The Dilemma

This is a story inspired by a woman I work with. I'll not reveal her age or anything about what she looks like so you can close your eyes and see the image you yourself would like to see. But the rest of what I describe about her is true. Hope you enjoy this little story as much as I did writing it.

I met Deanna when she joined the company I work for a few years back. Ever since I trained her we had been inseparable. She's a pocket rocket full of energy and positivity and I make sure she knows it. At 5ft tall she's one foot smaller than me. But she always wears stunning heels to make herself taller. With a fantastically small figure she can wear anything and boy does she wear it all well. I never fantasized about her wearing boots before until she wore leather boots for the first time yesterday morning. I had a boot fetish, especially a leather one, but never once did I think about being kicked in the balls by them, that all changed yesterday. All day I kept stealing glances at them hoping she wouldn't notice. They were just a normal pair of pointy toe, size 5 leather knee high boots with a 4inch heel. But on her feet they hugged her calves skin tight. They just accentuated her beauty and I couldn't stop thinking about them.

At lunch thankfully I was able to keep my cool and act normal. That was until about 3pm a few hours before we left for the weekend. She came up to me at the coffee machine.

"Hey James, could you give me a lift home tonight? Tobias (her husband) is going to play football last minute so I need to find my own way home. No worries if not, just thought I'd ask." I had no reason to be worried. It was normal for us to do favors for one another.

"Yeah sure Deanna no problem. I'll meet you at the top of the stairs at 5pm like normal." She thanked me and went off to her desk and I did the same. As I sat down Suzie the girl who sat next to me glanced at me. I looked back at her and she opened her mouth.

"I told Deanna you kept staring at her boots today and have a boot fetish." My jaw dropped open. I couldn't speak for a few moments. I was stunned. When I finally spoke back I tried to sound authoritative.

"Suzie, you're out of line. Deanna is one of my best friends. You shouldn't be trying to spread office gossip and lies like that. And neither should you be trying to drive a wedge between us." She just raised her eyebrow and leaned in closer. The anger and venom was beginning to bubble close to the surface on both of our faces.

"Fuck off James. You stare at my boots constantly when I wear them. I've seen you on pornhub at break times watching boot humping. And I wonder how many times you've masturbated in the toilets. I bet at least once a week. Let's face it, I'm right."

I turned away unable to hide the anger and shame on my face. I plugged my headphones in and ignored the evil bitch beside me. Suzie was single, stunning and savage with her tongue in equal measure. She was 5ft 4ins tall with size 6 feet. Her body was sumptuous but I still thought Deanna was sexier. Her personality was much, much nicer.

I met Deanna at the top of the stairs but now I couldn't help but be a little apprehensive after Suzie's confession. How would Deanna react? Or was I being pranked by Suzie? Bloody hell! We had a casual conversation as we walked to the car and the drive home went uneventfully. That was until we got back to Deanna's house.

"Hey, James, come inside for a coffee, we can continue our chat. Tobias won't be home. I need to talk to you about something." I nod my head and reply.

"Sure Deanna, no problem. Never one to turn down a coffee." I do my best to smile and Deanna smiles back as if nothing is out of the ordinary.

We go inside and Deanna begins making a coffee. She is struggling with how to begin her conversation. She places a hot cup of steaming coffee in front of me and sits down at the table opposite me. She finally begins talking.

"James, I don't like it when we keep secrets from one another. So there's two things you need to know that I, myself, have been keeping from you. But after speaking to Suzie I realize you yourself have been hiding a big secret too. James, if we're going to remain best friends we need to be unafraid to be honest with one another. We can talk about anything and everything. Please don't feel like you can't be yourself around me." As she finishes speaking I'm aware her right boot which is crossed over her left is really close to the inside of my right leg. I begin getting aroused. I couldn't help it.

"Deanna, you're right. Let's be open and honest with one another. And hopefully we can make some sense out of this all." I smile as I place my hands on the table open palmed. Deanna places hers on mine and gives them a squeeze as she smiles.

"Good because my secrets are tough to talk about. But you'll understand why I hope.

Me and Tobias split up several months ago. We just weren't compatible with one another. We tried but sadly it wasn't meant to be." I squeeze her hands and open my mouth to speak. That's when she places her boot hard into my groin and places her finger over my lips as I go to yelp in pain. She applies pressure to let me know she's in control as she begins speaking again.

