Male sex work diaries: archival discoveries from the journal entries of Thomas Painter and Sam Steward

Yuriy Zikratyy

The emergence and consolidation of gay male communities that took place in the modernized West roughly in the period of one century, between the 1870s and the 1960s, revealed the close connection between the worlds of homosexuality and prostitution. In large urban centers from San Francisco to Berlin, queer and nonbinary men shared spaces with female sex workers, emulating their styles and adopting their argot and survival strategies in the streets (Chauncey, 1994; Healey, 2001; Houlbrook, 2005; Peniston, 2004). Female prostitutes and other “tough girls”provided a cultural script for the queer underground subculture to develop. The scientific and popular discourses that reported on the two phenomena saw them as essentially the same: a symptom of society’s moral degeneration, a metaphor of urban chaos brought about by immigration and industrialization, or a physical embodiment of the new sexological concept ot perversion (Ben, 2018).

The connection of sex and money was also conspicuous within the queer community itself. A gender-based model of same-sex desire, in which one male partner in a couple is heterosexual and masculine (“normal”) while the other is effeminate and queer, was by no means the only model ot homosexuality at the time, but it was influential and helped shape the sexual lives ot many. It inevitably positioned “normal” men as the only possible objects ot queer desire, but they were at the same time inherently unavailable, as, according to this logic, they would always prefer a “real” woman to its male imitation. These normal men had to be purchased. In the words of French writer Marcel Proust, queer men (he called them “inverts”) were

lovers to whom the possibility ot that love ... is all but closed, simply because they are much taken with a man having nothing ot the woman about him, with a man who is not invert and cannot, in consequence, love them; so that their desire would be forever unsatis- fiable were money not to deliver up real men to them, and imagination not finally to lead them to mistake the inverts to whom they prostituted themselves for real men.

(2004, p. 17)

The quick and anonymous nature of commercial sex also befitted many queer men who were closeted or led risky double lives. In pre-1970s gay archives, both public and private, the theme of buying and selling sex is often present, and the whole cultural image of a male hustler emerges. He is longed tor and at the same time pitied as a figure of fragile white masculinity. He is also idolized (and racialized) as a sex instructor of sorts, a guide into an exotic, more sexually open culture (Friedman, 2003; Kaye, 2004). The realities ot male-to-male commercial sex and its representations in personal testimonies and subcultural press contributed to modern gay identity.

As the practice of recording one’s sexual experiences in the form of diaries, memoirs, and private correspondence grew in popularity by the turn of the twentieth century, it became an important means of self-expression tor sexual minorities, from unusually adventurous heterosexuals (My Secret Life, 1888) to nonbinary “third sexers” (Autobiography of an Androgyne, 1918). Sex workers rarely wrote these works, but they were their frequent subjects. In fact, numerous sexual records examined by historians as narratives ot queer sexuality can be equally seen as the testimonies of sex workers’ clients. In them, we see that hustlers often held some power over their clients, defining the terms and conditions of sexual exchange. These written records otter a rare insider’s view into the world ot male sex work. In this chapter, I examine the diaries of two singular men who hired male prostitutes. I focus mostly on Thomas N. Painter, but I also provide quotations from Samuel M. Steward, who published his work under the pseudonym Phil Andros.

Diaries from the twentieth century

Thomas N. Painter (1905—1978) and Samuel M. Steward (1909—1993) produced remarkable testimonies of their renegade sex lives, which consisted of numerous money-based relations with hustlers and other working-class men. They not only described their own sexual encounters with sex workers (hundreds ot men in both cases) but also tried to analyze and interpret them for themselves and for the reader. They kept diaries, took photographs, and even wrote books about the world of paid sex—Painter’s Male Homosexuals and Their Prostitutes (1942, unpublished) and Steward’s Understanding Male Hustler (1991). Their shared point was that sex with hustlers, however dangerous, expensive, or unsatisfactory, was an indispensable part of a certain segment ot queer life and possessed its own social, emotional, intellectual, and of course purely physical pleasures. At the same time, however, it must be observed that for both men, their sexual obsessiveness, which structured nearly every aspect ot their lives, was hardly typical of most homosexuals ot their time. Moreover, their fetishization ot working-class straight men was by no means universally shared.

In the first halt ot the twentieth century, the eroticization of working-class and criminal masculinity was widespread in gay male communities (Chauncey, 1994; Gardiner, 1992; Herring, 2007). It was an omnipresent feature of queer cultural production in the period, from Jean Genet’s novels to the paintings of Paul Cadmus. Steward and Painter shared the erotic image of “rough trade” as their ideal sexual partner, of which the Painter wrote:

My type . . . were big, tall, heavily muscular virile extroverts, extremely masculine and with all the usual male characteristics ot thought and action of the rough and tumble, devil- may-care type of adventurous, feckless, fiercely independent, strong minded young athlete. They were tough, and had none of the niceties and refinements such as careful dressing and appearance, gentility of speech, behavior or manner.

(LR ,7/12/44)

Steward enjoyed the risks involved in sex with these men—“teasting with panthers,” in Oscar Wilde’s famous words. “Once in a while,” he wrote in the 1947, “the ‘rough trade’ (that means sailors, truck drivers, taxi drivers, and others who won’t do anything with you, who are tough, and whom you take an awful chance with) get rough but 1 love it” (quoted in Spring, 2010, p. 100). Painter was permanently frustrated by the troubles—violence, robberies, blackmail, drugs, and so on—brought by contacts with rough trade. He preferred partners who, while visually resembling street toughs, were well-behaved and compliant in bed, their “roughness” being a carefully cultivated demeanor or merely a hustler’s costume (jeans, sailor’s cap, leather jacket). Painter and Steward repeatedly visualized this figure in numerous photographs and drawings that portrayed sailors, manual laborers, athletes, or gangsters in various homoerotic scenes, as illustrated in Figure 10.1 (Zikratyy, 2013). Steward even transformed his apartment into a brothel-like dungeon decorated with murals ot rough trade in action (Spring, 2011a).

Thomas Painter, untitled photograph, 1950

Figure 10.1 Thomas Painter, untitled photograph, 1950.

Image courtesy of the Kinsey Institute for Research in Sex, Gender, and Reproduction.

Sex with rough trade often but certainly not always involved money. Five dollars (a standard amount in the 1940 and 1950s) was a necessary ingredient in these encounters, as it ensured that the rough-trade partner was indeed heterosexual enough and was doing it “just for money.” To Painter, for example, signs of a partners pleasure in male-to-male sex revealed the man’s possible homosexuality, a highly unappealing quality that ruled out Painter’s desire to have sex with him again. “Unless I have visible evidence that he is the sort of boy who does not want to do it,” Painter wrote, “I’m not interested in having it done. ... 1 must be sure that he is properly all male” (LR,?/06/44). Similarly, Steward’s “particular preference had always been for ‘straight trade’” (Spring, 2010, p. 328). In his unpublished 1942 manuscript, Painter even included a “Blue Book ot Homosexual Etiquette” in which he outlined his advice to fellow rough trade chasers: pay the man a minimum of three dollars, teed him and take care of his other immediate needs, keep your face below the partner’s waist and do not try to kiss him, be suspicious of those who are too eager, never carry lots of cash or submit to blackmail, and avoid minors.

