Earlier this year, I wrote a book about my miserable sexual experiences. In it, I detailed why sex with willing partners is all but out of reach for me, along with what this does to me. Unsurprisingly, this isn’t a book anyone wants to read. I’ve decided to post some salvageable pieces of it on this blog. Below is a retelling of a clumsy night with an escort. My grandmother had died earlier that day.
From Chapter 1:
I led her to the bedroom and we dealt with money. I paid for the hour and gave her the tip upfront. She seemed content, even pleased with what I offered. Tipping well was important to me. I didn’t just want better service. I wanted these women to know I appreciated what they were doing for me. I doubted any of them realized how important it was.
“So, you want me to get undressed?” she asked, already taking down a strap of her dress.
“Yeah, let’s get started.”
This was procedural, almost formal. We sat on the bed next to one another and stripped to our underwear without touching each other. Her phone rang while we stripped. She took the call. I didn’t protest. The call was brief and soon we started touching. We didn’t discuss what I liked or what her limits were. She simply leaned in and started kissing my neck. While sitting up together, I rubbed her sides and caressed her back. She didn’t respond to me doing either. We ended up with me on my back and her straddling my crotch. She took off her bra, tossed it to the floor, and massaged my chest. I kept attempting to touch her, but that felt like a distraction from her procedure.
“You like this?” were her first words since taking that call.
“Of course,” I said, watching her kiss my stomach.
She began kneading my crotch and then sliding her pussy over it with her panties on. While doing so, she took on a slightly puzzled look. Apparently, she noticed something I hadn’t noticed.
“Did you do something else tonight?” she asked.
“What do you mean?” I replied, genuinely confused.
“You’re not getting there,” she said.
She was right. I wasn’t getting particularly hard. Given what she was doing, I should’ve had a solid erection. I remembered I’d jerked off earlier in the day. Whenever I hired an escort, I tried to rub one out a few hours beforehand to keep from ejaculating too quickly on the clock. That must’ve been it. I told her what I had done. She sighed and rolled her eyes. I hadn’t paid for attitude, but I kept quiet.
“Try puling it out and using your hand,” I suggested.
I felt like a scumbag telling her what to do, and considered offering to get myself up for her. Assuming that might be insulting, I stayed quiet and let her do her thing. She stroked me, used some spit, and sucked me for a few short minutes. I got hard enough and she grabbed a condom from her bag without even asking if I wanted to fuck. Her phone rang again while she was putting it on me.
I tugged myself through the sheath to make sure I stayed hard while she talked. The second call annoyed me, especially as I realized she had a free hand. My desire for pleasant, stress-free sex kept me from saying anything, but her behavior was irritating. I’d paid for this and she was ignoring me.
The call ended and she took off her panties. They were lacy and frilly and would be on someone else’s floor later in the evening. I could tell she had to shave her pussy often. Stubble and razor bumps covered her crotch. She sat on my cock and started to ride me. Again, procedural. After just a few bounces, her phone rang a third time. In a display of courtesy, she merely craned her neck to see who it was. I tried to remain into what was happening, but I really wanted to stop. This wasn’t the encounter I’d craved. I could sense my family watching me have lifeless sex with a bored, distracted prostitute so soon after my grandmother’s demise.
The condom deprived me of whatever enjoyment I would’ve felt. While she fucked me, I couldn’t tell if I was still hard. Most of the time, I had to focus to keeping from coming. This time, I had to focus on trying to come. I pictured a coworker I’d been thinking about lately when I jerked off. I thought about a neighbor I’d seen sunbathing in a two-piece. I struggled to find that one fantasy that would bring it out of me. Then the rush hit me abruptly. In an out of character moment for me, I let myself come in the condom while still inside her. I cried out, but didn’t tell her explicitly. At first she seemed bothered, but I could tell she was relieved to be finished. She got off of me and didn’t even look at me while gathering her clothing. With her back turned, she asked me where the bathroom was.
I tossed the condom in the trash without tying it. Standing up, I started to wipe off. Through the bathroom door I could hear her talking on her phone to whomever. She stayed in there long after she had ended her conversation and much longer than I’d expected, and long after she had ended her conversation. I got close to the door to check on her, and I could hear her mumbling. She sounded like she was chanting. I backed away and asked if she was okay. Moments later, the door flung open like she’d been having some kind of difficulty with it. She dropped her bag and cursed at the mess on the floor. I looked down and noticed the rosary.