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A Key to the CEO's Heart

A Key to the CEO's Heart

“Since we are going to get you panties and stockings, I think we’re going to get some bras too, and some wobbly-bobbly silicone breast pads.” After paying for the clothes we fitted at the counter, we left the shop and went to the lingerie department. Victor dragged me all around the store choosing sets and sets of bras and panties, and eye fitting them on me right in front of all the ladies. Believe it or not, even if I agreed to do this crossdressing thing, I was still capable of feeling embarrassed. Really. Victor picked a few sets of them with laces he liked, which match with the clothes we bought earlier. He pulled me to the fitting room and I tried everything on again.
107.4K viewsCompletedAdded to Library 185 Times as stories about crossdressing
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The Pack's Rebels

The Pack's Rebels

“Concordian women have long worn trousers.” “Brought over from Estreau,” she pointed out, amused. “And other lands where the ideas of there being something appropriate for one person and something else for another dictated by whether they do or do not possess a c-ck has never been such as issue as it has been for the humans of Greibron and Alden. Harithen has embraced this concept with a fervency,” she continued. “I think it speaks to him, to his own relationship with his body and self.”
1066.4K viewsOngoingAdded to Library 1.3K Times as stories about crossdressing
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susanrae2011
I love, love, love this series!!! It's been an amazing ride, since the beginning, but idk what to do now... I'm so lost without my daily updates! Hopefully, the time flies and the next book is out before I even realize! ...... Thank you Everleigh for such an amazing series! I'll be counting the days!
Jackie
I started The Triquetra a while ago, got through a few chapters and stopped, the back n forth was annoying me, however a few weeks ago I started it again. I am now about to start packs dragon. The way these books have been written is brilliant Talen’s life was important to the story, so well written
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Goddesses or 49 ½ shades of charcoal

Goddesses or 49 ½ shades of charcoal

Abe’s only contribution was, ‘Enjoy yourselves now, but it isn’t going to happen. Cath ignored him and rubbed his face. ‘It’s smooth, but his hair is so dark on the white skin.’ ‘Let’s black him up.’ ‘It will have to be a long-sleeved dress and thick tights.’ Mave disappeared to the bathroom and came back with some waxing strips, waxing honey and a wax warmer. Things had reached farcical. I had to intervene. ‘Let’s try something else. I’m looking at some cross-dressing advice online. There is one picture here of a very hairy man in a short-sleeved, short dress, hair everywhere, bushes poking from under his décolleté.
3.8K viewsCompletedAdded to Library 102 Times as stories about crossdressing
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Married a Secret Billionaire

Married a Secret Billionaire

Instead, he tightly held her hand. "I... I have something else." He sobbed, "After you hear it, maybe you'll find it disgusting... My family is poor, and I had to start working early to support them. But being so peculiar, no one wanted to hire me. Then, I accidentally found that if I dressed in women's clothing and walked on this street, those perverted men would come looking for me... so I just..." Persephone froze, not knowing what he hadn't finished saying. But it probably wasn't something good.
9.91.2M viewsCompletedAdded to Library 34.7K Times as stories about crossdressing
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Mint Mocha
I've only read two books on this app. This is the second and by far the best one. The storylines are fluid, the characters are endowed with personality and most importantly the writer makes them come together seamlessly. Ideally, this is what the experience should be, uncomplicated and enjoyable.
Sharon
I like the story. However, the cost is high for books on here and they are never ending. Not that the chapters are long, but it is almost the same outlying as the other books from this author. Sometimes it takes a moment to see what characters they have actively engaged in that chapter.
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Unraveled Destinies

Unraveled Destinies

JANE'S POV “Hey Jane, can I come pick you up tonight? I ignored the message because I wasn't interested. Spicy was too extra and he made me laugh the entire time. He started telling me about how some guys tried to do him dirty because he was a crossdresser and how he fought all of them for self-defense. He demonstrated everything and I was laughing, forgetting that it wasn't a comedy show. He fixed the wig and when I added a glimpse of myself in the mirror, I was looking like a 24-year-old baddie. He started my make up and in no time we were done. I was taken to another room to pick out some selected outfits, and I fell in love with the first outfit I tried. I didn't take it off.
93.0K viewsCompletedAdded to Library 90 Times as stories about crossdressing
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Second Marriage to the Billionaire: Ex-Husband Begs Me Not to Go

Second Marriage to the Billionaire: Ex-Husband Begs Me Not to Go

“He had this online romance. Kept bragging about his gorgeous ‘girlfriend’ on the internet. And yeah, the guy really was gorgeous—because he was a cross-dresser. A cross-dresser with a girlfriend. He scammed Greenie here out of enough cash to bankroll that girlfriend’s life. So technically, our boy here ended up being the other man. A very generous one.” The whole room started snickering. Lucas laughed even harder. “But wait—it gets better. The guy actually fell for him. Said he was moved by his… spending power. They started dating for real. And the cross-dresser? Could fake a woman’s voice. So Greenie went on dates, totally clueless. Until one night, he got drunk, dragged to a hotel, and—we
8.843.1K viewsCompletedAdded to Library 1.3K Times as stories about crossdressing
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 Reborn Dragon Vein Warlock, talented beautiful mage