Money, especially if politely disguised as cab fare or a photo model’s fee, to protect the man’s self-image, functioned as a lubricant between buyer and seller. However, the exchange of sex for money between men did not always go smoothly. Muggings, robberies, and extortion were frequent. Painter writes:

I have been robbed pretty regularly and thoroughly at times, in the time 1 have been living here. (Some 2!4 years.) You remember the loss ot my typewriter by a boy named Angelo. He also took a wrist watch. Later a boy who was here only a week—whom Red introduced me to—while 1 was at work cleaned up the place suitcase full. An electric clock (a handsome $15 one), a lot of clothes (mostly old, as 1 never get around to buying new ones), the radio Roger has left here. Johnny R. needed a raincoat one cold, wet night.

I lent him my brand new $25 one. He has never returned it. 1 also lent him $25. I have never seen any ot that either. I ‘“lent” Red $25 to pay fine to avoid going to jail. One boy pretended to understand his price was $10 rather than $5, and 1 gave it to him—such things disgust me more than anger me. Another stole another wrist watch. ... I have never been robbed before my face, or had money taken under threat or duress. But the total of the above probably is large (1 have no intention of adding it up. I hate the whole subject.

I regard the matter as necessary expenses involved in living the way I do. But 1 don’t like it, anymore a man does his wife’s bills for hats and dresses.)

(LR, 21/8/48)

While anonymous cruising in bars, parks, train stations, and beaches was an important part of both Painter’s and Steward’s sex life and oftentimes led to exciting and fulfilling experiences, they met most of their partners through friends and acquaintances. Such arrangements protected queers from dealing with possibly dangerous strangers and ultimately created an underground network whose members shared not only practical tips or pornographic photographs but also contacts with willing and friendly hustlers. Painter writes about one such queer friend, Alan W., who shared his taste for Puerto Rican men and published a small samizdat physique magazine, Chevere, that specialized in erotic portraits:

Visited this photographer friends ot Indio’s again. . . . And in trooped assorted Puerto Rican trade of his, sat around to visit. They were none ot my exact type, but some were near enough to be very pleasant to talk to. He says he has ‘demasiado mucho’ of them anyway and if and when I want some he will be delighted to get rid of some of them— especially in that it seems the ones 1 like best he likes least.

(LR, 25/2/58)

An entry from Stewards diary likewise illustrates how widespread paid sex with rough trade was among his circle and how casually these encounters were arranged with help of other queer men:

On January 16, Red arranged for me to go over to a hotel just south of Roosevelt Road to a truck driver named Bob Clark; he’d had him that morning. Christ, what a sordid dirt)’ little experience. The man was fat, in bed naked in a hot dark room; he couldn’t get a hard-on with my swinging, and finally 1 had to jack him oft—all this tor three bucks, which I left instead of five. That’s the last time I take seconds on one of Red’s tricks in the same day, at any rate.

(Spring, 2011b)

Red Jackson (a different person from the Red mentioned by Painter in the preceding quotation) was Steward’s neighborhood friend who procured willing men to have sex with Steward. Another such friend was Chuck Renslow, a prominent physique photographer. Painter had his own friend circle of photographers-cum-procurers—tor instance, Robert Gebhart (“Gebbe”), whose services Painter used to privately develop and print his own obscene pictures, and the famous “Lon of New York,” who clandestinely sold illicit images (full nudes, including with erections). By the 1940s to the 1960s, many of the physique photography studios operated as prostitution networks, supplying their trusted customers with X-rated versions of their images and contacts with sexually agreeable bodybuilders, as may be represented in Figure 10.2. Some physique models were particularly open and businesslike about the additional services they offered and even ran their own brothel-like establishments. Painter writes about one such model named Arthur U.:

As was the vogue at the time (maybe it still is) the muscle boys were all whores, and so Arthur became one too. I don’t say that like my Puerto Ricans they obliged sexually if approached nicely—they were aggressive and common whores to anyone to do anything. . . . Well Arthur didn’t stop being a whore as almost all other boys do at a certain age (they get a good job, marry or just tire of it). . . . The sex business (and I mean business) is not a hobby; it is another job, moonlighting so to speak. His own apartment is the whore house all the time cluttered with hustlers and/or queers.


Historians have noted not only the importance of physique imagery in the development of twentieth-century queer culture but also the crucial role that queer networks ot physique photographers and bodybuilding enthusiasts played in the consolidation of the gay male community (Waugh, 1996).

Throughout their lives, Painter and Steward had sex with literally hundreds ot men; dozens were regular lovers. These men were a motley crew of “floundering boys,” to use Painter’s expression (LR, 15/4/47). Even it one describes them in the most general fashion as young men of working and criminal classes (laborers between jobs, seamen, immigrant street youth, and so on), the life circumstances that led them into male prostitution varied greatly and so did their

Thomas Painter, untitled photograph, ca. late 1940s

Figure 10.2 Thomas Painter, untitled photograph, ca. late 1940s.

Image courtesy of the Kinsey Institute for Research in Sex, Gender, and Reproduction.

attitudes regarding homosexuality. Both Painter and Steward kept, in addition to a regular diary, detailed indexes of each and every one of their sex partners (Steward called his “Stud File”). These stories reveal a diverse world of rough trade. For example, Painter’s paid partners ranged from those who were clearly repulsed by the male touch to oversexed complete bisexuals who aggressively pursued sex with both men and women. Painter describes one Howie S., of the latter kind:

Despite him being essentially a stupid youth, a rather typical fourth class boxer, he seems to have caused considerable havoc in my life, though not with me. . . . [Our apartment] being what it was, there was one evening when I had Howie, he went into the next room and was fellated by Gerric and into the last room to be pedicated [anally penetrated] by Edward. Bill used to relate that in fellating Howie the first time he would come would be just preliminary. And he loved all ot it: wanted me to pedicate him, to fuck Gerric, and for all I know, tellate Edward. His heterosexual life was equally uninhibited and enthusiastic.


Painter speaks of the havoc that occurred after Gerric K., Painters roommate, married a woman who then quickly abandoned him and moved in with Howie instead. Many of Painters partners were for all intents and purposes straight, but they enjoyed receiving oral sex, not “psychically, but animally, physically” (LR, 22/6/44). Others were “half-queers” who genuinely responded to male advances but were also embarrassed and distressed about them. There were always self-absorbed bodybuilders who got pleasure and pocket money from being worshipped for their muscular physique. Painter wrote about Lou D., a physique model who later went on to become a star of Italian sword-and-sandal movies:

He proved to be the duplicate of the others [‘muscle boys’]. A mirror throws him into an egocentric trance. He wants to be told his pectorals are better than, say, Z.’s (which, I refer you to his pictures, is a great deal). He wants to be raved about and complemented continuously and shamelessly. If you don’t he will prompt you, with direct questions. Incidentally his pectorals are better: they are fantastic.

