A Couple of Landmarks (Almost) Reached...

Now that I’ve surpassed my previous record of 64 days, every day is a new record, and today marks 68 days since my last proper orgasm. But seeing as it’s the 30th of August today, and seeing as I know I won’t be getting release tomorrow (because Mistress R is visiting her friend for the evening) it’s safe to assume that I will make it through a second month in a row without having been allowed to cum. That’s a first, even though my previous record was 64 days it only included one full calendar month. Also, even if Mistress let me cum on Thursday, that would still mean I went 70 days without an orgasm!

The Bank Holiday weekend being a little bit of a disaster in the intimacy department, it had been five days since Mistress had last cum. Thankfully I got to rectify that this evening and Mistress had a lovely orgasm on my tongue. Afterwards I got to worship her beautiful feet for a while and then Mistress decided it was time for my teasing.

Mistress sucked and stroked my cock and brought me quite close, but not close enough for me to have to warn her I might cum. However, just as I was thinking about asking if I could worship her gorgeous ass, Mistress straddled me and sank down onto my throbbing cock. I say throbbing because it really was throbbing, and it felt super-hard as well. I pushed my cock up inside Mistress’s very tight pussy and knew that this was going to end with me cumming inside Mistress unless we were very careful.

After a few moments the feeling of caution passed a little, and Mistress started to ride my cock. It felt incredible and ‘part’ of me really wanted her to grant permission for me to shoot inside her. Mistress pulled her lacy bra down under her beautiful breasts and exposed her gorgeous and hard nipples. Although I see Mistress’s naked body every day, for some reason she has this ‘annoying’ habit of wearing bra’s when we are actually in bed having ‘sex’, I think she does it on purpose, because she knows I want to see her gorgeous breasts…

Usually Mistress waits for me to beg for her to take her bra off when she’s riding my cock, but I think in this instance she correctly assumed that I wasn’t going to ask, simply because I was already struggling enough not to cum, without the added visual stimulus of Mistress’s sexy boobs right in my face. So instead of waiting, or even prompting me to beg, Mistress decided just to expose herself to me and let me struggle with it.

Pretty much as soon as she’d pushed her bra down, Mistress leaned forward and had me suck on her nipples, then she sat back up and started riding my cock again. As if that wasn’t enough, she then reached back behind herself and started slapping my balls as she fucked me. She must have slapped my balls about 8 times I think, not too hard, but with my poor, 68 days denied cock cloaked in her tight, silky pussy this was really testing my willpower and resolve. In fact there was a point where I thought I had not just raced up to the edge, but tipped over, but somehow, incredibly, I managed to hang on by my fingertips!

Even though it made things incredibly difficult for me, I absolutely love it when Mistress slaps my balls as she rides my cock. There are a number of ways I’d love to cum with Mistress slapping my balls as I shoot, and pumping my load inside her gorgeous pussy would definitely be one of them!

Mistress ceased the slapping, but rode my cock a little while longer, before sliding off and grabbing my cock. She gave it a few brisk strokes and then let go, leaving it quivering and desperate for more of her attention. But, save for one more slap (sadly, something of a miss-hit) that was my lot for the night.

“I’m not going to let you cum tonight,” she said. “You’re going to have to wait a few more days, you can do that for me can’t you?”

“Yes Mistress.” I replied.

As usual, part of me wants to cum and part of me really doesn’t. But as always, I’ll have to trust Mistress to make the decision on my behalf. Given that we’re in new territory now I’m kind of expecting her to let me cum anytime soon, but of course part of me hopes she just keeps ruining me, after all 100 days isn’t that far away, is it?

DO YOU THINK I'M EVIL? (Written August 2016)

“I have a question for you slave and I want you to answer honestly…”

Karen’s hand moved up and down her slave’s cock at a steady pace. Not too fast and not too slow, keeping him stimulated but not heading for the edge. It was far too early for that…

“Do you think I’m evil?”

“No Goddess,” moaned Dean.

Karen looked disappointed and squeezed his cock a little harder on the next few strokes.

“Really! Oh dear… that means I’m failing then, doesn’t it? After all I’m sure you said you wanted me to be ‘evil’ to you, didn’t you? You said you wanted me to be completely merciless… in fact, if I remember correctly you said you wanted me to be a totally heartless bitch, didn’t you? And I promised I would, didn’t I?”

Dean groaned in agreement.

