What if you "succeed" in completing a TS transition,

but did it for the wrong reasons?


Yep, you get the idea!

This is one place you do NOT want to go!


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In the large majority of cases, transsexual (TS) transitions work out well over the long-term, as we've seen in the many stories documented in Lynn's Transsexual Women's Successes page.  However, in some cases a complete TS transition may totally fail to meet very unrealistic expectations, and way too late the transitioner may realize that undergoing sex reassignment surgery (SRS) was a BIG mistake. 
In Lynn's TS Informational pages, we discussed some of the social risks that face TG and TS transitioners.  In the SRS information page, we discussed some of the medical risks of the surgery itself. Here in this page, we focus on the risks involved in undergoing SRS in cases where the overall rationale for transition and/or for undergoing SRS is questionable.
Some examples of "wrong reasons" and wrong situations for undergoing SRS are (i) efforts to become a center of attention and live a "sexy life", (ii) thinking it will "automatically turn oneself into a woman" in others' eyes, (iii) deciding to become a woman on a whim (for example, in the midst of a mid-life crisis), (iv) doing it for autosexual "thrills", (v) doing it while suffering from preexisting serious mental conditions unrelated to GID (depression, bi-polar conditions,...), etc.
Regrets and adjustment difficulties seem to occur especially frequently in the cases of older intense crossdressers and sexual fetishists whose drive to transition is based primarily on male sexual feelings and habits. These individuals will gradually lose their male libidinous responses to their new female body as time passes after the removal of their testicles during SRS.  This loss of libidinous rewards, combined with accumulating practical, social and emotional difficulties in postoperative life, can lead to serious long-term adjustment difficulties for those who've "made a mistake".  (This effect is quite different from the experiencing of a heightened female libido and improvements in lovemaking capability that occur in many other postoperative TS cases).
The bottom line here is that EXTREME CAUTION is advised if you are unsure of your motives for SRS.
Examples of cases of "regrets":
Following are stories of people who have experienced regrets and have openly talked about their particular regrets. We can learn a lot from such cases, which help clarify the nature and validity of this serious warning:

Renée Richards

Dani Bunten Berry

Sandra MacDougall

Samantha Kane







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 postop 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 postop 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 postop 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 Renée. 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 Renée now acknowledges that she wishes that she had NOT undergone a sex change. 
Renée Richards
"It's not something for somebody in their 40s to do, someone who's had a life as a man, - - - If you're 18 or 20 and never had the kind of (advantages) I had, and you're oriented in that direction, sure, go ahead and make right what nature didn't. But if you're a 45-year-old man and you're an airline pilot and you have an ex-wife and three adolescent kids, you better get on Thorazine or Zoloft or Prozac or get locked up or do whatever it takes to keep you from being allowed to do something like this.''
- Renée Richards, Associated Press, February 1999.

"I wish that there could have been an alternative way, but there wasn't in 1975. If there was a drug that I could have taken that would have reduced the pressure, I would have been better off staying the way I was -- a totally intact person. I know deep down that I'm a second-class woman. I get a lot of inquiries from would-be transsexuals, but I don't want anyone to hold me out as an example to follow. Today there are better choices, including medication, for dealing with the compulsion to crossdress and the depression that comes from gender confusion. As far as being fulfilled as a woman, I'm not as fulfilled as I dreamed of being. I get a lot of letters from people who are considering having this operation...and I discourage them all."

- Renée Richards, "The Liason Legacy", Tennis Magazine, March 1999.

"She calls the 2004 decision of the International Olympic Committee, which allows transsexuals to compete, “a particularly stupid decision"" . . . "Better to be an intact man functioning with 100 percent capacity for everything than to be a transsexual woman who is an imperfect woman.”"

