My path to chastity

So I thought I'd put a little update here with a touch of irony and a little warning to my future self; never tell someone whom you'd like to get locked up by to be mean to their chastity subs. In a years time you might be where they were then (and its almost a year to the day):


LadyFedora Choices choices... shall I unlock him tonight... or just keep him locked... difficult choice (or maybe not!)
Oct 15, 2014 Report

1. 
   Kontraband Keep the lock shut! It's an easy choice... maybe I shouldn't say such things just in case I ever get locked again.
   Oct 15, 2014
2. 
   Kontraband
   
   Looking back at my past comments to you and thinking they lacked a certain amount of foresight!
   Today at 12:24 PM​
3. 
   LadyFedora
   
   You have no idea how thankful I am that you found this Kontraband
   Today at 6:05 PM​
4. 
   Kontraband
   
   Oh I have a very good idea! Curse my arrogance when unlocked.​

 

Ah well you know me and putting my foot in it @LadyFedora ! Truth be told when I posted that I did think I might one day get locked up by you and the post would come back to bite me.

 

After first agreeing to be locked by @LadyFedora she set me a nightly task to complete; I am to get naked, lie in bed with nothing covering me and for 5 minutes with one hand I stroke my cage (not touching my penis through the bars) and the other hand lightly squeezes my balls. To complete after I finished I was to say “Thank you Lady Fedora”. I thought I had an idea as to the reason for this task; to set aside 5 minutes a day to think about Lady Fedora and her control over me. To an extent I was right however, I underestimated the power of this simple task. Strange that I should do that given my experience of erotic hypnosis; I recognise how powerful ritualistic actions can be (such as listening to a hypnotic file).

In the first few nights of completing this task I experienced two things; pain and frustration. My balls hurt from the squeezing. The stroking should have felt good but didn’t because of the cage which was frustrating, so I stroked faster which was even more frustrating. You can see how this escalated! I would grimace the whole time. At the end I said “Thank you Lady Fedora” almost as an after thought on those first few of nights. At this time it was a nightly ordeal to be gotten through to please my Keyholder.

After a while my feelings started to change. It was still painful however, less frustrating as I knew it was pleasing to my Keyholder that I was doing it every night. I started to enjoy the fact that I was doing this for her. I no longer grimaced. At the end I would gladly offer my “Thank you Lady Fedora”. The ordeal had become ritual praise.

At some point towards the end of the second week my feelings changed again. Now I seemed to be embracing my masochistic side. No longer was the experience painful but pleasurable. I found that I enjoyed hurting my balls for Lady Fedora. In fact I wanted to hurt them and began squeezing harder and instead of pain experienced pleasure. I find now that my squeezing pulses with the stroking of my cage and I pulse with pleasure as I do it. I have a big beaming smile the whole time. Now at the end I say almost in rapturous voice “Thank you Lady Fedora”. The ritual has become true worship.

Last night things changed again, I couldn’t help but thrust my hips in time with the stroking of my cage. A final confession; I used to look desperately at my timer to see how long I had left. Now I barely check in fact last time I only checked once with 30 seconds to go. Who knows maybe tonight I’ll finally finish the task without ever looking at the timer!

Thank you Lady Fedora

 

@Kitty_Mischief great meeting you today but I can see you being a real pain in my arse some time soon

 

I think I'm ok as I am @LadyFedora unless such a pain would please you. (See @Kitty_Mischief I can't help but get myself and specifically my arse in trouble :spank

 

Well this week there's a new challenge from @LadyFedora that was inspired by @McSlavey and his wife's card game. Some of you will already be aware of this but I have to ask dominant types (including switches) to 'sign' a card saying they recognise Lady Fedora has got me locked up and then let her know how long they think I should stay locked up. I perhaps get off lightly here as the other sub is doing this in person at a play event with Lady Fedora whilst I'm doing it online of the course of this week.

After my initial enthusiasm to get cards signed wore off I've started to find this rather embarrassing especially when asking friends on fetlife who I will see in person next week. Until now they may have been aware of my chastity if they'd looked at my recent writing or my profile updates on fet but I hadn't directly talked about it with any of them. So the next munch may prove very interesting and I suppose I'm likely to get a few questions/some teasing from them.

It's been very interesting seeing the range of time that people are putting on the cards. This currently ranges from 0 days to 3 months. All seems to depend on how familiar people are with chastity play and how sadistic they are. So far I have seven cards and I hope to have a few more by the end of the week (yes the looser gets punished, with extra days equal to how many cards they lost by) seeing as I have no idea how the other sub will do I have to get as many as I am and hope it's enough. He will know how many I have when does it in person so I can only hope that if he gets in the lead he is nice and doesn't win by too much.

