Little Bo Peep - The Third Outing

Despite telling ourselves we were organised people, the last minute scramble before the taxi arrived was happening. Passport locations were being triple checked and bags were being checked that they were secured tightly.

'I think that is everything,' I said to Jan.

'Wallets,' she asked.

'Check,' I replied.

'OK. Brilliant. Now time to wait for the taxi,' she gleefully exclaimed.

Two and a half weeks in Japan was finally here. All we had to do now was endure the flight we had to take and we'd be soon living it up in Tokyo for our first few nights in the country. What I didn't know was all of the different dirty things that Jan had in store for me.

Tucked away in her bag was a new toy that she was dying to try on me. But tucked away in her handbag was another surprise.

As we sat in the taxi, Jan fidgeted and slid her hand into her handbag. I could tell she was itching to show me.

From her bag she pulled out a small black box. About the size of a small envelope. She had a mischievous grin on her face as she handed it to me.

'What's this?' I asked, my curiosity piqued.

'Open it and see,' she replied, her eyes dancing with excitement. With a quick glance at the driver, not sure if this was something for my eyes only or if it were something innocent enough. I eagerly undid the red ribbon keeping the box closed and opened the box to reveal a sleek black object.

'Is that a?', I queried, looking over to Jan.

'Yes, it is exactly what you think it is.' She smirked.

Sat inside the box was a black butt plug. Not too big, but not what you would consider "small".

'I thought you might like to wear it for the flight,' she teased.

I couldn't believe what Jan had in store for me. Wearing that on the flight would certainly make for an interesting experience. I had heard of people doing things like this before but never thought I would actually be one of them. As I held the black butt plug, I couldn't help but feel a rush of excitement and a tingle between my legs.

I looked over at Jan, who was grinning from ear to ear. She knew exactly what she was doing to me, and I could tell that she was getting turned on just thinking about it.

'So, what do you say?' she asked, her voice low and sultry. 'Are you game?'

I took a deep breath and looked down at the butt plug in my hand. It was sleek and smooth, and I could tell that it was well-made. With one last glance at the driver who had their eyes firmly on the road I nodded.

'Great. You can pop to the bathroom before we go through security,' she excitedly proclaimed.

'WHAT?!' I whispered. 'I was expecting you to hold on to it until we were on the plane.' I began to sweat slightly but knew it was a losing battle.

'Where would the fun in that be?' she retorted. 'I want you squirming even more than you are now before we get in the air. Oh, and I nearly forgot. I have something else for you too.'

Again, from her bag she produced a little paper parcel. I knew what was wrapped inside. A pair of lace panties.

My heart raced. I subtly took the paper package from her hand and unwrapped it, revealing the delicate lace panties inside. They were a deep blue colour, a perfect match for the black butt plug, and despite my worries I couldn't wait to try them on. A few agonising minutes later the taxi pulled up to the airport, I made a quick job of hiding the packages in my bag. What would be harder to conceal was my raging boner now pushing against the front of my jeans.

Once checked-in I was ordered to dash to the bathroom, my heart pounding with excitement. I locked myself in a stall, quickly slipped off my underwear, and after adding some lube from the sachet included in the box, I inserted the butt plug. It was a tight fit, but as it settled into place, I felt a wave of pleasure wash over me. I quickly put on the lacy panties, admiring how they hugged me but looking ridiculous with my cock tenting in front of me.

As I walked out of the bathroom, Jan was waiting for me with a wicked grin on her face.

'Ready?' she asked, her voice breaking slightly. I nodded, feeling a thrill of excitement run through me.

The line for security was long. But we edged our way forward. Jan had her head firmly planted in her phone as we moved along. When I was next to be called forward I felt a sudden vibration in my ass. The butt plug had come to life.

I gasped and looked around, trying to be discreet while I noticed everyone was staring at me. I was sure they all knew what was going on. Maybe they could hear the buzzing of the butt plug. I felt a bead of sweat drizzle down my forehead as I forced my legs to carry me to the metal detector.

'I'll be right behind you,' she said, her voice low and seductive, with a strong emphasis on "behind". My heart felt like it was going to explode. I edged my way through, resigned that I was going to beep, not even the smallest bit worried that I would have to hold the butt plug inside me for the next few hours. Without trying to make a scene I passed through and beeped.

'Shit,' I murmured. In all my excitement I hadn't taken off my belt. Here I was hoping that I would be left though. The female security person took one look at me and ushered me to the side. I went over to her and she passed her wand over me a few times. I mentioned I had forgotten my belt and after a few passes of the wand she waved me through. I nearly fainted.

Once I was through security Jan was right there with me, her hand sliding along the back of my neck.

'That was a fun little game, wasn't it,' she giggled.

I nearly told her there and then that I didn't find it funny when I noticed how my cock was throbbing. The excitement and thrill of being potentially caught but managing to get away with it was clearly having an impact on me. I remained silent.

