Ruin Stories

22,222 results
Orientation
Length
Source
Infinite Scroll

Be A Good Girl Ch. 03

by angeline_dc on Sep 17, 2017
BDSM

Chapter 03: The Road to Ruin The ride to the restaurant is an ordeal. You try two or three times to initiate conversation, but I don't bite. I've never been anything but wide eyed and thrilled to be near you – everything fun, everything light, everything you say charming and funny. So my silent treatment comes across as deadly serious. A challenge to our or...

Webslut Madison Ch. 07

by Rockwellray0 on Sep 26, 2017
Exhibitionist & Voyeur

It had been a little over a month since Madison played the dice game. At first, it was exciting to her to be exposed as she had been. Over time, though, Madison found that she was no longer getting a rush out of just having her pictures posted on the web site. She remembered how it felt to roll those dice - the rush she got, the adrenaline, the pounding ches...

Lovers in the Wild

by goldenmyst on Sep 14, 2017
Erotic Horror

He drove me in his convertible, the top pulled down and the wind rushing over my ears. We drove north then west to Abique. We passed over a dam by a clear blue lake and onto the side of a barren red pyramid-shaped mountain, a thousand feet tall. The red color of the mountain was so rich and vivid that it seemed to glow in the afternoon desert light. After p...

Pegged by Ex-wife

by Sjen451 on Oct 7, 2019
Fetish

I received a text out of the blue from my ex wife. It simply read "I WANT TO FUCK YOU". I didn't know what to think. But my cock instantly got hard and I knew I had to agree. I invited her to my house. She wasted no time. She knows where I keep all my dildos in the closet. She went straight for my largest one (12 inch hard rubber black cock too girthy fo...

Ally's Letter to Jack

by Anal_Ally on Sep 15, 2017
Letters & Transcripts

Dear Jack, It was really difficult for me to post this letter on 'Literotica' knowing how publicly humiliated I might be, but I have done it out of my devotion to you. I know you won't care either; I mean most women get flowers or chocolates when their ex turns up on their doorstep after ten years. What did I get; you hammering on my door at six in the mo...

Ariana Grande Possessed For Revenge

by Theninjagamer308 on Jun 2, 2020
Mature

(Just for the record I know Ariana loves her fan’s. I just did it for the purpose of this story) Your name was Roy, and you were so excited to meet Ariana Grande. You meet her backstage, and said hi. Ariana gave you an annoyed look, and started to walk away. You follow her she turns around. “Now look I’m not going to tell you this again beat it I’ve had a ru...

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Rich Bitch

by Jamie_in_dresses on Sep 18, 2017
Transsexuals & Crossdressers

I had to work out of town for a few days several times a year and used this time alone to experiment with my longtime fantasy, Cross-dressing. In the last couple of years I have frequently been working in a town where my wife's very rich friend lives and she offered to let me stay with she and her husband. This produced a complication because I was no longer...

Denial Slut Learns to Cuck Ch. 05

by THEGINGERSLUT on Jan 28, 2019
BDSM

I couldn't believe what I was hearing. We were going to play? Out? In public? The three of us? Sir must really have lost it for real this time. "Is there something wrong, love?" he asked with mock concern. I giggled and collapsed into his arms. He was such a bad actor. "Stop thinking and just put the damn thing on and meet me at the restaurant straight after...

Ghost Hubby Haunting Ch. 02

by SEVERUSMAX on Sep 13, 2017
Erotic Horror

When Marla got back from the bathroom and bandaged the tears in Andrea's ass, Alexander suddenly entered her. Picking up the vibrator again, he shoved it brutally up Cherry's butt, making her squeal. While he did this, he stuck two fingers inside Michelle's cunt, as if it to say that she wasn't off the hook yet. "Get out of me!" Marla demanded in her head...

Webslut Madison Ch. 08

by Rockwellray0 on Jul 2, 2018
Exhibitionist & Voyeur

It was a good thing Madison picked a Saturday to completely lose control of her desires and make the video and take the pictures that could potentially ruin her. Not that she really chose the day, but it turned out to be a good thing that it happened on that day of the week. After all, once she clicked "send" she more or less paced around her apartment half...