Lilly Lustwood's Blog, page 2
August 2, 2025
Femboy’s First Love – Transgender Transformation Romance
“Why do you like me? I’m not even a girl… yet.”
Close your eyes, give me your hand, darling.
I didn’t mean to cause drama—I just said yes to a role no girl wanted. A cigarette-twirling, fishnet-wearing streetwalker in the school play. But one photo. One whisper. One jealous cheerleader named Venice Fletcher—and suddenly Monty Hiddleston in a corset became everyone’s favorite gossip.
The bullying came fast. Louder. Crueler.
But so did Kristoff Hilton. He stood up for me when no one else did. Held the umbrella when I got soaked in the rain. Sat beside me when I didn’t have the words. And when I told him, “I’m not even a girl… yet”—he kissed me anyway.
Clutch your Pearl Necklace Tight and Prepare for a Transgender Romance Ride!
Note: This story contains transgender romance, transgender transformation, surprise feminization, friends to lovers, romantic comedy, crossdressing romance, and first-time feminization tropes. Some real places and people were referenced but the story is a work of fiction. The cover image is from Brightlucky Press.
July 26, 2025
She’s Inside Me – Transgender Transformation and Feminization Romance
“You only matter when you’re me, when you’re the hottest girl in the room.”
Close your eyes, give me your hand, darling.
They shoved me into lockers. Laughed at the way I walked. Called me names I pretended not to hear. I was Liam Whitmore—ghost-boy of the hallway. Until I started blacking out. Until she showed up.
Lexa wore crop tops under my hoodie. She stole Savannah’s lip gloss and kissed the jock. She was everything I wasn’t—bold, flirtatious, fearless.
She got me into trouble… but kept me alive.
Clutch your Pearl Necklace Tight and Prepare for a Transgender Romance Ride!
Note: This story contains dissociative identity disorder, transgender romance, psychological feminization, enemies to lovers, popular jock and loser, romantic comedy, crossdressing romance, and first-time feminization tropes. Some real places and people were referenced but the story is a work of fiction. The cover image is from Brightlucky Press.
Beauty School by Chance – First-time Feminization Romance
“Why did nobody tell me that LashTech isn’t about coding? I’m not here for beauty school!”
Close your eyes, give me your hand, darling.
I thought I was signing up for a coding bootcamp. LashTech & Laser Co. sounded techy enough. I showed up in cargo shorts, expecting JavaScript. Instead, I got dragged into a beauty school full of lashes, wigs, and hot pink chaos.
One makeover turned into full-time corsets, tucking tutorials, voice drills, and a whole new mirror I wasn’t ready to look into. But the more my instructor touched me—my cheekbones, my waist, my soul—the more I started wanting to stay.
Clutch your Pearl Necklace Tight and Prepare for a Transgender Romance Ride!
Note: This story contains transgender romance, transgender transformation, surprise feminization, friends to lovers, mentor and apprentice love, romantic comedy, crossdressing romance, and first-time feminization tropes. Some real places and people were referenced but the story is a work of fiction. The cover image is from Brightlucky Press.
July 11, 2025
Sissification Sisters – First-time Feminization Romance
“Win a Hottest Sissy competition to pay for my father’s debt!? Are you nuts?”
Close your eyes, give me your hand, darling.
I thought I was just another broke IT dropout with overdue bills and zero prospects—until a couple of thugs tossed me in the back of a van and dumped me into what they called a “debt-payment facility.”
Translation? A secret sissification camp run by loan sharks to pay for my late father’s gambling debt. Twelve guys. One year of luxury promised to the prettiest “girl.” One winner who’ll be clear of his debt forever. A billionaire bidder hiding behind a screen. Corsets, lip gloss, punishments, and challenges designed to break us—and reshape us.