We made our way to the bar. Sat down and both ordered pints. When they were served to us I felt another strong wave of vibration pass through me.

'Here comes the next part,' she said, her voice thick with laughter. I squirmed in my seat, looking around at other people sitting nearby, my face beet red. Again, I was sure that everyone was looking at me. But nobody was paying any attention. I looked over at Jan and noticed her devilish smile on her face. 'Oh so you like that huh,' she teased, noticing me shifting in my seat. The butt plug was still again until I took my first sip where it was turned up to full, and I could feel a strong tingle in my balls. I thought I might actually explode.

'I can really tell,' she whispered in my ear.

'I think you are going to really enjoy this flight, and maybe even our first night in Tokyo,' she said simply. 'But you're going to have to be a good boy for me, aren't you?'

I took a deep breath and nodded. 'Yes Miss.'

She couldn't contain her excitement. Her cheeks were blushed and a smile cracked across her face. I had finally acknowledged to myself and her what we had become. I revelled in the moment, taking it all in as we each sipped our pints. The atmosphere was full of hints at what we would do in Japan. It was turning into less sightseeing as time passed. She teased me mercilessly with her words, nearly pushing me to the brink on two occasions.

My panties were tight and sensually rubbing against my cock. Her hand rested near my crotch as another, different this time, vibration wave went through me. Her phone the tool in this torture as she ran her finger up and down the screen. Each pass adjusting the wave of pleasure I felt inside me.

I let out a quiet whimper as I felt my cock twitch in my panties. Jan looked at me, a grin on her face.

'Now now. Keep it together,' she teased. 'I bet you're wishing more people were here so they could see your little secret aren't you?'

I couldn't put up much of a fight. I tried to but she had a strong hold on me. She knew what I wanted and she was going to give it to me. I nodded.

'I want everyone to see you for the little slut that you are.'

'Yes Miss,' I replied quickly, knowing how much of an impact that was starting to have on her. Her cheeks were flush.

I leaned in and brushed her ear as I whispered. 'I can't wait for you to have your way with me. I want to pleasure you until you are the one begging ME to stop.'

With that the vibrations, which had been sitting on a low level, ended.

'I think our flight is boarding,' she said, looking at the screen behind the bar.

I moaned in frustration. Louder than I anticipated which sent a glance from the girl behind the bar my way.

'Come on,' Jan said, holding her hand out for me. 'We can't be late.'

With weak legs, I pushed myself off the bar stool, my cock twitching as it did so. She looked down at my crotch and smiled.

Giving me a playful slap on the ass. Her hand lingering to give my cheeks a slap. 'This is going to be so much fun for us both in the next few days.'

I nodded like a little school girl as we made our way to the gate. I was barely able to take full steps without the buttplug firing another wave of pleasure through me. My cock so desperately needed to be let free and touched. I felt like I was going to explode.

'The next part,' Jan began, 'is going to be a little more difficult to manage isn't it? But we have a few hours to practise.'

I agreed. My head was swimming with the possibilities. We reached the plane to find most people had already boarded. Our tickets were checked and then double checked.

'One moment,' said the very attractive lady from the cabin crew.

'Unfortunately due to an aircraft change your seats are no longer available. When I say unfortunately,' she paused.

'Better if I show you. Right this way,' she ushered.

We followed her to the left where the seats were spaced like you see in films. Seats that look more like futuristic pods.

'Here you are,' she said. '4A and 4C. Sorry if I scared you thinking you wouldn't have seats. Your husband here looks white as a ghost. But quite the upgrade, they should have told you at the gate so it wasn't such a surprise.''

'Oh no, don't worry. He's just a little nervous about flying. It's been a while. Nothing a drink won't sort,' covered Jan.

'I'll be right over with some champagne,' the lady said. 'I'm Casey, by the way. If there is anything you need during the flight, I'm just a call bell away.' She smiled at me and winked.

'Thank you very much,' Jan smiled.

We were seated in the front section of the cabin. Just in front of the cockpit. Settling down I looked around my seat and saw a menu, a screen with the company logo on it and a little goodie bag with headphones and some other bits.

'One champagne for this gentleman and one for the lady,'Casey said as she returned and sat it on the table in front of us.

'I'll be back in twenty to take your food order. Take your time to read the menu and passenger information booklet,' She looked at me.

'Will do,' I blurted out as another vibration rushed from the butt plug.

'I'm really sorry about that, Casey,' Jan told her. 'He's normally not like this. He doesn't travel much. It's just he's been looking forward to this for so long and is clearly overly excited.'

'It's fine Miss. No sweat. Enjoy.' She gave me a pointed look. 'I'll be back for that food order in a few minutes. If you need anything, just call.'

'Thank you,' Jan said again. I tried to look as natural as possible.

