Anal Dilation Stories

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Never Have I Ever

by CaffeineFetish on Sep 16, 2017
First Time

Going out to lunch with an ex has historically been a very surreal experience. Do you shake hands or hug? God forbid you both do the opposite of the other and conduct a weird desynchronized dance of handshake half hug. Callie and I ended on good enough of terms, so we hug and sit across from each other, some slight awkwardness due to her half leaning in for...

Fantasy For My Internet Lover

by PRPrincessa268 on Sep 11, 2017
Exhibitionist & Voyeur

I have a fantasy of having sex in a movie theater with everyone either watching or hearing me have an orgasm. I would like to someday have oral sex and then be assfucked in a theater in hearing and viewing sight of all the attendees but never actually being spotted or caught. The thought of all those faceless, nameless people listening to me and seeing me ge...

Two At A Time

by GentleGeorge on Sep 14, 2017
Group Sex

Sara woke up suddenly early in the morning. That was quite a dream, she thought. Yes, there was a solution to meeting her New Year's Day resolution. This weekend, she would put her plans into action. ********** Sara worked at a large medical clinic in the administrative areas. She had heard the doctors talking about their undergraduate years at the nearby...

Alison Gives It Up To The Wrong Man

by User666 on Aug 30, 2017
First Time

Carl pulled into the parking space, the reserved spot just outside her apartment door and reached over to her. She moved toward him and he quickly invaded her open mouth with his tongue. After months of dating, he was determined to get into her pants. She had stoutly resisted his best efforts but tonight, either here in the car or in her bed; this was going...

The Unseen Gift

by Babeslady on Sep 13, 2017
Erotic Couplings

Gemma laid out the toys on the table of the hotel room; feather ticklers, massage oil, a whip, an anal vibe, lube and condoms. She checked the clock on the bedside table. Still about 10 minutes until she had to leave. The nerves were starting to kick in now as the scenario she had been thinking about for so long was about to become reality. Her husband...

Babysitter No More Pt. 03

by adler666 on Dec 2, 2019
Erotic Couplings

Part III: New Paths for All, A Public Couple ************* A short multi-part story of how a man meets a figure from his past and how it impacts every aspect of his life. Part III finishes the story. ********* One PM couldn't come quick enough. I decided to drive over to her place, not giving her a chance to reconsider after last night. I was nervous and...

Family are Friends Forever

by silverfox_granny on Dec 25, 2019
Illustrated

My name is Paul Drake; my wife of twenty four years is Nancy. We've come upon hard times faster than we'd ever have thought. I lost my job six months ago. Nancy had worked at the local saving and loan for nine years and we thought that plus our saving would carry us through the hard times until I could find a job or times would get better. No so. Nancy los...

Woodland Walk - New Opportunities Ch. 03

by ambise on Dec 2, 2019
Group Sex

Jill's thoughts drifted back to the events of the past weekend, Sunday had been a bit of a washout as she had been exhausted by the Woodland walk, she smiled remembering being surprised at her enjoyment of being forcibly taken and becoming submissive. Steve, she recalled, had obviously enjoyed himself, he had royally screwed her immediately on their return h...

Surprise Pt. 02

by CuriousCouple24 on Jan 27, 2020
Erotic Couplings

Marie didn't budge when the massage therapist walked into the room. "My name is Gary," he began before realizing that his client was dead to the world. He had left clients like this after a massage but has never started a session this way. Gary chuckled to himself and checked the details on the appointment. If the client was awake, he was to proceed with wha...

Under Mommy's Direction Ch. 05

by MommysHypnoSissy on Apr 13, 2020
Transgender & Crossdressers

The rest of Jaime's day had been a whirlwind of tasks and chores to complete before his Mother got home. His online Sissy Trainer, who demanded that he refer to her as 'Mommy', had given him a myriad of tasks. First it was cleaning up his Mother's bed and sexy toys, putting everything back how he had found it. Then it was back to his room to dispose of his b...