Little Bo Peep - The Seventh Outing

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Jan and Tiger get passionate. Tiger gets his dessert.
3.3k words
4.64
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Part 7 of the 8 part series

Updated 11/21/2023
Created 05/15/2020
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From Osaka, we made our way to Kyoto and from there continued our way south towards Hiroshima over the next few days. Along the way we did much of the same as we had done in every other place so far- sightsee, eat, drink and have Jan tease or fuck me within an inch of my life. Each night she would tease me while I remained locked in my cage and some nights not allowing me to cum at all.

It had been months since I had properly been inside Jan during sex. This didn't upset me but I would have liked to feel what it was like inside here.

After a day in the countryside, the journey to the city was quick and exciting. We'd heard so much about the place and what it had been through, you could feel the history in the air. As we reached Hiroshima I felt a great anticipation of finally being able to experience this place.

We stayed at a cosy little guesthouse right on the banks of the Ota River. From here we had an incredible view of downtown Hiroshima which looked stunning both day and night. During the day, Jan and I explored many of the famous sights like the Hiroshima Peace Memorial Park, A-bomb Dome and Genbaku Dome as well as other tourist attractions across the city.

On our last day before heading back towards Tokyo, we decided to check out one of the recommendations from Suki. One of her favourite restaurants, a tiny little sushi place she said only locals knew about. The sushi was delicious and served with such hospitality that Suki told me it didn't even compare to anything we would have experienced before in Tokyo or anywhere else. We feasted on fresh food and saki until we could eat no more.

We stumbled our way back to our guesthouse and quickly found ourselves kissing each other in drunken passion. I had not cum in two days and was aching for release. Only this time I wanted to cum inside Jan.

The heat of the city was keeping us warm and we had no need for covers once we had shed our clothes. The thin sheet on the bed feeling great against my skin. I had been teasing Jan ever since we had arrived in Hiroshima. "Being a brat" was what she had called it. I'd given her some of the best orgasms of her life so far this holiday but she was still denying me my release over the last few days. I knew I had to be careful otherwise she might just leave me locked in my cage until we got home. Just the thought of being denied for so long almost made me cum on the spot.

We had been kissing for what seemed like hours and I felt my body ache with desire. I could feel my cock throbbing against the metal of my cage. Jan could feel the cold metal against her body as she ground into me.

I rolled her onto her back and I lowered my head down to her nipples. The metal of the cage was cold against my skin as it rested against me.

'Are you going to let me cum today Mistress?' I asked while giving her erect nipples a lick.

'I'm not sure. I think I am enjoying making you wait. Perhaps I should make you wait longer,' she said, groaning at my tongue and my teeth playfully biting her nipples.

'You mean you might leave me locked up until we get back to Tokyo?'

'Yeeeaaah, I'm not sure. If you are good I'll think about letting you out,' she teased.

'Please Mistress,' I begged. 'Please, please let me cum inside you, so deep. It's been so long, please.'

My voice was needful, aching. 'Jan,' I continued. 'It feels like forever since I've been with you and been allowed to explode in your pussy. It feels like eternity'

My begging and pleading had Jan feeling both aroused and slightly annoyed. She'd been teasing me for days and wanted to make sure I knew it wasn't all about my pleasure. With a mischievous smirk, she sat up and quickly flipped me over onto his stomach, straddling my body so she was facing away from me.

'You've been so needy lately Tiger,' she said as she grabbed the mini-flogger that had been lying on the bedside table. 'I think you need to be taught a lesson in patience.'

She let the strands of the flogger slide across my backside, teasing me with what was to come. I begged and pleaded.

'No, mistress please. Please don't spank me, please mistress.' I tried to kiss her leg in a desperate attempt to convince her. 'I've been so good, I swear I have.'

I knew this was just driving her on. Knowing that my squirming and pleading was making her even wetter than before. I could feel her as she sat on my legs. The warmth radiating as she brought the flogger down across one of my cheeks. The sensation against my body was overwhelming. My cock throbbed in my cage, I was so close to cumming.

'You've been a bad boy, Tiger. So very bad.' Jan said as she continued to flog my as

'Please Mistress, I will be good. I'll be so good. I'll never be bad again. I promise Mistress.' Jan was hitting with ever increasing power now. My body shook with pure pleasure as I tried to keep in the scream.

I knew I was close but I fought it. Jan stopped suddenly and got off my legs. She sat me up in the bed and dangled the key in front of my face. She was torturing me.

'Say it again,' she demanded, 'tell me exactly what you want right now.'

I looked deep into her eyes and said, 'I want my cock unlocked from the cage, I want to be able to please you until I cum inside you Mistress. Please, let me make love to you.'

Jan smiled at me and took her time mulling over what I was asking as I panted like a puppy. She nodded slowly.

'Good boy,' she smirked as she leaned in closer and kissed me softly on the lips.

'Your wish is my command.' she said as she opened the lock on my cage, freeing me to do as I wanted.

