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Standby for the Chicago Billionaires, a series of billionaire boss romances from Alexis Winter, featuring full-length standalone romances filled with a lot of steam. Be warned.

If you love dominant, filthy-talking billionaires then don’t hesitate to dive into these novels. Each book is an age-gap, billionaire office romance that will have you clutching the sheets and begging for more.

Chicago Billionaires Series Reading Order by Alexis Winter

Dirty Little Secret: A Billionaire Boss Romance (Chicago Billionaires Book 1 ) by Alexis Winter

I’m the type of man that gets what I want.
Hell, I didn’t become a billionaire before forty-five by playing by the rules.
But then she waltzed into my life…

Watching his PR Director, Wren, stare out of his office window, Theo can’t help but notice her beauty. Something he has always seen but it is growing harder and harder to ignore as time goes on. Checking in with her that everything is OK after her break up six months ago she confides that she is still getting calls and messages from Penn.

Throwing herself into her work, especially since ending things with Penn, Wren looks forward to relaxing at home. Still adjusting to living on her own she has been having some hot and heavy dreams about Theo – with so many reasons why she can never act upon them in real life. Yet it is Theo she turns to when she discovers that she is being followed.

Theo can’t believe that she has kept the knowledge that someone is following her to herself for the last few months. Moving her into his place they adjust to spending more time together. A work trip has them discussing more intimate topics and Theo confessing his dirty little secret but Wren doesn’t quite grasp which part was the secret. Heading back to their lives they drift between being friends and wanting more, but with her ex still hanging around will they ever have the chance to explore their feelings?

Those Three Words: A Single Dad Billionaire Boss Romance (Chicago Billionaires Book 2) by Alexis Winter

I never thought getting fired from my dream job would change my life.
And I certainly never imagined three little words would be my undoing.
Those three delicious, toe-curling words whispered by my boss.

The end of the school year and Margot should be looking forward to the summer. However, she has just been told that funding for her music program has been cut and she has been effectively fired. With only enough money to tide herself over for a month, she applies for a number of jobs as well as reaches out to parents for summer music lessons. Seeing an ad for a live-in nanny position matching her qualifications and teaching experience but she has never been a nanny before.

With his house manager on vacation, Graham finds himself urgently needing to fill the vacant nanny position. Unsure as to why Miss Perry didn’t hire someone before her holiday he finds Margot’s resume and hires her. Immediately attracted to her as soon as lays eyes on her. Whilst he has dealt with the grief from his wife’s death five years ago, he is overwhelmed by his feelings towards his daughter’s new nanny.

Pushing Graham to spend more time with Eleanor, Margot inserts herself into life at the Hayes house. Confuses by her reaction to Graham when he is near and touches her. They attempt to not act upon their attraction but it is palpable and soon they aren’t able to stop themselves. But how will they manage thoughts and comments from others?

Available to buy from Amazon in Paperback and Kindle Editions.

Just This Once: A Billionaire Boss Romance (Chicago Billionaires Book 3) by Alexis Winter

I swore to myself that I’d never cross that line with her.
But when Savannah Monroe, my chief operations officer, shows up on my doorstep with a proposition that starts with her in my lap and a promise of just this once…breaking the rules suddenly seems so enticing.

At fifteen years my junior and the smartest woman I’ve ever met, she’s by far the greatest asset at Baxley Tech.
From the moment I hired her, we had a connection—as friends, as a mentor.
A lingering touch.
A stolen glance.
An unspoken attraction that simmers just beneath the surface, threatening to boil over.

So when she reveals a painful secret she’s been hiding from me that involves my CFO, I don’t hesitate…I take care of it immediately.
Or so I thought.
But the lies and corruption go much deeper than I ever realized and now we’re in a tangled web of passion and secrecy.

After our one night together, everything changes.
The thought of her in the arms of another man turns me into someone I don’t recognize—insatiable, hungry.
Indulging in every filthy thought I’ve had about her for three years is one thing, but losing my heart in the process wasn’t part of the deal.

But here’s the thing about forbidden fantasies…they usually come at a price.
And this one, just might be deadly.

When a blackmailer threatens to destroy her life and everything she’s worked for, I take matters into my own hands.
Because when it comes to Savannah Monroe, there is no negotiation.
No backing down.
No Limits.
No Rules.
No losing her.

We promised each other it would only be just this once.
But now that I’ve had a taste…I want my fill.

Beg For It: A Billionaire Boss Romance (Chicago Billionaires Book 4) by Alexis Winter

You know that feeling—the one where you tell yourself it’s a terrible idea but you’re going to do it anyway?
Even though you know that this man isn’t just your father’s best friend who’s twenty years your senior…he’s your new boss.