- Renée Richards, as quoted in "The Lady Regrets", New York Times, February 1, 2007

There may also have been even deeper issues in Renée's case, as we learn from her autobiography. Renée had been a long-term intense crossdresser, and had gone back and forth about whether to transition. In one early phase, she went on hormones. Then as self-doubts began to set in, she detransitioned off of hormones and even had her new breasts surgically removed!
Furthermore, Richards had also met with a number of young postop women in Paris, and they had all warned her against transitioning. Those girls confirmed that they themselves were happy being complete women. However, they told her that there were "others who were not so lucky". They told her about "one who was not ready, who did not have the true feminine nature" and who "after the surgery went mad".
In her book Renee says "Then I knew that this was all for my benefit", i.e., that those girls were trying to warn her against transitioning. However, she went on to do it anyways, and ended up having serious regrets.
Unfortunately, Richards now generalizes from her own sad experience and now proclaims that NO one in their 40's or older should transition. Readers should be aware that Richards is totally out of contact with the large community of successful postop women, and has no clue that many later transitioners actually do very well. It is sad to see her generalize in this sweeping way about late transitioners, and to do so in ignorance of the many successes out there.
Nevertheless, Richards' case is a good warning for some older transitioners to consider.
We can speculate further about what might have gone wrong in Renée's case, and better visualize how mistakes can be made, by reading about a more recent case of an intense crossdresser who underwent transsexual transition. Carefully consider the following essay by Dani Bunten Berry, a prominent computer game designer who underwent transsexual transition in 1992 at the age of 43:

Dani Bunten Berry

The following essay by Dani is contained in a memorial website about her career and her gender transition.  Dani was a wonderful gal who took full responsibility for her actions and didn't blame (although she questions) others for what happened to her.  Her essay contains her own honest and heartfelt words of advice to others who might be inclined to undergo SRS for the wrong reasons, as she did.
Dani was a computer scientist, and was the pioneer of multi-player computer games. She was widely known and greatly respected as a major innovator in her field. Multi-player computer games have become an underpinning for much of modern computer-collaboration technology, and thus her work has had a great impact on computing in general. For more about Dani, see the March 18, 2003 Salon.com article about Dani and her creative work.
Even though Dani's gender transition went too far in her case, she bravely made the best of it afterwards and found some degree of peace. Sadly, she died of lung cancer in 1998 at the early age of 49, and is no longer here to speak with us directly. We owe Dani a huge debt for leaving us this very candid, deeply personal essay. By being so open and honest about her difficulties after having SRS, she can speak to others and pass on her words of caution long into the future.
Dani Bunten Berry
"Special Note to Those Thinking About a Sex Change,
by Danielle Berry
[Compiled from a number of emails I sent in response to requests for input from those considering their own change.]

Don't do it! That's my advice. This is the most awful, most expensive, most painful, most disruptive thing you could ever do. Don't do it unless there is no other alternative. You may think your life is tough but unless it's a choice between suicide and a sex-change it will only get worse. And the costs keep coming. You lose control over most aspects of your life, become a second class citizen and all so you can wear women's clothes and feel cuter than you do now. Don't do it is all I've got to say.

That's advice I wish someone had given me. I had the sex change, I "pass" fine, my career is good but you can't imagine the number of times I've wished I could go back and see if there was another way. Despite following the rules and being as honest as I could with the medical folks at each stage, nobody stopped me and said "Are you honest to God absolutely sure this is the ONLY path for you?!" To the contrary, the voices were all cheerfully supportive of my decision. I was fortunate that the web didn't exist then - there are too damn many cheerleaders ready to reassure themselves of their own decision by parading their "successful" surgeries and encouraging others.

I can speak the transgender party line that I was a female trapped in a male body and I remember feeling this way since I was 4. But, it's never that easy if you look at it sincerely and without preconception. There's little question that a mid-life crisis, a divorce and a cancer scare were involved in at least the timing of my sex-change decision. To be completely honest at this point (3 yrs post-op) is not easy, however, I'm not sure I would do it again. I'm now concerned that much of what I took as a gender dysfunction might have been nothing more than a neurotic sexual obsession. I was a cross-dresser for all of my sexual life and had always fantasized going fem as an ultimate turn-on. Ironically, when I began hormone treatment my libido went away. However, I mistook that relief from sexual obsession for validation of my gender change. Then in the final bit of irony, after surgery my new genitals were non-orgasmic (like 80% of my TG sisters).

