A summertime sex-story special from the archives!
Two storytellers share experiences of erotic experimentation, plus a comedic song about a hookup in Winnetka.
Wild & Sublime Podcast Transcript
#S2E31 | Two Sex Stories and a Song
[Wild & Sublime theme music]
Jessy Lauren Smith: My parents didn't raise me to hate gay people. They were more like, "Well, it's the '90s, and God says not to be gay, so our hands are tied." And then later in life, they met openly gay people, and they were like, "How could God be mad at them? They seem great!"
Karen Yates: Welcome to Wild & Sublime, a sexy spin on infotainment®, no matter your preferences, orientation, or relationship style, based on the popular live Chicago show. Each week, I'll chat about sex and relationships with citizens from the world of sex positivity. You'll hear meaningful conversation, dialogues that go deeper, and information that can help you become more free in your sexual expression. I'm sex educator Karen Yates. Today from our archives, we hear storytellers and a musician relate sexual highs and lows. Keep listening.
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Hey folks. Before we begin, I want to read a listener email I received recently that just made me feel so good. Erin wrote: "I am a graduate student, getting my master's in clinical mental health counseling… I just want to say thank you so much for all that you do and all that you and your guests have been sharing with the world. In being a new therapist, there is a lot of important work to do and knowledge to learn and absorb from the world of sex-positivity. Through listening to you and the sexperts you bring to your show, I have become inspired to one day be someone who can share this extremely important knowledge & experience with the world and make a difference. I am so empowered by you all." Thank you, Erin.
Ah, I love, love, love hearing emails like that. If you want to communicate something to me and the Wild & Sublime team, you can write to us at
So, on to the episode. It is the middle of summer, and I don't know about you, but I think it is time simply to kick back and hear some stories. Stories of folks relating the twists and turns of sex in the 21st century. So, to that end, have you ever wanted the D rather than the T? Well, the storyteller in this first segment can tell you more about that, and the predicament he found himself in. Archy Arch J is a storyteller and the curator of OUTspoken, an LGBTQ storytelling series in Chicago. This story was recorded December 2019 at Stage 773. Enjoy.
Archy Arch J: [In front of live audience] I always feel like I'm the most perverted person in a room, and I don't feel that way today. [laughter and cheers] And that is very new, and comforting for me. So thank you. I can't grow facial hair for shit. However, in high school, beards were my life. Girlfriends protected me. [laughter] Get it? Girlfriends protected me from being completely labeled a fag, and allowed me to live in a justifiable denial because although I knew what blowjobs were, and which classmates, teachers and janitors I wanted to give them to, I'd look at my reality and see a girlfriend. This allowed me to dismiss my homo urges, and made me feel so... normal. Also, as a teenager, I was just starting to discover the pleasures my body was capable of. So anyone touching it, especially someone besides myself, felt like discovering gold. Senior year, I met Cheryl. Cheryl and I met at a haunted house I went to with a group from my temple. Cheryl, who was not part of my temple, came with my friend Anne. When Cheryl saw me, she has Anne to ask me if I thought she was pretty. I looked at her mocha Filipino skin, her wavy, thick black hair, and her incredibly coordinated Bebe outfit and said, "Sure!" Halfway through the haunted house, a ghost rounded the corner and said, "Boo." Cheryl screamed and backed into my arms. And by the time we exited the haunted house, we were holding hands. A few days later, we were boyfriend and girlfriend. Cheryl had fuckin' game, and over the next few months, I would ditch my last-period study hall a couple times a week and drive from Nazareth High School down I-94 and down I-57 to Cheryl's bed, where we would mine for gold until her dad came home at 5pm. Now, the gold-mining restricted itself to the first three bases, until January 15, 1996. A day that also happened to be Martin Luther King Day. On that day, freedom rang. On that day Cheryl let me put my peepee next to her weewee, and it eventually slipped in. Neither of us said a word. But the Rosie O'Donnell show began playing in the background. And before that lesbian icon, I remember thinking, oh my god, I am not gay. I am straight. I looked at Cheryl, scared of what I assumed — I assumed it was her first time, and that she might be hurt a little bit. But she had obviously done this before and she was totally fine. So