(LR, 19/4/51)

As many of Painter’s lovers came from immigrant backgrounds, the sexual and gender categories ot their native cultures (southern Italian, Puerto Rican) differed from those they encountered in the United States, complicating the two partners’ understanding ot what men can do sexually with each other and what makes a man queer. The hustlers’ individual personality traits and temperaments were equally dissimilar; some ot Painter’s lovers were sexually compliant but bored and resentful, others “psychopathic” and violent but passionate in bed. The differences among Painter’s rough trade companions could be illustrated by the opposite attitudes of two young men who associated with him in the 1930s and whose first-person testimonies were collected as case studies by psychiatrist George W. Henry. One, Salvatore N., a homosexual, was “disgusted” at the goings-on at Painter’s place, which he described as a meeting place ot “mercenary” male prostitutes. Another, hustler Leonard R., had sex with both women and men. He called Painter “a hell of a swell roommate” but explained that their relationship was “pure friendship” with no sex involved (Henry, 1948, pp. 179, 460).

Having rough trade tor paid lovers could be exhausting, risky, and frustrating, but both Painter and Steward gradually became skilled at developing friendly relations with them. They were good listeners to the often troubled men, sympathetic in their reactions and willing to help at a moment’s notice. Working as a parole officer and a tattoo master, respectively, Painter and Steward had everyday contact with working-class youths and came to value their company over that ot prissy, well-off queers. Writing in 1954 after visiting a clandestine homosexual social club, Steward expounded: [1]

every year, the old one traded in)—and [I imagine him] standing there, cock uplifted, his hands clasped behind his head (fearful that if he should touch me while 1 kneel before him, that some ot my queerness will rub oft on him), and leading me here and there around the room, my following him around the room almost on my knees—and then his final going to the bed, where . . . his head elevated on the pillow, his hands still behind his head . . . we set to work in earnest. . . . [A]t the moment of orgasm, there is only a slight, very slight contraction, a tiny spasm, and a little “oh!” escaping muffled from his mouth, or a small exhalation of air. When I go to spit, I know that by the time I get back he will be up and dressing, his shorts on—and then a final handshake, a promise to call me next week, an admonition to get some new “pitchers” to stimulate him, and off he goes.

(Spring, 2010, pp. 207-208)

In this account, the reader recognizes Stewards pride in associating with “real men” and being allowed to pleasure them. Bob Berbich was an ex-serviceman who held assorted blue- collar jobs over the 16 years he knew Steward: “a sailor, a motorcycle delivery boy, a taxi-driver, a night steelworker, a truck driver and a uniformed guard.” Despite being married and ostensibly heterosexual, Bob had no scruples about being fellated by Steward and certainly enjoyed it; he was a “real man” whose confidence about his masculinity was so strong that sex with queers could not compromise it. Being accepted as a buddy by a working-class tough, if only to a limited degree, delighted and excited Steward, especially considering the stigma and opprobrium he faced among middle-class heterosexuals and even many other queers. One finds a similar sentiment in Painter’s diary when he writes about spending an evening drinking and socializing with two Puerto Rican teenagers at a neighborhood bar: “It was sort of a make-believe evening . . . where I was what 1 would like to be—an accepted buddy and peer with two nice, beautiful, half-naked, friendly boys” (LR, 5/9/53).

The romantic (or even fetishistic) view ot rough trade that one encounters in Painter and Steward had a distinct misogynistic and femmephobic strain to it; femininity in other queers and effete middle-class heterosexuals was a profound turnoff for both men. Benefiting, so to speak, from the working-class culture of aggressive phallic masculinity that permitted men to have an equally active role in sex with women and with queers, Painter and Steward came to inevitably share it to some degree. One may even describe Stewards masochistic submission to straight men as a tortured manifestation of his internalized homophobia. However, there is also an important cross-class dimension to Painter’s and Steward’s erotic vision of the lower classes. Being educated middle-class men (Painter studied to become a religious teacher, while Steward worked in academia for over ten years), they idealized and exoticized the “urban proletariat” as sexually liberated, devoid of the puritanical prejudices and inhibitions that Painter and Steward had grown up with and had to overcome. One can argue that Painter’s and Steward’s sexual diaries reveal intimate, affective histories of the two queer men’s sexual emancipation, in which their pride in transgressing social boundaries and disregarding mainstream conventions combined with the pleasures ot openly expressing and realizing their erotic desires, deemed immoral and pathological by others.

But how “not bound” by social norms and conventions were the interactions that this subset of queer men had with straight hustlers and rough trade? In the next part of this chapter, 1 look at Thomas N. Painter’s sexual diary in more detail to examine the tensions and contradictions around the notions of masculinity, class, and money that defined such relations in the mid- twentieth-century America. 1 explore crucial questions about power, pleasure, and exploitation in male-to-male commercial sex in the period, reconstructing the affective microdynamics of Painter’s relations with his paid working-class lovers.


Writing about My Secret Life, the voluminous sex journal of an anonymous Victorian gentleman who recounts in pornographic detail his sexual relations with innumerable prostitutes, domestic servants, and other working-class women, Steven Marcus addressed a profound question about the role ot the objectification of others in the individual project of sexual emancipation. “Walter,” the author of this famous memoir, was a fascinating if precocious representative of the modern liberal ideology ot sexual freedom and diversity. He rejected the idea of a universal, God-given sexual norm and despised society’s censorship of pornography. He was uninhibited about his desires, consciously fought his own prejudices about sex, and experimented with unconventional sexual practices. “Nothing can perhaps be justly called unnatural which nature prompts us to do,” he argued, anticipating the progressive voices of sex reformers from the next century.

But Walter was a well-to-do upper-class man—most probably, the prominent civil engineer Colonel William Haywood—who was cynical and even brutal in using his power and money to obtain sex (Pattinson, 2002). He treated poor women as always available and ultimately powerless objects to be manipulated tor his pleasure; he spoke of them as a man of his time and class would of horses or hunting dogs. Walter paid to deflower virgins, examined the genitals of his sex partners with a biologist’s curiosity, raped several women who refused him, sexually harassed servants and other subordinate women on a daily basis, and forced prostitutes to enact his extravagant fantasies, however bizarre and dehumanizing. Marcus (1964) argues that this contradiction at the heart of My Secret Life—its author’s impulse ot sexual emancipation being thoroughly tied to a rigid, oppressive system of social inequalities, which he regularly exploits and never questions—is representative of the limitations, perhaps even the failure, of the Western sexual liberation project. As more recent discussion ot race and sexuality has also shown (for instance, in the analysis of racism in gay male communities), most liberated forms ot sexual behavior can comfortably coexist with most backward racial prejudice or dehumanizing tetish- istic fantasies. “It may be useful to remind ourselves,” emphasizes Marcus, “that the struggle for sexual freedom, at least in the lives ot individual persons, requires considerable stepping over the bodies ot others” (Marcus, 1964, p. 159).

