I drove to Jerry’s house listening to My Favorite Murder, hoping my sister’s Lyft would arrive after me so she wouldn’t have to wait alone outside at night. Thankfully I made it there first. Bert came outside and helped me parallel park in front of the house on Jerry’s cobblestone driveway. He wasn’t kidding when he said it was beachfront property. As soon as I stepped out of my car, I smelled the briny scent of the ocean and heard the waves crashing nearby. Bert led me in through a giant wooden door that pivoted on a central point. Through the door we stepped onto a floating walkway. Each step appeared to be floating on a waterway decorated with glistening cerulean blue tiles. At the end of the walkway was a sequestered off hot tub with a clear glass divider that blended into the water walkway. Bert opened the door to the house for me and I looked around, trying to absorb the feeling of being really rich for a moment. Bert handed me a thousand dollars, half for me, half for Sofia. The two men continued their conversation as I took a moment to remove my shoes.
Jerry: —That’s why I told them to sell it. They’ve got so many, and the demand right now won’t last. You remember the Dobson Report? Just take a look at these numbers.
Bert: I know and I agree 100%.
I was distracting Bert simply by existing in such proximity. I took my time settling in, still nervous, uncertain how all this would go down. I checked my phone every few minutes, waiting for a message from Sofia.
Me: Am I interrupting your work?
Bert: Of course not. Come over here.
I obliged and we began the session. I pretended to be this hyper sexual little minx who he had to chase and who was full of giggles and coy looks. It’s an exhausting yet familiar routine. He picked me up like a caveman and took me out to the porch to fool around. He removed my clothes and I unbuttoned his shirt while he took off his pants. He penis was like a happy puppy’s wagging tail. He was so aroused it consumed him entirely and I knew he needed to come or else he would continue hounding me. However, Sofia was en route. I excused myself to check my phone and found that she had just arrived. Bert walked out to get her, and I greeted her in the doorway, trying to act chipper instead of full of over-protective concern. It was her first outcall, and I hoped entertaining this elderly man wouldn’t be too daunting a first experience. I handed her her cut of the money, and she warmed up a bit. I was still naked aside from my shirt.
Jerry: You don’t have to be naked. I want you both to feel comfortable.
I appreciated the gesture, as did Sofia who took a seat at the table beside Jerry, who was still answering emails, even though it was half-past 3 a.m..
Bert, satisfied Jerry finally had his own distraction, once again carried me off to the porch. It wasn’t the most private area. From the chaise lounge where we were, I could clearly see the neighbor’s home and the beach, which was empty, thankfully. Bert removed his clothes again, revealing his bulbous pot belly and pink genitals, covered in a fluffy sprinkling of light brown hair.
Bert: Jerk it.
It was half demand, half dirty talk. He, indicated his erection for additional clarity.
Me: Nope.
I let out a gleeful laugh, because it’s much easier to deny men when you’re cute about it.
Bert: C’mon. You know you want to. It’s a nice cock.
Me: Nope.
Bert: Why not?
Me: I don’t want to.
Bert: Don’t you like it?
Me: It’s fine.
He looked at me with the greatest incredulity.
Bert: It’s not just fine. It’s a great cock.
Me: I’ve seen so many dicks. It’s fine.
It was a regular pink dick. I was much more interested in a large circular bump on his lower back about the size of a golf ball, but that wasn’t quite a conversation the moment called for. I sat on his chest while he touched himself and pretended to masturbate, hoping this would be enough for him to nut and fall asleep. It was clearly past his bedtime and I could see the two needs fighting each other within him: the one for sleep and the one for sex. Sex was winning out, but I knew he would crash after.
Him: Let me eat your pussy.
Me: No.
I giggled to lessen the blow of rejection. Out of the corner of my eye, I saw something moving. It was a jogger and her dog. They were embarking on a 4 a.m. lap. I dove off of the chaise lounge onto the ground.
Me: There’s a woman down there.
Bert’s little pale bottom was exposed as he laid on his round belly, trying to flatten himself down.
Bert: I don’t think she saw us.
Me: She’s looking this way!
Bert: Be quiet! She’ll hear you.
I watched her ponytail turn from one direction to the other. It looked like she was turned our way. Bert peeked his head up and watched as she and her dog jogged away.
