Roleplaying Jail in Iowa With America's Biggest Prison Fan

The night before I was set to turn myself in—either for robbing a pharmacy or committing serial tax fraud, I hadn’t decided yet—I sent Officer Mark Gudmundsen an email with a couple of last-minute questions. “You may bring a book,” he replied, “but I will look at it and decide if you can have it in your cell to read.”

I turned to my usual group chat for confirmation that this was all insane, but found no sympathy. “lol it’s prison man.” “You’re already showing your privilege.” “Why not ask when tea time is?”

“That’s jail,” one friend wrote. ”Literally, that’s jail.”

Typically, you don’t coordinate smoke breaks with your jailer before showing up, or spend $350 a night for an evening behind bars. But Mark is in the business of recreational incarceration, and his prisoners pay good money to sit in silence alone. They travel great distances, some from as far away as South Africa, to piss in rusted buckets behind locked metal doors. Their ranks might be small, but Mark (who is not an actual officer) believes deeply in what he’s selling.

The Franklin County Jail—built in 1880 and shuttered 20 years ago—is in Hampton, Iowa, a deep-red rural town of a little over 4,000 residents. There, Mark lives his longtime dream of running “roleplay adventures” in peace: immersive simulations lasting anywhere from a few hours to a full week, where vetted participants are strip-searched, dressed in inmate-orange, and inducted into jail life as it was lived in the late 1960s.

Nude on my knees the very next day, wiping every trace of wetness from the cell-block shower’s floor, keeping an ear out for Mark’s footsteps and trying to avoid a large insect skittering around my workstation, I began to wonder if I had critically misread Mark’s project. I’d never think to knock a jail-themed bondage business, but I also wouldn’t travel 3,000 miles to spend the night in one.

This binary thinking shames me now, after a day and night in Mark’s custody. The jail isn’t just a historical jail-life reenactment business, and it isn’t just a rural BDSM dungeon. There are shades and degrees to everything, and that is doubly true when dealing with a man as beautifully strange as Mark Gudmundsen.

The jail is on a busy commercial street, between an auto shop and a Methodist church. Approached head-on, it looked like an old, well-tended house, with ornamented railings, tall narrow windows, and a quaintly gabled roof. Only in rounding the corner did I notice the one-story annex jutting straight out its back, its windows squat and eerily barred.

“I’m here to turn myself in,” I said, when Officer Mark Gudmundsen came to the door. “For robbing a pharmacy.”

“Where’s your car?” he asked. The man was slim, and as gangly as a boy who’d grown six inches over summer break. Judging from his glasses, he was nearly blind; I have never seen lenses so thick, or eyes so magnified. A red bump rose from the tip of his widow’s peak—a consequence, I’d later learn, of constant klutzy run-ins with the cell-block doorway.

“I don’t have a car,” I said. “I was driven here.”

Mark frowned. “I thought I’d see you drive up,” he replied. “I wasn’t prepared.” He was, though, in uniform: a beige short-sleeved sheriff’s shirt with a fake badge and specially printed name tag.

“I can turn myself in later,” I offered.

“No, no, that’s fine,” Mark said, leading me into the narrow intake room between his house and his jail. I took a seat in the only available chair, a strap-intensive terror that looked salvaged from a 19th-century asylum, and was handed a clipboard with a contract attached. For the first time in my life I read the fine print, nodding agreeably at certain entries (“There shall be no spitting, playing with urine or feces, blood play…”) and sobbing inwardly at others (“This is a non-smoking facility…”). When I was done, Mark sent me back outside, to the building’s front door.

I knocked. Once again Mark emerged, this time with handcuffs.

“I’m here to turn myself in,” I said. “Robbed a pharmacy.”

“Well, at least you’ve confessed. That’s a mark in your favor,” he said.

Then he told me to get up against the wall.

Minutes later, in the intake room, Mark ordered me to strip: first my shoes, then my socks, then my shirt and pants. I was allowed to slip off my boxers behind a waist-high partition, though not before lightly spreading my buttcheeks to Mark’s satisfaction—legally, the closest we could come to a historically accurate rectum check.

The experiment started two summers ago, in 1966, and like Mad Men has been steadily advancing through the decade with each season. (The jail is only open in the summertime, as it’s too expensive to heat the rest of the year; so far Mark has hosted roughly 20 prisoners per season.)

