Bawdy Storytelling – Episode 29: Sex and Tech
Host: Dixie De La Tour
Date: June 28, 2017
Theme: Exploring the collision of sexuality and technology through true, personal storytelling. Three storytellers share hilarious, poignant, and boundary-pushing tales about finding empowerment, connection, and kink in the digital age.
Overview
This episode delves into how technology intersects with sexual identity, desire, and kink. True stories range from bold explorations of power dynamics in digital relationships, through techno-mishaps in pursuit of intimacy, to the emergence of high-tech domination as a lucrative kink. Through candid, witty storytelling, the guests expose the vulnerability, comedy, and ingenuity found when sex and tech mix.
Segment 1: Cherry Zonkowski – “Sissy Bitch and Captain Underpants”
[03:31–16:28]
Key Themes
- Healing sexual trauma and reclaiming desire
- Navigating online dating and power dynamics
- Exploring dominance, submission, and digital kink
- The messy, life-affirming search for empowerment
Story Summary
Cherry begins with a stark, vulnerable account of her history with trauma—"My father was an abusive alcoholic... I've been sexually assaulted three times in my life" (03:39)—contrasting this with her craving for “white hot passion.” She seeks to break toxic relationship cycles through celibacy and self-investigation, but finds it's not enough—she still craves being "the intense focus of someone's desire."
Cherry turns to online dating, drawing lines between “douchebag doms” and the rare, genuine submissive. After an exchange on OkCupid, she meets a Navy officer who is deeply—and digitally—submissive:
- "I’d like to put you in a collar and a leash, train you... spank you... strap it on and fuck you in the ass."
- His digital reply: "M this big long string of M’s on the screen." (06:59)
The relationship swiftly becomes a sexting power fantasy, with Cherry reveling in her newfound agency:
- “That got me instantly hard. I get hard just from a message from you. That is power. And it felt like power.” (07:58)
- She discovers his desire for feminization—“You want to be my little sissy bitch, don’t you?” (“Mmm. Yes, please make me pretty.") (08:35)
Logistical and ethical complications arise: he has a vanilla, monogamous girlfriend. Their only encounter remains on Skype, with Cherry orchestrating a hybrid between performance and control: "I hold him like that and I put on my makeup really slowly. This is very hot for him." (09:12)
When he won’t meet, she walks away.
Cherry then contrasts this with a real-life, chaotic affair with “Captain Underpants”—ultimately recognizing, with hard-earned wisdom, that both connection and transformation mean facing her own needs and limits.
Memorable Moment:
"When I handed him his underpants, he looked at them and he looked at me and he put his underpants on his head. And I said, yeah, that's about right. And I knew I was making the right choice." (11:44)
As she copes with heartbreak, her “sissy bitch” resurfaces—this time single, desperate to serve, but she initially declines. Later, at her lowest, she relents and texts “Hello, sailor.” His reply:
"Every single goddamn day, I jerk off thinking about you." (13:53)
Their digital kink escalates (“cock cages and incest fantasies and cuckolding fantasies”), but she never meets him before he moves away. She’s left with two 'wins':
- "I had this intensely passionate experience... but I'm not devastated. And that's huge for someone like me." (15:42)
- "For the rest of my life, I will get to say, hey, you know what? I used to make a US Naval officer my little sissy bitch." (16:25)
Segment 2: Gary Pinsky – “Big Daddy Longstroke”
[17:27–28:17]
Key Themes
- Late-blooming sexuality and self-discovery
- Tech-enabled sexual encounters (and mishaps)
- The gap between fantasy and reality
Story Summary
Gary, a self-described late-bloomer, tells of his attempt to use newfound access to wealth and technology for sexual adventure. Formerly working for the government, he takes on a gig as a personal assistant to a testosterone-fueled billionaire, house-sitting a luxury mansion while the boss is abroad.
Prompted to use Tinder, his profile is him in the mansion's hot tub. He matches with a woman who looks like Zoe Saldana, but she’s about to leave town. Undeterred, she requests his Skype. Gary decides to impress her with a name: "Big Daddy Longstroke, all caps" (22:08)
Expecting sexts, he instead gets a PDF script for a roleplay:
"I misread it. It's called the Whore's Whisperer, and it's a script that she's written so we can have long distance, Skype, roleplay, sex." (22:54)
Armed with technical prowess (and the help of the household IT guy), he stages an elaborate Skype session. But the combination of nerves, alcohol, and technical complexity derails the encounter.
Memorable Moment:
"Baby, baby, you know... Who's your daddy? Who's your daddy? Call me Daddy, baby. Call me daddy, baby. Yeah, Daddy baby to voice command was my boss’s wife." (25:27)
This inadvertent voice command attempts to conference in his boss's wife—mid-sex roleplay—at a time when the boss's extended family is gathered in Israel.
Gary freezes, but the call disconnects miraculously.
Quote:
"I just collapsed into a naked heap in the middle of the room. Zoe called back. I did not answer. I deleted Tinder." (27:20)
He concludes that he won’t pretend to be someone he isn’t, and sex or no, authenticity matters most.
