Day 23 & 24 main post with all info
previous CP: 931 Day 23:
12 (from baseline)
50 (anal task, +10 oral, +25 size, +5 depth, +10 leak) Day 24:
12 (from baseline)
20 (wholesome task)
=== +94
current CP: 1025
I pledge to wear a buttplug for at least an hour a day till the end of locktoberfest. (+60pts)
First, I had to do a punishment for my transgression towards Mistress Blake. I'll not go into details, but after finishing, I had sore nipples and a sore throat. I deserved that for my weakness and disobedience. Thank you, Mistress!
Then I started doing the task. Obviously I joined and helped Mistress, but I didn't get any hints yesterday about the theme, so after the first few pages, I knew that a long night would be ahead of me. And it was! I was waiting too long for this task not to enjoy it to the fullest .
Today I used my curved glass wand (great for prostate play) and two silicone (with balls) dildos; the smaller is 6in insertable (1,3in diameter), and you've seen the bigger one in the shopping picture task (~8in insertable, 2in diameter, 9,5in total). I consider the bigger one huge, and my goal of the session was to fit inside me . I've also had some buttplugs of different sizes for stretching and prep (with a T-shape base so I can wear them for extended time!) and anal beads just for fun.
First, I did some warm-up with my plugs and watched some ladies play with toys too. Then I wanted to play a tease or a dildo hero, but both turned out to be going too fast. I wanted to explore at my own pace, and it's also a lot easier to try different positions if you don't have to look at a screen .
The session took about 2.5 hours; I was completely exhausted after and went straight to sleep after cleaning up. First, I did the stretching. Then I did some faster riding on my 6in dildo (while reading some erotica), and then I managed to fit in the largest dildo about 3/4th of the way in . I felt completely full at this point, so I didn't want to push more.
At the end, I did try to milk my prostate with the glass wand and tried different techniques, positions, hypnos to watch, but the most I managed was some leaking (not enough to satisify my huner when licking it up ). Maybe my prostate took too much pounding to respond, or maybe it's the fault of orgasms I had past week . I definitely need more practice for this love-button to work as intended.
Overall, it was a great session . I took the pledge, and I love that sissygasms are allowed from now on . I'll sure as heck try to finally achieve it this month.
It was pretty nice to include some relaxing after the punishment and fucking I did yesterday. I don't know if I would want another intense session today. (I have an idea what ginger may be used for, and I was scared of it being today. )
I did some gaming for the task. Recently, I am replaying a game in a foreign language I am learning. You get the best of both worlds that way: learn the language by immersion (especially if the game has dubbing and subtitles) and have fun by playing.
This selection also pulled all my attention, so thanks to that, I didn't get any nasty thoughts; otherwise, I would probably be thinking about some censored porn I was watching today. Well, I did do a second hour of gaming with my buttplug in for the pledge part, but that's outside of the task .
Also, I didn't like Paige's comment about the boring writing task tomorrow. I very much enjoyed that part! Well, probably too much, given how many paragraphs I write . No other tease made me reflect so much on myself .
