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Porn Stories 2: Black Cherry

Porn Stories 2: Black Cherry

The fisting one. San Francisco 2007

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Leo Herrera
Apr 28, 2023
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Porn Stories 2: Black Cherry
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For 15 years, I worked in the Flesh Industrial Complex: porn, parties and escorting. These are my stories. Read Porn Stories 1, Podcast + X-rated film for paid members only.

Queer men are told early that sex can kill us. A virus, a bashing at a park, a fire in a bathhouse, rotting in jail for sodomy. It damns our souls too, if you believe in that sort of thing.

In rebellion, we make pleasure our axis, build subcultures and industries around it, push our body’s limits. We make pleasure an extreme sport. Our sex can be a violent, beautiful joy. 

Fisting is the Superbowl of Queer sex. To shove an entire arm into another human elbow-deep, reaching past their prostate, filling their viscera until their heart is beating at the knuckles, that requires both hypervigilance and complete surrender. A trust fall into the sex realm. 


San Francisco, 2007

The Boss looked at me and pointed at his wrist. “I need a cumshot with this much inside him or we can’t use the scene.” And nobody gets paid. 

I had just started as a cameraman for a notorious fetish studio that shot condomless porn. This was pre-PrEP and barebacking was still controversial and dangerous. As a budding HIV activist, I justified the contradiction by telling myself it was an anthropological study but really I was curious and needed the money. 

The studio was a bright loft that took up half a SOMA block but The Boss’s office was tiny and windowless. I was crammed in with The Intern and The Top. This was only my second shoot. It was a skeleton crew. The rest of the staff was leaving for an S&M conference. 

“There’s a guy from Berlin we’ve been wanting to work with and he’s only here for a day. His first movie. He’ll meet you at the location. Leo, do your thing with the camera as the scene plays out, our intern will follow your lead.”

The Intern was a skinny and pale boy my age with a spotty five o’clock shadow and cloudy blue eyes. The Top was brutally handsome, short and thin, with a dark beard and eyes like black pools. I had seen him on the cover of a tape and was also the studio’s marketing director. Both of them gave me a dry hello. They didn’t seem pleased I’d been put in charge of the scene. The Boss had a reputation for being an asshole but he had been warm with me. 

“It’s illegal to show shit, so if it gets a little messy just pan away while they wipe down.” I must have made a face because he said, “Don’t worry, you’re with pros.” I didn’t tell him I’d never seen fisting up close before or that I had stress dreams all night. Fists bursting into flowers like a nightmare Mapplethorpe. 

We filed out of the studio past the weaselly office assistant who helpfully yelled out “Get the Safeway brand Crisco, it smells better!” 


A Victorian in the Castro, painted like a gingerbread house. The owner was a drag queen who always did Madonna. “Make yourselves at home boys” he purred as The Intern handed him an envelope of cash. He pointed to the end of the hallway. “Dungeon’s all yours.” He plopped down on the sofa, lit a bowl and flipped through a Vanity Fair as we unloaded equipment. 

The “sex dungeon” was a bedroom with red lacquered walls and blackout curtains over Bay windows. A four post bed of solid steel and a sling suspended over a black leather mattress. There was also a polished Saint Andrew’s cross with leather handcuffs dangling like earrings and bafflingly, a cutout of Michael Jordan from Space Jam. “You can move Michael to my room!” The Queen yelled. 

The Top quietly unpacked an industrial sized bottle of lube with a pump top, a tub of generic Crisco, a cock ring, poppers, no gloves or condoms. The Intern set up the tripods and sand bags. Neither of them had said a word to me so I skipped small talk and loaded the cameras. 

The doorbell rang. “Your gentlemen caller’s here!” The Drag Queen’s terrible southern impression broke the tension. The Top smiled. As he went to meet the man he was about to be elbow-deep in, I took my chance with The Intern. “Have you ever shot a fisting scene?” “No. I’ve never really seen it.” he said sheepishly. “Me neither.” He scooched over and whispered. “This guy’s big in the Berlin fisting scene. Personal trainer who does an insane workout program hiking up mountains.”

The German was a mountain. He ducked to enter, his gray t-shirt bursting at the seams with muscle meat. “Hallo.” His voice was deep and his accent was thick. “Beautiful home!” I looked up stunned and blurted out “It’s not mine!” like an idiot. He smiled as if he’d lost something in translation and his soft handshake swallowed my hand. His red face was both bloated and jagged, deep jowls but swollen cheeks, veins on his temples big as my fingers.

