Cruel to be Kind
By Ok_Comb5279
It had been a year since my father had remarried after being a widower for years. At 21 I was back from college for the summer, sharing the house with my new stepmother for the first time. She was the same age as my father at 50 but she looked stunning. An ebony goddess who looked years younger than she actually was.
Today was the first time I was home alone and I was unable to control my hormones any longer. I just had to cum. And Dee, my stepmother, had an impressive boot collection to help me achieve my goal.
I got down onto my knees and placed my balls against the wooden board. I was naked and rock hard already. I placed her platform rounded toe thigh boot on my balls as the stiletto heel gently rested on the board next to my balls. I pressed down with my left hand so the boots were crushing me softly as I closed my eyes and began masturbating. I began slowly and within a minute my breathing suddenly increased, becoming faster as my hand worked hard to try and bring that desperate orgasm to the surface.
But as I was lost in my own fantasy I had failed to hear the door open and the stiletto heels of my stepmother walk into the room as I continued to wank furiously.
‘It'd be much more exhilarating and sexy if my foot was in those boots crushing your balls, wouldn't it?’ I suddenly turned my head around and saw Dee looking at me with no emotion in her face.
‘Oh, shit, I'm sorry, it's not what it looks like.’ I suddenly lifted her boot of my balls and felt my cock losing it's erection as I desperately tried to hide my embarrassment.
‘Oh, it's exactly what it looks like. You little pervert. You have a boot addiction. But why were you using them to crush your balls?’ She put her hands on her shapely hips as I saw her slip on stiletto pump heels tap the floor impatiently waiting for an answer.
‘I don't know. I've always liked the view of the boots when looking at my cock when I masturbate.’ I wasn't exactly truthful as I had my eyes closed but I was hoping she didn't realize that.
‘Put it back on your balls then sweetie. Let me see for myself.’ She had a look which showed she was curious and yet wanted to see if I'd listen to her.
‘Urm, no, it's okay. I've lost the mood for it now.’ I looked at my now flaccid cock thanking it for not rising again at the sight of her huge cleavage and sexy thighs.
She didn't say a word as she slipped off her stiletto heels and walked barefoot towards me.
‘Don't move, I'm going to make this real easy. My boots, my house, my rules. Now put my fucking boot on my foot.’ I began to shake in fear. This was a side of Dee I didn't know existed. Usually she was happy and vibrant, almost like the soul of the room. Now I was seeing her dominant side and it was terrifying me.
I placed the boot back on my balls. I watched as she slid her bare foot into the boot. It was like watching a hand slip into a glove. My cock was once again rock hard as it began increasing in size as I watched her foot slide into her boot.
‘Ohhhhhhh fuckkkkkkk.’ I suddenly shouted aloud as I suddenly felt her press down on my balls. Jeez, I was in agony. I yelped aloud again and suddenly I felt Dee clasp her hand across my mouth.
‘Let's see how much you can handle before you really tremble sweetie.’ Her voice, although trying to sound soothing, had a menacing undertone to it. Almost like she was trying to make sure I knew she was in charge. But I submitted instantly. My love of boots and her beautiful legs had made me instantly give in. But of course she didn't know that. She needed to press her point home and boy didn't she just.
I moaned loudly into her hand across my mouth as she increased the pressure. I couldn't move my balls were trapped under the sole of her vicious but sexy boot. She began to flatten my balls under her boot as the wave of pain kept increasing within my balls and brain.
It felt like I was being stabbed in the balls and the ache developed along with the sharp pain as she kept increasing and decreasing the pressure on my balls.
‘Now, I want you to continue your masturbation from earlier! Get wanking sweetie. Mommas gonna make sure her boot helps you cum.’ She laughed in my ear as I grasped my long erection. I began to stroke my cock hard and fast, desperately trying to cum and not disappoint my stepmother.
‘Slow down, slow down. Keep in rhythm with my boot pumping.’ She began to lift her boot slightly and pressed down like she was pumping the gas pedal of her car. It took a few seconds but then I got into rhythm with her.
‘That's good sweetie, now keep to the rhythm I set at all times. It'll increase so be aware of the change.’ I nodded my head and continued to masturbate.
I was trapped, being forced to wank by the stepmother crushing my balls underneath her platform thigh high boots. But as much as I was enjoying my wank, the pain in my balls was constant, and getting worse and worse. I knew my balls were swelling underneath her boots but I couldn't do a thing to stop her.
‘Good boy, now for the final push. Don't let me down!’ She suddenly increased the pumping like she was trying to squeeze the cum out of my balls. I was struggling to breathe as the intensity suddenly increased. That's when I realized Dee was pressing down even harder than before. She knew I was close even before I did myself. Without any warning I shot my load all over the front of her boots. After what felt like forever Dee lifted her boot off my balls and I collapsed to the floor clutching my aching throbbing balls.
