Triumph of the Female Pervert

Lou Sullivan was a woman who wanted to have sex with gay men

“I far from hate myself, sometimes I fear it’s too much the opposite.”

Sheila Jean (Lou) Sullivan, early 1970s

When Lou Sullivan started seeking hormones and surgery in mid-1970s California, gender doctors didn’t know what to do with her. They were used to treating women who wanted to marry women, but Sullivan told them she wanted to have sex with gay men.

Sullivan is a sacred character in trans lore. Writers talk about her like a kid sister; the photos they choose show a goofy person less threatening than the average mathlete. They play up her geeky pastimes and euphemize her sex life.

New York Times in 2023:

“While Sullivan was many things — a secretary, typesetter, educator, activist, historian, community organizer and pleasure seeker — he is best remembered as a writer and activist.”

MTF historian Susan Stryker (emphasis added):

“Lou did not live up to the promiscuous stereotype of a gay man in San Francisco in the 1980s … Sullivan could count his long-term sex partners on one hand.”

In fact Sullivan was a gleeful slut who centered her life around sex. After her 1986 genitoplasty she wrote to sexologists, beseeching them to “document” her case. They grilled her about her erotic life. She appreciated the attention.

In this post I’m going to write a bio for Sullivan that draws mostly from her own words found in correspondence, diaries, and interviews. She kept meticulous records of her life so that future generations could understand “a phenomenon such as myself.”

In some quotations I’ve cleaned up typos, abbreviations, and spelling errors.

The Sex Begins

In 1951 Sheila Jean Sullivan was born into a big Irish-Catholic family in Milwaukee, Wisconsin, the third of six siblings. Her father owned a hauling and moving company. As an adult she described her parents’ sex life:

“A major topic of my parents’ arguments. My father would complain that he’s not getting any action, that my mother doesn’t put out, but that he’s too good a man to seek it elsewhere. My mother disdains any pleasure in sex, always spoke of it as ‘laying back and letting dad “have his fun”’ so she could have her children. I doubt she has any sexual desires at all. … I’m sure they’re both sexual basket cases.”

Sullivan started picturing herself as a man from the time of her first sexual fantasies. She told a friend that when she was “15 I stuffed a rag into my underwear for my penis and walked around like that all day, dreading exposure.” She’d later tell gender doctors that cross-dressing “was a sexual turn-on” when she first started doing it, but the thrill dissipated by her mid-20s.

She wrote in her diary as a teen:

“I masturbated bout 5 times at work, drew dirty pictures, wrote dirty stuff”

According to the New York Times in 2023:

“[Sullivan] understood the value of political activism early on, and participated in civil rights and antiwar protests as a teenager. In 1973 he joined Milwaukee’s Gay People’s Union, a rights organization, serving as secretary.” 

This was after she wrote in her diary:

“A long time ago I saw the Gay Liberation Front recommend the reading of several books on homosexuality, which you know I have always been strangely attracted to. … I got [City of Night by John Rechy] immediately. Story of a male-hustler, a male prostitute for homosexuals. The whole story was so sad and lonesome … my heart and soul is with the ‘drag queen.’

“And how can I help. The last week or so I’ve wanted to go and leave everything and join that world. But where do I fit in. I felt so deprived and sad and lost. Last Monday I came home on the bus alone [without my boyfriend]  … and I was so close to ‘cruising’ Brady Street and trying to get picked up. So damn close.”

Note the pity and horniness lying side by side. “And how can I help” –  you'd expect to see a question mark at the end of that sentence if she were interested in a gay man’s answer.

Sullivan defended Rechy’s degenerate gay characters to a friend:

“Where do you mold a life for yourself when all you do is battle oppressions day in and day out? … Rechy’s world is as valid and fresh a life as a black shouting out his SOUL or a wife splitting from her hubbie and kids and shouting her liberation.”

Should’ve tried genitoplasty, Grace.

Sullivan moved in with her first serious boyfriend, Jim, around age 18. He was down to experiment with men, butt stuff, and gay identity. She wrote in her diary about an encounter with teen boys:

“One of them, seeing J run across the street in all his beauty remarked to the other ‘Look at that fag.’ I was instantly turned on, ran after him + threw my arms around him. . . . he’ll never know why.”

