The Boys of Fairy Town: Sodomites, Female Impersonators, Third-Sexers, Pansies, Queers, and Sex Morons in Chicago's First Century

The Boys of Fairy Town: Sodomites, Female Impersonators, Third-Sexers, Pansies, Queers, and Sex Morons in Chicago's First Century

by Jim Elledge


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A history of gay Chicago told through the stories of queer men who left a record of their sexual activities in the Second City, this book paints a vivid picture of the neighborhoods where they congregated while revealing their complex lives. Some, such as reporter John Wing, were public figures. Others, like Henry Gerber, who created the first “homophile” organization in the United States, were practically invisible to their contemporaries. But their stories are all riveting. Female impersonators and striptease artists Quincy de Lang and George Quinn were arrested and put on trial at the behest of a leader of Chicago’s anti-“indecency” movement. African American ragtime pianist Tony Jackson’s most famous song, “Pretty Baby,” was written about one of his male lovers. Alfred Kinsey’s explorations of the city’s netherworld changed the future of American sexuality while confirming his own queer proclivities. What emerges from The Boys of Fairy Town is a complex portrait and a virtually unknown history of one of the most vibrant cities in the United States.

Product Details

ISBN-13: 9781613739358
Publisher: Chicago Review Press, Incorporated
Publication date: 06/01/2018
Pages: 312
Sales rank: 592,037
Product dimensions: 5.90(w) x 9.10(h) x 1.10(d)

About the Author

Jim Elledge is the author of twenty-four books. His most recent nonfiction book, Henry Darger, Throwaway Boy: The Tragic Life of an Outsider Artist, received the Georgia Author of the Year Award in biography and was a finalist for the Lambda Literary Award and the Randy Shilts Award for gay nonfiction.

Read an Excerpt


Took Him Home with Me, and Love Him Better Than Ever

Monday is a sort of dull day with me always — not because of my having any[thing] to do with the females — because the good lord knows that I do nothing of a kind.

TRUTH BE TOLD, John Wing was a sodomite.

He was also a devoted diarist, having begun keeping a journal when he was thirteen. He grew into a man with fine features and "fair" complexion. He was five feet, seven and a half inches tall, his light blue eyes were piercing, and his mustache was as dark brown as his hair, neatly trimmed, and thick. He dressed to the nines in top hat and coat and had a penchant for diamond stickpins — and for younger men. "Diamonds are my delight," Wing wrote in his diary on Saturday, September 23, 1865, and then added, "diamond pins or diamond friends, in the shape of whole soulded boys."

Born in 1844 and raised on a farm just outside of Pulaski, New York, Wing dropped out of school at sixteen to become a "printer's devil," performing menial tasks for a local newspaper, the Pulaski Democrat. Over the next five years, he worked on the staffs of three newspapers and as a teacher at two schools — all in upstate New York. He also read every book he could get his hands on and began building his personal library. As the Civil War wound down, Wing decided to go west to seek his fortune. He had just turned twenty-one years old when he boarded a steamship that sailed through the Great Lakes, stopping at Cleveland and Detroit, where he looked for employment — unsuccessfully, as it turned out.

Wing returned to the ship and traveled to Chicago, arriving on June 4, 1865, a sweltering Sunday two months after Robert E. Lee surrendered to Ulysses S. Grant at Appomattox Court House. As he walked down the gangplank, Wing carried a valise of clothing in one hand and a parcel of his diaries in the other. His library was in crates. He found lodgings in a rooming house, and the next day he called on the editor of the Chicago Tribune and asked him for a job as a reporter. He was hired on the spot and would live in Chicago for the rest of his life. At first he boarded in various rooming houses, but by 1866 he began living in hotels, among them Brigg's House at the northeast corner of Wells and Randolph Streets and the Shepard Building at the southeast corner of Dearborn and Monroe Streets.

Considered by historians to have been a "largely male frontier city" in the mid-1860s, Chicago was, nevertheless, beginning to metamorphose into a major urban center. Its population was rapidly growing and would soon reach a quarter of a million inhabitants, due in large part to both its preeminence as a hub in the network of railroads that would soon crisscross the nation and its leadership in the meatpacking industry. The Union Stock Yard, which opened the year Wing arrived, was one of Chicago's first major industries, providing thousands of jobs to residents and shoving the Windy City into the forefront of the nation's economy.

