My Night With Marilyn

Written by Jeff York
The American Academy of Art in Chicago
Jeff is a creative powerhouse. As a film critic and charter member of the Chicago Indie Critics, his reviews have been published by the Examiner and Creative Screenwriting magazine. As a writer, he was picked by the International Screenwriters Association as one of their “25 Screenwriters to Watch” and is a member of the Chicago Indie Critics, the ASPCA, and SAG-AFTRA.
As an illustrator, Jeff’s cartoons have appeared in various books and publications from the Chicago Tribune to Playboy to W Magazine and his caricatures hang in celebrity’s homes. And on top of all that, he has been an influential creative director in the Chicago ad world for decades.
You can check out some of his incredible illustrations and his personal movie site, The Establishing Shot.org, which is read in 27 countries. Jeff still lives and works in Chicago, ironically two blocks away from the old Playboy mansion.
TheEstablishingShot.org | RottenTomatoes.com | PipelineArtists.com | JeffYorkCaricatures.com
@jeffyorkwriter on Twitter | @jeffyorkchicago on Instagram and Threads | @jeffyorkwriter.bsky.social
Hosted and produced by Peter Griffith; contributing producer Rob Wallace.
Meet Jeff York, a hapless 19-year-old who grew up in a town of 700, a Mayberry as he puts it, with few prospects. But his venture to college in Chicago changed all that when one fateful night, he hits a formidable bump, head-on. Marilyn Chambers, the most famous porn star on earth.
Hear for this semi-steamy coming-of-age story. These are the actual events that unfolded for an innocent college nerd and the lesson learned from his happy ending – Some things are worth waiting for.
Published March 29, 2025

Transcript: My Night With Marilyn
[ appropriate music ]
HOST: Today on campus, it’s 1980.
If you were a teenage boy around that time, your perceptions about women and sex would have been molded by some pretty provocative propaganda.
Iconic movies like ‘Porky’s’ and ‘Animal House’ glorified the quest of losing your virginity and made college a mecca for this endeavor. Rock bands like Foreigner cried out that the need for sex is ‘Urgent’ and Rod Stewart yearned, ‘Tonight’s the night’. But it was a guy named Meat Loaf who sang probably the most overt and famous rock song about going all the way, ‘Paradise By The Dashboard Light’, with Yankees announcer Phil Rizzuto literally doing the play-by-play of a young couple rounding all the bases.
In today’s episode, we meet Jeff York, a hapless 19-year-old who grew up in a town of 700, a Mayberry as he puts it, with few prospects. But his venture to college in Chicago changed all that when one fateful night he hits a formidable bump, head-on. Marilyn Chambers, the most famous porn star on earth.
Stay tuned for this steamy coming-of-age story. These are the actual events that unfolded for an innocent college nerd and the lesson learned from his happy ending – Some things are worth waiting for.
[ Marching band music ]
This is Once, In College. I’m Pete Griffith. Today’s episode was a real-life experience written by Jeff York.
Jeff is a creative powerhouse. As a film critic and charter member of the Chicago Indie Critics, his reviews have been published by the Examiner and Creative Screenwriting magazine.
As a writer, he was picked by the International Screenwriters Association as one of their “25 Screenwriters to Watch”.
As an illustrator, his cartoons have appeared in various books and publications from the Chicago Tribune to Playboy to W Magazine and his caricatures hang in celebrity’s homes.
And on top of all that, Jeff has been an influential creative director in the Chicago ad world for decades. Which is where we first met.
[ Bells from campus tower ]
But enough with the resume, class is about to begin. Here’s Jeff’s story, in his own words, from a time once, in college.
[ appropriate sounds ]
NARRATOR: Like many who entered college still a virgin, losing my innocence became a preoccupying thought. In high school, I had experienced some vague fumbling about in a backseat or two, but I’d never been intimate with a woman below the belt and certainly had never even been in the presence of a nude woman in my life. Being a virgin in high school during the late 70s was more common than not, but as I entered art school in 1980’s Chicago, I was such a hopelessly inexperienced nerd that John Hughes could have cast me in any of his earliest production as “Virgin Doofus #1.”
Still, I carried a condom on my person at all times. Just in case.
I tried dating in college, but most of those I went out with were sweet girls who were virgins as well. I also found that they had no burgeoning desire to have sex like I did, and even if they were horny, often I discovered that they weren’t exactly lusting after me. Most of my dates ended with the words that always felt like daggers from Caesar’s betrayers: “I like you as a friend.” Thus, my sexual activity during college existed solo and solely in rushed moments here and there in my dorm room until my roomie returned, or in a communal bathroom stall flipping through a dirty magazine. I could only dream of graduating from glossy images to the real McCoy, keeping a mental checklist of boxes in my head that I would someday discover including, dare I say, touching, probing, numerous positions I’d discovered in the book The Joy of Sex, as well as ingesting the tastes and smells I was only able to read about. And until that time, I would be just a hapless, 19-year-old virgin with few prospects and very little chance of having sex of any kind.