“Don’t forget, this was your idea, you made me promise to never go back, no matter what you said, no matter how bad it got, no matter how much you begged, you made me promise to never let you enjoy a proper orgasm again, didn’t you?”

“Yes Goddess…”

“I know I’ve made it hard for you, and that’s what you wanted too, isn’t it? You didn’t want me to make it easy for you, you wanted every orgasm to be completely excruciating didn’t you?”

Dean whimpered as Karen grabbed the dildo that was protruding from his ass and gave it a volley of violent strokes, punishing his prostate and stretching his tight hole at the same time.

“And yet you still can’t quite believe that I won’t show you compassion, that I won’t show you mercy at the last second. Even though you know full well that every orgasm that I allow you to have will be ruined one way or another, as you get nearer, as your balls start to tighten, your brain tricks you into thinking that this time you will be allowed to cum properly. Over and over again… isn’t that right?”

“Yes Goddess, yes…”

“Because despite everything, you desperately want to cum properly don’t you? You need it don’t you, you need to feel that blissful sensation of your cock pumping out your cum with just the right amount of pressure and for just long enough to make it feel good… before it gets too sensitive and starts to throb and hurt.”

Dean gasped as his Goddess forced the dildo even deeper into his asshole.

“But see, when it gets too sensitive and starts to hurt, that’s the bit that turns me on the most. When you start to buck and shake and try to pull away from me, straining at your bonds even though you know you can’t escape and that I can torture you for as long as I like… that’s the bit that makes my pussy really wet.”

Karen let go of the dildo as she focussed her full attention on his cock.

“Do you even remember what it felt like when I used to let you cum properly? It’s been so long now hasn’t it, well over three years… and you know what, I haven’t missed it at all… it’s always been much more fun for me to watch you suffer. So when you ‘made me’ promise to never let you cum properly again, I could hardly believe my luck.”

Dean’s cock twitched and Karen released her grip and slapped his aching balls twice, hard.

“Don’t even think about cumming yet slave, I’m nowhere near done with you.”

Dean exhaled loudly, every fibre of his existence was focused on holding back his impending orgasm, knowing full well that failure to do so would only make his Goddess more determined to make him suffer.

“Maybe you should try to forget about it, because you know that I will never let you have that pleasure again. I made a promise to you and I mean to keep that promise… and I mean to destroy every orgasm I ever let you have again… including this one.”

Karen grabbed Dean’s swollen balls and squeezed them hard.

“And in that moment when I ruin your pleasure, either by ‘under’ or ‘over’ stimulating you, or tying a lace around your cock and pulling it tight as you cum – literally blocking your orgasm and forcing your cum back… Oh that’s one of my favourite ways, I love the sounds you make when I do it like that, it’s so fucking hot to hear you beg and howl. I know it hurts and that turns me on so fucking much I can’t even tell you…”

Dean winced in pain and Karen released his balls. She leaned forward and spat directly on to his thick, throbbing cock and then resumed stroking it.

“And in that moment… when I do that, there must be a tiny part of you that genuinely hates it… and genuinely hates me too.”

Karen’s hand climbed to the top of his aching shaft and curled around his cockhead, palming him mercilessly.

“But you can’t ever really hate me can you? Because after all, I’m only doing what you asked me to do aren’t I? And I’m only doing that because I love you and I want to make this as good as I can for you…”

Karen switched to teasing the tip of his red, pulsing cock with one finger, on the sensitive spot right under the head.

“And the best way to make this as good as I can, is to make it as unbearable as possible isn’t it? Because we both know that’s exactly what you crave. Isn’t it?”

“Yes Goddess, I love being your toy…”

Goddess Karen chuckled to herself as she used her free hand to squeeze Dean’s huge, aching balls.

“Do you want to see my gorgeous tits slave?”

“Yes Goddess.” Begged Dean, his voice almost cracking as he spoke.

“I know you do,” chuckled Karen. “And I love showing you my beautiful, soft tits because seeing them only makes your cock harder and more desperate to cum doesn’t it? And believe me slave, I want it desperate. I want it so fucking desperate and painfully hard for me, because I know the more you want to shoot, the more you ache for release, the more intolerable it will be when I completely annihilate your orgasm…”

Dean’s cock twitched hard in her hand and Karen laughed again as she pulled her breasts free from the confines of her tight T-shirt.

“Oh I felt that. You are so fucking bad. I know you think you want to cum, but your cock knows the truth. Your cock gives you away every time… honestly, it just grew half an inch when I said I was going to annihilate your orgasm. Oh, and there it goes again, pulsing, twitching, aching for my gorgeous tits… you want to shoot on them don’t you, you love the sight of my beautiful big tits dripping with your cum don’t you? But you know that it never turns out the way you expect.”

