Have You Ever Wanted to Cum So Badly?

I began writing a post a couple of weeks ago, but I never completed it (despite staying up til 2am trying!). Eventually I came back to it and tried to rewrite and finish it off, but then other things happened which needed adding to it and after a while the original post became such a garbled mess that I gave up completely. But I feel like there were important topics in that post and I do want to address them, so I’m going to try again.

But before we get into it, I just wanted to say thank you to everyone who read my latest story ‘Gareth’s Obsession‘ and also anyone who took the trouble to vote on the Literotica page. The rating has climbed up from 4.17 to 4.48 in the last couple of weeks and it’s now so close to reaching 4.5 and getting a ‘HOT’ rating. Hopefully it will get there, but if not, well never mind. 4.48 is still a very good score.

Actually, I have started going through the writing folder on my Desktop and I’ve already pretty much completed a story that’s been sitting there since Boxing Day 2022! It was so close to being done, I can’t really understand why I left it there all this time. It’s pretty short, so nothing like my last story… but maybe that’s what I need to concentrate on for now, finishing what’s already in progress and not getting bogged down in stories that take weeks to write. This story should be posted soon, I just need to give it one more read through I think.

Oh yes, long, mentally draining stories… that’s how this post all started.

19th November 2024

Now I don’t want to sound ‘dramatic’, after all writing is my choice and I do enjoy the creative process (and the ensuing feedback, good and bad) but I have to say in all honesty that the last few weeks have been a little challenging. It’s been so long since I wrote a really long, involved story like ‘Gareth’s Obsession‘ that I’d forgotten quite what a mental strain it can be. In fact I distinctly remember writing one of my longer stories, many years ago, and it became so overwhelming that it really affected my mood in a very negative way.

Thankfully once the story was finished and posted I could also see how ridiculous that was and after that I tended to avoid writing these really long, involved stories and instead concentrated on shorter stories that I could knock out pretty much in one 2-3 hour stint. Yes I would keep refining them for a couple of days until I was sure it was as good as it was going to get, but basically it was a short term commitment that didn’t inflict too much mental strife.

I didn’t know ‘Gareth’s Obsession’ would turn into a 20,000 word story when I started it, and if I had I might not have got that far with it. I do like writing and of course there is a sense of achievement in finishing something of that scale, but the problem with a story like that is that it is always bubbling away in the back of your mind, even when you aren’t actually working on it.

It’s not simply the struggle of ‘creating’ a story and getting it just how you want it either, though that was bad enough, especially when I decided I didn’t like the names I’d chosen for the characters and had to think of new ones that were suitable for each of them and that also worked with each other*. I mean the physical ‘changing’ isn’t difficult, it’s just find-and-replace, but trying to get them to settle into the story is not that easy once you’re used to the originals and I changed three of the character’s names several times until I was happy with them.

*One of my older stories had a couple in it called James and Janie, the feedback I got for that one was that the story was great but the names made it hard to read. Reading it back I could totally see what they meant, and I wonder if this was a case of me changing the names at the last minute and simply not seeing the problem before I sent it to Literotica? Could very well be…

But it’s not just all that… there’s also the simple fact that once you embark on writing a story like this you can’t help but constantly have it in your head. Even if you’re not actively working on it, your brain is still working away, and so apart from constantly thinking about the ‘mechanics’ of it all you’re also dwelling on the ‘content’ endlessly too.

What I mean by that is, if you read a story like that and it takes up 20 mins, 30 mins of your time then hopefully it arouses you and you either get off on it (or not) and then you go back to your normal life and probably forget about it until next time you want to be stimulated. But when you are writing a story like that, there’s no ‘break’ from it, because it’s always in the back of your mind. So you are in this weird state of constantly thinking about cuckolding, chastity, humiliation, or whatever else the story involves even if it’s only at a low ‘background’ level.

And then there’s a whole other side to it. Obviously I have been writing my stories for a very long time (well over 25 years I should say) so you’d think this wouldn’t be an issue any more, and I would probably agree with you, but… well, you’d be wrong.

How can I explain this?