If you asked Bronte Spencer a few years ago whether she would be attending a lavish graduation party organised by her father she would have said no way. Yet this is where she finds herself, having reconnected with her estranged father – one of her mom’s dying wishes a couple of years ago. It took Bronte two years to decide to see if she would be able to have a relationship with the man who was more absent than he was present. He is, however, attempting to make up for that with this party and an offer to work at his business. Not interested she takes the other option of working for his best friend.

Seeing a beautiful woman in the bar approaching him, Beckham Archer loves her flirty banter. Surprised to see her give him her name and number, even more so when he realised who she is and decides to up and leave the bar. The next day finds her in his office for the job he mentioned to her father, much to her surprise. Figuring a way to work together around the obvious attraction and somewhat awkwardness goes smoother than they anticipated but Bronte wants to pull the thread on whether had she not been the daughter of his best friends and whether they would have hooked up.

Blown away by her beauty and brains has Beckham questioning the path and things he wanted out of his life. Finding themselves giving in to the forbidden and hiding their connection from everyone, especially her father. Just as Bronte realises that she might be in over her head, Beckham received news from an ex that throws a spanner in the works. Unable to continue as they are, Bronte opts to walk away but will Beckham realise what he stands to lose?

Looking For Trouble: A Billionaire Boss Romance (Chicago Billionaires Book 5) by Alexis Winter

You know what they say about trouble…if you go looking for it, you’ll probably find it.
But I wasn’t looking—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 Chicago billionaire and my new professor.

Cyrus Gates is a hard-hitting Chicago billionaire, known for working hard to acquire other businesses, merge them or tear them apart. Going through a large merger at the moment he is struggling to see why his personal life is being brought up as a potential stumbling block. Blowing off steam he enjoys a drink in his favourite bar he discusses business practices with a beautiful young woman at the bar. needing to work on his public image away from beautiful women he enlists Lisa Wade as his PR team who lines up a professorship at the college.

Meeting Cyrus Gates in a bar a month ago did not go well for Presley as they disagree on business methods. Heading into her business ethics class at college she is surprised to find that it is Cyrus who will be the guest professor this semester – oh the irony! They get off to a bumpy start in classes as she expresses her thoughts on ethics and suggests that his ethics aren’t in line with hers. Cyrus clearly not remembering their previous meeting. Their interaction makes the spark between them ready to combust at any moment, Cyrus attempting to hold back on any desires he has for Presly but it appears that she is looking for trouble.

Overhearing a conversation about her losing her job Cyrus recommends Lisa’s firm which is looking for a new publicist. Landing the job Presley isn’t too sure how she will handle working with Cyrus but manages to get interviews and events lined up for him. Line blurring between professor/student, client/publicist they banter back and forth. Cyrus asserts his controlling nature especially when Presley doesn’t listen to what he says etc. But as deadlines loom, secrets are exposed, are they only a fling? Is the age gap too big to make this work?

Very Bad Things: A Billionaire Romance (Chicago Billionaires Book 6) by Alexis Winter

He said he wants to do bad things to me…very bad things.

The first time I met single dad Weston Vaughn, I thought it was my meet cute.
I was in Paris looking to start over and he was right in the path of my hot coffee.
But it turns out, my knight in shining armor was just a grumpy billionaire in a custom suit.

A few years ago Daphne Flowers lost her mom to cancer and just a few months later her fiance in an accident. Attempting to navigate life without either of them she has thrown herself into her work. She’d hoped to gain a job at an elite academy but has not heard anything so heads to Paris to reassess her life. Bumping into a handsome American their interaction doesn’t go too well. Thankfully a call about the job brightens her day.

Running late for his meet and greet with his daughter’s new first-grade teacher, Weston Vaughn is in for a surprise when it turns out to be the beauty from Paris. Immediately rubs her up the wrong way even though his daughter Daisy loves her. Reaching out to her to help with a last-minute babysitting issue he is pleased to see his daughter connect with someone as she is usually guarded around anyone other than family. Miss Flowers seeks him out to get him to volunteer alongside all the other parents they start to get on and chat during the event.

Their paths crossing, Daphne debates whether she should accept his offer to stay on his yacht with the family over Labor Day weekend. Giving in, they connect and the sparks fly, plus his friends with benefits are waiting in the wings to warn her away from him. But as secrets are revealed they step back but it appears that Weston has some deep-seated enemies. Can they figure out who is pulling the strings?

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