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Chicago Billionaires

Looking For Trouble

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“Most of the time, when I tell someone to do something, they obey me, Presley. Maybe you need a gentle reminder?”
I wasn’t looking for trouble…at least that’s what I told myself when I met him.
Wrapped in a bespoke suit and twenty years older than me—Cyrus Gates, the heartless billionaire of Chicago and my new professor.

The funny thing is, he doesn’t remember that we’ve met before and it’s probably best for my sake that he doesn’t but that doesn’t stop me from reminding him.
I should have known in that second when his lips curled in a devious grin, his dark eyes raking their way slowly over my body as my stomach flipped…I’m merely the innocent little prey to his insatiable predator.

When I moved to Chicago for college, I promised myself I’d let loose but here I am in my last semester of grad school and I’m still the same good girl.
But inside, there’s someone else dying to break free.
A woman who wants to explore the world on her own terms.

With a reputation like his: cold, calculated and every bit the domineering powerhouse the world makes him out to be, Cyrus is the kind of man I should run from.
The kind of man that gets off on conquering anything and anyone

But he comes to me with an offer I can’t refuse—a publicist job at the most prestigious public relations firm in Chicago tasked with cleaning up his image.
The catch…he’s the client.

No matter how much I try to stand up to him, no matter how much I try to fight my desire, he can see straight through me.
Something inside me ignites, knowing a man this powerful wants me and has no shame expressing it.

But this isn’t just an innocent game of cat and mouse—it’s a lesson you learn the hard way.
He’s risking losing a multibillionaire dollar deal of a lifetime and I’m risking my career.

He warned me—he isn’t the kind of man you just walk away from unscathed, he’s the kind of trouble you don’t want…but I didn’t listen.

Instead, I dove in head first with a heart of glass, falling for a man who doesn’t have a heart at all.

But you know what they say about trouble…if you go looking for it, you’re probably going to find it.

322 pages, Kindle Edition

Published March 13, 2023

1528 people are currently reading
768 people want to read

About the author

Alexis Winter

119 books2,157 followers
Alexis Winter is a contemporary romance author who loves to share her steamy stories with the world. She specializes in sexy billionaires, cocky alphas, brooding bad boys and the women they love. 

If you love to curl up with a good romance book you will certainly enjoy her work. Whether it's a story about an innocent young woman learning about the world or a sassy and fierce heroine who knows what she wants you're sure to enjoy the happily ever afters she provides.
 
When Alexis isn't writing away furiously, you can find her exploring the Rocky Mountains, traveling, enjoying a glass of wine or petting a cat.
 
You can find her books on Amazon.

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Displaying 1 - 30 of 140 reviews
Profile Image for Céloise.
383 reviews235 followers
December 5, 2024
☆1 DNF 33% When you’ve got an age gap of 20 years, you’d better serve up a hero who’s a grown-ass man. 🥱

Confused by all the glowing reviews but whatever. I quit because I couldn’t take the whiplash of Cyrus’s pull-her-in-then-suddenly-push-her-out (literally, of his car, his office, his PR firm, his personal space, his favorite bistro, his home gym, his good graces). Like make up your mind and have some self-control, asshole. Stop embarrassing your student/publicist (odd) by forcing her into these close confines, threatening her with a good time when she flirts, then harshly kicking her out or running away. His dirty talk isn’t bad, but I hate how he alternates between lecturing Presley on having a spine and demanding respect…to admonishing her for breathing his same air because he wants her in his bed and keeps getting grouchy every time he realizes he can’t. 🙄 Too predictable and annoyingly repetitive. He’s 46. Know what you want and be mature about it, don’t string the girl along and make her feel dumb. Also I feel like this needs editing down; it would make more sense as a novella with the amount of substance given to the characters and plot. Or you know, just start over with a better H, that works too.
Profile Image for Kristy.
313 reviews32 followers
September 22, 2025
Did you say billionaire boss, age gap, professor/student romance…well I’ll absolutely read that!! Presley and Cyrus meet at a bar where she scoffs at his shady dealings, they have a discussion and go their separate ways. Only 4 weeks later they meet again where Cyrus is her professor for a semester. Presley is the ‘good girl’ until one day she meets Cyrus. And the mouth Cyrus has…🥵 🥵
Profile Image for Cheryl T.
224 reviews
February 26, 2023
Who doesn’t love a bossy billionaire with a stone cold heart who learns the power of love from a ray of sunshine with a heart of gold?

Cyrus Gates has a reputation for being ruthless in business and in matters of the heart. He doesn’t give a shit about what others think about him and has closed himself off to pretty much all emotions. He is, in the words of chapter 1 Presley, not a very nice guy.

Presley James is a good girl, just trying to break out of her good girl shell and embrace her inner bad girl. Her morals are black and white with no shades of grey in between, and Cyrus wants her to see that not everyone thinks the same as her and sometimes people don’t have your best interests at heart.

So jaded meets optimism and sparks fly. These two cannot get enough of each other. What Presley first sees as “not a nice guy” she realizes is confidence and experience that excites her and pulls her in. And what Cyrus sees as naivety is what causes his walls to come down and his hardened heart to feel.

