Daniella's Wedge Boots

This is a story request from u/gloomy_decision2177. Hope you enjoy this buddy as much as I did writing it.

Her name was Daniella, I had a crush on her since the day she joined the office. She was from Italy and as you can imagine, her tall, slim figure turned a lot of heads. But no one ever seemed to be able to get a date with her. I usually got tongue tied around her and she as a result thought I was extremely shy. Her black hair, olive skin and 5ft 8in height made her as tall as me barefoot but miles out of my league.

Today she was wearing her usual office clothes, a tight black skirt just above the knees, a black shirt and for the first time since she began working in the office boots. They were knee high wedge boots, Italian leather to match her heritage. She looked stunning in them. Finally for the first time I managed to actually talk to her at the coffee machine.

"I like your boots Daniella". She smiled at me and raised her eyebrow. "Like? Only like?", She teased me with her Italian accent. I was going red in the face. "Sorry, how rude, I meant I love your boots". She giggled and playfully slapped me on the arm. She instantly knew the power she had over me. "Oh, I see Evan. You have a boot fetish don't you". I nodded my head almost shamefully. She told me it's nothing to be ashamed of as she walked away with her coffee.

I didn't see her again until I was leaving the office. Suddenly as I entered the busy street in the business district she suddenly appeared by my side and linked arms with me. "Let's go back to my place. There's something I want to show you". I had no choice but to follow, her enthusiasm was clear for me to see. A few blocks later we appeared at a small apartment block and I followed her in. She opened her single apartment where she lived alone and ushered me to the sofa. She made a coffee for us both and as it cooled she led me to a closet. "Look at this, heaven right?", She smiled as I saw a collection of boots that ran the length of the entire room. She must have had well over a hundred pairs of boots. Different lengths, heel sizes, colors and materials. She noticed my hard on and giggled aloud. As she closed the door I drank the coffee in one go. It tasted funny. And before long I felt my legs getting weak and my head feeling light. I passed out.

I woke up sometime later completely naked and tied up in restraints to the wall. I wondered how she had gotten my dead weight up like this but noticed she had a hoist on the ceiling. Fuck, she's done this before. I begin mumbling as I see Daniella sat patiently awaiting me to come out of my stupor. She stands up and walks over to me. She hasn't changed her outfit or boots since we got in.

"Since you like my boots so much, I thought I'd introduce your balls to them. So scream all you like as this room is soundproofed. I'm going to kick your balls hard. And I'm not stopping until I've had enough, not you. Understood?". I just replied saying "yes Daniella".

She stood in front of me and gently tapped my balls with the front of her wedge boots to gauge her standing point. She swung her leg back and viciously slammed it hard into my balls. The sound was brutal, the pain inside my stomach suddenly became all too real. My balls were burning and the feeling of sick was unbelievable.

"OH FUCK, OH FUCK", I scream. "PLEASE, OH GOD PLEASE, STOPPPPP", the last word was interrupted by her second kick slamming into my balls hard. This one was even more brutal than the last one. I felt my balls fly up in my sack and slam into my pelvic bones. "FUCKKĶKKK", I yelled before the bile finally decided to escape. Daniella was ready for this and had a bucket ready as I heaved all the contents of my stomach out violently. As soon as I finished puking she kicked me hard again in the balls. This time she left her boot planted in my balls as my body shaking so much from the fear and pain began to involuntarily bobble up and down her boots. She clicked her little hand held clicker whilst laughing at my pain before finally explaining what she was doing.

"I'm counting how many kicks it takes to make you pass out. You know what the record is? Have a guess?". By now I can barely make any sense of the fog of pain going through my body. I take a few seconds to understand what she has said. I had no idea how many kicks someone had taken to pass out before. All I knew was as much as I didn't want to pass out, if it took this pain away from me I was all for it.

"Twenty", I just hashed out a number. I didn't put any thought into my answer, I just needed to say something. She began rubbing my balls up and down the front of her boot. My cock was getting rock hard at her expert stroking. "Mmmmm, random guess, but sadly not correct. No ones ever gone beyond nine". Fucking hell I thought to myself. I had taken a third of the record. Surely someone had tougher balls than me. But before I could speak Daniella knew instinctively again what I was thinking. "After the first three kicks I usually begin kicking full force". I began trembling even more then through fear.

Daniella went in for the killer blows. She launched a rocket kick hard into my balls without holding anything back. I took it and emitted a high pitched whine from my body. The wind had been taken from me and I was trying hard to not be sick again. "Awwww Evan, that sound tells me one or two more should do the trick". She was once again spot on with her prediction. Her next kick, my fifth, finally made me pass out. The last thing I remember before I went into a sleep abyss was the sound of her boot connecting with my balls. It's a sound ill never forget. It was in my ears like a stick of dynamite had emitted it's high squeal of delight, like a firecracker exploding. I later found out that sound came from me directly. Thankfully I never felt the pain of that blow before I did lose consciousness otherwise I'd likely have cried all night.