So, needless to say, my life as a woman is not an ultimate turn-on. And what did it all cost? Over $30,000 and the loss of most of my relationships to family and friends. And the costs don't end. Every relationship I make now and in the future has to come to terms with the sex-change. And I'm not the only one who suffers. I hate the impact this will have on my kids and their future.

Anyway, I'm making it sound awful and it's not. There are some perks but the important things like being comfortable with myself and having a true love in my life don't seem like they were contingent on the change. Being my "real self" could have included having a penis and including more femininity in whatever forms made sense. I didn't know that until too late and now I have to make the best of the life I've stumbled into. I just wish I would have tried more options before I jumped off the precipice. I miss my easy access to my kids (unlike many TS's I didn't completely lose access to them though), I miss my family and old friends (I know they "shouldn't" have abandoned me but lots of folks aren't as open minded as they "should" be ... I still miss them) and finally, I hate the disconnect with my past (there's just no way to integrate the two unrelated lives). There's any number of ways to express your gender and sexuality and the only one I tried was the big one. I'll never know if I could have found a compromise that might have worked a lot better than the "one size fits all" sex-change. Please, check it out yourself before you do likewise."

- Danielle Berry -
What we learn from Dani's candid essay is that both she and her counselors ignored, or were unaware of, key warning flags. She lost her (male) libido when she began taking estrogen, without any heightening of any female libidinous feelings. This was a predictor that she might possibly become inorgasmic postop. Her comments that CD's/TG's transition "so you can wear women's clothes and feel cuter than you do now" and that "I was a cross-dresser for all of my sexual life and had always fantasized going fem as an ultimate turn-on" reveal that her motive for transition was a male CD sexual turn-on. Her loss of orgasmic capability postop proved to be an especially cruel outcome of her search for an "ultimate turnon".
Dani was left with all the usual difficulties of gender transition, but gained none of the profound benefits felt by many postop women. This is an all-too-common result among the recent spate of late-onset transitions. Dani's guess that 80% of CD's/TG's end up inorgasmic IF they undergo SRS may be about right - whereas the reverse is likely true of those who are intensely TS (follow-ups indicate that a majority of early-transitioning TS's are orgasmic postop).
Dani would threfore have been much better advised by her counselors to undergo FFS to correct her very masculine facial structure and then quietly undertake a TG social transition. She could have taken hormones, undergone electrolysis, changed her social gender and name and ID's, and lived as a woman - but NOT had sex reassignment surgery. She would undoubtedly been far happier, and as a prettier woman would have encountered a better social reaction to her gender transition. She could have also continued to enjoy her male autosexual transvestic practices. Tragically, this option wasn't visualized and presented to her in 1992.

Sandra MacDougall

The stories of Renee and Dani are not isolated instances. There have been many TS transition failures in recent years. Ever-increasing numbers of late-transitioning intense CD's and self-proclaimed "autogynephiles" are getting letters of consent from careless counselors and then unwisely undergo SRS, without being fully prepared to live as women and without having clear notions of the other options available to them.
For example, see the 4/28/02 Scotsman.com news story about Sandra (Ian) MacDougall (49), entitled the "Torment of sex change soldier trapped in a woman’s body" (more)
Sandra (Ian) MacDougall

"The former member of the Scots Guards says she has suffered verbal and physical abuse since her sex swap operation almost four years ago, and wishes it could be reversed.

But MacDougall now finds herself trapped in a woman’s body after she consulted doctors and was told the operation could never be reversed.

MacDougall, who has not had a relationship since going under the knife and expects to be celibate for the rest of her life, has now decided to make the best of her hard-won gender. She said: "Since I had the operation my life has been made a misery by people taunting me whenever I go out."