I really enjoyed this story. The steam was fantastic. I love a good age gap story. Age is just a number. If you’re both consenting adults then you do you. The professor and student angle was fun. How are you not caught ogling your student right in front of everyone?! So risky!! I also liked that Cyrus constantly boosted Presley’s confidence. She was so quick to disregard herself, but he made sure she knew how smart and beautiful and amazing at her job that she was.
Profile Image for Frances Hernandez.
744 reviews5 followers
March 3, 2023
I received this ebook ARC, from the author, on the condition that I write an honest review.
I can’t ever say enough about the books written Alexis Winter, her books always have well developed characters involved in a heartfelt romance. This book deserved more than 5 ⭐️’s, and extremely hard to put down. I was hooked from the very first chapter.
Cyrus is a very wealthy CEO, of a company. He is an older man, single, and very alpha, and a College professor. He meets Presley in a bar, and is immediately attracted, even though she is years younger than him. He attempts to stay away from her, but situations occur where he becomes close to Presley.
Presley realizes that Cyrus is her college professor, and they both begin to flirt. He refers her to a job with his PR company, this leads to them spending more time together. A relationship develops, but it has to stay hidden. They both agree that it will be a friends with benefits, with an eventual ending.
The relationship continues, while business complications occur for Cyrus. The stress causes Cyrus to break up with Presley, that and he feels guilty about the age difference. She goes out of town to get away, and possibly find another job. Cyrus realizes that he loves Presley, and follows her to Chicago, to prove his love for her. After this the couple finally obtain their HEA, with a beautiful last chapter
Profile Image for Skye.
8 reviews
May 20, 2023
tbh I just skipped past the last sex scene because I was just over it by that point. Dude gave me whiplash with his "i want her/jk lol no" BS.
Profile Image for Gabby (bookishandballgowns).
522 reviews25 followers
March 26, 2023
It is hot in here???? Or do I just have daddy issues???

Okay, this here is a prime example of characters using the term “Daddy” and it being absolutely the most cringey thing I’ve ever encountered. Making me absolutely screech in horror, but also giggle like a little school girl. But dang if the sum of all its parts didn’t make me five star the crap out of the book.

Presley James is THE Good Girl. The one that’s never stepped a toe out of line. The one with good grades. The one that applied for grad school. The one that’s about to graduate and dominate the public relations field. Until one day while sitting at a bar, she scoffs at and then calls out a rich billionaire on his shady dealings.

Cyrus Gates is not the type to be surprised often, but something about this bold young girl catches his attention. The two have a great conversation (cough cough argument but semantics) and go their separate ways. Fast forward four weeks when much to both of their surprise, he ends up being her ethics professor for the semester. Lucky for her, Cyrus Gates doesn’t hold a grudge. He’s intrigued by her determination and goes out of his way to connect her with a public relations legend. The catch: he’s her client.

And thus the tension between them begins. Presley is tasked with working as his new publicist. Cyrus is not an easy person to tame. And they are both driving each other crazy.

These two are the embodiment of forbidden. Billionaire and the average Jill. Mid 40s guy and mid 20s girl. Professor and student. Client and employee. The hits just keep coming. There’s so much that is standing in their way but the attraction levels are off the charts. They shouldn’t fit so well together, but no one can deny their crazy chemistry. Despite her good girl status, Presley was soooo down for anything. And honestly girl, I get it. Cyrus is pretty horrible, but in a fun to read about way. Yes, real me would run for the hills. But the I’m just trying to read my little book and fantasize version of me was LOVING it. He’s rude, pushy, and a jealous beast of a man. But cute and cuddly Presley mellows him out.

The books was such a fun ride. I FLEW through it at record speed. Despite a fairly common premise, the book still felt fresh and exciting. I simply had to know what was coming next. Especially with how not sneaky they were being. I was on the edge of my seat. As always there’s craziness in the third act, but it wrapped up nicely. I only wish we could have been flies on the wall when she told her parents they were dating 😂😆. I can only imagine how chaotic that was.

Highly recommend if you love a good spicy billionaire romance. This series is comprised of complete standalones so you truly can jump in anywhere with no interconnecting characters.
Profile Image for Emily Johnston (Booked.Up.With.Emily).
1,571 reviews114 followers
March 3, 2023
Absolutely loved this book! I am a sucker for all of the tropes that this book had!!

Age Gap
Student/Professor
Boss/Employee
Grumpy/Sunshine
Daddy Kink

Cyrus and Presley meet at a random bar one night and there is an instant attraction, but nothing happens and they never expect to run into each other again. That is until he walks into her graduate class as her new professor.

From there, Cyrus helps Presley get a job with the PR firm that he uses and she becomes his new publicist.

The push and pull from Cyrus is strong. He knows that it is wrong to want someone who is 21 years his junior, his student, and his publicist, but there comes a time where his control breaks and they finally get together. Their spicy scenes were HOT HOT HOT. And if you have read anything by Alexis Winter before, you know that she writes some good spice!

As with all relationships, there is always something standing in their way. But will all of the reasons that they are wrong for each other outweigh the feelings that they have?

I really loved both of these characters. Presley was a ray of sunshine and the natural good girl, who hasn't done anything wrong or scandalous in her life. Then there is Cyrus who is a walking scandal - always in the press and not for good reasons. These two are the complete opposites and you would have never thought that they would work. But they fit so perfect together.

