FLR Diary – My First Entry

Welcome to the beginning of my FLR diary. I’m not starting from the beginning of the relationship – that was years ago and is another story for another post, maybe. I’m going to begin pretty much where we are now and start writing from Subbie’s last humiliating orgasm and the start of his current lockup period. Some entries will be detailed accounts of particular incidents, some will be quick updates. 

 

Diary Entry 1

I decided it was time to torture my little worm since I had allowed him to be unlocked for a few days and was planning on re-locking him.

Because I had let him believe he ‘might’ be allowed to have sex with me, and ‘might’ be allowed to cum, he was desperate to begin, but he knew better than to pester me. He patiently waited while I took a while getting ready for bed. He knew of course that any chance of sex or cumming wasn’t going to arrive without him being utterly degraded first. 

When I was finally ready, I climbed onto the bed where he lay waiting. He was anticipating a torturous tease, but I knew that he wouldn’t be expecting what I had planned. “What are you thinking?” He asked nervously, taking in whatever evil smirk may well have been giving something away about my plan. But I ignored the question and leaned over him, kissing his neck. His moan of pleasure let me know he was unable to resist and would be simply letting me do what I wanted without answering his questions tonight. I worked my way down to his chest noticing his breathing start to quicken. I lifted his hand onto my neck signalling him to stroke me in the places I like. His nipples hardened against my tongue and I took in the sight of his totally helpless little submissive eyes as I let my hand reach down for his already hard, but tiny, cock in his panties. He gasped as I touched it on the outside of the panties and I began to rub myself on his smoothly shaven thigh between my legs. He could feel my arousal and I knew it was affecting him as I squashed his little thing with two fingers. He was squirming and moaning now and told me that he was close already. I laughed and said ‘Already? Your torture has barely begun!’ His reactions to my hints – exasperated, fearful, conflicted moans – only fed my need to torment him even more and I reached inside his panties to touch his nub. He didn’t know it yet, but I wasn’t’ rubbing in lube. It was numbing cream, to deny him the full pleasure of what I was about to do. As soon as he realised he questioned me again, and I explained that I didn’t want his useless little thing going off uncontrollably like it used to – I humiliated him over what he used to be like when we were teens and he could barely kiss me without making a mess in his skinny jeans. I edged him faster and harder with my two fingers, loving how hard it was for him to resist, until he twitched hard and I knew I need to stop. I slowed my finger rubbing, letting him compose himself while I concentrated on how good it felt rubbing on his smooth thigh, and his hand stroking my neck, chest, sides and leg. 

Once he had stopped his whimpering I got onto my hands and knees, pulled him up by the hand to direct him behind me and started to tease him with my bum, rubbing it against him until he started moaning again. He complained, saying how desperate to cum he felt, after 3 weeks since his last humiliating and unsatisfying anal milking. I told him he wasn’t allowed to even mention his own orgasms, or lack thereof, until I had cum as much as I wanted to. I told him to put on one of his extra thick condoms on and fuck me. He rushed to carry out the order as if afraid I might change my mind before he had the chance. I sadistically began a sentence with ‘actually now I think of it…..’ his eyes shot over, panicked. ‘You had better put two extra thick condoms on’. With a groan he rushed even faster to finish the task and pathetically scrambled over with his stiff little nub. Then, after seeking my final agreement, he slid it inside me. I remained still and gave no reaction to his tiny thing. I could sense his humiliation rising as he remained silent. I arched my back and leaned into him, laughing at the almost undetectable feel of his throbbing. I told him to try to fuck me and make me cum. He tried his hardest but it felt like nothing, and I let him know as I laughed, telling him how impossible it would be to make me cum, and that I knew how it was already getting impossible for him not to. He tried to look away but I made him look down at my bum, in my crotchless black lace thong knowing he’s in love with the sight of it. Then I made him touch it too. He couldn’t cope and had to pause from his pathetic nudge-fucking every few seconds and try with all his might to hold it in. I told him I wanted him to feel me cum while he couldn’t and he almost died when he saw me reach for the wand vibrator. Of course I was going to need something else if there was any chance of me cumming, and he knew it. I put it between my legs and turned it up, letting myself moan with pleasure. I told him I wanted him to keep trying to fuck me but he couldn’t by this point and he begged me to stop. He was frozen still just gasping and pleading with me, so I began to move as he tensed up completely, just repeating ‘oh my god, oh my god, oh my god, please, no, no, no, I can’t!, I can’t’. But I knew he could take just a little more so I began to move my hips in fast, tiny thrusting movements, enough to drive him crazy but not enough to slip off his tiny cock. 

