I am not a tax specialist and my dilator was purchased in an adult book store so I didn't claim it but if you are worried about it, a quick note from Dr Mcginn would cover your bases. When I transitioned, everything I paid out of pocket was deductible and because they didn't have the minimal limit on medical expenses My taxes looked a good deal different than they do today. Electro and therapy session were a major part of my deductions but I had hormones and some of the surgical costs mixed in.
In any case, I think this applies.
Medical expenses are the costs of diagnosis, cure, mitigation, treatment, or prevention of disease, and the costs for treatments affecting any part or function of the body. These expenses include payments for legal medical services rendered by physicians, surgeons, dentists, and other medical practitioners. They include the costs of equipment, supplies, and diagnostic devices needed for these purposes.