24th locktober update
Name: Medoria
Genderidentity: Male
Cage: Tiny Metal Cage
Mode: 24/7
Pledge: 1) to wear the key to my cockcage on a necklace or bracelet during the whole of locktober (potential 50 CP)
2) become a hypnoslave for a week (potential 40 CP) (completed)
3) get-in-shape three times a week for a month (potential 60 CP)
4) go to the spa appointment caged (potential 20 CP) (completed)
5) showing my purchase on the forum (potential 30 CP) (completed)
6) personal pledge, chastity hint to 20 people min in a month (potential 100) (completed)
7) yes ma'am for a week (potential 50 CP) 08.10 (completed)
8) body writing for a day (potential 20 CP) (completed)
9) deepthroat training for a week (potential 50 CP) 13.10 (completed)
10) censoredege for a week 15 mins (potential 60) 20.10
First Weekly Pledge: no porn for a week unless permitted ( potential 20 CP) (completed)
Third weekly Pledge: daily porn for an hour (potential 60 CP) (completed)
Fourth Weekly Pledge: lick it up precum (potential 50 CP)
Basline CP: 20
(5 from 23.09 and 5 from 25.09 and 7 From the event, 10 from 28.09, 132 (/5) edges and 5 (*2) ruins from 29.09, 10 from the second event, 20 from 01.10, 5 from posting on 01.10 in the forum, 20 from 02.10, 20 from 03.10 and 10 compensation, 15 from 04.10, 35 from 05.10, 30 from 06.10, 20 from 07.10, 25 from 08.10, 20 from 09.10, 20 from 10.10, 15 from 11.10, 10 CP from sole hits and 10 from butt hits and 10 from nipple clamps and 10 for ballbusting from 12.10, 25 from 13.10, 30 from 14.10, 30 from 15.10, 25 from 16.10, 30 from 17.10, 20 from 18.10, 10 from 19.10, 25 from 20.10, 35 from 21.10, 40 from 22.10, 20 from 23.10, 20 from 24.10) + (Baseline CP 20x23) + (Pledges 4 (20), 5 (30), 2 (40), 8 (20), 6 (100), 7 (50), 9 (50)) + (weekly pledge 1 (20), 3 (60))
today was so simple and easy, like a break, I hadn't played dark souls on a while so I went and started ds3 for the first time and finished the tutorial area and the first map after and their bosses, it was fun, not sure why I stopped
Ofc nothing sexual happened except for me raping the fucking hollows over and over lol
This week has been fun following each of the tasks and of course I also went to a smaller cage. I liked the blindfold task and of course the vibrator but am also starting to wonder about the points what they will be used for and if I have enough, will e tra days be added if there are too few that kind of thing
Locktober has gone really quickly but has definitely been fun and have enjoyed doing each mornings task but am so horny I am so looking forward to being allowed to play.
OMG I just got logged out after translating all the stuff I wrote to my 'little pink private book' when trying to post it.
I guess I've to go for it a second time, I hope you don't mind if I spare some parts (especcially the crying about my constant horniness and the 'need' to relieve some pressure ) and will accept a punishment for sparing if the community wishes to.
The past 7-10 days have been really challenging - especcially because of my Job and therefore my lack of private-time. In the past days I've more then once thought about quitting locktober an at least relieve some sexual pressure. Nevertheless I've been a good boy, kept being chaste 24/7 and have done all the things I so eagerly pledged in the past weeks.
The Things that kept me from quitting are the thought about the disappointment of Mistress Skye and the community in this forum, constantly posting about there struggle and therefore giving me the feeling of not being alone with it. The competetive part of being in the top 5 due to the cagepoints does the rest.
[Spared part about horniness, urges, pledge-completion]
Two things for closure: I love the person this locktoberfest turns me into but I'm also afraid of what's more to come. And last but not least: Only less then 7 days to go for to complete the locktober(fest) - you can do it too!
Monthly:
1. I hereby pledge to wear my key on a Necklace during the whole of locktober. If I manage to keep it there I'll earn 50 CP at the end of locktober. If I fail to do so I'll loose 25 CP.
2. I pledge to do 20 Minutes of excersise three times a week for the remainder of locktober (W1: 3/3; W2: 3/3; W3: 3/3; W4: 1/3)(60/-30).