I was ready to fight my way out. Until I met Riley. Smart-mouthed. Soft-eyed. Hacker. Hotter in panties than anyone had the right to be. We were supposed to compete. Instead, we helped each other survive. Tucked each other. Did each other’s makeup. Moaned together. Fell hard.
Clutch your Pearl Necklace Tight and Prepare for a Transgender Romance Ride!
Note: This story contains transgender romance, surprise feminization, friends to lovers, romantic comedy, crossdressing romance, and first-time feminization tropes. Some real places and people were referenced but the story is a work of fiction. The cover image is from Brightlucky Press.
July 6, 2025
My Girly Diet – Rapid Feminization and Transgender Transformation Romance
“He said it was a testosterone shake. But why was I growing boobs!?”
Close your eyes, give me your hand, darling.
I tried to sabotage a Pride march with a fake bomb threat. I thought I’d get away with it—until Noah Hart, the local co-op owner and ex-pharma genius, caught me red-handed with blue chalk on my fingers.
Instead of turning me in, he offered me a deal: taste-test his new ‘testosterone-rich’ smoothie line. Desperate to keep my job and reputation, I said yes. What I didn’t know? It wasn’t testosterone. Not even close.
The mirror changed. My thoughts changed. My body changed. Now I dream in lipstick. Tuck into bras. And every time Noah looks at me, I forget who I used to be—because the girl in the mirror looks nothing like the gym bro Colby.
She looks like Cleo.
Clutch your Pearl Necklace Tight and Prepare for a Transgender Romance Ride!
Note: This story contains transgender romance, rapid feminization, enemies to lovers, romantic comedy, crossdressing romance, and first time with a transgender woman tropes. Some real places and people were referenced but the story is a work of fiction. The cover image is from Brightlucky Press.
June 30, 2025
My Landlord’s Lipstick – Reluctant Feminization and Transgender Transformation
“He said I could stay in his house for free, but only if I wore THAT lipstick.”
Close your eyes, give me your hand, darling.
I got caught stealing from the cash register at the diner I worked at. Spent my last paycheck on gacha games. And somehow ended up living in a studio owned by a control freak named Gage.
His rules were taped to the mirror. Wear lipstick. No sweatpants. No excuses. Lotion daily. And on weekends? Femme attire required. I thought he was insane. But I was desperate. And maybe a little curious.
I didn’t expect the tucking tutorials. The shade called Girly Pink. The way he watched me, like I was both his punishment and obsession.
Clutch your Pearl Necklace Tight and Prepare for a Transgender Romance Ride!
Note: This story contains transgender romance, surprise feminization, enemies to lovers, alpha billionaire, romantic comedy, crossdressing romance, and first time with a transgender woman tropes. Some real places and people were referenced but the story is a work of fiction. The cover image is from Brightlucky Press.
June 22, 2025
The Sissy Assassin – Rapid Feminization and Transgender Romance
“I didn’t plan to get breast implants to kill a billionaire. But ten million dollars and a promise of a new life can definitely change someone’s mind—and body.”
Close your eyes, give me your hand, darling.
Thirty. Ex-con. With nowhere to go. I served seven years for killing the man who put my best friend in the grave. I didn’t cry. I didn’t beg. I kept my head down.
Then a handler in a perfect suit offered me a deal. One mission. A new identity. All I had to do was go undercover as a high-class escort named Maxine and infiltrate a global sex trafficking ring.
There were rules. Corset training. Lip gloss drills. Breast implants. I hated all of it… Until I didn’t.
Every time I looked in the mirror, Max slipped further away.
And Victor—the agent assigned to “manage” me—started looking at me like I wasn’t just bait… but his.
I never meant to fall for my handler. I never meant to become the girl I was pretending to be. And I definitely never meant to feel powerful in stilettos—with a pistol strapped to my thigh.
Clutch your Pearl Necklace Tight and Prepare for a Transgender Romance Ride!