The TERF Friend

Sullivan is hailed for writing an essay that told off “transphobic” feminists. “A Transvestite Answers a Feminist” was published in a Milwaukee gay newsletter in the early 1970s. At the time, Sullivan was in her early 20s and recently split from Jim. Her friends knew her as a woman named Sheila who wore pants.

The celebrated essay is actually an annotated series of letters between Sullivan and her coworker-friend, Dorothy, sparked by an argument about cross-dressing. They worked together as secretaries at the local university. It appears Sullivan published the correspondence without Dorothy’s permission.

Sullivan maligns her older sister for her conventionally feminine appearance; Dorothy points out the hypocrisy of lauding the same frippery in campy men. Sullivan:

“My older sister is inferior to a transvestite becuz she can’t relax, she’s trying so hard to deny her inner humanity and free-ness, to bottle up any susceptibility to feelings – while a transvestite at the very least, admits to himself his inner life and feelings, and, at the most, if he comes out, he’s left wide open for rejection by family and friends, physical harm, denial of use of public and private facilities, easy prey …”

Dorothy challenges Sullivan’s fixation on male and female roles:

“[S]ee if you can come up with any sort of ‘image’ of a HUMAN – i.e., what makes a person, rather than what is a man or a woman. What happens when you discover that a man is tender, a woman aggressive; a man is spiritual, a woman is intellectual?”

Dorothy also accuses Sullivan of passivity:

“[Y]ou sit here in your ‘masculine’ clothing (pants, masculine? nowadays?) typing and liking it. No wonder you are falling for this clothes makes the man bit.”

In a later letter, Dorothy shows her feminine side:

“I really feel awful about the last couple days. You were my feminist friend … I’m a wide-eyed dreamer, a utopian thru and thru. And that is why I am being such a bitch towards you right now.”

Sullivan’s response:

“I’ve always thought of myself as a male homosexual (try and figure that one out – I can’t). I think the reason I think that stems from my hate for the female scene.”

According to Sullivan, Dorothy was cold to her from then on. 

In 1987 Sullivan wrote to a friend:

“I believe gay women are becoming more accepting and liberal in their attitude toward F-M transvestites/transsexuals. In years past I received such flak for being a traitor to Womanhood and ‘going to the other side,’ but those sentiments are no longer in the air.”

Transition

Sullivan moved to San Francisco in 1975, in her mid-20s. By then she was dressing almost exclusively in male clothing (pants, masculine? nowadays?). She and Jim were back together and role-playing as a same-sex couple in the bedroom and in public, including at gay bars. But Jim didn’t want Sullivan to medicalize. She began the process after he left her for another woman.

She imagined that after the transition, “I will have to bear the discrimination/prejudices, etc., that effeminate gay men do every day.”

Twice in the late 1970s, Sullivan applied to Stanford’s gender clinic and was rejected. She named herself Lou after Lou Reed and went about transitioning piecemeal. FTM “peer counselor” Steve Dain advised her to go for it (“he couldn’t believe how much I’d been through these past six years of dressing/passing”). She scored testosterone with the help of sexologist Wardell Pomeroy in 1979. 

The next year Sullivan underwent mastectomy, which left her swollen for at least four months. “What a thrill – I feel so sensual I’m making myself crazy.” It cost her $4,300 (about $17,000 in 2024). She was still working in secretarial roles.

She hesitated to take the next step:

“I’m not so hot on a hysterectomy. Part of the female orgasm is the contracting of the uterus and I don’t like the possibility of jeopardizing having the great orgasms I’ve been having lately.”

Since the surgery she’d had “two separate rendezvous with gay men who never asked me a single question … we had wonderful sex and they never treated me as anything other than another gay man.”

Sullivan considered her genital options:

“As for a cock. Sure. But fat chance. I know of nothing that works. [Dain] had what he calls ‘freeing the clitoris’ … then had testicle implants and the labia sutured together. He is beautifully passable, though small and of course unable to function for urination or intercourse.”

