The first challenge for a crossdresser in their first anal experience could be acceptance. Accepting that they are about to engage in such an experience can be tough due to society's taboos around it. Then, there is the matter of safety. They need to ensure that they are using safe products and techniques. For example, not using sharp or inappropriate objects. Also, they may struggle with body confidence during this new and perhaps intimidating experience. If they are not confident in their body, it can add more stress to the whole situation.
Well, one possible challenge could be psychological discomfort. The crossdresser might feel self - conscious or have internalized stigmas. Another is physical pain. Without proper preparation like using enough lubricant, it can be really painful. Also, there could be a lack of knowledge about proper hygiene which is crucial in this situation.
A crossdresser may face challenges during their first anal experience. Firstly, they may be worried about how it will affect their self - image, especially if they are still exploring their identity. Secondly, physically, if they are not relaxed enough, it can be difficult and even cause minor injuries. And lastly, they might be unsure about how to communicate their feelings and experiences to their partner if they have one.