Spank or Treat: Halloween with the Headmaster, a short story

Halloween is for fun and fantasy. As a special treat for our readers this Halloween, twelve spanking fiction authors are presenting free short spanking stories and a chance for you to win some hot prizes including:

  • $50 gift certificate to blushing books
  • $25 gift certificate to Eden’s Fantasy 
  • Books, Amazon & BN gift certificates and many more prizes.

All you need to do to enter is answer the question posted on each of the twelve participating blogs and then sign up on Governing Ana.  Complete contest rules and prizes available are listed on Governing Ana. At the end of this blog, you’ll find a link to the other authors on the Spank or Treat blog hop. In addition to the above mentioned prizes, I’m having a drawing for a $10 Amazon gift certificate. To enter my individual drawing all you have to do is read the story and then answer a simple question. Be sure to post your email address so you can be contacted if you win. (Note: my Comments box/link is located at the end of the story where all the tags are.)

Halloween with the Headmaster is intended to be a lighthearted, somewhat tongue-in-cheek fantasy read. So just sit back and enjoy as Hallie experiences her best Halloween ever at Mrs. Bottom’s School for Girls…

Halloween with the Headmaster

by Cara Bristol

Lightning zigzagged across the night sky. Hallie squinted at the address she’d scribbled on her palm, then at a stone monument outside the massive house. Three five eight. Toilet paper obscured part of the first numeral in addition to some writing on the address marker.

Should she call to verify she had the right place?

No, Jack might get pissed. After last night, she wanted him happy. Her boyfriend complained she didn’t listen, didn’t pay attention. In actuality, the reverse was true. For six months, she’d hinted at what she needed, but he hadn’t picked up the cues.

When she had dredged the courage to confess, “Jack, I want to be spanked,” his reaction had been worse than she had feared. He’d stared at her like she was a bug under his feet. No, like a germ under the bug under his feet.

But the next day he’d called and told her to meet him.

“Are we going to a party?” She’d asked because it was Halloween, her most favorite holiday of the year.

“Yeah, a costume party,” he’d responded. So she’d dressed in her fantasy outfit. Now she wondered if he hadn’t been serious, but sarcastic. Was anything more embarrassing than showing up as the only person in costume?

Hallie pulled up her white knee socks that had slid to her ankles, then smoothed her hands over her white blouse and tugged at her plaid skirt.  Just go inside. She nudged herself up the walk and rapped the heavy brass knocker, shaped like a hand. Seconds later, the door was flung open.

A man stood in the large foyer underneath a huge crystal chandelier. Behind him, the floor tile, Italian marble perhaps, continued down a long corridor. Rooms, their doors shut, branched off. But she didn’t see any people.

She’d made a fool of herself again.

The man said nothing, but fixed a quizzical gaze on her face. Hallie wet her lips. “Uh, Jack gave me this address?”

“Do you have the invitation?”


“Password then.”


“I’m sorry miss, but this is a private party.”

“She’s my guest this evening.”

Another man stepped into the foyer from behind the massive wooden door.  Tall, though not excessively so, he carried authority in his posture and wide shoulders. A welcoming smile eased the intensity of his piercing brown eyes. He wore charcoal gray slacks and a white oxford, the sleeves rolled to the elbows.

“Very well.” The first guy allowed Hallie to enter, then shut the door and disappeared down the hall.

“I’m Con Harris.” Her rescuer’s gaze never strayed from her face, but Hallie got the impression he recorded every detail, down to the number of buttons on her blouse and the scuff on her black patent leather shoes.

“Hallie Blair. Uh, is Jack here yet?”

“There might be a Jack.” He nodded. “I tried to meet as many guests as I could, but I may have missed someone. What’s his fantasy?”

“Fantasy?” Hallie twisted her mouth. Jack’s idea of a fantasy would be missionary position sex with the lights on. “Uh, I wouldn’t know.”

“But yours is to attend Mrs. Bottom’s School for Girls.”

“Mrs. Who?” Hallie clutched the collar of her blouse. Crap. “I’m sorry. I have the wrong address.” She turned toward the door.

“You didn’t come to be spanked?”

Warmth of embarrassment flared to a raging bonfire of excitement. A wild beat drummed in her chest. Jack had listened to her! He did care. He didn’t want to spank her himself, but he’d set this up so she could get what she craved. Or maybe he would do it himself. That he would try it meant the world to her.

She executed a crisp turn. “Why, yes I did.”