Karen leaned forward and rubbed the tip of Dean’s tormented cock against her left nipple.

“You still cling to the idea that one day I’ll relent don’t you? You still think that one day I will decide to let you cum properly and enjoy it like you used to.”

Dean’s body arched as he felt the soft, silky skin of Karen’s breast against his prick.

“Sometimes I’ll even say it, won’t I? Sometimes I’ll even say ‘One day I’ll let you cum properly’… but we both know it’s a lie. I only say it to fuck with your head. I only say it because we both know your brain will cling to that thought and that even though deep down you know it’s bullshit, you can’t help but hope. Ah, hope… it’s all you really have isn’t it? The feeble hope that one day I really will let you cum properly and all this will have been worth it. And maybe I will…”

Karen’s words hung in the air for a few seconds as she teased his cock against her skin.

“…but I probably won’t.”

The pleasurable sensation from her breast was ripped away as she wrapped her hand around his cock once again, pumping hard and fast and rough, the side of her fist travelling right down and slapping against his balls on every stroke.

“Do you know why slave? Because I love it far too much…”

Dean groaned loudly, desperately trying to hold back the torrent of cum that was bursting to escape his tortured balls.

“Oh God, that’s it… suffer for me. I fucking love watching you suffer and struggle for me.”

The abuse continued for a few seconds more and then abruptly stopped. Karen moved closer, her voice dropping to a conspiratorial whisper as she lightly gripped his cock and began a slow torturous, unbearable teasing stroke.

“Do you ever think about what might come next slave? What new ways I might come up with of ruining your orgasm and denying you the pleasure you think you so deeply crave?”

Dean’s breathing was heavy, the sensation of her touch as maddening as it was light.

“Maybe it’s best you don’t, after all, a slave could drive himself insane thinking about things like that, couldn’t he?”

“Yes Goddess.” Dean’s just managed to force the words from his lips.

Karen chuckled softly in his ear, her hand continuing to barely stroke his throbbing length.

“What if I am truly evil though slave, have you thought about that? You know the cage never comes off until you are securely tied down, I made sure that you agreed to that early on. So what if I really am as ‘evil’ as you wanted me to be… and more? Could you handle that slave?”

Dean could barely speak now, such was the concentration required to prevent himself from exploding without his owner’s permission.

“What if I wanted to destroy not just your orgasms, but your actual balls as well. It would be so easy to tie you up, slip off the cage and slip on an elastrator band, wouldn’t it?”

Karen’s voice audibly cracked as she spoke those powerful words for the first time.

“Oh yes, your cock definitely jerked there. I know you know what an elastrator band is and it excites the fuck out of you doesn’t it? I’m sure it scares you too, but you trust me don’t you? You know I’d cut it off before any lasting damage was done, don’t you…?”

Karen moved away from him again and squeezed his balls hard once more, then reached for the dildo, pumping it into his ass in time as she stroked his reddened, angry looking cock towards an unavoidable, excruciating edge.

“Look at those huge, swollen balls… they would look so good banded tight.”

Dean let out a strangled whimper which only pushed Karen to go further with her fantasy talk.

“Can you imagine how it would feel slave, having that tiny band of rubber wrapped tight around your balls? Making your cock harder than it’s ever been in your life? Wouldn’t that be something slave, wouldn’t it be worth the risk?”

Though he hated to admit it, the thought of her banding his balls like that pushed him hard to the edge and his breathing was coming in huge uncontrollable gulps as he tried desperately to hold back for her. Sensing how close he was, Karen relented and let go of the dildo, but left it plugged deep inside him.

“Maybe if I knew you were really, truly terrified, maybe then I could find it in my cold, evil heart to allow you to cum properly… just one last time? What do you think slave, what do you think it would feel like to cum with your balls banded so tight? Do you think your cum could even escape?”

Dean’s body was starting to twist against his bonds now, as the need to find release approached critical levels. Meanwhile Karen’s free hand moved between her legs and her fingers began to stimulate her sodden clit as she revelled in her slave’s torment.

“God, I so want to try it slave, I want to see you struggle as your balls try to pump out every drop of pent-up frustration… fuck, I can’t tell you how wet thinking about that makes me slave, maybe I really am just as evil as you wanted me to be.”

