• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Sinner

Sinner

I can't wait for graduation next week, a grown ass woman shouldn't need to endure how these women treat the students here, I swear they are even harder on me, than the rest of them. Although I and my family were surprised they would take me in- a catholic school. I guess in some way, because of the new Pope, they think they are progressive, the place is far from the city, and we pretty much only have weekends to go to town, and whatever. I'm not even Catholic, I'm not even a woman... well I am a woman, just not all the way yet...I'm...trans. I've been trying to make it through all of this without being scared, like the Catholic comedians joke about, most of which renounced their religion, and the things I hear from other people.

All I want to do is graduate, go to college, maybe get a nice job with a nice loft either downtown Velocity, or something in Stonewall. I'm not immoral, I'm perfectly sane, with a good head on my shoulders, I don't want to be brainwashed in to some sort of prude, but I swear this one Nun has it out for me, especially if I'm doing something "I'm not supposed to do as a young lady," like if she catches me looking at some of the other students, "a certain way." I've been able to skirt past her a lot, play things off, try to stay in her good graces. I think they've gotten to her, she's in her early thirties, acts like some, I don't even know. She has a thing for capital punishment, and revels in it, she even has a room for it, and I don't know if Priest even knows about it, or just looks the other way.

She always tries to tell me, she's trying to put me in the right path, punishment is the perfect negative reinforcement, I really screwed up a few days ago, I should've waited till I got back to my room, but I couldn't. The bad girls were being bad, it was after senior gym, we all have to shower in the locker room. The bad girls are the ones who are actually gay, and bi, you can tell, because they are the ones with the shower curtains open, doing...things. Somehow my soap bar (body wash was Satan's idea, blah!) ended up out of my stall, when I dropped it. I went to get it; some bad girls caught my eye. I know I'm supposed to hate my... my...thingy, but I get horny, the first chance I have to give it away, I'm there, but in times of need, its sure convenience, and I'm not gonna let it keep me from an orgasm, cause it's in the way. Here we go; the bad girls were doing bad things, I like girls, love guys, like girls for things other than dating. I was hard as fuck when one of them moaned and quivered when she cummed.

I was lost in fantasy as each one rinsed off, did their thing, and staggered out. I stroked myself nice and slow, peaking through my curtain, the soap made it so much better, my nipple rubbing on the wet tile threshold. I was lost in fantasy thinking about what could do to these girls, with or without this thing, I closed my eyes, stroking harder. I didn't hear the sound of Nun-loafers walking around, making sure all the girls were out of the shower, not making God cry or something. I was so close, I was about to bust... until the curtain was thrown open. There she was, Sister Kathy, erection lost, I lost it so fast, I thought it turned into a vagina, until she threw my towel at me, and of all things, grabbed me by my balls, pulled me from the shower, skated me down the hall, I mean it was like whoosh, straight to her little torture chamber. I remember it verbatim.

"I'm sorry, Sister Kathy, you know I don't mean to do it," I said.

"Don't give me that, you gave into temptation again, you know better than that," she said snatching my towel, looking me up and down, with that judging Catholic grimace.

I didn't know what I was in store for, masturbating is one thing, to the same sex is like the ultimate heresy to this people, I just stood there dripping as she lit a cigarette, starting on her tirade.

"Young lady, I told you about doing such sins, from falling asleep in class, and mass of all places, over waxing the floors, and generally being unlady like," she exhaled smoke. "You are eighteen, a young woman...aren't you...that's what you want to be, right?"

"Yes, sister Kathy, I wanna be a woman, I am a woman," I spoke.

She walked over with that cigarette just barely dangling from her mouth, she clutched my...thing...my cock; "You want to be a woman, then you shouldn't ever touch this devils penis," she shook it hard.

Here I am standing here with some woman holding my soapy junk, like exhibit A, squeezing it, my knees still want to buckle from the first time, my eyes... I can't give her the satisfaction of crying. She yanked me over to a dresser, pulling out some sort of harness. She told me to step in to it, fastened the adjuster tight around my waist, snapping the leg hole things, I thought it was one of those jock underwear things the gay guys wear. cigarette smoke wafting in to my face, she put this one weird strap around my balls, kicking my leg out for clearance, pulled them behind me locking them to the leg hole straps, I think she stretched them. She bunched up my cock in to this little sack- locking it in place, only the head poked out, and kinda down.

"Time to teach you a little self-control, you little gutter snipe," she said laying me on some sort of table.

"What are you gonna do to me, I promise I won't touch it again," I begged.

"Silence yourself, sound travels in this old building," she snapped.

"Why do you have this... whatever it is, did you buy it to punish me, Sister Kathy," I wondered.

"Actually it belongs to the priest, enough talking," She ordered with a smack on my wet ass.

