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The Rebound

Summary:

In this sequel to The Runaway, Loona and James reunite for the first time in months since their initial encounter. After a Valentine's date gone wrong, Loona offers to make it up to James by treating him to a weekend with her in Hell. Experiencing the underworld for the very first time, and learning from Loona about life there, James soon realizes that it's not all that different from his own world.

Following having their weekend tryst get unexpectedly cut short, James is forced to abruptly return home, only to eventually get ghosted. Unsure if he is ready to move on or not, James is faced with a difficult choice: Keep waiting for Loona and hope that she eventually returns, or take his chances with another suitress. It doesn't take long for him to find out that a rebound from Hell is unlike any other...

Notes:

Trigger Warnings:

Erotic: The following story contains scenes of a sexual nature depicted in graphic detail, and includes acts of anal sex, oral sex (fellatio and cunnilingus), light bondage, forced oral sex and gagging (fellatio and cunnilingus), cream pies (anal and vaginal), whipping, hand jobs, tit-fucking, edging, sex toys, cum play, rimming, slapping, and sex with an anthropomorphic canine.

Mental Health: The following story contains some short depictions of emotional and psychological abuse from the protagonist's ex-girlfriend, primarily gaslighting. In addition, there is a very brief mention of suicide early on in the book. If you or someone you know is struggling with mental health, help is available. In the United States you can connect with trained crisis counselors by calling or texting 988 or by chatting at 988lifeline.org. For more information on finding support, you can visit FindSupport.gov, or contact the relevant agency in your territory if outside of the US.

Gay Relationship: The following story depicts several scenes and interactions between the straight male protagonist and his gay male friend. Some of these interactions may come across as crude or insensitive, however, they are not intended to offend anyone and are strictly for plot purposes. I have nothing but the utmost respect and support for the LGBTQ+ community, including several of my own friends and family whom I love and care for deeply.

Reader Discretion is Advised

Disclaimer: The author makes no claim to any of the copyrighted characters mentioned herein. This story was made with the sole purpose of entertainment and is not intended to be taken seriously in any social, political, or religious context under any circumstances. As such, the actions and/or viewpoints expressed by the characters in this story do not automatically reflect the opinions of the author. This purely fictional tale is not intended to educate nor serve as any kind of moral example to follow by whomever consumes this type of content willingly. Helluva Boss and its characters belong to Vivienne "VivziePop" Medrano and SpindleHorse Toons.

Note from the Author: Firstly, I would like to give a huge thank you to the AO3 community for the amazing reception I've received for The Runaway. What started out initially as a joke between my wife and I has inspired a creative side of me that I never realized I had, and the comments, kudos, and views have all been truly inspiring. Like my previous work, this piece has been written during my free time and in no way was it done professionally, the same goes for the editing. I've learned a lot since my last work and have tried to incorporate that into this piece, but just like last time there will be flaws in both the grammar and story flow. I will do my best to correct them as time goes on, and have started the process of updating The Runaway to match the formatting continuity of this work. With a little luck, that should be completed within only a day or two after this piece gets uploaded completely. That all said, I hope you all enjoy and that this meets the expectations that I have inadvertently set with the first piece. If you haven't read The Runaway yet, I highly suggest reading it first to avoid missing out on plot points and character development. If you have read it, but it's been a while, it probably wouldn't hurt to give it another read-through, especially now that's getting an update.

As always, thank you for taking the time to read this! Comments and kudos are always appreciated!

Chapter Text

“I’m telling you guys; this woman is from fucking Hell!”

     With my coffee cup in one hand, and my phone in the other, I looked up from the muted YouTube video I had been watching to observe the large gentleman at the shop break table. For what felt like the millionth time, he was proclaiming his frustrations over his wife. Gentleman was also probably the wrong title for Bill. The heavyset mechanic in his late-forties, with the beer belly and ZZ Top facial hair, paused from his exclamation to open his Igloo lunch box and withdraw a plethora of snacks and junk food. As I leaned against a large Snap-on tool cabinet belonging to one of the other technicians, I attempted to at least feign interest in his tale for the sake of maintaining diplomacy with my staff, while simultaneously trying to ignore whatever bullshit Bill was spewing this morning.

     The heavy commercial truck shop I managed wasn’t very large, only consisting of four bays for full-sized rigs and one smaller bay for heavy-duty pickup and service trucks that were popular with landscapers, highway departments, and the like. We had an equal number of mechanics, one for each bay, and aside from myself in the service office, the rest of our staff consisted of just a receptionist out front and the owner of the business, Tim. Tim had hired me on at a relatively young age, and over the years I had worked up from mechanic to now managing the shop itself. This was a feat that I took pride in, as I was still only in my early-thirties and respected the amount of responsibility placed on me by the owner.