'But first,' she said, grabbing my penis to hold me still. 'I want you to lick me. And take your time.'

It felt like a lifetime had passed since I had last been able to pleasure Jan with my cock, but that would have to wait. In the meantime I would have to rely on my tongue.

As she lay back on the bed I moved forward, gently kissing her. The taste of her wet pussy on my lips. I could feel her warmth emanating from her body. My tongue danced over her clit, wiling her to open up to my slow assault. Her legs were wide and she pushed them open as I bathed her in tiny, soft tongue strokes. The more I licked her clit the more wet she became. Reaching around her thigh she slipped two fingers into my mouth for me to suck before rubbing her nipples with them.

'Get your cock out of the cage,' she suddenly croaked. I grabbed the key and fumbled to get it open. I took my cock out the cage and it immediately began to grow. Jan took her hand and gripped my balls. It felt amazing. She teased and tugged at them, squeezing slightly as she did. I was soon at full mast and ready to be inside Jan.

'Mmmmm,' groaned Jan as she watched my cock. 'I keep forgetting how delicious your cock is.'

She grabbed me by the shoulders and forced me down onto the bed. Her body straddled mine, her legs pinning my thighs to the mattress beneath us. She hovered just above me, her breath hot on my face and her warmth radiating through my clothes. With a wicked grin, she slowly lowered herself down, inching closer until I could feel the slick wetness between her legs rubbing against my aching cock. As if she knew exactly what she was doing to me, she began grinding against me in circles, each movement agonisingly close to my cock slipping inside her.

She took my nipples in her hands and completely teased them, playing with them and pulling on them lightly until I was moaning in pleasure. Finally, she reached forward and gently took my cock in her right hand. Her fingers were cool and firm as they closed around me. She breathed out slowly as she tilted her hips forward and impaled her tight pussy on me.

The sensation of being inside Jan was overwhelming. She rode me with a ferocity that I had never experienced before. Every thrust from her was driving me closer to the edge.

I dropped my head back and groaned in sheer bliss as she moved her hips in circles against me. The warmth of her body was enthralling, and with each thrust I could feel myself filling her completely. My desire for her consumed me. She had my hands pinned down as she contined to use my cock for her pleasure.

'Don't cum yet,' she panted. 'I... am nearly there.'

Sweat covered our bodies as she rode me with increasing speed. I could feel her squeezing my cock as her pussy tightened around me. She threw her head back and let out a scream as she came. My hips thrust in pained pleasure as she gripped me and the feeling of her cumming with me inside her sent me over the edge with her.

I could feel her juices running over my cock as I emptied myself into her, and as she collapsed on top of me I wept tears of sheer happiness. I turned my mouth to hers and kiss her as she continued to lay on top of me. She ran her hand down my face and traced her fingers down my body.

'I love you,' I said to her. 'I want you to know how much I love you.'

'I love you too,' she replied. Jan's eyes were shining with happiness and love. 'I'll always want you, you are my everything.'

She held my arms above my head tight as we both enjoyed this moment of bliss. But that moment of bliss soon came to an end when Jan sternly reminded me that I had not asked her permission to cum inside her. I knew then that I had lost myself in the moment and there would be punished for my actions. Jan held me tight, making sure that I couldn't move from the bed. She took a deep breath before speaking.

'What do you think I have in mind this time?' she questioned.

With many things I knew I didn't have to answer. That Jan would be decided for me, regardless of what I suggested.

'I think you want me to lie here and clean the mess I've made inside you,' I said, trying not to sound too hopeful.

Jan smiled and nodded her head slowly, confirming my answer. 'Bad boy, yes. How did you guess? Yes, that's exactly what I want you to do. I want you to lick my pussy clean of all your cum and  my juices.'

She pushed down on my arms as she repositioned herself. Her pussy hovered over my face. I could see some of my cum waiting to fall and tried to reach out with my tongue. Jan laughed at me.

'Who would have thought I'd turn you into a cum lover as well? Of all the depraved things I have made you do, this is the one I'd have least expected' she said.

With that she pressed down on my face so I could lick her clean. My licking and probing her with my tongue was slow this time. She reached down and took my cock in her hand and gently squeezed.

'You are so lucky I love you,' she said as she began to jerk me.

I looked up at her but she had her eyes closed and was clearly enjoying how I was using my tongue. I could feel more cum dripping onto my tongue every time I thought I had gotten it all. It was taking longer than I thought to get her clean between my attempts at licking her clit.  ut I knew better than to stop licking.

'Focus on my clit,' she said after a while before reaching down and grabbing a handful of my hair. This focused my attention in the right place and I began to lick her clit with more force. She slowly began to grind her pussy against my face as my tongue worked on her clit. She was getting close again. I could feel my face getting wetter and wetter again as she neared her second orgasm of the night.

'I am close to cumming again,' she moaned.

As I was a little preoccupied, I could only continue licking her as she rocked on my face.

