Anal Insertion Stories

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Massage What?

by MightyCasey on Sep 19, 2017
How To

How to initiate prostate massage into your relationship. This is what worked for me without a large amount of ass-pain, pardon my pun. I'm not obsessed with my prostate or anything, but it's nice to have a wife doesn't mind giving me an occasional prostate massage. My wife of twenty five years Gwendolyn is a real cutie, she has always been a great lover...

Barbara's First Gang Bang Ch. 02

by eroticwriter28 on Sep 13, 2017
Group Sex

Barbara's journey into complete submission continues. Standing naked and bound spread eagled, Barbara's mind began rippling into a submissive headspace as the six men who surrounded her continued to fondle her body and the others stood with their drinks in hand, watching with rapt attention. The man who had been squeezing and kneading Barbara's right brea...

Seduction Ch. 09

by neolithic_one on Sep 16, 2017
Mature

As I waited for Dr Edward’s to begin his examination I wondered why it was necessary for me to be strapped to this apparatus, but once again not being familiar with medical matters I concluded that the Doctor would not be doing anything that was not proper, after all he was a professional man. Nurse Jones had moved behind me with the video camera and I watc...

Anal Adventures of Alex Ch. 02

by Goldeniangel on Sep 12, 2017
Anal

Over the period of a couple weeks, Alex got a little bored with fingering his ass while he jerked off... although it still felt good, it was often lacking that feeling of a painfully pleasurable stretch. If he left his ass alone for a couple of days then it would tighten up again, but in lieu of having anyone else's ass to plunder he enjoyed being able to pl...

Cathy and I Get Caught

by RiteofSpring on Sep 15, 2017
Anal

It all began with an innocent drink. Cathy and I teach together at a local school. I confess I liked her ass as she swayed down the hall on the way to class. She's short, a bit dumpy really, with short brown hair streaked with blonde, but I loved that ass. I really wanted to see the other side of that ass, her brown cunt between her thick thighs. One day,...

Anal Exploration - Violet 02

by OutlawedSubversion on Sep 26, 2017
Anal

A week had passed since her first exploration into the intricate pleasures of anal sex. Since that seminal introductory evening, they had enjoyed the sensations on two more occasions. The first took place a mere few hours after her initial penetration. On rousing from her slumber, her body still warmly nestled into his, she rose to a seated position on t...

Joan Takes Charge Ch. 04

by cynthiablaine7 on Aug 12, 2019
Fetish

[This story is part of a series, and you likely will enjoy it more if you read the earlier chapters. However, that is not mandatory, but it does involve incest, bodily functions and spanking, as well as other fetishes. If any of this offends you, please read no further. All characters are 18 or older.] ***** Joan thought about the episode with her brother...

Admitted Pt. 01

by Katalanta on Mar 3, 2020
Fetish

Cora wasn't totally sure when it would happen or what the scene would consist of as she had given Owen permission to surprise her. Well, it was more like she had asked him to surprise her. The word "please" had been used more than once. "You promise to use our safe word if you need to?" Owen asked after she was done explaining what she had in mind. "Yes....

Sodom-me, Sodom-you

by rockinroscoe on Sep 12, 2017
Anal

It all started when I was shaving your pussy. I had finished and was giving your pus the tongue lashing it deserved. I thought to myself while I'm down here I might as well see what other adventures I can have. While strumming you clit with my tongue I pumped 2 fingers in and out of your pussy. I pulled my middle finger out of your pussy and gently laid it a...

Eve Visit's Louise Bellman's Clinic Ch. 02

by eved65 on Aug 18, 2017
Fetish

"Eve, that was incredible" I heard through a distant fog. The voice was Louise talking to me. I had just peed my panties and masturbated myself to a tremendous orgasm in front of her and William, the therapy assistant. "I've never seen anyone so stimulated from a debasing act. There's no doubt that you are a piss slut, but we'll need to expand your degradati...