Ultimately in 1986 Sullivan chose “genitoplasty.” The surgeon sliced into the sensitive flesh around her clitoris (enlarged by testosterone) to make it stick out. She picked this over phalloplasty because she’d been “terrified” that the latter would interfere with her ability to orgasm. She told a gender doctor that she was able to afford the surgery thanks to a recent inheritance.

About Those Stanford Rejections …

When Sullivan applied to be a patient at Stanford University’s gender clinic in the 1970s, she disclosed she planned to “be a gay male having sex with another gay male.”

She mentioned on her first application:

“I feel a homosexual attachment is more honorable, solid and natural than a heterosexual attachment.”

Stanford rejected her both times she applied. Its surgeon, Donald Laub, would write a mea culpa in 2019:

“Another requirement that was dropped, one that seems painfully antiquated now, was that the patients were only accepted into the Gender Dysphoria Program if they intended to be heterosexual after the surgery. The outrage of the transgender community helped enlighten us on that issue.”

Trans activists spin that requirement as homophobic, but in fact gender doctors were discriminating against heterosexuals. Nor did they necessarily oppose “same-gender” couples. 

In 1985 Sullivan sought Laub’s services yet again, for genital surgery. This time he was in private practice (like most other university gender clinics, Stanford’s shut down by 1979). She wrote to a friend in 1985:

“[Laub’s office] rejected me from consideration for the surgery over the phone without ever having seen or talked to me because I have sex with men. They said they’ve determined that an F-M can’t make it in the gay men’s world because all gay men care about are 10-inch dicks… well they didn’t put it that way, but they said they showed pictures of the cock operation to gay men and it didn’t turn them on so now they know an F-M can’t be a gay man.”

Many gender doctors of that era worried about how patients would fare post-surgery. This led them to reject candidates who couldn’t possibly pass, for example. Trans activists today frame that “gatekeeping” as vicious discrimination. But it was really, at worst, paternalistic.

Best Little Boy

Sullivan threw herself at San Francisco’s gay male community, volunteering for gay civic organizations by day and having anonymous sex at night. 

Sullivan during a 1988 interview with Ira Pauly

In 1988 Sullivan sat for a videotaped interview with Ira Pauly, the psychiatrist who transed a 14-year old lesbian. Sullivan talked about her sex life as a gay man. It included giving anonymous blowjobs at San Francisco gay bars like “Glory Hole” – anonymous so her partners wouldn’t realize she was female. (Elsewhere she mentioned engaging in anonymous “tenderness” in dark porn theaters.) She also had vaginal and anal sex with bisexual boyfriends who knew her deal.

Sullivan said she didn’t care about seeming masculine. Pauly seemed taken aback. 

Sullivan: I don’t think I’ve ever bought into the male role … I never thought, well I should do this because it’s a male thing. I’ve never done that.

Pauly: What you mean is you’ve never bought into the macho role, but you’ve obviously bought into the male role.

Sullivan (laughing): Oh yeah, yeah I suppose in a general way, yeah.

Why should Sullivan try to seem masculine? She didn’t want to be a generic man. She wanted everyone to think she was a gay man.

In 1989 Sullivan responded to a query about her sex life from the Toronto gender psychologist Ray Blanchard:

“Have I so far just watched at the ‘jack off club’? No, I have masturbated there while watching others ‘jack off.’ In the name of ‘safe sex,’ that’s all one is allowed to do there.”

“I would very much like to be documented”

Sullivan welcomed these questions. She loved talking to gender doctors. From the late 1970s through 1985 she encountered leading lights of the profession as she quested after treatment. This is how she met Pomeroy and befriended Paul Walker, a gay psychologist who co-founded WPATH’s predecessor, HBIGDA. 

After Sullivan’s genitoplasty, she contacted gender doctors like Pauly, Blanchard, Eli Coleman and Walter Bockting (both psychologists at the University of Minnesota). The reason, as she told Pauly in 1987:

“I would very much like to be documented, so that in the future others like myself will not search the transsexual literature for a mention of someone like themselves in vain (as I did).”

The gender shrinks were psyched to meet this specimen.