So obviously, I’ve been writing this blog for thirteen and a half years, and you know me/us pretty well at this point. However when you write about a topic like Femdom and Chastity, you obviously present it a certain way because that’s what the audience is interested in. I don’t mean I’m making stuff up that didn’t happen, because I never have… but reading the blog I could see that if you met us you might be surprised how ‘normal’ or even ‘vanilla’ we are aside from indulging in ‘orgasm control’ and a very small amount of ‘Femdom’.

And that’s precisely why it’s never become truly ‘comfortable’ for me to write the stories I do knowing that Mistress is going to read them. Yes I feel incredibly lucky to have a wife/Mistress who is accepting / approving of my stories* and indeed she helps me to finalize them before publication by checking my grammar and making suggestions if she thinks dialogue is confused etc (which I appreciate very much as Mistress is an avid reader and is a great help in this regard).

*Incidentally, Mistress also likes to read erotic stories, though they are mostly quite different to the ones I read.

And I still very much do want her to read them, but I still feel somewhat uncomfortable when I write a story and send it to her knowing what’s in it. I mean, it’s a bit weird… and while she knows I wouldn’t ever want to be cuckolded in real life (for example), it’s still not a ‘comfortable’ thing to admit to fantasizing about. And well, like in most of my stories, that’s only the start of it…

In fact, I do think that plays on my mind quite a bit during the writing process and probably means I subconsciously hold back a bit with my stories when it comes to taking them to the next obvious step. I’ve often thought that my shorter stories read like the ‘first chapter’ of a longer story, where I set up themes I want to explore and ‘tease’ them without actually following through on them.

So if you read my stories, you’ll probably notice where I often write about the ‘wife’ character telling the ‘husband’ character what they are ‘going to make them do’ rather than writing about them actually doing it. Sometimes I might have even worked around things I feel uncomfortable writing about directly, by writing about them in ‘hindsight’. I think this is a kind of safety thing, where I’m keeping the story in the realms of ‘fantasy’ even if that’s not how the story is intended. So the story generally ends before these things turn into ‘reality’, which is what I mean when I say that so many stories read like ‘First Chapters’.

Honestly, this is probably a bit annoying for my readers and something I feel like I need to get over if I’m going to continue writing more regularly. I have several stories that could easily be continued, not least ‘Girls Talk’ (the one that I have received the most requests for more chapters for…) but also several others.

I feel like I’m not explaining myself terribly well here. What I mean is, while my stories are basically ‘fantasies’, they do represent the kind of stories I like to read and there’s nothing in my stories that I don’t think is ‘hot’. I mean there’s nothing in my stories that I put in solely for the readers enjoyment. And while I admit that I do write a lot about cuckolding and that’s because it’s very difficult to write multiple stories about chastity without progressing to that, I’m not going to pretend that reading about it doesn’t turn me on.

For me cuckolding is an obvious progression of chastity in fiction because once you make the woman’s pleasure all important, where is the most obvious place for that to go? She cheats with a guy with a bigger cock, etc etc… which leads to having him clean her, and eventually him and so on. All of which I like reading. And honestly if anyone can write 20,000 words about chastity without either going down the Cuckolding or Femdom (or both) route, then that’s pretty impressive.

Sorry, I realise I’m babbling on here…

So after all this playing on my mind for so long, on the Saturday night (the 19th, the day after Literotica published my new story) I went to bed about midnight, but Mistress stayed up much later. I read a couple of stories before I tried to go to sleep, and that on top of everything that had been brewing with ‘Gareth’s Obsession’… meant I didn’t sleep well and I kept waking up. This carried on for quite some time, until about 2:30am or something, when I woke up yet again and very, very hard.

This happens now and again, and oddly usually when Mistress R stays up late reading and drinking wine. As has happened before I toyed with the idea of going downstairs and asking permission to stroke my cock. I never have though, which is frustrating because while I would love Mistress to be more ‘spontaneous’ about things like ‘out of the bedroom’ ass-worship, when it comes down to it apparently I am not ‘spontaneous’ either…

But actually, on this occasion I really didn’t want permission to stroke my cock, because I was so ‘on-edge’ that I knew if I stroked more than about five times I was going to cum. So, after a few minutes of restlessness I got up and went to the toilet and then tried yet again to go back to sleep. But then a few seconds later I heard Mistress shutting off the lights downstairs and coming to bed. Oddly it was only the other day that I was thinking how often Mistress used to stay up late and then come to bed a bit ‘tipsy’ and start grinding her ass against me or even sucking or stroking me until I came.

