Utterly Ruined!

Tonight Mistress had a lovely orgasm on my tongue, after which she got me nice and hard before mounting my cock. She was wearing a vest top again, and like I described before she lifted it up to expose her bra. Needless to say I eagerly begged to see her gorgeous breasts and Mistress pulled her bra down to allow me to cup and suck her tits as she rode me.

Eventually Mistress dismounted and knelt beside me stroking my slippery, wet cock. After some stroking I told Mistress that I was close and she stopped, telling me that she wasn’t going to let me cum today. But then she changed her mind and stroked me some more, asking if I was really close. She loosened her grip and it became clear that the only orgasm I was getting today was going to be ruined, if that.

Mistress gave me a few more proper strokes before loosening her grip again and slowly easing me over the edge. I think it was definitely the most frustrating ruined orgasm I’ve had yet. I was trying so hard to cum, and it felt like the pressure was so great that even Mistress’s delicate stroking would result in an initial huge spurt of cum, but it didn’t at all. Mistress continued her feather light strokes throughout but my cock merely leaked a huge puddle of cum without a single ‘spurt’ in sight. It was a perfectly ruined orgasm, and afterwards Mistress fed me quite a bit of cum from her fingers.

So now I’ve had four ruined orgasms and two proper orgasms to Mistress’s twenty eight proper orgasms since the start of this chastity year. It definitely seems like there’s some major progress being made here now. 

Kitty Sez "You People Are Fucked Up!"

FEMDOM SESSION 23rd June 2016

Well, it finally happened… after 5 years and nearly three months, I finally got to my 100th orgasm (since full time chastity began), and I am happy to report that there was nothing remotely disappointing about it whatsoever!

My previous chastity record was set in February and stood at 56 days, and now just a few months later it’s been beaten again and now stands at 62 days. If I remember correctly the previous record stood for nearly a year (or maybe longer) so I’m really pleased that Mistress is not giving me an easy time of it between records now and I hope she’ll be pushing me again soon! 

Overall the average time between orgasms since the start of full time chastity comes out at just over once every nineteen days, but that score is skewed by the early years when I was allowed to cum a lot more regularly. If you just take the last five (proper) orgasms I’ve been allowed then the average is more like just under once every 36 days. Quite a difference. And of course, Mistress starting to ruin my orgasms more often has helped push up the numbers too. Got to love it when your Mistress tips you over the brink and just watches your poor throbbing cock leak and ache with frustration, SO HOT. 

The session began with some punishment for me, since I hadn’t managed to keep my hands of my cock. Some very stingy strokes with the whip were followed by some slaps with the paddle (felt side thankfully!) before Mistress had me sucking on her glass dildo and getting it wet for her.

She climbed onto the bed and instructed me to start worshiping her beautiful feet while she played with her favourite toy. My cock was firmly held by the Oxballs Cocksling and I was really loving kissing and sucking Mistress’s gorgeous toes and feet. Mistress had me suck her dildo clean a couple of times inbetween but finally (after what seemed like quite a while – but I didn’t mind) she had me up on the bed, where she delivered some further punishment to my backside.

After this I was tied down on my back and Mistress soon had her delicious pussy planted on my mouth. She tasted so amazing, and my cock was soon being gripped ever tighter by the Cocksling. Mistress alternated between stroking my cock while I looked up at her gorgeous pussy and ass, sitting on my face and allowing me to lick her slippery wet pussy and then sinking down onto my swollen cock and riding me.

This went on for some time until Mistress knelt beside me and asked me, if she decided to let me cum, whether I would prefer to have her jerk me off while I licked her amazing ass, to jerk myself off on her ass, or to jerk myself off over her pretty feet.

Well, that’s a tough question indeed, but I pretty much knew immediately which I would choose. Mistress told me to think about it a while, but she would need an answer later. Then she pegged my nipples, pushed a glass dildo into my ass and left me to think it over.

Even as Mistress left me I could feel the Oxballs starting to make my balls sting. I really don’t understand why it does that, it’s a shame as it really is the only negative thing I have to say about that product. By the time Mistress came back it was stinging like hell and it was music to my ears when Mistress untied me and told me to remove it.

