Little Bo Peep - The Fourth Outing

As dreams of Jan dominating me filled my head I was awaken by a gentle hand on my shoulder rocking me slightly. Casey, the tall and stunningly attractive cabin crew in charge of our section was waking me up.

'So sorry to wake you but you sounded like you were having nightmares and needed to make sure you were OK,' she told me. 'Also, I've brought you dinner.' She indicated the tray on the table off to my left where there was a covered meal ready to be eaten.

'OH thank you,' I sheepishly responded as I adjusted myself in my seat.

One of my feet accidentally kicked the storage under the screen and I watched in slow motion horror as the panties I had stored there shortly before I'd dozed off had been resting and began a slow tumble to the floor of the plane.

My heart sank and I fearfully looked towards Casey, expecting her to look at me with suspicion or even disgust. Instead, she gasped and laughed, bending down to pick up the underwear from the floor.

'Tom!' she scolded with humour in her voice. 'What have you been doing here?'

She picked them up and examined them. Once happy with her inspection she placed the panties gently on the armrest of my chair and gave me a stern yet somehow kind look that seemed to say 'we both know what this is about but let's just leave it at that'.

I blushed but couldn't help smiling back as I thanked her for her leniency and understanding. After all, if there was anyone who could understand naughty behaviour on a plane it would be a flight attendant like Casey, she must have witnessed so many different things. Nothing like this I'd have imagined though.

I readjusted my seat and Casey grabbed the tray from the table and put it on my lap before turning her attention to Jan who was starting to stir. Once Jan had her meal as well, Casey left to attend to the other passenger. With gentle yet firm words she reminded me that although certain activities were not allowed during flights, if we really couldn't control ourselves then they must be kept discreet. Jan started to put two-and-two together as her eyes darted from Casey to the panties, to me and back. Her cheeks blushed and said she'd make sure to keep me in line.

The rest of the flight passed by uneventfully. I watched a few movies, played some games on the screens with Jan and other passengers. Jan went to shower at one point before we eventually started making our preparations for landing. When our "pods'' were back in their tidy state and I had made sure to carefully fold away my panties and remember my butt plug at the last second, Casey came over to do one last check. Bending over me to whisper to Jan as she handed her what looked like a business card. I could smell her light perfume and tried my best not to stare and her exposed neck. I thought nothing of it as we made our final approach to Tokyo.

We landed, said our goodbyes and thank yous to Casey. I had my eyes downcast as I told her, 'Thank you for everything,' before hopping off the plane.

We quickly made our way down to the baggage claim to get our suitcases. We'd heard so much about Japan and, after all the stories we had heard from friends and family, it felt like a dream come true to experience it for ourselves. Once our bags were safely in our possession, we left the terminal, hailed a taxi and set off into the bustling city of Tokyo towards our hotel. As we drove through the streets I was overwhelmed by how different everything looked as I stared out the window compared to anything I had seen before. As we got closer to our destination, every corner of the street seemed alive with people going about their daily lives; colourfully dressed business people mixed with lots of simple suits walking down to start commuting on what we assumed were crowded subways, young couples sharing an ice cream cone while sitting on steps outside old temples and children playing tag in parks that seemed like they hadn't changed since ancient times. The sights were thrilling and nothing could dampen my enthusiasm as we arrived at our hotel situated right in the heart of downtown Tokyo.

The building was tall and sleek with modern glass windows that glistened in the early morning sunlight. We paid our driver, grabbed our bags and walked into the lobby.

The interior of the hotel was just as luxurious as its exterior and I felt a sense of awe come over me. The air inside was cool and pleasant, filled with the scent of fresh flowers that decorated every table top. The check in desk had two friendly receptionists behind it who greeted us with broad smiles, speaking to us in perfect English.