“You’re not one of those hippies, are you, son?” Mark had asked, after inquiring after my draft card, and whether I’d ever taken “LDS.” Mark says he models his character on the guys he grew up watching on TV, like Archie Bunker. In reality he comports himself like a late-aughts Michael Cera character: constantly mumbling, or trailing off, or making little self-deprecating asides to no one in particular.

Why 1967? Had he set it any earlier, he would have had to track down a bunch of old-timey prison costumes. (The late ’60s were apparently when the prison industrial complex first developed its taste for orange.) Without quite realizing it, though, Mark has landed on a moment of real significance, to which the origins of both mass incarceration and his own jail can be plausibly traced.

The great legislative victories of the Civil Rights movement were just a few fraught years in the rearview; black activists, freed at least in theory from fighting the most blatant strains of injustice, were turning their attention to the root economic causes of inequality. There were 300,000 people then in jail, and though a disproportionate number of them were black, it was nonetheless a hopeful moment; as Michelle Alexander writes in her book, The New Jim Crow, criminologists of the period “were predicting that the prison system would soon fade away.”

Things didn’t quite play out like that. Instead, propagandistic buzzwords were used to justify a decades-long program of mass incarceration which intentionally and disproportionately affected black communities, such that today black prisoners make up 43 percent of the population at facilities like the one Mark’s used to be. Often they’re trapped there for lack of bail money.

Whether this pre-emptively damns Mark’s endeavor, or makes something grotesque of play-acting the life of an inmate, is for each to judge on their own—though it is worth noting that Mark is currently raising money for the Innocence Project. For every 20 cents donated over at JailMan.com, he’ll spend a minute in jail, and donate half the proceeds.

The sheer level of detail suggests an interest closer in spirit to civil war re-enactment than anything overtly sexual.

As for why anyone would develop an interest in recreational incarceration: Jail films have been a staple of Hollywood since the silent era, but jail entertainment took on a new cast with the advent of cable. Lurid docu-dramas proliferated on channels like MSNBC (whose Lockup ended its 12-season run earlier his year), claiming to give curious viewers an “authentic” glimpse of what went on in the vast gated compounds now visible from millions of commutes.

This profusion of facts and anecdotes concerning “life on the inside”—fed as well by shows like Orange is the New Black and all the crushing journalism on the subject—has produced a society in which prison exists for one segment of the population as recreation and for another as a life-destroying force. That some small, unusually motivated segment of the former group should have their curiosity stoked to the point where they’d actively choose to stay with Mark is a sensible, if perverse, byproduct.

Mark openly copped to this connection when I asked him why he’d moved thousands of miles from his home to operate a pretend jail in the middle of nowhere: He says his interest in jail life stems primarily from the Westerns and prison flicks he watched as a kid.

And the one former guest Mark agreed to put me in touch with, who told his family in Wisconsin he was visiting a “friend” before driving over to Mark’s this past summer, seemed similarly motivated. “If a person has never been stopped by the police for any reason,” he said, “it’s kind of a different experience. People have some curiosity about that, I think.”

Still, no pat sociocultural analysis could ever hope to pin down the whole of Mark’s clientele. None of the above explains the man who rented a cell in order to better understand his life-sentenced half-brother, nor the multiple ex-cops who’ve come to Franklin to “play the other side” (in Mark’s words). And nothing can explain the wannabe guest—one of the few Mark has flat-out rejected—who asked to be jailed for the rest of his life.

Out in the yard for my first post-intake cigarette with Mark, I was waylaid by another jolt of unreality. A number of young families were filing into the church across the street. I kept expecting them to gawk or form a spontaneous picket line, but these Iowans were skilled as subway riders at ignoring strange behavior. Which was wild, because I couldn’t stop looking at us: a 60-something man and his much younger buddy, both in costume, chatting on opposite sides of a barbed-wire fence.

It turns out Mark is a member of that church; those people I saw were headed to community dinner night, he said. It was to that church’s minister Mark turned when California came to ruin him, a little more than two years ago.

This is not Mark’s first DIY jail. His first was run out of his home, in Apple Valley, California. It wasn’t long before reports emerged, in the local paper, of “incarcerated prisoners in orange jumpsuits [who] appeared to be working on a project in a residential area.” Locals weren’t much soothed by the discovery of meninchains.com, Mark’s subscription bondage website. The town brought a civil lawsuit against Mark, which claimed he was running a “bondage fantasy” business without a license.

