Little Bo Peep The Fifth Outing

'I think it's time for your punishment.'

My heart jumped when she said this. Here I was in a chastity cage while my wife was planning on punishing me on the first night of our holiday.

'Be a good boy and go get cleaned in the shower and put on your outfit,' she commanded.

I nodded and scurried off to the bathroom. I stripped down, noting with a mix of dread and arousal that I still had the chastity cage on. I got into the shower stall, making sure to douche my ass before soaping up with a lovely smelling body wash. I rinsed off, stepped out and my eyes caught the full-length mirror on the wall across from me. It was really something else to behold myself standing there in nothing but a chastity device, one which felt like it was fastened shut tighter than a drum.

With quick movements, I finished drying off and started to pull my new schoolgirl outfit that I had brought in with me.

The tight white panties were snug on my toned frame, their elasticity causing them to cling to my skin like a second layer. I followed it up with the knee-high socks, which hugged my calves tightly and felt as if they would never come off. I then pulled on the short skirt, letting it fall over my hips and onto my thighs before finally reaching for the bra and shirt.

The sensation of the fabric against my skin was electrifying, and I couldn't help but admire myself in the mirror as I buttoned up the crisp white shirt. The bra fit just right, accentuating my very modest pecs, making the suggestion that I had breasts. Albeit, the smallest breasts imaginable. Finishing off the look was the pair of black school shoes that gave me an extra inch or two in height. The last thing I did was tied my hair up into two ponytails that fell on either side of my head. When all was said and done, I had transformed from a humble man into a schoolgirl ready for punishment. I called out to Jan that I was ready.

'Close your eyes as you come out,' she demanded.

I did as I was told and felt my way out of the door. Through my eyelids. I could tell there was only one light on in the room. I felt Jan come close and felt her breath on my ear. I could feel her stare at me with a smirk on her face even though I couldn't see her.

'You look amazing,' she said in a light whisper. Without another word, she walked behind me and fastened a blindfold around my head, covering my vision completely.

'Put your hands out in front of you.' I complied, feeling slightly off balance as I waited for whatever punishment was coming next.

Suddenly, Jan pushed me over the edge of the bed so that my ass was in the air and my feet were just dangling off the side. She grabbed my wrists and secured them in cuffs, then I felt rope tying them down to the bedframe with what felt like leather cuffs before standing back to admire her work.

'Now stay still while I get what I need,' she told me.

I could hear Jan rummaging around and then finally returning to where I lay helplessly bound in anticipation of what was going to happen next.

WHACK.

Suddenly, a sharp sting ran across my ass and I couldn't help but yelp loudly in surprise. Jan had fetched a paddle, clearly one of her extra purchases earlier in the night, and was now spanking me. She kept going, making sure to target each cheek with equal attention and intensity. Pausing briefly between each strike of the paddle.

With every swat came an amplified warmth that spread through my ass cheeks and down my thighs. I lay there moaning in pleasure as Jan continued to bring the paddle down hard on my flesh until it was red and burning hot beneath her hand.

Finally, Jan paused for a moment before commanding me to get up on my hands and knees. To make sure I understood what she wanted, she held the paddle close against my face so that its leathery texture felt cold against my skin. As soon as I complied, she began spanking me with the paddle again whilst demanding that I count to ten out loud with each stroke of the paddle. The pain and pleasure became increasingly intense with each number that passed until finally reaching ten, at which point Jan stopped. She caressed my ass cheeks and flicked up the short skirt even further. I felt her fingers invading the waistband of my panties before pulling them down my legs. She then grabbed a hold of my long hair and pulled me so my head arched backwards. '

Should you be punished some more for cumming without asking on the plane?' she asked coldly. 'Then again. I did say you could, but I don't remember you asking.'

I gulped, realizing that I had completely forgotten to ask during our flight and now faced Jan's wrath. My heart pounded in my chest as I waited for her answer, knowing that whatever I said would turn her on even more either way. All I could do was whimper.

'Good girl,' she cooed.

Another strike across my ass cheeks drove me forward, but Jan kept a frim grip on my hair. I must have looked quite the sight. On my hands and knees in a schoolgirl outfit, cock caged and ass red. The bed shifted as I felt her climb up next to me.

WHACK.

'I think it's time for the next step of our night,' she proclaimed.

And with that, Jan gently removed the blindfold so I could see again. I turned my head towards her to see that she was wearing the super tight catsuit that hugged her curves in all the right places that we had bought in the sex shop earlier that night. It made her look so commanding and powerful. Looking down I saw, strapped to her waist, a much larger strapon than we had used before. It looked about nine inches long and thick. It was red and smooth. It stood in stark contrast to her catsuit. I looked at it and gauged that it was certainly bigger than my own cock. I gasped as I looked up at her, completely taken aback by how beautiful she looked in this outfit. Jan smiled down at me and caressed my hair one last time before standing up and moving to the end of the bed.

'First though,' she paused, 'I need to take some photos of you looking like the dirtiest schoolgirl around.'

Her phone snapped a few times as she got a few different angles. At one point she cupped my balls in the cage while getting a close up of my red ass.

'Look at me,' she ordered after a while.

I looked over my shoulder as she pointed the camera at me and was full of embarrassment. Hopefully those photos never saw the light of day.

Putting down the phone she went to the desk and grabbed a bottle of lube.

'Eyes forward,' she demanded this time.

I obeyed, looking forward as I heard her pour some of the lube on my ass crack. Jan then started to work in two fingers, slowly stretching me open with each stroke of her hands.

'You're so tight,' she whispered before sliding up another finger and pushing harder.