freedom continued to ring in missionary position for the next 120 seconds, until I realized I was about to come — inside a person! Rosie was still doing her opening monologue. I panicked, pulled out, and had my orgasm in a familiar spot —from my right hand and into my left. On the drive home, I felt like I had outsmarted fate. I'd had sex with a woman. Taunting be damned, I am straight. Like any teenage boy who suddenly finds himself a man, I listened to Madonna's "Evita" soundtrack on my way home. And though I had always pictured myself as Evita, I told myself now I am Che, and began singing his lines. But sometimes you can feel a sense of confidence about a lie, and even look at factual events to support your lie. But inside, you know it doesn't matter. The truth is stubborn — malleable, but unyielding. So I'm driving home and 75% ecstatic that I'd become a man. But there's 25% of me that knows that I'm still Evita, and because I'm a gross boy who doesn't wash my hands after sex, I keep smelling my hands, because I want that lingering center turn me on. But it does not, ever, at all. The next night I talked to Cheryl. No one has ever been happier about 120 seconds ever in the world. "I bought a whole box of condoms! There's like, 30 of them." Cheryl was really excited to do it again. I, however, was terrified. Terrified, because deep down, I knew our sex had been an accidental miracle. With my earlier girlfriends, sensations were new, so erections were easy to get. But by the time I was with Cheryl, I was a foreplay-jaded, 17 year old who had to use my imagination to get an erection around her. And by "use my imagination," I mean I pretended sure was Mike Szymanski from gym class, Ray the skater whose locker was next to mine, Keanu Reeves, or Tony Tedeschi, my favorite straight porn star, who came through a scrambled Playboy Channel I received in my bedroom. So that night, before I was to have sex with my girlfriend for the second time, I told myself that if I could have sex with a woman for the second time, I would earn my heterosexuality, and my homosexual desires would start to dissolve. Denial is a hell of a drug, y'all. And thus, I rehearsed closing my eyes and getting hard by imagining these naked men, and then maintaining that erection while I thought about Cheryl. All the while, I reassured myself that this is what all the boys in high school had to do to have sex with their girlfriends. And I confirmed this theory by keeping it to myself and asking nobody. The next day, practice did not make perfect, and the condoms didn't help. Putting a condom on was not as easy as my mother had demonstrated with a banana. The result was something akin to a half-eaten gummy worm begging for mercy in a Ziploc bag. My hopes I could be straight deflated and I panicked, because there was Cheryl, anxiously waiting to be pleased, and I am such a people pleaser! So I did the next best thing. The thing the men on the Playboy Channel did that now strikes terror in my fully homosexual heart. Cunnilingus. Now, I am not saying vaginas are gross. They're beautiful, I'm sure. But some people like cats, and some people like dogs, and some people like cats and dogs. All I fucking know is, I'm allergic to pussies. But my one-on-one conversation with Cheryl's vagina only bought more time. Cheryl wanted the D, not the T, and after a few more attempts, she broke up with me. Did I [inaudible]? Yes. What happened in your childhood? I'm just kidding. Did I cry a river of tears after that, lady? Yes, I did. But those tears were tributaries leading away from denial. Thank god Cheryl knew what she wanted: dick. And realized what stood in her way: my gay ass! While I was swirling around in my own world of alternative facts, Cheryl brewed some hot tea and served it up. "Hey, Archy," she said, leaving a voicemail. "I don't think someone like me can make you happy. Do you know what I mean?" It'd be another year until Matt Lebugan would show me what she meant in the back of his mom's Geo Tracker. But you know who, or what, knew? My dick. Some people say mind over matter, and sure, that can be true, especially on acid. But they also say men have two heads, and once in a while — okay, maybe once in a long, long while — it's better to listen to the one that can spit the truth, amongst other things, in your face. Thank you so much. [applause]
Karen Yates: Wild & Sublime is also sponsored in part by our Sublime Supporter, Chicago-based Full Color Life Therapy, therapy for all of you, at fullcolorlifetherapy.com. If you would like to be a Sublime Supporter, showcasing you and your business and supporting us at the same time, contact us at .
Sometimes the sex talk you get from your parents at age 10, over a Shirley Temple cocktail, is just not enough. Jessy Lauren Smith, a Chicago playwright and storyteller, performed this story March 2019 at Constellation. Enjoy.