"Let me finish before you speak, James. The second secret is I love ballbusting. Not many guys I've met enjoy it. And truthfully I find it's more of a turn on when the guy doesn't enjoy it. So James, what I'm trying to say is, with your boot fetish and my ballbusting one, tonight is going to be a long night. Because I plan to ballbust you. Let's call it punishment for you keeping your boot fetish from me." She begins to press her boot harder into my balls. I can feel the tip of her boot pressing my cock hard against my chest.

"What the OWWWWWW fuck, what, AAARRRGGGHHH, about, JESUS!! Your punishment, FUCK, for lying to me?" She kept pushing harder against my cock and balls as she just stared into my face. The sadistic smile on her face told me she was enjoying herself.

"Well, I thought about that. And I've got the perfect punishment for myself later. Trust me you'll understand soon enough. Now James, take your clothes off. I want you to feel my boots against your bare cock and balls. You have 10 seconds or I'll cut them off with a knife. Ten, nine, eight…" I obeyed her order. I believed her threat by just looking in her eyes. She grabbed my hand once I was naked and led me to her spare room. It had a simple shackle running down from the ceiling which she used to tie me up with my arms raised above me. I was shaking through fear. She was enjoying the power over me. As she applied a spreader bar to my legs to keep them separated I knew I wasn't going to be released anytime soon. She shoved my socks in my mouth and used gaffer tape to gag me.

"Sorry James, I have neighbors to think about. I know you don't want this even if your cock is hard at the sight of my boots. Just let me enjoy myself. My happiness is important to you isn't it?" She pouted and gave me puppy dog eyes. I was enraptured by her beauty. Even at 5ft tall and only up to my shoulders even in her boots I couldn't help but lose myself in her charm and beauty.

I watched her stand in front of me and press her left boot into my balls with a gentle teasing tap. My balls bounced against the middle of her boot and I could feel her foot underneath the surface of the leather. She began breathing erratically, clearly getting more and more aroused.

She swung her left boot back and landed a hard blow into my balls with stunning accuracy. I felt my balls slam into her foot then ricochet against my pelvis and back against her boot. She shuddered in euphoric excitement and watched the pain register in my face. She felt me shake and heave a little gasping and muffling a scream against my makeshift gag. The pain I felt was excruciating. I felt sick instantly and I had no time to process it as I watched her swing her left leg back again and slam her next kick into my balls. The same process happened again. She left her boot planted hard against my balls as she slammed up and back down against her small booted left foot. I began to sway and my cock was rock hard. I was struggling to keep my feet down on the ground.

Deanna was clearly getting more and more aroused. She grabbed my head with her right hand and bent it down so I had a perfect view of what she did next. She lifted her left leg in the air as if she was kneeing someone in the balls. Her little gorgeous boot was mere inches away from my cock and balls. Still rock hard she slammed her boot forward keeping her thigh high up in the air. So fast repeated small strikes were raining into my tender balls. I was screaming with pain into my gag. Each strike against my swelling balls were getting tougher and tougher to take.

Then Deanna put her left hand down her panties and began rubbing her clit. As she did so she stopped kicking my balls and pressed her boot up against my tender balls and pushed my hard cock against my stomach. As she kept rubbing herself slowly to an orgasm I watched her boot begin to rub my balls hard against her booted foot. She began moaning loudly as she quickly worked herself to an orgasm. I was on the brink of joining her as her orgasm subsided when there was a knock at the door.

"Oh, that'll be my punishment James. I best go open the door." She disappeared as I was a stroke or two away from having the most amazing orgasm of my life. She had edged me to the brink of ecstasy and then dashed my own happiness.

As the door opened and Deanna walked in I realized she wasn't alone. Before the other person stepped in Deanna looked at me and dropped her head as if sorry. Then I understood why. Suzie stepped in. When I saw what she was wearing I nearly cum without any help from Deanna.

"James, it's about time you took punishment from my boots. Deanna is going to watch me administer it to you and as punishment she is not going to be able to participate or bust your balls at all tonight. We agreed this would be a sufficient punishment." She must have missed the fact that Deanna had already kicked me before she arrived. The look Deanna gave me and the pressing of her finger to her lips as Suzie got to that part told me she had already broken her agreement. And the evil Deanna had managed to cum as well.

Suzie stood in front of me. She was wearing a gold dress, gold gloves and PVC knee high gold boots. She grabbed my head and pulled it downwards like Deanna had earlier and I watched Suzie slam her knee hard into my balls. The slapping sound as her bare knee made contact with my balls engulfed the room. Deanna was clearly not enjoying having to watch someone else bust instead of her. Suzie stepped back and began her real onslaught.

