My Night With Jamie Gillis

Kim Airs
8 min readMar 2, 2020

A party. A porn star. A junky car. A hot night in San Francisco.

Jamie Gillis

San Francisco. Of course. 1995, yep. The occasion was Kat Sunlove’s 50th birthday party held at the Great American Music Hall in the Tenderloin section of the city, just a few doors down from the infamous Mitchell Brothers Theater. The perfect place for a party with a huge, wooden dance floor, a comfortable balcony that overlooked the entire space, and plenty of room for everyone and I was there.

I officially entered the world of adult entertainment in 1993 when I opened the first female friendly, well-lit adult store, Grand Opening! (get it?!) in the Boston area, in Brookline’s Coolidge Corner, to be exact. I left my job at Harvard to sell rubber dicks to girls.

I had been a porn fan since 1987, after I got divorced from a rather boring husband who complained while we were watching our first porno film together in 1984 when VCRs first came on the scene. While the images of naked people screwing were flashing on the screen, he snipped “Oh, they’re all faking it. They’re lousy actors. This isn’t doing anything for me.” But my loins were moist and I wanted more but didn’t dare watch porn again because I didn’t think I should. No wonder we got divorced.

Shortly after divorcing, I met Smuthound, who turned me on to all things sex. Including porn. And lots of it. We rented videos and I watched them, gazing from between my thighs as I was fucking my boyfriend, the way you’re supposed to. I watched porn as I bent backwards over the edge of the sofa, dangling my hair on the floor as I witnessed the upside down but still gratifying sex positions on the TV that screen the lucky bastards were getting into, even while I was getting pounded from above. It was with each and every moment of cinematic flying jizz, every moan and scream, fake or not, every plot line, costume, and sex scene that I found myself getting more and more immersed into the world I still call home to this day. I loved it.

I had heard about a party for this woman I barely knew, that it was going to be the celebration of the decade, a place where every cool porn star would show up to this party and where the public was invited, too. Kat Sunlove was the editor for the infamous San Francisco based sex rag, The Spectator, which published intelligent articles by intelligent pervs, filled with how-tos and wheres for unbound sex in the Bay Area, where you could find someone you were looking for within the most personal ads listed this side of the Mississippi. Kat Sunlove’s 50th. It was the party where I had to be.

After opening Grand Opening!, I was going to San Francisco several times a year, scooping up the city’s sex energy to bring it back to Puritanical Boston. I had apprenticed at a sex store there, made friends there, visited sex toy manufacturers, and frequented as many strip clubs, porn theaters and sex toy stores in San Francisco as I could during my brief visits. I had to be at Kat’s Birthday Party for that special night.

I borrowed a junky car from a friend and parked it in a local parking lot near the Music Hall. I slowly strolled over to the Hall wearing my short black skirt, fishnets, black heels (of course), and a sheer, black mesh shirt with a feather collar and front, allowing me to wear as little as possible but still be dressed in formal evening wear. This WAS a sex event, after all, in the city that defined them and I had to fit in.

I walked into the Music Hall and gazed over the crowd. It was like all of the porn icons I had ever dreamed of meeting were right there in front of me, having fun in a relaxed atmosphere to celebrate one of their own. I arrived solo, allowing myself time to absorb the scene and be entertained when Kat made her appearance by being inside the rear of a large, furry horse. Nothing like starting a party the RIGHT way!

There was lots of laughter generated by a host of porn stars, sex workers, strippers, photographers and sex writers of every persuasion, simply known as the sex “clitterati” of San Francisco.

After a few hours of such boundless celebration, the audience was thinning and people were heading back home to their normal routines. But those who remained lounging around on the comfortable chairs or twirling around on the dance floor, were the Gods and Goddesses of just about all of my favorite porn movies I had ever seen. I was invited to join the party, the real party, the one that I had waited all these years to be part of, the one that I now was invited to join.

The dance floor was all ours. Nina Hartley, Betty Dodson, Annie Sprinkle, Sharon Mitchell, Veronica Hart, Veronica Vera and a few other women who were the Goddesses of the Golden Age of Porn with Betty the reigning “Mother of Masturbation.” I was as high as I ever had been, induced by the drugs of fame and sex and I was now one of them.

