It was a combination of long-term interest, curiosity and financial strain that led me to finally create an online escort profile. I was riddled with doubts and fears mixed with immense excitement as initial messages started filling my inbox. So many questions entered my mind as the distant idea of becoming a sex worker was edging closer and closer to becoming a reality. How would this affect me emotionally, mentally, sexually, and spiritually? Did I have the skills necessary to navigate these new sexual situations? Would I enjoy myself? Is it okay if I enjoy myself? Would I not enjoy myself? Would I keep going anyway? Was I worth the money?
Eventually I braved a reply to one of my messages and solidified my very first booking. The client ended up being an incredibly sweet man in his late seventies who has lived in the Castro for over fifty years. He had two hearing aids that emitted faint, high-pitched ringing, and because of this he didn’t hear or respond to most of what I said during sex. He rode my dick until we both came, and I left feeling not much different than when I had arrived. It was the easiest and most lucrative hour of my working life to date, and it does not make for a very interesting story.
Now as for my second client, we will refer to him from here on out as Ron. Ron booked me for a two hour dom session. I had zero experience in this field of play, and Ron mentioned that he had never done anything like this before either. So, I reluctantly told him I was an old pro and would walk him through it every step of the way. I could consult with my friends in the trade and browse the internet for tips and ideas, and I was feeling oddly confident in my ability to wing it. The one thing that had me feeling a bit trepidatious was the two hour time frame Ron booked; my first client only booked me for an hour and even that session was a difficult exercise in filling my time.
The master-servant banter had already begun via text before my arrival at Ron’s house. I had the ingenious idea of telling him I would be late and that he would wait like a good servant, so I now had only an hour and forty-five minutes to fill. As I punched in the code to his unit on his building’s keypad, I matched it to the directory and realized that Ron was his apartment building’s manager. He buzzed me in and, per my instructions, was huddled on all fours next to a chair he had waiting for me. He was a white-haired asian man with a small frame, and his forehead was nearly touching the ground in front of him. He lifted his gaze enough to catch my yellow Doc Martens strolling toward him and then lowered his head back down.
I took a moment to look around the room. He had clearly lived in this place for a very long time; there were items from around the world on every wall and on each shelf and surface. Most notably, there were giant, elaborate Christmas decorations everywhere — a santa climbing a ladder to the top of a Christmas tree sat next to an animatronic Rudolph. For context, it was mid-March. Perhaps most jarring, however, was the dreadful, over-produced cover of a vaguely familiar early 2000s pop song that was blasting from his stereo. Nothing about the scene screamed “sex” to me, but I had popped a Hotrod 5000 about 40 minutes before arriving, and I was already rock hard.
I sat down in the chair and told my new servant that I required four things: my payment, a glass of water, a wet rag, and a dry rag. As he fumbled around the house for these items the song that was playing changed. I was now listening to an a capella group covering the Bruno Mars song, “Uptown Funk.” I realized then that the playlist consisted of songs from TV singing competition shows like The Voice and The Sing-off, and these were the studio versions of the contestants’ songs. I concluded that my next instruction would be to tell Ron to turn this shit off as quickly as possible; but somehow a morbid curiosity won out, and I decided to wait and see what horrible soundtrack would juxtapose my masterwork. Ron returned with my requested items and laid them at my feet while resuming his position. I counted the money and put it in my pocket, and I began sipping from the glass of water. I put my right foot on Ron’s knee and told him to wash each of my boots with the wet rag and then dry them with the dry rag. As he went to work scrubbing off the dirt I grew quite confident in myself even though I had absolutely nothing planned after this one shtick. “I can do this.” I thought to myself. “Don’t believe me? Just watch.”
It didn’t take long for things to start getting weird. Ron was so nervous that he was visibly shaking and sweating all over my boots. He looked to be in anguish already and we had only just begun. I had to call a time-out. “Look Ron,” I blurted out, “I can see that you’re quite nervous. I’m here with you for this, and you are going to get what you paid for; I just need you to take a deep breath before we keep going.”
He squeaked out a quick, “Thank you, Sir,” and took a deep breath. “I’m sorry I’m so nervous. It’s just that, I’ve never done anything like this before. I was recently widowed after thirty-one years.”
I glanced up at a photo I had grazed over during my initial scan of the apartment. A handsome man in his late fifties stared back at me from within the frame. Next to him on the table, the block letters that spelled out “Noel” had now become an ominous presence where they were only slightly comical to me just a few seconds earlier. I had stumbled not into the home of a man too neurotic or lazy to take down his Christmas decorations but into a time capsule. My chest grew tight as my heartbeat quickened within it. I struggled to figure out the best way to respond to Ron’s revelation. After a quick but intense internal deliberation, I settled on, “you missed a spot. Start over.”