One can identify obvious parallels between My Secret Life and the homosexual autobiographies of Thomas Painter and Samuel Steward: the view of members of the lower classes as sexually uninhibited and available, as well as the crucial role of money in facilitating sexual relations with them. There is an important difference, however: Painter’s and Steward’s partners were working-class men, not women, at a time when sex between men was socially proscribed, highly stigmatized, and downright illegal. In My Secret Life, the vector of power relations is brutally clear. It is directed from the aggressive phallic potency of Walter toward objectified and fragmented bodies of servant girls and prostitutes, whom he repeatedly abuses. The power dynamic of queer men’s relations with straight hustlers was much more complex. Hustlers and rough trade, who usually were heterosexual working-class men, physically strong and streetwise, did not occupy the same subordinated and powerless position in paid sex as did the poor women of My Secret Life, especially vis-a-vis their queer clients, whom they considered weak and womanlike. Presenting Steward’s understanding of his lifelong relationships with male hustlers, Justin Spring explains:

The roles of hustler and customer were at that time defined in a way that was entirely to the physical, psychological, and monetary advantage ot the hustler. In this well-established exchange, the hustler (who was understood to be primarily heterosexual) allowed the homosexual customer to perform oral sex on him. That was all. There was no exchange of affection, no variety, and no reciprocation. As a result, the hustler retained his heterosexual identity', asserted physical and emotional dominance over the homosexual client, and at the same time profited financially from what was to him an inconsequential (and basically pleasurable) sensation.

(2010, p. 299)

The hustlers’ advantage was certainly limited, as they were subject to the objectification and fetishization ubiquitous in sex work and did not always experience sexual advances from men as innocuous and inconsequential. The position of their queer clients was similarly twofold. Money allowed queers to obtain sex from underprivileged and marginalized young men, often from immigrant groups or racial minorities, but the stigma of homosexual “perversion” and the risk of legal persecution for sodomy or corrupting minors made them at the same time easy targets for extortion, blackmail, robbery, and assault. One can argue that queer-hustler relationships were an arena of conflict and negotiations between different vectors of privilege and oppression (economic, class- or gender-based, racial, generational) in which neither party could completely get the upper hand. The autobiographical testimonies of Thomas N. Painter reveal and articulate these conflicts.

The impossibility of reciprocity in homosexual relations is an overarching theme in Painter’s diary and memoirs. In his view, queers wanted only straight men who were unable to genuinely respond to their desires, and money was an unfortunate but necessary way of resolving this deadlock. Among miscellaneous memorabilia included in Painter’s archive at the Kinsey Institute, there is a short poem, “Broadway Love. Homosexual,” which ends with the following lament:

Hell was at its most fiendish moment

When it devised a heart full of and hungry for love

Then twisted the mind and body thus endowed so it must not find end to its yearning. And finally put in the same world glorious boys Who will imitate the Goal, willow-the-wisps,

For a time, for money. Then are gone.

And we see ourselves merely In a choking mire. Alone.

Written in 1935, it reflects Painter’s frustration at his first experiences in New York’s gay underworld and echoes homophobic cultural discourses of the time in which queers figured as “sad young men”—pallid sickly youths, driven to death or suicide by their “perverse” desires (Dyer, 2002, pp. 116—130). Gay life, as Painter saw it at the time, was a life of loneliness; onesided infatuations with murky characters; and hasty, dangerous, and generally unsatisfying sex. Nearly 40 years later, organizing his writings for a future biographer, he wrote a short essay titled “Long Search” that highlighted his lifelong pursuit, often sidetracked and by and large disheartening, of reciprocated intimacy and companionship with men. The essay concludes with the section “1963—1968. Search Fulfilled.” It is devoted to his last boyfriend, Gilbert, who was at last able to accept Painter as an equal partner and who fully enjoyed physical intimacy with him. “I became a ‘companion,’ I find myself completely needed and useful, I find reciprocated love, response, as never before,” Painter declared. The pathos of this statement emphasizes the frustration and disillusionment he felt with many of his other partners, whom he found to be mercenary or physically cold. Poignant passages like the following from Painter’s diary reveal the intimate, emotional side of sex with hustlers:

Speaking of curious sensations. The last time Carmine was here, as we were about to leave and both were fully clothed, for the street, and he was standing there, 1 felt an impulse and went up to him and ‘“hugged” (embraced) him—rubbing my face and mouth against his neck and ear. This was an impulsive expression of affection, of the purest sort. And as 1 did so 1 felt the constriction of my throat which comes in deep emotion (related to weeping). And 1 felt the emotion too, instantaneously—for about five seconds, 1 guess. Then he responded by placing his arm around me—routinely, in the utter minimum ot response suggested to my action. At this point 1 had the reaction: I could have wept, raged, or laughed, as 1 did, a sort ot bitter, ironic half-laugh, as if to say “I should have known better than to give way to my affection to this paid boy who can’t, and couldn’t possibly, respond any other way than he did, but who did what he felt was required, in his own lazy, half-hearted, boy way.”

(LR, 7/5/53)

Painter could not escape the homophobic social climate of the time and ultimately regarded his homosexuality as a curse and a handicap. In his resigned view, the only relationship a queer could hope for was inauthentic and sordid love for pay. “And to those who cannot even buy / They may stand and dumbly want / Or they may haggle and cheat / Or they may weep, dry tears,” Painter wrote in “Broadway Love: Homosexual.”

In modern societies, money has been a widespread and effective means of asserting one’s dominance. Giving money to others, especially those in dire circumstances, can also produce an immediate, and thoroughly false, sense of intimacy. It is therefore no surprise that, being at a disadvantage in their relations with hustlers and rough trade, queer men like Painter resorted to using money to smooth out the tensions inherent in their attraction to working-class straight men. Within the rigid system ot asymmetrical sex roles adopted by many at the time, homosexual men were regarded exclusively as submissive partners obliged to sexually service others. They occupied a woman’s (or more specifically, a prostitute’s or an “easy” woman’s) position in the working-class hierarchies of gender. Money and other attributes of higher social status allowed queers, otherwise treated as proxy women, to express masculine dominance in their interactions with working-class men and exercise some degree of control when buying sex from them.