Kick after kick rained into my balls. Suzie wasn't the best kicker and she clearly lacked experience. Deanna mentioned this to me once she had gone home. And judging by the purple bruises that were forming against my legs she had some truth to her assessment. I couldn't do anything to stop Suzie. She kept kicking me for what seemed like hours before she finally stopped. Finally on the brink of passing out she stopped.

"Deanna, how many was that?" I glanced at her trying to figure out what was going on.

"477 Suzie. Not bad but I can do better."

"I bet you can. Well, when it's your turn we'll see." Both women turned to me and explained what was happening.

"Suzie here was wondering how many kicks she could do in twenty minutes." Suzie looked smug as she finished the rest of the explanation. "Of course that's just standard strength kicks, no rapid or full power." As they leaned down to inspect my flaccid cock and swollen balls I could feel my body shaking and the feeling of bile in my throat as I was on the brink of being sick from the onslaught I had faced.

For twenty minutes I had to watch Suzie and her fucking gold PVC boots slam into my balls and thighs. When she connected properly the clap sound sent shivers through my body as the sharp pain rippled through my balls reaching my brain. I had to hold my breath to deal with the agony within my body. I was willing myself to pass out so I didn't have to see her smug grinning face as she squealed with delight at hitting my balls.

Then there were the thigh smacks when she was off target. Always seemingly hitting in the same tender spot. It was like she had a knife jabbing into my skin with each connection, the searing pain adding to the continued ache from my balls.

Then there was the worst of the lot. The tip kicks which were brutal. Suzie was so inexperienced at kicking she couldn't help but connect with my balls with every part of the boot. But every single fucking tip kick usually resulted in her stiletto heel following through and connecting as well. And these kicks didn't hit both balls, it just landed on one testicle. These kicks made me scream into my gag and convulse and go wild. I couldn't control myself. But as her tip and heel kick slammed into the middle of my nut meat I had nowhere to go. I couldn't cover up and I had to watch this bitch stumble on her follow through as her boots landed back on the floor. The ripple of pain burned and screamed within my battered balls deeper and more intense than anything I've ever felt before in my life.

When Suzie had finally finished I felt numb inside. Suzie was nothing but a bitch. No doubt she had put the wheels on motion for this to happen. And all I could think about was revenge. But before I could even develop that feeling deeper I could see a look of concern on Deanna's face as she scooped up my swollen tender balls in her small hands.

"Jeez Suzie, you've done some real great damage here. I don't think he can handle much more. Least for his first time." Deanna said to the sadistic bitch Suzie.

"I think he can handle some more. Tell you what Deanna, I was going to offer to let you have a go but if you insist he's had enough then we can stop." Oh shit I didn't like the way this was going.

"Actually come to think about it, I reckon James here could take a few kicks from me. What do you think, James?" She looked at me, then I felt the middle of her boot gently resting against my balls. Then she began pressing my balls against them as she rubbed up and down so my balls were being rubbed against her foot inside her boot. My cock got rock hard again as I looked deep into her eyes and nodded feebly. The power Deanna had over me with her boots on was hypnotic. She jumped up in excitement and stood in front of me. Once again edging me close to heaven only to be thwarted again.

"Tell you what James, how about Deanna kicking you in the balls until you cum? That sounds fair doesn't it?" I have a look of defeat in my eyes as Deanna and Suzie both giggle and high five one another. My brain was telling me it was yet another ruse to edge and deny my pleasure once again.

But also I have to once again endure the agony of kicks to my balls as Deanna begins her assault with much better accuracy than Suzie. My cock this time remains rock hard as Deanna rains in hard kicks to my balls. She keeps her boot hard pressed against my balls until they have repositioned themselves against her boot after her hard kick to them. She once again uses her left boot as she pummels my balls into submission. The pain of her kicks is more intense than Suzie's were and it's clear Suzie was getting off watching me take kicks from Deanna. This time Deanna is clearly feeling more aroused than she was earlier as both women keep orgasming whilst I am slowly edged and denied. Each orgasm Deanna is having in front of me is tough to watch as she stops busting my balls. By the time I see her sexy boot slam into my balls again I have to go through the process of getting hard again.