Jessy Lauren Smith: When I was 10, my parents took me out to dinner at a fancy restaurant. In my memory, it's a seafood/Italian fusion place, but hopefully that's wrong. They ordered Pouilly Fuisee for my dad and Bud Light for my mom and a Shirley Temple for me, because this was a special occasion. They were going to tell me What Sex Is. When the waiter stepped away, they both took deep breaths. "First of all," my mom said, "sex is a beautiful thing." "Between a man and woman within the bonds of marriage," my dad added — which, duh, I knew. "In some ways," my mom said, "we feel closest to God when we're having sex." The waiter started to approach with our drinks, overheard my mom, and backed slowly away. [laughter] My dad breaks it down: "When two people have sex, the man puts his penis in the woman's.... You know what? You're here. I don't need to cover this." I got penetrative sex talk, is what I got. You might wonder why I was getting this information from my parents over clam risotto. Probably. I looked up a list of Italian seafood dishes for this story. It is not a long list. Anyway, I was homeschooled. I was homeschooled in the South by post-hippie, ex- druggie, Christian parents. It was very confusing all the time. [laughter] Like in this case, they curated this experience to convey that sex is good — clam risotto-level good. And they didn't want it to be like a thing where I could only talk to my mom about it because sex and bodies weren't just exclusive to a specific gender conversation. They wanted it out in the open, but of course, there's also the casual homophobia in the way they set it up. My parents didn't raise me to hate gay people, they were more like, "Well, it's the ‘90s, and God says not to be gay, so our hands are tied." And then later in life, they met openly gay people, and they were like, "How could God be mad at them?? They seem great!" Sometimes people change their minds when they learn something new. We've all been that person at one point or another on our way to this room. Anyway, so in terms of secretly bisexual feminists growing up in the South, I had a pretty good experience with religion. [laughter] And even though I met people later in life who strongly corrected me, I clung to this belief that the god of my childhood was real and good, and wanted us to show mercy and seek justice and look after the oppressed and wanted me to feel close to Him. [laughter] About 20 years after the Sex Talk, I'm coming off a bad breakup and not ready to get into anything serious and I'm pretty wound up, so I start dating soooo hard. I quickly get good at it because practice makes perfect, and asking questions is not actually that hard. It's boring, but I'm gaining a useful skill set and getting laid whenever I feel like it. Which leads us to John. Over text, John asks me what my favorite book is. I tell him it's "Franny and Zooey." He chooses a bar near his house and makes a half joke about getting me to come back there. This is all fine with me because I have decided that unless this guy sets off warning bells, I'ma fuck him. [laughter] When I show up at the Whistler, John is reading a copy of Franny and Zooey. It looks like he's halfway through, but like, was he...? [laughter] When I approach him and smile, he does a double take. "You're really pretty," he says. It is a genius combination of actions. I am so excited. I'm gonna fuck this guy and then steal all of his tricks! [laughter]
"So what were the best and worst things that happened to you this year?" he asks as I sit down. "I would like a large whiskey," I answer. John's super-transparent move of getting women into deep personal discussions in order to get into their pants is frankly a huge relief after a year of telling people "if I've seen any good movies yet." I haven't. And where I'm from: "America." As we keep drinking, and he keeps asking questions, I start talking about God. [laughter] I tell him a little — that's what I do when I get drunk: I talk about religion, and I ask people how old they are for some reason. I'm super fun at parties. Anyway, so I tell him a little bit about my childhood. I tell him I still go to church sometimes. He says, "But you're an artist and you're a liberal and you're, you know, bisexual. How can that work?" I don't have a good answer for this. I know it's not supposed to fit together. I know I'm crossing enemy lines from whatever side you look at it. "So you live nearby?" I say instead. [laughter] We get inside and get our clothes off. He tries to flatter me. I find it disingenuous and annoying. So I pull him into bed. He goes down on me to prove he's a feminist. And when I get bored, I pull him back up again. [Laughter] You know, you know! He had more to drink than I did and he's having trouble getting it up. He uses a toy on himself. I kind of space out thinking "maybe there isn't a God because I certainly don't feel closer to him or her now." Though my parents have been pretty specific that it was the penis and vagina insertion part of sex and I hadn't really been my experience… I suddenly tune back in. John's trying to push his half-erection into my vagina.