“Allow me to escort you to your classroom then. You’ve already earned demerits for tardiness. This way, please.” He beckoned and headed down the corridor, empty of all furniture except a bench outside one of the closed rooms. “The password, by the way, is “Spank or Treat.’”

Spank or Treat? Spanking was a treat. Hallie’s Mary Janes tapped on the tiles. At the last door Con stopped and gestured for her to enter.

Nine women dressed similarly in plaid skirts and blouses sat at wooden desks while another in school marm garb paced and whooshed an elongated a ruler through the air. Behind her, a girl, the backs of her thighs reddened, wrote on a large blackboard, “I will not chew gum in class.”

“I found Miss Blair outside,” Con said. His voice had gone stern. “I’m taking this one on as a personal project. If she causes any trouble, send her to me.”

“Certainly, Headmaster.” The teacher nodded.

Headmaster? Hallie’s snapped her head around. He winked, momentarily breaking his disapproving expression, then exited the room.

“We’ll don’t just stand there gawking, take your seat!”

A woman giggled as Hallie scurried to the nearest desk.

“Perhaps you’d like to share the joke with the class?” The teacher turned a stern eye on the woman. Hallie wasn’t sure what was going on, but a rollercoaster feeling sped through her. This was the most fun thing to happen to her since…well…never.

“I’m sorry Mrs. Bottom.” The giggler hung her head, but her eyes gleamed.

“Front and center, now.”

The woman trotted to the head of the class.

“Over the desk.”

She didn’t even try to mask her smirk as she assumed the position, and her micro skirt rode up to reveal a tiny G-string.

Anticipation swelled, and Hallie held her breath.


Hallie jumped. A beautiful red mark streaked across a pale moon.

Repeatedly, Mrs. Bottom struck. A classmate moaned, a whimper of sexual longing to be that girl, a feeling that echoed deep inside Hallie. By the time the woman’s ass glowed evenly, Hallie had drenched her thong.

The woman returned to her seat, rubbing her bottom, a happy smile on her face. Envy burned like an ember in Hallie’s stomach. The woman scribbling on the chalkboard finished her lines and returned to her seat.

“And now, if there are no further interruptions, let us proceed. Miss Blair, please pass your term paper to the front.”

“Paper, ma’am?”

“On the War of 1812.”

Hallie wiggled in her seat. A quick study, she’d caught the gist of Mrs. Bottom’s School for Girls. Trying to look shamefaced, she said, “I’m afraid the dog ate my homework, Ma’am.” Please, please, spank me too.

Mrs. Bottom tightened her lips into a slash of crimson. “Since history isn’t your forte, we shall switch to English grammar. Please explain what a gerund is and give an example.

A gerund was an I-N-G verb that functioned as a noun. I need a spanking. “Uh, isn’t a gerund a small rodent?”

Her classmates tittered.

“Silence!” Mrs. Bottom snapped the ruler against her desk. “That is a gerbil, Miss Blair,” she said icily. It’s obvious you think this is a joke. You leave me no choice but to expel you—“

Hallie’s stomach plummeted to the soles of her black Mary Janes.

“—and send you to the headmaster. Perhaps he can correct your incorrigible behavior.”

Hallie intercepted the jealous glances of the other women, and her hopes soared.

Mrs. Bottom grabbed a pad from her desk and began to write. “Tardiness, ten demerits. Failure to turn in homework, twenty-five. Disrupting the class, another twenty-five.” She tore off the sheet. “Take this to the headmaster, two doors down on the left.”

Hallie scooted to the front and retrieved the paper. “Thank you, ma’am.”

“You won’t thank me after Mr. Harris is finished with you.”

Hallie gulped as fresh doubts arose. She’d entered a game in which she didn’t know the rules or the players. Maybe it wasn’t even a game to them. Who knew what could happen to her? But Jack had set this up. He wouldn’t send her into a situation that wasn’t safe.


“I’m very disappointed in you.” Con Harris removed a paddle from the wall of a formerly luxurious office that had been redecorated to appear stark, furnished only with a gray metal desk, a rolling chair behind it, and a hard wooden one in front of it.

Hallie clasped her hands behind her back. Anticipation jitterbugged inside, making it difficult to remain still. “I’ll try better, Sir.”

Con shook his head. “You realize this will go on your permanent record?”

It would certainly be indelibly recorded in her memory as the best Halloween ever.

Con settled onto the hard chair and patted his lap.

