The remainder of their journey to Japan was a relentless adrenaline rush, leading us towards the grand finale in Tokyo. We both checked into an exclusive hotel that had been recommended by Suki - the dominatrix who had shown them how to open up and be uninhibited - and as they surveyed the magnificent surroundings, I silently thanked fate for being able to cancel the original booking.
The suite was huge and I didn't question how we could afford it. Jan immediately pointed to the bedroom and said that she wanted to start our fun right away. I eagerly followed her inside. Jan began to get her phone set up to record our session, something she told me she was planning on our way up in the lift. She handed over the key to the cage imprisoning my cock. She then instructed me to go shower and make sure that I shaved everywhere and cleaned myself inside and out - she even provided a small mirror so I could inspect my handwork afterward for those hard-to-reach places.
'We'll get you properly waxed when we go home so that it'll be normal that you are hairless below the head,' she cooed.
Smiling at the thought I followed her command and was soon hopping into the hot shower and carefully attending to every single inch of my body as instructed by Jan; shaving meticulously around every crevice, making sure especially not to miss any hairs around my freed cock, bum cheeks or inner thighs. I made sure to use the showerhead to give myself and thorough cleaning, paying special attention to my ass. This caused me to sprout a boner that was fraught with anticipation of our last night. When I was finished I stepped out of the shower feeling clean and refreshed, taking a moment to admire myself in the full-length mirror before covering up with a fluffy white bathrobe that hung on the back of the door.
I made my way back into the bedroom where Jan sat cross legged as she patted the bed next to her. She had changed into a brand new figure hugging latex dress along with very high black shiny heels. My jaw dropped at the sight of her. My eyes also quickly noticed, laid out on the bed also, was the schoolgirl outfit that they had gotten for me at the start of the trip.
Jan turned to me as I sat next to her, running her hands up and down my body as she spoke quietly in my ear,
'Time for you to learn how to be a good student again,' she said with a coy smile, 'although this time we have an audience again. Wave to Casey, Tiger.'
Casey was the flight attendant on our flight to Japan that Jan had already invited her into our playtime when she rang her and made her watch me cum all over my hand and chest a few nights before. I wasn't expecting this to be a live show so I gave a timid wave and suddenly felt self-conscious. There was no response from the other end but knew Casey must be watching intently. The feeling of self-consciousness was a stupid feeling as I knew Casey had seen all of me already in a very compromising position and knew our dynamic perfectly well.
My heart pounded in anticipation as Jan began helping me out of the robe and to get dressed in the schoolgirl outfit, adjusting pieces here and there until I was fully decked out and looking every bit like an obedient student ready for their teacher's lesson, again. All that remained was for me to slide my feet into the shoes that accompanied the outfit, completing the look perfectly.
Jan then led me to the vanity table where she carefully began applying makeup to my normally blank face. She drew attention to my green eyes by adding a light smokey effect, highlighted my cheekbones with bronzer and gently added a hint of lip gloss before finally styling my hair into two girly pigtails. As I watched in the mirror, I felt myself transforming more and more into what Jan wanted me to be - her girly little student who was ready for her lessons.
It felt like we were both caught in time as we surveyed Jan's handywork, when suddenly Jan snapped herself out of it, breaking the spell between us. She grabbed ahold of my hand again and led me across the room towards an empty space in front of our large windows that overlooked all of Tokyo.
'Let's start this lesson shall we?', she said with a wicked smile on her face as she picked up her riding crop from nearby and pointed it towards me expectantly.
I didn't need telling twice. I planted my hands on the window after lifting my skirt over my hips and stuck out my ass. I heard Jan chuckle slightly before I heard the first lash of the crop traveling through the air and land across my ass. I took a deep breath and winced as the pain quickly dissipated and the pleasure took its place. Each lash of the crop felt amazing and sent a chill down my spine as the crop hit me where I craved to be touched the most.
