Prison Penpals

Prison Penpals: How to Write a Prisoner and What to Look out For? By Robert Rosso

Over the past 10 years the number of women seeking relationships with men in prison has increased ten-fold. Prior to 2006, many guys in prison, who were genuinely looking for female companionship, were reluctant to send money to prison pen pal websites because it was primarily homosexuals who were responding to their ads, even if they specifically requested correspondence with “Females only.”

Case in point. In 2002, while serving time inside of Leavenworth, my friend James White placed an add on prisonpenpals.com seeking female companionship. A good-looking guy, he’d long dreamed of finding a hot chick to bone down as soon as he got released. But that wasn’t to be. Instead, he got scores of mail from men wanting to be his sugar daddy.

One man was a 65-year old retired businessman from New York. In his letter he wrote: “I’m looking for someone to love. Someone who I can walk into the finest restaurant in town with, hand-in-hand, and be the envy of the place…I’m looking for someone like you.”

Another guy, a 54-year-old college professor described himself as a “happily divorced bisexual man who likes to fool around.” He offered to send White books and money. “Need some porn?” asked the freaky-professor. “I’ll be more than happy to send you some.”

After reading this letter, I turned to White and begged him to write these guys back. “You gotta do it, bro,” I said. “These guys are both begging to send you money.”

I should point out that inside the belly of the beast it’s widely known among the inmate population that gay guys commonly send their pen pals money. This has created quite a scheme, where straight guys pretend to be gay and do things like write homoerotic smut letters or engage in phone-sex all in the name of cash. But James, a major homophobe, wouldn’t do it. So I did.

Pretending to be White, I wrote each of them a letter portraying myself as a scarred, timid, young man trapped inside a violent prison. You see, although James was a 27-year-old convict with with a shaved head, goatee and tattoo’s covering his body, the picture he had posted on prisonpenpals.com was taken when he was a freshman in college, back when he looked like a cute young boy. And don’t you know, both of them took the bait.

The retired businessman, Joe Barboza, replied back with a marriage proposal. “If you agree to be my wife,” he wrote, “I will send you $300 a month and whatever else you need. I will also include you in my will and make sure that you’re well taken care of long after I am gone.”

But Joe’s proposal came with preconditions: “You must allow me to contact your mother and tell her that we are in love, and that once you are released from prison you are coming home to me.

And never, never ever pull away from me when I hold you at night,” Joe warned. “Or else.”

As for the horny professor, whose name was Dr. Larry Sully, he wrote back very aroused and offered White some books. “Hey, has anybody ever tried to rape you in there?” he asked. “Care to share the details?”

If only the women who write to men in prison could be so direct. Which brings me back to my point.

Now that so many women are doing the prison pen pal-thing, one of the most common things they say when they reach out to prisoners is that they saw their profile on such-and-such website, found him interesting, and they were writing to see if they can “help” him.

A few years ago, a friend of mine showed me such a letter and asked what the girl meant by wanting to “help ” him.  “What should I say to her?” he asked me. I told him to tell the bitch to strap a bomb on her back, run head first into the prison gate and shout “Allahu Akbar!”- the hole she leaves behind will not only “help” him escape, but many others as well.

While I know for certain there are many women out there who do have good intentions and sincerely want to “help” inmates, I think 9 times out of 10 there’s usually a lot more to it. I mean, we are all adults here; lets not kid ourselves. The truth is women tend to be attracted to “Bad Boys”, and I personally believe that most women who do seek correspondence with prisoners are looking for bad boys that they can mold into a softer, kindler, gentler version of their pre-incarceration selves, yet not so much as to lose their bad boy appeal. Others just want someone bad and dangerous and they don’t give a damn if he’s changed or not.

Besides searching for that perfect bad boy, some of the other reasons women commonly write to prisoners are: because they are infatuated with the prison culture; they suffer from low self-esteem; they’ve been mentally, physically or emotionally abused (or sometimes all three); they are seeking attention; or they are involved in a relationship where their physical needs are being met, but not their emotional ones. Whatever the case, time and time again, many women contact prisoners under false pretenses.

What most guys in prison long for is a girl who is honest. The vast majority of us in here have been royally fucked over by women either prior to or post-incarceration, and being up front and honest is priceless. For example, if you are one of these girls reaching out to inmates, instead of using the old “I want to help you” line, just say, “Hey, I ran across your profile and I think your hot. Let’s fuck when you get out.”

Or, “I weigh 450 pounds and I haven’t seen my feet since the 90’s, and as I was sitting here in front of my computer stuffing my face with pizza and ice cream, I came across your profile and I was wondering if you’d mind writing me. Big girls need love too, you know.” Or “I’m beautiful and a real good person – when all of my medications are working properly.” Or, “Hey spunk, I’m down for committing crimes, sending you naked photos, or having you use and abuse me anyway you want. You wanna nut in my butt and make me your slut?”

Okay, I realize those example may have been a little extreme, but my point is honesty is needed. Not only will it help the guys in here figure what your intentions are (and perhaps not waste each other’s time), but it may help the person on the outside separate the guys in here who do have good intentions, from the ones who have bad intentions.

Which brings me to this.

A friend of mine sent me an article written by a former correctional officer. In it, the ex-prison guard talks about an inmate who ran an elaborate pen pal scheme. In a nut shell, the convict would purchase a mailing list of women from a magazine that caters to inmates, send everyone on the list the same introduction letter, then once the women would respond he’d feed them lies about how he changed, how he desires a better life and so forth, with the ultimate goal of having women send him money or landing a rich broad.

When I read this, I thought about all the pen pal schemes that I’ve ran across through the years, and some that I was even involved in. At the same time, I couldn’t help but wonder, “aren’t there a bunch of people in the online dating world out there pulling the same kind of scams?” I mean, money aside, I can tell you story after story about guys in here getting “cat fished” by fat chicks.

My point is people get burned everywhere, everyday. Prisoners do use and get used, but that doesn’t mean people should be totally put off writing to people in prison just because these illicit schemes exist. When writing prisoners you should be honest, but cautious. If someone asks for money right away, run. If someone starts with the “I love you” real quick, run. If someone corresponds with you for a month and asks you to marry them, uh, run. But then again, if they do that to you out there, shouldn’t you run as well?

If you like this check out Prison Gang Management .