"Are you wearing a condom?" I say.
"Shhh," he says," I need you to trust me, Jessy."
"Why would I trust you?" I shouted at him. "You're a stranger!" [Laughter]
Five minutes later, he's driving me home. [laughter] We ride in silence. I wish I was in a cab because my thoughts feel loud and they don't really have anything to do with him. We're pulling up to my house when I blurt out: "Do you really think it's impossible for me to be... me?" He takes a long pause. "I think that your life will always be really difficult." And in that moment, I like him more than I've liked him at any other point in the evening and it's probably still part of the game, this false intimacy, but I don't know. I think I just wanted somebody to say it. When I half-heartedly kiss John goodnight and shut my apartment door behind me, I take a deep breath and close my eyes hoping that I'm in the middle of the most difficult and confusing part of my life. I wasn't. But I know he's probably right. Being a lot of seemingly contradictory things at once is chaotic and stressful. And sometimes I feel like I don't even know myself. But I want to decide, I want to decide where the lines are. I want to set the terms of who I am and then maybe change my mind later. I want to learn new things. Find out I'm wrong and I definitely, definitely want to take a shower and change out of the skirt. I get a text from John the next day asking if I want to go see a play at Steppenwolf. I do... but not with him. [Laughter, applause]
Karen Yates: Next up, where in the world is Winnetka? Well, it's 45 minutes north of Chicago, and comedian-musician Amy Do will tell you more. She appeared at our September 2019 show at Constellation.
Amy Do: Oh my God, I have fans now! Cool. One last song.
Saw his selfie, swiped right on a Sunday
Made plans to meet up on a Monday,
drove down listening to some Miley,
feeling like I was being wily...
I sucked a dick in Winnetka,
the dick of someone in a startup,
or in the Army-Navy service
Got in his car and said let’s do this
I sucked a dick in Winnetka
I built my ego from the ground up,
sure I was a little nervous,
but I'm just trying to live my life
And then when the deed was done, I climbed back into my Prius,
hoping that nobody would see this,
this dirty, dirty deed I did
I drove back feelin’ like a woman,
like a gal who takes control
but my mama raised me right
so I’m goin’ home tonight,
hopin’ nobody knows that
I had sucked a dick in Winnetka
now that I think about it why’d I drive so far,
just to get out of my car,
then get into his car, then suck his dick, get out his car, and get back into my car in Winnetka
I only come here for the fair like once a year,
but I'm not the only one who comes here in a car I swear to God,
I'm never gonna drive that far again to suck a dick!
I can get dick right where I'm at!
Thank you! My name is Amy Do! [applause]
Karen Yates: More info on all of our artists can be found in the show notes.
The work I do in biofield tuning, an energy modality that uses sound waves to help repattern your bioelectric field, can support you in getting out of stuck behaviors and become more aware of different choices. If you're interested in working with me, or learning more about my weekly group biofield tuning sessions on Zoom on a variety of topics, including increasing intuition, expanding consciousness, balancing your energy centers and more, go to karen-yates.com. That link is in the show notes.
Well, that's it folks have a delightfully pleasurable week. Thank you for listening. If you know someone who might be interested in this episode, send it to them. Do you like what you heard? Then give us a nice review on your podcast app. You can follow us on social media @wildandsublime and sign up for newsletters at wildandsublime.com. I'd like to thank associate producer Julia Williams and design guru Jean-Francois Gervais. Theme Music by David Ben-Porat. This episode was edited by The Creative Imposter studios. Our media sponsor is Rebellious Magazine, feminist media, at rebelliousmagazine.com.
Want to rev up your relationship and bust out of limiting patterns?
Host Karen Yates is an intimacy coach who works in-person with couples in Chicago to help improve their intimate communication, increase pleasure, and deepen connection in a process that is embodied, meaningful, and fun.
Go to karen-yates.com and set up a free Zoom consultation.
- STORYTELLER: Archy Arch J (3:06)
- STORYTELLER: Jessy Lauren Smith (12:11)
- SONG: Amy Do (19:06)
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- Archy Arch J – Storyteller & curator of OUTspoken
- Jessy Lauren Smith – Writer & storyteller
- Amy Do – Comedian & musician
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