This story contains transgender romance, gradual feminization, friends to lovers, suspense, romantic comedy, crossdressing romance, and first time with a transgender woman tropes. Some real places and people were referenced but the story is a work of fiction. The cover image is from Brightlucky Press.
June 16, 2025
Mascara and Military School – Feminization Romance and Transgender Transformation
“It was just a prank. I didn’t mean to get court-ordered into a girls-only military academy… or end up wearing a pleated skirt with a girly name.”
Close your eyes, give me your hand, darling.
I was Brady Lang. Seventeen. Smart mouth, bad grades, and one glitter-fueled fire too many. Instead of juvie, I got sent to Valkyrie Academy—except Valkyrie didn’t take boys. So my aunt made me into Bree. Quiet. Polished. Invisible.
Only, I didn’t stay invisible.
Not with Levi Knox—grumpy, gorgeous senior cadet—watching my every move. Not with skirts swishing around my legs, makeup softening my face, and something inside me aching every time someone called me she.
It was supposed to be fake.
But somewhere between drills and detentions, detangling my wig and losing my heart, I stopped pretending. And when Levi kissed me, I wasn’t just scared of being caught. I was scared… I didn’t want to go back.
Clutch your Pearl Necklace Tight and Prepare for a Transgender Romance Ride!
This story contains transgender romance, gradual feminization, enemies to lovers, bully romance, romantic comedy, crossdressing romance, and first time with a transgender woman tropes. Some real places and people were referenced but the story is a work of fiction. The cover image is from Brightlucky Press.
June 9, 2025
Digital Doll – First-time Feminization and Transgender Transformation
“I only wanted one selfie. I didn’t mean to break his iPad—or agree to pretend to be a girl online just to pay him back.”
Close your eyes, give me your hand, darling.
I was Luke Campbell. Nineteen. Invisible. A freshman with two brothers in college and a jock bully for a roommate. Then I shattered Dylan Myer’s brand-new iPad, and everything changed.
To pay him back, I became LuluStar22 on Cyber Darling—flirty, girly, and completely fake. At least, I thought it was fake. But every bralette, every swipe of gloss, every time I said “hi boys,”… something shifted. Especially when Dylan started looking at me differently. Softer. Protective. Like maybe he wasn’t seeing Luke at all anymore.
I never meant to keep dressing up after the stream ended. I never meant to feel more me as Lulu than I ever did as Luke.
And I definitely never meant to fall for the guy who blackmailed me.
Clutch your Pearl Necklace Tight and Prepare for a Transgender Romance Ride!
This story contains transgender romance, gradual feminization, enemies to lovers, bully romance, romantic comedy, crossdressing romance, and first time with a transgender woman tropes. Some real places and people were referenced but the story is a work of fiction. The cover image is from Brightlucky Press.
June 2, 2025
Insta Bride – Feminization Romance and Transgender Transformation
“I wasn’t even supposed to wear the dress. I was just delivering it. Then my boss zipped me in—and called me Delilah.”
Close your eyes, give me your hand, darling.
It was supposed to be a favor. A last-minute replacement for a bridal campaign shoot in Tuscany. I was Drew—an unpaid script assistant with shaky hands and zero modeling experience. But the gown fit.
The wig worked. And the billionaire groom they asked to pose beside me?
Yeah. He looked at me like I was real. Luca Feretti didn’t know I was lying. Not when he held my hand for the camera. Not when he kissed me under fairy lights. And definitely not when he told the world I was his girlfriend to help sell his family’s wedding estate.
I never meant to fall for him. I never meant for my secret to go viral. Now everyone knows. The photos, the press, the kiss—it was all supposed to be pretend.
Clutch your Pearl Necklace Tight and Prepare for a Transgender Romance Ride!
Note: This story contains transgender romance, rapid feminization, enemies to lovers, romantic comedy, crossdressing romance, and first time with a transgender woman tropes. Some real places and people were referenced but the story is a work of fiction. The cover image is from Brightlucky Press.