In 1964, responding to the sex researcher John Gagnon, who asked Painter why he had always paid men for sex instead ot finding a reciprocal and financially equal relationship, Painter provided a straightforward answer: “Non-paid 1 must please him. To do so I must fellate or be pedicated neither of which do 1 enjoy. ... So I want to pay and command” (LR, 1/2/64). This statement is unusually blunt for Painter, who typically devised more elaborate and nuanced rationalizations tor his actions, but it reveals his lifelong perception of money as an always- available resource with which one could obtain whatever one wanted from other people. Born into the upper-middle class, Painter described himself as growing up in “complete disregard of money,” considering it “some sort ot token stuff that you passed people when you wanted something” (LR, 20/11/62). As Painter quickly spent all of his family’s tortune in the 1930s and in the following decades led a rather impoverished existence working as a parole officer and then as a bookstore clerk, this idea ot money as a means of dominating others became to him less a fact of his everyday life than a powerful component of his erotic imagination. In fact, Painter singled out “forcing sex on an unwilling person ... by giving (or withholding) money which he needs” as one of the predominant themes of his homoerotic artwork (LR, 8/5/66). Many of his pornographic drawings depict scenes of domination and sexual servitude in pseudo-historical, sword-and-sandal settings: tor instance, a powerful ruler is offered captured enemy soldiers or newly purchased slaves, whom he orders to be stripped naked, tortured, and raped while he oversees the process (Zikratyy, 2013). Painter admitted he was excited by such sadistic fantasies of absolute control over another man’s body and its unrestrained violation, but he never attempted to recreate those fantasies in real life (unlike Steward, he was not interested in sadomasochistic play).

In Painter’s biography, the nexus of sexual domination and economic coercion took a softer, more indirect form of cross-class sexual patronage—a Horatio Alger—style scenario of a wealthy, educated man raising a slum boy to middle-class respectability in exchange for companionship and occasional sexual favors. Painter writes about his ideal relationship:

My “daydreams,” my erotic fancies however are all with me wholly dominant. Over strong, independent spirited, muscular, dominant youths. My dominance, in these situations, arises from vast wealth and power, which 1 exert to rescue and raise them from the most extremely low and desperate social situations—intense poverty, slavery, imprisonment, threat of death. Thus 1 can be dominant, in a way, while allowing them to be dominant personalities at the same time. They need me unequivocally, due to their situation . . . and 1 need them for their sexual attraction and to need someone to help, who needs me. Eventually, due to living with me (the rich and powerful person), they become educated, sophisticated, suave and able-to-take-care-of-themselves-very-well-thank-you—and 1 release them and find another who needs me.

(LR, 9/2/66)

This vision of mutually beneficial cross-class and cross-generational friendship with benefits was crucial to Painter’s understanding of homosexual relations. It was a humane, even noble solution to what he saw as his sordid sexual predicament—his “unnatural” attraction to men who by definition could not reciprocate his feelings. Painter’s professed goal was to befriend and mentor underprivileged young men involved in prostitution to queers, and other delinquent activities, and to help them reform and make an honest living. Putting aside Painter’s genuine attempts to help his lovers, who often found themselves in trouble of one sort or another, one can clearly recognize in this “daydream” his desire to maintain dominant status in relationships by asserting middle-class masculinity and its values (responsibility, self-control, education, duty, service) over the rough, uncivilized, animal-like virility of the lower classes. In this philanthropic scenario, the submissive, humiliating position in which a queer partner was placed during the sexual contact itself—being forbidden caresses of any sort and allowed only to orally service the hustler, his own pleasure unimportant—was compensated by the economic power he could exercise in nonsexual spheres of life.

Painter enjoyed situations in which he felt respected, was treated as a trusted confidant, or was asked for help or advice. His Puerto Rican lovers showed particular regard for his status as an older, white, educated “Americano.” His regular financial benefactions to them—some of them genuine gestures of help, others more pragmatic transactions—made him feel, for a time, like an affluent foreign guest toward whom everybody is uniformly friendly and compliant. The fact that as a queer man Painter remained vulnerable to public opprobrium, violence, and blackmail prevented him from becoming as ruthless and exploitative as the author of My Secret Life. In Painter’s life, money was one of the few resources and privileges available to someone who was otherwise considered a sick and dangerous “pervert.” It therefore served as the only available—but ultimately precarious—negotiation card in arranging sex with rough trade, who were nearly always worse oft than Painter economically but arguably held more power as straight and physically strong young men.

What could money buy Painter? First of all, companionship. A long-term “kept lover” would join him during social outings or vacations; a horny straight soldier whom Painter had picked up on Coney Island would stay overnight, having no other place to go; a group ot Puerto Ricans would join him for a picnic. It is important to stress how lonely life could be for a middle-aged homosexual man at the time and how rewarding even such simple social activities were to Painter. In these situations, money operated in a manner consistent with the longstanding working-class-leisure notion of “treating” as courtesy between men and a respectable way to gain and secure a woman’s company. Since at least the mid-nineteenth century, workingmen treated each other to rounds of beer in male bonding rituals and treated their girlfriends to dancehall outings and new dresses in exchange for sexual liberties (Peiss, 1986). To many of his lovers, Painter became something of an eccentric older hanger-on whose company was tolerated and maybe enjoyed so long he paid the expenses and supplied pocket money. At times, groups ot cash-strapped young men formed around Painter and used his apartment as a place to spend a night and make a few dollars. About one such group, Painter wrote:

The boys now have developed a special meaning of this in reference to me: one has or has not “joined the union” depending on whether or not he has been to bed with me. There was some comment in the car that Perez has joined the night before, and veiled speculation as to whether Indio would that night, as he now was the only non-union member of the group. This all in the spirit of good clean fun, in a kidding, humorous manner.

(TR, 15/7/55)

Painter remarked that, unlike other queers who limited their interaction with rough trade to sexual transactions, he got genuine pleasure from socializing with his working-class sex partners. Part ot the explanation lies in Painter’s voyeuristic desire to observe them during everyday activities; Painter particularly enjoyed watching them when they were seminaked in the summer.

On the other hand, in nonsexual interactions, Painter could behave as an older friend and mentor and assume a dominant masculine role unavailable to him in sex with these men. This is how Painter described his relationship with his lover Efrain: “I hold the unique position ot receiving the intimate confidences and the willing cooperation in answering my questions of a boy whom no other educated, upper-class person could even approach. (Not even as a queer, as he loathes them)” (LR, 7/10/60). He further explained:

I am sure that part of my pleasure in Efrain is in his very dangerousness—and the fact that I can sit by him and stroke his hair and talk soothingly—and he will smile his nicest back at me. . . . Like having a pet panther who slashes anyone but purrs for me—I keep trusting.

(LR, 24/11/60)

The pleasure and pride that Painter felt in this exceptional status, however illusory, were twofold. He asserted his middle-class superiority over the powerful but unbridled masculinity of working-class youth; he called himself a “wild animal trainer.” And through his proximity to the lower classes and their authentic, natural virility, as Painter regarded it, he grew to see himself as more masculine as well. For Painter, this masculine rejuvenation in the slums— a long-standing practice among middle-class reformers and philanthropists (Koven, 2004;

Murphy, 2008)—counteracted the ubiquitous feminizing medical discourses that portrayed queers as quasi-women.

