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My Prison Pen Pal

My Prison Pen Pal


Why I befriended a convicted sex offender and never regretted my raunchy missives from “Randyland.”

People always ask where I found my prison pen pal, then laugh at the answer: There you can browse gay prisoner profiles, which include stats, photos, location, and the nature of their crime. Most profiles verge on the romantic side, often with unintended irony. "Do you aim to tease or aim to please?" asks a felon incarcerated for sexual assault. "I've made a couple of mistakes in my life, but I have a good heart," ventures Angel, a transgender convict in for double homicide.

Although they may ask where I found him, few have ever asked why. I felt trapped in a dead-end job, surrounded by phonies and sycophants and insidious water cooler conversation ("How was your weekend?" "Great. How was your weekend?"). I was desperate for an outlet, needy to talk about real shit. Not only would a prisoner have real shit to talk about, he promised to be a captive audience.

Randy's personal ad caught my attention because it wasn't advertising romance. Instead, he guaranteed "delish correspondence" from "Randyland."

In his first letter to me, he wrote about his goofy lover: "Butters and I were chillin' one night, watchin' local news when the state prison warden comes on the telly and proclaims to the masses there is no sex happening in the joint on his watch. Cue me: Huh? Cue Butters: Mmgghmm? -- because it's hard to talk with a mouth-load of cock!"

His prose was bursting with sexual innuendo ("My projected release date? Just after lights out!"), clever reminiscence ("That's eight pages, one for every inch of my favorite lover. Sigh, Joey."), and vivid description ("Boiled-beyond-death spinach and a turkey-like compound with gravy? Oh, the humanity!"), and was usually signed off by Miffy Lovelorn Von Tragique. Importantly, Randy also kept it real. "I've been at this pen pal gig for a long time," he wrote. "It's what's kept me sane, relevant, inspired, and determined to survive the mental warfare that is incarceration." That's what kept me writing back.

Randy also made me feel better. "Between the cops and other cons, the never-ending cat-and-mouse game becomes crushingly wearisome. I've seen men crumble in less than a year as the machine devours them." I remarked how Randy kept his spirit unbroken, his humor intact. He categorically refused to be chewed up.

He witnessed some real shit, too, including the time the Nazi with a swastika tattoo on his forehead chopped off a kid's nose with a cribbage board, and the six-man beat down over skimmed hooch that left the skimmer unable to see or speak. But Randy had not suffered for being gay. In his lockup, queers were seen as a novelty. He wrote about the others: Miss Pineapple, a black princess the size of a linebacker; Lorne, the dowager empress who always saw the bright side of life, despite having 37 years of incarceration under his belt; and Dewars, a recovering alcoholic who suffered the shakes. Once, at chowtime, Dewar's hands trembled so much that the rice kept flying off his fork. "Where's the wedding, dear?" quipped Randy.

He also described his lovers, past and present. Butters, 21, loved to be naked. Max, 27, was a firecracker in the sack but otherwise hopeless. Randy wrote, "You name it, I'll nail it--blowjobs, too." His most recent flame was Chas, 25. Chas was well-hung, but his finest attribute was being openly gay, not a quasi-straight ACB ("after count boy"). But no lover compared to Joey, who after his release, sent Randy a Dear John letter that spun him hard. In the span of our two-year correspondence, I never received a letter without some reference to Joey. "Even in here, we live, we luv, we be," Randy wrote.

Randy insisted he would bloom wherever planted and I was inspired by the way he refused to be imprisoned by his circumstances. That's not to say I was sympathetic to his predicament; Randy had been locked up for 10 years in the Texas state penitentiary as a convicted child molester (a "cho" for short, or, as he is gay, a "chomo"). From his profile, I knew he was in for sexual offenses with a minor. From his letters, I learned that when he was 21, Randy had had a sexual relationship with a 12-year-old boy.

Disturbing as this was, I saw no good reason for me to further denounce a man condemned. I wrote asking why he did what he did, how he felt about it, and if he considered himself hopelessly pathological -- the thing about having a pen pal in prison is that you don't have to frame anything sensitively. What are they going to do, feel judged? Letters are opened by officials, so I couldn't send smut or cigarettes, but I could ask things like "What the fuck were you thinking with a 12-year-old?" and "Do you get prison-raped for it?"

He hated the label pedophile ("I don't lust after every boy I see!") as much as sex offender (which implies it's ongoing), but it was therapy he hated most of all. And anyway, he had resolved his own issues. "The focal point of my self-morality now is [to] strive not to hurt others, and, while at it, be sure, at the very least, they're 18." But when he brought up ancient Greece, I wrote it sounded like
he felt he was the victim. Randy insisted he wasn't -- he broke the law and could take his licks.

His crimes, he said, were due to the deceit of being in the closet, mixed with drug and alcohol abuse and anger. "How many chums did I crush hard for in adolescence? Didn't I want some diddlin' back then?" So Randy transposed his 12-year-old self onto an actual 12-year-old boy. At least, that was his explanation.
"I feel remorse that I didn't have a sane enough mind at the time to not introduce the kid into a world beyond his understanding (alcohol, sex). But now here I am, and that soul-crushing guilt I can't afford to harbor."

