This happened when I was dating Jan.

He once told me a fantasy of his. When he was a child, he watched an American movie called Starship Troopers. In that movie, a soldier was tied to a post and whipped mercilessly. Since he saw this scene, he was dreaming of doing this to a woman. He even showed me the scene on Youtube. It looked brutal. I said no. But I also said that we could explore whipping if he wanted. We read up about whipping on the Internet and arrived at a plan.

The plan started with me shoplifting.

On Saturday, at an agreed upon time, I went to a grocery store. I picked up a few items and placed them inside my cart. Then, trying to act casual, I quickly slipped two packages of expensive chocolate into my bag and made my way to the checkout line. I smiled at the cashier, forcing a casual demeanour. I paid with my card and went towards the exit.

I saw Jan in an official-looking constable uniform approaching me. He looked grim. As I stepped out of the store, Jan stopped me.

"Good evening, miss," he said, his voice gruff. "I have a report that you were shoplifting. Can you please empty your bag?"

I tried to look shocked and confused. He took my bag and emptied it. The chocolate was revealed.

"Miss, these chocolates are worth a lot of money," he said. "I will have to take you to the police station."

"Please, sir, I can't go to jail," I pleaded. "Maybe there's another way we can work this out?"

Jan led me to his car.

"Please get in," he said. "There will be an alternative punishment."

We drove to his apartment block, and Jan led me to his apartment. I had been to his place multiple times, so I immediately noticed a new element in his living room: a wooden pillory.

The structure looked medieval. The main framework consisted of two posts. Between the posts, a wooden board, split horizontally in two, was mounted. This board had three circular openings, the larger one in the centre for the neck and two smaller ones on either side for the wrists. Iron clasps held the contraption together.

Jan closed the apartment door, ordered me to undress, and led me naked to the pillory. He positioned me with my head and hands through the holes in the pillory and secured my neck and wrists in place with the iron clasps.

The wood against my bare skin was rough and scratchy. My torso was bent forward uncomfortably, and my ass was exposed.

Jan ran his hand over my ass, and squeezed it tightly.

"Bad girls need to be punished," he said.

Suddenly, I felt something hard and smooth slide across my ass. It was a wooden paddle.

He started to hit me with the paddle. The first few hits were gentle, and I felt a slight sting. But the more he hit me, the harder it got. My buttocks started to tingle and burn.

Jan did not speak. He just kept hitting me, alternating between my left and right buttocks. The pain was intense. My neck was pressed against the rough wood of the pillory, and my wrists ached from being locked in place.

Then he stopped. From the sounds I was hearing, I understood that he walked to the freezer and took out a bag of ice. He placed it on my buttocks, and I jumped from the cold sensation.

The ice was a welcome relief. It numbed the pain, and I felt my body relax. Jan started to massage my ass, his fingers caressing my tender flesh. I moaned softly as he kneaded my muscles.

"You like it, whore, don't you?" He said, "You're such a pathetic pain-slut."

I moaned in response.

He suddenly hit me with a paddle again. It was a hard blow, and I cried out in agony.

"Answer me!" He demanded and hit me again.

"Yes, sir," I whimpered, "I like it."

He applied ice again.

"The warmup is over!” he announced.

I heard a “swoosh” sound of whip swinging. The first strike landed on my ass. Even though it did not quite cut my skin, I felt its impact.

"You will get 10 more lashes," he said, "I want you to count each one of them and thank me."

The next strike landed on my thighs, and I gasped.

"One, sir, thank you," I said, trying to sound grateful.

He whipped me again and again, and I counted. He targeted my buttocks, my back, and my thighs.

I felt my skin sting and burn as the whip was landing on my body. With each stroke, my body was overwhelmed with a mixture of pain, adrenaline, and arousal.I was filled with a sense of fear and anticipation. I had no idea where he would land the next blow, or how hard it would be.

Sometimes he would swing the whip, I would become tense anticipating the blow only for him to stop at the last moment and touch me gently with the tip of the whip. But once I relax, he would swing again and land a blow.

As I counted, I was having trouble keeping my voice steady.

By the time Jan finished whipping me, I was a mess. My buttocks, my thighs, and my back were bright red, and I was exhausted. Jan picked up the bag of ice and placed it on my buttocks. He caressed my bruised body and moved the ice all over it.

"You did well, slut," he said. "I'm proud of you."

Then he stood in front of me and unzipped his pants.

"Make me cum, slut," he commanded, "or you’ll get another round."

I immediately started to suck his cock. I sucked greedily, wanting to please him. Then he pushed his cock into my mouth, and I gagged. He grabbed my hair and started to fuck my face. I was feeling his balls slap against my chin. When he came, and I swallowed his load and licked his cock clean.

By that time, I was desperate for some kind of release. I could feel my juices dripping down my thighs.

"Please, sir," I whimpered, "please fuck me."

Jan took the whip and teased my clit with the handle. I could feel its rough edges rubbing against my sensitive bud. He then began to thrust the handle in and out of me.

"Please, sir," I begged, "let me cum."

He kept fucking me with the handle. My body was tingling as the orgasm was approaching. Suddenly he stopped his movements and held the handle still in my pussy. I was too aroused to stop, and I kept grinding my hips.

He laughed.

"Such a desperate whore," he said.

I began to thrust my hips harder, trying to get myself off. And then he suddenly plunged the handle of the whip deep into my pussy.

I screamed from pain and pleasure.

I shuddered and came hard, my body trembling.

Jan released me from the pillory, and I immediately started to rub my aching wrists and neck. He took me to the bathroom and helped me clean up. He massaged my body gently, and I moaned as his fingers brushed against my bruised skin.

After I was clean and dry, he led me to his bed. We cuddled and fell asleep while embracing each other.

We broke up soon after that. He asked for an open relationship, but I refused. He said he wanted to pursue other girls anyway. I was offended and told him we were done.

Now, I think that I overreacted. We stopped talking to each other. We reconciled later and are on good terms now, but we never had sex again.