An exploration of the power dynamic in leather sex.
This is a true story of actual events that shaped my understanding of the Leather community and informs my belief in the role of dom/sub and the willful exchange of power.
It was a Friday night in the Castro and I was 20 years old but had a fake ID. I was horny and wanted to have sex with a big leather daddy, something I had only fantasized about. I picked Headquarters, the uniform bar off 18th Street in the heart of the Castro. It was 1990 and AIDS had already swept through the community establishing in its wake the negative connotation for leather-sex as irresponsible or dangerous. I was not deterred.
I walked into the bar and ordered the King of Beers, a Budweiser, and asked for two dollars in quarters. I loved pinball and they happened to have a couple of pinball machines right next to the bar where the hottest man was sitting. I floated over to the pinball machine, bent over to put my beer on the floor, and fed the machine its quarters. Nothing.
I was really expecting a comment or something from the man at the bar, but he ignored me. Two hours and at least a dozen multi-balls later and I had not gotten a single reaction from this man. I was bitter and frustrated as the lights came up and the bar started to close.
“You ready to go, boy” was the first thing I heard the man say. I was like Jack Russel Terrier on meth. I was bouncing around, so excited that I couldn’t help myself. As we exited the bar, I told him we could walk to my apartment just across Market Street on Castro Street. He said we were taking his car. I reiterated that it would be harder to park the car and that I lived literally 100 feet from the bar. He stated one last time that we were taking the car and I understood that I needed to shut up and get in the car.
It was a brand new Volkswagen Golf–pristine white. I kind of laughed to myself- some leather daddy, huh? When we get to my apartment, he pulls up on the sidewalk and parks illegally in front of my bay window at the garden level.
He tells me to get his bag from the back of the car as he walks to my door. I could barely lift the huge leather bag and I began to wonder what I was getting into. Not enough for my erection to go down, but a little fear creeped in.
The apartment I was living in was located right above Market Street on Castro. We had a beautiful bay window that faced the street at the garden level. I was living with someone I had fallen in love with the previous year during a computer convention my first time in San Francisco. Falling in love with this man literally saved my life. It was his choice not to be dating when I arrived, but I never though I would trick with someone in his apartment, especially not with him asleep in the back room.
We get in the door and the leather daddy has me put the bag down. He tells me to strip naked and I start to suggest going to my bedroom…then shut up and stripped naked. He walked over to the bay window and opened the curtains all the way. The bars had just closed and people were walking by the garden level flat and looking in to see us. They were forced to walk around his car that was blocking most of the sidewalk, but that gave them an excuse to look right in the bay window. I was a little freaked out, as small crowds would form and then dissipate.
Once we got started, I don’t remember thinking about the people outside for even a second. I was so focused and driven to be the best boy this leather daddy had ever played with. I had previously had some serious dental problems and pain was something I was used to. I figured I had an advantage here.
He put a dog’s choke collar on me with the teeth pressed against my neck. Then he put a cock and ball separator on me and ran a chain through the loose part of the collar through my legs and tied it to the door handle. I could hear the love of my life stir a little in the back room and my heart was racing.
He had me walk towards him, away from the door. Each step pulled my nuts and dug the teeth of the collar into my neck. He encouraged me to continue like he expected it. It was supportive, but had the tone of, I know you can do better, come on. And I did.
What I remember next was that he had his arms around me and my back was pressed against the door. I was too excited to realize that I had choked myself out. When I couldn’t breathe, he picked me up and walked me back to the door where the collar was released. He loosened the collar and could see the 40 little bruises around my neck. He told me I was a good boy and stroked my head while I pressed against his hairy chest, shaking just a little but happy, so happy.
He then pulled out a cat of nine tails and had me reach out to hold his nipple ring. He told me that he was going to whip me with this thing and that when it got to be too much, I would let him know by releasing his nipple. He would stop the second I indicated that I had enough.
As he began lightly whipping my sides, cock, and legs, I tried not to wince or express discomfort. He picked up the pace and increased the strength of each hit. I could feel the residual pain when the whip would come away from my body, but I dealt with it. He never once asked if I was okay–why should he? At one point, I felt my legs start to buckle but caught myself. I thought, surely I have to let go, right? But I was driven to be the best he had ever seen. He stopped a couple minutes later. He praised me and grabbed a towel from his bag. I could see blood on the towel and realized that I was bleeding.
He began reprimanding me in an educational sense about my sense of safety. He insisted that I learn boundaries and explained that I should have stopped him earlier than I did. He never apologized because I was in control. But I could tell he didn’t mean to cause me to bleed. He bandaged me up and packed his things. He gave me his name and number and told me to call him at 10:30a.m. tomorrow if I was ready to learn more.
He left, and I went to set down and realized it was probably best not to sit on my ass anytime soon. It was so red and sore. I went to get in the shower and masturbated for what seemed like all night. I couldn’t stop thinking about him.
At 10:30 the next morning, I called. He answered on the first ring saying, “good boy” and I had tears in my eyes. I was so into this guy that I couldn’t believe it.
He explained that he was duly impressed and was considering making me an offer. He said he had never offered this to anyone without a thorough series of tests. He offered to let me come to his compound in Palo Alto and meet his boys.
He had 3 full grown men that he referred to as his boys. They were his to command and they provided for his pleasure only. They didn’t work, or wear clothes and they attended to him at all times. They were stunningly gorgeous and they had amazing bodies. They would take the scraps of affection that he would offer and they seemed content and fulfilled.
One of the boys had been there for 15 years and all three were committed for life.
After my visit, he gave me a couple days to think about what I had experienced. Then he offered to make me one of his boys. I was flattered by the offer and after talking with his boys each of them had an initiation story that sounded intense. They had to go through a lot before they got their offer. I got mine right away.
I would have to give up my six figure job where I had already established myself in the industry I was in, my apartment, my friends, everything. I would never wear clothes again and I would have my head shaved and his information tattooed in a QR code on the back of my head (this was before QR codes were common). I would become his property and he would take care of me for life.
I had one week to decide and surprisingly, it became the hardest decision I have ever made. I chose not to take him up on his offer. I knew there would be no second offer or a chance to negotiate and it broke my heart that I would never see or hear from him again.
Come to find out, he was the Dean of Stanford’s Psychology Department. He was compassionate and one of the hottest men I have ever seen. I was so close to taking him up on his offer and still today, I think about how different my life would have been.
What I learned from the situation is invaluable. I was in complete control the entire time even though I wasn’t aware of it at the time. I chose my limits and the motivation to allow myself to experience more pain for his pleasure drove me. I do not regret a single moment I spent in his presence and when times are rough, I can’t help but think that maybe I made the wrong choice.