Penelope Sky Books in Order (Updated April 14, 2026)

Penelope Sky writes dark romance in connected clusters of trilogies and longer runs, so the real question is not just “what comes first?” but also “how far does this continuity stretch?” For most readers, the safest answer is to begin with Buttons and Lace, then move through the larger catalog in the author’s own preferred series sequence.

This guide keeps the boundaries clear. Main series are listed in reading order, alternate titles are noted where they matter, and every book gets a one-line continuity note so you can see what each step is doing before you commit.

Quick answer

Start with Buttons and Lace (2016).

Then read series in this order:

1. Buttons
2. Queen
3. Beyond Buttons
4. Banker
5. Skull
6. Wolf
7. Betrothed
8. Chateau
9. Cult
10. Lesser
11. Empire
12. Betrayal
13. Fifth Republic
14. Roman Republic

That is the best all-catalog route for a new reader because it follows Penelope Sky’s own preferred series path and keeps later relationship arcs from arriving without context.

How to use this list

Read each series straight through before moving on. Penelope Sky’s books are not all one single continuous saga, but they do work best when you respect the internal order of each run and then move to the next series in the broader sequence.

I have not treated box sets as separate entries, and I have not added a novella section because the main verified reading structure is built around the core novels and retitled editions rather than a stable novella track.

Recommended reading order by series

Buttons

Included. Best starting point for almost everyone.

1. Buttons and Lace (2016): The opening novel introduces the dark power dynamic and emotional framework that make this the clearest first stop in Penelope Sky’s catalog.
2. Buttons and Hate (2017): The central conflict sharpens as the relationship turns more volatile and the series begins defining its longer emotional arc.
3. Buttons and Pain (2017): The middle of the series raises the personal cost of every choice and pushes the original setup into harder territory.
4. Buttons and Shame (2017): The fallout expands the story beyond the initial premise and deepens the pressure on both leads.
5. Buttons and Blame (2017): The series moves toward resolution while forcing its characters to confront consequence, loyalty, and control more directly.
6. Buttons and Grace (2017): The final book closes the main Buttons arc and gives the series its last major turn before later connected books pick up adjacent threads.

Queen

Included. Also known in older listings as the Scotch series.

1. The Scotch King (2017): This opens a new trilogy with a fresh central pairing while staying in the dark-romance lane that connects naturally after Buttons.
2. The Scotch Queen (2017): The second book tightens the relationship struggle and turns the trilogy toward its emotional and strategic midpoint.
3. The Scotch Royals (2017): The trilogy finale resolves the Queen arc and works best read before moving into the larger Beyond Buttons run.

Beyond Buttons

Included. Frequently listed under alternate “Buttons and …” titles.

1. Muse in Lingerie (2018): This begins the long follow-on sequence that expands the world after Buttons and shifts attention to the next major romantic arc.
2. Beauty in Lingerie (2018): The second book settles the new pairing into a more dangerous and emotionally layered conflict.
3. Lady in Lingerie (2018): The series starts widening its supporting cast and continuity weight while continuing the central relationship thread.
4. Queen in Lingerie (2018): This installment pushes status, control, and long-term loyalty further into the foreground.
5. Empress in Lingerie (2018): The emotional stakes keep climbing as the series leans harder into dominance, resistance, and consequence.
6. Fantasy in Lingerie (2018): The arc broadens again, using its length to deepen character ties rather than resetting the story.
7. Desire in Lingerie (2018): This book keeps the momentum going by escalating attachment and conflict at the same time.
8. Sassy in Lingerie (2018): The tone sharpens here, but it still functions mainly as a direct continuation rather than a side detour.
9. Divine in Lingerie (2018): The series moves into its later phase, where emotional payoff depends on having read the earlier books in order.
10. Foxy in Lingerie (2018): This entry continues the long-form progression and is best read without breaks because the character dynamics are cumulative.
11. Fine in Lingerie (2018): The story narrows back toward payoff, drawing on the tension built across the earlier installments.
12. Princess in Lingerie (2018): The series begins steering its many developments toward an endgame structure.
13. Dancer in Lingerie (2018): This late-volume entry matters most as continuity setup for the final stretch of the run.
14. Fighter in Lingerie (2018): The penultimate book intensifies the final conflicts and leaves little room for out-of-order reading.
15. Lover in Lingerie (2018): The last book completes the Beyond Buttons arc and closes one of the longest connected runs in the catalog.

Banker

Included. A compact trilogy and a good secondary entry point if you want a shorter commitment.

1. The Banker (2019): This opens a fresh trilogy built around power, money, and control, with a more contained setup than the longer earlier runs.
2. The Dictator (2019): The second book hardens the central conflict and pushes the trilogy further into its imbalance-of-power theme.
3. The Tyrant (2019): The finale completes the Banker arc and delivers the trilogy’s final answer to its control-versus-attachment tension.

Skull

Included. Read after Banker in the preferred sequence.

1. The Skull King (2019): This starts another dark-romance trilogy with a new dominant figure and a fresh central relationship structure.
2. The Skull Crusher (2019): The middle book raises the pressure and turns the trilogy’s attraction into a more dangerous entanglement.
3. The Skull Ruler (2019): The final volume resolves the Skull trilogy and lands best when read immediately after the first two books.

Wolf

Included. Another short, direct trilogy.

1. The Wolf and the Sheep (2019): The opening book sets up a predator-prey style dynamic that defines the trilogy’s tone from the first installment.
2. The Wolf and His Wife (2019): The relationship shifts from pursuit to possession, changing the conflict without abandoning the original tension.
3. The Lone Wolf (2019): The trilogy closes by reworking the same core dynamic into its final emotional and narrative form.