From the context of the article, it seems clear that Sandra is an intense CD (she has "more than 80 dresses, bags of makeup, and a whole cupboard full of shoes"). It is also clear that she (i) wasn't prepared or emotionally ready for social transition, (ii) had no idea how people were going to react to her afterwards given her lack of preparedness, and (iii) apparently somehow thought that undergoing SRS was going to magically do what she herself had not yet done by other means  - i.e., change her social persona and apparent social gender to female.
As a result, her life has been totally miserable ever since undergoing SRS. She doesn't pass and everyone in her community makes fun of her. She never has, and never again will have, sex. She desperately wishes she "could go back", but there's no way to reverse the surgery.
Sandra's best option at this point might be to de-transition socially and hormonally (return to the male role and go back on testosterone), but she doesn't seem to be aware of that option either. Total transition failures of this type should serve as extreme warning signals to intensely fetishistic crossdressers (and to those who self-identify as "autogynephiles", i.e., as sexual paraphilics, according to their therapists) who are considering undergoing SRS.

Samantha Kane

Then we have those who "change sex" on a whim and have the financial means to do so, then afterwards have regrets and sue everyone in sight who "did this to them" - while not taking any responsibility whatsoever for their own actions.

For example, consider the case of "Samantha Kane", and then think about the damage that this impulsive person has done to himself and about the harm he is now doing to trans women everywhere by his irresponsible actions - both in transitioning and then in lashing out as those who tried to help him in the first place.


(Sam Hashimi => Samantha Kane => Charles Kane)

"Sam, as he was"


"Samantha, as he erm was?"

"Charles, as he is today!!!"


"Samantha Kane was, by anyone's standards, a hugely successful woman. She ran her own interior design company; was independent, modern and extraordinarily beautiful. She had a top of-the-range Mercedes, homes in West London and Spain and accounts at Knightsbridge's most exclusive boutiques. Her name made her sound like a character in Dynasty - and her feline looks would certainly have qualified her to be one.

She rubbed shoulders with the likes of the Crown Prince of Dubai, ran with the international set in Monte Carlo and Cannes and shared her bed with a number of fabulously wealthy men.

But something inside Samantha hated being a woman. She found the conversation superficial and the sex second rate. She loathed shopping, disliked gossip and fretted over the endless maintenance of her face and figure. In short, Samantha Kane desperately missed being one of the boys. 

For Samantha used to be Sam, a millionaire with a property empire and a husband with two children. As Iraqi-born Sam Hashimi, he brokered million-dollar deals for Middle Eastern businessmen and flared briefly in newspapers when he launched an unsuccessful takeover bid for Sheffield United FC.

Following the first Gulf War, Sam's business empire collapsed and his marriage ended. At 37, seemingly out of the blue, he decided to become a woman.

He had a sex change operation in December 1997 and spent close to £60,000 on surgery - including £10,000 on genital surgery and £3,000 on breast implants. 

Within four years of the operation, Sam realised 'he'd' made a dreadful mistake and has begun the painful process of having more surgery to return to being a man again!.

He was in the headlines again, claiming his sex change was 'an act against nature'. He has reported his doctor, consultant psychiatrist Russell Reid ... to the General Medical Council alleging he had a `cavalier attitude' in recommending him for the gender realignment surgery.

He registered officially as Charles a month ago, wanting to put as much distance as he could between Sam and Samantha.

He cuts a poignant figure of a man. Charles is dressed in a pin-stripe suit and pink tie - an amalgam of man and woman. His hands are soft with clean, shaped nails. He walks and sits in the manner of a woman, but uses the men's lavatories. 

He has no facial growth and little male muscle. He says it took four years of hormone treatment and surgery to feminise his body completely. It will take as much time again to return it to manhood. But Charles will never be as Sam was. His genitals will be re-constructed by plastic surgery. His body will never naturally produce testosterone and he will never again grow a beard. 

Charles cannot give a convincing reason for becoming a woman. He says he was suffering from a nervous breakdown when gender change was recommended and that he should have been referred for counselling not surgery.

'I was a traditional male. I was strong and tough in business and the provider for my family. My wife Trudi had never worked a day of her life. I shouldered the complete financial responsibility for her and the children,' he says.

'She'd think nothing of going shopping and spending a few thousand pounds on a dress. I always used to wonder what it would be like to be a woman, to have none of the responsibility I had, to have doors opened for me and have all the privileges a woman seems to have.' Until his breakdown, he was thoroughly heterosexual; a conventional, grey-suited businessman with short dark hair and a moustache.