Then, one Friday afternoon, as my drawing class ended at school, I was feeling productive about the day’s output. I had worked my charcoal stick down to a nub sketching an attractive young model for the better part of an hour. The 20something woman was waifish and bendy with her most striking characteristic being unshaved armpits. I’d never seen such a hirsute woman before, and it dazzled me. As I packed up my drawing supplies, I was hoping that her hippie-ish visage might make for some unique fantasy fodder later in my dorm bathroom, but as I pulled on my spring windbreaker, I was surprised by a tap on my shoulder. It was Penny, my Bohemian, 30something classmate. And she was grinning at me like a Cheshire Cat.
“Hey, Jeffy. Wanna go see a porno?”
She called me “Jeffy” in a sort of younger brother affectation as she was at least a decade older than me. Penny had come back to school to become an illustrator, and we became fast friends with a mutual love for film and movie poster illustrator Richard Amsel. But we were just friends, platonic friends. Penny was not in my consideration set and she had a school marm vibe to her anyway with her granny glasses and bunned-up hair. She felt out of reach, out of my league, and well…old. Thus, her sexual proposal truly threw me off guard.
“A porno? Like..at the Cinestage?” I gulped. “Geez, I hear that place is awful.”
I’d never been to the Loop’s most famous porn house, but I heard patrons there would be wise to don Orkin suits upon entering such a scuzz palace. The Cinestage was less wank station and more like a filthy house of horrors. Classmates of mine told of the theater’s suffocating stench of urine, watching drunkards vomit in the lobby, and seeing rats chase up the aisles. It was a place I wouldn’t go even if I was promised a BJ there by a potential date. And that was one of my fantasies at the time, a significant entry on my sexual hopes and dreams checklist.
The Cinestage, incidentally, was owned by legendary actress Liz Taylor at the time after her husband Mike Todd had died in his famous plane crash. Todd left her his namesake theater next door as well, a grindhouse that gave the two cinemas a one-two punch of luridness. All this was rolling around in my head as I was trying to figure out how to tell Penny “No thanks” in a kind way. Which was significant, as there seemed the possibility that this older woman in my midst could perhaps be my Mrs. Robinson.
It turned out that Penny was quite savvy about porn, despite confessing to me that she had never seen one. She had done her research and discovered that the Admiral Theater on the West Side was the place to go. It was clean, well-appointed, and served as both strip club and adult cinema. Heck, it even had its own gift shop and in-house X-rated video store. “I really want to go,” Penny all but chirped, “and you, Jeffy, can be my date. Or at least, my chaperone!” Then she laughed heartily, and I wasn’t sure if her chuckle was at the thought of me being cast as her romantic lead or that knight in shining armor.
Nonetheless, I was game. So, we hopped on the El to ride across town, and while we sat in the train car, Penny informed me that the Admiral was featuring Marilyn Chambers that night. Chambers just happened to be the biggest porn star in the world at the time, one I had even heard of. The Admiral was to show Marilyn’s movie “Insatiable” followed by her doing a striptease, holding a Q&A, and then signing autographs for fans in the lobby. “Sounds like fun, doesn’t it?” she asked, poking me in the ribs. “Sure,” I smiled, unsure if she was viewing this excursion as some sort of foreplay leading up to her taking my virginity.
We arrived at the El stop closest to the Admiral and as we departed the train, I quickly checked my wallet to see if my condom was still intact. Indeed, it looked good, and I marched forth to my fate…whatever it was to be that evening. My heart was racing, awash in both fear and fantasy.
Along the way, we passed a newsstand, and I happened to notice the name Marilyn Chambers on the cover of a Club nudie magazine. “Hey, look!” I exclaimed. Before I could even think about purchasing it, Penny had shoved a ten-dollar bill in my hand. “We’ll get her to sign it!” she all but shouted. As we walked the remaining blocks to the theater, I noticed that the cover promised a 10-page spread of Marilyn, including a fold-out centerfold. This was a sign, I remembered thinking. Tonight was destiny.
As we arrived at the Admiral, I rolled up the magazine and stashed in under my arm, not wanting to come off like too much of a skeevy perv. Little did I realize that the term “skeevy perv” would turn out to almost be a compliment. Compared to most of the hopelessly scuzzy guys in attendance that evening, I was Richie Cunningham. The theater may have been a grade above the typical rotting X-rated movie house, but the clientele there certainly was not A-list at all. The ruddy-faced businessmen, the smelly drunks, and the seedy old deviants made me feel unsafe, but my better angels prevailed. I found my courage and even pulled Penny in close to me, more protective than affectionate. She was the only woman in sight, but that didn’t seem to deter her. In fact, it only jazzed her more. “You think we’ll see any of these creeps beating their bishop?” she whispered to me. God, I hoped not.
