Gaping Hole Stories

122,731 results
Orientation
Length
Source
Infinite Scroll

Candy Holes Ch. 03

by MTL17 on Sep 11, 2017
Celebrities & Fan Fiction

Author's note: To be different I decided to bounce back and forward in time with this story. ***** Candice Michelle smiled widely as she saw the name on her phone. It was ironic because she had been just going through her contact list and found herself lingering on the very name that was now flashing, although that was only partly why Candice was now smil...

Last Friday: First Sissy Experience

by sissysyzygy on Mar 5, 2018
Transsexuals & Crossdressers

Been a lurker for a little while, and thought it was time I contributed with a post! *** Title: Last Friday "You ready for your surprise?" she asked me coyly. "Yes!" I said excitedly, thinking of the possible toys we had been looking at online, or perhaps a striptease. We had our eye on a Bad Dragon dildo as our starter strapon kit had grown my interest...

Assmacher

by MTL17 on Sep 17, 2017
Celebrities & Fan Fiction

Brooke Tessmacher was more nervous than she'd ever been in her life. So nervous she almost stayed home, almost sent a text with some lame excuse to explain her absence, almost chickened out when she reached her destination, when she found herself facing the door to the apartment of the TNA Knockout simply known as Tara. It took a lot for her to knock on that...

Look How Far We've Come

by MTL17 on Sep 13, 2017
Celebrities & Fan Fiction

I know we've had some small issues in the past @KaitlynWWE , but I'm so happy for you. Look how far we've come. #chickbusters4life Kaitlyn frowned and turned to the girl sitting next to her, who of course had that huge grin on her face which Kaitlyn struggled to stay mad at. Not that she didn't try her best, "You are so going to get me fired." It was now...

Christine's Special Room Ch. 02

by NiteWriter on Sep 12, 2017
Fetish

This is the continuation of Christine's day in her special room. Now that she's been prepared, you may recall that the doorbell rang. In this chapter Christine gets thoroughly examined and probed. And despite her humiliating situations, she submits completely and ends up with two cocks and a tremendous orgasm. * * * * * * * * * I answered the door. It was...

Case of Frustrated Analyst Ch. 08

by itsoktolust on Sep 16, 2017
Anal

A couple of weeks went by and I was getting in the mood, so I called the roommates and made a date for that afternoon. We went straight to the bedroom when I got there and stripped for action. The blonde was on her knees on the floor, bent over the edge of the bed and the Oriental was straddled on either side of the blonde, laid over on Rhonda's back. The...

Orla's Adventures in Porn

by scuik on Sep 16, 2017
Interracial Love

It had all happened so easily for Orla. It was only a week ago that she had met the guy who promised he would get her into porn and now here she was. In his studio. Ready for her first shoot. She sat on the sofa as he asked her some questions. Next to him was a camera man, a sound guy and another guy holding a clipboard. Their equipment pointed at Orla. "So...

Candy Holes Ch. 04

by MTL17 on Sep 11, 2017
Celebrities & Fan Fiction

Lita was feeling flustered, and not just because she'd been about to have sex with her girlfriend and forced to come here. Well, that was a big part of it, especially as for the first time in months she had been just about to fuck her girlfriend's big fat ass, but she was mostly flustered because she knew she was about to be humiliated, partly in public were...

Beyonce's Book of Bitches Ch. 02

by MTL17 on Sep 18, 2017
Celebrities & Fan Fiction

Hey Hayden, come to my hotel room tonight at 7 and bring Kristen with you. I have a surprise for you both. For what felt like the millionth time Hayden Panettiere read those words. It wasn't the first time she had received a text message like this, which was why she was so excited. Feeling a pair of eyes on her Hayden looked up from her phone into the eyes...

Humiliation

by mysticringer on Sep 25, 2017
BDSM

I should have known that silly frat competition would lead to trouble, and now it was too late. I'd joined up on a dare from my roommate. "C'mon," she told me, "it'll be fun!" Right. The competition turned out to be a battle of wits between two all-girl frat houses. Our frat lost. Now here I am, pulling straws to see who will be the one to pay up to the w...