I would love an extended epilogue to see them five years later (and let me tell you, I never want more epilogues lol)
866 reviews9 followers
April 5, 2023
The Ethics of Love

Beautiful, bright and self-confident, 25-year-old Presley James, in her last year of Business and Finance graduate school at the University of Chicago, knows who she is and what she wants in life. The blue-eyed, auburn haired, only child of doting parents has always enjoyed the opportunities her parents’ support has provided and has always striven to please them. And while she has had a couple of relationships during her college and graduate years, she has always been conscious of wanting to honor her parents’ values—no raucous partying or inappropriate relationships. She was a good girl who never strayed from the values of her homelife.

Now, as she approaches the last semester of her graduate degree in business and finance with a focus on public relations, she is thrilled to have been hired for an internship with Lisa Wade’s highly regarded Chicago PR firm. And, she is almost immediately assigned to work with one of Lisa’s college friends from their days at the university, Cyrus Gates, the handsome, single, commanding 46-year-old CEO of Gates Enterprises, a powerhouse company in mergers and acquisitions.

But currently, Cyrus has hit a wall with his negotiations with Meridian Telecom’s, the next company in Cyrus’ sights to add to his portfolio. The board of Meridian has a strong vision of their public image in the conservative communities in which they operate. They are concerned that Cyrus’ public image and reputation as a player. As a single man whose nightlife is often on the frontpage of local tabloids, the board is leery of the damage his image might do to the Meridian brand, especially when he has been recently labeled as, “notorious for being reckless, unmanageable, and oftentimes downright unethical.” And, to complicate matters, another acquisition company owned and operated by a local competitor, Peter Frisk, who holds a personal grudge against Cyrus, has entered the competition for Meridian.

What further complicates Presley’s internship with Lisa Wade and her assignment to work as Cyrus Gates’ PR handler is that Lisa has already begun Cyrus’ PR rehabilitation by arranging for him to teach a graduate class at their alma mater. Cyrus will teach the graduate class, Ethics in Business, a class which includes in its membership, Presley James, his PR handler.

Alexis Winter once more engages the reader in a delightful romance of an older man and the smart, clever younger woman who wins his heart as she strengthens his and his company’s public image. The author provides the reader with a thoughtful romance filled with unexpected connections and results.

I received an ARC from Booksprout, but always purchase a romance by Alexis Winter.
Profile Image for Jenn .
741 reviews15 followers
March 13, 2023
Looking for Trouble is the latest in the Chicago Billionaire Boss series by Alexis Winter. All the books in this particular series are complete stand alones and are actually not interconnected- so you truly can just pick one up and simply enjoy it.

3.5 ⭐

There are some things that you will need to know about Looking For Trouble... this book has...
❤ BIG Age Gap
🖤 Professor/Student AND Boss/Employee vibe
❤ Total Opposites... Grumpy Alpha Hero with the Sweet, Naive Heroine
🖤 Call 911- there is some FIRE in these pages
and so much more....

Cyrus Gates and Presley James pack a punch in this story- and while I didn't love it as much as I have some of Alexis' other work there was still something about these two that kept me intrigued.... it was probably the sex though.

Cyrus may be an extremely successful billionaire having made a name for himself in business by playing into the stereotypes that others loved to saddle him with but he was always brutally honest about all of his moves. Presley is a grad school student that comes from a small town and still hadn't quite broken out of her good girl mold- who just so happens to strike up a conversation with Cyrus one night at a bar. And because fate has a sense of humor- Cyrus in an attempt to clean up his image some is the guest professor for Presley's class on Business Ethics. Their story has some unexpected twists pushing them together even more- tempting Cyrus with the forbidden and teasing Presley with letting go and finally engaging in some of the wild bad girl behaviors that she had kept under lock.

I think that while their story is filled with so much dramatic dynamics, twists and hella heat there were parts and moments that were all just a little too much. Like there were moments of just over-dramatics and things quickly escalate from nothing to 1000 when it wasn't really warranted or necessary. I know that Cyrus has that dominant sexual side that paired will with Presley's more submissive/tell me how to please you side- but there was a moment when Presley was still simply his publicist that just kind of felt like Cyrus moved forward sexually before she consented to wanting that kind of relationship with him and I didn't love that. Sure they had flirty moments prior to that in the story but flirting wasn't a green light for more.

I did like the changes in the character development through the story- by the time we get to that third act grovel and epilogue I really loved these two together. So while it wasn't my favorite it was still an entertaining read.
Profile Image for Nicole.
1,317 reviews23 followers
March 19, 2023
Looking for Trouble is full-length standalone novel with no cheating or cliffhanger complete with a happily-ever-after. A billionaire boss romance. It's beautifully written with extraordinary characters and a great storyline that keeps you engrossed and turning the pages until the end. A steamy slow burn romamce filled with suspense, scandal and secrets. This is Cyrus and Presley story.
💋Billionaire Romance
☑️Age Gap Trope Story
☑️Professor/Student Relationship
☑️Workplace Romance
☑️Close Proximity
💋Twenty Years Age Gap
💋Grumpy Sunshine
☑️Forbidden/Taboo Romance
☑️Daddy Kink
Cyrus Cates is a forty-six year old heartless billionaire bachelor of Chicago who's always in some type of scandal and has his face plaster over one magazine or another. He's in need of image makeover. Cyrus is in the middle of a multimillion dollar business deal but his past actions has rear it's ugly head and threatens the deal, his manager has informed him to hire a PR firm to clean up his image. The firm is run by Lisa who tells him that he will teach a class at his old Alma Mater, University of Chicago. Presley James is a twenty-six year old student in her last semester of her master studies of grad school.
She's a good girl and never done anything. After she moved from her small town to Chicago she made a promise to herself that she would let loose but she never did. There's a woman inside who wants to explore the world on her own terms, and is dying to break free. One night Presley went to a bar, she meets Cyrus and the two was attracted to each other, they flirted but didn't acted on it. Presley told him about himself and Cyrus was drawn to her sassiness. Fast forward four weeks later she went to her Business Ethics and in walk in Cyrus Cates as her professor. He doesn't remember Presley. Cyrus PR handler quits the firm and Lisa is need of a replacement Cyrus suggests one of his student in his class, Presley. Presley is smart, Intuitive, and artistic and recently loss her job. Lisa hires Presley she was assigned as Cyrus new PR handler. His PR firm is prestigious firm and one the best. The two entered into secret relationship it was sensual, erotic and mind-blowing with Cyrus dirty talking. Presley was the perfect submissive for dominant dom. There was some was drama, blackmail, passion, lust, enemies, dominance, BDSM, complications, emotions, angst, secrets, steam and so much more.

