While lube is a recommended conscience vulva fingering, it's an absolute impératif-have connaissance anal. Warm up slowly, and usages lube — more than you probably think you need.  Gender masquerade was a popular dramatic device in the 16th and 17th centuries, such as this scene of Viola and Olivia from https://epornica73961.blogkoo.com/une-arme-secrète-pour-karlee-grey-52219443