IT HAPPENED TO ME: I Role Play Sex Online in the Dirty Pen Pals Subreddit

One of the fastest growing and most heavily trafficked adult sections of Reddit, is an interpersonal writing with a focus on detailed prompts.
Publish date:
June 16, 2015
porn, reddit, sexual fantasies

It’s 2 in the morning, I just had an orgasm, logged out of a chat window, and I’m going to sleep.

“Charles” and I built a long, long story about a good girl who wants to tell her darkest secrets. He was a good listener. I hope I was, too.

He gets placed in my mental Rolodex with as much detail as I could gather: 44, unmarried male from the west coast, gentle caring Dominant who likes to care for and encourage young women. Enjoys issuing challenges to me and offers some dirty, dirty requests. No images were requested.

One of the fastest growing and most heavily trafficked adult sections of Reddit, is an interpersonal writing with a focus on detailed prompts. These "prompts" read like a cross between a personal and an erotic book teaser.

Around the holidays, I was restless and was considering a resurrection of my long-shuttered sex blog. The blog I was writing during my wild and crazy 20s led me right to a really prolific online community of sex-positive writers, which was great. I also found myself fucking a reader and sexually acting out. Not so great.

A lot of those writers have moved on, shut their doors or disappeared. I was reminded that it is always best to keep moving forward in life and online.

A friend sent me a link to an “ask me anything,” or AMA, completed by a self-proclaimed “nerd loving” sex worker. She was funny, compelling and straightforward.

I immediately fell down the Reddit rabbit hole just like Alice in Wonderland. Reddit is designed in evolving layers, and it is so easy to get lost in threads upon threads, dig into non-mainstream media, online debate, explore community discussions on thousands of topics, and read personal disclosures by the bucketful. It's really a very dense, very addictive space.

Some areas of Reddit can also be disturbing, and just like with any other medium, you need to keep a close eye on what you are choosing to access. Many a kitten video has been watched to try to shake off a creepy raw feeling after seeing something unsettling.

It wasn't very long before I found Dirty Pen Pals, populated by all types of people with all kinds of sexual kinks and desires just waiting to be rolled out for me. There are boundaries and rules set by the capable moderators. Check them out here.

I enjoy digging around in people's desires and affirming them, and so for me, DPP became an addictive outlet. It is anonymous, there is an element of managed risk, and it feels liberating to explore hidden sides of myself with another human in a seemingly compartmentalized setting.

It’s also real-time porn, crafted by you in partnership with a stranger. It is part seduction, identification of needs, exploration of wants, and determination of limits.

The world you build is yours, and the level of detail and type of engagement also is determined before things get intimate. I appreciate that you are forced to be intentional and vulnerable when you ask for what you want.

Want to fuck a version of your cousin? Post it. Curious about futanari, body modification, feeding, voyeurism, age play, illicit encounters with a celebrity? Post it. One of the most surprising elements of this is the lack of shame. What you want, you can create.

It should be noted: I'm not a gamer. I don't "gamify" my life, don't role-play online in World of Warcraft or Dragon Quest, etc. I'm a very extroverted, very sexual former party girl who enjoys taking calculated risks and conquering fears. I also enjoy disclosures from strangers, jumping inside another person’s mind and I appreciate a well-kept secret. There are LOTS of great secrets on DPP.

I try to be bravely authentic with who is in the white chat box with me. I still struggle to determine how much to present. I always have to ask myself if I’m going to share my real name, share my city, my general career, what I had for dinner. Sometimes I share two truths and a lie, feeling like the calculated risk of disclosing small details is worth the connection I want.

I’ve told strangers the deepest truths about myself in that space. I’ve read things that cause me to marvel at the ability of a perfect stranger to peer inside my psyche and pluck the most basic truth about who I am. Really and truly, it has offered me breathtaking moments of honesty.

This community has offered what Esther Perel suggests as the underpinnings of captivation; adventure, novelty, mystery, the unknown and a sense of surprise.

I’ve chosen to accept some version of the person truths of my writing partners. One of the unwritten rules of improv is “never negate” – always say yes, accept as truth, lean into a story. That’s a best practice in the DPP world too; set limits before things get heated, and hold yourself and the other player accountable to the limits you set, but never negate. To really encourage, lean in to sameness, edge, risk and bold truth.