Segment 3: Mistress Harley – “The Tech Dom”
[30:31–39:30]
Key Themes
- Financial domination as high-tech kink
- The power and ethics of digital control
- The business of erotic tech subculture
Story Summary
Mistress Harley, donning her signature pink velour, brings the audience into the world of “data domination.” She describes remotely tormenting a slave in Norway, using his house’s nest cams to play ghost noises, then blaring the 1812 Overture in the dead of night:
Quote:
"He jumps up. He’s, like, looking around. He realizes only Mistress Harley can be doing this to me right now. And so he gets on his knees and he starts bowing up and down, looking at the cameras like, I’m. So. Whatever I did, I’m sorry. And I’m just laughing my ass off. I’m like, you can go to bed now. This was just for my amusement." (30:56)
Once a game industry QA tester, Harley discovered financial domination—a kink where (mostly) men pay to be dominated financially or digitally:
- “My first response was, no fucking way. That’s not real. I’m Jewish. I would know about that shit. But upon a Google, I discovered this entire community...” (32:32)
Her skills let her remotely take control of submissives’ devices, install monitoring and ransomware, delete files, and “rent” access to their lives:
- "Half these guys got to pay me every week just to use their own computer. Like, it’s a pretty sweet deal, you guys." (33:59)
- "I can respond to text messages as if I’m using your phone. So, like, I can really fuck with people. Like, if somebody doesn’t pay me the money I want, I can start sending weird texts to their friends or their boss or their wife..." (34:37)
She describes taking on a “loser” named Michael, who is put on her “hall of shame” website and ends up in a legally binding $15,000 debt contract at 23% interest, paying $800/month for financial submission.
Memorable Quote:
"There are just like, hundreds of these guys just so desperate to give women their money because... it’s satisfying for them to feel like they’re serving a superior and beautiful woman. And ultimately, like, you’ve all experienced this in your vanilla relationships..." (36:54)
She closes by challenging the audience’s assumptions:
- "Before you start to judge... consider what I might find if I was inside your computer looking at all of your website histories and passwords and emails...” (38:46)
Notable Quotes & Moments
| Timestamp | Speaker | Quote / Moment | |:--------------|:------------|:------------------------------------------------------------------------| | 03:39 | Cherry | "My father was an abusive alcoholic... taught me that if I stood up for myself, I was going to get cigarette smoke in the face or a beer on the head." | | 07:58 | Cherry | "That got me instantly hard. I get hard just from a message from you. That is power. And it felt like power." | | 11:44 | Cherry | "He put his underpants on his head. And I said, yeah, that's about right. And I knew I was making the right choice." | | 13:53 | Cherry | "'Every single goddamn day, I jerk off thinking about you.' Yeah, and I really needed to hear that right then." | | 16:25 | Cherry | "For the rest of my life, I will get to say, hey, you know what? I used to make a US Naval officer my little sissy bitch."| | 22:08 | Gary | "My Skype name is Big Daddy Longstroke, all caps." | | 22:54 | Gary | "I misread it. It's called the Whore's Whisperer, and it's a script that she's written so we can have long distance, Skype, roleplay, sex." | | 25:27 | Gary | "Yeah, Daddy baby to voice command was my boss’s wife." | | 27:20 | Gary | "I just collapsed into a naked heap in the middle of the room. Zoe called back. I did not answer. I deleted Tinder." | | 30:56 | Mistress Harley | "He jumps up. He’s, like, looking around. He realizes only Mistress Harley can be doing this to me right now. And so he gets on his knees...I’m just laughing my ass off. I’m like, you can go to bed now. This was just for my amusement." | | 36:54 | Mistress Harley | "There are just like, hundreds of these guys just so desperate to give women their money because... it’s satisfying for them to feel like they’re serving a superior and beautiful woman." |
Timestamps for Key Segments
- 03:31 – Cherry Zonkowski’s story begins
- 09:12 – Skype kink scene with the Navy officer
- 11:44 – Breakup with "Captain Underpants"
- 13:53 – "Hello sailor" text and power exchange
- 14:19 – Escalating fantasies; the relationship’s end
- 16:28 – Story wrap-up and reflection
- 17:27 – Gary Pinsky’s story begins
- 22:08 – Creation of “Big Daddy Longstroke” Skype persona
- 25:27 – Accidental voice command mishap
- 27:20 – Aftermath and personal resolution
- 30:31 – Mistress Harley’s story begins
- 32:32 – Discovery and entry into financial domination
- 36:54 – Reflections on financial submission dynamics
- 38:46 – Final challenge to the audience
Tone & Style
The tone throughout is brutally honest, irreverent, and vulnerable, punctuated by laughter, shock, and moments of pointed social critique. Storytellers maintain intimacy with the audience, often breaking tension with wry self-awareness and humor. Dixie, the host, encourages sensual curiosity and non-judgment throughout, framing these tales as vehicles for self-acceptance and transformation.
Conclusion
Episode 29 of Bawdy Storytelling is a rollicking, raw, and radically honest journey through modern sexual experience at the intersection of flesh and fiber optics. From digital domination and roleplay faux pas to self-discovery in the data age, these true stories shine a sex-positive, human light on the infinite weirdness of sex and tech.