'You are such a good boy.' Jan groaned deeply. Her voice was getting louder as she approached her orgasm. Her rocking didn't stop as my tongue began to tire. I began to breathe harder as I continued and felt her hand grab my hair even tighter still as she suddenly turned stiff before exhaling deeply and shuddering on my face.

She collapsed, propping herself up on the headboard as I caught my breath beneath her.

'Wow,' she sighed.

I murmured in agreement as she climbed off me and propped herself up on her elbow next to me. Smiling stupidly at her she brushed some hair out of my face and kissed me deeply. Our combined cocktail of juices still clearly on my tongue.

'Now,' she began and nodded at my fully hard cock 'What to do with him?'

She told me to play with myself as she got up from the bed. I was quick to obey and touched myself in slow long strokes while she rummaged around in a bag. When she returned she had the butt plug from the plane in her hand and a bottle of lube.

'Time we gave this another go,' she said happily.

I continued to play with my throbbing cock as she lubed up the butt plug. I was no longer a teenager so was surprised when she pressed it slowly into me that I began leaking pre-cum again. Could I cum twice in one night again?

The plug made me feel full. Jan sat back on her knees and grabbed her phone. She started the vibrations at a low level and watched me.

'I think I'll record this one. You look so good lying in a filthy sweaty mess with a plug up your ass as you play with your cock. If only our flight attendant friend, Casey could see you now.'

I groaned at the thought of being watched by more than just my beautiful wife.

'Then again,' pondered Jan, 'maybe she's awake right now.'

With that I watched as she video called Casey. Within a few rings a voice answered.

'Hello,' the voice inquired. 'Oh, hello Jan.'

'Casey. It is good to see you. Sorry for the early call. I know it's only the start of the day there and I hope you're not busy,' Jan continued, 'but I have something I want to share and I think you'll enjoy it.'

I groaned in embarrassment while I continued to jerk my cock as the phone camera was clearly turned on in my direction.

'Oh. Is that?...' said Casey, her voice clearly trailing off. A hint of shock in her voice.

'Yes, it is. My Tiger is playing himself and I thought I'd embarrass him. Wait one second.'

She moved closer and made me lift my legs so they were propped up on my chest. There was an audible gasp on the other end of the video call.

'Yes, that's the toy you caught him with on the flight,' explained Jan. 'I told him I was going to ring you and show you how much he turns into a little slut when we put him in chastity.'

I moaned a little and Casey gasped but at the same time laughed.

'Oh, yes,' she said, 'He looks good like that, doesn't he?'

I could see Jan showing her the butt plug. I moaned in frustration and Casey laughed again.

'Oh, good boy. I am a bit jealous, actually.' she said, 'When I caught you with it on the plane I knew exactly what you two were like.' She continued and then laughed at my predicament as I continued to play with myself. My cock was throbbing as my wife showed me off to Casey.

After a few minutes I was getting close to cumming again.'

Oh, yes,' Casey sounded concerned, 'he's close, isn't he?.'

'Notice he's starting to leak?' asked Jan.

She moved one of her hands down between her legs.

'Don't you wish you were here so you could play with him,' she asked Casey.

There was no response on the other side except for some shuffling sounds and the beginnings of moaning.

'Good girl Casey, play with us,' purred Jan watching the screen.

I could only imagine what was happening at the other side and shut my eyes. In my minds eye Casey was playing with herself as she watched me helplessly play with my cock while the butt plug buzzed away in my ass.

 

I was getting close. The vibrating plug, my wife with her hand between her legs and the sound of Casey moaning were becoming too much for me to contain.

'Oh, yes,' groaned Casey again and again, reduced to just those two words.

The sounds on the other end confirmed she was wet and playing with herself. I looked up at Jan and with a nod of her head had her permission for me to cum. I was about to explode.

'Cum for us, Tiger. Shoot your hot load for both of us. Casey I want you to cum too. Imagine if you were here and the fun we could have teasing him together,'she said.

Her hand was moving fast between her legs as she said this. That was too much to watch and as my eyes closed, my hand began to move faster and faster. As I approached my orgasm my body began to shake.

'Oh, yes,' moaned Casey again followed by her loud moan of release. 'OH. YES.'

My second orgasm of the night blasted across me as I let out a scream and exploded all over my hand and stomach. Jan also began to shake at the edge of the bed as her body contorted and she reached another orgasm.

Deep breating emanated from myself, Jan and Casey on the other side of the phone until the silence was broken.

'Wow,' was all that Casey said.

I switched off the plug and began to remove it. The plug came out with ease and my ass throbbed as it was emptied.

'WOW,' I heard from Casey again.

'That's just the start of it Casey,' maybe when we're back from our holiday I can share more of what I do to Tiger.

'Oh, yes. Fuck,' was all she said.

'Enjoy the rest of your day,' smirked Jan and hung up.

I put my feet down and stared at the ceiling.

I looked at Jan and asked, 'Did that just happen? Wow!'

Giggling, she nodded, climbed off the bed and headed to the shower.

'You coming or what?' she asked.

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