The vibrator was starting to feel really good now and all his desperate yelping was getting me close. I let out my moans and told him, as I got closer, that this is the only way he’d feel me cum, on a vibrator while he held it all in. My vagina was tightening now and I knew he’d feel that even through the cream and condoms. I could feel the orgasm coming  while he was still flailing behind me, a total gasping mess. And I could now start to feel his denied little thing throbbing like mad. ‘You better not fucking cum while I do’ I managed as the building orgasm reached almost tipping point. I turned the vibrator up one last time and the sound of it and my own moans almost drowned out his pleading behind me that I was now completely ignoring, consumed by the approach of my own orgasm. After a long, hazy moment right on the edge, it hit me hard and suddenly, making me convulse. He knew the rules at this point – he wasn’t allowed to let his tiny thing slip out as I came, and he just managed it as the waves of pleasure rocked me. He held it in like I knew he could, just. Years ago, this would have been impossible and he would have exploded inside me from the sensation of my vagina contracting in orgasm and the sight and sound of me cumming, but my training had changed that. 

As my orgasm subsided, but my arousal didn’t, I slipped off his humiliated cock and lay on my back with the vibrator, lowered now to a more comfortable speed. He was still there on his knees, a pitiful sight, pink panties around his thighs, tears in his eyes, his small cock slowly softening and the two condoms full of pre-cum slipping off his denied little nub. I ordered him to take them off and suck out the contents which he did eagerly as I lay back on the comfortable bed, laughing and vibrating myself. When he was done with that pathetic display I made him get my favourite dildo and first compare it to the size of his minuscule cock. I told him he needed to now fuck me with something big enough to make me cum properly. He pushed it inside me and I felt it instantly giving me what he had failed to before, that wonderful feeling of being filled, of it pressing and squeezing past my G-spot. I could feel I was going to cum again soon. I pulled him up by the hair so he was face to face with me, his hand still reaching down to pleasure me with the dildo. He looked at me with complete acceptance of his lowered, humiliated state, and with total love and adoration for me. What a beautiful thing I had created of him, I thought to myself. I had to kiss him, biting his lip and neck, as he knew to get steadily deeper with the dildo pushing me closer. I could feel him throbbing on my thigh. I reached down to tease him and pulled him up higher. His moaning started up again as he realized he was in for more. I guided him up higher so his nub was millimeters from the other side of the buzzing vibrator I held against my clit. He let out another ‘oh my god’ as he worked out my plan and I looked up at him with my fake sympathetic eyes and then laughed cruelly. I made him push the dildo inside deep enough that I could cum from just rocking myself on it and I made him leave it as I pulled him closer. 

Touching his cock on the vibrator, even with the numbing cream, we both knew he couldn’t stop himself if it was held on. Squirming he gripped the white bedsheets and gasped as the end of it was held on the buzzing machine. I began to rub on the wand, with the dildo inside me I could feel myself getting close. That’s when I decided I wanted to cum together. I reached down for the panties around his thighs and pulled them up quickly as I rocked on the dildo and gnawed his lips, neck and his sensitive nipple. He knew what it meant to have his panties pulled back up over his little thing now. I didn’t have to speak – he knows he doesn’t cum on me, he knows that *if* he is ever allowed, it’s in his panties.  After years of conditioning just having them pulled up and his nub tucked back away during a torture session makes him writhe and beg – it could be that he cums, it could be that it’s the end and he never knows which. ‘Please, please, please!’ he said as he frantically humped the vibrator that was between both our legs. I used the panties to pull him harder into the vibrator, knowing that pulling them was working to crush his tiny cock and balls and squeeze his perineum. His desperation started to push me closer to the edge, his humping the vibrator was pushing it into my clit and the motion of us rocking together made the big dildo inside me press repeatedly into my G-spot and sensitive areas above. I could feel myself about to cum and I began making demands. A month locked in your smallest metal cage – ‘YES!’. Without any orgasms at all – ‘YES!’

I couldn’t hold back my own orgasm any more and I bit down on his nipple, pulled him by his underwear into the vibrator and rocked hard on the dildo. ‘Make a mess in your panties for me’, I said with my mouth around his nipple and we both came at the same time, my orgasm blissfully satisfying – intense vibration, a big dildo pressing in just the right spot and my ruined wretch melting on top of me having agreed to further desperation and sacrifice. His orgasm was utterly humiliating and frustrating having just fucked me and held it in, only to cum miserably in his panties. He knew to pull away from the vibrator at the last minute as well to ruin it. I know he felt only his crushed cock and balls in those tight, pulled up panties, his nipple being teased in my mouth, watching me cum for the second time. 

He collapsed on top of me and I told him how good he’d been for me. We lay there for a  while until the need for snacks made us move. After a midnight feast and a shower together, I made him fetch his tiny, shaftless metal cage. I put it on him and locked it up, placing the locking tool in my draw by the bed. I reminded him of the terms that he’d agreed to – locked in the cage with no orgasms for a month. He grumbled about it as we got back into bed and turned out the light, but I know it’s exactly what he needs.

 

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