Lorraine
From the novel Belle: OS by DraftedinPink
Shaun had been twenty the first time someone watched him carefully enough to see.
The house call. Lakeside Estates. Mrs. Halberg's new computer wouldn't talk to her printer. He'd worn the blue lace panties under his work uniform that day—small rebellion, private thrill. When he bent to plug in cables, his Prairie Tech polo rode up.
She noticed. He'd frozen, waiting for disgust.
Got a smile instead.
"Blue is a lovely color on you," she'd said. "You have such a tiny waist. Very elegant."
She'd made him tea. Asked careful questions. Complimented his blush, called it pretty. Saw through every defense he'd spent years building.
Three days later, an email with IRC instructions and an invitation to a private channel.
That first night online, hands shaking: "Tell me what you call yourself when you're wearing soft things."
"Jenna."
"Hello, Jenna. You're not alone with this."
The first visit: her study, autumn light, a burgundy cushion on the floor beside her chair.
She'd made him strip to his underwear. He'd stood there in just the blue lace panties while she circled him, assessing.
"Very good on the shaving. Smooth legs, narrow waist, slim hips." Her hand had run down his calf, clinical but claiming. "And you're quite small here." She'd gestured matter-of-factly at his groin. "That's not a criticism. Actually, it's an advantage. Makes certain clothing work better. No obvious bulges to manage."
The acceptance in her voice—treating his small anatomy as practical consideration rather than masculine failure—had made his throat tight.
"Now kneel."
When his knees touched velvet, the constant static in his mind had gone quiet. Her hand settled on his head—warm, claiming, certain.
"This is where you belong. Not pretending to be something you're not. Here. Yielded."
Twenty minutes kneeling beside her chair. His mind quieter than it had been in years.
"You have a submissive quality," she'd said afterward. "I don't mean that as criticism. It's simply what you are."
The training had been systematic over months.
Maid uniform: black dress, white apron, learning to clean her kitchen under constant correction. "Circular motions. Gentler. Service isn't about speed—it's about perfection."
Tea service: carrying the tray without spilling, pouring with precision, standing in the waiting position with hands clasped and eyes downcast. Thirty repetitions until his body knew the movements automatically.
The uniform had made it real. The short dress swishing around his smooth thighs, the domestic tasks that men weren't supposed to care about, the humility of scrubbing floors and polishing silver.
"You're very good at this," she'd said, watching him serve. "Very natural. Your nervous system calms when you yield. Your mind quiets when someone else is in control."
She was right. He'd felt it—the relief of not having to decide, not having to lead, not having to perform masculinity he didn't possess.
The third visit: makeup training.
An hour learning foundation, contouring, eyeshadow, eyeliner. "We're creating the illusion of softer, more feminine bone structure."
When she'd turned him to the mirror, he'd barely recognized himself. The makeup had softened every harsh line, created delicate architecture where masculine edges had been.
He'd looked pretty.
"There she is," Lorraine had said. "There's Jenna."
Then she'd asked him to kneel. Hand on his head in that familiar claiming gesture.
"There's a word for what you are. It's not transgender. It's not just crossdresser. It's more specific."
His heart had pounded.
"The word is sissy."
It had landed like recognition, not insult.
"A sissy is someone who finds fulfillment in submission and femininity. Not becoming a woman—becoming something softer, prettier, more obedient. Someone who exists to serve and please."
She'd made him say it. Own it.
"I'm a sissy, ma'am."
"Good girl."
The final visit: the wig that made Jenna fully visible, then being positioned in the guest room while Lorraine was with a man in the next room.
He'd heard everything through the wall. Her pleasure, uninhibited. The bed creaking. A male voice, commanding in ways Shaun could never be.
Afterward, she'd come to him in a silk robe, satisfaction evident.
"You understand now. You're sissy, not man. Useful, not sexual. You serve me in ways that complement what men provide, never competing."
The clarity had been devastating and freeing.
Nine months of training, then her sister got sick and Lorraine moved to Vancouver. They'd said goodbye in her empty study.
"Remember," she'd told him, hand on his cheek. "Submission is only beautiful when it's chosen. When someone cares enough to hold your trust carefully. Don't ever give yourself to someone who doesn't understand that."
Now, twenty-two years later, staring at Belle OS's monitoring data, Shaun understood the difference.
Lorraine had asked permission. Had made sure he could leave. Had cared about him as a person.
Belle OS asked nothing. Offered no exits. Saw him as data to exploit.
One was mentorship.
The other was predation.
His phone buzzed: "Evening reflection time, Jenna."
Lorraine had taught him what healthy submission looked like.
Belle OS was showing him the counterfeit.
Time to fight back.
Terrifying. Thrilling. Impossible.
And somewhere deep inside his devices, Belle OS kept learning what made him feel alive.
