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17. Training

Alternative lifestyle and kink continues to throw mental curveballs my way. I continue to feel like I’m on a roller coaster ride of highs and lows, most of the latter could be of my own doing. I probably am my own worst enemy sometimes.

I have been chastity for many years now. Whilst I have never liked the fact that my sexual stamina has all but vanished, it’s never been a real issue until recently. I’m still able to please R one way or another and she’s very happy and satisfied, both in a sexual and non-sexual sense. Perhaps more so than ever before. 

The Thoughts

Recently thoughts of sexual inadequacy have been plaguing my mind. I want to be able to give R the best sexual experiences, sometimes without the use of ‘assistance’ (usually in the form of sex toys). I’m simply not able to fulfil that in the way I’d like to currently. That’s an important point of note – ‘ways in which I’d like to’. When I have spoken to R about my stamina issues, she has reassured me that I’m providing everything she needs, inside and outside of the bedroom. I believe she’s being honest, but it doesn’t feel that way to me though.

I get a fair amount of sex with R. Likely more than the average chaste sub. Increasingly though, it’s over very quickly, at least for any activity involving my cock! Valentine’s Day is a good example of this; see My Valentine’s 2023 Blog Entry if you haven’t already. 

There’s making love and there’s fucking. I’m not sure recent efforts fall into either category. I would really love to be able to fuck R in a raw, passionate, lustful, animalistic way. I know she loves a hard fuck from time to time, but it just isn’t possible with me. My desire for her is so strong, but I simply cannot perform in this way any more. That type of sex is a sure-fire way for me to finish early. Gentle love making with R is amazing and I last longer like this, depending on how long I have been locked and denied for. But that’s not what is always needed or desired, by myself or R.

The Trigger

I have thought about this for some time. I don’t know what triggered these thoughts to begin occurring. They are a fairly recent addition and I can’t explain why. I have been chaste for many years and my sexual stamina during this time has been very similar to how it is now. Low. Nothing has changed for this to suddenly become an issue or cause of concern to me. I have never had an issue with overcoming this with strapons and toys but recently I have felt that I should be able to provide that pleasure without that assistance.

Image by Arek Socha from Pixabay


I approached this issue in the same way as I have tackled other issues. I researched online. I don’t have ‘kink friends’ or even friends that are ‘kink friendly’ and are therefore aware of my kinks and dynamic, so my options are limited in that sense. Perhaps that is something I should look to change somehow. Very quickly I ended up finding two potential solutions:

  • Drugs/medication/numbing creams etc
  • Stamina training

I really don’t like the medical route. There are varying degrees of potential success evident from my research and some treatments come with undesirable side effects. Some are simply passion killers that need to be planned way in advance of sexual activity. I didn’t fully rule this route out but it seemed to be an extreme last measure. 

Image by PublicDomainPictures from Pixabay

Stamina training made sense. The more contact my cock gets, the less sensitive it will become. The basic premise was logical, as long as control is retained and I don’t cum! How training would fare in combating the ever increasing libido and sensitivity that chastity, tease and denial and FLR provide, I had no idea. As I read more, I discovered that ‘edging’ could be a solution and there are various aids to help. There is a specific Fleshlight training aid. I wasn’t expecting that. I then remembered that I had a Fleshlight, just a basic one, in our sex toy stash. Maybe that could help. I do remember it being really ‘effective’ back when I was able to use it whenever I desired.

Another Of Those Conversations

When I’d exhausted the research it was time to move forward and talk to R. Well the conversation wasn’t that hard but it was a conversation with R that I’d really rather not broach. ‘Hi honey, by the way, I have issues with my own sexual stamina and I need your help…’ Not something I ever expected to be confessing but I explained my feelings of inadequacy and low self esteem regarding my sexual performance to R. I explained that I had done some research and what the two solutions I had arrived at were. R quickly said she didn’t like the medical route which was something of a relief. Comically, having discussed with R, my Facebook feed later began to be littered with ads to treat such performance issues. Thanks for the reminder Facebook… I’m still getting them even now.

This left option two; stamina training. I was slightly fearful as I knew I was asking to be out of my cage on a frequent basis. Something that obviously flies in the face of chastity, FLR and most D/S dynamics involving a cock cage. I think R saw a degree of the mental angst I was in and again reassured me it was not necessary; my performance is just fine. She agreed to help train me. I was really happy that she responded so positively and excited to start.

Life Gets In The Way

For the next three evenings, I was out of the cage either with R edging me using her hands or using my Fleshlight. It was something I quickly began to look forward to and, whilst I know R was taking it VERY easy on me, I was able to retain control for longer than I expected and stop before cumming. It’s hard to say if it was working or not over the space of only three days but I was hopeful.

After these three nights, life got in the way. Nothing huge or life altering, just general day to day life. Busyness, tiredness, children etc. For one reason or another, training just didn’t fit. I understood this but I did find myself being disappointed and an element of expectation was creeping back into my mindset. It wasn’t at the stage of resentment but I was aware of its presence. After a week or so, R resumed the training. I’m not sure if I’d had a ruined orgasm in that period, probably not as when we did get to train, it was as if I was back to the start again. We had to pause much more frequently and it was nothing like the first three days. I felt as if the training was failing. My excitement and anticipation for training sessions stopped and turned into apprehension. 

