29th December 2018

Sissy Nicole’s session with Mistress Nicky PT1

As i descended the stairs to the basement i am filled with a familiar feeling of excitement and nervousness. Mistress Nicky was allowing me to be her sissy maid for the afternoon. I was excited , as every visit to Mistress was a different journey into the unkown. Always a little scared though , that i would displease her in some way and end up being punished for it.
As Mistress Nicky welcomed me into her domain , i was told what duties and activities would await me during the afternoon. One of the first tasks was to transform to sissy Nicole , so a pink latex dress was slipped on , as well as a ponytail mask , stockings and stiletto boots. Then the pleasure and pain started. Pain first. I had to read Mistress Nicky a story i had written. I had to read it whilst bent over a storage chest raising my bottom as high as possible into the air. A selection of canes were placed to one side and with a shiver i began the story.
I could see Mistress choose a cane as i nervously started reading. “Louder” , she called , as the first stroke landed. A swish followed by a thud and intense pain took my breath away. I upped my volume, but the strokes kept coming. I tried to thank Mistress for my punishment , but that just interrupted the story and led to even more cane strokes. My body was shaking and i was really struggling to hold the position. My bottom was now on fire from the punishment , but i continued to read from the pages in front of me. Mistress would change over to a different cane after a number of strokes. Each one brought a different level of pain. Some light giving a very stingy blow , others more heavy , landing with more of a thud and pain which took longer to reach full intensity. Finally i reached the last sentence , at which point Mistress Nicky took aim and landed six of her best in quick succession. Pain at its most intense , but i managed to hold position. At last i was able to thank Mistress for my punishment and was happy to know that the marks from it i would carry for a long time. My rear end now matched in colour the bright pink dress that i wore. Mistress Nicky now orders me to make my way to the fuck bench…

The fuck bench was in the middle of the room , and it was onto there, face down that i was next secured. Mistress Nicky also announced at this point , that i was to be fucked live on webcam for anyone who cared to watch. A shiver went up my spine both at the prospect of being well and truly fucked by Mistress , but also the fact others were going to watch. Mistress Nicky tightly bound me to the fuck bench and then proceeded to open me up. I felt a cold stream of lube running down between my ass cheeks , then Mistress started by inserting a finger , then two and then three into my hole. After a short while Mistress stopped and went off for a brief moment only to return with a thick black strapon firmly attached to a harness around her waist. Mistress Nicky grasped the phallus in her hand and held it upwards towards my face. “start licking” , i was ordered , and i immediately starting to run my tongue up and down the shaft of her enormous deeply veined and contoured dick. She made me lick her balls and run my tongue all the way to the head, at which point she thrust it into the back of my throat. I gagged with the huge cock in my throat and then mistress took her now spit covered cock around to my rear.
Mistress was gentle at first , she slid the bulbous head into my hole and i gasped as i was opened wide. I began to be fucked , at each stroke Mistress drove the cock deeper into me and i began to cry out and pant with each stroke. Both the pleasure of being fucked but there was also pain of being stretched both wide and deeper. At this point Mistress Nicky stepped up onto the fuck bench , her body directly above mine , she was able to drive the cock’s full length deep inside me. She pumped into me hard and fast , balls now slapping against my own , i felt my own cock start to leak cum into my condom covered chastity cage.
Then Mistress withdrew and once again presented the cock to my face for cleaning. I greedily licked and sucked both the lube and my very own juices which were now dripping from Mistress’s strapon. Every last drop went down my throat , and i heard Mistress Nicky giggle as she went out of my sight only to return with a fresh glove on her hand. I instinctively knew what was in store for me next…

Mistress Nicky once again approached my rear. The black strapon now dangling between her legs like a real spent cock. Once again i heard a familiar click , then more cool lube started to drizzle between my ass cheeks and arrived at my now opened up ass pussy. Mistress began inserting her fingers once again , but all four were now pushing into my still resisting ring. As Mistress kept pushing her fist towards me i began panting as my pussy gradually opened up to accomodate her pending fist. Then finally i let out a gasp as her whole fist slid into me and i had the wonderful feeling of fullness and satisfaction that Mistress was now inside me.
Mistress was gentle at first , slowly fucking me and moving about inside me. Then Mistress withdrew her fist from me , only to pump it straight back in again. Then she began to push her fist in and out of me , with increasing speed , and once again i felt my cock leaking more juices into the condom. Mistress withdrew her fist for the last time and once again went out of sight , only to reappear with an even larger cock. This time Mistress had chosen donkey dick. The longest phallus i have ever seen with an intimidating head, it sent a shiver through my body in anticipation. With lube still glistening all around my rear end , Mistress pressed the helmet hard against my ring, and my now trained pussy had no choice but accept its huge length. As Mistress fucked me with it i could feel the enormous head inside me and the deeper it went , the more my ass cheeks were prised apart. Mistress pumped the cock in and out of me , occasionally withdrawing completely , to once again pop the head pass my now sloppy entrance. Then finally Mistress withdrew the shaft for the final time and i lay there quite still , exhausted , stretched , sore , but very happy.
Mistress now informed me what she had in store for me next. My arms were placed in an arm binder , and i was made to kneel in the corner of the room facing the wall, awaiting my fate…

To Be Continued.. 😉

Cross Dressing, Sessions, Sissification, Testimonials, Uncategorised