Jan stepped up to the desk and started giving us all our information before pulling out her credit card to pay for our stay. Our room was to be on the 11th floor which would overlook the bustling city streets below, we were promised. Jan finished signing all the paperwork and once everything was taken care of, we thanked the receptionist and grabbed our key cards before taking the elevator up to our room where Jan inserted her card into a slot allowing us access inside our home-away-from-home for the next few days.

A large king size bed was the feature of the room. It had four wooden posts around it and was about waist height off the floor. We placed our bags down and checked out the bathroom. The bathroom was decorated in a modern, minimalist style with a large shower head and a deep bathtub that sat against the wall. I couldn't help but feel a tingle of excitement run through my body as I imagined all the things Jan and I could get up to in that tub.

Jan caught my expression and smirked at me before playfully slapping my arm. 'Behave yourself,' she teased.

I grinned back at her before heading back to the room to start unpacking our bags and settling into the room. The view from the window was breathtaking and we spent some time admiring the city before deciding to explore it for ourselves. We planned to visit the famous fish market, try some of the local cuisine and maybe even visit a few of the city's famous bars.

As we stepped out onto the street, I felt a sense of excitement and anticipation wash over me. This was going to be an adventure of a lifetime, and I couldn't wait to experience it all with Jan by my side.

We spent the next few hours exploring the bustling city. Everywhere we turned there was something new and different to see. People we met along the way were incredibly friendly and helpful. After lunch we made our way back to the hotel to catch a nap and then freshen up before heading out for the evening.

I woke up after about two hours, feeling fresh and rested. The bed, comfortable and warm like a good hug. Jan had her arm draped over me as she spooned me from behind. I felt stirrings in my panties, panties that I had forgotten I was wearing. I woke her gently and told her the time.

'Mmm. Time to shower and then go explore some more,' she told me.

We both got out of bed and made our way into the shower. It was big enough to fit us both comfortably and would probably fit another person.

The water felt amazing on my skin, soothing whatever fatigue remained from the long journey. Jan started caressing my body, gradually moving lower until she reached my ass. I gasped as her fingers circled around it, teasing and playing with me until I was completely aroused. She then moved down to my ankles and legs, gently massaging them and then back up to my neck where her lips found mine in a passionate kiss. We stayed like that for what seemed like eternity before finally breaking away. Jan grabbed the soap from its holder and washed me slowly, taking her time as she explored each part of my body with her hands and mouth. I dropped my hand to her super wet pussy and began to rub her clit in slow circles, feeling her body tense up in pleasure. She moaned softly as I continued to pleasure her, her hips moving in time with my fingers. I pushed two fingers inside of her, feeling her walls clench around me as she cried out in ecstasy. The water continued to cascade over us as we lost ourselves in each other, our bodies pressed together despite all the space of the shower. Jan eventually reached orgasm and her legs shook in delight as I pulled my fingers out and kissed her once more, feeling the softness of her lips. We shared one last passionate embrace before turning around to get ready for our evening adventure.

It was nice to repay the favour that Jan had given me on the plane. My boner struggled to go down as I pulled my panties back on and we got dressed in silence. I could tell Jan was still enjoying the sensations of the shower orgasm.

Once ready we headed out to a nearby temple. The temple was an awe-inspiring sight. Its intricate carvings and statues mixed with regular temple goers going about their business. We spent a good hour exploring the grounds, admiring the craftsmanship of its builders as well as taking in the peaceful atmosphere that surrounded us.

As we left we noticed a few restaurants nearby and decided to try one for dinner. The restaurant was small and cosy, with low lighting and traditional Japanese decor. We were greeted with smiles and bows as we were pointed to two seats at the counter. Jan and I sat down, taking in our surroundings. The menu was entirely in Japanese, but luckily the waiter was able to speak English and helped us with our order. We decided to try a few different dishes, wanting to experience as much of the local cuisine as possible. As we waited for our food, we sipped on sake and talked about our day so far.