3. (Event): I pledge Go eat any cum and precum which exits my locked up clit during locktober. This includes ruined orgasms and nightly leaking (polluarche, subconscious ejaculations). Includes sucking on panties if there's anything in them. (60/-30)
Week 1:
1. I'll abstain from porn for seven days in a row. (+20 CP earned)
2. I pledge to watch a video (10 min) or listen to an audio (20 min) for the next seven days every day. (+40 CP earned)
3. I promise now that I'll keep my spa appointment (partial massage 06.10.) and go to it with my cockcage on (20 CP earned)
4. I pledge to post a picture of me wearing my shopping items when arriving (30 CP earned)
Week 2:
1. Whenever a woman asks something from me, I'm only allowed to answer "Yes" (50 cp earned)
2. I pledge to wear my body-writings for full 24 Hours. (+20 CP earned)
3. I'll practice sucking and deepthroating my dildo for 7 days 10 minutes a day. (+50 CP earned)
Week 3:
1. I will watch minimum 60 Minutes of porn every day for seven days in one setting. (+60 CP earned)
2. I pledge to edge to censored porn for 15 Minutes everyday for a week (6/7). (60/ -30)
Week 4:
1. I pledge to lick up and savour all (pre-)cum I'm release from now for the next 7 days (50/-25)
2. I pledge to wear a buttplug for at least an hour a day till the end of locktoberfest (60/-30)
Thanks everyone allowing me to continue. I agree with SlenderSissyNewbie's assessment that I shouldn't be allow to unlock and edge anymore (I did already once more before reading her post, thus given myself negative points for day 22). Of course took all the other pledges available. I usually don't leak a lot of precum, but I will lick up anything I can. Still got two days to catch up to, hopefully can do them later today.
Pledges: pornfree (20cp done)
keep-writings-24h (20cp done)
hypnoslave (40cp done)
butt-salve (60cp till done)
Yes, Ma'am (50cp till done)
practice-sucking (50cp till done)
show-items-once-arrived (30cp till done)
Porn Buddies (90cp till done)
lick it up (50cp till 10/31)
get-in-shape (60cp till 10/31)
buttplug (60cp till 10/31) censoredger (-30cp failed)
Week Four Reflections – Self-awareness, discipline, and expectations/attachments
Prelude:
As I sit here caged reflecting both on the last week and the whole of this incredible journey so far that I have now come to see as the reason for taking part in Locktoberfest and what it has meant for me along with all that I have written and contributed along the way to this small but wonderful community/ and as I have become to see it personally - support group, the dominant, strongest feeling I feel among so many contradictory feelings, and yes, there are many, is one of pure gratitude.
As the sub-title of my week four reflections allude to, this personal gratitude I wish to express is born from a deeper self-awareness, discipline, and a ‘light switch’ moment in me realising that if my expectations/attachments are not aligned with my values, then what I need to do is to learn to gently acknowledge this and not become angry, frustrated, or anxious because of these expectations/ attachments I have, or I think I should have, but just let them go and be compassionate to myself.
And this is the thing dear reader, these are simply my own personal feelings and reflections and if in reading this you do not, on your own reflections of the last twenty-five days, see and feel similar things that I describe through taking part in this challenge that is OK; our personal journeys are simply that – personal. This final reflection celebrates my journey in being an obedient sub and in wanting to please Mistress Skye. It is for this reason I am posting this openly both here and publicly.
Self-Awareness
During the forty odd years that I have explored and experienced many great and not so great aspects of the kink-world both within relationships, as an individual, and being among like-minded people there comes a point in time, and Locktoberfest is no different, where I get to a point in my thoughts and reflections of, “Now that this has happened, how and in what way will I respond? What next?”
This time with Locktoberfest and the fact that this exquisite tease as its name infers is, and can only be for a month meant that when I arrived at this point this week and asked and reflected on these questions above, my answer was a very positive surprise to me. That answer was and is, “Continue being in chastity and trust that I will find a way to be successful in incorporating long-term chastity into my life and ultimately the already Female Led Relationship – though currently non-kink - that my marriage of the last thirty years has become.”
What this tease has taught me is that, if, I want to start to begin to re-introduce kink within my marriage that is more in service of what I am now more self-aware about – that I am an out and out submissive - is that the type of role that is truly authentic to me - being the sub in a power exchange with a strong beautiful and powerful dominating woman – then it can only be achieved through consensual cooperation in taking steps of establishing and acknowledging that a high degree of awareness and communication between ourselves is necessary to ensure that the result of whatever is discussed regarding this wished for re-introduction of a kink based power exchange will be desirable for both of us.