Betrothed

Included. A long run that should be read straight through.

1. Wife (2019): This opens the Betrothed sequence with a marriage-centered premise that immediately signals a longer, layered relationship arc.
2. Husband (2019): The second book builds directly on the opening arrangement and starts showing where the bond will complicate.
3. Lover (2020): The emotional framing widens here as the series begins moving beyond title-level roles into deeper attachment.
4. Committed (2020): This installment reinforces that Betrothed is built as a cumulative run, not a set of loosely related standalones.
5. First (2020): The story enters a more extended middle phase where earlier choices begin shaping later stakes.
6. Second (2020): This continues the same progression, developing continuity rather than resetting the premise.
7. Forever (2020): The title signals a longer-view emotional turn, with the series leaning harder into permanence and consequence.
8. Lie (2020): The arc darkens again here, using deception as a pressure point inside the already established bond.
9. Secret (2020): This near-final entry concentrates on withheld truth and the damage it can do late in a long-running arc.
10. Truth (2020): The final book closes Betrothed by bringing its relationship and secrecy themes to their clearest resolution.

Chateau

Included. A four-book sequence that comes after Betrothed in the preferred order.

1. The Chateau (2020): This begins a new setting-driven arc with a contained backdrop that still fits naturally into Penelope Sky’s larger dark-romance style.
2. The Camp (2021): The second book changes the immediate environment while keeping the series tightly locked to its central conflict.
3. The Boss (2021): Authority and control move even closer to the center as the arc heads into its final phase.
4. The Palace (2021): The closing volume completes the Chateau sequence and gives the four-book run its final payoff.

Cult

Included. Short and easy to place because it is only two books.

1. The Cult (2021): This opens a more enclosed and threatening setup, with the title itself signaling the kind of control structure the story will explore.
2. The Catacombs (2021): The second book completes the arc and functions as a direct continuation rather than a separate branch.

Lesser

Included. A compact trilogy that follows Cult.

1. Lesser Evil (2022): This begins a morally shaded trilogy where the central tension depends on blurred lines rather than simple innocence or guilt.
2. Better Man (2022): The second book shifts attention toward change, worthiness, and whether the lead can become more than his earlier role suggests.
3. Harder Betrayal (2022): The finale closes the trilogy by making betrayal the final test of everything the first two books built.

Empire

Included. A short two-book sequence.

1. Bartholomew (2023): This starts the Empire arc with a character-centered title that suggests a more personality-driven entry into the series.
2. Barbarian (2023): The second book completes the duology and works as the closing answer to the power dynamic introduced in the opener.

Betrayal

Included. A six-book 2024 run.

1. It Kills Me (2024): This begins the Betrayal series by framing emotional damage as the engine of the story from page one.
2. It Breaks Me (2024): The second book intensifies the same wound-driven arc and pushes the damage deeper rather than wider.
3. It Ruins Me (2024): The middle stretch becomes more destructive here, making the title progression feel deliberate rather than decorative.
4. It Hurts Me (2024): This installment keeps the focus on sustained emotional fallout and personal cost.
5. It Pains Me (2024): The penultimate book extends the suffering-and-endurance pattern before the series reaches its last turn.
6. It Destroys Me (2024): The finale delivers the darkest title in the sequence and closes the six-book arc at its most extreme point.

Fifth Republic

Included. A three-book 2025 sequence.

1. The Butcher (2025): This starts the series with a forceful character title that signals a harsher and more dangerous power center.
2. The Carver (2025): The second book continues the same brutal naming pattern and deepens the trilogy’s menace.
3. The Saint (2025): The finale closes the Fifth Republic trilogy with a title that suggests contrast, irony, or transformation at the end of the arc.

Roman Republic

Included. The latest fully listed Penelope Sky series as of April 14, 2026.

1. The Ruler (2026): This opens the newest currently listed trilogy and sets up another authority-focused dark-romance arc.
2. The Savage (2026): The second book escalates the tone by shifting from rule to raw force in the trilogy’s middle stage.
3. The Breaker (2026): The third book completes the currently listed Roman Republic run and is the latest published Penelope Sky title shown in the verified catalog.

Alternate titles and naming notes

The Queen trilogy is commonly listed under older titles: Protect Your Queen, Love Your Queen, and Worship Your Queen. Those correspond to The Scotch King, The Scotch Queen, and The Scotch Royals.

The Beyond Buttons books are also commonly listed under alternate “Buttons and …” titles. The reading order does not change, but the naming can make the catalog look larger or more confusing than it really is if you are comparing retailer pages, review sites, and series databases.

Best starting points by reader type

1. Start with Buttons and Lace if you want the most reliable first book and the clearest path into the wider catalog.
2. Start with The Banker if you want a shorter trilogy before deciding whether to commit to the bigger reading universe.
3. Start with The Ruler only if you specifically want the newest currently listed Penelope Sky sequence and do not mind beginning far downstream from the original entry point.

Do you need publication order?

Not really. For Penelope Sky, strict publication order matters less than series order plus preferred cross-series order. The books are better navigated by continuity blocks than by a master date list, especially because some series also carry alternate titles that can make publication checklists look messier than the actual reading experience.

Final recommendation

For almost everyone, the right move is simple: begin with Buttons and Lace, finish Buttons, and then keep going through the series in Penelope Sky’s preferred order. That route gives you the cleanest progression, the least confusion around retitled books, and the strongest sense of how her connected dark-romance catalog develops over time.