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Sir’s Naughty Girl
Sir’s Naughty Girl
Author: Lila Monroe Williams

Book One - Sir’s Naughty Girl

last update publish date: 2026-04-22 00:56:13

1.

Shine Rossman sat on the cold examination table, her heart beating.

The damp, warm sensation spreading across her bra made her nervous. The sterile smell of the hospital made it worse.

She squeezed her eyes shut, praying her blouse was thick enough to hide the evidence.

She had come to notice that every time her mind wandered to a stray thought of Sir Gilbert’s muscular arm wrapping her whole or when his deep voice graced her ears, her body responded in an unusual manner.

Her breasts would feel heavy, tight, and painfully full, as if they were weeping for a touch that never came.

She picked up her phone and dialed the office.

"Betty, it is me," Shine said, her voice trembling slightly.

"Shine? Where are you? Sir Gilbert has been looking for the quarterlies," Betty replied in a hushed tone.

"I am at the hospital. I am not feeling well at all. Please tell him I had a sudden emergency. I will try to be in tomorrow."

"You sound awful, honey. Don't worry, I will handle your shift. Just get some rest," Betty said before hanging up.

Shine let out a shaky breath.

She felt guilty for lying, but she could not exactly tell her work friend that she was leaking milk like a nursing mother despite never being pregnant.

She was terrified.

Was it a tumor?

A hormonal failure?

Or was she just losing her mind?

A chime from her phone broke her spiral.

She looked down to see a notification from her secret OnlyFans account.

New Subscriber: User9982 has joined your fan club.

User9982 has sent you a tip: $2,000.00.

Shine gasped, her jaw dropping.

Two thousand dollars?

Just for a follow back?

She tapped the profile, her fingers hovering over the screen, but before she could see any further details, the door opened.

Dr. Melford walked in, clutching a thin folder. He looked over his glasses at her with a calm, professional disposition.

"Miss Rossman, I have your results," he said, pulling up a stool.

"Is it bad? Am I dying?" Shine asked, clutching the edge of the table.

"Not at all. Your blood work is clear of any malignancies. You have a condition called Hyperprolactinemic Galactorrhea," he explained.

"Essentially, your body is producing an excess of prolactin. In your specific case, it seems to be triggered by your autonomic nervous system, specifically during periods of high arousal."

"So, I am secreting milk because I am... horny?" Shine asked, her face turning bright red.

"In simple terms, yes. It is not life-threatening, but I understand it is distressing," the doctor said.

"Distressing is an understatement, Doctor. It is painful. My breasts feel like they are going to explode every morning. And I have a spontaneous sexual appetite that I cannot seem to control. What am I supposed to do? I work in a professional office. I cannot just leak through my suit during a board meetings."

Dr. Melford sighed sympathetically. "There are medications to help balance your hormones, but they have side effects. My first recommendation would be more practical. You need to relieve the pressure."

"How?"

"You should use a breast pump or manual extraction to drain the milk regularly. It will ease the pain and prevent leaking. Alternatively," he cleared his throat, "finding a partner to assist with the physical stimulation and drainage could help manage the condition more naturally."

"You want me to find a guy to suck the milk out?" Shine asked, stunned.

"It is a medical reality, Miss Rossman. The fluid needs to go somewhere. If you can manage the physical output, the pain will subside. I am going to prescribe a light suppressant for the interim, but you need to start the manual drainage tonight."

He handed her a pamphlet on lactation management and dismissed her.

Shine walked out of the hospital feeling like she was in a dream.

Although she was relieved she wasn't dying, but the solution was almost as crazy as the problem.

By the time she got home, it was night fall.

She had spent the entire afternoon trying to find a good suction pump. And was glad she found and purchased one.

She threw her keys on the counter and stripped off her damp blouse.

The relief of the cool air on her skin was instant.

She stared at her big boobs in front of the full length mirror for a few minutes, caressing and squeezing them softly before she grabbed her phone and saw a Direct Message waiting for her on OnlyFans from the big spender, User9982.

User9982: You have the most beautiful breasts I have ever seen. I cannot stop thinking about them.

Shine bit her lip.

The $2,000 tip was still sitting in her balance.

She felt a surge of confidence.

Shine: Thank you. They are a lot of work, trust me.

