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Best Beginner Dildos for Pegging and Strap-ons Please note that this beginner’s guide is specifically about choosing a strap-on dildo for the purposes of pegging and anal penetration. Not every dildo that’s available on the market is suitable for a strap-on or anal penetration, so you need to learn what features to look for before purchasing a dildo for this purpose. You don’t want to end up with a hurt bottom or with a dildo that you can’t equip! How to Choose a Beginner Dildo for Pegging and Strap-ons There are several factors that you need to consider while choosing a beginner strap-on dildo. Let’s discuss them one-by-one: Length : For anal penetration, a strap-on dildo needs to be at least 5.5 inches in length. Remember that the strap-on harness will be covering up part of the dildo. You need sufficient length to go through the harness and past the buttcheeks while still providing a pleasurable amount of penetration. In my experience, 5.5 – 6 inches is the perfect start...