I received an advanced copy of this book via Booksprout and I am voluntarily leaving a review.
Profile Image for Kim Nicole.
694 reviews1 follower
January 24, 2024
I have to tell you, this one was just as good as the last! It had more of the same things, except in this case it was a completely different scenario. Cyrus and Presley couldn’t get away with as much as Weston and Daphne. Cyrus and Presley were the epitome of forbidden. Not only was she his student, but she was also working on his PR campaign that is supposed to make him look better. Cyrus definitely had two sides to him and you get the pleasure of reading about both of them. He had his ruthless, bossy, angry facade, and then he had his sweet, tender side. We don’t see his second side until more deeply in the book because he maintains his tough guy, doesn’t care what anyone thinks, closed off, attitude throughout most of the book and with Presley. He does this only because he was scared about his feelings and how he doesn’t trust easily and thinks everyone has a motive. He didn’t want to fall too quickly for Presley because of being burned in the past, not by an ex-wife or lover, but from people taking everything from his family, leaving them with nothing because of poor deals and business choices. He was scared she would fuck him over but soon finds out that’s not the case. Meanwhile, Presley had her own emotions she was trying to keep in check and not give her all to him most of the book because she thought he didn’t want a relationship, nor would he thrive in one. It’s another case of assuming and afraid to talk about emotions and getting vulnerable with one another. My favorite parts of this book were the moments Presley and Cyrus had no inhibitions and had their walls completely down with each other and were just talking about life, their hopes and dreams. I also enjoyed the times when Cyrus and Presley were gentle with each other and it wasn’t about who can release the quickest and roughest, it was about worshipping each other and taking it slow, making love if you will. Those moments were the sweetest and most satisfying for me. Aside from that, I was happy to read that there was no major shoe dropping event that would cause the other to feel betrayed, especially since I thought this would happen a few chapters before the end of the book. I predicted it and the author surprised me by not doing that which you will see in a typical romance these days, at least the ones I read. Overall, another 5 for me. I couldn’t put this one down either and now I’m wondering if this is it for the Chicago Billionaires or if the author is going to keep building on this series, especially since the characters don’t mix with each other.
Profile Image for Maddie (Bookaholic_Dreamer).
959 reviews80 followers
February 28, 2023
Looking For Trouble is the fifth Standalone from Chicago Billionaire series by Alexis Winter.
This Age-Gap, Professor/Student, Forbidden Romance follows Cyrus Gates and Presley ‘Pres’ James through the telling of their dual POVs.

When it came to Cyrus and Presley, their story had you navigating through a whirlwind rollercoaster.
Particularly when you took into account the ups and downs occurred, due to the hurdles and obstacles they faced. Resulting in an emotionally charged ride, that Alexis laid out clearly in showcasing through the dual POVs of Cyrus and Presley.
The exploration of their characters from their perspective opened them up on a deeper level. Pulling back their layers and revealing all that was underneath, particularly through their inner monologue. That in which they expressed their thoughts, views and emotions when it came to their feelings.

The chemistry between Cyrus and Presley was very much alive with sparks flying higher in each and every interaction. From the witty banter they shared, going back and forth, it was truly entertaining, hilarious and Hot AF to watch it play out.
Especially since at times, Alexis had you guessing, not knowing what would be around the corner. Keeping you on your toes in following from anticipation and intrigue, considering Cyrus and Presley journey had you veering through a whole heap of emotions, duet to their budding romance. On top of the angsty-ness that was delivered on top.
Making it no surprise it was a bumpy ride, though mainly because of the forbidden Professor/Student relationship element and the drama surrounding it. And the fact that they were complete opposites when it came to their lives in where they stood and their personalities.

If there is one thing that Alexis Winter knows how to do, that is writing a Contemporary Romance.
Not even just that, she ensures that the story is well rounded with delivering many elements that makes it a filling storyline.
And that was what Looking For Trouble ended up being, an overall enjoyable read filled with laughter, steam, entertainment and some deeply felt moments courtesy of Cyrus and Presley.



*I received an ARC in exchange for an honest review.
Profile Image for Bonny Read.
523 reviews19 followers
April 27, 2023
Hot, Sweet Age-Gap, with great couple interaction

This is part of Winter's Billionaire Boss Romance (Chicago Billionaires) series. This is book 5 of 5 (so far). I'm obviously loving this series because, without realizing it, I've purchased all 5 books at one time or another. It wasn't intentional...one would pop up on my social media feeds and the blurb would catch my interest and I'd buy. I've read all but one to date.