Dee then put the remaining boot on her other leg and stepped over to me. She placed the boot beside me which was covered with my cum and crouched down so I could see her face.
‘Bet that felt amazing didn't it sweetie? Well you've got some mess to clean up. Get licking boy. I'll make a phone call whilst you clean up your mess.’ I didn't think much of what she said as I was in a pain and ecstasy stupor.
‘Hey, Samira, grab your Louboutins and get Stephanie to do the same and come round. It seems your little stepbrother has a huge boot fetish. And I know just the way we can help him get his fix……yep that's it, got it in one. See you soon.’
As I finished licking her boots clean I began trembling again. Dee had two daughters. Both were strong and stunningly beautiful. Thick thighs like their mom. And they were twins three years older than me. I had a feeling they didn't think much of me, now I was sure they were going to prove that to me.
‘Oh, Dan. I just wish I had known about this fetish sooner. To think I could have been having so much fun before now. But don't worry, I'm about to make up for lost time.’ I gulped in fear as Dee pulled my head up so I was on my knees in front of her.
‘Legs spread, and don't fucking move.’ Dee swung her boot hard and accurately into my balls without any consideration for my thoughts or wishes. I grunted but kept upright. She delivered another bone crushing kick hard into my balls. I leaned forward slightly but managed to take the blow. I didn't say a word but my balls were in agony. They felt like they were on fire, a pinball being smashed about within an arcade game and I couldn't do a thing to stop it.
Dee smashed her boot hard into my balls another eight times until she had kicked me ten times. I finally collapsed after her last blow. The pain was horrific as tears dropped down my face. I didn't say a word and as my face was away from Dee she didn't see me cry.
‘Fucking hell sweetie. You've got some serious ability to take pain. I'm actually impressed. Let me show you my appreciation sweetie.’ I was pushed over onto my back. Dee climbed on top of me and I felt her thick thigh press against my cock. It reacted to her touch and I was rock hard again instantly. It was then Dee began to rub her thigh up and down the shaft of my cock. It was crushing my balls with it but the pleasure overwhelmed my senses and I didn't feel the pain suddenly. It was like I was numb momentarily.
It was just as I was about to cum that I heard the sound of heels walking across the hard floor. Dee’s two daughters Samira and Stephanie walked in. I couldn't see as Dee was on top of me still but I could feel their presence. Dee continued to thigh fuck my cock hard and fast.
But before I could cum she began to slam her knee into my balls repeatedly. Not too hard but enough to tip me over the edge and ruin my orgasm. I ejaculated all over my bare chest as Dee laughed.
‘Never fails girls, no matter what.’
She lifted herself off me and I looked up to see my stepsisters staring at me. They had a smile on their faces as they waited for me to take in the sight of them both.
‘Ohhhhh, fuck.’ I gasped at the sight before me.
‘Girls, I'll leave him with you for a while. Mommas got to find her own matching outfit. And I need to cum myself after the fun I just had. He's all yours until I'm back. Have fun!’
What I was looking at petrified me. But what Dee said about her own matching outfit scared me just as much.
‘Don't worry Mom, we'll look after him, won't we Stephanie?’ Samira smirked at her sister as Stephanie smiled back at her before looking into my eyes.
‘Oh, we certainly will. Don't you worry Mom.’ Stephanie replied.
The fear was back, my body felt it. My balls felt it. But my cock was betraying me. It was once again rock hard.
‘Right let's get started then.’ Samira said as she took a step towards me.
* * *
As I looked at the twins stepping towards me I knew I was in trouble. Samira, the slimmer of the two, had a look of pure joy at what she was about to do. Both of them were wearing matching leather jumpsuits which perfectly fitted their curves in all the right places. They had long black leather gloves and crotch high Louboutin boots that seemed as though they were made for their legs only. Stephanie the heavier and taller of the twins stepped over behind me.
‘Don't worry Dan, me and Stephanie just want to have a little fun with you. We promise it won't take long.’ Samira winked towards Stephanie and both the twins giggled.
Samira then pushed my chest down with her boot so I was flat on my back. Stephanie sat down behind my head and within moments I felt my head being surrounded by her thick thighs. I was now trapped in her booted head scissors and I knew I had no way of escaping.
‘Relax Dan, don't worry, I know how much you'll be able to handle. Just keep your eyes fixed on my boots down your chest and you'll be fine.’ Stephanie said as she stroked my face with her gloves. I now couldn't see my cock and balls as my view was blocked by Stephanie and her big booted feet. My cock was hard and throbbing as I fixed my eyes on her boots. The shape of them, perfect on her sexy big feet. I nearly ejaculated just thinking of humping her boots.