 

So today's update is essentially about sexting. However, first a little back story:

Recently in discussion with @LadyFedora I mentioned that I actually wasn't all that frustrated and horny from my chastity to her. I identified two reasons; one a sort of sub bliss from being hers that overwhelmed any sense of frustration and two the lack of discussion of orgasms in our conversations (both hers and mine, but particularly hers). This lead to her asking me to write a piece for her that many would construe as topping from the bottom about my feelings on frustration and what really gets me fired up during chastity play. Allowing Lady Fedora to better understand my mind and giving her more tools to toy with/control me.

So that brings us to today, I had written an erotica for my Lady that she very much enjoyed in which she got three orgasms. I was given the opportunity today to help Lady Fedora actually have some orgasms while we chatted, in essence sexting. She asked how many I thought she should get and given there were three in my story I went with three (and she made me pay a price for each one by the way, yes I had to buy giving her orgasms). So she went and got all the toys she wanted available and we got started (and for those following the points on anal training I was made to wear a plug for most of the experience.) Lady Fedora told me which toy was to be used and then asked me to walk her through how I'd use it (she followed my lead).

Before too long Lady Fedora was at her first orgasm, I on the other hand was still locked and plugged and leaking and breathing heavily in desperation as if I had actually been there. After a little talk about how desperate I was Lady Fedora started to play with herself again and painted an image of what I'd be doing now if I was there. We began again with the reminder that she was the one about to get two orgasms and me none. Well I started telling her what I was doing and once again I was getting desperate, by the time she got to her second orgasm I was overwhelmed; I really would have done anything to be let out my cage, to be able to touch down there to orgasm. However, we weren't done, I'd bought 3 orgasms for here (and right now I was cursing myself for buying so many) and only two delivered so far. Well there wasn't much break in between two and three except for Lady Fedora asking just what I'd do for that orgasm (would I give up all the points I had and agree to minimum 3 month lockups just to orgasm now and believe me I said yes in that moment). So I started with the instructions again and very soon Lady Fedora was at her third orgasm but then she couldn't help herself, things were just too good and she kept going to grab a fourth orgasm!

So that was the end; 4 orgasms for her and still at least 28 days to go for me! I was left an utter desperate horny mess who in that moment would have done anything for her to be able to cum. I have to say that around orgasm number three for my Lady was probably the most desperate I have ever been to get out of chastity. I was rewarded with a picture of the damage done to Lady Fedora's sheets and it was impressive. We'll certainly be doing that again, I just don't know if I won't pass out from desperation next time.

 

Yesterday something dreadful happened. It should have been a special day; I had reached my locked record under @LadyFedora and she had permitted me to unlock to go rowing and then when I returned I was to be allowed play time thinking about being allowed to penetrate my Lady's arse. When I returned from rowing I was to create a cock and ball bondage and so I tied a rope around the base of my cock and balls and then ran the rope up between my balls as a separator and tied it off. Now I was to get hard and then edge 6 times and time how long each edge took.

I began my stroking and quickly felt amazing being allowed to stroke with such great thoughts. I reached the edge quickly in 45 seconds (it had been a while) and ceased my stroking. A couple of seconds later I could feel that something was dreadfully wrong, that I had gone too close to the edge. I desperately started thinking about anything to stop what was coming but the damage was done an orgasm was coming. Instinctively my stroking hand reached to touch my cock again as the orgasm began however I resisted the urge and pulled it back allowing the orgasm to ruin its self properly. After this shameful failure of my Lady's instructions I completed the remainder of the task and then relocked. There was little pleasure to my remaining edges knowing the failure I had just committed and I was pleased to get back into my cage where no more harm could be done.

The times I recorded for the edges have now been used to work out how long my chastity will be extended as penance for my failure and I will not be permitted to stroke again this lockup.

It is with great sadness I have to admit this is the second time I have failed my Lady in this way.

 

It has now been pointed out that I also failed to follow the instructions correctly by using lube for this stroking when I should not have. Needless to say I have a lot to learn and my carelessness has caused a great deal of trouble.

 

Yes @MistressLianne , there have already been a great many apologies and there will be many more for such misbehaviour.

 

Glad you like my thread Aiki, its been quite a journey so far and much more road left to travel. Have fun with Pixie tonight

 

You're not the only one; can't describe how disappointed I am with myself over what happened.

 

Today has been a day full of edges. Back to that in a bit but first a little update on my journey.

