I recently found this interesting piece of information from the Internet about four transsexuals that regretted having changed their sex.
Renée Richards
First consider the case of Renée Richards, who transitioned and had SRS in 1975 at age 40, and who was widely outed the next year as the "transsexual tennis player". Renee's story was widely reported in the media, and her story initially did a lot of good by announcing to a new generation of young TS girls that "sex change was possible", just as Christine Jorgensen's case had done in the mid-1950's. In 1983, she went on to write an autobiography about her transition entitled "Second Serve", which stimulated further notoriety about her situation and about transsexualism in general, especially regarding whether post-op women should be allowed to participate as women in competitive sports.
Unfortunately, the extensive publicity about Renée's "sex change", publicity which she largely brought on herself, generated a widespread public image of her as a "transsexual" rather than a woman. The mystique surrounding her case widely propagated the image that post-op women are not women after all, but are instead whatever "Renée Richards" is.
Part of Renée's problem with public acceptance, and possibly (though unconsciously) with her own inner self-acceptance, was undoubtedly her unusual facial structure. She had a very feminine, well-toned and attractive body, and must have thought of herself as being very beautiful. She sought media attention at every turn, and her photos were widely disseminated. Unfortunately, she never seemed to realize that she had a very prominent male brow-bulge and large male jaw and chin. Back in the 1970's and 80's, few transsexual women were aware that such features gave off powerful male gender cues, causing unease in other people without those people quite knowing why they felt this reaction (this awareness developed much later, in the 1990's, as people saw the dramatic before/after results of Douglas Ousterhout's pioneering facial feminization;surgeries).
For whatever reasons, including the sports-based notoriety surrounding her name - combined with the wide dissemination of her photographs - people always seemed to think of Renée as a "transsexual" rather than as a woman. This was unlike the situations that had faced other widely known post-op women such as Christine Jorgensen and April Ashley, who although facing problems of discrimination were nevertheless quite generally thought of and reacted to as women by most folks, even in those early days.
In the end this may have become a major problem for Renee. Or perhaps as the media attention faded and as social, relational, emotional and physical realities set in, her hopes for an unendingly sexy, exciting life as a center of attention faded too. Whatever the reason, her transition failed to meet even her own expectations, and Renee now acknowledges that she wishes that she had NOT undergone a sex change.