Many of the people I co-write/co-create with have reminded me that we’re all sexual creatures, and sexuality dialogues and exploration is maligned and shamed into whispered, secretive conversations where even your first name makes you feel exposed.

And like everything, DPP is never just about one thing. For some it is about escape or self-soothing. One partner was struggling with the miscarriage of his second child. Two or three of my partners are virgins, exploring a real dialogue with me where, in the past, porn has been their only access to what might make a partner happy.

A few female partners are curious about sex with women, how friendship might evolve into something else. They want to talk about what boobs feel like, how their pleasure connects to another human being.

Sometimes the exchanges are raw. Sometimes I feel like I’ve projected an entire life onto another person -- “John” is the basketball player that I used to see at 3 AM in college, “Chris” is the darling virgin who is polite and curious, “Emma” the shy girlfriend, “Rob” the confident dominant. “Ben” -- literally so desperate to feel anything pleasurable he would reach out 2,3, 4 times a day. (I gently suggested he take a break and talk to a professional -- DPP burnout is a very real thing. I hope he finds the help he needs.) “Justin” used to write me the most amazing letters, disclosing such personal heartbreak I couldn’t help but share my own.

I know that these partners could be anyone. They could be another gender than what they present, in another country. They might be lonely. The only thing I’m certain of is their vulnerability -- I’ve accessed a tiny but really valuable compartment in their lives. I won’t be flip about that.

There is a place for this kind of connection. It’s mentally and emotionally a rich place for me, demanding, and yet a space where I feel I’ve grown. I’ve learned that people are yearning for a place to say difficult and complicated things, want to test who they think they are, are seeking to take leaps and be caught by someone caring and capable. Smart people make the best partners, and the freaks and geeks that populate Reddit are my people. This tribe is sexy.

Many partners disappear without warning. It’s an interesting rejection to find that your co-writer has unexpectedly deleted their account. I’ve been very lucky – I’ve only experienced that a few times, both with women who were tipping their toes into conversations about sex with a faceless stranger. Sometimes, you just need to cut ties and go. I understand that – boundaries are critical to this type of connection.

It is incredibly challenging to write long-form stories that engage the other reader, and to be honest, I don’t consider myself to be at the top of the DPP heap in terms of writing.

Within DPP, there have been prompts and stories that have evolved over months and months, filled Google docs with collaboration and creative hot, sticky, yummy sex – people have met partners/lovers via this medium. People have fucked for real. *Not that is an expectation, a goal or endgame here. It is the exception.

Consider the variety of approaches to another person that might be present in a room of 100 people. Now consider approaching a stranger based on their somewhat self-aware and candid prompt inviting you into the world they would like to create, the experience they want to explore.

I had a boyfriend who loved RPG and would disappear for hours to go on “raids” – immersive experiences with multi-player strategy and execution. Now, imagine that raid is just two people. And you aren’t shooting at dwarfs. (Well, maybe you are, but you are shooting naked and your ammunition ain’t bullets.) Trust me when I tell you, I now get the appeal of MPG/RPG on a whole new level.

It is called "playing" online, much like role players and some sex workers create a scene and engage in the scene development, you have to co-create with your "partner" in real time.

This type of sexual play (erotic experience without real-life sex) isn't going away, and it is changing sex and exploration for a lot of people. Much like phone sex lines and other forms of anonymous sexual play, the boundaries for disclosure and the limits of this space are very fluid -- I'm still learning how to keep my boundaries fixed, how to craft language that gets a partner off, how to create trust and encourage honesty, and how to move people to be intimate and vulnerable with me.

I'm also becoming a master at masturbating while I type and pace an experience. That's tougher than it sounds.

I've had a lot of really powerful, positive experiences. I care about this community. I want it to get better, continue to develop a set of flexible norms that meets the needs of the players.

I want players to feel safe in the space, want to embrace members of as many sexual communities as we can. I want sex to be explored without shame and want high quality, organic methods to explore desire.

I’m in control of who accesses me, and how I affirm and encourage the pleasure of other people. I’ve been lucky and my risks have been rewarded.