     Working in the shop could best be described as a cozy environment owing to the small amount of staff on-hand. Even Tim himself only popped in here and there to check in on things, and we usually all got along very well. There was of course the occasional exchange of heated words amongst the crew when frustrations over jobs caused emotions to run high, but other than that no blood was ever shed, or at least shed from one another.

     Being based in a small town in the Catskills region of New York State meant work was regular, if not abundant, and the pay and benefits of the job reflected as much. Larger corporate shops and dealerships were often based an hour or more away from us, and the area was ripe with municipal crews and service industries that regularly required maintenance and repair on their fleets. Exposure of vehicles to both the harshness of the environment and less-than-gentle nature of the people operating them meant business was good.

     It was just past ten on a Tuesday morning, one of our two scheduled breaks aside from lunch, and I was already prepared for the work week to be over as I listened to Bill continue his story.

     “The bitch rides my ass as soon as I get home from work… clean this up, wash that, mow the lawn… I can never catch a fucking break!” he complained, before turning to our youngest mechanic Tommy, adding “Hopefully the girls you’re screwing don’t turn into monsters like that…”

     Tommy, who had once confided in me that he was gay and asked me not to share with the others, looked first to me then back to Bill with a face of confused indifference. I non-verbally replied to him with a simple shrug and knowing smile, before turning my attention back to Bill.

     “Bill,” I said, watching him pat Tommy playfully on the arm, “who packs your lunch box every day?”

     Tommy and the three other mechanics all smirked, knowing where I was going with the question.

     Taking a bite of a snack cake that he had withdrawn from his lunch box, he answered simply, “My wife…”

     “And she does the shopping too?” I asked.

     He nodded, “Yeah…”

     “And the laundry?”

     Bill nodded again.

     “I’m guessing the dishes too?” I continued.

     “Yes,” he replied, beginning to sound frustrated, “what’s your point?”

     I smiled back at him, before facetiously concluding “I don’t know how you do it buddy, living with the embodiment of evil…”

     Luckily, while Tommy and the others recognized I was subtly calling him out on being a dick about his old lady, Bill was none the wiser.

     Continuing to scarf down his snack, Bill said “Thank you! Leave it to the boss to be the voice of reason! You other guys never have any idea what I’m talking about!”

     I looked to Tommy one more time and rolled my eyes when Bill wasn’t watching. Tommy in return flashed a subtle smile back to me before returning to doom-scrolling on his phone. At only nineteen he was already shaping up to be a hell of a mechanic, and while he would occasionally struggle with certain jobs, because of his young age and associated aptitude he would run circles around the older techs when it came to anything electrical. Having started working at the shop about that same age, I unashamedly took him under my wing when he began his career a little under a year ago.

     His parents moved he and his sister up from a rougher neighborhood in the Bronx when they were still in middle school. While the Catskills are undoubtedly an improvement from whatever living conditions that gave his parents concern to move, they unfortunately moved to an area of New York where tolerance wasn’t always a certainty. To add to the struggle, Tommy took on a profession that was still very much dominated by older white males possessing something of a narrow world-view. To my great relief, aside from Bill occasionally being a bit of an ornery prick, the guys have all treated Tommy very well and helped to guide and teach him.

     As I took a sip from my coffee and started to return to fucking around on YouTube, my office phone interrupted my morning break. Sighing, I stuck my cellphone in my pocket and walked back over to my office with the large window overlooking the shop. In one way, I was annoyed at my break being cut short, but in another, I was happy to be free from Bill’s bullshit. He was more and more frequently referring to his wife as being from Hell, and it was getting harder for me to restrain myself from informing him that if she actually was from Hell, the real Hell, then he would probably be singing a different tune.

     Unlike Bill, who simply uses Satan’s Kingdom as another way to call his wife a bitch, I genuinely have experience with Hellish women. Well, one Hellish woman... a Hellhound named Loona. Not that a long weekend with a goth girl-turned-demonic furry truly qualified me as an expert on the damned, but it for sure gave me some level of exposure.

     Closing the office door behind me, I sat down at my desk and answered the phone mid-ring.

     “Service, James...” I answered professionally.

     “Sorry to interrupt your break, I just wanted to check in before the missus and I went out to the beach for the day” said the familiar voice on the other end of the line.