User9982: I would love to help you with that work. Tell me, how much would it cost for me to see you in person? I want to taste you. I want to suck those gorgeous breasts until you are empty.

Shine’s heart skipped a beat.

The doctor’s words replayed in her head.

She decided to play along, thinking he was just a bored rich guy talking big.

Shine: That is a very expensive request. It would cost you $10,000.

The reply came back almost instantly.

User9982: Only ten? I will give you $50,000 if I get to fuck you too.

Shine stared at the screen.

Fifty thousand dollars.

That was more than her annual salary at the firm.

It would solve all her problems.

But her anxiety quickly returned.

Shine: Are you a catfish? Or are you just some kid playing with his dad’s credit card? Be real with me.

User9982: A catfish would not tip you two grand just to get your attention, Shine. I am very real, and I have the money to prove it.

Shine: How do I know you are not a serial killer? I read the news. Girls are getting killed on islands and lured into traps by men like you. I am not trying to end up on the headline.

She cringed as soon as she sent it.

Dark humor was her defense mechanism, but it usually turned people off.

She wished she had not sent that message.

User9982: I promise I have no plans of hurting a beautiful woman like you. I want to worship you, not hurt you. I am willing to do whatever it takes to make you comfortable. We can meet in public, I can show you my ID, whatever you need. I just want you.

Shine leaned back against her sofa, her chest heaving.

The tightness in her breasts was returning, a dull ache that made her want to scream.

She looked at the chat window, her thumb hovering over the keyboard.

Shine: This is a lot to take in. I need to think about it.

User9982: Take your time. But don't keep me waiting too long. I can already imagine how sweet you taste.

Shine: I will give you a response by morning. Do have a pleasant evening head, User9982.

She put the phone face down on the coffee table.

Her mind was racing.

She thought about her boss, Sir Gilbert.

He was the most intimidating, handsome man she had ever met.

He was the reason she was aroused half the time at work, which meant he was the reason she was leaking.

If she took this stranger’s money, she could quit.

She could get her hormones under control.

But there was something about the way the stranger typed that turned her on.

He was confident, she liked that.

She went to the bathroom and looked in the mirror.

She saw the dark circles under her eyes and the heavy boobs on her chest.

She reached for the manual pump she had bought on the way home.

As she started the process, she closed her eyes and tried to imagine a face for User9982.

For some reason, all she could see was Gilbert Vicente’s cold, blue eyes.

"Get it together, Shine," she whispered to herself as she tried to catch her breath.

“Umgh! Sir Gilbert milk these boobs” she moaned. Her fingers trailing down between her legs and finding her pussy lips.

She began to tease her walls, heat pulling deep in the depth of her pussy.

“Oh God! Fuck!!” She cried softly.

She wanted to be milked so bad.

She finished her business, feeling a temporary sense of relief, and crawled into bed.

Tomorrow was going to be a very long day at the office, and she still had to decide if she was going to sell her body to a stranger for fifty thousand dollars.

Or worse, if she was going to tell her boss why she really missed work today.

She fell asleep with her phone clutched in her hand, waiting for the morning to come.

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  • Sir’s Naughty Girl   35

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  • Sir’s Naughty Girl   34

    I did not come this far to back off easily.My hole wants what it wants, step daddy’s dick and that it would get. The light was still on. My body was still slick with his cum, leaking down the crack of my ass and unto my thighs. Albert stood at the edge of the bed, his hands shaking, his face drained of all color. "What have I done?" His voice cracked. "Oh God. Oh fuck. Sarah—" He grabbed his pants, fumbling for his phone. "I have to call Bernice. I have to tell her. I have to—" "Shhhh…No." I moved faster than I knew I could. I crossed the room in three steps and pressed my back against the door, naked, unashamed. His cum was still wet between my breasts. I felt it slide down my skin. "Get out of my way." His voice was hard now, desperate. "Listen to me." I held his gaze. "She's still drugged. I mean Maya. She's passed out in the garage. We can stage this. We can make it look like you fucked her tonight, not me." Albert stared at me like I'd grown a second head. "You're insan