After a couple of false starts, Hallie laid herself across his knees and steadied herself with her palms against the floor. His thighs formed a hard surface beneath her stomach, which fluttered like a panicked bird. She’d bumped against  a different kind of hardness as she’d wiggled into place.

Con pressed his hand on her lower back. Her skin tingled underneath his palm.

“I’m going to lift your skirt.”

“All right.” This stranger would see her almost naked butt, but a shivery thrill trumped embarrassment. Finally.

Cool air caressed her skin.

Seconds later a satisfying fire glazed across her ass. She gasped. Another whack and delicious pain splintered across the other butt cheek.

“In the future you will be on time.” Smack. “Do your homework.” Smack. “And pay attention in class.” Smack.

Again and again the paddle fell.

She couldn’t help writhing and bucking with every searing, glorious blow. She relished it all, the feeling of helplessness, of his body shifting under hers, of the radiating burn that sharpened with each strike, the scold of his voice. She realized that even if Jack had performed the deed, it would have been awkward, nowhere near as wonderful.

She hoarded every spank to be savored later.

And then it ended. Con lifted her off his lap. Her ass throbbed, pulsing to a rhythm timed by her heartbeat. She dashed a trickle of wetness from her eyes with the back of her hand.

“Do you think you’ve learned your lesson?”

“Yes, Sir.”

“I’m not convinced. I believe that detention might be in order. You’ll report back for the next three Saturdays at 9 p.m. Of course, you’ll be paddled each time.”

She felt as a cork had popped from a bottle of champagne, and it bubbled inside her body. “Yes, Sir.” She nodded as meekly as she could.

“Wait outside my office, and I’ll see you to your car.”

Hallie winced as her ass connected with the hard bench. She couldn’t go back to Jack now. She knew him too well. He’d never allow her to return every Saturday to be spanked. He may have set this up, but probably he’d intended to teach her spanking wasn’t what it was cracked up to be. Except it was what it was cracked up to be. For the first time ever her hunger had been sated.

Her cell signaled the arrival of a text, and she peered at the screen.

Jack! How would she tell him? She opened his message.

Where the hell r u? Intended to tell u in person. This isn’t working 4 me. Sorry.

Meaning seeped into awareness. He broke up with me by text! She shook her head in disbelief at his crassness, but she felt relief rather than pain. Jack had never been right for her.

Con emerged from his office with a large black umbrella, and escorted her down the hall, cupping her elbow in a way that seemed almost possessive. “Did your fantasy live up to your expectations?”

“Exceeded them,” she answered.

He curved his lips into sexy grin. “Good, Mine too.” His smile slipped a little.  “This Jack that you mentioned, is he your boyfriend?”

“Ex,” she answered, so grateful it was true.

Con stopped her in the foyer. “I’m not supposed to ask you, but…”  He glanced around and then continued in a low voice, “Would it be okay if I called you?”

“I’d like that.”

Outside, a misty rain filled the night sky with sweetness Con held the umbrella over their heads. Water had washed the toilet paper from the sign on the lawn.

American Discipline Association, it read. Five Five Eight. Hallie laughed.


Question: “Schoolgirl” is Hallie’s fantasy Halloween costume. What is yours? Post your answer to enter the drawing for my $10 gift certificate to Amazon or Barnes & Noble (winner’s choice), then visit the other participating blogs and Governing Ana to read more spanking stories and enter the drawing for the grand prizes. Contest ends at midnight EST October 31.

Claire Collinsgrove                          Alice Dark                             Patty Devlin

Emma K. Gardner                           Celeste Jones                        Starla Kaye

Sue Lyndon                                      Constance Masters              Renee Rose

Rollin                                                 Anatasia Vitsky 

Sign up for the grand prizes here


Update: Attention all Spank or Treaters! If you were erroneously charged for Jade Cary’s To Love a Woman or Alta Hensley’s Traditional Love, Lazy Day will be reversing the charges. You need to register (free) as a member, sign in, and then “purchase” the book. Don’t forget to enter “spankortreat” as the promo code. Both books will be free today!


My published spanking stories: Unexpected Consequences, False Pretenses, Spanked!

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34 Responses to Spank or Treat: Halloween with the Headmaster, a short story

  1. Great story, Cara. Thanks.

    I have to go with schoolgirl too on the costume.

    Darn…only 11 stories left.

  2. Loved the story! I have to go with the schoolgirl costume as well.

  3. Oh…yum. Yum yum yum. This is brilliant, and I laughed in delight at the password! Clever. My fantasy costume would be…gosh, there are so many! Schoolgirl is certainly one, especially an Edwardian or Victorian one. Ballet dancer.

