I’ve been very excited about the acquisition of my vintage whip and I’ve been itching to christen it on Robert’s bare bottom. He wasn’t quite so keen though. I caught him sneaking a look at it a few days ago. He had taken it from its cardboard tube and he was flexing it. I loved the guilty look on his face when he turned to see that I had stepped quietly into our bedroom.

“Perhaps you are trying to imagine what it will feel like when I take it to your bare bottom?”

“Well, yes,” he admitted.

“Then tomorrow you shall find out. I want the whipping bench assembled by 9am.”

I left him, still holding the whip, now with less than 24 hours to contemplate his fate.

The christening of the whip was to be a punishment whipping for shoddy spell-checking of my last book, ‘Spanking Games’, so I decided that it would be appropriate to incorporate a game into the punishment. Dice games are always fun, so I thought I’d invent a new one. I explained to Robert how it would work later that evening:

His punishment, a hard whipping, would be decided on the throw of a standard six sided dice. Each number on the dice would be allocated a number of strokes of the whip.

Generously, I told Robert that he could choose the first two, then I would choose the remaining four. I could see he was suspicious of my generosity.

“So I can choose any numbers I like? Even very low numbers?” he asked.
“You’re very suspicious, Robert, I can see it,” I said, enjoying his discomfort. “Would it help if I told you that I’ve already decided on my four numbers. You can choose anything you like, but I would like them to be different numbers.”

He wanted time to think about it, which was fine, but I told him he must make his choices before I strapped him over the whipping bench.

Robert was still undecided on his choices when he reported to me that he had assembled the whipping bench the following morning at 8.55. He was frightened, of course, but he was still wary of my generosity in allowing him choose two of the whippings.

“You’ve definitely already decided on your four choices?” he asked.

“Definitely,” I assured him. “Now fetch the whip. Present it to me and tell me your choices. You’ve had quite long enough to think about it.”

“If the dice rolls one, I should receive one stroke,” he said, nervously, as he handed me the whip, “And if it shows a two, I should receive two strokes.”

He was expecting me to object, but I didn’t.

“That’s fine. Now strip and place yourself over the bench.”

“What are your numbers?” he asked.

“I’ll tell you when I have you strapped down,” I said, “But I can tell you that if you are not naked and over the whipping bench within thirty seconds I will add a dozen strokes to each of my choices.”

It was enough. Robert knows I never make idle threats. He was naked and ready to be strapped into position within twenty seconds. It took less than a minute for me to buckle and tighten all the restraining straps. He was mine. His unmarked bare bottom was thrust up, helpless, and perfectly presented for my whip.

“So Robert. It’s time for me to disclose my four choices. I was being quite truthful when I told you that I had already decided on my choices before you told me yours. I decided that my choices would be fifty, minus whatever yours were. So if the dice rolls three or four, you will receive forty-eight strokes, and if it rolls five or six, you will receive forty-nine.”

Robert groaned as I picked up the dice. I gave him a few moments to digest my choices, then tossed the dice onto the floor in front of him. He must have been praying for a one or two.

The dice throw was a little clumsy. It rolled across the floor, coming to a stop against the edge of our Afghan rug. I heard Robert breath out in relief as we both looked down to see the dice displaying a one.

“I’m afraid it’s not conclusive,” I said, as I stepped past Robert to look down at the dice from above. The dice was resting on one of its edges up against the rug. “From here it’s showing both the one and the five.”

Robert probably thought this would mean rolling the dice again. I had a better idea.

“The most logical thing to do, Robert,” I said, as I picked up the whip, “is to count both the one and the five as valid. So your choice earns you one stroke and mine earns you forty-nine. That very conveniently adds up to the very nice round number of fifty.”

I was hoping he would argue. I was really in the mood to make him squirm, and I would have delighted in adding another ten strokes for the slightest protest. Unfortunately he knows me too well. He wisely kept his mouth shut.

I took my position. Raised the whip, then the punishment began.


What a wonderful sound my new whip makes when it bites deep into the flesh of Robert’s bare bottom. My first thought was that it felt a little like using a cane, but it was heavier and had more flexibility, so it tended to wrap-around his far flank. That’s fine, I thought, it still counts as a legitimate target area.
It was quite clear what Robert’s first thought was. His hissed intake of breath and the manner in which his whole body tensed with shock said it all. It was excruciating. Just how it should be. Just how I love it to be.

But there was far better to come. After the first few strokes, which had him gasping and squealing, I instinctively introduced more wrist action into my strokes and the result was blissful. The whip really came to life and began to crack down across his upturned bottom with stunning severity.

Robert squealed and gasped and wriggled and cried his way through all fifty strokes, and what a glorious lattice of weals now decorate his bottom. When he was eventually released from his restraints, he was so covered in sweat from his futile efforts to escape the embrace of the whipping bench that I almost had to ‘peel’ him off it.

My vintage whip is simply wonderful. I’m so taken with it that I’ve written two short stories about ladies who take delight in whipping the bare bottoms of deserving males. It’s called ‘Ladies with Whips’. See my website for further details:



About Annie Bee Books

I am an author of BDSM fantasy stories.
This entry was posted in BDSM, Corporal punishment, Punishment, Spanking, Uncategorized and tagged , , , , , , , . Bookmark the permalink.


  1. cuck says:

    The whip sounds really impressive – I love when you give a bit of detail like when you describe your Hellstrap. I love ALL of your stories and buy all f/m canings and strappings. I wish you would write more often!
    I am sure a day in school could generate many different scenarios and tools for a naughty adult boy of course ending at home with strict wife/mother after passing by Headmistress

  2. sissyjamieanne says:

    I’d just like to say, Ma’am…I’m currently reading Punishment Project Two…and I’m only at 9%…but it’s developing amazingly! I’m loving how her relationship with Zak is evolving…some good things in the works! Thank you for sharing your craft…both as disciplinarian and author!

  3. Eddy says:

    It’s a great shame your stories are only available in Kindle, I honestly think you are missing a trick not bringing them out as hard copies.

  4. timothy210 says:

    Excellent account thank you. I’ve just read you new story based on your whip and very much enjoyed it.

  5. sissy jamieanne says:

    Wonderful Ma’am! Thank You once again for sharing Your delightful disciplinary adventures! Your new whip does indeed seem delightful, and a very classy, antique implement! You are without doubt an accomplished and amazing disciplinarian, and I always love to read about your “sessions” with Robert…I especially enjoy that You take the time in your writings to set the scene…the preparation of the bench, explaining Robert’s fears, setting forth the rules for punishment, preparing and presenting the buttocks for your ministrations…it’s all sooo delicious, Ma’am!!! You are simply the best!

    In respect,

    sissy jamieanne

  6. Anonymous says:

    Another interesting session, Thank you for sending it along.
    Your whip sounds delightful.
    Best to you both.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.