Without saying another word, The Mountain got down to a jockstrap. His traps were pyramids, a constellation of acne on his tanned back. His pecs were gladiator breastplates, nipples like cartoon erasers. Veins snaked around his arms and legs, his belly was thick and slightly distended, his testicles were tiny, like a Roman statue. Signs of heavy steroid use and old HIV medications. 

The Top appeared from behind him with a huge grin. He looked up at The Mountain’s face, stroking the hair on his arms and flicking at the eraser nipples. The Mountain sniffed at his scalp, both men made soft growling noises. The Mountain helped The Top pull off his shirt, a streamlined body hidden in fine dark hair from the nape of his neck to his knuckles. The energy shifted to only them. The Drag Queen craned her neck to peek. 

This would be it for prologue. The studio was known for its gonzo shoots with no plots, groundbreaking at a time when Gay porn studios still attempted storylines with drawn out openings. The Intern turned on a light and the red walls vibrated. 

The Mountain climbed on to the sling like a clumsy toddler but the bed posts didn’t budge. He lifted his tree trunk legs into the holsters, exposing an asshole with mileage, waxed and bright red. I moved a light to illuminate it, pointed my camera at it and pressed record. “Rolling.”

The Top stroked The Mountain’s hole and slapped it, it pulsated, he licked at the edges, cheating his face for my camera. The Mountain whimpered. The Intern was two feet away, shooting his face. 

The Top pumped the lube and slicked The Mountain’s hole softly, it relaxed, glistening under the lights. The Top cracked his knuckles, took a fistfull of generic Crisco and rubbed his hands with the elegance of an orchestra conductor. The Mountain pulled his jockstrap to the side and his short and thin erection pointed up, he jerked it with one hand and with the other, he reached for the nightstand, grabbed the bottle of poppers, gracefully opened it and held it under each nostril, breathing in so deep he sucked the air out of the room. He politely offered it to The Top, who took a whiff. The Mountain turned an even deeper red, his veins pulsing. The Top’s neck flushed. A chemical tether joined the men and The Intern and I disappeared. 

The Top took his time but his eyes were wide and hungry. One finger, in and out, two fingers, in and out, three fingers, in and out. He was working with the contractions of The Mountain’s breathing rhythm. Four fingers, in and out and finally a thumb. I zoomed in. 

The Mountain clamped down on the wrist, he groaned and his eyes rolled back as his body accepted. The Top waited patiently. The Mountain let out a guttural sound, thick as a trumpet then he swallowed him all the way to his elbow at a speed which surprised The Top. “Wow baby, you really wanted this didn’t you?” He said with a light Irish accent. The Top made a digging motion. I pulled back to frame this small man and his entire arm inside a giant. 

Time slowed into a wave of moans and squish sounds, the smell of a locker room, poppers and generic Crisco. I was far away now, shooting a football game from a blimp or a spectator at the coliseum. If it weren’t for the time stamp on my viewfinder I would not have known how many minutes had passed. The Mountain smiled and signaled he needed a break. The Top exhaled and began his slow descent out of him.

Then The Top pulled out his arm and went pale…

A fistful of black cherry jam. Black cherry jam all over his knuckles, down to his wrist, to his elbow, dark rubies clumping on his hair, red and black in my High Def viewfinder, searing into my cornea. I panned away so fast I almost dropped the camera.

The Top turned from the yellow of an old bruise to a red hot flush. Sweat down his temples. The Intern looked up from his viewfinder and saw his arm and turned even more pale than he already was. I don’t know what color I was but I became very aware of my face. 

It was as silent as San Francisco ever got. Outside a homeless man howled over the hiss of the 33 bus. The Mountain kept jerking off with his eyes shut but the quiet pulled him out of his trance. “Everything OK? Do I need to clean up?” He saw The bloodied Top’s arm. “Oh.” He mumbled something to himself in German. 

“Cut” I said as if it was necessary. 

My pupils dilated and the room got brighter. Stay calm. It’s San Francisco, this would absolutely not be the first time an ambulance was called into a sex dungeon in Castro. I pictured the comedic logistics of getting this enormous mammal on a gurney.

I locked eyes with The Mountain. “Do we need to get you to a hospital?” The words sounded far away. The Top was still frozen next to me holding his hand. “Why don’t you clean up.” I gently patted the wet hair on his shoulder. He nodded and headed to the bathroom like a sleepwalker. 

The sound of the faucet and The Top pumping hand soap over and over. The Mountain closed his eyes again and took a deep breath, conversing with his organs. His face didn’t register pain or fear, but disappointment. “No hospital, I know what this is,” he said softly. “I’ve had an operation. My second hole is clipped.” I didn’t think The Intern could turn any more pale. “I can take a suppository. 45 minutes will stop the bleeding.” The faucet stopped. 