The suit was eventually dismissed, at a cost of $82,000 to the town, but by then Mark had already found the Franklin County Jail. Before buying it, he’d secured a written promise from Hampton officials that he’d be able to use it for his “jail roleplay adventures,” but the whole thing nearly fell apart when, in early 2015, officials of Apple Valley—not content with merely running Mark from his home—rung up their counterparts in Hampton and claimed Mark intended to run (as Mark put it) “some kind of gay sexual thing” right there in the center of town.

The injustice of this still clearly pains him. “I went over to the minister,” he said. “I was crying—I didn’t know what to do. I was ready to throw in the towel. And the minister said to me, ‘Mark, prove them wrong.’”

The hope is that someone might, in the monotony of Mark’s pretend-jail, find whatever it is they’ve been hiding from themselves.

I’ll admit that, no matter your commitment to broad-mindedness and the eradication of sexual shame, it is very hard, after browsing through meninchains.com, and maybe laying out $11.95 for a month’s access to (for instance) “Ten Stress Positions in an Iron Strap Cage,” not to see some connection between Mark’s two businesses. Or, for that matter, between those professedly non-sexual businesses and his private life—about which he’s very open—as an active member of the BDSM community.

To Mark and his lawyers, this line of thinking is homophobic. And after 24 hours as Mark’s prisoner, and many more hours of emotional post-jail conversation, I am ready to, if not agree with them, at least suggest that there is a real distinction to be made here. The man likes erotic bondage-play, and he also chains people up for educational purposes. Mark has quizzed a number of real COs on cuff procedure and dressing order, and has read widely on the exact kinds of restraining implements used by 1960s jails; the sheer level of detail suggests an interest closer in spirit to civil war re-enactment or model-train building than anything overtly sexual.

The two of us stood in contemplative silence in the yard; I’d long since stubbed my cig in the grass. Behind Mark, on the sidewalk, a small boy biked by, the first pedestrian to openly stare at us.

“Well,” Mark said, oblivious to the boy. “We better get you inside.”

“Yes sir,” I replied.

Inside, Mark locked me in my cell and shut off the lights. “This isn’t part of the roleplay,” he said, “but I want you to hear it.”

Mark moved out of my line of sight. Moments later, unseen speakers filled the cellblock with music. The mix Mark played me that afternoon—a medley of American popular music, from the inception of recorded sound to the Summer of Love, arranged chronologically and accompanied by rehearsed spinning-newspaper commentary from Mark (“Hitler was rising to power: There was going to be a war again”)—lasted 80 minutes.

Mark paced up and down the cellblock, summoning ghosts. “Close your eyes. Imagine the inmates in here, missing their wives and families,” he said. “Everyone who ever lived here is dead.” Barbershop bled into ragtime; the lights switched on, to signal the advent of electricity at the Franklin Jail. “My mother was engaged to a soldier in Germany,” Mark said, approaching the ‘40s. The soldier died, but the war was won, and Mark’s mom met Mark’s dad.

Here we might cut to Mark’s own Orange is the New Black-style flashback. Mark’s was a typical Boomer childhood—riven by sexual guilt and consumed by the impending threat of nuclear annihilation. This was Orange County in the ‘60s, John Birch country, where a funny mustache could get you labeled a communist. And Mark’s people were Mormon, too, from way back; if the Russians didn’t get him, he knew, the rapture would, especially given what he was up to in his bedroom.

It wasn’t until he was close to 50, after a marriage and a number of careers—as a house-flipper, escape artist, esteemed regional landscape painter—that Mark realized with the help of a Mormon psychologist that he was gay. This news nearly led him to suicide. But at the suggestion of his therapist, and with the warm encouragement of his friends and family, Mark entered gay conversion therapy, where he was told to try basketball.

Seven years were spent waking up late, watching Wheel of Fortune, and going back to bed. Sometimes he’d switch things up with a stint in the psych ward, where he’d flail and yell until they strapped him down, at which point a familiar peace would descend upon him. His psych ward doctor, a lapsed Mormon, caught on to his act: You’re coming here for your bondage, the doctor said.

The ex-Mormon took an interest in Mark. It wasn’t long after that Mark ditched the pills and started gradually to come out. He spent a week in the garage of a couple he met online, locked in a U.S. Marshall’s holding cell. Three days in he started laughing and couldn’t stop. His jailers figured he’d lost it but Mark insisted he was fine, better than fine. Others might travel to find themselves; Mark reduced his world to the size of a cell, and there, finally, was freed.