  4. Alisha says:

    This is a common fantasy for me. Loved this story!! I read there are to be more stories!! I didn’t realize there were any scheduled at all. This story is going to make tonight very fun and somewhat painful. Lol. I’m on vacation and hubby brought his “tools!” Awesome story!!

  5. Sue Lyndon says:

    What a fun, sexy story! I love a schoolgirl costume…oh and naughty maid outfits are nice too:)

  6. Thianna D says:

    Woo hoo!

    That was a great Spank or Treat story! Can I go to that school? *grins* Loved it!

    Hmm, as for what is my favorite costume, I love to wear a prim librarian outfit. *Grins*

  7. Loved it. What a fun way to spend Halloween! I love school girl outfits.

  8. pao says:

    I enjoyed the story, especially the classroom scene! Um, fantasy costume? Pirate with a proper tricorn hat. Though the ultimate fantasy would be a stormtrooper costume 🙂

  9. SH says:

    Great story! I would have to say the school girl costume would be my choice.

  10. Minelle says:

    Great story…
    My favorite costume would be something like a sexy saloon girl, can can type.

  11. bn100 says:

    I like a witch costume.

  12. Ann Q says:

    No school girl for me, I would like to be ZEENA WARRIOR PRINCESS.

  13. His First Mate says:

    Last year I went as a naughty nun. I don’t know about fantasy costume but this year I FINALLY convinced The Captain to go as The Flinstones! I make a fantastic Wilma with my red hair!

  14. Donnatella says:

    Great story, exactly what you always deliver.
    My fantasy has always been a spoiled, bratty wife, sometimes fantasy and reality meet.

  15. Pooky says:

    Love the story! I had to think about the fantasy costume and couldn’t decide on a favorite so I asked Dev for help… He said the french maid and then after thinking about that, I have to agree. 😉

  16. Loved this story, and a schoolgirl is always a favorite. As per my costume, if I were in this schoolgirls vicinity, I would go with my headmaster’s costume. You can guess the rest……….

  17. Loved the story! It was fun to read about someone who really wanted to be spanked and enjoyed it just as much as she thought she would. Hmm. My fantasy outfit? Inspired by the Spank Or Treat story I read before this one, I think I’m going to go with 50s Housewife. With one of those full skirts.

  18. houston_switch says:

    Naughty school boy… white button down shirt, grey pants, thin tie…
    Paddled over pants in classroom… paddled andover caned on bare bottom in Head Mistress Office.

  19. Sunny Girl says:

    What a great story. Thoroughly enjoyed, once again proving there are no accidents.

  20. Blondie says:

    I love this story. Showing up at a home like this for a spanking is a fantasy which would be a great reality. A naughty school girl or a naughty secretary have always been favorites of mine.

  21. Joe gallo says:

    Loved story. My favorite costume is Harry Potter as a school boy.

  22. Kelsey S. says:

    Loved the story, but then again I love all your stories (I just finished False Pretenses this week and loved it).

    My favorite costume would be a french maid.


  23. Is there any other Halloween outfit to be worn except “naughty schoolgirl”? I suppose if you’re a dude you might try another look.

    My husband bought my schoolgirl outfit. It features a tiny midriff-baring sweater top that highlights my breasts to full effect, a pleated plaid skirt that covers just two-thirds of my butt (I wear thong panties), white thigh-high stockings with ribbons attached on top and stiletto-like Mary Jane shoes.

    It’s not really a costume though because my husband makes me wear the outfit every day. But on Halloween he likes me to change things up. This year I’m going with sweatpants and a paint-stained tee-shirt.

    claire aka 1950s Wife

  24. Renee Rose says:

    I have a thing for school girl too!! Great story!!

  25. jennifer mathis says:

    naughty nurse is mine

  26. Nikki says:

    LOVED the story!!!! My fantasy costume is naughty maid or housewife!

  27. Starla Kaye says:

    A fun story and I definitely like the headmaster over the loser Jack.

    My fantasy…hmmm…naughty cowgirl taken in hand by her gruff, firm but loving cowboy.

  28. Mera says:

    Fun! Costume: sexy little red riding hood.

  29. Cassandra Hicks says:

    Mine is an elaborate dark fairy costume 🙂
    Thanks for the awesome giveaway!

  30. Alice Dark says:

    I love schoolgirl stories, Cara. Lovely read.

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