The food arrived and we dug in, savouring the unique flavours and textures. We tried everything from sushi to tempura to yakitori, enjoying each dish more than the last. The atmosphere was intimate and romantic, and we found ourselves lost in each other's company once again. We talked and laughed, enjoying the moment and each other's presence.

After dinner, we decided to just stroll through the streets back to our hotel. We walked through the crowded streets, still bustling at the late hour, taking in the sights.

Nearby to the hotel Jan spotted a small adult shop tucked away in a back alley. She grabbed my hand without a word and dragged me inside, unable to contain her excitement at seeing such unique items available for purchase.

The proprietor, a well presented middle-aged lady, was more than happy to show us around, explaining with great enthusiasm the various costumes and other items available on display. I was taken aback by the sheer variety of things on offer - from complete bondage sets to leather dominatrix costumes, there was something for everyone's taste.

Jan wasted no time in trying on several outfits before settling down on an outfit that she liked best - a black leather catsuit with matching accessories that showcased her curves perfectly. She looked absolutely stunning.

'Now it's your turn,' she excitedly exclaimed.

The shop was like a TARDIS and had rows and rows of different costumes, panties, harnesses, toys and much more. It was hard not to get overwhelmed as I ran my hands over different types of fabrics. It was also very hard in my panties as I browsed through the different types of costumes. The shop owner hovered nearby as we looked around some more. We were the only people in the shop so it felt like we were getting a VIP treatment.

After a few more moments of browsing, Jan eventually decided that I should go for a classic school girl costume: knee high socks; a very short skirt; black slightly, heeled shoes; and a white shirt. It even included a red little tie. Stereotypical would have been the best way to describe it. The shop owner was very helpful in getting me fitted properly and soon I had a complete outfit on. I felt embarrassed as she dragged me by the hand and paraded me out to Jan. She beamed with happiness as she saw me in the costume, her eyes filled with desire. The panties that came with the costume were white and pretty plain, but looked amazing under my skirt. My boner pressed out the front and tented my skirt.

'Won't do. Won't do,' said the owner as she dashed away.

I thought she was about to call the police for indecent exposure. Just as I was about to head back to change, she came back with a small box in her hand and with another bow handed it to Jan.

'For you,' she simply said.

Jan opened the box and inside was a glint of metal. A chastity cage. Jan's eyes widened in surprise as she looked from the cage to me and back again. I felt my cheeks flush deep with embarrassment and arousal. We had never spoken about this before. But now that she held it before her, it felt completely natural. Having never tried one before and sporting a raging boner I knew I wouldn't get it in my current state, but I was intrigued by the possibilities. Jan smirked and turned back to the shop owner.

'Thank you very much. We'll take it,' she said. 'Go change Tiger!'

While I changed I could hear laughter outside between Jan and the owner. Jan had already bagged her purchases when I finally came out after spending a few minutes struggling to calm down enough to stuff my erection into my panties and jeans. I handed over the costume, neatly folded, and the owner smiled and bowed at me before bagging it too.

We walked back to the hotel in silence, my heart racing with anticipation. As we rode up the elevator, Jan whispered in my ear.

'Time for us to put it on you,' she breathed, speaking about the chastity cage. 'Show me how much you trust me,' she said, her voice low and seductive.

I nodded, feeling my body tremble with excitement. We rushed to the room and fumbled with the door before closing it behind us. Jan led me to the bed and instructed me to lie down. She then took out the cage and began putting it on me. Only one problem. I was far too aroused to get it on.

Jan smiled and grabbed my balls, squeezing them hard. I gasped in pleasure and surprise as she kept up the pressure. Gradually, the erection subsided enough until finally the cage was able to fit snugly around me. I felt like a completely different person now that I was caged. My breathing was ragged; my heart raced with anticipation of what would come next.

Jan grinned knowingly down at me as she snapped the padlock shut on the cage, securing it tightly around my body.

'Now,' she said in a low voice, 'I think it's time for your punishment.'