Mark says the jail’s his way of “paying it forward.” The hope is that someone like the person Mark used to be might, in the monotony of Mark’s pretend-jail, find whatever it is they’ve been hiding from themselves, just like Mark did in that alarmed couple’s garage.

It’s possible that Mark has gravely misjudged the potential audience for this undertaking. Miserable, repressed people are America’s largest marketing demographic, but it is a highly specialized subset of this group that stands to benefit from Mark’s experimental school of historical therapy, if they seek it out in the first place.

But he doesn’t seem to care. He is barely breaking even, he’s spending weeks at a time cuffing and uncuffing prisoners, and feeding them, and (at night) vigilantly tracking them for sounds of distress with a baby monitor. But he is having fun, for possibly the first time in his life. Mature fun—defined, let’s say, as the activity that best aligns with your ideal sense of self.

I lacked a frame of reference for what I felt, as this costumed hobbyist frisked me in front of traffic at three in the afternoon. Mark complained at one point that I looked too happy to be in jail, but it wasn’t exactly happiness I felt, as he led me from the fence to the front of his house. It was more like awe, or the surprisingly pleasant aftereffects of a non-fatal brain virus: just this dizzy, delirious wonder.

As part of the intake process, Mark had delivered a docent-ish lecture on the jail’s first prisoner. I couldn’t take notes, because I was handcuffed, so the story is mostly lost to me now—but it did definitely involve a man murdering his wife and then taking back a brooch he’d bought her. Mark had pulled the brooch with great ceremony from his pocket and pressed it into my cuffed right palm. He told me I was touching history’s DNA.

As for Mark’s non-journalist clientele: he estimates maybe 40 percent come because they’re into bondage. But he doesn’t pry, and besides, there are dedicated businesses for that kind of thing. You don’t drive out to a place like Mark’s—located in what my Uber driver, proud resident of what he called “the middle of nowhere,” described as “the actual middle of fucking nowhere”—unless you’re genuinely interested in what Mark is chastely offering.

Dinner was served on a sectioned cafeteria tray. Spaghetti with homemade meat sauce, salad with slices of tomato from the garden, a slab of garlic bread and, for dessert, chocolate pudding. This was a tribute to the old sheriff’s wife: One ex-inmate still living in Hampton told Mark she’d made the best food he’d ever had, in or out of jail.

When I was done, Mark collected my tray and wheeled in a flat-screen TV (“Just pretend they had these back then”) for a first-night Hampton tradition: A screening of the film I Am a Fugitive from a Chain Gang, from 1932. The movie was pre-Code, gritty as pay cable, and its white protagonists were brutalized enough that the movie sparked, in its day, a national conversation on incarceration. Watching that make-believe version of prison-life inside of a make-believe jail modeled primarily on other make-believe depictions of life on the inside, the contours of the pop-cultural feedback loop I was trapped in became clearer. It’s carceral kitsch.

Mark burst into the jail at the exact moment the film ended; I suppose he’d been listening on his baby monitor. It was late, long past usual lights-out, and Mark was anxious to talk to his brother, just then weathering the California wildfires. But he was kind enough to take me out for one last cigarette. We’d lapsed, at this point, into our normal selves. Except for the outfits, and the fact that I couldn’t leave my cell without Mark first unlatching my cell door and then cuffing me and leading me out into the yard, we were just two guys having a conversation, on either side of a barbed-wire fence.

I’m going to tell you a story that Mark told me, out there, the two of us lit by bulbs unreplaced—or so Mark dubiously claimed—since the late 1980s, the last time the jail was really a jail. In those days, he said, a man had done the near-impossible: He had busted out of Franklin. The cops found him pinned in Mississippi by some would-be Samaritan and dragged him right back to Iowa. This man, by the way, was black. Mark mentioned this fact without apparent prejudice, but still: He mentioned it, right upfront, the first time race had come up in our time together.

The man was stripped of yard privileges, begged to be let back outside, and was eventually offered a bargain by his guards. Mark heard all this from an old lady in town, one who still clearly recalled the spectacle: a black man out in the yard, taking in the air, the only prisoner out there with a leg locked to a short length of chain. It’s said the man, when freed, tried to sue but didn’t get very far: He had apparently signed a contract saying he was okay with it. It had been, said the guards, his choice.