When I woke up I was now lying on the floor. My hands were finally free, but my balls were not. They were on fire and severely swollen. They were also trapped tightly into a cockbox. I knew what was coming next as Daniella was standing on the cockbox with her wedge boots, either side of my balls, gently tapping away patiently waiting for me to wake up. I knew she was just waiting to torment me further.

She crouched down to move her face closer to mine. She lifted my chin up so I was facing her with her index finger. I am totally captivated by the control she has over me. She begins speaking "my desires haven't been met yet. I don't just break balls, I break spirits. I break resistance. I break men. You want to know why I chose you? Because your weakness is my greatest strength……boots. Now let me make myself real clear. You will not speak anymore unless I ask you a question. And you will fucking speak when asked a question. There are three things I guarantee are about to happen. One you will cry, two you will beg for mercy, and three…..I will break you".

I was speechless, through shock, fear and her orders. She stood back up slowly and placed her right boot in front of my cock and balls so I couldn't see beyond it. Then without any warning I felt her left boot slam down on both my swollen balls. My head shot up as I gasped in shock and in pain. Daniella had anticipated this and as she stood full weight on my balls trampling them under her wedge boot sole her right boot lifted in the air. I watched it move closer to my mouth and push my head down aggressively to the floor. Instead of covering my mouth which I was expecting she placed her right boot sole on my throat. It was a shrewd and brilliant move. I was now torn between a rock and a hard place. The more pressure she placed on my balls meant the looser her right boot was on my throat, the more pressure on my throat the less she placed with her other boot on my balls. My free hands were torn between trying to fight off the pain she was causing to my balls and the lack of breath her other boot was causing as it crushed my throat. She was now laughing at my predicament as I was slowly losing the strength to resist that I had left. She kept up this torment for ages, until finally my hands flopped down in full submission. Finally she stepped off my throat then lastly my balls.

She stood in front of me with her boots on either side of my balls. Now they had swollen so much she could crush one under each boot. Which is exactly what she did. She stood on both my balls with each boot sole at the front of the boots, right where the toes would be. She crouched right down with the back of her wedge heels both lifted off the cockbox.

"Stroke the front of both my boots, NOW!", she demanded. I did as I was told.

"Am I hurting your balls Evan? Does it hurt?". I open my mouth to speak but she slaps me hard "DOES IT HURT EVAN!! TELL ME HOW MUCH IT HURTS", she's shouting at me and slapping my face hard every few seconds. "It hurts Daniella. I've never felt more pain in all my life". She continues crushing my balls under her boots and slapping my face. "Do you want more Evan", she teases me. I don't know what the right answer is. So I say what I think she wants to hear. "Please, Daniella, hurt me some more". She smiled and simply said "correct answer Evan". She carries on slapping both my cheeks until they are red and sensitive to the touch.

She finally steps off my balls but it's only a temporary relief. She has one final act of busting to do before I'm broken enough by her. I didn't know it at the time but she was about to really have her fun.

She steps and crushes my hard on under her right boot. Then she begins stomping my balls hard under her left boot. The power and pain combined make me shudder with each and every stomp. She works in a rhythm and delivers ten solid stomps before stopping. I am in agony, my skin has been torn slightly by her wedge heels. Before I can catch my breath she simply turns her body around so her left boot is now crushing my cock and her right boot is ready to stomp.

She begins the process again. This time her stomps are even harder, this time she doesn't stop at ten strikes. She begins stomping quicker and quicker, my body is shuddering under the constant torment, I am barely conscious as her boots work my balls into submission. "Beg me for mercy Evan". I am unable to speak and Daniella is clearly angry at my failure to speak. She lands one final crushing stomp. This one lands flush against my now huge balls. But instead of just lifting her boot off me she begins twisting her right boot against my battered balls. "EVAN, BEG. FOR. MERCY", each word emphasized with a twist of her boot as I finally tap her boots three times in submission whilst I shout as loud as I possibly can.

"PLEASE, FUCK, MERCY DANIELLA, FUCKING HELL, MERCY, MERCY, MERCYYYYYYY".

She has a look of total shock on her face. She had never heard anyone previously beg for mercy with such compassion. It did not go unnoticed by her.

"Welcome to my inner circle Evan. You had to be broken by me to earn my respect and my trust. You are a rare breed. The only man who has ever passed my test. Now before we get to the fun part of the evening I want you to lick my boots. Every single inch of them". I had nothing left to give. I simply allow her to sit on my cock and balls which have been removed from the cockbox and I begin licking her boots.

I was led to the bed not long afterwards. Daniella continued to remain in control by climbing on top of me and riding my cock for the next few hours. My balls, battered, beaten and bruised caused immense pain for the whole duration.

As I dressed in my clothes slowly taking my time due to the sensitivity of my body Daniella reminded me she has plenty more pairs of boots to break me with. She laughed and I wasn't sure whether she was joking or not.

Only time would tell…..