The Mountain climbed off the sling by himself (not that The Intern and I would have been any help) and went to the bathroom. “What the fuck” I mouthed. The Intern shrugged, slack jawed and wide eyes.

When I walked to the living room The Drag Queen was gone and The Top was sitting alone with a thousand yard stare. I knelt in front of him. “So his second sphincter is clipped, that’s why you didn’t feel any resistance. He’s going to take a suppository and can keep going in an hour.” The Master Rule floating between my words and his confusion. If he doesn’t come, we don’t get paid. “Are you OK?” I patted him on the leg. He nodded softly. “Long as he’s OK.”

After an eternity, The Mountain came out of the bathroom. He looked ashamed. “I’m alright. Ready.” He got back on the sling with no signs of struggle or pain. 

The Top tried. The Mountain tried too. They don’t call it porn “acting” for nothin’ honey. They kissed and growled again but the tether had snapped. The Top couldn’t get the fist in and The Mountain couldn’t get hard. 

“Cut. I think that’s a wrap for today.” I said in the most matter-of-fact, professional tone I could, though it felt silly we’d even tried. 

The Top and The Mountain sighed at each other with a smile. The Top helped The Mountain off the sling then went to the other room to call The Boss while The Intern and I packed up. 

As we left, The Top handed The Mountain an envelope of cash. The Mountain gave him a long hug. The Drag Queen got back. “Was this a porn shoot or a funeral?”


The office was buzzing with people stuffing videos, sex toys, signage and merch into shipping boxes. Nobody noticed we returned early except the office assistant, who looked up from his clipboard. He raised an eyebrow at The Top, who was using half a bottle of green Palmolive at the kitchen sink, lathering up to his elbows like a surgeon, sickly under the fluorescents. “He wants to see you both.” The Top dried his hands on a towel, threw it in the trash and crawled into the office.

The room felt soundproof. The Boss sized us up with piercing eyes. He said The Top’s name softly. The Top stared at the ground and shook his head. 

“I feel like a fucking amateur.” A tear was welling up on his long lashes. The aggressive, sex creature from before was gone and now he looked like a scared, beautiful little boy. 

“What happened?” The Boss held his hand up. “Wait, don’t answer that. Leo, what do you think he thinks happened?” I looked at The Top for any guidance but he was still looking at the floor. I cleared my throat. 

“He feels like he failed but from where I was, he did everything right. They hit it off great. He got no sign that something was wrong or that there was an injury. He told me that his second sphincter had been surgically clipped. I didn’t even know that was a thing.” The Boss shook his head. “Fucking Berliners.” The Top’s tear was dangling now.  

“Hey, look at me.” The Boss in a firm tone. "I'm gonna need you to let this one go OK?” The Boss pointed at his own heart and then outward in an priest-like gesture. The Top wiped his nose. “Take the rest of today off. Go home. Relax. OK?” The Top nodded. I felt like I was intruding. I had never seen aftercare between two men before. “Close the door, I want to talk to Leo alone.” The Top walked out without looking at me. 

“You took care of the situation. That takes strength.” I blushed. “One of my first sex scenes, another Top shot his dick with too much Trimix. The Bottom was riding him and his dick popped out. It was purple, almost black. He’d broken his dick. The Top fainted. I had to hold his hand in the ER, this grown man sobbing when they cut his dick to drain it.” I grimaced. “Look, porn is more than sex, it’s men and their relationship to their bodies and their emotions. Do you understand?” I did. “The thing I remember the most, is that when The Bottom dismounted and saw this blackened dick and The Top passed out, he looked back at me and asked “Boss, do you want me to keep riding?” A nervous giggle jumped from my throat. “When you have that kind of trust, you have it until the end.” He leaned into me. “And when they trust you like that, you can lead them anywhere.” 

He paid me and I left. 

I didn’t shoot porn again for six years. The studio’s films got more controversial and disturbing, showing meth use and boys looking for HIV positive loads. The Boss wrote sprawling academic essays on “viral panic” and our need to rid ourselves of the link between death and sex. I was spellbound and disgusted.

My next shoot was for a bigger porn studio. The red lacquered walls were replaced with a lush South American jungle. The dungeon was a hacienda with an infinity pool on top of a mountain near the ocean. A gang of muscled young statues having safe vanilla sex on a big budget, scripted porn. I filmed for a grueling seven days and saw very little tenderness or the kind of awareness and empathy I witnessed that day in San Francisco. Sometimes it’s hard to tell if you’ve met The Devil or a sacred monster. 


The following is raw footage of a fisting porn scene I filmed 10 years later, an orgy which went beautifully and folks had a great time! All models are over 18 with consent and model release forms. For paid subscribers only…

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