Then it was time for me to worship Mistress R’s gorgeous pussy, which as you all should know by now I absolutely love doing. She tasted so delicious and after a while she bucked hard against my tongue. There really is nothing better than feeling your Mistress cumming hard against your tongue is there? As much as I loved being allowed to cum today, I would still always choose Mistress’s orgasm over my own. It’s a wonderful thing to feel her muscles tighten as she builds towards her climax and then buck as it hits. Wow. I fucking LOVE IT!   

After allowing me to lick her pussy and ass clean of her juices, Mistress told me to lie down and stood over me once again. She hadn’t tied me down this time and without thinking I slid my hands up the backs of her beautiful legs and squeezed her ass cheeks. Mistress gently warned me not to touch her without permission and then stroked my cock until it was hard again.

She reached back and exposed her lickable little asshole to me, and then asked me if I had decided where I wanted to be allowed to cum, if she decided to allow me? As I said, I pretty much knew straight away what I would choose, but even then it was hard to discount the other options. As much as I love licking Mistress’s ass, I have cum that way many times in our Femdom Sessions, and I can imagine that will happen again in the not too distant future.

Of the other two options, it’s been a long time since I was allowed to cum on Mistress’s ass, and I would have loved to have done that, but… I waited years to cum on Mistress’s beautiful feet, and when that happened earlier in the year it was really special. Mistress’s feet are sexy as hell, and even when she is completely naked I still find my gaze drifting to her feet sometimes, they are just so perfect. I’m just one of those guys that has a major foot fetish I guess, and so inevitably, I told Mistress that I would choose to cum on her feet.

“Interesting…” said Mistress, I’m sure she didn’t expect me to choose that. Though it’s not like my foot fetish is a secret… 

Mistress continued stroking my cock for a while and then told me to get up and get on my knees. She carried on stroking me faster and faster, teasing me with her gorgeous feet until I told her I was getting close. She told me that I had permission to stroke my cock and cum on her feet.

I can’t think of a better way to celebrate my 100th orgasm, I stroked hard and fast and felt my cock swelling and straining as I got closer and closer to the edge. And then I felt myself push past the point of no return and a huge rope of cum splashed across Mistress’s beautiful feet. As I continued to stroke more and more cum erupted from my throbbing cock, covering both of Mistress’s awesome feet with my cum. As soon as I finished cumming Mistress lifted one of her feet and I licked every last drop of cum up until her foot was clean and then started on the other one.

Sometimes when you cum after a long period of chastity it’s a bit of a let down, or it’s too intense to be pleasurable, but this wasn’t like that at all, this was absolutely perfect and I have no regrets at all about being allowed to cum today. And being allowed to cum on Mistress’s amazing, sexy feet just made it even better.

Morning Teasing!

Finally got a lie in this morning, the first day of our week off. Well it was supposed to be a week off, now it’s turned into two four day weekends for me (the trials of working for a very small company). But still, a bit of relaxation is long overdue and laying in bed at 9:30 is a rare novelty for me.

Even better though was that Mistress decided that the best way to start our holiday would be to give me some teasing. Thankfully my cock was ready and willing to participate without any help from the cock ring and Mistress stroked me for a good while before she got out of bed.

Today marks a new record as it is day 57 since my last proper orgasm. Who knows how much longer it will be? We are planning a Femdom Session on Thursday, that would make it 62. I’m hoping it will be longer than that, I told Mistress this morning that part of me wants her to just keep ruining me, but I had to admit that another part of me wants to cum properly too (although I know I will regret it afterwards).

I also told Mistress that I would still much prefer to make her cum though, if I had to choose I would always choose that. Hopefully her period will end soon and I will be able to do just that.

A Last Resort..

Maybe it’s stupid, but I always think of using a cock ring as the ‘last resort’, but I think now that I shall change this view. The other day Mistress was teasing me but my cock was kind of at 80%, it perked up a lot when she stood over me and let me worship her gorgeous ass, but then after that it kinda lost interest again.