My colleagues were aghast to learn my prison pen pal was a pedophile. The word is pregnant with the poison of a deed so beyond redemption that it slams every door immediately, forever. But somehow, Randy cracked the door to dialogue. At the water cooler, "How was your weekend?" became "What's new with Randy?" No one felt any better about his crime, but friends would read parts of his letters and wonder with me why Randy will spend the rest of his life on a sex offender registry, but there isn't something analogous for murderers -- a homicide registry?

Illustration by Keith Negley

Randy knew some men are solely attracted to children, but insisted he's not one of them. He believed judges (and the public) don't see individual cases; for them, all sex offenders are bogeymen. Gays, especially, won't go near the topic for fear of association. Demonized as chicken hawk child predators for so long, we run a million miles from anything that gives that old smear an ounce of credence. Randy said he wasn't born with enough middle fingers.

At least he was popular at the post. Randy maintained around 20 pen pals. A few wrote wanting to "cho out" about prepubescent longings, and a few demanded his soul-crushing guilt, but most were just friendly strangers. Randy said he felt fortunate. He kept most of the letters he received and sent them home at regular intervals. After he was released, he planned to take all those letters, ignite them in a big bonfire, and move on.


His oldest correspondent, Bob (a.k.a. Boopsy), was an 88-year-old living in the California desert. Boopsy was not only a loyal correspondent, he deposited money in his prison account so Randy could buy essentials at the commissary (95 cents for a honey pepper turkey stick, $12.75 to splurge on a stylish Casio digital watch) or contraband cigarettes ($6 each).

In prison, Randy worked as a custodian, earning $40 a month until he was laid off due to budget cuts. I tried sending stamps so he wouldn't pay postage, but stamps are verboten, a jailhouse currency used in lieu of cash. So I started sticking stamps on the back of my envelopes he could steam off and reuse. I considered wiring money but wasn't sure if that was his racket, and I didn't want to feel played. But Randy wrote back always without expectation, and I wondered what currency all those pen pals offered him in lieu of cash. A purpose, a distraction, a window, a mirror?

Although he would soon be sprung, the conditions of his release (no drinking, no spontaneous travel, no porn, no contact with friends from prison) took him to a very dark place. "I perceive being freeish," he wrote. "And subject to continual scrutiny, distrust, judgment, and stigmatization." Add to that being an ex-con starting over flat broke and unskilled.

Around the time I quit my dead-end job, Randy finally got a release date confirmed. One day soon, after some 4,300 days jailed, a free-ish life would begin at a halfway house in Austin. After six months "reintegrating" there, Randy planned to go live with his father in Montana. He was imagining future careers (custom epitaphs?), his first meal (a Denver omelet with mushrooms, extra cheese, and a pound of bacon), and little luxuries like owning the marvelous all-in-one Norelco beard-brow-nose-ear hair trimmer. He was also nervous.

The halfway house promised a battery of barbaric tests (such as the penile plethysmograph, electrodes attached to his dick to measure arousal), and he had a more general fear that after so long away, he would be a lost relic from a forgotten age. "Getting out of here will be akin to a second birth," he wrote. "An after-birth birth... a strangely profound yet grotesque analogy."

Then, that day in April, he said farewell forever to Lorne, to Dewars, to all those inside he had come to love, his family for the previous 12 years. After an especially teary, blubbery parting from Chas, Randy hopped a Greyhound bus to Austin. Not having traveled for so long, his first taste of the outside was severe motion sickness exacerbated by nerves and sensory overload.

After spending the majority of his adult life behind bars, Randy found his rebirth unsettling. People were like zombies now, walking around lost in their smart phones. At a Walmart, he found himself standing frozen before a wall of technology, completely overwhelmed and longing for his old Discman. And they say there is no such thing as time travel. He picked up a pack-a-day smoking habit to help cope. "Don't tell my mom -- she'll freak!" he wrote. That must have been a joke.

He said the halfway house was dangerous. More than he ever had in lockup, Randy sweated the sex offender label. He kept the nature of his conviction on the DL and even invented an entrapment alibi in case of violent confrontation. Although he had never felt so menaced, there were bright spots. For the first time in over a decade he was sleeping on a mattress with an actual box spring, and Boopsy had sent him the Norelco trimmer and his very own seven-inch portable RCA TV.

Suddenly, Randy stopped writing. I was disappointed that I didn't even get a Dear John letter when our relationship ended. To be fair, he was just two months shy of being back home in Montana, where I picture all of my letters -- with so many others -- in a bonfire torching that big sky. I'm a part of his past, but for me, Randy is very much present. I've got a new prison pen pal who also understands the value of delish correspondence, and I try to pay it forward where I can.

In his last letter, Randy wrote that another resident at the halfway house had broken into his locker in the middle of the night while he slept and stolen his portable TV. He wanted to retaliate, but he had an actual future to consider now, so instead of avenging the loss he got a bigger lock for his locker and, wouldn't you know it, another TV was already on its way courtesy of good ol' Boopsy.

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