Chapter 2: The Voyeur

Not to spoil anything, but I only sold, or rented out, my body for about a year. The shame that I felt and the fear I had of being arrested and losing my job were too much to deal with. Most of my clients during that time were okay, mostly middle-age and older men who I think were more lonely than horny. There were a few that seemed to want a quick orgasm, so they would have time to talk to me for the rest of the hour they had paid for. Maybe being a teacher made me a good listener. Most of my ‘adventures’ during that time aren’t worth mentioning, but there were a few unusual or just plain weird times that I’d like to tell you about.

The first one happened one Saturday afternoon. It was my first “matinee”, a 2:00 p.m. session. It was also the first time I was meeting a john, not in a nice hotel or his residence, but at a motel. As motels go, it wasn’t bad, and of course, Naomi had checked it out. Still, I was uneasy, having seen several prostitution busts on the news in locations like that.

I parked as far from the front office as I could, and even though I was dressed like a typical tourist —shorts, a nice blouse, and sandals —my paranoia about anyone seeing me and knowing why I was there still haunted me. The room was on the second floor of the two-story building. I walked up the stairs and stood in front of the door. I double-checked the room number because knocking on the wrong door was another fear.

I looked around and didn’t see anyone watching me, so I gathered my courage and knocked. There was no answer for a few seconds, and I almost decided to leave. I knocked a second time and waited. I was about to go back to my car and call the contact number when the door finally opened. My client’s name was Eddie. It was a relief to see that he was handsome. I wasn’t used to that. He appeared to be in his mid-thirties, and based on how his biceps filled the sleeves of his polo shirt, he worked out regularly. My first instinct was to question why a man like him needed to hire an escort. He looked like he could walk into any bar, or maybe just take a stroll down the busiest tourist street in town, and he would attract women who would be glad to do him just because of how he looked. Then I reminded myself not to overthink things. There was nothing forbidden about my having sex with an attractive partner and getting paid for it. Maybe this was karma for some of the less attractive johns I had serviced.

After Eddie opened the door, he said, “Hello, Kitty. Come on in.”

When I walked into the room, I noticed a man sitting in the corner. My first thought was that they were vice detectives, and my greatest fear had come true. “Wait,” I said, “I don’t do doubles.”

“Relax, hon, that’s my buddy Siggy. He’s only going to watch.”

“Hi,” Siggy said quietly, as he gave me a shy wave.

“She’s a cutie, right, Sig?” Eddie said.

“A natural beauty, not too much makeup. I like that.” Siggy confirmed.

I still figured I should charge more for a voyeur, but this situation had never come up in my discussions with Naomi or Sarah. I decided to take care of business and try to forget the weird dude watching us.

I turned my attention back to Eddie. He put his strong arms around me, and we kissed. Even his kiss was nicer than I was used to. He must have just brushed his teeth with minty toothpaste. Next, he lifted me and threw me on the bed. It wasn’t as violent as that sounds; it was more like kids fooling around. It reminded me of when my big brother used to toss me around when we were kids. I giggled a little, and Eddie smiled down at me.

He quickly stripped, and I saw that the rest of his body was as impressive as his arms. When his boxers came off, I was almost afraid to check out his manhood. I was scared that such an Adonis might have a huge dick like my first client, but when I looked, I saw that at least in that area he was a normal dude.

I pushed my shorts down - no panties, why bother? My top came off next. I heard a groan and looked over to Siggy. He hadn’t wasted any time. He already had his dick out and was stroking it. That’s when I noticed that he was in a wheelchair. Whatever accident or illness had put him in that chair didn’t keep him from having an erection. I began to understand a little more about why he was “just watching”. It looked like watching and masturbating might be all he could do.

I expected Eddie to join me on the bed, but instead, he grabbed my wrist and yanked me back to my feet. “This is for Siggy,” he said, as he lifted me up and somehow managed to rotate my body so I suddenly found myself held by him with my head just a couple of feet off the floor. If Eddie dropped me, it would have been bad, but his grip was strong. It took me a few seconds to figure out what he wanted me to do. I noticed that my face was level with his cock, so, like a good little escort, I put it in my mouth. At the same time, and again without even thinking about it, I wrapped my legs around his head and pressed my mound against his face.

I didn’t have to do anything except hold Eddie’s manhood in my warm mouth to get him fully erect, while his tongue was teasing my pussy. I remembered seeing a scene like this in a porn vid once, and wondered then what it would be like. Now I knew - it wasn’t comfortable at all. I still felt uneasy about my head dangling down toward what looked like a very thin carpet. Fortunately, I think Eddie was growing tired also, because he spun me around and put me back on my feet a few seconds later.

I was a little wobbly, both from being upside down and from how fast he spun me around, so I sat down on the bed. Eddie stepped up close to me and held his cock like he was aiming it at me. I took the hint and slipped my lips back over the business end. He held my head and started face-fucking me. That’s not something I’m not fond of, but again, it’s part of the business. As long as I don’t gag or throw up, I can put up with it.

I looked up and saw that he was looking over at Siggy, so I figured this was still part of what his friend wanted to see. Eddie and I apparently were just characters in his fantasy. I had learned that a lot of johns just wanted to live out their dreams when they used an escort. Some of the other girls I had talked with told me that role-playing was a lucrative addition to their usual suck-and-fuck clients.

“Fuck her,” Siggy said, the first time I had heard from him since our quick introduction.

Eddie backed up a little and motioned for me to move to the center of the bed. Before I did that, I went to my purse and got out a condom. Never leave home without them was my rule. I wasn’t worried about getting pregnant, but when you’re having sex with men who frequent prostitutes, ‘for the prevention of disease’ is important.

After I rolled the slippery rubber over Eddie’s cock and made myself comfortable, he crawled on top of me and tried to insert his Tab A in my Slot B with no further foreplay. Eddie’s brief licking while I was upside down hadn’t properly prepared me for penetration, but the lube on the condom saved me from too much discomfort.

Eddie started moving, and it almost seemed like he was the one getting paid for sex. He seemed disinterested in me or my body. I think he would have been just as happy with one of the Japanese sex dolls I had seen online. For some reason, I found myself worrying about the show we were putting on for Siggy, so I started moaning and sighing, and talking dirty to Eddie. “Ohh, babe, do me harder ... yes ... that’s it ... deeper now ... am I tight enough for you?” My comments may have been directed at Eddie, but were for Siggy’s enjoyment.