Reborn Dragon Vein Warlock, talented beautiful mage

"Cousin Christine, I just thought you were so beautiful and had such a perfect figure that if you tried on some clothes I could use that as an excuse to look, but that didn't happen." Under the "lie detection" spell, Olivia didn't dare hide anything. "I'm your cousin, how could you have such a lewd thought?" Olivia argued, "I couldn't help it, besides, I just wanted to take a peek, you wouldn't notice." Christine said word for word, "As a man, you're wearing women's clothes and looking at your cousin, can you give me an explanation? Cousin Audrey." Yes, no matter how you look at it, she is a beautiful young girl, but Olivia is a man, commonly known as a cross-dresser, and Christian found out
1.6K viewsOngoingAdded to Library 62 Times as stories about crossdressing
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Married at First Sight

Married at First Sight

It could be seen that she had successfully disguised herself as a man, deeply ingrained the image in people’s minds. The driver and the bodyguard both breathed a sigh of relief. After all, Mr. Hayden was clearly a man. Now, due to being in a same-sex relationship with Mr. Kevin, he cross-dressed for his sake. This was just a bit of romantic playfulness between couples. They could not bear to watch, but they had to. If someone said their boss was originally a woman, would that not imply they were all blind?
9.232.5M viewsOngoingAdded to Library 909.0K Times as stories about crossdressing
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Mia
Thus far the book ... was compelling but disappointed that there is no ending to the novel. I planned on reading another book after this but with this experience why would I since there might not be and ending to that one as well! Bummer! Please do better so you don’t loose customers in the future.
Terri West
I love Reading this book about Serenity and her husband it's amazing how her marriage at first sight really turns into her really fallen in love she wasn't looking for love just a place to stay and how tentive Zach was he had his guard up at first because he thought she was out to get his wealth wow
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Alpha's Dirty Secrets

Alpha's Dirty Secrets

I smiled letting my lust sneak through. "Hold on," Timothy grinned. I was in trouble. "When I helped Cáel move in I saw he had a huge box full of women's clothes - not in his size. He's not a cross dresser." Gee - thanks Timothy, you right bastard. "What is a cross dresser?" Aya piped up. I groaned. "A cross dresser is a man who dresses up like a woman," Nikita provided. "A Drag Queen is a man who dresses up like a famous woman/actress/singer. A transvestite is a man who dresses like a woman because they want to be a woman."
1011.5K viewsOngoingAdded to Library 264 Times as stories about crossdressing
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Read Stories About Crossdressing Novels & Stories Online

Here are 68 novels related to stories about crossdressing for you to read online. Generally, stories about crossdressing or similar novel stories can be found in various book genres such as Romance, Werewolf and Mystery/Thriller. Start your reading from A Key to the CEO's Heart at GoodNovel!

Frequently Asked Questions

One theme that shows up constantly is the 'secret life' situation—a character, often someone in a high-stakes professional or social position, who finds freedom and identity through dressing in clothing associated with another gender. It’s not just about the clothes; the tension comes from the risk of exposure and the contrast between their public facade and private truth. Something like 'My Boss is My...' or those CEO-office assistant setups in webnovels play with this beautifully, mixing workplace power dynamics with the vulnerability of a hidden self. The popularity probably stems from that dual fantasy: the thrill of a dangerous secret and the emotional release of finally expressing something fundamental that’s been suppressed.

Another massive category is the 'forced' or circumstantial cross-dressing plot, often for survival or a specific goal. Think a man hiding in a women’s convent, or needing to infiltrate an all-female space for protection or a mission. This setup automatically generates constant situational comedy and awkward intimacy. The 'one bed' trope gets amplified tenfold when one party is pretending to be something they’re not. Readers get the slow-burn realization from other characters, the accidental touches, the shared moments where the disguise almost slips. It’s less about internal identity exploration initially and more about external pressure, which makes the eventual emotional connection feel even more earned, like in some historical Chinese BL webnovels where a scholar has to pose as a courtesan.

I’ve noticed a real surge in stories where cross-dressing is the central mechanism for exploring gender fluidity in a fantastical or omegaverse setting. It’s not just a disguise; it’s a literal key to unlocking a different biological or social role. In omegaverse tales, an alpha might suppress their scent and pose as a beta or omega to avoid political marriage, leading to wild twists when their true nature erupts. The appeal here is the extreme externalization of internal conflict—biology itself becomes a character in the disguise. The themes get heavier, touching on societal expectation versus true nature, but wrapped in a high-drama package of scent-marking and possessive romance. It takes a familiar spicy trope and cranks it up by making the concealment a matter of life, death, and soulmates.

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