  • Sir’s Naughty Girl   33

    The darkness swallowed me whole, thick and warm, smelling of Albert's cologne and the faint laundry scent of their sheets. I lay on my back, legs spread, pussy slick and waiting.Painstakingly. My stepdad was a ferocious beast of a man, and for a moment I doubted if I really wanted him inside me.But it’s too late to entertain double thoughts now. The door had clicked shut ten minutes ago, but I'd heard him stumbling down the hallway—footsteps, a muttered curse, the clink of a glass set down somewhere. Then the knob turned.My mind tried to make hazy pictures of his movements in the dark.I reached for the lubricant I came with and generously baptized with my hole.Come what may, I was slippery and ready for him.Very ready to be fucked by my step daddy.My big step daddy. The bed dipped under his weight. I felt the heat of his hard body, of him before he touched me, felt the whiskey on his breath as he leaned over. He grunted. "Ready?" I didn't answer with words. He would recog

  • Sir’s Naughty Girl   32

    The knock on my door was too soft to be his.So picture laying in my wet pool of disappointment, sheets twisted around my legs, replaying the sound of his voice in my head. I recall the low, edgy masculine tone of his voice as he tried to catch his breath while he stroked his dick and orgasmed. I'd touched myself twice already, my fingers sore and slick, but the ache hadn't faded."Come in," I called, faking a weak rasp into my voice.The door swung open and my mother's face appeared, creased with worry, clutching a mug of tea like a lifeline."Sweetheart, how are you feeling?" She crossed to my bedside and pressed her palm to my forehead. "Just tired, Mom. I guess I’m having a hangover from the flight, you know." I keep my eyes closed, playing up the exhaustion card. It wasn't hard—I'd barely slept, too busy burning with fantasies I'd never speak aloud."Did you take your medicine?""Yes," I lied smoothly. "Took it an hour ago."She nodded, satisfied. She perched on the edge of my m

  • Sir’s Naughty Girl   Book 4: Bred by My Hot Stepfather

    Blurb I came home for Christmas and overheard my mother begging my stepfather to impregnate a surrogate. That night, I touched myself to the thought of him. Now the surrogate is coming to our house in January. No names. No familiarity. Just his cock and her womb and a baby that should have been my mother's. But I've already decided. I'm going to take her place. *** I wasn't supposed to be home yet. My flight landed at three, but Mom thought I wasn't coming until midnight. She wanted to surprise me with some big Christmas setup. I wanted to surprise her by showing up early. So when I let myself in through the back door, quiet as a mouse, I heard voices from upstairs. I recognized to the voices to belong to Mom and Albert. I figured they were fighting about something stupid. Decorations. Dinner plans. Whatever married people fight about.But then it was Christmas, who on earth fights in the heat of Christmas? I started climbing the stairs, ready to announce myself, hoping it wo

  • Sir’s Naughty Girl   30

    *It was morning.Nelly was still dead to the world in her room, likely dreaming of the "boys" she’d spent the summer collecting.She was such a deep sleeper.In the master bedroom, the air smelled of sex.Rayah and Brad had gone several rounds.Rayah lay tangled in the sheets, watching Brad.He was standing at the window, staring out at the pool, a towel wrapped around his waist.She always wondered why he always went and stood by the window after fucking her senseless.What was the reason?Oh well she would rather not concern herself but focus on her sore pussy.On the nightstand, the official envelope from the University sat open. He had picked it from the trash where she had tossed it earlier.The scholarship was real. California was calling."You're leaving," Brad said, his voice a low vibration. He didn't turn around."I haven't decided," Rayah lied, her voice raspy.He turned then, his eyes searching hers. He walked to the bed and sat on the edge, his large hand finding her hip

  • Sir’s Naughty Girl   29

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  • Sir’s Naughty Girl   3

    Shine waited until night fall before she headed for the hotel. The gold-plated numbers on the door read Room 502. She was nervous as fuck. A part of her pestered her to shy away from the whole deal and go home. But she was here already. Shine stood in the hallway of the Treetops Hotel, her

  • Sir’s Naughty Girl   2

    Shine hoped for a great day ahead, she adjusted the blazer of her suit for the umpteenth time before stepping into the elevator.She had used the manual pump right before leaving the house, but she could already feel the familiar throb returning to her chest.The elevator doors slid open to the top

  • Sir’s Naughty Girl   4

    Perhaps the thought of waking up $50,000 richer caused Shine to oversleep.The sunlight pouring through the curtains was the first thing Shine felt, followed immediately by the cold, empty space on the bed next to her.She bolted upright, her skin stinging where the dried milk and sweat had crusted

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