GOOD FRIEND Volume 0: The Loophole

Jillian’s books contain intense adult situations
and are intended for mature readers.

If you are under the age of 18, this page isn’t for you.


This short story contains the secret origin of the GOOD FRIEND series.

Originally, I was giving this story away as an eBook for those who signed up for my mailing list.
It turns out, I’m terrible at managing a mailing list.

So I figured I’d just post it up here in its entirety for those who’d like to read about the origin of the GOOD FRIEND experiment.


“The Loophole”

Good Friend: Volume 0

By Jillian Hoff

Copyright © 2017

This is a work of fiction. Names, places, events, and incidents are either the products of the author’s imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, is purely coincidental.

It’s both the real start to a fake thing, and the fake start to a real thing.


It started out as a bet I had with my boyfriend.

We talked about the idea of confession, a topic sparked by some movie character going in a booth and doing one of those “forgive me Father” scenes. He said people don’t tell the truth in those situations. I said I thought they do. God would know if you were lying, or holding anything back, and so what’s the point? He said no one tells the whole truth when they’re talking to another person. I ignored what that might say about our relationship for the moment and asked if he thought it were ever possible for people to tell the entire truth?

Let’s pause for just a moment. My name is Abigail. My boyfriend’s name is Richard. I call him Rich most of the time, but he’s Dick when I’m angry. We’re in our mid-twenties, which is a euphemism for “nearly thirty.” Older people still look at us like we’re kids, and younger people think we’re ancient. It’s the sweet spot.

Anyway, back to the story. Rich said people would only ever tell the entire truth if they believed they were anonymous. The priest in the booth was a person who might judge, even if he didn’t know the one confessing. By his reckoning, the only way you’d ever hear real truth would be if a person offered it voluntarily and could express it with complete anonymity. This led to a lot more philosophical discussion. I won’t bore you with the details.

In the end, we came up with the idea for the Good Friend website project. I would build the site and Rich would help me with promotion. There would be no purpose other than to try to get people to tell their stories as truthfully as possible. We presumed guilt might influence the outcome and cause people to hold back, so rather than ask people to confess their sins we posed a simple question we figured could be answered many ways:

What’s the nicest thing you’ve ever done for a friend?

People would be able to write their answers and post them without creating an account or identifying themselves in any way. I honestly doubted anyone would respond, but Rich diligently posted flyers all over town on community bulletin boards and before long we saw some results. A handful of simple posts appeared, most mentioning lending money or helping people move. Stuff like that. The site got more traffic than we expected, and as people shared it around we saw more and more stories posted.

And my God was it all so boring. And self-righteous. Rich and I seriously considered changing the question before the first sex story came in.

After that though, the floodgates opened. A surprising number of people, women mostly, posted their tales as if writing in a secret diary. I wasn’t convinced they were true, but as luck would have it one of the stories involved people who were our friends in real life. I knew for a fact some of those details were correct. The person who posted that one had no idea I made the website though. It was a coincidence she found it and posted her story. It was a bit embarrassing, but I suppose that’s part of the risk of the experiment.

One night last week, Rich came and stood behind me while I was at my desk reading the latest racy post.

“Got a new one?” he asked.

“Un-huh. Another neighbor story. Who knew so many people did that?”

“You believe they’re true?”

“Well, yeah. Don’t you?”

Rich put a hand on my shoulder and squeezed.

“So that means I’m right.”

Oh shit. The bet.

“Well, we don’t have enough data yet to say for sure,” I said.

I haven’t explained our bet.

“There’s more than enough. If you believe those stories are true, that these people are being completely honest, then we have our answer.”

“Hold on a minute,” I said, stalling for time.

Our bet was if people held back or didn’t post at all, Rich would admit I’m right and understand more about human nature than he does. He would have to make a post about it for all our friends to see that I could refer to in future disputes. This was something he very much did not want to do. If he were right, however, and we found people tell a more complete truth when given this opportunity…

I had to let him fuck me in the ass.

Something I had never done before.
(As far as he knew.)

I wouldn’t mind paying up nearly so much as he would, but there was still the principle of the thing to consider.

“Did I win the bet, or not?” he said.

“We should wait awhile to be sure.”

“Be sure? People posted, they’re spilling their guts, and you know damn well that gym story is true! How much more do you need?”