Another thing that money could buy Painter was of course sex itself, but the physical dimension of his relationships with hustlers and rough trade was also the most intricate. While many queers enjoyed the submissive position afforded to them in sex with straight men, Painter found it unsatisfying and repulsive; it undermined his masculine self-image. He avoided penetrative sex, in part because it presupposed a clear-cut hierarchy of roles, and instead enjoyed more neutral caresses, frottage, and mutual masturbation. Individual factors probably played a major role in how different men responded to Painter’s sexual requirements. Some enjoyed an easy client who simply “worshipped” their body and did not expect them to do much; others were uncomfortable about any form of male touch outside of the strict protocol of unreciprocated anal and oral penetration; yet others were disappointed that Painter did not have “real sex” and did not give them the pleasure they expected. This is how Painter described the sexual mores of the young Puerto Ricans who became his frequent paid lovers in the 1950s and 1960s:

The Puerto Rican boy is not only willing but eager tor sex with a male . . . but he expects pedication [anal penetration], to be the pedicator. . . . Hence when they encounter my requirements they undergo several reactions: (1) they find they are not going to get detumescence [sexual release], which is [a] serious disappointment and frustration for them, as they are all in a terrific state of sexual starvation. (2) They find themselves called upon to allow me to make love to them, especially involving body and face, by my hands and mouth. This (as noted above) is, generally, foreign to their experience. Moreover it is psychologically repugnant: instead of being the dominant, aggressive, primitive pedicator, they become the passive object of my sexual attentions. Bad enough, but I want them, if they will, to make love to me—to embrace, intertwine, even kiss me. This is wholly foreign and seems homosexual to them, making love to a man, or even having him make love to them.

(LR, 2/5/56)

Painter was something of a muscle fetishist fascinated by public displays of the seminaked male body (on the beach, during exercise, at labor). He was attracted to a well-developed physique in men, especially in their upper body. His sex partners often found themselves in an ambiguous position of being elevated to a demigod-like status while at the same time treated as cardboard mannequins whose only valued characteristics were their “splendid pectorals,” “bulging biceps,” and “fantastic latissimus dorsi.” The rapid growth and visibility of the bodybuilding subculture in the postwar years introduced into American society—through beefcake magazines, sword-and-sandal movies, and Mr. Universe competitions—a new image of the young muscleman as an object of desire. But this newly sanctioned celebration of the male body remained a contested area, where more traditional ideas about what makes a man (dominance, action, a strong mind) clashed with his feminizing objectification. One sees this conflict clearly in the reactions of Painters sex partners to his erotic worship of their muscular physique. There often appears to be a kind of narcissistic cockiness in the way they were ready to display their naked body for a queer’s lustful gaze, combined with an unease, sometimes rather profound, about being essentially treated as a two-dimensional sex object, as seen in Figure 10.3.

The ultimate arena of conflict in Painter’s sexual relations with hustlers and rough trade was ethical. Suspicions ot moral corruption and sexual exploitation hung over such relationships— a middle-age man coaxing underprivileged youth into sex for money—in part owing to homo- phobic media representations of queers as child molesters and serial killers in the 1950s and

Thomas Painter, untitled photograph, 1950

Figure 10.3 Thomas Painter, untitled photograph, 1950.

Image courtesy of the Kinsey Institute for Research in Sex, Gender, and Reproduction.

1960s, in part a result of their inherently problematic circumstances. The broken-home backgrounds and troubled behavior of some of Painter’s lovers, who were often unemployed, homeless, or involved in petty crime and street gangs, both made them more willing to sell sex to queers and made this sexual-economic exchange ethically challenging, as it was essentially a form of survival sex. A romantic person with religious background, Painter tried to negotiate in his mind the conflict between his masculine pleasures at easily possessing these young poor men’s bodies and his middle-class scruples about exploiting others’ dire circumstances in so sordid a manner. In the summer of 1961, he wrote a short essay called “Moral Code” in which he described the ethical dimension of paid sex and articulated his own attitudes about it:

Living a life of paying for sex with teenage underprivileged boys makes tor thin ice skating on the “coercion for money” part of [the moral code], 1 have always avoided it when

I sensed it, have only had boys who were perfectly willing and in no sense unhappy about it. ... 1 have always verbalized my approach and taken no for an answer at once, without discussion (even it they didn’t mean it, as it later developed). 1 have never used stimulants (erotic pictures) or drugs (alcohol) to “make” a boy. Frequently 1 have been so careful and hesitant and sensitive that the boys have been vaguely irritated. 1 have tried to minimize, in the sex act, my role down to necessity, never be greedy or boring or demanding. 1 stop at any slightest sign of disapproval of any detail. 1 try, as you know, to be friendly and interested in the person, fair in my dealings, respectful of their dignity as persons, sensitive to their feelings and attitudes.

(Painter, 1961)

This passage is clearly self-justificatory and not thoroughly truthful in its details (Painter did show his sex partners pornographic pictures on more than a tew occasions, according to his own diary), but it reveals his genuine preoccupation with the ethics ot paid sex. Interestingly enough, the essay was written during the time in Painter’s life when he himself felt exploited and abused by rough trade. Just two months earlier, in May 1961, he had been raped by the aforementioned Efrain, who, according to Painter, showed no sexual desire tor anal penetration at all and did it only to humiliate him. Seeing his life spiraling out of control as Efrain and his gang of “Dragons” took complete control of his finances through violence and blackmail, Painter suspected that he, in a way, had brought these troubles upon himself by coaxing poor, socially marginalized teenagers to be his paid lovers. In his diary entries from July 1961, Painter talks of still being shaken by his memories of Suddenly Last Summer, a Tennessee Williams movie he’d watched a year before, whose homosexual protagonist, Sebastian, dies at the hands of Spanish street boys whom he was blatantly buying for sex during his summer vacation. He could not help but wonder whether he was going to end up like Sebastian, who, despite being “obviously brilliant and talented, was at the end devoured by the half-wild boys he chose to devote himself to” (LR, 24/1/60).

In the “Moral Code” essay, Painter mournfully described his sexual biography as “forty years of paying underprivileged boys for sex.” Painter’s preoccupation with the impact of his actions on the lives of these men—was he helping or spoiling and corrupting them?—had been present in his autobiographical writing since the 1930s. In his archive, he preserved a brief one-page note written by one Charlie O., a typical street tough, a Jersey City gang member who was involved in many robberies and even a murder, went to prison tor burglary, and was, at one point, addicted to heroin. On meeting Painter, who took a special fancy to him and encouraged him to make an honest living, Charlie resolved to go back to work as a merchant marine and returned to the sea in the spring of 1935. His note to Painter from June ot that year reads:

Dear Tom

am doing very nice with my job, and just can’t wait till the ship leaves. I did not think that it was so easy to work for a living, but I have you to thank for that. I have received my first pay yesterday, then went up town to pay Bill [Painter’s queer friend] the money I owed him, we had a few drinks then had dinner, then we—.

