Spanking Caption Contest !! Pls Give It a Try!

A marvelous sepia-toned image from master illustrator Roger Benson.

What do you think is going on in this image? Have fun with it and write a few sentences, a caption and/or some dialogue for
The Cherry Red Report’s “Spanking Good Caption Contest.”

Let your imagination run wild — and have fun !! (Prize for best caption To Be Determined) 🙂

Don’t all post or email at once! OK, OK, I shall be the first to try:

“Harold, you clearly have been ignoring your responsibilities in keeping Gwendolyn in line, as she has been rude, misbehaving, fresh and pouty all week — and sneaking out last nite when she was grounded. Must I show you everything, Harold, when it comes to discipline? And Harold, will you please get rid of that odiferous pipe of yours, immediately! Goodness! Now then, perhaps a well-deserved dose of the hairbrush might do Gwendoyln some good on that sassy backside of hers.”

Mrs. Jennison twirled the antique hairbrush menacingly in her hand, as Gwendolyn blushed bright crimson, her exposed panties suddenly feeling too tight, too hot on her tingling bottom.

Harold sat back and said nothing, re-lighted his antique wooden pipe, licked his lips and watched the tableau about to unfold.

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9 thoughts on “Spanking Caption Contest !! Pls Give It a Try!”

  1. Eleanor was so excited to be off the farm and in the big city. Picture shows and stockings sure beat feeding chickens. Her job at the mill was boring but there were so many men working there. That her big sister had learned well how to apply a hairbrush from their mom was a small price to pay. But how her brother-in-law leered at her painful red bottom was unsettling enough that she slept with her bedroom door locked. Oh well, tonight here sister would “reform” her, tomorrow there were more dates, more movies and more whistles from the men as she strolled down the street.

  2. I don’t understand, why do you give me the hairbrush and why do you stand like that, showing uncle George your knickers? And why do you smile, George? What is this all about?

  3. My contribution:
    “The girl had failed her exams. At that moment she was standing in front of her angry mother, her skirt was lifted up, knikers on, but only for a few time.
    The father sitted on his sofa watched the scene ready to discipline his daughter but not only, because his wife had the responsibility to take care about their daughter and her conduct. Now he relished the moment, soon he would teach how a little girl had to behave properly, and of course how a mother had to educate a brat”

  4. “Young lady, I’m going to give it to you as hard as I got it last night because I didn’t make you complete your schoolwork! This hairbrush will get my meaning across!”

  5. Roxanne stayed out past curfew and came home looking quite disheveled.
    Wait til Herbert takes a closer look and see’s that his won’t be the first implement applied to Roxanne’s bottom tonight!

  6. You have been a very naughty girl! I told you that Daddy would think so, too! Now that you have shown him your spanked bottom, get upstairs to your room! No dinner for you tonight!

    Thank goodness your Father and I can have some fun with this hairbrush tonight without you interrupting!

  7. Hi Dave,
    Great pic! Here is my caption:

    “Aunt Em had finally found out where Dorothy had ‘really’ been since the tornado hit – and it wasn’t with Toto…” 😉

    Hope you like it…
    Em x

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