4th January 2019

Sissy Nicole’s Session With Mistress Nicky PT2

I had been told by Mistress to expect another maid to join us during the afternoon. What would take place was uncertain , but as i kneeled there i was shivering at the very prospect of what might take place. After a few minutes there was a tap on the door and i heard another of Mistress Nicky’s sissys enter the room. I remained silent as ordered , and listened intently as Mistress guided the new arrival into an adjoining room. I tried to understand what was going on. I understood the sissy was named Abigail as i overheard Mistress preparing her for the session ahead. I then heard mistress’s familiar footsteps approaching me and once again felt my bottom being penetrated. A small plug was inserted to the hilt , and just when i was thinking how comfortable it was , Mistress started pumping a bulb hanging from it. My pussy was being filled , from a nice and filling stage until a very full and uncomfortable point. The plug was firmly in place so i had no choice but to remain in position, grunting as quietly as possible , hoping Mistress would soon relieve the pressure.
I heard Mistress setting up the fuck bench behind me , strapping Abigail into position. Then finally Mistress Nicky approached me again and deflated the plug invading me. I was told to go and get a small dick and attach to a strapon harness around my waist. Then as i approached the fuck bench , was told to fuck Abigail with it. Abigail lay face down , wearing a sissy hood and a black bodystocking. She had already been prepared by Mistress , and so my strapon easily glid into her sissy cunt. I began to fuck her with my new artificial prick as my own still useless caged one dangled beneath it. All the time Abigail moaned as i thrust my shaft in and out of her. Then Mistress told me to withdraw and present the cock at Abigail’s mouth. She eagerly took the member into her mouth and i was happy to then fuck her mouth with it.
Just when i thought Abigail was going to get all the attention , Mistress Nicky approached me and ordered me to bend over in front of Abigail. Mistress was once again wearing the large black contoured strapon and proceeded to fuck me with it, in full view of Abigail. Even though Mistress had already fucked me earlier with the same one , it still made me gasp as she drove her length all the way into me , balls deep. I was then told to return to between Abigails legs and resume fucking her with my strapon. As i guided its length back into her, Mistress Nicky approached my rear , her black strapon still firmly attached.

As soon as i had fed the full length of my strapon into Abigail , Mistress Nicky placed the head of her own strapon between my cheeks and guided it into me. I was now ordered to start fucking , but i now found myself having Mistress Nicky going deep into me, as i withdrew my own length out of Abigail. It was the wonderful experience of fucking someone and the feeling of being fucked at the same time. Even though my dick was safely locked away and feeling nothing , my ass pussy was getting all the sensations my fellow sissy was no doubt getting as well. My cock was only good now for supplying the occasional drip to the still collecting condom. In this position , i could have happily carried on all day. No release of cum to bring proceedings to an abrupt halt , just a constant stream of pleasure. Mistress Nicky had other ideas though , so as she pulled her phallus from my hole and instructed me the same , Abigail was released from her bonds and led to the bedroom with myself in tow.
Abigail was made to present herself on all fours on the bed, her bottom high in the air , exposed and vulnerable. I was then presented with the next instrument i had to use on her, a gag inserted into my mouth and secured in place. From the front of the gag , a rubber dick extended from my lips. Fucking Abigail seemed order of the day , so once again i attended to my duties, my head between her cheeks and pumping my head back and forth. Never before had i been so close to the action , but loved the view and the delightful sounds coming out of sissy. It was difficult to see anything else apart from Abigails cheeks oscillating in front of me , but i was aware Mistress Nicky was attending to the sissy’s other hole , her moans becoming stifled with her mouth full of cock. I was then given a vibrating wand to use , so i proceeded to run it up and down the gap between her legs and all the way to the tip of her now bulging cock.
Mistress then commanded Abigail to sit facing me on the bed. The juice filled condom hanging on my chastity cage was removed and Mistress fed it to Abigail , who swallowed every drop. With the gag now removed from me , i had to run my tongue over Abigail’s stiff shaft. Then finally Mistress made me take the head of her cock between my lips. Abigail’s now nicely swollen head filled my mouth and i greedily began sucking and running my tongue around it. I then took her deeper into my throat , working back and forth on her , now very expectant of her impending release. “i want you to hold it in your mouth when she comes”, Mistress instructed. Within a short while , Abigail shuddered and a thick stream of hot gooey cum was released into my mouth. “Show me!” , ordered Mistress Nicky, and i tilted my head back and opened my full mouth to her , trying to avoid any spillage.
I was fully expecting Mistress to announce “Swallow” at any time , so was surprised to hear her tell me to kiss Abigail and give the load to her. I did as instructed and Abigail took all of her gift back from me and then gulped it down her own throat. I just had to settle for the lingering flavour of my cum mouthwash. So finally another day of training came to a glorious end. Nicole is now eagerly waiting to be able to serve Mistress again, in whatever way Mistress chooses.


Cross Dressing, Sessions, Sissification, Testimonials, Uncategorised
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