I loved this one. I admit that I had to take a break from it. I don't handle angst in stories well. Particularly when it's to do with something that you KNOW will blow up in the couples faces and cause problems. And I just KNEW it was going to happen and cause all sorts of problems. I just couldn't take the waiting. (I also had another project I needed to finish so it gave me an excuse to take a break). So, I finally got back to the story, and yes...it does happen; but...thankfully, it wasn't a big blow-out. Instead it was a small leak and the H handled it beautifully and easily. (Should have known this smart, cunning alpha would handle the situation and not let his enemies get the better of him.)

In truth, he was his own worst enemy; because of something in his past, he's kept himself isolated from others, never letting anyone get close, never having any serious or long term relationships. He has something of a reputation. The h is just the girl to break down his walls. She's smart, sassy and challenges him. She manages to sneak in without him realzing it. But this is an age gap romance (20 yrs difference), so even when he finally admits to himself he has feelings, he still lets her go believing she deserves someone closer to her own age. Don't worry...he comes to hs senses.

I love the play between these two. There was some real meaningful interactions and conversations as well as the hot and spicy ones. They challenged each other. Even though the MFC was raised vanilla in a small town, she knew what she wanted and needed and wasn't afraid to go after it. The MMC is supposed to be this ruthless, business tycoon lacking any ethics, but the author slowly reveals his truth and we see that he has his own moral code of ethics. Yes, he can play dirty, but only if you play dirty first. Loved both characters and ths story.
895 reviews4 followers
March 23, 2023
Looking For Trouble - Count Me In!!!

Aptly named, Cyrus & Presley are not necessarily looking for trouble but there’s all kinds of trouble sniffing around them! Cyrus is a mature hard-nosed alpha male who needs to clean up his image in order to secure a business deal. Presley is a young student in Cyrus’ class. She is gorgeous, young & smart. Even though she looks shy & insecure, she is a temptress waiting to experience the naughty side with the right guy. With Presley pushing his buttons by challenging him, teasing him & their bantering back & forth, Cyrus’ strong stamina weakens every time they are together. The sexual tension is intense, leaving the reader wondering if one of them will snap, wanting to fulfill their fantasies & let their desires for the other person take over. Presley’s knack at being a great publicist, has Cyrus changing to be a better person & more approachable. He’s still a bad-ass in the business world but he does get what he wants & does his homework, having the upper-hand when other businesses try to screw him over.

A stand-alone billionaire novel, part of the Chicago Billionaires series, is one that will catch your attention & keep you interested in whether Cyrus & Presley can really pull this off in having a HEA. She works for him part-time as his publicist, there’s the big age gap difference & she’s a student in his class, all of which are big no-no’s in the eyes of the general population. Do they care what others think of them hooking up? Pick this novel up & enjoy their chemical tensions & their attempt to deny their deeper feelings for each other. Another one of Alexis Winter’s stories I absolutely love to read & always look forward into what’s in store for her next characters’ adventures!

I received an ARC of this book via Booksprout and am voluntarily leaving a review.
Profile Image for Rena Spensley.
85 reviews2 followers
March 2, 2023
Looking for Trouble was a good addition to the Chicago Billionaire series; I normally devour Alexis' books but there was something about this one that wanted me to take it slow. I didn't want it to end. As of lately age gap has become my favorite book trope and Alexis knows how to write them so perfectly.

The chemistry between Cyrus and Presley is off the charts steamy, it has the subtle hints of a dom/sub relationship that isn't too over the top.

Cyrus is your stereotypical billionaire. He always gets what he wants in and out of the boardroom/bedroom. Presley is your sweet and innocent women who grew up in a small town just outside of Chicago and isn't very "experienced" if you know what I mean. So basically, Cyrus needs help on the business front of things and has to hire a PR representative to help close a merger deal. While doing this he takes on a teaching job at the University of Chicago, where Presley is a student. She is smart and driven and he finds that and her very attractive, when he finds out that his PR firm needs a new representative, he gets her an interview for the position which she ends up getting. The account she has to work on of course is his, so now not only is he her teacher, but he is also now her client. The more time they spend together only sparks the mutual attraction they have for one another, and you can only guess what happens next. I'm not going to give anymore away you'll need to read the book to find out the rest of the juicy details. I can guarantee you though it does end with an HEA.

I received a free copy of this book via Booksprout and am voluntarily leaving a review.
Profile Image for Maz.
1,670 reviews29 followers
March 12, 2023
This was a Forbidden, big age gap (20 yrs), Boss/Employee and some Dom/Sub kink Trope.

I literally inhaled this book from start to finish. I alway love Alexis' books. She always manages to pull you into the story and make you feel.
Cyrus was a successful business man and is deemed to be heartless. He doesn't let himself feel and live the disappointment life people expect from him, all because of his past.
To clean his reputation he needs to stop all this and work as a professor, so he can finalise a deal.

Then there's good girl Presley that's studying business etc. It's her final year. She is a wonderful woman that wants to explore her wild side but is too scared.
For the 2nd time she meets Cyrus and this time he is her professor. They have some sort of immediate attraction. But they are both sooo off limits for all the reasons.
He can't pursue her as he needs to keep his profile clean.
But they both can't help but goad each other every time they meet.