‘Put your hands on my thighs Dan. Stroke them tenderly. And DON'T stop no matter what.’ Stephanie slapped my face to emphasize her point and I couldn't even speak or nod to say I understood. My neck was straining between her gorgeous thighs.
It was when Samira stood between my thighs and smirked at me I realized why Stephanie had told me not to move. Samira had her boot swung back so far I knew she wasn't holding anything back from her impending strike.
SLAM
The bile instantly flew up into my throat as the pain registered within my brain. The kick felt like a firecracker making contact directly with my balls. Her boot slammed hard into my balls with nothing held back. I instantly convulsed and it was clear why Stephanie had locked my head between her thighs as I couldn't thrash about underneath her lush legs.
Within ten seconds of her first strike Samira was already swinging her boot back for the next one.
SLAM
I violently began to shake as my hands trembled and tried to claw at Stephanie's boots. Desperate to try and free my neck so I could curl up into the smallest ball possible. My balls were on fire, the pain unbelievably intense in both my head and balls. My face, red and struggling between Stephanie's thighs. I knew one more strike and I was either going to puke or pass out.
‘Holy shit!’ Samira gasped out loud.
‘What's up sis?’ Stephanie looked concerned.
‘No one has ever stayed conscious for more than one of my kicks let alone two. Dan has balls of steel. Either that or I'm losing my power?’ Samira looked at her sister, now doubting herself.
‘That last kick was harder than any I've ever seen you deliver. There's no way you're losing your power sis.’
‘Fucking hope not. I'd hate to actually keep guys awake when I don't have to.’ Samira sinisterly said.
‘Let me have a crack at him. But let me knee his balls, you know that's my specialty.’ Stephanie said aloud as she unwrapped her thighs from my neck.
‘Stand up Dan, we're not finished with you yet.’ Samira replies as I slowly feel myself being pulled to my feet by the twins. It is only then that I realize that not only am I smaller than both women, I'm also weaker than both of them. The strength they both have scared and excited me at the same time. I feel my arms being pinned behind my back by Samira as Stephanie stands in front of me.
‘This is my own tried and tested technique. Slam a thick thigh between your legs then when the guy realizes it doesn't hurt that much, use the proper power knee. No one handles more than a few of these though. So don't worry, I don't expect much.’ Stephanie stroked my face as she spoke before pulling my head down. Intentionally so I can watch her slam her blows into my balls hard. My hard cock blocks some of the view but I can't mistake that thick thigh as I watch in horror as her booted thigh comes up and connects hard into my nutmeat.
She was spot on, it didn't hurt that much but the next blow was completely different. As soon as it slammed hard into my balls I knew what she was talking about. I felt the entire weight and power of her knee connect like dynamite against my balls. As her knee stayed against my balls it stopped me from buckling and collapsing to the floor. It was on par with Samira's kicks for pure power and I began to cry, the agony my balls were feeling penetrated every single sinew of my quivering body. The receptors now feeling completely messed up as body parts not even related to my balls or brains suddenly ached and begged for the muddle to stop.
But Stephanie didn't give me time to process the pain. I was once again forced to watch her knee slam into my balls hard. This time she didn't give me the softer blow and she just launched knee after knee hard into my balls as my legs became jello. I couldn't fall to the floor because each blow was delivered too quickly for me to collapse in time.
Finally after several minutes she ran out of steam and stepped away. I had stopped crying finally and mercilessly Samira let go of my arms. I stood there just about able to stay on my feet as both women stood side by side looking at me bewildered.
‘What the fuck is going on. He's still awake and he's still standing.’ Samira was perplexed as she spoke to Stephanie. I was hunched badly and clasping my swollen aching balls but I was still standing. Almost proud of my achievement but also scared of how far both women would go to try and break me completely.
The sound of heels walking into the room broke the sudden silence in the air. Dee walked in dressed identically to her daughters in a leather jumpsuit and matching Louboutin boots that went to the end of her long thick thighs.
‘So girls, I'm guessing by the silence you've figured out he has durable balls?’ with her daughters looking at her and showing shock they couldn't speak.
‘His Dad is the same, which is why I knew he'd make a good husband. He hates me busting his balls but he let's me because he loves me. Now that he's got a son who has tough balls we can all have some more fun. But Dan sweetie. Your balls are definitely tougher. Much tougher.’ She slaps my face softly as she compliments me and my hard cock twitches in appreciation.
‘What shall we do with him now Mom?’ Stephanie asks in anticipation. It was clear from the look on all three women's faces they wanted to explore my limits.
‘Momma’s gonna sit on his face as you girls stand on his balls. One of your boots should easily fit on a nut each. Let's see if you can make him scream and cum at the same time? Might even help me cum as well.’ Dee laughed at her own joke but she was hoping it could happen.