Karen’s hand was working like a steam hammer on Dean’s cock now, as she pushed him ever closer to the point of no return. Her other hand was becoming more insistent on her own clit and she felt her own orgasm beginning to build.

“You know it’s going to hurt don’t you… when I cut the band off and the blood rushes back into your balls? I imagine it will be like when you take a nipple clamp off… only a hundred times worse. Who knows, maybe after the first few times you’ll start begging me to leave it on, because you won’t be able to face the pain. And when you do slave, if you beg me hard enough, then one day maybe I will…”

Dean’s groaning was growing in intensity, his cock looked impossibly red and hard and Karen knew he couldn’t possibly last much longer.

“You’re getting close aren’t you slave, you can’t help yourself can you? The thought of me destroying your balls makes you fucking horny too doesn’t it slave? You want to cum so bad don’t you… Well come on, show me how bad you want it, shoot your fucking cum for me while you still can. Come on, I want to see it, I want to see it now. Right now slave, do it, shoot your fucking load for me…”

As the moment of release drew closer, Dean began to babble incoherently, begging and pleading for release and an end to his torment. But Karen continued stroking, harder and harder, faster and faster until she saw the first drop of cum erupt from his angry looking, crimson cock head.

“That’s it slave, shoot it for me, shoot your cum all over my gorgeous fucking tits…”

Karen pumped hard and fast as ropes of thick cum splashed her skin and dripped down onto her naked thighs. On and on, way beyond the point of pleasure, way beyond the point where Dean wasn’t coming anymore… this was no longer about him, this was all about her and the pleasure she took from hurting him and ruining his every release. His animal like cries and muffled pleas for mercy pushed her crashing over the edge, until ultimately she lost her grip as she collapsed, spasming as she sank to the floor, her pussy gushing repeatedly as she succumbed to the hardest orgasm she had ever experienced in her life.

A Great Afternoon...

I can’t quite believe the weekend is nearly over, it has gone so fast! Fortunately Mistress and I managed to make time to go to bed this afternoon, I didn’t realise it had been since Wednesday since Mistress had her last orgasm. Well Mistress certainly had a very lovely orgasm today and as I was kissing her feet afterwards I was looking up at her as she lay on the pillows with her eyes closed, completely sated and I just thought how completely beautiful her pussy looked. It was so wet and pink, it almost looked like I had cum inside her. Just a totally gorgeous sight…

After that Mistress teased me like crazy, with some very hard stroking and ball slapping. At one point Mistress edged me and the teased my cock with her tongue and mouth and actually thought I might have ruined into her mouth. I don’t think I did, I’m sure she would have told me… but it really kind of felt like it. Absolutely incredible teasing though, and she left me absolutely rock hard and throbbing like crazy.

It’s been 59 days since I was last allowed to cum properly, and this is only the second time I’ve got this far. Strangely I seem to have gone past the stage where I feel like I could cum really easily, and Mistress really pumped my cock today and I took it easily. It’s quite interesting these little phases that you seem to go through as the days add up.

What with one thing and another Mistress and I decided to delay our next photo session until next week (which is a Bank Holiday here in the UK), so we will be out with friends on Friday night, off lingerie shopping on Saturday, Femdom Session on Sunday and photo session on Monday. Sounds like an awesome weekend don’t you think?

More Feedback and a Surprise Ruined Orgasm.

I have two more feedback’s on Literotica, both favourable…

JOHNNY ROTTENCROTCH: Nothing short of fucking awesome! Now *THAT* is a milking story. I’d love to see more of Karen torturing her slave’s cock!

And…

FASfan: Wowee! This was a terrific story – thank you for posting it for us to share. Five stars and favourited!

So far 1208 people have read ‘Do You Think I’m Evil’ (not bad for one day!) and it has a score of 4.5 / 5.0.

— — — — —

Mistress took me completely by surprise tonight. After I made her cum with my tongue she knelt by me and started stroking my cock. When I was hard she sucked and slapped me and then straddled me and sank down on my cock, facing away from me. After a while she turned around and straddled me facing forward and I begged her to remove her bra and allow me to see her gorgeous breasts.

Unlike last time I felt quite in control and like I could last a while (I wouldn’t have begged to see Mistress’s breasts otherwise!). Mistress started to ride me quite hard and I thought, ‘Okay, she’s going to have me cum inside her and then lick her clean…’.