Those initial consensual steps I now fully recognise are unquestioning obedience and trust, and that the first step in establishing this desired trust and mutual kink-based obedient consent with my wife is to acknowledge and communicate this awareness to her and hope and trust that my offer and surrender of my ability to orgasm to her control – chastity - physically and mentally will be desirable for her.
What this tease has also made me more self-aware of is that in surrendering my control and ultimately and hopefully submitting to a sub/Domme power exchange in my marriage that I yearn for I must trust that I will be able to handle whatever happens either way – learn to surf the waves of intense feelings and emotions that comes from surrendering control and being open and vulnerable.
I can now see that I can trust my wife to tell her how it is I feel, and she will not use it against me.
While I am no expert yet at this, I am learning to stop fighting with myself, to stop fighting the universe and the natural flow of things, and more importantly stop resisting and pushing against reality.
For this I can not express enough the gratitude that being part of this Locktoberfest has caused me to confront, surrender and be guided to this new found self-awareness; thank you.
Discipline
This lies at the heart of my kinkiness. And this is the thing that, in accepting this creates equal measures of excitement and anxiety, that has confused the f**k out of me. What I have found though through Mistresses guidance is that feeling excited and feeling anxious can be very similar, and as I have said I have experienced both these feelings intensely in equal measures during this week and from the very beginning. What I have also found and come to understand however is that both provide the same rush of cortisol to my brain, triggering my fight, flight or freeze responses.
So, with the strict discipline that has come with being in chastity and surrendering control of my orgasms to Mistress it has meant that I have had time to reflect on what is the difference between these two contradictory feelings?
My conclusion is simple: The difference in these two contradictory feelings I feel is down to how I perceive the situation and how I feel about myself!
And again, the beauty of this tease and the journey that has been guided by Mistress so far is this creation of a safe, sane, and consensual space from day one where no judgement whatsoever has been imposed in what is being asked, ordered, or demanded; in fact, it has been implicitly forbidden. This safe space is how I have come to confront, acknowledge, and change my perception of the immediate reaction to the intensity of these cortisol triggered feelings that literally overwhelms me from a negative feeling to a positive feeling and again for me this has been achieved through trust and obedience of Mistresses guidance.
This has meant that learning to accept when excitement/ arousal comes around, without self judgement as to the cause of that excitement/ arousal can be very scary for me (the initial cortisol trigger) as well as admitting to myself that what I am engaging in, looking at, or thinking and how it ridiculously turns me on (the testosterone trigger) leaves me often feeling very vulnerable – shame, guilt, humiliation, confusion mixed with and masking arousal and excitement being the typical scenario.
With this combination of denial and discipline to be always unquestioningly obedient to Mistress in not being able to gratify the urge to ‘beat one out’ when excited/ aroused unless permitted by Mistress, along with the training to serve Mistresses particular pleasures has left me feeling very vulnerable and in very scary situations at times as the truth is that I am having a mirror held up to me by Mistress with very cute and simple truths and questions, “No need to fight this anymore. You are safe with me. You know you want to admit it? It turns you on does it not?” And the biggest thing is that because of the consent to the inherent discipline and the unquestioning obedience, as Mistress so simply put so long ago, “I’m going to tell you some truths about yourself and ask you some simple questions and the answer is always going to be yes, Mistress.” Means that the reality is I have no other choice if I am to be authentic to myself – it is a fait accompli.
I am left with no option Mistress. I surrender. It is true and I understand now that I do not need to seek or get approval for what turns me on and arouses me. I am learning to accept that it just simply does.
Consequently, through this safe space, trust, and unquestioning obedience I am now starting to acknowledge that by defining approval in that approval means believing something is good enough or acceptable, I have always been seeking approval regarding my kinks and that which turns me on, I am asking for others to accept who I am or what I have done. What Mistress in this safe space has given me is an understanding that it can be nice to take the time to soak in and enjoy these feelings without needing approval or judgement! Ultimately it has made me realise that seeking approval from others often means I have not provided this for myself.