'Pull your skirt up higher,' commanded Jan as she lashed the crop against my panty clad skin.
I lifted my skirt up higher above my waist and leaned my face against the cool glass and gave a shiver as the coolness heightened the warmth I was feeling on my ass. This was certainly a moment. I could feel it as some sort of electrified wave of pleasure crashed over my body. My free cock swayed stiffly as Jan continued to bring the crop in contact with my reddening ass cheeks. I could only imagine Casey watching this scene wishing she could join in. My eyes caught movement from the building opposite and I wondered how many, if any, people could see me right now. What a shock it would be to see a girly man being tormented by his mistress while dressed as a Japanese schoolgirl and his cock on display to everyone.
WHACK.
Another strike hit me and I could feel a drop of pre-cum fighting to escape from the head of my cock. I got a little shock as one of Jan's warm hands caressed one of my ass cheeks. She was caressing me so gently and I could feel her fingers lightly running across the edges of my panties.
'Easy Tiger. It's OK. Relax and enjoy. I'm taking good care of you.' Jan said softly in my ear as she leaned over me and kissed me lightly on my cheek while her other hand pulled my panties slightly down my ass but still containing my now thick and pulsing cock.
'There we go. You have such a firm and sexy little ass. So perfect,' she cooed as she I felt her hot breath on my neck and the softness of her lips on my skin.
'Shall I tie your hands too? Would you like that? I'll do whatever you like Tiger darling. Tonight is all about you,' she said as she now caressed my back with her other hand.
'I am at your mercy, my pet. I am yours and you are mine. I am your mistress and you are my slave,' she whispered before pulling my head back by my ponytail.
The sensation of Jan's lips on my neck and shoulders as she uttered her filthy words to me was intoxicating. I could feel my cock throbbing and oozing more pre-cum as she continued to whisper her inanities in my ear. I moaned and pushed my ass back against her hand as she continued to caress my bare cheeks before reaching lower and around my hip to slide a finger inside the band of my panties brushing against my shaft. She began to easily slide my panties down my legs and let them fall to my ankles.
'Stay put,' she ordered.
I didn't move as I knew she had taken my silence to her question as an affirmation. I could hear her retrieving the cuffs from our bag of toys and waited for her to come back to me.
'Hands fully behind your back,' she said, 'and spread your ass while I shackle your wrists.'
The cuffs were soft and Jan worked quickly. They restricted my hands while I remained pressed to the glass by my face. I could still feel her behind me as she kissed my back before speaking plainly once more into my ear, 'I'm going to put a gag in your mouth now so that Casey can hear everything that you moan and scream. I don't want her to miss out on anything of our little time together,' she said as she lightly began to pull my head back by my pigtails.
She ran a finger over my lips before kissing me hard and long on the mouth.
'Now suck,' she ordered as she produced the ball gag and pushed it into my mouth. I rolled it around on my tongue and tried to get used to the feeling of having my mouth bound again. I loved the feeling of helplessness that the gag gave me. The fact that I could not respond with words to Jan just drove me on further to obey everything she told me to do. Once in place. Jan crouched at my feet and helped me step out of my panties. She then reached around and gave my hairless little cock a few light strokes.
Walking away, I heard her pick up her phone and bring it around for a better angle.
'What do you think Casey, do you think he is aroused enough?' she cackled.
Although I couldn't see or hear her response I knew it was good as Jan groaned and said,
'Mmm, yes, Casey, you look so tasty dressed like that and spread for me.'
Casey must have been facing the camera and on full display as she was watching us together on her phone. I wondered how she must have felt. I knew she would be aroused by the show, maybe even wet. The thought of her getting off was exciting, causing my cock to jump.
Jan continued, 'He is ready. His cock is so hard right now. Maybe you'll get to experience the delight of having this control over him soon. I'm going to torment him a bit more before I let him cum. Would you like that, Casey?' Casey must have replied something affirmative as I heard Jan breathing heavily into the phone.