Sissy Sarah Chastity Slave – Second Visit

My Chastity Challenge Slave, Sissy Sarah returned to the House of Deelight for a special Christmas session to celebrate what has now been just over 4 weeks in Chastity.  Only another 48 (minimum) to go!  As per usual I like to get my committed and willing slaves to write about their experiences for my blog, so below is Sissy Sarah’s own account of what happened.  This is the start of another long-standing D/s Relationship and many transformations are on the horizon for this self-confessed Sissy.


My homework was complete and I was returning to the “House Of Deelight” for my second appointment to serve my Goddess, Miss Deelight. I entered and greeted Mistress in the same way. Mistress was obviously in a very festive mood as she was wearing a Christmas outfit; once again I had to be excused and regain my composure – I find Mistress totally overwhelms me with her presence and beauty. ” A quivering sissy ” mistress commented. I have served a few mistress’s before – but I have never, ever reacted and behaved in this manner; I am totally captivated and enchanted by mistress – she is my ultimate Fem Fatale. Once served never forgotten.


masked bitch

gifts for mistress

I was ordered to strip, but this time I was more provocative and a real tease ” Come on get them off” Mistress demanded impatiently. I didn’t have a bra on, but I did have pink stockings, suspenders and panties on – to cap the outfit off I was wearing a butt plug also. Mistress being laughing in sheer joy and utter delight at me; she really did approve and like my lingerie. I was then unlocked out of chastity and I was teased and taunted, verbally mistress really knows how to tease me, with a few well chosen phrases and her amazing body; she began to caress and touch and tease – whilst edging me – on and on and on. I was in heaven; Mistress sensing my arousal gave me a dose of very sharp nipple torture “you won’t be having a white Christmas this year” Mistress exclaimed.

sissy surrenders underwear

Part of my homework was to bring along my underwear – as I would no longer be allowed to wear it; mistress was confiscating it period. “This is your life now, serving me- do you understand ! ”  I paused and replied ” yes mistress I really do.  I then surrendered my underwear as an act of devotion and complete obedience.  Yes I am a sissy boi, I really enjoy the feel and caress of lingerie on my shaven body. Mistress insists that I only wear female lingerie from now; as part of my devotion to her. She will be checking occasionally; giving me no notice where or when this will happen.

inspection and humiliation sissy

Another part of my homework was to bring along some tinsel and a Santa hat; I would be required to sing a Christmas carol for 
Mistress, who was in a very festive and jolly mood, especially since her    ” Christmas Sparkle task ”  was complete and I had put a contribution towards the team effort. I was decorated with tinsel/ nipple clamps – I was ordered to sing, “Jingle Bells ” not once but twice in an opera style much to the amusement and enjoyment of Mistress.

plugged and caned

All had gone well up to this point, however I had failed in a task and was sentenced to 60 strokes of the cane, you may think this a little harsh; but I had totally got the wrong sized bottle of wine ( a large one) and Mistress was driving. The punishment did fit the crime – I was informed that it would be a cold canning and no warm up. Once again I was immobile and at Mistress Deelight’s mercy on the spanking bench. I have to admit I am starting to like the attention of Mistress Deelight’s cane. I reached the end of my punishment and Mistress commented “that is probably one of my best CP sessions” – while she admired her work. Mistress also revealed that CP was one of favourite activities and she would love to do a 90 minute session just with CP. I replied ” I am here to serve and not negotiate and will serve you in any way you desire” said I- I do have a feeling that I will be get better acquainted with her canes in the coming months.

locked and plugged Sissy cock

spiked wedges for chastity cage

I was then relocked in chastity, but this time Mistress wanted to extend my limits; as part of my homework I had to purchase: an ownership tag, some plastic numerical padlocks and some anti-pull out wedges. My chastity servitude would be tailor-made and personal to me. I was safe and soundly locked up again unbeknown to Mistress and I – at around 3:00 am the next morning when I awoke with my usual morning-glory incarcerated,  the pull out wedges began acting like spikes digging into me ; it was a curious mixture of pleasure and pain. I immediately crawled to my bathroom and sat on the tiled floor – the coldness reduced my ardour. I sat naked whimpering like a sissy bitch – and I thought – I really am fully emasculated now – it would be an endless cycle of tease and denial with Mistress; for the agreed 52 weeks.
tag of ownership

diamante chastity lock

Very early in the morning I received a text from Mistress she was thanking me for her gifts and checking my bottom was okay;
however it did end in a curious manner  ” ……..I have decided to make your chastity more rewarding for both of us.”

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