My boots were clean before I knew it and my confidence in my ability to come up with new activities was waning. I made ron give me a foot massage and then a full body massage, but time seemed to be standing still. When that was over I remembered a trick that I had learned from a sub friend of mine. I was down to my jockstrap and I told Ron that he could take it off of me and smell it. When he had had his fill, I told him that I would now allow him to suck my dick. As his mouth got inches from me I shouted, “Not so fast!” He halted in mid air and I explained that he could suck my dick, but he would have to start “here” (I pointed to my toe) and lick every inch of me until he got to my crotch. Then and only then was he allowed to put me in his mouth. He got to work, and work it was. He ran out of saliva around my ankle bone and proceeded to scrape his dry tongue across the hair on my legs. A few times he skipped a spot on my skin and I made him go back over it. The experience was not an enjoyable one for either of us. As he inched up my leg, I watched one of his two cats bathing herself in the sunlight on the floor. I became suddenly amazed at the hours per day a cat spends immersed in this horrid activity. If I were a cat, I would certainly be a dirty one. Ron finally made it to my member and an arid mouth closed in around it. After one stuttered attempt at a glide up my shaft, my blow job had officially begun.
Once his salivary glands were back in action, Ron actually turned out to be quite the cocksucker. He was getting me dangerously close to finishing and we had too much time left for that to happen, so I changed things up. I made him get on the bed and lay on his back with his head draped over the side, and I began fucking his mouth. He was easily able to take every inch of me down his throat as my balls smacked into the bridge of his nose. This new position was not helpful at prolonging our session; an orgasm was close at hand, but I did not want to stop. “You took a boner pill, Tom.” I said to myself, “You can cum again after this. You could probably cum five more times after this. No need to hold back now.”
I made quite the scene during climax. I threw my head back facing the ceiling with my eyes closed and yelled as I pumped buckets straight down Ron’s throat. I opened my eyes after my final convulsion and pulled my cock out of Ron’s mouth. I was now viewing my surroundings again without the clouded lens of semen. A theater kid’s rendition of Carrie Underwood’s “Jesus Take the Wheel” was screeching out of the stereo. Two cats were now pacing and staring at me while emitting deep meows. Ten times as many books about cats beamed reflected window light into my eyes from their laminated covers. I looked down, and Ron was still choking — actually choking and coughing — on my load, almost alarmingly so. And I was abruptly and keenly aware that I would not be cumming again this afternoon or, quite possibly, ever.
I sat down on the couch and told Ron I needed a break. “And I may or may not let you touch me or yourself again for the rest of my time here,” I added. Ron sat down on the floor by my feet looking up at me. We had an hour to go.
Thankfully, Ron broke the silence first. “That whole thing just gave me déjà vu,” Ron exclaimed. I inquired further and he explained that when he was in high school an older jock would take Ron to a janitor’s closet and make Ron do things to please him. The older boy threatened to spread rumors about Ron if he didn’t do what was asked of him. Ron told me stories of the older boy making him wear his jockstrap as a hat while he spit saliva and cum into Ron’s mouth and called him his bitch. Ron loved every second of it. Ever since High School he had a fantasy of reliving that relationship, and until now he hadn’t fulfilled it. Even his late partner was uninterested in the particular role play Ron desired.
I asked about his partner and Ron was eager to talk about him. I learned that Hugh was a man of larger build and Ron had taken care of him in their home for the last ten years before he finally succumbed to cancer. Hugh’s favorite DVD to watch was Terry Fator and his Cast of Thousands, and his bellowing laugh that once echoed the hallways was the greatest absence that Ron now felt in their home. I told Ron about my partner who had passed less than a year prior. It felt inadequate as an attempt to relate — I hadn’t even been alive as long as Ron and Hugh had been together — but as we traded stories about the little visits our loved ones make to us in the days and weeks following their passing, I could tell that Ron felt he was in good company. The conversation eventually lightened as we discussed other topics. I even learned that Ron’s retirement dream is to move back to the Philippines and build a treehouse resort. The second hour of our meeting could not have been as starkly different from the first, but the catharsis of each was equally as palpable.
When our time was up I began to get dressed. Once I stood up after lacing my boots, Ron was suddenly right there hurling himself into me and wrapping his arms around my neck. A muffled, “Thank you. Thank you. Thank you,” could barely be made out near my shoulder. I held him close in a final embrace and made my way back out of his building.
I decided to walk the two or so miles home to reflect on what had just happened. I found myself thinking about something a friend told me when I said I was interested in getting into the “trade.” He told me that when two people experience an intimate connection, their limbic brains create a permanent mark on one another. I was thinking that I couldn’t be happier with the lasting marks Ron and I had left on each other when my phone suddenly vibrated in my pocket. It was an email from Ron in which he praised me and thanked me profusely; it was truly a beautiful and emotional thing to read. Perhaps my favorite quote reads as follows (English is not Ron’s first language): “Can’t thank you enough, as I consider our meet, as one of the best chapter in my life, you being the main character to it, made one soul whole again, and forever remember our encounter.” He signed it, “Can I be your slaveboy? Ron.”
During the rest of my walk home, whatever remaining feelings of stigma or uncertainty I was holding onto with regards to my new chosen venture gently made their way down my body and escaped through the soles of my shoes to be left on the sidewalk somewhere around Fillmore and Post. When I got to my front door, it felt different than just arriving home, it felt like I was stepping with both feet into the next chapter of my own life; and I was doing so with 500 more dollars in my pocket. I went upstairs, and before I could even manage to take off my boots I opened my computer and listed “dom work” on my escort profile.