A middle-aged man asked me to cum on his sleeping wife. He ran a Craigslist ad stating she was at rest and would one join him in a circle jerk. Shoot a fat rope then scatter. I figured this must be a fantasy for them both so chose to probe. I emailed my stats and said I was chill, that I’d cum then go with no drama.
He sent me shots of a topless woman “asleep” on a bed with no cover. Lights were on and she grinned in slumber. He said I could squeeze her tits with one hand as I worked myself with the other. Still, it felt strange. I decided I couldn’t go unless I knew for sure she knew. Didn’t know how to ask without spoiling their ruse.
I hemmed and hawed as it was late and they lived deep in the suburbs. I knew the spot to be trash and feared this might turn sketchy. As if the situation wasn’t suspect enough. At the same time I had someone else on the line from my own Craigslist ad. Hoped they’d come fuck me so I could be lazy. Shoot ropes then slip asleep.
Most nights like this I turned too drunk or tired, jacked off then went to bed. Didn’t possess the patience to play the game. Volley words with an internet ghost. After years of Craigslist hookups I knew what was worth my time and what wasn’t. Had lost a lot of the drive needed to chase sex with strangers.
I looked at the photo of the fake sleeping wife, thought of driving so far just to masturbate with an old man. His wrinkled dick and ashen balls. How I’d have to watch him cum. Hear his grunt. Smell his seed. I just wasn’t feeling it so said fuck it. Closed my computer. Shot wads and went to bed.
It reminded me of my first time in Austin. I ran my usual bevy of sex ads in hopes to stick my dick in a stranger. Have fun and connect with one who trawled the same alleys as me. These fleeting moments were some of the best highs of my life so I chased them often. I had little desire or mental energy for a relationship but needed my needs met with a dose of adventure.
A man rose from the muck. Responded to my ad saying his girlfriend would like me based on appearance and personality. That he wanted us to have a threesome. A spit roast gangbang. That she’d been interested in this act but wanted it to happen naturally. I saw her photos and wanted to fuck her. She was way too pretty for me. As for him, I didn’t care that we’d cum together.
He told me to bump into them in Zilker Park. Pretend I was a stranger. Charm them both into bed. It sounded like so much work with no guarantee. I thought of which tools lived in my getting laid kit. Excess charisma was not among them. Plus my skin was covered in bites from fire ants that made work of my neck. I looked a bit strange.
I decided to say fuck the dumb plan. Stopped emailing the man who wanted my goo in his gal. Instead of a threesome I jacked off in the trunk of my car. Slipped to sleep in that spot. No need to chase others when I could just fuck myself.
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