So tonight I thought, rather than stressing about it, wouldn’t it just be better to use a cock ring? And sure enough my cock was rock hard (as I knew it would be) even though I couldn’t feel it too much (numbness issue caused by my operation). I don’t really like the idea of using a cock ring as a ‘crutch’, but I think the problem with not using it is that it prolongs the problem by creating a ‘worry’ that undermines you the next time. Surely better to use the cock ring and relax about it and the problem will probably go away.

I also firmly believe that a lack of exercise isn’t helping, as much as it pains me to say it! I’ve lost nearly a stone in four weeks just by dieting, but due to one reason and another – weather / not being able to get out at lunchtimes, I really haven’t done any exercise at all the last few weeks. Hopefully from tomorrow I should be able to get out at dinner times and do some walking.

Near the end of my teasing tonight, I asked Mistress if I could kiss her feet while she played with my cock. As I kissed the soles of her feet I told her how badly I wanted to cum on her beautiful feet again, she said that maybe I would be allowed to soon.

After this Mistress told me that she wasn’t going to allow me to cum tonight… unless I really, really wanted to. After a moment’s silence from me she said ‘I don’t think you really want to, do you?’. I said ‘I want you to decide Mistress’. Mistress decided ‘no’.

Mistress had a lovely orgasm tonight, but now she has started her period so nothing much is likely to happen for a few days. We are on holiday next week and hopefully we will be having our next session. 

A New Way to Edge!

This morning I woke up in another country…

Mistress and I were in Wales for the weekend, to see a couple of bands. We were pretty late to bed but I woke up about 7am all the same. Since we were in a hotel I couldn’t get up while Mistress R was still asleep so I dozed on and off for two hours.

At some point during this time, my hand moved between my legs and I started gently squeezing my balls. I didn’t touch my cock at all (that’s not allowed remember, and technically even if I was locked up I would still be able to squeeze my balls) but in my dozy state my cock got very hard indeed and as I continued to squeeze more and more firmly, my cock got harder and harder until I realised that I was actually getting veryclose to the edge.

I let go then, but I am convinced I could easily have made my cock leak just by squeezing my balls. I would love for Mistress R to make me ruin this way, squeezing my balls tightly as my cum leaked out… that would be super hot.

Mistress has very small hands and very long fingernails and when she usually tries to squeeze my balls what generally happens is her fingernails dig in before the squeezing really takes effect. I am what is known as a ‘high-flyer’, meaning my balls don’t hang much, so this makes it more difficult and in the past Mistress has always squeezed from ‘the front’ rather than circling the top of my balls with her first finger and thumb and pulling down / squeezing.

Maybe a little practice session is in order…   

And perhaps a more regular use of my ballstretcher might help matters too.

Ruined Again...

Last night Mistress was stroking my cock hard and fast, she turned to me and asked me how many days it had been since I had been allowed a proper orgasm. I told her it was 40 days and she said ‘Better let you cum then…’

She continued stroking hard and fast and I was guessing about 70/30 odds on that I was really going to be allowed to cum. Not so, Mistress let go and we both watched my cum leak out of my throbbing cock before she scooped it up with her fingers and fed it to me.

So having just been allowed to ‘ruin’, I’m guessing that my previous record is under threat now. That stands at 56 days, which ran from the end of December 2015 to nearly the end of February 2016. I was then allowed to cum twice in March and once in April, and that has been it since then, although I have been ruined in April, May and June. So for the first time ever my chastity year stats indicate that I have had three ruined orgasms and just one proper orgasm, that’s quite some progress!

Speaking of ruined orgasms….

I’m pretty sure most of you reading this will be aware of Mistress T’s videos and there’s no doubt her videos are some of the best you will find on the internet. Yesterday a short clip appeared on my tumblr feed (and if you follow me then you will have already seen this) and I really wanted to repost it here, but because tumblr doesn’t seem to allow this and because I can’t find it anywhere else, I can’t. Which is a shame.

So I thought I would take a few screen grabs, to illustrate what happens when her slave cums without permission. She slaps his balls once and then literally punches the cum out of his balls. I’m sure it must hurt, but at the same time, it’s fucking HOT!

Visit my tumblr at the link below and watch the whole seven second video.

http://therobertanthony.tumblr.com/