More from Chapter 7 of Aching: Memoirs of an Unrequited Sex Addict

Here is the rest of the piece I posted Monday about a discouraging session with an expensive prostitute.

From Chapter 7:

“What do you like to do with your sessions?” she asked.

“I like to relax,” I answered. “Feel good. I’ve never been to this place, so I don’t know what to expect.”

“What were you expecting?” she asked, seeming interested for the first time.

I’d just told her I didn’t know what to expect, so I wasn’t certain how to answer her. I decided to go with what I wanted.

“To have sex with you,” I said candidly.

She sat up, covering slightly with one of the pillows.

“Are you a cop?” she asked.

“Um, no,” I answered, sensing all might be lost. Her expression and posture told me this was a legitimate question. “No, definitely not.”

She leered at me for a moment, but seemed convinced. I got the feeling this wasn’t something she always asked. She asked because she had smelled something on me. The formality in my voice. The lack of relatable feeling. The distance. The awkward eagerness. My clumsiness made her wonder if I was part of a sting, which I could understand being a real concern. I wasn’t a cop. I was just some weird, desperate guy willing to pay hundreds of dollars for an hour of artificial intimacy. She chose to tolerate me for money when others wouldn’t for free.

The proceedings ended up being unremarkable. What could top her asking me if I was a cop? I realized a guy leads a charmed life if a prostitute pegs him for a plain-clothes detective. I was that guy.

Asriel undressed and looked delicious even while appearing apprehensive. Precious freckles dotted her back. More were sprinkled across her expensively augmented breasts. I hadn’t realized she had implants from her picture. Maybe it was taken pre-surgery. Instead of contemplating this, I undressed with her. I doubt she was as impressed with my physique.

From there, we went through the motions. She massaged me while I was on my back. I rolled over. She tugged my cock, but put a condom on me before blowing me. I wondered if that was standard procedure, or just for guys she didn’t like. She climbed on top, sat down on me, and rode me slowly and robotically in perfect silence. Her face remained stoic throughout. I should’ve given her a bigger tip.

Because I didn’t come right away, I got the chance to get behind her. This probably had more to do with her being tired or not wanting to look at me than with making me happy. I slid inside her, taking advantage of the view. Her frame was just too perfect. I wanted to lick her from behind, but I didn’t even ask. I went ahead with fucking her the best I could. As usual, I was preoccupied with competing fears of coming too soon and not pleasing my partner. She didn’t make the noises I’d hoped for. Rather than moaning, I heard her give a tiny “Ouch!” When I asked what was wrong, she said her knees hurt in that position. We switched to missionary. I could feel myself losing my erection in the condom. As had happened before, I couldn’t tell if I was hard while fucking. Here I was with this incredible woman, and I had to use another fantasy and concentrate with all my focus to make myself come. We were both glad when I did, but for different reasons.

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