If All Else Fails - illustrated - Cover

If All Else Fails - illustrated

Copyright© 2023 by Authorwench

Chapter 8

True Sex Story: Chapter 8 - A fiction writer has a hard time coming up with a new story, and decides to do something radical. He tells the truth about his disturbing sexual experiences as a teen. Starts with a sci-fi soldier and includes brief scenes from several other genera, but most of the story is set in the US mid-west during the 1970's. Please check story tags to avoid unpleasant surprises.

Caution: This True Sex Story contains strong sexual content, including Ma/Fa   mt/ft   mt/Fa   ft/ft   Ma/mt   Coercion   Consensual   Drunk/Drugged   NonConsensual   Rape   Romantic   Gay   Lesbian   BiSexual   Heterosexual   Fiction   True Story   Crime   Science Fiction   Cheating   Sharing   Incest   Mother   Son   Brother   Sister   Cousins   BDSM   MaleDom   Humiliation   Spanking   Group Sex   Anal Sex   Exhibitionism   First   Facial   Masturbation   Oral Sex   Petting   Safe Sex   Voyeurism   Public Sex   Smoking   Prostitution   Violence  

My stepsister Miri and I were part-time whores. I’d spend a night with Mrs. Voss most weekends, and she gave Peanuts blowjobs about as often. She was right, we soon had enough for new bikes. We also pooled our money to get a bigger and much better TV for Christmas. Over time she bought herself a nicer bed and a desk, I bought a video game system, and I also saved enough for the down payment on my first car. Mom knew, and let us trade money for sex, since we gave her some of our ill-gotten loot.

Miri and I visited Lauren’s place for beers and oral threesomes occasionally. I pestered a few times, but Lauren never wanted to fuck me for real. She had a great body, but was kind of ugly and not very smart. We also struggled with the fact that our girlfriend often sucked off her grandfather, and three other guys!

Sometimes when we were horny, Miri and I would give each other oral at home, but only when Mom was away or blacked out drunk. I asked to screw her a few times, but Miri wanted to stay a virgin a while.


One night after her ‘friend’ Jim left, Mom passed out in the living room, naked on the couch! She faced the wall, with her back exposed, and I could see pubic hair and her anus between her thighs! Her butthole was strangely shiny. I realized it was some kind of lube. There was a used condom on the floor, and a fifty-dollar bill on the coffee table.

I tried to shake her awake and shouted a few times. She didn’t react at all. I stared at her very large boob a while. I was horny and Miri was in her room. I was a very naughty boy, and played with my mother’s breast! I felt her nipple, squeezed the soft fatty flesh, and even sucked it a little! I called out, “Hey, Miri!” She didn’t react either, so I assumed my sister was asleep.

I stared at my naked mother, with a mind full of dirty thoughts. I finally had a chance to screw a woman under forty! Better than sex, I had the wonderful opportunity to do anal with a woman!

I pushed through my guilt, squeezing Mom’s huge boob and rubbing my cock though my pants. I touched her butt and moved my finger around the rim of her anus. I sniffed my finger and was oddly aroused by the filthy smell of shit, female body odor, and KY.

I shook her again, loudly saying, “Mom! Wake up!” She didn’t move, other than her quiet snores. I smiled and tried to control my excitement. I dropped my pants and boxers to the carpet, then remembered how important condoms and lubrication was for anal.

I got the big jar of Vaseline from Mom’s room. I smeared a little around her hairy and wrinkled pink rosebud, once I rolled on a condom. I dipped out another blob with my finger, and pushed it into her tight little hole. I wanted to buttfuck her, not hurt her.

I was excited, aroused, and very nervous. I listened intently for any hint of Miri or visitors, as I slowly slid a finger into her pooper and moved it around. I slid it in as deeply as I could, then pulled out and inserted two fingers. I moved them around some more and could eventually get three inside.

By then I was stiff as stone. I pulled out my fingers and laid on the couch behind her, then slowly inserted myself. I was pushing my pecker into my mother’s ass! I was poo-pounding my mom! So filthy! So evil and nasty! I reached a hand around her to feel her pussy and liked her lush, thick pubic hair in my hand. I rubbed her pussy lips as I pulled out and pushed back into her turd hole. GAWD, it felt so GOOD, but so filthy!

I worried when Mom started mumbling. “Uhh. Yeah, Jim. Ummm!” She was incoherent so I kept going, thrusting over and over, in and out, stuffing her plump and curvy butt. I moved my hand from her pussy to her big tit and squeezed while I pumped her asshole.

I felt the condom break, but the excitement was too much! I went over the edge, spraying sperm deep into my mother’s colon! I bit my lip, trying to stay quiet, as I kept humping into her a little while. I rested a hand between her massive melons, then quickly dozed off, still inserted.

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