He Shoulda Known

By C.B. Roby

Craig fancies himself a romantic and yet he has never fully learned how to understand women. Oh, he thinks he does, but he has never been able to make a relationship work for long. He would say he's cursed with bad luck. Others, like his best friend, Brittany, would say he just has no idea what is good for him. She was one of his earliest failures. But at least she has stayed by his side as a confidant and occasional hook-up partner.

Knowing she'll always have his back is why he entrusts her with what he feels is the perfect plan to win the heart of Raylen, the latest object of his desire. Everything is under control until their friend Erica, an essential part of the scheme makes a request to secure her cooperation. Craig finds himself in a dream scenario, a chance to be with not just two women, but one who had seemed like an impossibility for so many reasons.

But all is not as simple as it first appears when the two women show up at his apartment. Before the first stitch of clothing is removed, it becomes clear that Craig isn't the only one with a plan in the works. He now finds himself in an emotional conflict as the innocent night of fun becomes something far more serious than he had ever expected.

• Language: English
• Publisher: C.B. Roby
• Release date: Sep 29, 2022
• ISBN: 9781005790813

C.B. Roby

I've always had a romantic/dirty mind. I fantasized about all kinds of women, real and imagined, in sexy domination and rescue scenarios. As far back as I can remember, I had a thing for the strong female character, or at least the persistent. Diana From V. Princess Ardala from Buck Rogers. Wonder Woman. And anything Cynthis Rothrock did.I never intended to make a thing of erotica. My high school dreams of being a writer had fallen to the wayside as life took over. And an early rejection didn’t help matters. I never completely let it go, rewriting bits and pieces here and there. But the past few years have reinvigorated me and made me want to go at it again. I decided that I would give myself a few practice runs with short stories and writing contests before I tackled the rewrite on the novel I had "finished" more than two decades ago.I started with my most replayed fantasy about a couple of lifelong friends who finally couldn't hold their feelings a secret any longer. After that, and the feedback I received from it, I couldn't stop. I do plan on getting back to that novel at some point. And the practice I put in building these erotic stories has allowed me to complete a few non-smut shorts. Until then, I look forward to entertaining you.

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He Shoulda Known

Published by C.B. Roby

Copyright 2022 C.B. Roby

Smashwords Edition

Smashwords Edition, License Notes

This ebook is licensed for your personal enjoyment only. This ebook may not be re-sold or given away to other people. If you would like to share this book with another person, please purchase an additional copy for each recipient. If you’re reading this book and did not purchase it, or it was not purchased for your use only, then please return to your favorite ebook retailer and purchase your own copy. Thank you for respecting the hard work of this author.

This is a work of fiction. All events are a product of the author’s imagination.

Table of Contents

Chapter 1: A Friend in Need

Chapter 2: The Humble Host

Chapter 3: Unbound

About C.B. Roby

Connect with C.B. Roby

Chapter 1: A Friend in Need

In a quiet diner tucked away in the corner of a small strip mall, Craig sat at a table alone idly sipping on his mango smoothie. The fruity concoction passing through his lips was the least of his concern, however. His thumb flicked the screen of his phone scrolling through his social media feed until he found her. Ah, there she was! That gorgeous songbird that had stolen his heart. A smile spread across his dark face, and he let a slight sigh seep out.

Raylen’s friends had been kind enough to tag her in the pictures they had taken a few nights before. It had been another fun night of drinks and karaoke with her killing it on the stage. Holding her mic up high as she belted out some tune, she was without a doubt, a sight to behold. And with any luck, he though, she would soon be his.

A jingle at the door grabbed his attention. He looked up to see Brittany step in. Blonde hair, a big smile full of teeth, and glossy lips practically bounced over to him on long athletic legs. He stood to meet her and was swallowed in an embrace. It had been a long time since they had been able to make time for each other. Former lovers that had been separated by circumstance, Craig and Brittany had remained best friends. And even though they had both moved on to other partners, the emotion that had brought them together had never completely gone away. It just wasn’t something that they were willing to build a relationship upon.

She met his plump lips with an unexpectedly warm kiss, and he pulled her closer. He was single at present, and her current boyfriend seemed to have been on her bad side for a while now. Craig usually benefitted from that. Sometimes he felt guilty about it because the guys were typically cool to hang with. He just couldn’t say no to Brittany.

Somebody missed me, he said.

Shut up, dork! she laughed, taking a seat at the table. A teenage girl was over to take their orders immediately. They were regulars at this place, a chain of Middle Eastern cafes she had introduced him to. While they waited for their food they caught up on each other’s lives. But it was all small talk while he waited for her to bring up what he was most interested in.

She let out a sigh, fully aware. Okay, so tell me again how this nutty plan is supposed to work?

He lit up with a toothy grin. It’s really easy. Raylen needs people to cheer for her at the contest. She told me they judge by applause. So, you and the girls just show up and make a bunch of noise. I figure I bring the loudest people I know. She wins. I tell her how I feel. Bam! I’m in!

Aww, she chided. Pooters is in love. That was her nickname for him because of his job repairing computers. Some of their friends used it exclusively.

He came as close to blushing as his brown skin would allow. I don’t know about all that. But we seem like we get along great when I get to spend time with her. And she’s so fucking hot. He thought back to an incident about a year prior when she had flashed him while passing him on the highway. The bra had stayed on, but even her flipping up her shirt to reveal her impressive size had been burned into his brain.

Seems like a whole lot of work for a girl that doesn’t seem like she likes you that much, she said, taking a bite of her falafel.

There had been a lot of winking and squeezing of her tits in front of him to convince him otherwise. And she was always inviting him to these karaoke nights, so she clearly liked having him around. But his attempt to tell her how he felt in the past had been dismissed as him being in the wrong frame of mind. I think she had a good reason back then. I was fresh off of Laura, and she wanted to make sure I wasn’t just trying to tag her in some rebound mess.

And how is now any different? she asked.

He forked up his sfiha. Your boy’s been bone dry for months. I think I’ve cleared the waiting period. And this will be perfect. I can’t see anyone beating her to begin with, but when she sees what I did to get her that trip to Hawaii… He raised his eyebrows and took a