She snatched me by my hair long enough to clamp down a board with little vices on it, I figured that out quick, before I could scream, she gagged my mouth, tightened a nipple to a vice as hard as she could, my arms and legs shackled down to bare my weight. I felt her drop ashes on my back, glancing behind me, I caught sight of her holding the prized cherry oak paddle, filled with holes.

"Now, child, let me teach you manners on being a lady," she said with a smack.

She smacked the hell out of my still dripping ass, I lurched against the vices, screaming through the gag. She went on and on:

"Ladies are not to be promiscuous," she smacked again.

"Ladies are to be polite, and respectful," she smacked again.

"Ladies ...should...never...have...a...dick," she smacked after every word, I felt a lump in my throat.

I tried to scream and beg after every smack, I wanted to pull away, every smack knocked me forward, my ass burned, my tits yanked against the vices... and my dick, my dick was getting hard, I started crying. I don't know what she was doing after she stopped, I kinda didn't want her to.

"I'm not sure if you understood that, did you learn your lesson," she asked. I tried to respond, but she said I was mumbling, so I obviously didn't.

I could feel her hand gliding over my burning ass, until one more smack, this one grazed my balls, sending shear pain, making my dick jump.

"Oh, I hit your balls, did I, they should be tucked up inside like a real woman," she whispered in my ear.

Then I felt something odd, she took them in her mouth, her tongue moving around them, I was so horny, tears ran down my face as my dick fought the restraint, I couldn't stop it. Her tongue slowly made its way to my hole, I've never had my ass ate before, hell, I've never had sex before. I couldn't be still, I flinched and wiggled, my tits were so sore, and red, every pull made me even hornier, every stab of her tongue, made me hornier. My dick pushing against the restraint, gave me much pleasurable pain. She dug her nails in my cheeks as she ate, she stopped.

"Child, you need to be still," she ordered with a swift smack the paddle.

Again, lurched forward, tits pulled, ass burning, dick in so much pain... tears... of... joy. She went to stick her fingers in me, to open me up, I would not, and did not want to be still, I wanted to be spanked.

She asked if I had learned my lesson yet, I shook my head "no," I heard the pleasure in her voice when she said; "good."

I was purposefully pulling against the vices as I heard her footsteps fade and return, before I knew it, a long hard dildo was shoved up my ass. In and out, in and out, she twisted, turned, and had it in all sorts of angles. She took the paddle, smacking my ass, shoving it as deep as it'd go with every hit. My dick throbbed, I knew I was precumming, she got all the right spots, making me cum hard, jacking off is a sin, compared to this. She walked off again.

I heard the strike of a lighter, my tits were freed, I was unshackled, ordered to turn over, I couldn't, she snatched me by my hair, smoke ran across my face, demanding I turn over. I mustered the strength to do so, my ass caught fire as it pressed on the table, I cupped my nearly purpled tits with slight relief.

"I didn't say you could touch yourself, did you forget why you were here," she asked rhetorically.

She had her robe removed, God, she was blessed, her nipples rock hard, wearing nothing... but a strap on, her headdress, and those awful shoes. She freed my dick, I wanted to touch it so bad. She tied up my tits, spread my legs, and guided her red phallic symbol of power in me. She pulled the ropes, with every thrust, they got tighter and tighter. I lost count of how many times I came, I had to touch myself, I had to do something, I ran my fingers through my hair, I sucked on them, I said fuck it, I snatched off the gag, grabbed my tits, and screamed; "Sister Kathy, punish me, for I have sinned," she yanked out her red phallic symbol of power, leaving my hole gaped open, as I gasp for air.

"Are you going to touch yourself again," she asked.

"No, Sister Kathy," I gasped.

"Are you sure, you won't do it again," she asked.

"I am a lady, a lady doesn't do such things," I cried.

She took a long drag on her cigarette.

"Sister Kathy, a woman should not pleasure herself, please Sister Kathy, give me release," I begged. "Only you can do it."

She looked at me, smiled, grabbed my aching dick, squeezing it hard, stroking it, the pain felt oh so awesome, she looked at my begging eyes, took me in to her mouth, balls deep until I came. Sweet heavens, I exploded, I held that table for dear life, my ass clenched up tight, my voice was gone. She pulled up nearly choking on my nut, still stroking me as I spurted her face. She ordered me to lick it off, spitting it in my mouth. Once I was free to go, I couldn't wait for my next fuck up.

The rest of the year is just flying by. I think the Father is going to get rid of her at the end of the year, because I'm her new favorite. Maybe we can get that loft in downtown Velocity.

"Miss Knowles, it's almost time to get off the computer," Sister Kathy said.

"Yes, Sister Kathy... Sister Kathy," Sarah started.

"What is it, child," Sister Kathy asked.

"I've been having impure thoughts again..." Sarah replied.

"Come with me, now," Sister Kathy smiled.

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Sinner

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 429 milliseconds