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Strap-on Sex Stories

This section features stories that involve sexual activity with a “strap-on”—a dildo attached to a strap or harness.

Although typically fastened around the waist and used as a substitute for a penis, strap-ons can also be used to enable double penetration, or they can be fastened to a lover's face to create an intimate penetrating experience. They come in many shapes, sizes and colours, and some even vibrate!

Strap-ons are commonly used to perform anal sex on a man (known as “pegging”), but there are countless other possibilities, and authors might draw inspiration from other categories such as Lesbian, Threesomes and Trans. The only limit is the imagination of the author.

The Cupid's Arrow Challenge

A viral Valentine's Day love spell backfires

Evan knew what he was doing was wrong. He knew it while he was rolling up the rose petals in the cigarette wrapper and twisting one end into a point. He knew it while he was trimming the dove feathers and attaching them to the sides for aerodynamic stabil...

Hurricane Ride - Part 1

When The Universe Offers You A Wild Ride, Take It

Betsy had one hand on his hips and was fucking his asshole with her strap-on. She was a tall big-titted Southern blond. Her friend, Mary Lynn, a brunette and just as well endowed was face down at the restaurant's table before him. Bob was fucking her assh...

Christine Gets Her Man

A wife's infatuation must be explored.

“Christine, what on earth are you watching?” Ben asked. Christine slammed the cover of her laptop down. Ben tried to grab for it but she pulled it closer to her body. Ben pleaded, “C'mon honey show me, it looked naughty.” Christine replied, “No, you will...

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22.9k Views 22.9k
2.7k words 2.7k words

Anne Takes Control

Discovers she likes to give as much as receiving.

I arrived home with the brown paper bundle under my arm, sneaking into the house. The coast was clear, so I ran upstairs to our bedroom, to our hiding spot, behind our luggage. I threw the bag behind the suitcase, and threw over some jeans to cover it all...

RedDemoness

The Bunny

A young woman takes advantage of her "innocent" lover

The veiny, black dildo protruding lewdly from my strap-on stretched her pussy impossibly tight. I swore it would tear at any moment—her lips rolling in and out with every thrust and withdrawal. But that did not stop me from violently battering her foolish...

Good Girl

Smoking is indispensable if one has nothing to kiss ― Sigmund Freud

With her mistress outside, she’s an obedient subby-mannequin. Motionless, except those pretty obsidian eyes are peeking across the crowded room. Her blush is vivid; she realizes I’m staring. Being recklessly dissolute, I lick my lips when she peeps again....

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Our Anal Afternoon

Our day started with thoughts of anal fun and brought us our best orgasms yet.

Annette and I met later in life and were married at the age of forty.  From the very beginning, we enjoyed a healthy sex life by trying new things.  We weren't interested in adding others to our lovemaking but had become more interested in anal of late.  ...

Strap In, Hold Tight (It Can't Be Right - Pt1, Ch 9)

The end of Nicola's story about her night with Steph and Alex

All the focus, it seemed, at home and work, was on summer celebrations, with all of the talk and questions from Jake and now the reminder from Nicola about her plans. I did enjoy them, maybe I was a stick in the mud though, because I felt they and the Chr...

The Girls Play With The Big Fake Dick

Paige and Robin have desires that lead to them having fun together.

“Holy fuck, Paige! You said it was big, but goddamn, it feels like you are splitting me open,” cried out Robin. As Paige continued to push forward, driving the fake dick into Robin, she replied with, “Oh, shut the fuck up. You let Jake take your virginity...

Family Affair Strap-on: Part 3

Story of strap-on sex leading to marriage.

Being open-minded in life just about life in general, can also be about being open-minded sexually. This is what the relationship between Jean, Daphne, and myself had become, a very open sexual relationship of sorts. Now I had two women strap-on fucking m...

Family Affair Strap-On: Part 2

Strap-on sex with sister-in-law and her daughter

I was helping Jean and Daphne with some financial assistance. My deceased wife Louise and I were already helping Jean and Daphne with some help before Louise passed away. Jean never did ask for anything at all from me other than just love and sex. She did...