After the delight of carelessly dancing on the floor with these beautiful and talented women, it was time to call it a night. Sitting at a table by himself was none other than Jamie Gillis, the transplanted New Yorker (like many others) who had called San Francisco home for decades. Jaime Gillis, who I had watched countless times, fucking beautiful women, talking dirty with his incredibly sexy baritone voice, creating characters from many nations all in the name of making a great smut film. Yes, Jaime Gillis. And he was alone.

Having been so sexually empowered with the Goddesses on the dance floor, I sauntered over to him and asked what he was doing after the show. He mentioned he had no plans and I casually mentioned, “Either do I.” “May I join you?” he responded.

After my pounding heart settled down below my vocal cords, I uttered a purring “yesssss” which I knew he must’ve heard countless times before yet never from me. He took me by the arm, holding it the way real gentlemen do, and we walked back to the car, talking about what a wonderful party it was.

The weather was balmy on this San Francisco night. The moon was clear, defying the cloudy evenings that define the city. I creaked open the junky car door, apologizing for the condition but knowing that he probably didn’t really care. And then the conversation started.

Here I was with a real porn star, one that I had always admired. Sitting in the car without being at a fan event or snapping a Polaroid at a porn show. He was in my car and the night was still young.

We sat and talked. I resisted sliding my hands over his pants to stimulate the cock I had seem oh so many times. For once, I felt like a kindred spirit with this handsome man and listening to his mellifluous voice held me on the very edge between being a new friend and a fangirl. We talked about the recent suicide of the adult star, Savannah, and how the media portrayed her as a victim of the porn industry. “They never focus on how many dentists commit suicide and it’s a lot more than those of us in the industry,” Jamie shared. “But no, they want to make porn the evil business and that everyone ultimately wants to kill themselves. If you come into this industry fucked up, you’re gonna leave it fucked up, too. The media will never say that.”

We continued our back and forth conversation about the adult industry and found that we had the common interest of watching hookers on the street ply their trade. He suggested we go for a drive around the Tenderloin district to see them in action.

We drove just a few blocks to begin our voyeuristic circles in the area, describing the working girls to each other with our dirty talk fantasy. What color their panties were, whether they spit or swallowed. What were they gonna charge their next john when he just want a hand job in the car from a whore. “I bet she’s gonna fuck the next guy who pulls over,” Jamie purred in his deep, silky voice. “Look over there…” Sure enough, a car with a “My Kid is an Honor Student” bumper sticker slid over to the side of the street as she leaned inside the window to negotiate with the john. We watched from across the street in a parking space, close enough to see what was going on without being thought of as a member of the vice squad. We were taking verbal bets with each other as to whether or not she would hop into the car and I can’t remember who won that night.

I was looking at Jamie while I continued to drive around the Tenderloin and casually asked him if he ever was with a woman who shot off. Ejaculated. Like I did. To my astonishment, he said he’d only seen 2 women do that before in his entire porn career and using my skills and talents to do so, I decided to show him another.

I circled the neighborhood looking for a parking lot where I could spread my legs and let him experience a different kind of female pleasure. I parked in a space that perfectly focused a streetlight right onto my moist pussy where he could see everything I was about to show him.

I was throbbing. Here I am in a car with my favorite porn star, letting his erotic voice turn me on with each and every syllable, every dirty word that spilled forward, every moan he would share as he was getting turned on with the thought of seeing my pussy in the glint of the streetlight.

I slid my skirt up then spread my legs and positioned my heels upon the cracked dashboard of my beat up car knowing I wasn’t going to do any more damage to it. I furiously began masturbating and was able to shoot off within seconds. Not a dribble, not a squirt, not just a little. It seemed like gallons being shot out of my wet cunt, all in one, huge gush.

It sprayed all over. All over the well-worn steering wheel, the torn seat, the ratty carpet, the cracked dashboard and beyond. I put on the windshield wipers and they didn’t do shit. The rain was on the inside of the car and it looked like a downpour had just happened on the streaky windshield. I was spent.

“Wow. I’ve never seen that before,” Jamie breathed, wide eyed. “Never that much….” His voice tapered as I was gasping for air, regaining my breath after having what seemed to be an out of body experience.

We both chuckled about the windshield wipers and opened the windows to air out the car, which at that point, smelled like zoo. It was time to call it a night so I started the car and rumbled a few blocks to Jamie’s house where I dropped him off. On Bush Street. In San Francisco. 1995.

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Kim Airs

Of Grand Opening! Sexuality Boutique www.grandopening.com Sextoy specialist, sex educator, sextoy reviewer and experiencer of all thing sex! All social @KimAirs