But no, I was wrong. After riding me for a while she moved off me and started stroking my cock hard and fast. It didn’t take long for me to warn her that I was getting close and she kept stroking just as fast, but moving closer so that her beautiful breasts were right next to my cock. She said something about letting me cum, and she was pumping so fast and hard it never even occurred to me that she was about to ruin me again.

But that’s exactly what she did, and for the first time she ruined me onto her breasts and then had me lick them clean, which was sooo hot! I was just a bit thrown because I wasn’t expecting it at all. Still, surprises don’t get much better than that, do they?

After I had licked Mistress clean I thanked her for allowing me to cum on her breasts and lick them clean. But she made me thank her again, feeling that I should be thanking her for ruining my orgasm too. Needless to say I did as she asked… 

Greatly Exceeding Expectations...

As of today, Mistress has had 40 orgasms since the start of our sixth year of 24/7/365 chastity (on April the 1st 2016). By contrast, I have had 7, which gives a standard ratio of 5.71 to 1, pretty much in line with the ratio of the last few years. The difference this time though is that of those 7 orgasms, 5 have been ruined. Which means that instead of 7 – 40, it’s actually 2 – 40, giving an easily calculated ratio of 20 to 1 in Mistress’s favour!

This is quite incredible really, given that it’s been a long term goal for me that Mistress should have 10 orgasms for every 1 that I am allowed. We haven’t so much surpassed that goal as annihilated it. Which is great! But still a huge surprise…

Of course the main reason for this is that Mistress has recently begun to embrace the ruined orgasm fully and as we can see above, it’s not so much that she has let me cum much less often, it’s just that the greater proportion of those orgasms have been ruined.

If you read my post the other day about the letter I wrote to Mistress R at 4am last weekend, you’ll know that I told her that I was willing to leave it fully up to her in future as to whether she was going to let me cum or not. Now, some of you may have thought that was an odd thing to say, because after all Mistress already decides when and how I cum and has done for the last five years and more.

This is true, but it seems unreasonable to expect that Mistress would push way beyond my current record of 62 days without at least some comment from me. The point of that part of my letter was to let her know that I am ready to be denied for as long as it pleases her to do so. If she wants to ruin every orgasm for the next year, the next three years, five years… whatever she wants is okay by me.

In truth, do I really think Mistress is going to jump from 62 days to permanent (or semi-permanent) denial – no, of course not. And I’m sure there’s some of you out there who are maybe chuckling to themselves and thinking ‘this guy has no idea what he’s talking about’. Also, fair enough – I don’t know what it’s like beyond a certain point. But I do know that I love being super horny and aching for my Mistress, and as such I felt it was right to tell her that if she wanted me to I would be happy to go a very long time without a proper orgasm.

Of course, I’ve read enough chastity blogs to know that the best laid plans of mice and men etc etc… and that’s why I wouldn’t really want Mistress to say that I am going to be denied for any fixed period of time. I wouldn’t want her to feel bound or constrained by some arbitrary ‘rule’ or ‘goal’ that she had set. I fully realise that there may come a day when she wants me inside her and in the moment, when I give her warning that I’m close, she might decide ‘screw the chastity’ because she wants me to cum inside her. And again I wouldn’t want her to lose that option. This is supposed to be about her pleasure, and if she wanted me to cum for her pleasure then that is her prerogative. Statistics and numbers are all well and good, but they should reflect reality and not dictate it, the last thing I would want would be for Mistress to make me wait 350 days to cum and then feel like she couldn’t exercise her power until we made it to a year.

That’s why we abandoned the ‘dice’ chastity early on. It has it’s uses in that in the early days it can be useful to take pressure off a new chastity Mistress, but ultimately ‘dice’ chastity isn’t empowering the Mistress at all, since she is following it’s ‘rules’ just as much as her slave is.

Anyway, like most guys in my position, I have come to feel VERY differently about proper orgasms than I once did. Sure I crave them, when Mistress is edging me I want to cum very, very badly… make no mistake, that primal urge does not go away. And my last proper orgasm (June 23rd) was absolutely amazing, shooting all over Mistress’s beautiful feet and licking them clean was AWESOME.

But with a clear head, if I was given the choice to stroke and cum on Mistress’s beautiful feet, or stroke and ruin on Mistress’s beautiful feet I would probably choose the second option. Of course the difficult bit is the ‘clear head’ bit, because when you are stroking your cock with one hand and holding your Mistress’s foot with the other there is no such thing as a clear head.

Which is why people like me need a Mistress to decide for us (and why some of us need locking up – for our own good!).

