Bawdy Storytelling – Episode 70: ‘F. Scott Surprise’ (Shawn Silverman)

Episode Overview

This episode of Bawdy Storytelling, hosted by sexual folklorist Dixie De La Tour, features storyteller Shawn Silverman as he recounts his adventures exploring kink and sexual liberation after ending a long-term, monogamous relationship. With classic Bawdy humor and explicit honesty, Shawn’s story navigates themes of sexual awakening, BDSM dynamics, and one especially memorable tribute set at the gravesite of literary giant F. Scott Fitzgerald. The story is rich with vulnerabilities, humor, and insight into the evolution of sexual identity—making for both a poignant and outrageous adventure.

Key Discussion Points & Story Arc

1. A New Beginning After Heartbreak

[02:50] – [05:40]

• Shawn returns home on his 28th birthday to find his partner of seven years gone and a steel case left behind: “one of those beaded stainless steel rods for shoving up your ass.”
• The breakup is mutual in its necessity: his ex needed to live her queer truth; Shawn craved kinkier sex.
• Shawn reflects: “I really wish she’d figured it out before we’d signed all the mortgage paperwork, though.”
• Inspired by post-breakup advice, Shawn dives into missed experiences—from home décor to fried chicken to casual hookups.

2. Online Connections and the Flapper Philosopher

[05:40] – [07:40]

• Rediscovering OkCupid, Shawn crafts a profile blending “Marxist feminist politics” and kink interests.
• An algorithm pairs him with Nikki, a self-described “flapper philosopher,” with shared tastes in literature and adventurous food.
• Their witty online exchange blooms into meeting for drinks. Nikki is compelling: “tall...long dirty blonde hair...blue rectangle rim glasses and a very low cut dress with very large tits.”
• They quickly begin dating, chemistry fueled by a shared sense of humor and sexual curiosity.

3. First Steps Into the Kink Scene

[07:41] – [10:45]

• Nikki initiates Shawn into kink, revealing both her masochistic desires and her history: “scars on her back from a flesh hook suspension... pictures on her fetlife of needle play.”
• She teaches him about “risk aware, consensual kink”—a step beyond the familiar “safe, sane and consensual.”
• Together, they explore a host of new experiences: public sex, ass play, bondage, saran wrap mummification, and degradation play (“...write mean things about her with markers and also with the Wartenberg wheel.”)
• Shawn openly credits Nikki as his “kink mentor,” playfully narrating their escalating escapades.

4. Switching Roles and Deepening Experience

[10:45] – [12:00]

• The couple realizes that “if I was going to be doming all the time, this just wasn’t going to last.”
• Leaning on Nikki’s experience, Shawn is introduced to submission—his first experiences being tied up, face-fucked with a strap-on, and even enduring a rope rig involving his ponytail and an anal hook.
• Shawn, reflecting on one invention: “I’d recommend that to literally anyone. Like, grow your hair out or whatever you need to do.”

5. The ‘F. Scott Surprise’ – The Climax

[12:01] – [13:35]

• Shawn orchestrates a dramatic surprise for Nikki: blindfolding her, binding her wrists, and driving her to a mystery location at night.
• After some wayfinding mishaps (“miracle she didn’t trip over something”), he leads her, still blindfolded, to a granite slab.
• He pushes her “down to her knees on a cold granite slab.” Their play intensifies despite the cold.
• At the moment of disclosure, Shawn removes her blindfold to reveal: “coins and flowers and books and the granite slab beneath her, which read: ‘So we beat on, boats against the current, borne back ceaselessly into the past.’...Francis Scott Key Fitzgerald and his wife Zelda.”
• Nikki is ecstatic; both agree: “F. Scott would have been really pleased with this tribute.”
• The story ends with more passionate sex in the car and back home: “She sucked my dick like a pro while fucking my ass with a dildo until I flooded her mouth for the first time in my life.”

6. Reflection and Life Beyond the Story

[13:36] – [14:33]

• The relationship soon ends, but with positive outcomes. Nikki finds her dream dom; Shawn embraces a “poly queer lifestyle.”
• “...after seven years of a pretty vanilla marriage and her spending most of her adult life in a dungeon, I could still find some ways to surprise her.”

Notable Quotes & Memorable Moments

• “[My ex] left me a birthday present in a steel case...one of those beaded stainless steel rods for shoving up your ass.” (Shawn, 02:52)
• “She was the first person to finger my ass while blowing me.” (Shawn, 09:00)
• “She taught me a lot about risk aware, consensual kink. Which is not a thing I’d ever heard of.” (Shawn, 08:45)
• “One day she came over, I was pre tied up and she tied a piece of rope to my hair...and the other end of the rope to an anal hook...whenever my butt wasn’t getting fucked too hard, my neck hurt. I’d recommend that to literally anyone.” (Shawn, 11:27)
• “I pushed Nikki down to her knees on a cold granite slab...when she heard me unzip, she was ecstatic.” (Shawn, 12:16)
• “The granite slab beneath her...read: So we beat on like boats against the current, borne back ceaselessly into the past.” (Shawn, 12:40)
• “She told some of her friends what I’d done and they described it as a life story–altering sex, which was a bucket list item I didn’t know I had.” (Shawn, 14:30)
• “...I could still find some ways to surprise her.” (Shawn, 14:32)

Timestamps for Key Segments

• [02:50] Shawn’s breakup, kinky birthday gift, and beginning of sexual reawakening
• [05:40] Creation of new OkCupid profile, meeting Nikki
• [07:40] Nikki introduces Shawn to risk-aware, consensual kink and BDSM play
• [10:45] Exploration of switching roles and advanced BDSM scenarios
• [12:01] The “F. Scott Surprise”: the public sex act at Fitzgerald’s grave
• [13:36] Reflections on the past, relationship closure, new communities

Tone & Style

The tone throughout is candid, humorous, sometimes self-deprecating and always sex-positive, mirroring the ethos of the Bawdy Storytelling podcast. Shawn is earnest and matter-of-fact about the explicit details, openly sharing his process of discovery without shame or bravado. Dixie’s introductions frame the episode with warmth and celebration of genuine sexual narrative.

Final Thoughts

“F. Scott Surprise” is a celebratory account of rediscovering authentic sexual joy after loss, set against the backdrop of queer, kinky, and literary subculture. The episode champions exploration, communication, and creativity, all delivered in Bawdy’s signature entertaining and insightful style. Listeners, whether experienced or new to kink, will find both humor and humanity in Shawn’s journey, making for a memorable chapter in the Bawdy Storytelling series.