This means that I am having to learn to “Celebrate my successes and things that make me happy myself,” and I am learning that I “Do not feel that I need other people to celebrate my successes and happiness for me to do the same.”
For this, again, I cannot express enough the gratitude that being part of this Locktoberfest has caused me to confront, surrender and be guided to this new found discovery through discipline, trust, and unquestioning obedience; thank you.
Expectations/Attachments
With the third week of tease and denial over and the anticipation and building expectation of what potentially I would be made to undertake in week four I can only say that my desire for release was off the charts to the point it was becoming unbearable and interfering with my life outside of this tease. And as you can infer by the past tense that I am using that release came, in every meaning of the word, through the gift of Mistress on Day 23 and:
“Very good, since here is a nice bonus for you pledge takers:
From now on having an orgasm purely from anal . . .
. . . will no longer count as disobedience.
A nice incentive to learn to sissygasm, right?”
The anal orgasm – the first in my life - occurred yesterday, day 24 and was both a mixture of shock, disbelief and an out and out primal feeling. To say that it was life changing would be, in fairness, a bit of an overstatement, but what it was, was an experience I have longed for, for a very long time and it did not disappoint. And here is the point of me expressing this very personal and private experience. In the past when I have attempted to experience this much written and chronicled phenomenon I have always, I now realise, internalised trying to do this with the question, “Should I be doing this?”
What this tease and specifically so far this week is showing me is that “Should” is driven by the need for control, yet I now realise after my orgasm, of which my no longer swollen balls are very thankful for, is that they can serve as barriers that prevent me from achieving or experiencing what I want – the acceptable behaviour issue already covered. Yesterday’s task allowed me to reflect and accept that to overcome this and many other experiences that I would like to feel, I needed and need to focus on the positive consequences of doing whatever it is I know I want to do. So, instead of acting like I should be giving myself an anal orgasm, I asked myself, why do I want to give myself an anal orgasm? and what is the benefit of doing this?
The simple answer to all these questions, and this did not surprise me, was because Mistress is encouraging me to do so, and, more importantly for me it will not be seen as disobedience – which has been my main trigger from not ‘cumming’ in all the various other tasks and edging pledges that has confronted me with the choice of either please myself, or please Mistress.
So, in my final thoughts for this reflection, Mistress and this tease has taught me that if my expectations are not aligned with my values, I need to gently acknowledge this. I am learning to tell myself something like this, “this expectation, or attachment, does not help me now.” Yes, it can be hard to let go of these expectations and attachments, if it feels like a loss, yet I recognise that I must aspire to gradually release my grip. Strive for flexibility. Trust in the unquestioning obedience that is being asked of me by Mistress and allow myself to feel what it is I feel without fear, shame, or guilt because of that fact. I am in a safe space where I can be who I really am without judgement.
This week so far has culminated in seeing that it helps for me to change my “should” to “wish” and “hope.” This way, there is less attachment, and I am free to move beyond anger, frustration toward compassion, positivity, and solutions. The reason for this for me is that “Should” often takes the form of moralising, either to myself or to others. When I am moralising, I am connecting with my anger, using it, and staying with it. However, when I am wishing and hoping, I am gently connecting with the sorrow underneath frustration, disappointment, and anger—and reaching my core self.
Yes, I feel the pain that comes with my inability to fulfil my wish (being denied release when I want) but I also feel the joy that comes with the ability to fulfil it (having finally an anal orgasm because of the strict instruction of Mistress and her permission that it will not be seen as disobedience.)
jerking with the glove, vibrator and watching censored was both fun and frustrating, exactly what i expect from the daily sessions. The blindfold didn't do much for me solo. Still not ready for anal, which fucked me. The non-sexual part was pretty easy, would be way harder after a teasing session.
24:
Having a break day was nice, i enjoyed playing some video games without thinking about my poor locked cock. That is, until i had to do my censored edges for the pledge - i almost failed by going too far!
The past week has been fun, exciting but also frustrating.