I still think about that from time to time, but then I remember how ridiculously badly my CB3000 fitted and how I could barely get my jeans on over it. It’s frustrating, because I love the idea of it and I’m sure it must be amazing to go to that level of control, but there you go. Besides, Mistress wasn’t overly keen on the idea, not that we’ve talked about it for a long, long time.

I still have my CB3000 in a drawer. Maybe I’ll give it another shot sometime.

So Close to a Ruined / Slapped Orgasm..

This evening Mistress had another lovely orgasm on my tongue, and afterwards she teased my cock pretty close to the edge. Mistress is definitely embracing the ball and cock slapping now, and that is damned hot!

The best part of tonight’s teasing was definitely right near the end, Mistress was stroking me hard and fast with one hand and repeatedly slapping my balls with the other. That was absolutely incredible. I was seriously wondering if Mistress was going to let me cum (but continue slapping my balls as I came), or if she was going to wait until I edged and then keep slapping my balls until I ruined… I’m sure either of those would have been phenomenal.

But in the end, Mistress took me really close and then left me hanging, throbbing and desperate… which of course is (and always should be) her choice. I really wanted to feel her slapping my balls until I either came or ruined though. Today marks 48 days, I think this is only the third time I’ve got this far (I think), so of course I’m going to start craving release badly.

Of course, at the same time I want to be made to wait a lot longer too… if not indefinitely  

FEMDOM SESSION 8th August 2016

As some of my regular readers will know, I am still struggling with the story that I have been writing for the last six weeks. Well not so much struggling, as it must be a week now since I did any work on the damned thing… but certainly not getting anywhere. And as I said a few days ago, for some reason my mind is coming up with all sorts of material that I really don’t to advance that project.

And so it was today. As I drove home from work I was coming up with huge chunks of dialogue, which is very annoying because I can’t write and drive at the same time! And this really was huge complete chunks of text coming to me all at once, so what I did was pull into the car park near where we live, got my laptop out and started putting it down. I did this because I knew that if I went straight home I would then get involved with doing something and by the time I got a chance to put some of this stuff down literally 5 or 6 hours would have gone by and I would be pulling my hair out trying to remember everything.

So the good news is that I have the bulk of a short story right there on the page and it’s not going to get expanded and padded out too much. This is perfect because it ticks a lot of boxes for me. I wanted to get back to writing harder material and this certainly fulfills that objective. I wanted to get something on Literotica because it’s nearly a year since I posted anything, and on top of that it gives me a bit of breathing space to work on my 10,000 word story that I’ve been toiling at for the last however long it is now.

Truth be told I might even be tempted to write another short story before I finish that one. It’s become such a ‘thing’, that I can’t even contemplate attacking it without a good two or three clear hours to get my teeth into it. I’m sure it will be good when it’s done, but it’s one of the most difficult, perhaps the most difficult, story I’ve ever written.

So I would say, watch out for a new story from me in the next few days, but recent experience has told me to be uber cautious about shit like that…

Anyway, tonight Mistress and I had our Femdom Session, and I’m pleased to report that Mistress had a lovely orgasm on my tongue while I had to choose between being allowed to cum or being allowed to worship Mistress R’s gorgeous asshole. Can you guess which one I chose? Yes, of course you can…

So I’ve not come for 46 days now and that means I’m just two weeks and three days off setting a new record. I wouldn’t be surprised if I make it either, Mistress is more and more on board with the ruined orgasm thing and seemingly less and less worried about allowing me proper orgasms.

During the session she was rubbing my poor cock against her gorgeous breasts and asking me if I would like to ‘shoot my cum all over them and lick them clean’. As if that wasn’t hot enough she then added, “…but it would probably taste better if that orgasm was ruined, wouldn’t it?”

Mistress looked absolutely gorgeous tonight, in my favourite outfit with the cut out bra panels made from straps.

I started off the session with a beating as Mistress punished me for touching my cock without permission during the time since our last session. I was wearing the Oxballs ballstretcher and I had a glass butt plug/dildo in my ass, Mistress managed to catch my balls with her whip, but that was nothing compared to the paddling she gave my ass. Ouch!

After a long time spent worshipping her gorgeous feet (while she played with her favourite dildo), Mistress had me suck it clean and then let me onto the bed. I was given some more paddling, but thankfully not quite as painful as before. I say painful, it hurt… but in BDSM terms I’m probably a bit of a lightweight. Most people would probably consider it light slapping, but to me it was quite stingy anyway.