Since failing @LadyFedora the weekend before last things ave gotten better. We now have a clear punishment set if I should make the same failure again and its very discouraging of further accidents. I've had several opportunities to atone for my mistake and to prove that I am worthwhile keeping as a sub since then. I've had a bit of time with my girlfriend to play with a new toy; a violet wand. She's increasingly getting more interested in sensation play and meeting people in the scene. She was never a vanilla but she did have tight limits which are starting to open up quite a lot.

Today Lady Fedora decided to demonstrate her power over me quite a bit. I received a message early on today that I was to edge 8 times in four pairs at least two hours apart from each other. All of the edges that follow were done by applying a wand to my cage. So I set about my task completing sets at 09:15, 12:33 and 15:19. Then I ran into Lady Fedora at the Mansion and her fun really began. We talked about how the edges affected me and how the third set I did was particularly frustrating and had me moaning. Lady Fedora noted that two edges at a time really wasn't that many. It was 17:30 so the perfect time to complete a new set of edges, not one of the planned ones though. Instead Lady Fedora made me ask @MistressLianne how many edges I should perform and she chose 4 extra edges. Now I was starting to get worked up by the end of these and feel real frustration. However, Lady Fedora was not done. She decided a demonstration of her power was in order and that she would do this by choosing random people in chat I would have to ask for more edges. First there was @frisianm who added 5 which I completed and then @kickball who added another 3 edges. The point was to prove she could make me do these things and it made my feelings of submission deepen each time. To be clear; I'm a shy person asking people to randomly give me edges is embarrassing for me and not easy.

Then Lady Fedora really pushed me, she knows I am straight and she asked me to e-mail a male Dom friend of hers to ask for another set of edges. This was really stretching her control, there are certain people I won't sub to and male Doms are one of them for a fairly obvious reason. However, given my submissive feelings at the time and that this was a friend of hers and not a random male Dom I complied and he added another 3 edges. The only reason this was possible was that I was doing it as an act of submission to Lady Fedora but it still pressed my close to my limits (but did not exceed them to be clear). So if you haven't been counting since Lady Fedora and I started chatting in the evening I've now completed 15 edges in 1h45mins. At this point each edge induced a tensing in more mucsles extending into my core abdominals, each one became more intense than the last and that would only grow because, now it was Lady Fedora's turn herself.

First off for her fun she ordered me to insert my butt plug which thankfully I managed in the time limit she gave me. The she laid out her plan, she would vibrate herself and I would try to edge. In the meantime she would narrate a scene involving the two of us until I edged, then I would take over the narration and rest until she orgasmed and I went back to edging and so on. The story began and I felt the scene Lady Fedora described; of her digging her nails into me of the nipple-clamps she placed until I edged and took over talking about how she would toy with me pulling on the clamps where she might rake her nails. She has told me before that I'm very good at portraying her in erotica I've written for her despite never having sessioned together. Eventually she orgasmed and took over again, the story me was bound to a mattress and toyed with some more, I'll leave out any further details as they are rather private (unless Lady Fedora instructs me to add them at a later time). I was taken to the edge second time and we swapped places. When we swapped again I was to edge three times before we swapped and the final time I had two edges before she concluded the story. This was an extremely fun session building our shared fantasy together.

During this time I came to a realisation of sorts. Setting aside the fact that one day, not too soon, Lady Fedora may actually grant me a full orgasm I realised that edges are my new orgasms. Yes I don't get to go over the edge and they are frustrating but they are what I get, as Lady fedora was orgasming in our story I was edging it was my equivalent I suppose. My full orgasms are so rare that edges are taking their place and there's one big advantage of edges to male orgasms; you can have lots of them in a row just like female orgasms (I never persevered long enough to train myself to multiple orgasm though I understand the technique and got close some times, and really it wouldn't be much use to me now if I could anyway).

From a novice sub 39 days ago I've come a long way and it means a great deal to me to be told how proud of my progress Lady Fedora is. I found this journey difficult when I failed her the second time and I wondered if I was worthy of her time. I'm glad we both pushed through that and I have regained the joys of being a submissive that Lady fedora is proud to have. (Before Lady Fedora my longest time in chastity was 28 days so I'm long past that now).

Oh and in case it slipped anyone's mind from the beginning of the story I still have a pair of edges to complete with my nightly ritual. That will bring today's edge total to 30! Far more than I've ever done in a day before, a whole new world of sensations was opened to me and I love being Lady Fedora's submissive. Thank you Lady Fedora for taking me on.