All characters are 18 or older. This collection of stories is set at St. Benedict’s and can be read in any order. Categories will vary from story to story as appropriate.

This story contains MtF trans content.

St Benedict’s is a rich kid boarding school where lost-cause rich kids go to be babysat. They are bad students and grades don’t matter. The teachers and staff are equally bad, with low expectations.

The unofficial motto is: “Where rebels thrive and trouble is the norm”

Nurse Polly Simmons

OMG, my jaw is sore. Nick Smith had just jammed his sizable cock in my mouth and fucked my face. I’m the school nurse at St Benedict’s. I do the normal things like first aid for cuts and scrapes. But I also take care of the sexual health of some of the students.

“See you next week, Nurse. Take care of that mouth.”

“Yes, Nick. It’ll be ready for you.” I kept my eyes down, unable to look him in the eye.

“Good girl, Nurse.”

I looked out into the waiting room. Tim Matthews was waiting patiently, reading a textbook. He was always studying. I don’t know why he was stuck in this school, with all the other losers. Hopefully, he’d make something of himself.

“Tim, just a minute, okay.”

He looked up and smiled at me. “Sure thing, Nurse.”

I straightened my scrubs and washed my face. Nick liked to be rough. He would hold my head and fuck my face until he came down my throat.

“Tim, come in.”

I got him settled on the exam table, “Now what seems to be the issue?”

“You know, Nurse Polly, just here for my weekly checkup.” He grinned as he said it. We both knew what he meant, but I always make him say it.

I started by pulling down his johnny. He’s no athlete, but he’s in decent shape. His sandy blond hair hangs in bangs just over his eyes.

My hands ran along his chest. Of all the boys at St Benedict’s, Tim is the only one who doesn’t take advantage of me. He’s the only one I wouldn’t mind taking advantage of me. The others do it because I’m timid and they know they can get away with it.

He pulled me in for a hug. I feel safe in his arms. His hands slide down over my butt and squeezed the cheeks. I’m short and slender, but my ass is my pride and joy. I’ve climbed millions of steps to work my 26-year-old booty.

“I’ve been thinking of your ass all week. Are you ready for me to fill you up? Do you want my hard cock inside you? Stretching your tight little sphincter while I stroke your little dick?

“Oh Tim, you know I want that. You are the only one I let near my butt.” I hugged him back as he palmed my ass cheeks. His hands rhythmically squeezed them, pulling them apart. My little butthole tensed each time he separated them.

He stood up and knelt, his face at my crotch. He pulled my scrub pants down, leaving my boy shorts. The small bulge of my penis pressed against the silky material of my panties. My dick was never very big; a little under average size for a man.

He rubbed it through my panties. “I love your little dick, Polly. It’s so cute.” Slowly, he pulled the boy shorts down my legs.

His tongue licked all over, caressing the head, and slurping along the shaft. I was rock hard now, tiny compared to him. He sucked me in his mouth, and the whole thing easily fit, not like his cock in my mouth. His nose was tickling my pubes. He caressed my balls, holding the smooth bag.

He bobbed up and down on me for several minutes. His tongue was driving me wild, bringing me ever closer to orgasm. “Tim, I’m close.”

He pulled his mouth off and smiled. “Not yet my love.”

I moaned in frustration at his tease. I felt like I’d cum if he so much as breathed on my dick.

He stood and pulled his pants down. His glorious cock jutted out. I love his cock. Not too long, but nice and thick. I could just fit my hand around it

He bent me over the exam table. My ass and dick were hanging over the edge. I was still hard, but the urgency to cum had lessened. Tim tongued my starfish, licking at it. I love how he was tender with me. Not like the other students who used me as a fuck toy to be discarded when they got their rocks off.