Without warning Dee launched a kick hard into my balls. I just managed to remove my hands in time. But before I could clutch my now aching balls again Samira did the same and slammed a hard kick into my balls. Just as I was about to drop Stephanie delivered a final kick hard into my balls and I finally fell to the ground.
Dee easily managed to plant her juicy thick ass onto my face as she pinned my arms to my side with her boots as she straddled me. I felt her ass slowly push down on my face. I was barely able to breathe but I felt my legs then suddenly being pushed apart and two boots pressing my swollen balls towards my chest.
‘Arrrggghhhhhhh’ I screamed into Dee’s ass as I felt the full weight of both Samira and Stephanie stand on my balls. My cock was pressed against my stomach with nowhere to do as both crushed my balls beneath their designer boots. Dee was absolutely right. I was going to scream and cum at the same time as I felt the unmistakable feeling of cum rising to the surface.
‘Now long to wait girls, he's practically at the surface.’I heard Dee tell her daughters as both Samira and Stephanie laughed and leaned on one another to support themselves.
‘Arrrrghghhh’ I continued to scream hard into Dee’s ass as I felt myself blow my load all over my chest.
‘Good work girls. That was great to watch. And his screams have made me horny again.’ Dee climbed off me but instead of getting up she wrapped her legs around my neck and locked me in a neck scissor hold.
‘Now it's my turn to cum sweetie. Girls, I want you to kick him in the balls for me. Not full force yet, but don't stop till I cum.’ Oh shit, this wasn't going to be fun.
‘No worries Mom. Come on Steph, let's enjoy ourselves.’ Without another word I watched as both women stood between my stretched legs and positioned themselves. It was clear Samira wanted to kick me more as she had a look of smug satisfaction on her face. Stephanie herself looked content. Once again Dee’s boots blocked my view of my own nuts as both began delivering hard accurate kicks into my poor battered balls. My hands gripped the thighs of Dee’s boots as I tried to relieve the strain around my neck. My view of her boots at the end of my chest made my cock hard once more. I heard Dee moan in pleasure as I began to scream and groan from the pain of the girl's strikes. The pain was horrific as they slammed in their kicks hard, but it was like my balls were becoming more numb, it didn't hurt like before. I could hear Dee put her fingers against her pussy and began stroking it. With her jumpsuit she wasn't able to slip them inside so she had deliberately made sure it took longer to climax.
‘Keep going girls. Now permission for full force. Hold nothing back. I'm nearly there.’ Dee quietly issued her instructions to her daughters as she became lost in her own oncoming climax.
‘Argggghhhhhhhh’ I couldn't hold my cries of pain in any longer as Samira and Stephanie began slamming obscenely hard kicks into my balls. I was feeling Dee’s thighs grip tighter around my neck. One last kick from Samira's brutal but beautiful boot was delivered and suddenly I heard Dee moan loudly as she began to climax. It was the last thing I heard as her thighs gripped too tightly around my neck and I passed out from the sheer power of her gorgeous thighs.
I woke up minutes later, still on the floor where I had been when I passed out. But it was quiet. For a minute I thought I was alone and I took a moment to regain my sight and senses and check my balls were still there. It was then I heard her voice.
‘Don't worry, they're still there.’ I was suddenly frozen in fear. Of the three women she was the one I feared most. I felt she was the most hostile towards me. The one who didn't show any care or emotion towards me. She stepped in front of me so I could see her. When I saw her my mouth opened in shock.
Standing completely naked aside from her boots and gloves in front of me was Samira.
‘Ever since I first saw you at the wedding I've wanted to fuck your brains out. I couldn't understand why, I haven't ever felt an attraction towards anyone like that. But one look at your huge cock today, seeing your balls of steel first hand. I now know it was fate.’ She stepped closer towards me and placed her right boot sole across both my swollen balls and pressed down hard. My hand gripped her boot instinctively as she began to grind my balls slowly.
‘So, you've got to decide one final thing. Do we fuck right now? Or do my boots continue to fuck your balls up until you understand, one way or another I'm still going to fuck your brains out?’ She raised her eyebrows up as she waited for me to answer.
‘One one condition?’ I quickly replied.
‘What's that then?’ Samira said apprehensively, wondering what I was about to ask.
‘You're keeping these boots on.’ I stroke it as she continues to grind my balls, although much more gently now as she realizes the conversation is going the way she wants it to.
She laughs aloud. ‘Deal, these boots are staying on all night baby. Only if you promise to worship me as much as you do my boots.’ She continued to laugh.
‘Deal.’ I laugh back as she finally removes her boot from my balls and pulls me up. She takes my hand and we quickly rush to my bedroom.
It was going to be a long night!