Soon Mistress was teasing my cock and riding my face, which I adore. I hadn’t used the ball stretcher for a long time and it was really, really good. It certainly pulled my cock tight and made my cock very hard indeed. At one point Mistress straddled me facing my feet and I watched my rock hard cock slide inside her tight, tight pussy, her gorgeous asshole clearly visible as she bounced up and down on my shaft. Then I felt Mistress reach under and use my tightly bound balls to rub her clit. 

Mistress gave me some choice dialogue tonight and I’m annoyed that I can’t remember anything to share with you guys, maybe I should record one of sessions again so I can give you a word for word transcript.

After Mistress had cum (pretty spectacularly), she did that thing I really love where she puts her foot on my shoulder and pushes me back. It’s a little thing, but I’ve loved it since I saw it in a Femdom clip.

Then she stood on the bed in front of me and had me clean her ass and thighs with my tongue. Then she had me lay down and straddled my head, giving me a perfect view of her soaking wet pussy and ass while she stroked my hard cock. This was the moment she chose to ask me if I wanted to cum or if I wanted to lick her asshole.

Mistress allowed me the privilege of licking her incredibly sexy ass for a short time while she stroked my cock fast and hard. By the time she finished my cock was about as hard as it has ever been and Mistress finished the session by slapping my cock and balls a few times. I even begged her to slap my balls again and she obliged, giving me several more slaps to the cock and about three more to my balls. I absolutely loved it.

Our next session is planned for the Bank Holiday weekend, I can’t wait!!! 

Is It More Humiliating...?

It All Went Very Well in the End...

This evening I gave my ‘letter’ to Mistress R and kissed her feet while she read it. I must admit I was nervous about how she might react to some of it, but in the end she seemed to really love what I had written. Here are some parts of what I wrote:

“I am writing this at 2:40am (Sunday morning), because I feel absolutely compelled to write these thoughts down right now, and to not allow them to fade by morning. This has been such a wonderful day and reinforced how much I love and adore you and how lucky I am to spend my life with you. I really could not be happier. I have never felt more certain in our marriage and that I want to spend every last day I have with you as my wife and Mistress.

A few minutes ago you came to bed and I tried so hard to tell you exactly what I was feeling, but I simply couldn’t make the words come out. But I don’t want to let this feeling pass without telling you exactly what is in my head, because I feel it so strongly.

I know full well that you may read this and it may change nothing, that things may carry on exactly as before, and if that is what you decide as my Mistress then I will accept that and be truly grateful for it, because believe me I know and appreciate how lucky I am to be able to live as we do and to have you as my chastity Mistress.

When you came to bed I was so hard, and so desperate to hold you and feel you pressed against me, and to feel your beautiful, soft skin against my aching cock. I cannot tell you how intense it feels to be denied for weeks and to crave your touch so badly. After five years and more of being your chastity slave I adore feeling this level of horniness, and as so many others in my position have said before, though we all crave the explosive release of a proper orgasm, equally we all learn to dread it, because we all know how long it takes to rebuild this level of ache and desire.

I love that you control my orgasms, I can’t tell you how much I love that you do that for me, and I wouldn’t wish to take anything away from you regarding your power to decide when, how and indeed ‘if’. But I want you to know that I am ready and willing to give you absolute power to deny me indefinitely should you decide you want that to happen. If you were to decide that all future orgasms are to be ruined, and that I am to be left in a permanent (or perhaps a semi-permanent) state of ache for you, then I am so ready to accept that and to love and worship you for it.

Equally, I can’t tell you how badly I crave for you to be sexually ‘mean’ to me. When you slapped my balls earlier, I loved that you did it so hard. I actually wondered if you were planning to make me cum by slapping my balls, and I really didn’t want it to stop. I appreciate that it’s hard to overcome a natural reluctance to ‘hurt’ someone you love (I would find it very difficult to ‘hurt’ you no matter how badly you might ask me to) and that alcohol maybe makes it easier to let go, I know you have slowly pushed further in this area and I just want to reinforce that I genuinely love it and want you to keep pushing as far and as fast as you feel comfortable.

Also, it’s hard to quantify or explain this to you, but the non-physical side of being ‘mean’ is also a huge turn on. Even just feeling that you are enjoying slapping my balls or ruining my orgasms makes a huge difference, and that doesn’t mean I want you to ‘pretend’, but equally I want to reassure you that I love it and that I want you to let go of any remaining feelings of guilt you may have about doing it. Just hearing you say how much you love seeing my cock when it’s throbbing hard and red from being teased and whipped is like heaven to me.