     It was the owner, Tim, who happened to be on an extended vacation in Florida for a few weeks.

     Leaning back in my manager’s chair, I answered casually “We’re all good here, the guys are all behaving for the most part and I haven’t had to file any workers comp forms.”

     I knocked on the wooden desk out of superstitious caution, before continuing, “You just missed Bill complaining about his wife for the fuckteenth time…”

     Tim laughed in my ear, “Still on the ‘bitch is from Hell’ thing?”

     “I’m not sure what he’d do if she actually was” I replied, only half-joking.

     While Tim and I chatted, my cellphone buzzed in my pocket. With the land line held up to one ear, I produced my personal phone and swiped the screen to a missed text message with an image attached.

     DINNER 2NITE? read the text, accompanied by a photo of a white and gray fur-coated ass. Projecting from the top of said ass was a long and bushy tail pointed upwards, one hand with black-painted claws pulling a cheek aside while the other held the phone camera that took the shot. A perfect camel toe peeked out between two muscular legs, completing the pornographic view.

     “Woof ” I exclaimed, just loud enough that Tim heard me.

     “Everything okay?” he asked.

     “Yeah, uh, customer just sent me a photo of their rear-end” I lied.

     “How’s it look?” Tim questioned, now under the impression I was talking about a truck axle.

     I gave the image a final look before closing the messenger app and locking my phone.

     “Could probably use some further inspection…” I answered.

     “Well, I’m sure you can handle it” Tim reassured.

     What Tim did not know, was that I had indeed handled it before. In fact, I was intimately acquainted with the rear-end presented in the image. The ass in the photo belonged to, and was sent by, the aforementioned Loona the Hellhound.

     About four months prior, we had our little tryst of a long weekend. Even though I hadn’t seen her in person since, she would send me promiscuous photos about once every other week. They were almost always shot from what must have been her bedroom in Hell, the colors of which being that of various shades of blues, purples, and reds, and usually accompanied by short and suggestive text messages. One of my personal favorites was that of her standing sideways in front of a mirror in red lingerie with a large red bow adjoined at the back, with the caption of UR GIFT IS READY.

     Changing the subject, Tim asked “Do you have any hot dates for tonight?”

     “Hot date?” I parroted, confused.

     “It’s Valentine’s, son! Surely an eligible bachelor such as yourself must have something arranged!” he clarified.

     I looked down at the large desk calendar in front of me; it was February 14th, and no, I did not have a date despite my boss’ confidence in my romantic eligibility. I wasn’t even sure still what to think of Loona and I, despite her semi-regular spicy texts and photos. Notwithstanding her ability to text me, I had no way to text her back.

     It wasn’t by any means for lack of trying; I had attempted on multiple occasions to reply back to her texts and photos. Unfortunately for me, the number Loona would contact me from was only identified as PRIVATE on my caller ID, and each time I attempted to reply to her I would receive a MESSAGE DELIVERY FAILED message immediately in return. I was sure that she had known this, as her texts had yet to question why I have not responded, but it was still frustrating that I had no way to communicate with her other than receiving surprise pics of her tits and ass. Not that the subject matter was a complaint, she still possessed an amazing set of tits and a gorgeous ass.

     “No Tim,” I said, “sadly, this bachelor is probably going to reheat some leftovers and watch a movie before bed tonight.”

     Sounding surprised, he replied “Whatever happened to your ‘company’ you had over a few months ago? Remember when we closed for that October storm?”

     “You remember that?” I said, surprised by his recall of such a small detail.

     It was a relatively short conversation, he having called me in regards to closing the shop down for the severe snow storm that hit while Loona was staying over and we were getting to know each other. I remembered the moment quite clearly, as I was nude and bound, Loona having tied my wrists behind my back with the belt from my own robe. Thankfully, Tim was not privy to that specific detail.

     “Of course!” he answered jovially, “I do my best to make sure you stay out of trouble!”

     I scoffed, “You’re going to have to try harder, boss.”

     Not pushing the issue further, Tim laughed at that.

     “Well, company or not, I hope you have a good Valentine’s” he said.

     I nodded, despite him being unable to see me “Thanks Tim, enjoy your vacation, I’ll see you when you get back.”

     Tim thanked me before hanging up, and I set the phone back down into the cradle on my desk. Leaning back in my chair, I pulled my phone out and looked at Loona’s text again.

     DINNER 2NITE?

     I rubbed my eyes in frustration, thinking ‘Yes, you beautiful bitch, I would love to!’

     Whenever I did see Loona again, discussing our phone plans was going to be first line item on the itinerary.