“Yes. Okay? Yes! You win.”

He put his other hand on my other shoulder and leaned down.

“I’m going to collect,” he breathed into my ear.


“Right now.”

“I’m working. I’ll be done in a bit.”

“That wasn’t the deal.”

Damn him. The terms of the bet were he could fuck me in the ass, one time, whenever and wherever he wanted. Why did I agree to this again?

“You seriously want to do this now?”


He slid his hands from my shoulders to under my arms and lifted me to a standing position.

“Hey! I can get up on my own.”

He kicked the office chair out of the way and pushed me up against the desk.

“Yeah, but how much fun is that?” he taunted.

I pushed my laptop out of the way so I’d have room for my hands to hold myself up. Rich didn’t turn me around so I assumed he wanted me in this position, facing away from him. I should probably describe the scene for you a little more. My desk sits against the wall in our dining room, between the front room and the kitchen. There are no windows in there but if someone were persistent they could see in to where we were through one of the front room windows, or maybe the one over the kitchen sink. As Rich yanked my skirt and panties to my knees, it became apparent that was more than enough privacy for him.

“Someone could see us!” I said.

“If they’re peeking in our windows, that’s their problem.”

“Famous last words when it’s your ass that ends up on YouTube.”

“YouPorn maybe.”

“Oh, right. You’d love that, wouldn’t you?”

He shoved his hand between my legs from behind, brushing me with his fingers as he forced it down to my inner thigh.

“Worse things have happened,” he said.

He pressed to spread my legs but I couldn’t open them much with my clothes still bunched at my knees. Rich knew this before he tried, of course. He loves to make things difficult.

“My work wouldn’t find it so entertaining,” I said.

I was still dressed from my job, in fact, wearing a black skirt and a white blouse with my hair tied back. My work requires me to look professional. I had already kicked off my heels before I sat down. I was glad for that; Rich would have insisted I keep them on in my half-tangled state of undress.

“If a lady wants to get ass-fucked in the privacy of her own home, it should be none of their business.”

“Who said I wanted to?”

Rich pressed with his hand again, and again found that my legs wouldn’t open.

“Do something about that, will you?” he said.

I reached back and maneuvered to get my hand down to my knees. Rich didn’t move out of the way or assist. Instead he began unbuttoning my blouse with his free hand. I managed to push my skirt and panties past one knee with my fingertips and then shook my legs to let it all fall to my ankles. All I had to do now was step out of it, but that would have required Rich to allow me another second to concentrate. Instead, as soon as my legs could spread, he pressed my thighs apart, turned his hand, and pulled up to cup my pussy with his palm.

“Give me a little room here,” I said.


He slid his hand back and pressed up with his fingers. They slid between my folds and became coated with my juices.

“You fucking love this,” he said.

He’s right. I do.

He curled two fingers and shoved them into me. I tried to stay silent but barely suppressed a gasp.

“You’re all wet and ready to go, like the slut you are.”

I was.

Not a slut, but I was ready. The truth is, I love it when he acts like this. He never raises his voice to me in public, has never shamed or belittled me in front of anyone, but the second we are alone and naked I become a whore and a cunt and a bitch who deserves what she’s about to get. No one would expect this from him. It makes me weak in the knees.

Don’t judge me. I’m sure you have your own messed up kink. If you’re lucky.

Rich finished unbuttoning my blouse and reached inside to grab my breasts. He snorted with derision upon encountering the fabric of my bra.

“Why is this still on?”

“Because I didn’t know you were going to be like this tonight.”

He moved his hand around behind me and shoved between my shoulders to bend me down across the desk.

“Get rid of it,” he commanded.

I reached behind my back with both hands to unclasp my bra. Rich began thrusting his fingers in and out of me to make it more difficult. It did. Wonderfully.

With some effort I unclasped the bra and with much more I navigated it through the arms of my blouse. Before I had it all the way off his hand was back, his fingers pinching my nipple hard.

“Oh, God,” I said. I was still trying to hold back on giving Rich any satisfaction, but some things force their way out. It’s all part of the game, but I have to admit it’s a game he’s better at. Rich twisted his hand between my legs and curled his fingertips into my G-spot. I won’t try to spell the sound I made.