Upon our entrance to the theater section, the movie “Insatiable” was already playing. On screen, Marilyn was in the middle of a fantasy sequence where she had sex with a man, then a woman, and then the three of them all together. Finally, after numerous orgasms proving why she was such a star, the equally notorious actor John C. Holmes entered the scene. His appendage swayed back and forth like Lee Marvin on his drunk horse in “Cat Ballou.” But Marilyn welcomed John in all kinds of ways, both titillating and shocking to Penny and me. I couldn’t help but notice Penny’s breathing was getting heavier, but in the dark, I couldn’t determine if she was wheezing with lust or laughter. Finally, after the climax of the scene, Marilyn turned to the camera and begged for “More. More! More!!” The shot froze on her pleading face, the credits rolled, and the film was over.
Shortly thereafter, the lights came up as Penny quickly scanned to see if any of the raincoat crowd were “exposed” and seemed disappointed that they were so well-behaved. Then an emcee in a burgundy suit, wearing several neck chains, walked onto the stage in front of the now blank screen. A garish spotlight hit him, and the light exposed the shiny pate beneath his fussed-about combover. “So, fellas,” he bellowed into his mic. “Ready to see Marilyn?”
Everyone whooped and hollered, and rather quickly, Marilyn entered the room. She made her way to the stage surrounded by rapturous applause, dressed in little more than a see-through half-nightie, heels, and a diamond-encrusted ring. The ring was not on her finger, but just below the Dorito shaped foliage sitting above her you-know-what. “You see that?” Penny exclaimed, and I shook my head that indeed I had. As I tried to comprehend why someone would want to pierce such a sensitive area, I wondered if my checklist was perhaps too…provincial.
The emcee made some small talk with Marilyn, who seemed very demure and polite. But then some rock music started up, she disrobed and started dancing. Her moves weren’t demure; they weren’t even graceful. They were bold, broad…more like squat thrusts in the gym than a dancer’s seduction. Marilyn made a point to bend over so everyone could see her glimmering ring and the graphic sight drew all kinds of catcalls from the audience. After a few minutes of bumping, grinding, and rubbing her hands all over her body. Indeed, all over her body, Marilyn stopped. She giggled to herself, perhaps satiated, certainly out of breath, and glistening with sweat from head to toe. Penny and I were dutifully impressed.
The emcee returned but failed to keep any order. Starting the Q&A, the barrage of queries flew at her loudly and rudely with each new question worse than the previous one. It was all Marilyn could do to get a word in edgewise, though her response about who gifted her the special ring quieted them down for a moment. It was from Mr. Entertainment himself – Sammy Davis, Jr.
“We were in a hot tub together at the Playboy Mansion,” she boasted, “and he gave it to me as a thank you after we’d made love.” That sent the crowd into hysterics, and I wondered if it was really love or simply something more carnal. No matter, the crowd was all but hemorrhaging out of their seats by now, and I figured it was a good time to head to the lobby and beat the drooling vultures to the punch. Penny agreed and we hightailed it out of the theater.
In the lobby, a table and chair were set up for Marilyn with a red velvet rope to help organize the line of autograph seekers. We were the first there. On the table was a stack of 8” x 10” glossies of the movie poster for “Insatiable” for her to sign. Thinking quickly, I told Penny she should ask Marilyn to sign the magazine as she’d probably be more flattered with such a request coming from a woman. Penny agreed, but as soon as Marilyn came through the doors, flanked by the emcee and two bouncers, Penny lost her nerve. She shoved the magazine into my hand and disappeared into the now growing crowd. As I stood number one in line, a brood of drooling men quickly lined up behind me. “Got here first, hey kid?” one of them teased. “Don’t bust your nut on her!” He may have been crude, but he was exactly right. I was very worried about that. Especially because I was wearing khakis.
“Oh wow! You got my magazine!” Marilyn exclaimed as soon as she saw me. She was so impressed she planted a big smooch on my cheek. She was also so close to me, her sweat was dripping sweat on my windbreaker. The 5’7” actress stood next to me completely, irrevocably nude, her nightie tossed aside on the chair next to her. In fact, Marilyn was so close to me, I could feel the heat from her lower region billowing around my hand at my side. I could also smell her musky essence. It was unbelievable.
“Damn. This is what sex smells like,” I thought to myself. For a moment, I entertained the fantasy of her whispering a hotel room number in my ear, potentially turning my loss of innocence tale into one epic story.