I let out a low moan in pleasure as she worked me open. She was relishing this as much as I was. Eventually, I felt her strapon prodding gently at my entrance. She moved it around in circles, gently opening me up to the size of it and then began to slide it in and out of me with increasing depth on each pass.

Jan moved with a fiercer intensity as she ground her crotch against me. Her hot breath overwhelmed my senses, sending shivers down my spine as she bent over my back and whispered dirty promises as her thrusts increased in speed and strength. The loud slapping sound of the leather catsuit against my skin echoed off the walls as Jan continued to fuck me harder and deeper, both of us getting pleasure out of this. Every thrust was met with a moan of pleasure from us both as we moved together in perfect harmony. My back was arched and my hands held onto the ropes extending from the cuffs that remained firmly attached to the bed posts.

Despite my cage, pressing hard against my swollen cock, I felt myself getting close to the edge as Jan cried out and reached her climax. I could feel her convulsing as it sent wave after wave of pleasure through my body as she trembled.

I felt my orgasm rise up and it was all I could do to hold it back. Sensing my struggle, Jan pressed down hard on my back with her hands as she continued to thrust into me.

'Please mistress... please may I cum,' I gasped.

She was no longer whispering but shouted.

'Yes, Tiger. Let go. Cum with your mistress' cock deep in your ass,' as she continued to pound deep into me. I didn't need much but that's all it took, as if a dam had broken inside of me I felt myself hurtling over the edge of an intense orgasm. Jan kept hammering away at me as cum seeped from my caged cock and onto the bed. I let out a deep guttural moan of pleasure as white light exploded behind my eyelids as I came hard and strong, feeling every wave crash through me until it subsided.

Jan slowed while pressed up inside me and pulled out one last time before collapsing beside me, exhausted and satisfied from our night together. She held me close and for a moment we just lay there in silence, both panting from intense orgasms. My ass contracted and pulsed as it still waved in the air. Jan lay beside me and stared at me with intense love and desire.

'I love you Tiger,' she said.

I responded with a shaky breath, 'You know that feeling is mutual. I love you'

Jan unbuckled my hands and let me free.

'Now,' she said, getting up from the bed and looking at the cum on the sheets, 'I think it's time for you to clean this mess up.'

She was still horny. Despite all that session I could tell she wasn't done yet.

I obliged and crawled down the bed, taking one last look at her before bending down licking up my cum off of the sheets. There was a puddle that I was surprised I had produced. Jan watched with pleasure as I cleaned and grabbed her phone to take more pictures of me from all sides, making sure that this night would never be forgotten.

Never in a million years would I think I would be on my hands and knees dressed as a schoolgirl while my wife and now mistress was ordering me to lick up my cum.

When I was done, Jan began to slide out of her catsuit and dropped it to the floor. Climbing back onto the bed she laid back on with her legs spread and commanded me, 'Tiger, get licking.'

I didn't need to be told twice. I crawled up until my face was between her legs and started running my tongue over her delicate flesh.

A heady combination of Jan's honeyed lubrication and my own salty cum created an amazing cocktail on my tongue. I licked at every inch of her pussy, from core to edges, with slow, savoring sweeps of my tongue. I paused at her clit, teasing it with long strokes as she quivered and moaned beneath me. When I finally sucked it into my mouth, Jan let out a gasp that echoed through the room as I worked her to a crashing release.

She was sensitive from the early pounding of my ass but continued to encourage me to continue. I took my time but it wasn't long before Jan had her second orgasm of the night. I licked up all that I could before being ordered to stop.

'Enough. Enough,' she shuddered. 'Thank you.'

I sat up on my haunches. Still dressed like a slutty little schoolgirl as I watched her close her eyes in pleasure. When she opened them again she smiled and looked at me.

'You're a mess,' she giggled. 'Come, let us get cleaned up.'

'Lead the way mistress,' I said, motioning to the bathroom.

Jan hopped in the shower as I shed my sweaty clothes. The skirt was the last thing to drop to the floor in a delicate bundle.

I watched her in the shower for a moment.

'I need to pee,' she quickly said.

I laughed, surprising even myself and said, 'Go ahead. As long as you let me watch.'

Jan turned and winked at me before letting the warm water cascade over her body as she slowly squatted down and peed in the shower.

'Um, Jan. Should I take off the cage while I shower?' I questioned.

Laughing. She agreed. I hopped out to fetch the key that sat on top of the desk in the room. When I came back in I put on a show unlocking the cage. Jan watched with amusement as I carefully removed the cage. Giggling as I groaned when it fully came off. I couldn't help but feel a sense of relief as the tight metal contraption was finally removed from my body.

The feeling of warmth between us was electric as I hopped in and we both enjoyed this new experience together. We washed each other from head to toe, enjoying every minute of it until we were done.

'I love you Tiger,' she said again, with a smile on her face.

We continued to shower together, washing away the sweat and the remnants of our passion. The warm water felt invigorating and I couldn't help but feel grateful for this moment of intimacy with my wife.

As we got out of the shower, Jan handed me a towel and motioned for me to dry off. I quickly dried myself off before wrapping the towel around my waist.

Jan smiled at me, her eyes filled with love and desire. 'Tonight was amazing,' she said, her voice filled with emotion. 'I never knew I had it in me.'

I smiled back at her, feeling a sense of satisfaction wash over me. 'Nor I, I'm very glad we both discovered this side of ourselves,' I said, my voice filled with truth and humor.

Jan laughed before wrapping her arms around me.

'You're amazing,' she whispered, her lips pressed against mine in a long lingering kiss on the lips.

We returned to the room and flopped down on the bed. There was no need for clothes tonight. Tiredness and a complete sense of satisfaction rolled over the two of us as sleep quickly caught up with us.