s a good idea for them to want you inside for a long time before you get there.” Chester Mainard

Putting pressure on the anus without entering can be highly pleasurable in and of itself – or a great tease for what’s to come.

“If I go inside, it's because she opened to let me in, not because I pushed.” Chester Mainard

Chester demonstrates graceful and pleasurable penetration of the anal sphincters. Learn how to use your partner’s breathing as a guide to penetration and how to use anal clenches to deepen relaxation.

“Let your partner breathe you in.” Chester Mainard

Anal massage can involve simultaneous internal and external stimulation. Chester demonstrates the possibilities of kneading, tapping, and stretching other parts of the body while continuing internal massage.