Despite its rough-and-tumble reputation, Chicago was also becoming well known for its array of entertainment venues. At one extreme it had scores of saloons and bordellos catering to homebred toughs and tourists alike, and Under the Willow, at the northwest corner of Monroe and Wells, was the most famous of all. Behind its walls men could find any sexual experience imaginable, from the everyday to the queer, from the normal to the debauched. It was well known that a few "male prostitutes rented cubicles" there and made themselves available to clients.

At the other extreme were the more legitimate but no less popular forms of entertainment. Uranus H. Crosby's newly erected and elegant opera house opened its debut season with Verdi's Il Trovatore, drawing hundreds to its performances, but Wing, who loved theater almost as much as he loved books and "whole souled boys," was attracted to Col. Wood's Theatre and Museum and its more popular fare, such as John Buckstone's Leap Year; or, The Ladies' Privilege, one of Col. Wood's hits. Wing kept mum in his diary about any saloon or bordello visits he may have made.

During his first few weeks in Chicago, Wing put his nose to the grindstone, often ending the day exhausted by the demands of his seven-days-a-week job of reporting on a variety of Chicago events, from goings-on at the police court to the high jinks at political conventions. To augment his salary, he wrote actual news stories in which he would add favorable mentions of items available in specific stores or services available in specific establishments, neither of which had anything to do with the news stories. He received generous kickbacks from the proprietors for the publicity and admitted to writing many.

Then on Monday, July 3, a month after he first set foot in Chicago, Wing had a brief respite from his humdrum day. He "fell in with a bully little boy" whom he talked up for quite some time in hopes of making a date to meet later. Because he never recorded the boy's age, Wing might appear to have been a pedophile targeting a child, but Wing used boy and boys to refer to anyone to whom he was attracted regardless of the man's actual age — a convention that had been popular among queer men across the United States and in Europe long before Wing arrived in Chicago.

Because no labels had yet been coined for the relationships that grew up between them, queer men created their own from what was at hand. According to historian Jonathan Katz, they might describe their bond as one between a "'youth' and an 'old man,' or a 'boy' and a 'man,'" ignoring the actual ages of the individuals involved, or they might use labels from family life —"child/parent, father/son, brother/brother, uncle/nephew"— as a way to understand that a strong bond existed between men, between men and boys, or between boys and boys. The bond that the labels suggested legitimized their relationship. Walt Whitman used both types of labels in his romantic relationships, calling Harry Stafford, who was twenty-two years old, "my darling boy" and using son when addressing Tom Sawyer, Lewy Brown, and Peter Doyle.

The practice found its way into the popular culture of the time in a camouflaged form. While Wing was out seeking bedmates in Chicago, Horatio Alger, who was a Unitarian minister in Brewster, Massachusetts, was denounced for having sexual liaisons with teenagers in his church, and he quickly relocated to New York. Strapped for cash, he made a successful career and earned a great deal of money from writing his Ragged Dick and Tattered Tom series of novels. In them a wealthy older man takes a destitute teenager under his wing, and through the younger one's hard work and determination — as well as the guidance and patronage of the older man — the younger becomes the epitome of the American success story. The homoeroticism of their relationship lies just under the surface of each of the novels but went virtually unrecognized by non-queer readers. Interestingly while in New York, Alger informally adopted three teenage boys.

Although he was only twenty-one when he reached Chicago, Wing adopted the convention in his diaries, using the generic boy for his pickups and, when he was especially enthralled by someone, the more effusive "bully boy." He once even used boy when he described himself as "a lucky boy." As Paul Gehl has shown, Wing reported in the first volumes of his diaries that he was "the younger partner" in several same-sex sexual relationships during his adolescence and young adulthood, but in Chicago he took on the label of "the elder" partner in his romantic dalliances, even if his paramour was in fact older than he.

Wing never revealed where he met the "boy" on July 3, only that he chatted with him, hoping it would lead to something in the future. It never did. In fact, Wing recorded a number of other dead-end experiences in his diary, as well as several that resulted in one-night stands. On Monday, September 11, 1865, for example, Wing "fell in love with a little beauty," but he "got the mitten," nineteenth-century slang for getting dumped. Upset over the outcome, he had a "d — d poor bed" alone that night. Even when he was able to bed someone, his pickups rarely remained the entire night.

