A trans perspective I don ' t know you and I don ' t know him of course , but is it possible you ' ve been too supportive ? It ' s wonderful that you do support him of course , but too much support can feel like pressure at times . He may not be ready to take or even think about some of the steps that you ' re making a point of being supportive of . With regards to the sex specifically , it sure sounds like dysphoria to me , probably exacerbated by stress . Dysphoria is a funny thing and we don ' t always recognize it right away , particularly when it has to do with activities that are important to us . Also , PIV isn ' t just about the genitals it ' s also about the roles , and I can tell you that even before I developed conscious genital dysphoria I was very uncomfortable performing penetration .