As I said before, I know that you may read this and maybe you will decide to go on exactly as before, and that would still be wonderful. Please do not think I am complaining or unhappy in any way, I am 100% deliriously happy to be your chastity slave and I totally understand if you feel uncomfortable going beyond a certain point or level of this. I completely worship you and I want you to be 100% happy with everything. I just had to get this off my chest, because I so wanted to tell you all this earlier and I just couldn’t verbalise it.

It’s 4am now and I’m going to be so tired tomorrow now, but I just had to get up and write this down. Please, please, please don’t take anything negative from this, you are already amazing and wonderful and I could not love you any more than I do.”

– – –  – – –  – – –  – – –

“As I lay in bed this morning, desperately trying to get back to sleep and feeling rough in the way that you only can when you’ve seen the clock reading 4am, a million thoughts were swirling around my head. There is so much more I want to say to you and want you to know.

I wish that you could truly understand how I feel about you and how you make me feel. I know everyone is self-critical about their appearance, no matter how perfect they are to someone else, but I wish you could see yourself through my eyes. Honestly, I only have to see you sitting reading with your feet bare and I want to kiss them. I don’t want to be annoying so I don’t do it every time I see you like that (in fact I probably hold myself back far too often), but that doesn’t mean I don’t want to.

Similarly every time I see you naked after you shower, or every time you take off your dressing gown to get into bed I want to touch you and kiss you all over and make you feel adored. But again, I don’t want to be annoying and I know you might be tired or rushing because dinner’s ready at 6:30, but that’s what I’m thinking.

Even when you are jumping up and down and hot and sweaty in your sexy little shorts and vest top, you still look completely gorgeous to me and I still want to kiss every inch of your skin, taste your pussy and ass and worship your beautiful feet. I seriously would, in a heartbeat. There is not a moment when I wouldn’t drop everything to make you feel completely worshipped if you asked me to (‘told’ would be better, obviously…). I mean, honestly, I know no-one can walk around feeling worshipped and adored 24hrs a day, but that doesn’t mean I don’t want you to.

And finally, I want to re-iterate again how much I love your scent and taste. There is not a moment that I don’t want to taste you, and I hope one day you will feel comfortable in not having ‘down-time’ anymore. I want you to have complete freedom to cum whenever you want, and I feel sure you would taste just as gorgeous no matter what.”

I really loved how she reacted to this letter and I’m very happy that she knows how I feel about all sorts of things, not least that I would be happy for her to move on to either a permanent or semi-permanent state of chastity (ie – only ruined orgasms for me if that’s what she wants).

After she read this she caught up on my blog posts and unexpectedly came across something I’d forgotten about – the bit about the Elastrator… so I had to try and explain what it was, that was… slightly awkward, seeing as I wrote that I thought it was strangely erotic! Still, it’s not really the basic idea, it’s how it’s used as a tool for power exchange – such as in the video I linked to…

5/2 Ruined..

This evening Mistress R racked up another gorgeous orgasm, and most unexpectedly – after some considerable stroking and teasing, Mistress edged me and then allowed me to cum. But once again it was ruined! And boy was it ruined, it was like half as much cum as you would expect from a normal orgasm, and that’s not even taking into consideration that it’s been over thirty days since the last time I was even ruined, never mind the last time I came properly!

It really was an effort to force it out, try as I might, and Mistress wasn’t helping with her infuriating feather-like strokes that are actually more frustrating than not touching me at all. What a complete and utter….ly wonderful Mistress she is! I loved it of course (but hated it too, obviously…) 

So I really can’t believe this now, but since the start of April I have been allowed to cum seven times, but five of them have been ruined! And I’m still stuck on 100 orgasms since April 2011, while Mistress continues to add to her tally every few days. Who knows, maybe she’ll get to 650 before I get to 101?

I’m especially surprised that she ruined me tonight, given that we have our Femdom session coming up at the weekend. I shouldn’t read too much into it I suppose, but in the past I can’t remember Mistress ever letting me cum (or ruining me) in the days before a session. Should I take it that it’s now less likely than before that she’ll allow me to cum in the session, or is it a double bluff? Maybe she’ll ruin me again in the session… I guess I’ll have to wait and find out.

In a twisted way I am so proud of her though, because it really has taken my Mistress a long time to embrace the ruined orgasm, but now it seems she has taken to it, and she seems to have it down too! How lucky am I?