The Journey Pt. 02

The audience cheered with lewd familiarity, apparently, this was not his first appearance on stage, he rounded Chrissie and her eyes widen in disgust as she saw the creature that would make her a woman.

He flipped her head to the floor and expertly raised the rope so his cock was at Chrissie's eye level, a few moments for her to appreciate the hard work in store for her, a small tug and the head of the monster cock reached out to Chrissie's mouth. I could see the fear in her eye, she had wanted this for so long, her training took over, and her mouth opened wide, barely fitting the huge girth in, she pushed her head forward to let the unexpected length slide down her throat until she had managed to fit it all in.

I expected him to face fuck her, but he simply stood with his hand at his sides, enjoying the experience of the blow job, for Ten long minutes Chrissie slipped her mouth endlessly up and down his shaft, I knew her tongue was working the head inside hidden from us all, then he grunted pulled his cock out and grinned hugely as he shot a load of spunk on to her sweating face.

His erection lost none of its potency, but given the training I had received, I didn't find that surprising. He pulled on some ropes and Chrissie flipped up into the missionary position, his hands reached for her panties and ripped them from her waist, rather than throw them into the audience as we had seen Melanie's go, he bunched them into a ball, gave a smiling nod to Chrissie and shoved them in her mouth. He walked back and flipping another few ropes slowly spreading Chrissie's legs until they were splayed at 180 degrees.

She was fully exposed to the audience as the man calmly stood waiting out of her sight, another girl came from behind the screen, Knelt before him and a producing a tube of lube massaging it onto his cock. The audience gradually fell silent as he dismissed her.

The fat man moved quickly, one second he was standing behind Chrissie his cock dripping with lube, then suddenly he was between her legs, the purple head moved towards her waiting boypussy, he grasped her legs and in a single move took her virginity, pulling her back towards him, and thrusting his cock forward into her virgin hole, she screamed as in one movement the entire length buried itself in her. He started to slowly fuck her, on his back swing his cock would come entirely out and she cried out in pain as each forward swing brutally buried his cock fully inside her.

The fat man's rhythm sped up, I thought he would cum quickly, releasing her from the pain, but then he slowed again, for thirty minutes his solid cock moved in and out of her ravaged boypussy, slowly, quickly, he adjusted his rhythm to a beat in his head, and the audience took up a matching rhythmic clap. Sometime in that 30 minutes, Chrissie's moans of agony began to subdue, then I began to hear moans of pleasure as she gave herself to her life's purpose, her sweat drained body gleaned but her head flew back in ecstasy and finally, she screamed in pleasure, "Fuck me, master, oh fuck me."

The fat man continued to use Chrissie until finally, I saw a shrug of his shoulders; he lurched and then stopped moving. He waited a few seconds before withdrawing from her; he manipulated the ropes again, this time putting Chrissie into the doggy position. He turned to the audience spreading Chrissie's legs to show them her first cream pie; spunk dribbled out of her hole to fall and stain the floor.

A girl rushed onto the stage with a robe for the fat man, and behind her, I saw another naked man step out. The MCs voice came over the noise of the crowd, "Ladies and gentleman, Chrissie will not only surrender her virginity for your viewing pleasure this evening, but she will experience her first gang bang too."

I could not turn away from the TV set as man after man approached the fuck swing with his cock out, as one entered her poor abused boypussy another inserted himself into her mouth, for another 90 minutes I watched the woman I loved taken, by men and women, all sizes, all races, came forward to use her.

After almost 2 hours of solid fucking, they let her down, she was covered in sweat and spunk, her boypussy was still gaping wide even though it was minutes since the last cock had finished with her, she turned to the camera and grinned.

The TV died, "Five times Josie, you came for her five times," Jamie's voice quietly announced.

Head Mistress.

Mistress Anna collected me the next morning, she looked amused as she led me down a new corridor, "The Head Mistress wants to meet you girl, it's a big step, remember what you've been taught."

I rode a little wave of anxiety as I responded, "Of course Mistress." Our heels clicked in unison down the corridor, I was now managing four-inch heels, and above them, my boyfriend shorts were the same pastel blue as Chrissie has been wearing the day we first met.

Mistress Anna knocked on the door and opened it, "Sissy Josephine." She announced and led me into the study.

A large picture window opened on to a park, it was the first time I had seen daylight and the outside world since my arrival. In front was a mahogany desk, well built, antique, an IPad lay upon it, but otherwise, it was clear. No one sat in the matching high backed seat behind the desk.

From behind me a voice said, "Many a misbehaving girl has been bent over that desk, panties at her knees, bare ass in the air, weeping, while she received appropriate punishment for their transgressions." she paused, "Many, but not all, let us hope you are one of the exceptions Josephine, You may turn around."

I turned to see a large old green leather chair placed beside a roaring fire, sitting in the same uniform of a Mistress, was a slight figure, I would guess she weighed less than 100 pounds, but her eyes shone with an inner steel and it would be a silly bitch indeed who crossed that woman.

As I had been taught I curtsied, rising with a smile on my face, "Sissy Josephine at your service ma'am."

"I am the Head Mistress, this is my school." She pointed to a plain wooden chair, my memory flashed, it was the same one I had sat on in the first room, on my very first day, I was positive of that, "Sit Josephine, I have much to explain."

The Head Mistress explained that I had reached the point where my body was shaping up nicely, my posture was improving, and I was beginning to fully accept my future role, I was being promoted from beginners' to the intermediate class.

I would still see the Doctor daily, Mistress Anna would still take me through my morning exercise, but new classes were added to my curriculum, blow job training, basic sex positions, extra gym so my body gained the strength and suppleness needed to fuck for hours, Light BDSM, and of course we had to start stretching my boypussy so it could accept the men who would please themselves inside me.

Mistress Anna stepped forward and gave the head Mistress the small thin butt plug which had lain unused in my 3rd drawer these last 4 weeks.

"Once this is inserted, you will initially find walking difficult dear. You must wear it for the hours of your school day, but you have no need to wear it for longer if you don't want to." The head mistress spoke while her hand, long years of practice expertly lubed the plug, "Most girls find they enjoy the experience and keep it in all day, but the mistress in your last class day will always ask if you want it removed."

"Step out of your boy shorts dear, spread your legs, and bend over my knees."

I did as the head mistress instructed, the was a slight resistance as my hole accepted its first object, I had never even inserted a fingertip in it before, I almost came such was my ecstasy, my boypussy had finally been entered, it wasn't a cock, so technically I was still a virgin, but I was one more step down the road to sluthood. The head mistress, years of long experience was expecting this and her hand rounded my sissyclit and with a quick expert squeeze kept her floor clean.

The butt plug was short only three inches, and thin, it's wasn't much thicker than my pinky and it settled in place with little real difficulty. I still gasped a little as the head mistress got it properly seated, then with a light spank on my ass she said, "You may get dressed sissy."

Once I had my shorts properly arranged, I curtsied again, "Thank You Head Mistress."