I loved their flirting and interactions. They made me smile every time. They fight for soooooo long, I was worried they weren't going to give in at all haha.
When they do, wow, the chemistry is combustible. The Steamy scenes were written so well and I loved every single one of them.

You know what they say about things being forbidden for a reason. Things kind of blow up.

Can they actually maintain a relationship without involving their hearts?
Can they survive being in secret relationship?
How will they come back from the epic blow up?
Who is enemy within Cyrus' business?

Go and get your copy ASAP.
Profile Image for Jela  Heneghan.
358 reviews19 followers
March 14, 2023
Seriously steamy with an alpha-hero billionaire and a younger, sassy heroine, Looking For Trouble is must-read workplace romance. Cyrus is the notorious businessman and Presley is the grad student who not only finds herself in his class but also working with/for him. There’s an instant attraction between the two, but of course nothing should happen, and they both try not to let anything come of their desires. However, when things eventually escalate and turn into much more than they were looking for, will they be able to navigate what’s happening or are all the reasons they shouldn’t be together too much to ignore?

Cyrus Gates exactly the devilishly yummy alpha I was hoping for. The occasionally arrogant businessman has that tough-guy thing going on, but it’s not without reason, and I enjoyed finding out his backstory. Then there’s Presley, and she’s every bit the sweet and slightly naïve younger woman that’s strong enough to handle Cyrus. These two together were downright combustible, and their characters were great together.

The storyline flowed well, too. Not only was there the tension between Cyrus and Presley, but there was also everything happening workwise that kept the book interesting in a way that propelled what was happening between the main characters. All throughout, there was a good mix of spicy romance and a concurrent conflict occurring within Cyrus’ business dealings, which lent an extra level of complexity.

This is another win in Winter’s Chicago Billionaires series. It’s got plenty of heat and a compelling storyline between the characters, and I recommend it for your next workplace romance read.
Profile Image for Natalie Clarke.
Author 12 books44 followers
August 17, 2023
❤️LOOKING FOR TROUBLE ❤️

“I don’t want you to hold back with me. I want you to be the filthiest”—I pull her panties to the side as I begin to tease her—“little slut you want to be with me. There’s zero judgment.”
Her lips part, her thighs falling open a little wider as I begin to leisurely pump a finger in and out of her. “Can you do that for daddy?”

...

Oh my good God... Cyrus is one hot daddy! He's powerful, possessive, dominant and demanding and oh so sexy! He's an forty-something, dirty-talking billionaire with the body of a Greek God and the arrogance to match. No woman last longer than one night, until he meets Presley.

After a brief interaction in a bar one night, Presley is shell shocked to find the very same man stood at the front of her Ethics class as her new guest Professor. And after landing her dream job at a top PR firm, her annoyingly handsome, older Professor is now her new client.

The attraction between them gets too much, and despite agreeing that their relationship would be nothing more than physical, it's no surprise to either of them that it soon becomes more for them both.

...

You need a very rough”—he tugs my hair when says the word—“reminder of who the fuck you fell in love with.”

...

I was engrossed in this story and I loved that Presley brings out Cyrus' softer side and is not afraid to stand up to him and call him out on his BS. And bonus star for having her call him Daddy. 🥵👌🤤

I thoroughly enjoyed this story and I will soon be diving into the next one!

...

I was done looking for trouble the second I met you… because I finally found it.”


❤️❤️❤️❤️❤️
1,631 reviews13 followers
March 13, 2023
Spectacular steamy Chicago Billionaire romance, age gap with a touch of intrigue
Another romance where the anticipation of the inevitable makes for a thigh-clinching wait. Hot cover! Ms. Winter has written some Off. The. Charts. scenes between 46yo Cyrus and almost 25yo Presley. Some of the very provocative scenes go on for delicious pages. But there is a really good plot and ending here too.
Cyrus and Presley have a chance meeting in a bar one night where she is a bit argumentative with him. After a situation he is forced to call in a PR firm to help him improve his reputation which in turn will save a new deal; one solution is to have him teach an adjunct college graduate course on ethics of all things at his former alma mater. There sits none other than Presley in a Master’s course. She recognizes him immediately but he, not so much. Of course, we know what happens next or some semblance of it but whoa, the trip Ms. Winter takes us on will be unforgettable. There will be back-stabbing, embarrassing and fist-pump moments. This is a well-written page-turner romance.
I truly loved this book; great series. I like that Ms. Winter made Cyrus a wealthy but unfortunate character, a loner until he met Presley. If you like age-gap, billionaire, feisty-female and grumpy-male romance with lots of hot moments, you will want to read this book. Guaranteed! I volunteered to review an ARC of it through Booksprout.
Profile Image for Korkoi.
6,982 reviews31 followers
March 12, 2023
When Love Struck, There Was No Going Back -
Cyrus didn’t do relationships and also lived his personal and professional lives with an ‘I don’t give a frick’ attitude. However, all that changed when it had the potential to affect the business deal he was working on. The last thing on Presley’s mind during the final term to finish her degree was men, which meant her life was solely about finishing her degree and working.

However, once they started working together, the sexual tension built to an extent that it started affecting their daily lives. Unfortunately, even though they really enjoyed the continuous flirting, they couldn’t pursue a relationship, as there were potential consequences that could immensely impact their lives. However, after they went their separate ways, Cyrus realised what was more important in his life and decided to fight for a forever happiness with Presley.