Blanchard let Coleman know that he planned to write about Sullivan in his manuscript on “non-homosexual” transsexuals, but would credit Coleman as having gotten there first. Pauly conducted hours of interviews with her, introduced her to his medical students, and moderated a Q&A with her at a 1990 convention of psychiatrists. He estimated that over a hundred attended. 

Decline

Sullivan found out on New Year’s Eve, 1986, that she’d contracted HIV and had full-blown AIDS. It came as a surprise because “I figured I was pretty much invulnerable by virtue of being a biological female. The joke was on me!”

Sullivan’s plucky reaction is widely quoted:

“They told me at the gender clinic that I could not live as a gay man, but it looks like I will die as one.”

Her recent genitoplasty had included testicle implants. One of them didn’t stick. Sullivan described to Pauly what it was like to learn her AIDS diagnosis: 

“My first thought was oh great, now I’m going to die, I’ve got one ball and there’s no way this surgeon is going to operate on me again, having AIDS, and reinsert this implant, and I’m going to die with this surgery never even done. And that was I think the worst part of finding out I had AIDS.”

The surgeon did agree to go through with the job. Pauly: “So you feel complete now?” Sullivan said yes, but unfortunately now she felt like “a walking germ” because of AIDS. “So I still can’t feel comfortable with my body.” But she assured the audience that she was maintaining an active sex life that kept all participants safe.

Sullivan provided another set of details about the surgery to a friend:

“Since I have the testicular implants in each side of the labia majora, I want [the surgeon] to sew my two ball sacs together, so I have one scrotum like a regular guy. Plus, there are two bands of skin holding my dick down on the underside, and I want him to cut those.”

She knew AIDS would kill her within a few years. She was planning to spend her final months undergoing and recovering from cosmetic genital surgery. 

In 1990 Pauly interviewed Sullivan again. She was visibly sick now and detailed her struggle with “itchy” anal herpes.

Lou Sullivan died in 1991 at age 39.

Who Was Lou Sullivan?

If you think of Sullivan as an oppressed gay trans man, then her determination to put her fetishes into the historical record is noble. If you think of her as a fetishist, then her determination to put her oppression into the historical record is narcissistic.

Reading and listening to Sullivan’s words, I can’t help thinking of fetishistic MTFs.

(For gender newbies: US gender doctors have observed since at least the 1960s that many men seeking their services are motivated by a fetish. Through the 80s they were called transvestites. Blanchard tweaked the concept and renamed it autogynephilia, or AGP, around 1990. The DSM now calls it “transvestic disorder.” I tend to avoid these clinical terms because I suspect there’s more to the condition than gender doctors have set out. Here’s more from Malcolm Clark. Some argue that a female equivalent exists called autoandrophilia.)

Sullivan wasn’t just turned on being a man, but by being a gay man. The idea of being oppressed titillated her. It’s like men watching sissy porn. Those guys are known for adopting vulnerable female identities in their fantasies, like young girls and submissive ultra-femmes.

From adolescence Sullivan entered gay spaces, taking leadership roles in their civic groups first in Milwaukee and then in San Francisco. She cast herself as a gay man par excellence. This sounds like MTFs who take over endometriosis charities and Democratic women’s groups.

That Sullivan’s incursions were so geeky and cringe only deepens the parallel with fetishist MTFs. The ones I’ve seen on dating apps posing as “lesbians” include a guy wrapped in a blanket holding a stuffed animal; a guy wearing a covid mask with the caption, “my school pictures are today!!!”; and scowling galoots in cheap wigs who seem not to be trying. 

Finally, the sordid tone of Sullivan's story reminds me of so many Reduxx articles. The worst thing about receiving her death sentence was the fear it would derail her fake-testicle plans? This is hell.

The cross-dressing male fetishist has been running wild for a hundred years. How come his sister didn't emerge until the 1970s? Lou Sullivan belonged to the first generation of girls exposed to gay male culture from the time of their earliest sexual development. Before then, girls inclined to fetishize vulnerability had little inspiration to view men as prey. 

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This post was lightly edited on Sept. 29, 2024.