So when she got into bed I cuddled up against her and put my arm around her. I was still very torn about what I really wanted, and while I wasn’t actually hard any more I still felt incredibly needy and I really, really, really wanted to cum. Not only that but I really wanted Mistress to make me eat my cum. And not just a little bit, but every last drop.

Now the thing is, as long-term readers will know, is that ever since we started 24/7/365 chastity back in April 2011, one of the stipulations Mistress made when accepting the role of ‘cageless’ keyholder was that I wasn’t allowed to ask permission to cum. I believe I asked once about a week in and Mistress’s answer was ‘So you want to end chastity?’… I did not want to ‘end chastity’ then and I did not want to end ‘chastity’ now and so in all this time I don’t believe I have ever asked for permission to cum (unless Mistress had given me one of her special vouchers – more on that later).

In recent years I have told her how ‘badly’ I want to be allowed to cum, but that is not the same as asking permission as far as I am concerned. I think initially Mistress made this rule because she didn’t want me ‘topping from the bottom’ (essentially) and I think it was a good rule. Whether it still is I’m not sure…

Anyway, the point is I haven’t ever asked and so it was a massive thing for me to actually ask her this, so even before I asked I was already feeling quite nervous about it…

Well that’s an understatement, I was extremely nervous about asking her this. Despite this, as I cuddled against her I literally begged her to make me cum and told her how badly I wanted to eat my cum for her. Mistress reached back and loosely stroked my half-hard cock (I tell you these nerves were real and not helping at all!) as she did so I begged her to let me cum again.

Mistress turned over and asked me if I really wanted to be allowed to cum. I said I did and she reached over to turn the light on. Then she pulled the sheet back and started to stroke me, I told her again how much I wanted her to make me swallow my cum, because I wanted her to 100% understand how badly I wanted this. In fact this is something that I’m pretty sure is in our (long neglected) chastity contract, but recently it has been very hit and miss with Mistress either only feeding me a small amount or not doing it at all (which honestly wouldn’t bother me so much if I was coming every week, but of course it’s usually not much more than once a month or so…).

Anyway, as I thought it didn’t take many strokes to push me over the edge, I didn’t even feel like I had got properly hard, which was weird considering my cock was like an iron bar about five minutes before – but like I said, I was extremely stressed about breaking this rule that had been in place for so long and just generally feeling weird about feeling so incredibly ‘desperate’ and craving the taste of cum so badly.

I mean, I’m used to being ‘edged’ and ‘being close’ but this was a totally different level of ‘need’ that only happens very occasionally to me. The feeling is actually very intoxicating and incredibly intense, and if I wasn’t in ‘chastity’ I would 100% have jerked myself off in a heartbeat. But then if I wasn’t in chastity I doubt I would ever experience this feeling…

It was pretty intense and I felt super sensitive really quickly, but even though Mistress pushed her fingers into my mouth, aside from one tiny droplet of cum there just didn’t seem to be any on her hand at all. I couldn’t feel it on my skin either so either it flew off somewhere or maybe I had a ‘dry’ orgasm, which has never happened before I don’t think, but can apparently be caused by stress – which would make a lot of sense here!

So in the end I didn’t quite get what I’d hoped for, but it certainly wasn’t Mistress’s fault, she told me the next day that she was going to feed it to me but it just wasn’t there. I still felt weird about breaking this rule the next day but Mistress told me not to worry about it. I know she was being kind and didn’t want me to feel bad about it and I really appreciated that she allowed me to cum this one time… because I really needed it.

But the more I’ve thought about this since the more I realised that while I was truly desperate to cum in that moment, and while I can’t fault Mistress for allowing me a once in thirteen years request… I think the reason I felt so odd about it the day after was simply that it made me question what up until that point had been a ‘certainty’.

You see, cageless chastity is a whole different thing to the ‘regular’ kind. Not that I’ve ever had the benefit of a cage, but while it certainly has its inconveniences it does offer a certain amount of ‘certainty’, if we ignore the whole ‘being able to pull out’ or ‘still possible to cum in the cage’ arguments. I mean it does a lot of ‘work’, whereas when you are free it’s really down to the person in chastity to be a) mentally strong and b) truthful.

