Little Bo Peep - The Eight Outing

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 setup 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 afterwards 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,

'Mmmmmm 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.

'Mmmmmmm yessssssssssssss, He's hard and ready for your touch Casey. He's all tied up and at my mercy,' she said almost panting into the phone.

'But I'm not quite ready to let him cum just yet. I think I'll make him suffer a little longer. He needs to learn his place and I enjoy making him wait.' Jan finished.

She put the phone back in the perfect position to capture every detail. Then, stepping away again, she began to unpack her strapon, carefully selecting which one she would use on me. I watched in the glass and from my peripheral vision as much of her standing in her latex dress as she orgnaised the harness and slid it up her legs and fastened it in place. Her eyes skimmed over each of the two dildos she could choose between, before settling on the thick one that curved slightly at the end. She then proceeded to slip it into the harness and walked back towards me. My heart raced as I anticipated what was about to come next. Jan surprised me and knelt down in front of me, still in all her erotic glory, and placed a hand gently on my thigh.

Surprisingly, her mouth engulfed my cock and she proceeded to give me a blowjob. It had been some time since she had given me a blowjob and I knew this long awaited treat was coming in part because of Casey's presence on the phone. She sucked tightly on my cock as she bobbed her head up and down. I could feel her lips spreading as she took more of my cock into her mouth. I moaned into the ballgag as I enjoyed her ministrations. She acknowledged my enjoyment by sliding her hand firmly up my thigh and giving it a squeeze as she began to move on my cock faster with her wet lips. I closed my eyes and concentrated on the feeling of her mouth working my cock. I was moaning into the gag now and I could feel her sucking harder. I knew I was close and I tried to push my hips towards her mouth but she kept me still with her hands on my hips and slowed down. She looked up at me from my cock and smiled as she could feel how desperate I was to cum. Her fingers danced their way to my asshole and she began to circle it. Her mouth barely moved as she did this.

I could feel an orgasm building, my cock pulsing with every beat of my heart. I gasped once more through my gag and Jan just shook her head slowly, her lips firmly wrapped around my cock.

'No, Tiger, I don't think we're quite there yet. It seems Casey would like you to suffer a little longer,' she said as she slowly extracted my cock from her mouth.

She stood back up and began to stroke my cock in front of me, her hand firm and deliberate as she looked me in the eyes. She wasn't going to let me cum, not yet. She continued to stroke my cock but it wasn't enough to satisfy me. I pushed forward into her hand, begging for more and she simply smiled.

'You've been so obedient today. Let me see how long you can hold out,' she said as she stepped back behind me.

I heard the unmistakable sound of the bottle of lube being opened.

'I'm going to enjoy the hell out of this,' she said as I waited with baited breath for her to touch me.

Her fingers found my asshole again, dripping with lube as she circled and teased me. I moaned loudly into my gag, unable to hold it back. She continued to finger my ass as I drooled from my gag.

'I love how slutty you look right now,' she whispered as she withdrew her fingers and pressed the thick head of the cock against my asshole.

There was no way I was going to be able to stop myself from cumming if she continued to tease me like this. She started to press more firmly and I leaned forward against the glass as I felt her push into me. I groaned and grunted hard as she penetrated me slowly. Her hand grabbed onto my hair again and she pulled my head back as she thrusted further into me. My ass throbbed as she slowly penetrated me deeper with each pass.

'Is it what you've been waiting to see, Casey?' she said out loud towards the phone, 'it what you want?' she repeated while she quickened her movements into me.

'Oh fuck yes, he this view is amazing. Can you see how hard he is?' she said as her thrusts got even faster.

'I can feel his cock throb as he gets closer and closer,' she grunted as she continued to fuck me. I could feel her hands on my hips, driving the dildo in and out of my ass. I was filled and empty in equal measure and the sensation of it was almost too much to handle.

'Are you getting close too Casey? I'll bet you wish you could be here, don't you?' Jan joyfully said. You could help me clean up the mess once he cums all over the windows here.

And with that, Jan withdrew from my ass and grabbed the phone. She showed Casey a close up of my gaping hole as it winked back at her. Her finger gently stroked my hole as my ass was pulsing with every passing second in the hope she would continue and I would be offered the privilege of going over the edge. Jan looked at me with an intensity that said she could see right through me and dropped one last kiss on my lips before dropping to her knees again.

She grabbed the base of my cock and started to take me into her mouth, her eyes never leaving mine. She sucked hard and deep on me and I could feel my heart pounding as I fought the urge to cum right away. Her head bobbed up and down on my cock as she deep throated me while holding the phone to the side for Casey to watch. She paused just enough to say,

'Do it.'

I felt myself getting closer and closer and those two words were enough. My entire body tensed up as Jan held the head of my cock in her mouth and teased out every last bit of pleasure from me. I gasped loudly into my gag, my cum spurting into her mouth as she milked me completely until I had nothing left to give. She pulled away slowly and smiled as a satisfied grin spread across her lips. Standing between me and the glass continued to hold the phone expertly as she showed Casey the result of her skills. With no warning her free hand undid the ball gag occupying my mouth and let it fall to the floor where it bounced once and then stopped. Her mouth then pressed against mine as she forced my mouth open and shared my large load between us. With her free hand she pulled back and caressed my cheek as she looked me in the eye with a look of satisfaction before returning to kissing me deeply.

My salty and warm cum sat in my mouth briefly before Jan nodded at me and I understood.

'Good girls swallow, don't they?' she whispered as I savoured my taste.

She then turned and grabbed the phone from Casey and panned the camera up and down my body as I swayed for the benefit of Casey on the other end. My ass was red from being flogged and the pounding it had just taken.

'I hope you enjoyed the show. So did he. All going well, we hope to see you soon,' she said and placed the phone back down carefully where it was before.

For the first time that night I heard Casey's voice responding but I no longer had the strength and I rested my face against the glass as I heard her speaking. Jan undid the cuffs around my wrist and ushered me over to the bed.

'Say good night to Casey, Tiger,' she giggled.

I sighed contentedly and said my goodbyes. Japan had been amazing. I couldn't imagine the exploring that we had done would have taken such a turn. The intensity of what had just happened was slowly sinking in. I was more trusting of Jan than ever before and I trusted my wife that we would get there with Casey. If that's what my wife wanted then I would happily oblige. I had no idea how these new developments in our relationship would play out.

Jan flopped down next to me, her dress and the strapon now a pile on the floor. I traced my hands all over her body. She was glowing with pleasure and it was contagious. She was smiling in a way I had never seen before. Her entire body radiated with satisfaction. This was even new territory for us and I was excited for what was to come.

'Now finger me until I cum,' she demanded.

 She spread her legs and I began to run my finger over her wet pussy.

'Please do it fast. I need to cum' she groaned.

I gently slid my finger inside her and began to move it in and out.

'Faster, faster,' she demanded, and I did.

She held onto the bed sheets as I sped up my movements.

'I'm so close, come on. Fingers me harder' she squealed, and I obeyed.

'I'm going to cum, you little bitch,' she said as I grunted and pushed my fingers into her even faster.

I felt her body shudder under me as her orgasm hit her.

'Oh fuck yes, Tiger, I'm cumming,' she screamed, and I felt my hand being pulled inside her as she clenched her pussy around me.

Both of us lay sweaty and panting. I kissed her on the lips and smiled as I propped myself up on my elbow. I got up and pulled a reluctant Jan, we made our way to the bathroom.

Japan had turned out to be everything and nothing like I expected. Needless to say, we were both going to be both happy and sad to be leaving in the morning.