How do I anally fist myself? Q. I'm an 18 year old boy, and have no girlfriend. I want to anally fist myself. I know that some people (male and female) are able to accommodate a hand in their anus; that's my target. Now I can just get three fingers inside my anus. But how and when can I get a hand in my anus? A. Well, with three fingers in, you are already halfway there! The basic idea behind being able to accommodate your whole fist in your anus (or a vagina) is to be well lubricated and to work your way up to it slowly, finger by finger. The last thing you want to do is rush the journey and damage the sensitive tissues of the rectum (or vagina). From three fingers, carefully add a fourth and finally your thumb. From here you face the trickiest part, which is getting your knuckles through the anal opening. With all five fingers inside, your hand will naturally take the form of a duck's beak, drawing your knuckles together. Males generally have a larger knuckle breadth than women, but if your hands are not overly large, easy-does-it should still pay off! Once your knuckles pass through, draw your hand into a fist, and success! Remember to use plenty of lubricant. Neither the anus nor the rectum produce their own lubricant naturally, so an abundance of good quality lube is essential in order to facilitate any kind of pleasurable penetration, especially a whole fist. Lubricants of various bases are available discretely via our website. You will find Lubricants specifically formulated for anal sex are usually water-based or silicone, boasting qualities such as longevity and non-sticky/greasy consistency. If you find that even with plenty of lubricant you are having trouble moving past the three-finger phase, there are a couple of things you can try. Sex toys are one great way to enjoy anal stimulation without the anatomical awkwardness of trying to insert your own fist. Toys can also be a great way to warm up to anal fisting, getting you relaxed and turned on prior to the main event! Since females tend to have smaller hands than males, you may find that a future female partner may be just what the doctor ordered in terms of getting you to your end goal with ‘a little help from a friend’! For more information check out our comprehensive and informative article on Fisting, and be sure to have a look through our Anal Sex Toys and Lubricantsarticles.