I have wondered from time to time what would happen if one day, like on Saturday night, I was so insanely horny that I just couldn’t stop myself from jerking off. I know that straight after I would feel like shit, but what would worry me more than anything would be confessing to Mistress what I had done.

Now you might think I would be worried because of how I thought she would react and you would be right, but you’re probably wrong about the reasons for it. Obviously I don’t know for certain how she would react, but my worry would be that she would be kind and say it didn’t matter, that I’d done well to last thirteen years and everything that a loving wife would feel was the right thing to say. But… that would be the worst thing I could hear, honestly. I would be much happier if she was annoyed about it, because then I would know it meant something and I hadn’t simply been chastizing ‘myself’ all that time.

Now, this isn’t the same situation as her agreeing to let me cum on Saturday night, because I asked and she decided to let me – it’s not the same because she could have said ‘no’ if she’d wanted to. (She also could have said ‘You know you’re not allowed to ask that’ if she’d wanted to.) But it still fucked with my head quite a bit, and it made me wonder if I would change that rule if it was an option?

I probably would honestly… because these days I am less concerned with being made to wait long periods of time. I am way more excited about the feeling of submissiveness I get from either being allowed to cum, or being ruined and made to eat my load.

I mean, I’d still want Mistress to have a choice, including simply saying ‘no’, and maybe having asked I then wouldn’t be able to ask again for a period of thirty days or something. I don’t know…

I don’t know, it just made me question everything that the last thirteen years had been built on, which is why I felt so weird about the whole thing.

Anyway, about a week after this all happened Mistress teased and edged me, including allowing me to worship her gorgeous asshole. She left me so close to the edge that she ended up ruining my orgasm and feeding me my cum, all of which made me very happy* and then last night…

*I wrote about this in my last post on the 25th of November

30 November 2024

Once again I was very tired and I decided to go to bed earlier than Mistress, who stayed up for quite a while. Again I decided to read a Literotica story before I went to sleep, one I found a couple of days ago but hadn’t had time to read because it’s about 11,500 words! It’s called ‘Black Diamond’ (I’ll post a link at the bottom of the page – I’ve already added it to my ‘Stories by Other Author’s Page‘) and it’s a well written Cuckold/BBC/Slutwife story with an interesting twist.

This took longer than I expected because it’s so long, and I eventually clicked off my light at just after midnight. I didn’t get hard while I was reading the story, but I enjoyed it. However, about half an hour later I woke up again and my cock was rock hard. I must have laid there for ten minutes sleepily debating whether to get up and go downstairs to ask for permission to stroke my aching cock, but once again I elected not to. One of these days…

I eventually went back to sleep, and then sometime later I woke up again, suddenly wide awake – I’m not sure what time it was, maybe 1:30 or 2am. I heard Mistress coming to bed and I reached across to stroke her back as she got onto the mattress. Unlike last time Mistress moved straight towards me and cuddled me, and as I felt her gorgeous naked body pressing against me I felt myself getting very hard.

Mistress reached down and started stroking me, this time nice and rough, making sure I stayed hard. It felt amazing and for some reason even though I only came about a fortnight ago and was ruined a week ago I was convinced she was going to let me cum again. Mistress continued stroking me and rubbing my balls, bringing me closer and closer and closer to the edge. So close I could almost taste it…

But as soon as I told her I was getting to the point of no return she let go! I couldn’t believe it. I mean, I don’t really know why I was so convinced she was going to let me cum, and in a way I kinda loved that she didn’t, but at the same time even though it hadn’t been that long I was already feeling pretty desperate to taste my cum again.

We cuddled a while longer and then Mistress turned over and went to sleep. I also went to sleep (eventually!) and it wasn’t until I woke up the next morning that I remembered the voucher that Mistress gave me in October which granted me permission to ask for an orgasm at some point during December. All this happened way after midnight on November the 30th so technically it was already December and I could have asked. Daaaaaaaaaaaaaaaaaaaaaaaamn!

Of course, it’s only permission to ask, it doesn’t guarantee anything and Mistress could have said yes, no or ruined me… but if I had it in my mind I would 100% have asked. Believe me. I really wanted to cum again.

Incidentally, after I asked Mistress to let me cum the other week I did suggest that we treat it as me ‘using my voucher’ earlier, but Mistress decided to let me keep it, which was very nice of her.