Then Marilyn asked my name and instructed me to bend over. Holy crap! That got me excited and the guys behind me worked up as well. They whooped and hollered as Marilyn used my back as a table to sign the magazine. She spread out the centerfold and signed her John Hancock. Then she tapped my butt, told me to stand up again, and folded the magazine back up before handing it to me. I thanked her and was about to leave when she leaned into my cheek once again. I thought she was going to give me another kiss or maybe her hotel room key, but instead, her hot breath met my ear.
“You’re too young and sweet to be in a place like this, Jeff,” she whispered.
Then our eyes met and she looked at me like I was a little boy of nine rather than 19. “You be careful out there,” she implored as I smiled through ten shades of red.
As I walked towards the exit of the theater, Penny popped out of the crowd. Jumping up and down, she was giggling like a schoolgirl. “Omigod! That was so cool!” she raved. She grabbed the Club magazine out of my hand and opened it up to the centerfold. There, Marilyn had signed in marker, “Dear Jeff, may all your horniest fantasies be about me. Love and kisses, Marilyn.” Penny commented that it was almost sweet. It was. Almost too sweet for a place like this.
As we headed back to the El, we laughed about it all a good ten minutes. But then in the train car, we grew silent, both tired and probably a bit flummoxed by the experience. I don’t know if Penny was turned on or turned off by the events, but she made no further allusions or double entendres of a potential tryst with me. If anything, she was almost reticent, or maybe just exhausted. Nonetheless, when we looked at each other and smiled, I could see that she was not thinking of me as a romantic lead one iota. I was just her friend and a classmate. Okay, maybe her knight in shining armor for a few minutes that evening, while protecting her from a crowd that would scare anyone more than the Day of the Locust.
Her looking at me as a mere friend was such a relief. For in those moments, I realized that despite all the lure of sex hanging in the air that night, I didn’t want to lose my virginity to Penny. Or even to Marilyn, for that matter. As important, so important as it had been for me to finally have sex, I realized that I now wanted my first time to be with a woman I felt truly special about. Dare I say, I wanted my first to me for love.
That checklist in my head was baloney really. After all, I had checked several of those boxes at the Admiral, but sex wasn’t about being naked, or smelling someone’s body, or even admiring their special jewelry. It should be about more of real connection. Something far greater than anything I had on my list. And that meant, I’d have to wait. A considerable while later I was certain. But then that kind of sex would be worth the wait. Much more so than any easy conquest or even brushing up against the world’s greatest porn star. All that was just window-dressing, as one-dimensional as those magazine images I fantasized in the bathroom.
I walked Penny to her apartment door and said goodnight to her. She thanked me for the fun and for protecting her from the maddening crowd. As I walked the blocks back to my dorm room, I still felt like I could be a character in a John Hughes film, but tonight I felt much more like Ferris Bueller than Cameron. The following Monday, as I got ready for class, a thought occurred to me. I opened my wallet and took out the condom. I stared at it for a moment or two and then tossed it in the trash. I wouldn’t be needing one of those for quite some time. And I felt good about that. You can’t hurry love, as the song says. Nor sex, for that matter. At least, I knew I couldn’t. And after my insatiable night with a porn star and a female friend, I was more than fine with waiting.
[ appropriate music ]
HOST: Today’s episode was produced by Rob Wallace and myself, with much gratitude to Michael Henery who volunteered some late-night hours scrubbing the sound.
In a nice, full-circle moment, one of the first productions Rob Wallace and I ever worked on together was a television campaign many moons ago. We were two beers in at the Hotel Nikko bar in L.A. when Meatloaf himself came over and sat down next to us. We exchanged a few tips of our glasses with him, but never formally introduced ourselves. We just couldn’t figure out what to call him. What do you call him in person? Meat? Mr. Loaf?
We want to thank Jeff York again for being vulnerable enough to share his experience with us in such an honest and humorous manner. His story reminds us to never rush through the things that are most important. Taking the time to do them right will always be worth it. A podcast episode, a marriage, putting a second coat of paint on before the first one dries…
If you’d like to find out more about Jeff or his work, and you should, you can check out some of his incredible illustrations and his personal movie site, The Establishing Shot.org, which is read in 27 countries. Jeff still lives and works in Chicago, ironically two blocks away from the old Playboy mansion.
What was your most meaningful sexual experience in college? If you can share it in the comments without it being flagged or taken down, we’d love to hear about it. Or take the filters off and email your story to us directly at onceincollege.com. We‘re looking for meaningful experiences that occurred outside of a class or lecture. Which also reminds us…
Everyone appreciates a little positive stroke or two. We’d be grateful if could poke our subscribe button. Or share this episode with someone. Or simply give us a like. Any of these would be exciting for our podcast. Compared to others, we’ve only gotten to first base.
Until then, I’m Pete Griffith, back next week with more stories like this, all from a time Once, In College.
[ Podcast theme music ]