By preserving this letter among his personal memorabilia as well as underlining the sentence, Painter wanted to communicate to future readers of his “Life Record” how he sought to positively influence his delinquent lovers and at times succeeded in reforming them; as late as 1967, he still described his friendship with Charlie as his “greatest success in helping someone” (LR, 14/8/67). This letter also served as a proof that, while true physical reciprocity was perhaps impossible in paid sex between queers and rough trade, their relations did not necessarily involve coercion and exploitation but could instead resemble regular, nonsexual friendship. Charlie is mentioned repeatedly throughout Painter’s diary as an example of someone whom society viewed as immoral and criminal but, when approached with sympathy and understanding, turned out to be kind, loyal, and grateful. Even when Painter went broke in February 1935 and was quickly deserted by his other lovers, Charlie remained, living with him, and years later, after receiving a large insurance settlement tor a work trauma, he gave some money to Painter in an attempt to compensate him for his previous help. The last incident especially reaffirmed Painter in his belief that queers could “love their boys, not just suck their semen” and that “the boys will, in their fashion, respond with friendliness and liking, some of them” (LR, 27/5/63).

“Some ot them” is a key phrase here. Charlie was a rather exceptional figure in Painter’s sexual biography, which was largely populated by either rough and sinister characters who ruthlessly exploited Painter’s attraction to them, at times resorting to robbery and extortion, or “glorious youths” who, even if sexually available tor money, showed little amiability and affection and naturally had no interest in establishing romantic relations or friendships with older queers. Furthermore, despite Painter’s idealistic pronouncements about the positive role that he wanted to play in the lives of his working-class lovers, the effects of his paying them for sex were often demoralizing, and they often used the money they obtained from Painter to support a desultory semicriminal lifestyle of drinking, gambling, and drug use. Painter regularly pondered this issue, very much like the social reformers of the time who wondered whether dispensing money and material goods to the poor had any positive impact on their life situation or it it merely made them idle and dependent on charity.

The dangers of spoiling young lower-class men with his money, instead of reforming them, were obvious to Painter, for instance, in his relationship with Peter D., who was his “kept” boyfriend in 1939—1941. Peter was one ot the “Depression boys,” as Painter called them; he came to New York from the small industrial town ot Palmerton, Pennsylvania, where his Ukrainian- immigrant parents worked in a zinc mill. Painter saw in Peter a “nice boy” who needed to be rescued from the underworld of male prostitution, where he’d ended up owing to economic hardship, not some inner depravity. Painter attempted to socially elevate the young man who, according to him, “acquired a hatred tor books, school and reading in general, and tor everything connected with learning,” having been raised by poor and backward parents (LR,?/12/44). As Peter was unwilling to devote time to what Painter called “self-improvement” and, it seems, rather put off by Painter’s overtly patronizing and possibly humiliating manner in insisting that he did so, hardly anything came out of Painter’s “educational” efforts. A series of letters that Painter received from a friend of Peter’s in 1941 suggests that the effect of Painter’s relationship with Peter was harmful and turned the young man into a complete loafer without any serious goal in life. Peter’s friend wrote: [2]

[Peter] told me, that he really wanted to do something constructive for himself, and that pleased me very much. Ned [another triend] told him, before leaving, that he would assist in obtaining him a position. Ned has kept his word, he’s even worried himself sick over it, but La Peter has shown a definite lack of interest. . . . It’s apparent—that he doesn’t want work. ... So the kid—is just drifting along. Gets up in the afternoon, about one o’clock, usually spends couple of hours before the mirror, then takes a little stroll, has a lovely dinner, the price of which is of no consequence. Takes in a movie, the price, still of no consequence. Then he goes to bowl, in an alley, the location ot which, I definitely don’t like. It’s on North Miami Ave. And long about, two or three in the morning, he comes strolling in, makes a careful toilet, and goes to bed. That has been going tor days and days.

We both know—that it was partly your money, that brought about such a state of mind. . . . And I for one, would appreciate your taking him in hand, and try and mold him into something—very different.

The situation depicted in this letter was a far cry from Painter’s ideal ot helping an economically underprivileged lover to establish himself in life. Instead, it exposes the negative effects that “keeping” a straight young lover could entail. Peter’s conflicted feelings about his relationship with Painter—Peter clearly enjoyed the financial opportunities it afforded him, demanded more and more money, and flaunted luxuries, but he remained averse to physical intimacy with Painter (and other men) and was ashamed about being his “kept boy”—further complicated the case and eventually led to their separation. Later in life, Painter regretted ever starting this affair and described it as “a horrible, complete waste of time, opportunity, money and everything else” (LR, 24/9/67).

In his diary, Painter expounds on his repeated romantic disappointments, like the breakdown of his relationship with Peter D. and other troubles caused by his association with hustlers and rough trade. On numerous occasions, he expresses his exasperation at being taken advantage of by the “mercenary” youngsters he pursued as sex partners.

Pete has no faintest conception ot friendship or affection or appreciation: he uses me tor his convenience, as a comfort station, a flop, a refuge, and a source of small contributions of cash in emergencies—but never has he come around without wanting something. Social and friendly intercourse are beyond his ken. . . . He has no friends—as none of these people do—merely companions who are temporary useful and convenient.

(LR, 14/9/52)

This passage describing another Peter, a teenage “hustler and clip artist” who briefly lived with Painter in 1952, illustrates Painter’s usual grievances about the paid lower-class lovers who turned out to be immature, unreliable, insensitive, ungrateful, opportunistic, unscrupulous in financial matters, or dangerously violent. Besides giving vent to romantic frustrations, these negative judgments reveal a profound conflict at the intersection of sex, class, and money that gave rise to the misunderstandings and fallings-out that beset Painter’s sex life.

To fully understand this conflict, one needs to approach Painter as a modern middle-class subject who shared the new liberal notion of sex as consensual physical intimacy, whether romantic or purely recreational. Painter was, in a broad sense, a competent consumer able to safely navigate the underground sexual marketplace. Painter’s attitude was egalitarian and transactional, and arguably thoroughly capitalist: two free individuals agree, via respectful negotiation, on a mutually beneficial exchange of sex for money. The modern capitalist logic of sexual contracts that enabled and shaped masochism as one ot the paradigmatic modern “perversions” (Deleuze, 1991) equally served Painter the homosexual in resolving the deadlock ot queer desire toward straight men. The cultural matrix of economic exchange made “impossible” relations (domination by a woman, sex between men) possible within the preestablished limits of articulated or implicit contract. All in all, Painter’s preferred sex partners were safe and easy- to-deal-with “nice boys,” a category he used to describe paid or kept lovers who were reliable, considerate, and uncomplicated in their sexual dealings. Many bodybuilding models belonged to this group:

“Muscle boy” means the real weight-lifting, pictures-in-the-magazine set, mostly, it developed from the Brooklyn YMCA gym, where they all knew one another. . . . They were all, as opposed to the hustlers, boys living at home, going to school (and even college), honest, non-delinquent, otherwise decent and well-behaved boys. One had their telephone numbers and made appointments if they were not home—“to pose for me.” They used the photographs as proof.