I knew I was going to enjoy this book, because I was sucked into the story right from the beginning and I didn’t take a break until I finished reading it. I went through so many emotions as I turned the pages, but by the time I reached the end, I was really happy. This is a definite must read book, that you will be happy you read.

I received a free copy of this book via Booksprout and I am voluntarily leaving a review.
1,215 reviews5 followers
March 16, 2023
Cyrus Gates is a billionaire who runs his own company. He is well-known in the business world, he is older, bold, dynamic, intelligent, unafraid and he doesn’t take crap from anybody. Oh, did I mention he is very handsome. Presley is a grad student in her last semester of college. She is intelligent, a thinker, a work in progress as she explores the business world but also gorgeous, sexy, hot. Presley had a short discussion with Cyrus at a restaurant covering business ethics. She walks into her ethics class and who is her teacher - Cyrus, visiting professor. Cyrus feels an attraction to her. He challenges her and Presley feels a little intimidated by him but she is not afraid to challenge him back. Cyrus and Presley feel the attraction to each other but Cyrus will not allow anything to happen. She is too young for him and he doesn’t do relationships. He doesn’t do love - he has no heart. It’s really an emotional roller coaster ride with these two. Up down around backwards forward it makes the story so amazing! Such passion, such conflicted feelings and such a tangled emotional mess. They must feel it? Dynamic, complex characters and well developed storyline. This book will take you on a wild, crazy journey to something wonderful. Really a great read!.

I received a free copy of this book via Booksprout and am voluntarily leaving a review.
Profile Image for Bookmom1213.
430 reviews8 followers
April 13, 2023
Cyrus is a CEO. He always did what he wanted and didn’t care what people thought. He did keep people at an arms length though. Now he is older his billionaire playboy days are behind him. He is trying to buy struggling company and they are using his past against him. Upon the suggestion of his lawyer he hired a PR firm. She recommend that he teaches a class on business ethics at his University of Chicago, where he had graduated from. This will help his image.
Presley is in her last semester of her Grad school. She came to Chicago wanting to get out of her shell and live a little. But the entire time she has been at the university she has not been able to break through her shell. She was at a bar and over heard Cyrus talking to the bartender. When she didn’t agree what what he said she told him. He basically told her that he was not a good man. Two weeks later when he walked into her business ethics class as the professor she was shocked.
After class she reminded him who she is and they had met before. He hasn’t forgotten about the woman at the bar. He was intrigued to say the least. With his help she got a job at a PR firm. Now he is her client. After he warned her multiple times to stay away from him she couldn’t and he could get her out of his mind. She liked flirting with him. He wanted to punish her for behaving bratty and she is loving it.
I really enjoyed this book. I couldn’t put it down. Alexis knows how to write a book.
Profile Image for thebeespot72.
1,707 reviews183 followers
June 22, 2023
So Shame On Me Now...

🔥BOOK REVIEW: LOOKING FOR TROUBLE BY ALEXIS WINTERS🔥
RATING: ⭐️⭐️⭐️⭐️⭐️

Ooooh, girl. Let.me.tell.you! If you haven’t read an Alexis Winter book yet, you must start NOW! It’s as if she read my mind and put everything in one book. Big age gap, teacher/student, boss/employee, h@nd necklaces, sqü!r†!ñg, tøys, d@ddy/gøød g!rl. Have I got your attention? At one point, he tells her he will put a cøll@r on her. I could go on, but y’all need to read “Looking for Trouble.”

When twenty-five-year-old graduate student Presley has the opportunity to not only intern for Cyrus Gates, the 46-year-old billionaire and CEO of his own prestigious company, she takes it. Presley helps Cyrus improve his public image as they grow closer together. The more time they spend together they recognize their attraction and work out an agreement. Presley is interested in exploring s£xü@lly since she lacks experience, and Cyrus is happy to give her that. They neither anticipate the deeper feelings they develop for each other nor how what goes unspoken can impact any relationship’s potential.

I loved “Looking for Trouble” so much after reading it on KU that I had to purchase it to have it on my Kindle permanently — that’s how good it is!
Profile Image for Megan Horne.
109 reviews
August 19, 2025
Let me start by saying that the daddy kink/calling your boyfriend/husband daddy is not my personal preference for my real life. But I don’t yuck other people’s yum. And let’s be real it makes for some amazing books lol.

The book was so good! I was hooked from the start! The 3rd act breakup was done well! It was what Cyrus needed as a wake up call to face his fears and what he thought he needed. I also think it did Presley good to think she wanted to break away from Chicago only to realize she was running and it wasn’t really what she wanted.

The banter! Oh the banter was soo good!! I enjoyed the push and pull of their relationship and the gradual progression of it while there was a lot of fighting their true feelings.