On October 4 Wing made the acquaintance of Johnny Maier. Wing succinctly, and with only a bare hint of emotion, described their first night: "Saw a boy with whom I fell in love, and chased him up. Found him and got him all right. Engaged a room"— that is, he rented a hotel room for the two of them —"and he and I retired. He is a bully fellow, but got up in the night and dug," nineteenth-century slang for slipping out without a word.

Hearing Maier leave, Wing followed him to a pool hall, where Maier began drinking heavily. Instead of returning to the hotel room for which he had paid two dollars for the night, Wing went home, dejected. The next day he wrote in his diary about his "enamorata of last night," and by using the feminine ending a, instead of the masculine o, he may have been hinting about Maier's sexual preferences. Unfortunately, Wing didn't bother to explain in the diary entry why he didn't just take Maier back to his place, rather than the hotel, after they met.

Along with his many one-night stands, Wing sustained a relationship for several days with a young man whom he happened to meet on Wednesday, August 23, 1865. After finishing a reporting job, Wing returned to his office at the newspaper, where, he wrote in his diary, "I run against a boy dressed in military clothes, whose countenance was so familiar that I stepped up to him, and succeeded in making his acquaintance by telling him that I must have met him in the south. Invited him to call at the office in the evening, which he did."

The "boy" was Tommy Phelan, and in his diary entry for the next day, Wing describes his budding interest in Phelan. "When my newly found soldier boy came to the office last evening," Wing reported, "I was charmed by his noble bearing, and the intelligence and refinement which he displayed. Took him to the theatre, and soon became charmed with his society." Phelan captivated Wing with his uniform and his story of having been a prisoner in Andersonville, the Confederate-run prison in Georgia for captured Union soldiers.

They slept together for the first time that Wednesday night and then again the next night. On Friday morning Wing "went to work, somewhat played out by" his sexual "excess" with Phelan, "who persisted in doing" some sexual act that so enthralled Wing that he swore he would "never forget" it. He wondered in an aside if Phelan learned it from his army buddies. It was common knowledge among queer men that some soldiers engaged in sexual relationships with one another and with civilians.

Later that Friday Wing took Phelan to a photographer's studio and had his picture taken as a keepsake. Although their relationship seemed to be going well, Phelan had met a servant girl and asked her out. He told Wing that although he would be seeing the girl that evening, he would spend the night with Wing, not her. But by the next morning, Phelan still hadn't returned.

Wing had a difficult time concentrating at work on Saturday, presumably troubled by his lover's unexpected absence. When Phelan reappeared in the evening, he admitted to Wing that had tried to get the girl in bed but she rejected his advances, and that he decided to spend the night out on his own and not to notify Wing of the change in his plan. Despite the distress that Phelan caused him, Wing welcomed him into his bed that night and reported that he had another enjoyable time. The next morning Phelan rose before Wing and left, vowing to return later that afternoon. When Wing finally roused himself from bed, he discovered that a ring he owned was missing. He didn't want to believe that Phelan had stolen it and rationalized to himself that Phelan had only borrowed it. Four o'clock came and went, then five o'clock, which was quickly followed by six, and Phelan hadn't returned. Wing gave up hoping that he would see him, or the ring, again.

Stealing Wing's ring was not the end of Phelan's surprises. On Monday morning Wing "found to my great horror that my soldier boy had given me crabs, and worse than that, head lice. Found my corpus alive with vermin, and shuddered at the thought. Resorted to ample potations of anquinnin" — probably quinine — "and everything else, not forgetting to use a fine toothed comb. O! Horror!!"

Wing was undoubtedly feeling betrayed and perhaps even a little foolish by now, having been wronged not once but three times by Phelan and in such a short amount of time, and yet he again rationalized Phelan's behavior. By the next day, Wing had forgiven him for the robbery, for the crabs and lice, and for lying about returning at four o'clock. "I love the boy," he wrote in his diary and tried to explain why:

There is an indescribable something about him fascinating in the extreme. The present devotion to myself, professing the most ardent love, and still so refined and the hero of so many battles and prisons. Perhaps he did not take the ring — and he, a homeless wanderer — is not to blame for giving me the horrible vermin! I will trust him, and believe that he did not take the ring.