Born in Baghdad to middle-class parents, he moved to England at 17 where he secured an HND in engineering and married Trudi, a former beauty queen, at 23. He built a property empire, negotiated deals for wealthy Arabs and ran a club in Mayfair. At one time, he says, he had £2 million in the bank.

'I was like any other man,' he says. 'I worked hard and did pretty much what I liked. I enjoyed spending time with men talking about football, the stock market and, of course, girls. I think my sex drive was above average. I had one or two affairs during my marriage..."


BBC1, Tuesday 19th October 2004 1035pm

After the failure of his business and departure of his wife and children, Sam Hashimi took the drastic decision to undergo surgery to become a woman.

It was only later that the ex-millionaire realised he had made a terrible mistake. As he prepares for the final stage of a sex-change reversal, Hashimi wonders if he will be accepted as a fully fledged male.

Documentaries about people undergoing sex-reassignment are extremely common these days. But this one is quite extraordinary. It follows Samantha, a wealthy 44 year old property developer who was born a man (and as Sam was married for ten years and had two children), but who seven years ago had a sex-change operation.

Now - and here's the twist - Samantha wants to become Charles and is on the brink of having another sex-change operation to turn her back into a male again. "I was robbed of my manhood for so many years" explains Sam/Samantha/Charles, ignoring the fact that it was his/her decision to undergo surgery.

While Charles waits for the final bit of reconstructive surgery, we see him getting into an hysterical state about an expensive yacht he's buying (and which he hopes may help him find a girlfriend). In a way it's yet another example of how he rushes into things without thinking about the consequences.

It's obvious that he's a complex person who's extremely confused about what he wants, but you'll still sit open-mouthed that anyone can make radical life-changing decisions like this on a whim.




For more information on this case, see:




For a more extensive discussion about cases of "regrets", and also about groups of religious zealots and anti-gay ideologues who sometimes prey on these cases - smothering them with attention to get them to suddenly de-transition and then sue everyone in sight - see Christine Beatty's page entitled Transsexualism, Regrets and "Reparative Therapy":



See also Joanne Herman's article "Transsexual Regret", The Advocate, March 13, 2007:





It is clear that you must be very, very honest with yourself about "why" you need to transition, and whether a TS transition (including SRS) will meet your inner hopes, aspirations and expectations over the long term. No one else can know your inner feelings of "why you need to do this", and no one else can predict how competent you might be at doing this. It is VERY important to be brutally realistic with yourself about your motives, capabilities and expectations before committing to a complete transsexual transition. So do be careful and think long and hard about the above warnings.
Listen to your heart and to your body, and don't let perceived social pressures force you into something you'll regret. If you really enjoy your male sexuality preop (especially male "mounting, thrusting and penetrating" urges), then you are unlikely to develop and enjoy a female sexuality after a TS transition. Instead you may simply regret losing your male sexuality, and that will be such a turn-off that you may become sexually "cold". If you think this is a possibility, you should seriously consider TG social transition without undergoing SRS.

Furthermore, those at risk for very difficult social transitions should realize that SRS will not in and of itself somehow miraculously "make them a woman in other people's eyes".  After all, the only people who see your genitalia are those whom you are intimate with (and your physicians, etc.) and thus SRS by itself will not affect the general reactions of those around you.  In cases where serious difficulties are expected in social transition, it might be wise to give FFS priority over SRS, because FFS has a much more profound effect on the reactions of others to one's transition.

Suddenly transitioning and then undergoing SRS on a whim is an especially bad idea, no matter how much money, influence, or power one has with which to make it happen. Seek counseling instead.  Learn about the alternatives.  Slow it down.  Listen to the advice of  Dani Berry and reflect on the case of Samantha Kane above.

However, if you feel a very deep need to be a female in body-sex as well as in social-gender, and especially if you feel a deep need to fully express your female sensuality in intimacy and lovemaking, then transsexual transition and SRS may be right for you.


Lynn Conway


["SRS Warning" Version of 4-09-05; update of 3-16-07]

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