There was only one real thing that seemed to bother me and that was in regard to Presley’s parents ages and when they had her. There was a part where she said that they had issues with getting pregnant - took 10 years. She said they were older when they had her. But if you follow the other parts she says that they are only 2 years older than Cyrus, which means they were only early 20s when they had her. So if it took 10 years…. That means they were trying when they were like 13ish?!?
1,248 reviews
March 5, 2023
Another great book from Alexis Winter's "Chicago Billionaires" series.
Cyrus Gates and Presley James shouldn't work on so many levels but somehow they do.
Cyrus is two decades older than Presley, he has issues resulting from his childhood, he has a reputation for being ruthless in business and having hook ups with eye candy half his age, Oh, and not forgetting dating a colleagues wife..........but all was not as it seemed.
Presley James was about to finish college, she had a brilliant future ahead of her, she shouldn't have been attracted to Cyrus, he was much older than her, he was her professor and he was a client of the prestigious firm where she had a part time job.
This story follows the roller coaster romance of Presley and Cyrus, the palpable chemistry between them, his attempts to keep her at arms length to prevent ruining her future and his business, the flirty banter between them and the barriers that one by one fall down. This pair face soaring passion, ecstasy, misery and heartbreak before they find their HEA.
This is a lovely, emotional, age difference romance.
I received a free copy of this book and my review is voluntary,
Profile Image for Rebecca Unsworth.
160 reviews3 followers
March 13, 2023
Looking For Trouble is a standalone novel from the Chicago Billionaire series. It is a forbidden age-gap romance and features Cyrus and Presley. They first meet in a bar and there is instant attraction but Cyrus is a typical Billionaire with a reputation he is trying to clean up so nothing happens. He then takes on the job of a professor and meets Presley again in his class. Cyrus tries to stay away as not only is she younger than him but now she's also his student, but then Presley gets hired by a PR firm that handles Cyrus and they end up working closely together. Neither one of them want to do anything that will ruin each others career but they can't stay away.

Another fantastic story from Alexis, she writes great characters. I love how opposites they were originally, him being a powerful Billionaire who has closed his heart off and scandal seems to follow him around where as Presley is the sweet innocent ray of sunshine but they work so well together. If age gap romance with a dash of grump/sunshine and professor/student trope is your thing you will enjoy this.

I received a free copy of this book via Booksprout and am voluntarily leaving a review.
2,122 reviews7 followers
March 20, 2023
Cyrus Gates is a billionaire in Chicago. A deal he’s been working on for two years may collapse because of a morality clause. He has to fix his image. His long time friend Lisa Wade runs her own public relations firm and she is helping Cyrus with his image. She makes him accept a teaching position at his alma mater, the University of Chicago. He is going to teach the Business Ethics class.

Presley James is a from a small farming town 3 hours south of Chicago. She moved to Chicago for college. She is in her last semester of graduate school for public relations. Presley meets Cyrus at a bar where she questions his ethics. Little does she know that she will end up one month later is his Business Ethics course.

Presley loses her part time job at the same time that Lisa loses one of her publicists. Cyrus recommends that Lisa interview Presley. Lisa hires Presley and her assignment is working with Cyrus on his image.

What happens when Presley has to attend a charity gala with Cyrus? Can they keep their interactions strictly professional? Who ends up betraying Cyrus?.

I received a free copy of this book via Booksprout and am voluntarily leaving a review.
Profile Image for Jd.
651 reviews3 followers
May 4, 2023
This is more of a 4.5 star book, only because at times I wsh the pace would pick up. I can say though that Alexis Winter can bring the slow angsty burn.
Cyrus knows what he wants, but tries to fight it as long as he can. It is when Presley ups the flirtation that he finally gives in to his desire. He teaches Presley what it is to be sexually satisfied and free. Oh my goodness the things that he says to her.
Cyrus:“I know it hurts, baby, but daddy needs to fuck you now. I can’t hold back any longer.”

Although he is strong and has harden himself from what others think about him, he has a vulnerability that is not seen until he falls for Presley, but feels that he can not have her. He sees himself as a naughty man who cannot be good.
Cyrus:" I tilt my chin down and kiss the top of her head, a tear threatening to fall from the corner of my eye. My chest burns. "
Presley is a good girl who wants to be free of her mental restraints and becone a naughty girl.
The book ends with a nice HEA.
708 reviews16 followers
March 14, 2023
Cyrus is a walking scandal. He is a heartless billionaire. Cyrus needs a PR firm to help get the contract signed with Meridian. Meridian doesn’t like the way Cyrus gets business; ie blackmail. They don’t like how Cyrus conducts his personal life in the media. Cyrus meets Presley in a bar and she tells him like it is. Four weeks later Cyrus is the professor of Ethics in Business and Presley is one of his students. The tension between Cyrus and Presley is explosive. Cyrus gets Presley a job at the PR firm he uses and she then becomes his handler. Will Presley be able to clean up Cyrus’ image in order for him to sign the contract with Meridian? Will Presley fall for Cyrus while helping him? Will Cyrus find a way to not be a cold blooded man? Will Cyrus and Presley overcome their obstacles to get a life together? Will Cyrus and Presley find a happy ever after together?
I voluntarily reviewed an Advanced Reader Copy of this book via Booksprout.
1,371 reviews11 followers
March 21, 2023
Cyrus is a billionaire, he needs to improve his image for a business deal so his publicist advises him to take up a job offer to teach a class at his old university.
While there he meets Presley, one of his students and also a women he met previously and was attracted to.
There is an instant attraction to them, even though Presley also shows her dislike of how he does business.
Presley has always been the good girl and has wanted to break out of that mould for years but hasn't found a way to do it until she is offered a job with the PR company representing Cyrus.
When she ends with him as her client, it remains hard for them to keep their attraction hidden. But will this only ever be about sex between them or could Cyrus actually find himself admitting to being in love with Presley.


I enjoyed reading this book and would recommend it.

I received a free copy of this book via Booksprout and am voluntarily leaving a review.
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