A few days passed, and Wing still hadn't heard a word from Phelan. Then on Friday evening, September 1, as Wing was busy at work in his office, Phelan unexpectedly appeared at his door, wearing

a horrible old suit of ... citizen's clothes. He says that he has been to Washington and back; that he had no place to stay but at the soldier's rest. The dear fellow! Took him home with me, and love him better than ever. He declairs [sic] that he did not take the ring, and feels terribly that I should accuse him of it. The poor boy is an enigma — I cannot make him out.

If they had sex that night, Wing didn't mention it in his diary, in sharp contrast to his bragging about the sexual escapade he had had with Phelan only a week earlier.

The next day Phelan told Wing that he planned to leave Chicago and head to Milwaukee, and he admitted with a dramatic flair that he didn't have any prospects once he arrived there. He was hinting to Wing that he was available to be kept, if Wing would only say the word, but the fire that he had once ignited in the newspaper man had burned itself out during the time in which Phelan had disappeared. While he was away, Wing was evidently able to put their relationship into some sort of context. Phelan, he seems to have realized, was trouble, and Wing wrote an equally dramatic, and perhaps disingenuous, response in his diary to Phelan's leaving: "O, that I could help him."

Phelan left Chicago as he had planned, and Wing never saw him again. Wing admitted in his diary that he was exhausted from his busy work schedule at the newspaper and from worrying about Phelan's poverty and "strange behavior," but he never explained which of Phelan's behaviors were odd to him. It may have been stealing Wing's ring, or infesting Wing with crabs and lice, or trying to bed the servant girl, or any number of things that Wing had forgotten to mention in his diary.

Robert Williams, editor of Wing's Chicago diaries, has pieced together some of Tommy Phelan's history. Williams reports that if Phelan gave Wing his real name, he may have been Charles T. Phelan, who had enlisted in the Union army on September 26, 1861, when he was eighteen years old. Confederate forces captured him and confined him to the prison at Andersonville. After his last encounter with Wing, he returned to his native New York, not Milwaukee, and enrolled in the Eastman Commercial College in Poughkeepsie. He graduated in December 1865 and the following year sailed to Cuba, where he remained for a year. After he returned to the United States, he married a woman in 1868, and according to the 1870 census, lived in Manhattan.

Wing's summary of his and Phelan's relationship and Williams's investigation into the former soldier's life suggest several important things about Phelan — and about the queer subculture in Chicago in the mid-1860s. Although Wing repeatedly called Phelan a boy in his diary, Phelan was actually a year older than Wing. He may have been a small or otherwise young-looking man and never told Wing his actual age, allowing Wing to think he was younger than he actually was. More likely, Wing used boy as a hierarchical marker, as Whitman and others had done. Wing had money, a place to live, and a station in life. Because he was successful, Wing was a "man," as society at the time defined the term. In contrast, Phelan was destitute, homeless, and without a career or any hope of one for the near future. His only resource was his body. Because he had not yet achieved manhood as illustrated by Wing and been approved by society, Phelan was a "boy."


Excerpted from "The Boys of Fairy Town"
by .
Copyright © 2018 Jim Elledge.
Excerpted by permission of Chicago Review Press Incorporated.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
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Table of Contents

List of Illustrations ix

Acknowledgments xi

Introduction: From Sodomite to Sex Moron xiii

1 Took Him Home with Me, and Love Him Better Than Ever 1

2 The Most Effeminate Type of Sex Perversions 14

3 We Never Liked His Species 27

4 A Fine Piece of Nude 34

5 My Vileness Is Uncontrollable 46

6 The Hottest Show on Earth! 53

7 A Sodomist Is One Who Enlarges the Circles of His Friends 63

8 They're Regular He-Whores 85

9 A Man Will Do When There Is Nothing Else in the World 98

10 Hell, I Wish They'd Give Me a Safety Razor and a Shot of Gin 105

11 Used as a Pimp for Others to Get Their Meat 122

12 All Have Waitresses Who Are Lads in Gal's Clothing 142

13 Play It, Whip It, Pat It, Bang It 159

14 Once a Bitch, Always a Bitch 173

15 A Nudist Club for Boys and Young Men 198

16 Thank God I Got Only 60 Days and a Small Fine 213

Notes 222

Bibliography 244

Index 276

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