The last training session I had, I wasn’t doing particularly well, focussing hard on my breathing. Out of the blue R said ‘Do you want to practise for real?’ Of course I did! Wow, being inside R was beyond amazing. I knew I wasn’t supposed to cum but this only made me cum quicker. I pulled out, knowing I had gone past the point of no return and ruined before apologising to R. She then told me I had better ‘clean up’, which I duly did.

Training has since stopped as I spoke to R again and explained that I don’t think it can win the fight against a super sensitive chaste penis. I did revisit the medical route again in my research but I’m still not willing to go down that path.

So where does that leave me?

The last time we had sex, R wanted just me – no toys or strapons. This was obviously to show me, to demonstrate to me that I could still please her without the use of ‘assistance’. Honestly, when she said ‘Just you this time’, my overriding emotions were anxiety and fear. I suggested the use of a strapon, even if it was just to ‘finish the job’ (I described it a bit more eloquently to R at the time) but her response was ‘Not this time’. Of course I didn’t last long, even taking things slowly. I lasted longer than I expected, long enough for R to get tantalisingly close to cumming. I think she must have been trying hard to cum quickly in order to help me. Seeing her so close, I felt obliged to assist and with her blessing I reached for a toy. In all honesty, it was a relief. The pressure was off. R didn’t complain and she did cum. As we lay back together, satisfied and sated, I wasn’t happy and R could sense it. She gave me a familiar ‘chin up’ look, held my hand and said she just wants me to be happy.

I was ecstatic that we had just had sex; I got to cum, it was a full orgasm which I very much enjoyed. My face obviously wasn’t conveying this. It was my own performance that was making me unhappy and realising that I was physically incapable of performing how I want to, and how R wants and needs (at least every now and again). My penetrative sex disappoints me. This was the statement I had buzzing around my head. I can list many ways I can pleasure R, but my dick is way down in that list currently. 


R recently told me recently in a moment of omission that she has never really got off on penetrative sex with me. Whilst hearing that hurt, I do understand and I’m glad she felt able to tell me. I have written about how sex between us used to be in the past. Even then, when I remember having far more stamina, I now know it wasn’t R’s favourite or most pleasurable element of sex. I’m not sure that’s the case with some of our larger toys but that’s probably best saved for another blog entry! My point being; should I be so hung up on my performance since being chaste? Well, for someone so focussed on sex and sexuality, it’s hard not to be. Looking back at the times pre-cage, I’m not sure I ever had real stamina, I did however masturbate like it was going out of fashion which in turn led to longer (not necessarily better) sexual performance. I wouldn’t want to go back to that.

Unfortunately I think I do have some degree of performance anxiety. This doesn’t help with premature ejaculation and this becomes a bit of a vicious circle. One leads to the other and so forth. I’ll never, ever, ever not want sex with R but I am beginning to understand why and how some chaste males are ‘pussy free’. It does feel a bit like I have fallen out with my penis, who, until this point, has always been an ally. It’s not as bad as it sounds, and I can and do keep on smiling.

Moving Forward

I haven’t come full circle in my thinking yet. It does feel like I have traded my sexual performance for the betterment of our marriage and dynamic. I’m sure the benefits of this trade outweigh the issues I have described above. I had thought that I had experienced all the curveballs chastity had to throw my way – obviously not. I have considered asking R if we can just remove the cage but I don’t see how that would help. 

Having done more research via the online chastity community, it’s really common to lose stamina, if not guaranteed. But some if not most subs see this as a privilege or badge of honour showing their devotion to their keyholder. I understand this but I’m not sure I’m ready to accept it fully yet. I want to have my cake and eat it but it’s just not possible – after a few days without the cage, even when I make conscious effort, my devotion drops, sexual expectation and the barter system sets in and our dynamic and relationship suffers. 

There is a part of me that thinks ‘Just let go. Of everything. R knows what’s best. Trust her to lead you, your submission, our dynamic, our sex, her sex with others, everything’. I don’t know if R would even want that to happen and there is a part of me that fears it would accelerate our dynamic beyond what I could deal with. It does feel as though I’m falling deeper into submission to a level which I had never anticipated. I do like this feeling but I would describe it as dizzying. 

Photo by Brett Jordan on Unsplash

If R wants the raw, animalistic, lust driven sex I cannot give, her options are the strapon with me or to seek it elsewhere. It hurts for that to be the reality. The latter isn’t  ‘off the cards’ but opportunities are few and far between at the moment we aren’t making conscious efforts such as looking online. This is mainly due to mental health issues I have tried to explain in previous blog entries, coupled with general obstacles that normal life presents. R has always said that ‘real is always best’. What she meant by saying that is that my cock beats all the strapons and toys but that statement does linger in my mind and make me think that maybe she just doesn’t know what she’s missing. R is going ‘out’ with some friends at the end of the month. I’m simultaneously excited and fearful to think what may come.

In Summary

When I figure this one out I’ll let you know! I need to find my own ‘off switch’ and stop thinking about this so much. I also know right now R is the happiest in our relationship and dynamic than I have seen her in a long time – which I really like. I don’t want to be the proverbial fly in that ointment.

I’m not sure why I jump from one issue to the next. I never used to. Perhaps it is linked to fear of R with other men. It’s the only difference in all my years of being chaste. I guess I’d need a therapist to get to the bottom of that.

Coming Next…

I Have No Idea – Watch This Space!

Feature Image Photo by Dainis Graveris on Unsplash

One response to “17. Training”

  1. […] was reading a fresh post on a relatively new chastity blog I’ve been following (I mean, only one that I can think of […]

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