After a solid hour of being kicked hard by Deanna I finally cum all over Deanna's left boot. I've never shot a load so intense and long in my life. Stream after stream covers the entire front of Deanna's left boot. As she withdraws it Suzie places her own right boot hard into my balls as I continue to squirt my load onto her boot. Finally after covering her boot in my thick cum I stop orgasming. I'm barely awake as I am completely spent and tired. My stomach is convulsing with cramps from the abdominal pain and my balls are aching badly. They're swollen three times their normal size and I'm ready to pass out.

"Fucking hell James, you've covered two boots with your cum. I think you should clean them with your tongue." Suzie grabs my face and takes off my gag finally as she's instructing me about what to do next.

"That's right James and I think you should kiss all four boots afterwards to thank us for doing this to you. You deserve that reward." Deanna seductively says to me. I see Suzie nod her head in agreement with a grin on her face. "Don't forget we want our stiletto heels sucked clean as well." Both women smile as I begin cleaning the cum off Suzie's boot.

I take my time to clean and worship both pairs of boots and I'm rock hard again by the time I finish. Just as I am finishing Suzie turns to Deanna and blurts out something she clearly wasn't meant to.

"So have you told James you have a crush on him yet?" The look of horror on Deanna's face at knowing I've heard something that's yet again another secret being told to me from someone else was evident right away. Suzie realizing I was unaware really struck home how devious these two women had been.

With all my remaining strength I stand up and begin dressing without a glance or word towards both women as they struggle to find the words to say to placate me. I wave their feeble attempts to speak to me off and slowly walk out of the house and into my car. By the time I get home I crash on the sofa too exhausted to even climb the stairs to sleep in my bed.

I awake at 9am still in pain, still with my balls bruised, swollen and weeks away from being back to normal. I check my phone and have 18 missed calls. Three from Suzie and 15 from Deanna. I have about 10 texts from them both but I'm not interested in reading them. It's Saturday and I don't have to deal with them until Monday. Or so I thought.

A knock at the door at midday made me forget momentarily that it could be one of them. Sure enough as I opened the door Deanna was standing there. Thankfully there are no boots on her feet. She steps into my house before I can shut it again.

"Don't speak James. Let me explain myself. I know you're mad. I kept another secret and truthfully I only mentioned to Suzie when she spoke to me in the office, telling me about your fetish, about how I felt about you. I wanted to see how you handled the ballbusting before I decided whether to tell you how I felt. Relationships are meant to be equal. If you want to enjoy your boot fetish with me, I need that same commitment from someone I love, which is you, that you will let me indulge in ballbusting because that means a lot to me. I don't care what I wear on my feet as long as I get to bust balls every now and then. It's even hotter that you're not into it as it turns me on more. That will make sex even better. Tobias never ever knew about my fetish because he was so prudish. But with you I feel we both embrace one another's kinks in a way I've never felt with another man before."

This was clearly a huge thing for her to talk about and I could see why she struggled with telling me. Same way I couldn't bring myself to talk about my boot fetish.

Deanna opened her huge handbag and pulled out a pair of long leather boots. She kicked off her sneakers and put her barefoot inside the left boot first. As she zipped her left boot up she rested the boot in my balls and proceeded to put her other boot on. It was only then I realized they were crotch high. She stood up and turned around. She grabbed my head from behind and pulled it between her thighs and clamped my head firmly between her thighs. I felt the power of her thighs as she kept me firmly wedged between them. Not too hard that I struggled to breathe. As my hands grasped the front of her thighs I felt her strap them tight against her boots with the strap at the top of her boots. My hands were now strapped up tightly against the front of her crotch boots.

"James, I want you to get a good look at my boots. I'm not tall, my feet are small, but in boots I feel sexier than I ever have before in my life. Last night I had never worn boots to ballbust. Now I'll never wear anything else on my feet to ballbust other than boots. But I want to be a one man woman. I don't need nor want you to ever say you love being ballbusted. But I just want you to love me for the person I am. Just as I will love you for the person you are."

As I looked at the front of her boots I had a decision to make. Do I become her ballbusting slave and in turn get to worship the woman whom I care more about than myself? Or do I turn her down? I had fallen in love with her over the past few months as she clearly had me. But I had no desire to have my balls beaten by anyone. Could I sacrifice that knowing she gets aroused and loves the fact I don't enjoy being ballbusted?

As she released my hands and neck from her thighs I had a tough decision to make.

I looked into her eyes and made my decision in a heartbeat.