Bert: Who takes their dog for a walk at 4 a.m.?
Me: Maybe she has to be at work by 6?
We resumed our positions. He was beating it quite rapidly, pausing every now and again. It seemed like he was edging, hoping I would provide a helping hand, but I had no interest in helping. He moved me off of his chest and onto the chaise lounge and continued beating off in front of me. I covered my pussy with both hands.
Me: You can’t come on me.
Him: Why not?
Me: I don’t want you to.
Him: Why not?
Me: I don’t want to have to clean come off of my body.
He resigned himself to my stiff parameters and kept his shirt handy. He came watching me and managed to cleanly catch it all in the shirt. Once that was done, I went inside to check on my sister. Bert stumbled inside, still naked with his shirt stuck to his limp dick. He went to the bathroom to wash off and I decided it was hot tub time. Jerry was reserved, yet clearly excited. He turned on the jets for us. Sofia and I got in and Bert slid in, half asleep and slumped into the corner beside me. Jerry reappeared naked with the slight shoulders and sturdy belly of an elderly man. His petite penis was almost entirely nested in his balls.
Me: Your house is so beautiful.
Bert: I told you.
Jerry: Thank you! It’s based on Bali architecture. I told them I wanted to be able to see the ocean from the hot tub, but of course, now you can’t because of the couch.
Me: Well, it’s lovely, regardless.
Sofia: Yeah, this place is beautiful.
Jerry, clearly pleased, embraced Sofia and pulled her in close while I massaged Bert’s head, trying to coax him to sleep. Bert’s eyelids fluttered. I looked up. What I had thought was an enclosed roof was actually entirely open to the sky.
Bert: Come cuddle with me for a while. Actually, you should just stay over.
Me: I can’t stay over. I have to take Sofia to work in the morning.
Bert: I have to be at a meeting by 7. We can go downstairs and sleep for a few hours and then you can be out with plenty of time to get home.
Me: I don’t wanna hit traffic.
Him: You don’t hit traffic.
Me: I won’t be able to sleep.
Bert: Why not?
Me: I have a whole night time ritual and I need melatonin.
Bert: Do you have any melatonin with you?
It was as if he was referring to melatonin as if it were some kind of party drug I kept on my person. Of course, I’m always rolling around with sleep aids. The other thing he seemed completely blind to was the fact that my face and hair were did. My makeup took half an hour to apply as did my careful hairstyle. I only managed to be so lovely due to a giant hairpiece which was actively giving me a headache. It was astounding to me that he thought I might actually become so comfortable lying besides him— a stranger who I have literally nothing in common with who actively repulses me— that I might fall asleep like a little perfectly painted cherub.
But, I’d only spent an hour, and I was curious about the downstairs, so I took a walk down the downstairs hall, observing Jerry’s photographs and book collection, as well as an erotic splatter art photograph decorated massage room. I cuddled with Bert for fifteen minutes before deciding it was time to leave. Wiggled out of the bed, even as Bert awoke and tried to pull me back under the covers. I walked upstairs and searched for Sofia. She was in Jerry’s room, and looked greatly relieved seeing me. Jerry walked us down, clearly disappointed by our departure.
Jerry: You sure you can’t stay the night?
It’s strange how lonely this question was. It wasn’t that these men had simply wanted to cream themselves, it was that they also wanted a hug after, and the hug after was equally, if not more important.
Me: I’m sure, but this was so much fun. Let’s do it again sometime. What’s your number?
I took down his number, because there is nothing more I’d love to do than take over his house one day.
Sofia and I left the house. She looked a bit stressed.
Sofia: Did you—?
Me: Yep. For both of us. It’s right here.
We got into my car and I counted out the other half of her payment. I’d made sure to hound Bert about it before he passed out. We both let out a sigh of relief. Handling outcalls is utterly nerve wracking. It’s like playing a game where someone else is making up the rules as you go. But we had made it and secured the bag.
Me: High-five?
We high-fived and I began driving us away.
Sofia: Did you see Jerry’s room?
Me: No, it was too dark to see anything.
Sofia: He had a picture of a naked black woman with an Afro hanging over his bed.
For a second I felt like I was in Get Out and we’d managed to escape, even if this detail was more hilarious than ominous.
Me: Of fucking course he did