Anal Insertion Stories

48,203 results
Orientation
Length
Source
Infinite Scroll

Tampon Training for TG Women

by slutty_jannelle on Sep 1, 2017
How To

'...a lady in the drawing room, a whore in the bedroom.' Copyright, 2007, by jR Contents are for entertainment purposes only. The author assumes no responsibility or liability for its use or abuse. * For me, and I suspect, most TG 'girls', the anus becomes our 'pussy.' Curiosity and a desire for the total female experience naturally led me to explore 'f...

Return to "Weekend School" Ch. 14

by cynthiablaine7 on Oct 26, 2020
Transgender & Crossdressers

[This story involves bodily functions and sometimes severe disciplining, including caning and spanking, as well as crossdressing. If reading about those offends you, read no further. These stories may be read separately but do gain from being read in sequence.] Laura Franklin wasn't sure what kind of response she would receive when she sent out notices by m...

Tangled Web

by redsweater on Sep 16, 2017
Transsexuals & Crossdressers

One fateful day I met a girl that changed my life forever. She was especially good looking that day in fact, with nice long legs, well toned curves, long dark hair, and pouty red lips. I never would have known. I struck up a conversation with her, as the PUAs taught me to, and before long we were sitting down alone at a table with coffee and snacks. We talke...

Short Ride

by GDeloney on Sep 11, 2017
Toys & Masturbation

The trip started off exactly as I planned. We loaded up the Tahoe with all of the hiking gear that we had accumulated over the past two years. Mainly the hiking stuff belonged to me, tents stoves, water purifiers. We had purchased a sleeping bag and a backpack for her. This was going to be our first trip into the unknown for multiple days. We planned a trip...

Daydream?

by Karmacouple on Jun 19, 2019
Anal

Straight from the shower her warm body was begging for release. A smile passes her lips as she thinks of the lotion she had placed back in the shower. Wishing longingly, it was used as it had been before, but closing her eyes and reliving the full anal insertion of her own fist. Nowhere near the knee buckling pleasure brought by the love of her life. But a...

The Worst Chain Story Ever Ch. 11

by Joseki Ko on Sep 11, 2017
Chain Stories

Note to Readers: Please read the title. This is meant to be bad, repetitive and boring in places. If it were not a Chain Story it would be categorized as Humor and Satire. You have been warned. Continue at your own risk. It was the best of times it was the worst of times. John (the Dong) Shaw had been off of work for a week. The episode with the dildo had b...

Entering Lynda's Asshole

by 46204_zipper on Feb 26, 2019
Anal

I could taste an exciting blend of scented soap and Lynda as I wiggled the tip of my tongue in her asshole. A clean asshole is a wonderful thing to tongue. I know it is called "rimming", but I don't "rim". I tongue fuck. As I moved in and out, Lynda began to wiggle her butt. I dragged the flat of my tongue up and down her crack and penetrated her asshole a c...

Barbara Ch. 12

by NiteWriter on Sep 13, 2017
Novels and Novellas

Chapter 12: The Pool Hall Gangbang (pt2) This is intended for adults 21 and over only. If you are offended by graphic descriptions of a sexual nature, please, don't read this or download it. If this is illegal where ever you are reading this stop now. * * * * * Barbara had cum just about everywhere on her. Her cunt was seeping with sperm, her asshole was...

Cautious Smiles Ch. 03

by xiola-blue on Sep 14, 2017
Anal

"Bend over," Alex said forcefully as he moved toward the nightstand. Fumbling around for several moments he found what he was looking for; a new bottle of lubricant. Chloe's eyes were wide with anticipation. She grinned when she saw the bottle in Alex's hand. "I'm already soaked," she coaxed. "No more talking," Alex commanded as he knelt behind her on the...

Phallic Imitation

by scarlet_letter87 on Sep 17, 2017
BDSM

I'd been seeing Perry for a few months, or at least we'd been hanging out and fucking a lot. He expanded my world in a multitude of ways. He introduced me to CBT, which I've now grown rather fond of and have been looking for new players. He let me play with his ass and explore in ways that no one had ever allowed me to. We'd had threesomes, both of a MFF and...