“That’s what you like, isn’t it?” he said.


“You deserve to get fucked.”


“I should drag you outside and fuck you in the front yard so the neighbors can watch you beg for it like a bitch in heat.”

I didn’t answer that one, but I couldn’t really anyway. Rich was massaging and tapping with his fingers inside me while pinching hard with his other hand. He had stretched his fingers across and managed to get ahold of both of my nipples. He squeezed and twisted, just enough.

It hurt. I came.

I pressed my forehead into the polished wooden surface of the desk and tried to hold my scream between gritted teeth.

My juices drenched his hand.

“That’s right,” he said. “That’s what I need.”

Rich pulled his hand out of me and stroked upward, back toward himself, slathering my asshole in my own cum. He pressed a finger in to the second knuckle.

“You ready for it?”

I looked up from the desk, back over my shoulder.

“Are you?” I asked.

Rich smiled and stepped back from me to unbuckle his belt. I used the opportunity to step out of my clothes and wriggle into a slightly more comfortable position. He dropped his pants and pulled his hard cock out from his shorts.

He gripped it in his fist like a weapon with a look on his face that said now you’re really gonna get it. I smirked at him. I couldn’t help it. He had so much confidence in such a little thing, like so many men. Not that he is small; he has a big dick compared to most, but nowhere near so large as the pride on his face as he stepped forward to use it on me.

“You think that’s really something, huh?” I said.

He responded by jamming it into me, hard.

Rich stopped, his cock as far inside as it would go, and held it there. He wasn’t in my ass. That would have taken more maneuvering and negotiation than simply slamming it home. Instead, he was deep in my pussy, which was more than ready for him.

“Oh, yes!” I cried. So maybe it was something after all. Whatever the case, it felt great.

Rich gripped my ass cheeks and pumped slowly in and out of me. I turned my face to the desktop and pushed back to meet him and force it in a little faster.

“That’s right, you’re my push-back girl. Most sluts just take it but you’ve got to get some for yourself.”

I pushed back harder, and then faster as he sped up his thrusts. Our bodies made that sound of sweaty skin slapping together you only hear during the really good fucking.

It went on like that, hard and fast, and I wondered how he would have anything left if he kept up that level of intensity. I looked over my shoulder at him again and saw his approaching “O” face.

“Oh! Save some for my ass, baby.”

And that as all it took. He groaned and bore down hard on me, releasing a huge load of jism into the wrong hole. He squeezed so hard he left fingerprint bruises on my waist as he slammed into me two or three more times.

After that he collapsed for a moment onto my back. The pressure inside was gone as his cock softened in my pussy. He looked up and caught my eye.

“Save it for my ass?” he said.

“Push-back girl?” I said.

And then we both cracked up laughing, which is usually how these things end.

Rich disappeared to the bathroom and left me to clean up as usual. As I attempted to put my clothes back into some semblance of wearable order and keep the cum from dripping out of me, I realized that despite what happened Rich had not technically collected on the bet. The deal was he would get to fuck me in the ass, and he had not done that. I suspected this had been his plan all along and my suspicions were confirmed the next night when he pulled the same thing on me again.

This time it was the kitchen floor. I was lying there on my back with one leg up over Rich’s shoulder and his leg over my other leg so that he was fucking me halfway between doggy and missionary. I had both hands on my ass spreading it open for him and was well lubed and ready.

“Now, baby. Now. Put it in my ass!”

This resulted in him pulling out and shooting so hard I probably got half of it in my hair. Again, he got sex on demand when he wanted it and no collection on the terms of the bet. As long as he finished before putting it my butt he could make the case that I hadn’t paid him off yet. And all through it he’s got me begging him to fuck my ass, which I know he gets off on. Devious bastard.

I’m letting him get away with it for now because it’s fun. There is something exciting about not knowing when you’re going to be taken, even if it is by a guy like Rich.

I’m kidding, obviously, but what I am serious about is posting this story in detail to our very own website as a present to Rich. That way he can read over what I post and verify that I have been completely honest in my recounting of the events and therefore he did indeed win the bet fair and square.

People will tell the truth. Most want to stay anonymous when writing up these kinds of posts though, so they change the names in the story.

I didn’t.

You can get all of Jillian’s GOOD FRIEND stories for Kindle HERE.