Journey of a sissy slave

I sit here plugged and wearing probably the most important t-shirt I have ever owned while waiting for a new chastity cage to be delivered this week. How did I reach this wonderful moment? It has been an intense and highly enjoyable last 5 months thanks to being spotted and enslaved by Mistress Bethany Roberts. However my journey started over 30 odd years ago and probably longer if you included watching the two ronnies and falling in love with “the worm that turned” storyline.

In the back of my mind for the last 30 odd years has been the need to surrender to Superior Women and I have had the joy of service at various points through that time. However I was also creating a vanilla world while denying my true nature. Eventually your true self overrides everything and fate takes over and this is what I suspect has happened to me. There is a time when vanilla is not enough and fate forces you to reconsider your priorities. Fortunately Mistress Roberts appeared in my world as I was realising the need to be true to myself. I was not seeking Her nor Her me, but paths crossed my life has changed forever.

Mistress Roberts, is the first Superior that I truly have zero resistance to. In the past I had a vanilla world to use as an excuse not to truly obey which meant that some of my previous experiences were probably on my terms rather than embracing submission. However with Mistress Roberts, there is no thought of pleasing myself or disobeying Her. This mindset is constantly reinforced by Her training and Her training is superb. Yes there is a high degree of financial domination which is not everyone's cup of tea, and at the beginning I was nervous & worried but the money is unimportant but it symbolises so much.

Mistress Roberts demands complete servitude and devotion on Her terms which is easy to learn. She forewarned me of Her ambition and what Her training will do to me. In my eager puppy state, agreement was easy and rapid. Since then there has been no looking back and fully embracing Her magnificent control on many aspects of my life while still respecting vanilla commitments. Mistress Roberts has quickly identified triggers and embedded new ones which help push me deeper into complete submission. Her skill is exquisite as well as elegant.

In the last few months, I have bought numerous toys including an array of dildos and butt plugs, clothing including heels as well as modified my life to be used by Mistress Roberts. At first I was obviously obsessed with masturbating over images of Her. However this has now evolved into no more masturbating to release and the use of a Doxy while caged. Chastity devices did start fairly large with some space. The space came with its own issues of sleepless nights etc. However now I'm on the shrinkage journey as Mistress Roberts has gradually tapped into a latent desire to be a sissy. Milking is only permitted when dressed and caged. I am also very aware that erections are not to be tolerated if I am to be a good sissy.

Upon reflection of the last few months, I have fallen deeply into enslavement without realising it happened on day 1 of that first conversation when all I could think about was obeying Mistress Roberts. This still rings true today and long may it continue. The key aspect is to always remember Her commands or wishes which are Mistress Roberts dictates everything & always be plugged (hopefully caged once the new device arrives).

Thank you for reading this and look forward to sharing more.

 

Thanks for your reply. Mistress Roberts dictates everything and knows best so i feel secure in the knowledge my future will be just fine.

 

Thank you to all who enjoyed or read the first instalment. It is nice to share and express matters to such an appreciative and supportive group. After many years of being unable to embrace my true self and repressing emotions, it is a true pressure release to share.

This week finally saw me buy a correctly fitting chastity device from House of Denial. The chastity journey with Mistress Roberts has been interesting with a few bumps along the way. I’m no stranger to chastity but i’ll confess that i’m ned to the idea of shrinkage. Previous chastity play was just that play for a few hours or a few days, nothing of any significance. I have experienced cheap plastic ones which cracked as well as a steel one which the ring size was slightly too large and would slip down too far.

Fortunately Mistress Roberts understands the pitfalls of ill fitting chastity devices as well as the benefits of a correctly fitting cage. Over the last few months, I have bought 4 devices to find the correct size. (CB600, HoD300, S215, & S221)

However the first 2 were not bought with the idea of shrinkage being the goal. In Mistress Roberts wisdom, She instructed me to buy the devices to keep me caged and get me accustomed to denial again. She has since kindly informed me that if She asked me to buy smaller devices immediately I might not have been ready to start the shrinkage journey. The S215 and S221 are smaller cages and in my enthusiasm i bought the S215 too quickly and is now my aspirational cage. Over the last few nights I have finally experienced the benefits of the correctly fitting device, no swelling from the friction of arousal, no skin catching in the ring of the HoD300 and no heavy weight between its legs disturbing its sleep. The S221 is light compact and is hardly noticeable under panties.

The other joy of a well fitting cage is that Mistress Roberts kindly milks me while locked. As previously mentioned, my toy collection has grown extensively and for good reason. Mistress Roberts drains Her sperm in various means with various toys. The current method is a wand inserted in its hole and a doxy on the cage while She kindly trains me to stop the nasty habit of masturbation and slowly moves my arousal spot away from the vanilla ingrained association with its male genitalia. With the correct fitting device, erections are no longer feasible and they are no longer desirable either. However, sharing this points to a chastity community feels like I'm teaching people how to suck eggs. It's just a revelation and a correctly fitting cage enhances some much!

Another area of wonderful training is its collection of plugs and dildos. Mistress Roberts has kindly and methodically been stretching me wider and wider for longer periods. At first it was some cheap beginner plugs which within a 2 or 3 weeks were no longer fit for purpose. Then i moved onto the doc johnson range of plugs and these are now a constant part of my life. There was a period that I would use a small to medium size plug for daytime even when going to the office. Train rides are fun when plugged. Mistress Roberts would also require me to use a smaller one overnight. Now my day and night time plug is a large one and boy do I miss it in the moments that i’m not plugged. There is a growing comfort from being constantly filled. However the plug that is causing the biggest stir, is what is known as the largest plug. It is 3 inches wide and 8.5 inches circumference and provides a fullness that is on another level. I have managed to take this 3 times so far in the last couple of weeks. The aim is to be able to accept this more easily than currently and continue the journey of stretching while shrinking. However the greater goal for being plugged so frequently, is to be used by a Bull for his and naturally Mistress Roberts pleasure. There is a deeply rooted wish to be Mistress Roberts cuckold sissy slave which manifested itself the first day that I had the joy of admiring Mistress Roberts twitter feed. This has now morphed into wanting a bare large cock deep inside and feeling it pulse sperm deep inside my hole.

Thank you again for reading and hope you enjoy my sharing.