As active participants in the sexualized market of mail-order physique photography, these muscle boys were already familiar with the rules and workings of sexual-economic exchange. Their attitude was both courteous and businesslike: they appeared when called for, performed agreed-on sexual activities, collected their fee, and left.

However, what Painter encountered among more socially and economically marginalized young men was a view of sex not as mutual exchange but as an arena tor asserting one’s phallic dominance over the weaker and inferior partner, be it a woman or a queer man. Tensions inevitably arose as Painter found his middle-class masculinity devalued and undermined within such hierarchic relations. He aimed to remold these partners according to his middle-class ideal of philanthropic mentorship, but the subordinate role of dependent protege was equally emasculating to these young working-class men, who would inevitably try to compensate for it, often through violence. Such young men often perceived male sexual pleasure not in modern terms of mutuality and consent but as organized around physical domination and the aggressive pursuit of genital relief. As such, it was fully reconcilable with violence and exploitation. As historian Matt Houlbrook argues:

In sliding between intimate friendship and brutal assault, workingmen’s encounters with the queer transcended contemporary understandings of “homosexuality” or “homophobia.” Intimacy, sex, blackmail, theft, and assault constituted a continuum within the same cultural terrain, underpinned by dominant conceptions ot masculinity as toughness and resourcefulness. . . . Men played roles that reproduced a difference from their sexual partners, articulating a toughness that asserted their physical and moral superiority.

(2005, pp. 178-179)

Painter’s relations with hustlers and rough trade were in a way a continuous power struggle around the changing, class-conflicted notions of masculine dominance. And like every power struggle, the struggle was open to erotic possibilities that energized and perpetuated it. The rough styles of masculine expression, culturally legitimized in the working-class and underworld milieus, were Painter’s lifelong erotic fetish, but they also remained a source of danger, frustration, and disappointment, as they clashed with his own masculine self-image and his middle- class values and ideals.

Buying sex: then and now

Painter’s affluent New England family shunned him; after graduating from the Union Seminary, he was denied every teaching job because of his “problem,” and his upper-class friends refused any contact with him. Ultimately, buying sexual services from other men, especially those who were at the same time hypermasculine and economically vulnerable, allowed Painter to compensate for the powerless and abhorred position he found himself in as an openly queer man. Commercial sex allowed Painter to temporarily enjoy the fantasy world of sexual plenty (New York of the 1930s through 1960s had a bursting underground of male sex work) and sexual subservience (even the most tough-looking straight man could be transformed into docile sex object for an hour) and thus, in a way, repair his damaged sense of manhood.

What Painter desired as his ideal relationship with a young working-class straight partner is familiar to us today as “the boyfriend (or girlfriend) experience,” a commercially based transaction that exceeds mere genital relief and offers some kind of emotional connection to the client, however limited or temporary. This type of relationship has recently attracted scholars’ attention as a form of sexual-economic exchange that values genuine connections with otherness (as in the “authentic” experiences offered by tourist destinations and foreign cuisines) but also thoroughly commodifies and thus fully contains them (Earle & Sharpe, 200S; Sanders, 2008; Milrod & Monto, 2012). As studies show, the client’s and the sex worker’s experiences of these relations often differ strikingly: the client indulges in the fantasy of mutual intimacy and appreciates the seemingly genuine warmth and friendliness of the paid partner, while the sex worker carefully and consciously controls the emotional boundaries of the encounter (Peniston & Erber, 2007). The insightful theoretical notion of intimate or emotional labor (Boris & Parrenas, 2010) captures these new postindustrial economies of commercialized eroticism. But how new are they? I would argue that the relations that some queer men had with hustlers and rough trade were, in a way, a prototype of this new post—“sexual revolution” framework of intimacy and commerce. Queer men who actively participated in urban sexual underworlds, like Painter or Steward, explored new modes of relating to others outside of the socially sanctioned domains of work and domesticity. Their firsthand testimonies reveal their ingenious strategies of using money and the cultural capital of middle-class consumerism to bypass multiple conflicts around masculinity and same-sex desire and ultimately to lead plentiful and exciting (if frequently frustrating and dangerous) sex lives.

One way to look at the erotic universe captured in the voluminous sexual diary of Thomas N. Painter is to see an archaic system of gender identities and sexual roles in which straight men were “not quite straight” and could be cajoled into allowing another man to perform oral sex on them. This centuries-old world of flexible sexual orientation remains fascinating today, as the ideologies of gender are undergoing a dramatic transformation under the influence of trans and nonbinary movements. But an equally important revelation from Painter’s “Life Record” is the complex admixture of intimacy and commerce enabled by urban capitalism that allowed new relations to emerge and develop between men. The tropes and formulas of consumer capitalism and the service economy provided a blueprint for a variety of informal semi-underground networks and connections that enabled commercial sex between men. Sites of mass public leisure (bars, pools, beaches, public playgrounds), the mail-order consumer industry, emerging public representation of male nudity, and new technologies of image-making and reproduction all became vital ingredients in shaping modern gay subcultures. In reading the diary ot Thomas N. Painter, a self-identified queer man and a lifelong client of male sex workers, one encounters a rich firsthand illustration of a central thesis of the social theory of sexuality—the profound connection between capitalism and gay identity (D’Emilio, 1983).


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Male sex work in comics and graphic novels

  • [1] hate bitch parties ... I tolerated [tonight’s] better than usual, however, for at the end ofthe evening I knew there lay waiting for me . . . Bob Berbich, the lanky truck-driver withhis skull-like face, his body in which each muscle stands out, with the skin of the workerwho never has the time to seek out the sun and who retains the winter whiteness all yearround. . . . [He has been] faithful all these years, with his poor grammar, his limited view,his total and utter absence of “culture” in any form, his proletariat pleasures (a new car
  • [2] am really concerned about [Peter’s] attitude and mental outlook, on things in general.Having known Peter before you, 1 feel 1 am in a fairly good position to note the amazingchange that has come over the kid. . . . He has lost all sense of values, both in money, and people. He doesn’t seem to realize, whohis real friends are, and if he did, not particularly impressed with the knowledge. ... As1 see it, Pete wasn’t mentally equipped to keep up with the pace, that he has traveled thispast year. His life for the past year, has been one beautiful vacation, after the other. He actsexactly like a movie star, who actually believes all the things that are said about them. Inthe house, on the street, he always seems to be conscious of himself.
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