Chapter 2: Caned Cruelly and Sodomized in the House of Pain

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Status: In Progress  |  Genre: BDSM  |  House: Spanking, Corporal Punishment and Slut Stories

Reads: 45

“Shortly, Matt, I am going to administer you a harsh and very painful, caning which I’ve been looking forward to all day. However, there are a couple of things I need to explain to you first, being an honest person,” Katherine stated.

When she had uttered the words ‘harsh and very painful caning’ my testicles had tingled as they had contracted with the fear – my mind had yet to sell to my body the concept of the high price of gratification that was masochism. And here I was standing in the kitchen of the empty house in Hefford Road again, a week later, and alone with Katherine - at her mercy - who was wearing a tight black sleeveless top displaying her long and sun bronzed smooth arms, her right arm being the one that would soon be instrumental in the infliction of severe pain upon me.

“Okay, Matt, you can sit down for a minute, and would you like half a glass of water before we start as it’s going to be tough on you, really tough.”

“Um, yes please.”

She walked a couple of paces over to the sink, whilst I admired her long legs under her snug fitting blue jeans, before selecting an up turned tumbler from the draining board and half filling it from the cold tap. She then plonked it down on the white mica covered surface of the table in front of me.

“Anyway, Matt, there’s a few things I want to talk about and I’m going to be totally frank.” She took in a deep breath and continued: “One of the things that I’ve wrestled with psychologically, apart from my sadism, is my gender. Biologically, I’m a woman through and through but I want, no, need to fuck as a gay man.”

As she had opened up about all this, I immediately knew that she sought to sodomize me, but I waited for her to finish – I’m a polite and respectful guy.

“The fact of the matter, Matt, is that I contemplated cross-dressing, becoming… trans… however the reality is that I could never carry it off… I would look ridiculous… I would feel ridiculous. People would whisper behind my back: ‘It’s a woman in a suit, who does she think she’s kidding?’. Embarrassing. Humiliating. It would be like Kim Basinger in Nine and a Half Weeks where John, I think that’s his name, and played by Mickey Rourke, gets her to dress like one of the guys. Doesn’t work. It would also attract undue attention. So, when I self-analysed I realised that I wanted to punish as a woman, become aroused as a woman but have sex like a gay man. I admit that it’s bizarre. Very bizarre.”

Gobsmacked, I gulped down the last of my water.

“Practically, Matt, what this means is that I’m going to give you a good thrashing as me and when I’m wet enough, I’m going to shag you up the arse with a strap-on till I come. However, I will blindfold you because for you to see me in ‘man mode’ will ruin the fantasy. I hope that makes sense.”

Katherine then fished out of her handbag a strap-on and held it up in front of me.

“As you can see it’s quite realistic, and it’s never been used on anyone else - I hope you feel honoured, haha. Basically, when I thrust, part of it moves against my clit and brings me to orgasm. It’s not that big so shouldn’t damage you and its texture is as near as damn it the same as a real penis. The only slight issue is that it smells a little like latex. Right, that’s pretty much all I need to say. I hope you’ll agree to what I intend to do to you, Matt. If not, it’s a free country, and you can walk away.”

I didn’t think about it and just promptly consented - I sought to submit to a strong woman and be punished by her. Her wish was my command, and I was a lucky guy.

After I visited the loo, she told me to go upstairs and strip off - which I did. As I waited for her, a potent cocktail of fear, arousal and excitement coursed through my naked body and my cock became achingly hard.

A few minutes later she breezed into the bedroom with the strap-on in one hand and a camcorder affixed to a tripod in the other.

“I’m going to film your caning, Matt, as I sometimes like to review a session. I won’t show either of our faces and I’ll switch it off before I fuck you - I know you won’t mind. I now want you to get onto the mattress and lay face down in the centre,” she ordered.

I complied and suddenly noticed the handcuffs on the thick wooden poles of the headboard. She then came over leaned above me, her cloying fragrance, Chlöe, momentarily wafting over me, and deftly and gently pulled my wrists into the handcuffs before clipping them shut. I was now on my stomach and stretched out with my arms secured to the headboard, somewhat anxious, and with my cock erect beneath me.

I heard her open and shut the wardrobe door prior to saying: “Okay, Matt, I have in my hand a thin whippy cane. I’m going to give you about hundred strokes across your bare buttocks. I’ll give you fifty from this side of the bed and then move round to the other side. I’m not going to pussy around – they’ll be hard strokes. Try not to move around too much. Oh, and if you beg me to stop then you and me will be… finished.

I murmured, rather cornily, “Yes, I will totally obey, and won’t let you down.”

The first stroke was agony, it stung like hell, and I had endured the pain resolutely in silence. A few seconds later there was a whoosh and a crack as the second one impacted across my posterior – it was agony and I had blown air through my gritted teeth. Suddenly I didn’t want to be there suffering. What kind of a fool was I? I promised myself each time that each stroke would be the last, and that was how I kind of got through it. After a few minutes I could feel that my face was flushed, and I was sweating profusely. The flesh of my buttocks seemed as though it was being shredded in between the spikes of agony and I could now hear myself yelping with each cruel laying on of the bamboo. It also took me a while - time distorts during a severe thrashing - to figure out that she had swapped sides and was now beating me from my right side. The caning then strangely became distant, remote as though it was happening to someone else, a weird quasi-euphoric state in which I hated yet also paradoxically embraced the pain…  

And then it was over. A blindfold was swiftly wrapped over my eyes, and my thighs were being pushed apart by strong hands. I then felt myself being penetrated with a momentary and unpleasant sensation of being split apart which quickly passed being replaced with an odd feeling of crapping in reverse. As she powerfully thrusted, my cock which was still hard rubbed on the fabric of the mattress underneath causing me against my will to ejaculate. ‘Oh, God,’ I thought, ‘she’ll be so disappointed and cross with me.’

A few seconds later she came herself letting out a groan of intense relief.

Minutes later, I was released from the handcuffs and the black fabric blindfold removed.

“Old Freud was totally right – pleasure is indeed the discharge of tension. You can get up now… what the hell is that on the bed. It’s bloody spunk, Matt, you dirty fucker. I don’t remember giving you permission to climax—”

“I’m really sorry Katherine, really sorry, it just happened, I didn’t plan it, I tried to stop it.”

She slapped me hard across the face – it hurt both physically and emotionally – before angrily shouting: “You’ve seriously let me down, Matt, you don’t disobey me and get away with it. Now, get out of my sight, get dressed and get home. In a few days I’m going to send for you and punish you for what you’ve done – you need to be taught a lesson. Don’t fuck with me, Matt!”

I’d cautiously looked up at her face which was as much reddened with anger as it was exertion from the beating and the sex and was about to apologise again but she’d cut me short with a glare and had re-stated coldly: “Just get out.”

I’d dressed as quickly as I could and had then gone downstairs before letting myself out into the cold winter evening, wondering if it was all over before it had begun…


Submitted: November 13, 2022

© Copyright 2022 Matt Triewly. All rights reserved.

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