I nearly buried my head in my hands. Jan meanwhile was chuckling away to herself, clearly enjoying her game.

'I think we should have some fun with this,' she said. I looked up at her as another wave of vibrations went through me. I was trying to fight it.I was trying to hold back from making a spectacle of myself. What if Casey came back and caught me in the middle of an orgasm. Would she turn me over to the police? I knew that it was very possible in this day and age.. My face was beet red as I tried to hold on. I leant back in my seat. Letting out a loud breath as the vibrations stopped. One last burst was building up in me. I was so close to cumming but I knew I had to hold on for just a little bit longer.

'You're being such a good boy,' Jan said, almost in a whisper. 'I'm proud of you and I think I'm going to reward you.'

I sat up, my cock aching to be touched. Aching to be released. Ready for anything. Anything at all. Jan smiled and then reached over to my seat. Her hand slipped in between the two seats towards me. She reached for my cock and began to dance her fingers on my bulge. I shuddered, the movements sending waves through me. Pulsating sensations through my body.

I reached out with both hands. Grabbing her arm. 'Stop. I'll... I'll.. I'll cum if you continue,' I said in a low voice.

'Maybe that is exactly what I want,' she whispered in return.

Looking around I could see there were only two other people in this area. A middle aged looking man, clearly on his way to Japan for work and Casey milling away at the bar.

I felt Jan's fingers moving around my bulge again while at the same time sending the vibrations into overdrive. The sensation was so intense that I could barely concentrate and felt like I was about to pass out. I had held on as long as I could, but the pleasure was too much and it all became too overwhelming for me.

'Cum for me Tiger,' Jan said in hushed tones, seeing me struggle.'Let it all out.'

And with that my body spasmed and I let out a loud moan as a wave of pleasure surged through me as the butt plug rocked up to full power. Jan watched with a satisfied smile, having teased me right up to the very edge of climax. Finally, when my body stopped shaking and I regained control of myself, we looked at each other with knowing smiles. We both knew what had just happened, and nobody else had noticed -- not even Casey who was taking the food order of the man in the other row. Noticing that she would soon head our way, with my panties soaked with cum I grabbed the menu, covered my lap and decided on the first thing I saw.

'I'll have the steak,' I stammered when Casey eventually came over.

Telling me to hang on to the menu she made her way back to the bar after taking Jan's order, leaving me to my thoughts. The plane began to move.

'I hope she didn't notice anything,' I said anxiously. 'If she had, she might have asked what we were doing.'

'Maybe next time,' Jan said.

'I'm not sure I could handle that!' I replied. My thoughts were racing. I had cum so much and enjoyed every last minute of it. I think I was starting to like this whole thing.

The plane began its roll down the runway about ten minutes later. I leant back in my chair eagerly awaiting the first moment when I could go to the bathroom to clean up.

When the seatbelt sign finally switched off I shot out to the bathroom. Jan grabbed my wrist.

'I think you can take your little surprise out. You had enough fun for now,' she fiendishly said. 'And here, take this.' She presented me with another paper wrapped parcel.

Another pair of panties. I waddled to the toilet, making my way past Casey who was up and prepping some snacks. I quickly entered the toilet and locked the door. Sitting down I noticed my cum had miraculously not seeped through my jeans. I took off my jeans slowly so as not to drop an cum on them. Thankfully it had mostly dried. My panties soon followed my jeans. I rinsed them and dried them as best I could in the spacious first class bathroom. In my hurry I hadn't noticed the shower in the corner. Soaps and towels were standing on a shelf nearby. I quickly threw off my t-shirt and removed the butt plug before stepping into the shower.

The warm shower felt like a blessing. I closed my eyes and let the warmth wash over me. The gentle pulsations from the butt plug were gone, but I still felt a tingle in my body from the intense waves of pleasure that Jan had teased out of me. Taking some soap, I scrubbed my body clean feeling refreshed and ready for whatever the rest of this journey had in store. I dried off and opened the parcel to reveal the fabric it held. I put on the new pair of panties - a bright pink patterned boyshort. I enjoyed the feeling of them in place while I admired myself in the mirror briefly before putting my clothes back on. I carefully hid the buttplug in my back pocket and tried my best to wrap the still damp panties in the wrapping of the new ones.

I took a deep breath and walked out of the bathroom, trying my best not to notice Casey who was offering a fresh drink to the man sitting in the other row. She nodded in my direction as I made it back to my seat. I quickly set to hiding the damp panties in the pocket under the TV screen and quickly stashed the butt plug in my flight bag before sighing and leaning back into my seat. Jan, who had already finished her snack, smiled at me knowingly, although we said nothing more.

As the plane flew further away towards our destination, I looked out of the window - becoming suddenly spiritual and marvelling at the beauty of the world below - feeling content and excited for what else this the rest of this flight and this journey would bring.