I really enjoyed jerking with the glove, but it was over way to quickly as i got to the edge right in stage 1. Thankfully edging would be required for the next day and watching censored porn has been a kink of mine for quite some time now. So i was happy to agree to the censoredger pledge, only to find out later that this is the toughest challenge so far for me. Humiliation and pleasure go together here and it's not easy to prevent an accident - it's really a ride on the razor's 'edge'.
On that day i also went caged to the office for the first time, a totally new experience.
The most frustrating day was when i got to use the vibrator on my balls and cage. It felt so nice, and i leaked a lot and enjoyed licking it off my fingers. I was so close to cumming when Mistress Shyla said "Stop!" that i started humping the air automatically, but it didn't help.
As much as i anticipated to cum that day, was i surprised when it finally happened; from being blindfolded, caressed and vibed on my buttplug and balls, wow!
I don't know what to think of being fucked in the ass. On the one hand, it is pleasureable for some time, but i always feel like it doesn't lead to more.
I really enjoy reading the reports and thoughts of the other players here, especially from Emma111.
I'm excited what will happen on the last stretch of this experience. I'm now way beyond my record for being locked up on consecutive days (previous was 4 or 5 days). But i'm confident that everyone who got this far will also be able to finish Locktober!
Points Total (baseline + daily tasks + completed pledges): 1530
Basepoints: 12 -> 15
Cage: normal metal cage (switching to small one if privacy is needed)
Mode: privacy -> standard
It's hard to believe that there's just a week more. Just like it's hard to believe that I've spent all this time locked up and denied, that I managed to edge so much without accidents (so far, hopefully it'll continue like that), that I came with all direct stimulation being a dildo up my ass...
Sometime in week 2 or 3 I've started to believe that it's possible to get through whole month denied, and hoped to do this. But spurt on 23rd definitely was a release: for example in edging sessions before it took me just couple of seconds with one finger to edge, now I'm actually stroking quite a bit, especially at the beginning. I'm not that happy with this outcome, maybe I'll manage next year?
I'm second guessing my decision not to take the buttplug pledge, especially for these two last days that were less explicit than usual. An hour should be a managable amount of time to be plugged? Anyway, it's too late now, maybe it's a lesson not to cower from every little bit of potential discomfort.
25 days . . . I never would have believed, that I could make it this far into locktober ever - not speaking of being in a small metal chastity cage 24/7 for more then 3 days now. As I sit here listening to sissy hypno and feeling a plug pressed against my prostate I am more in tune with myself then I have been for the longest time.
The last few days with Mistress and you all here have made me realise that this is no fetish at all this is what I am, what I need and what I want. I want to live as a genderqueer chastity-addict pansexual sissy. I can no longer deny this and this realisation makes it so painful, that it took me this long to accept who I am and what I am. On the other hand I am so happy with this tease, and the interaction in our small community - especially my Sissy Sister Emmi - has let me to tear down all pretenses of morality or fear in my mind.
I don't know when and how but in this moment I feel very sure that the wonderful person living inside me has to come out of their closet to the people I love and with their support hopefully to the world. I feel very vulnerable writing this on the other hand it makes me feel very strong since I know that it is truth and I am sure against all odds truth and love are the two forces that will prevail in this universe.
As runner of this event I am so grateful for all the people who spent time with my and Mistresses creation so far and that will in the future and hope that we did guide you for the better. . .
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. I've also had some buttplugs of different sizes for stretching and prep (with a T-shape base so I can wear them for extended time!) and anal beads just for fun.
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. I felt completely full at this point, so I didn't want to push more. 
). Maybe my prostate took too much pounding to respond, or maybe it's the fault of orgasms I had past week 
. I definitely need more practice for this love-button to work as intended.
. I took the pledge, and I love that sissygasms are allowed from now on 
. I'll sure as heck try to finally achieve it this month.
. I'll sure as heck try to finally achieve it this month.
)
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. No other tease made me reflect so much on myself 
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) and will accept a punishment for sparing if the community wishes to.
