'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 on 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 tie 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.
Without warning, 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 kneaded my ass and ran her fingers up the skirt until the elastic band of my panties rested against her nails. I felt her fingertips, cool on my skin, dig into the back of my thighs as she pulled down the panties until they were bunched around my ankles. She then grabbed a handful of hair and pulled me so that 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 firm 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.
My eyes widened as I peered down at her waist, my gaze lingering on the strapon that was secured there. Its size was daunting and I felt fear and desire in my stomach as she tightened her grip on it, a silent promise of what was to come.
The imposing red phallus stared back at me as she held it, its smooth surface glistening in the dim light. If I were to guess, I would have guessed it was nine inches long an erection of epic proportions that stood in stark contrast to her tight black catsuit. I looked on with envy at its size, knowing that even my own sizable cock had nothing on it.
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 clicked away as she expertly moved around me, angling for the perfect picture. I closed my eyes and felt her warm hands cup my manhood, hot through the metal of the cage that held it. Her finger trailed across my burning cheeks, grazing against my reddened skin.
'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 followed her command, feeling my anticipation rise as her warm and wet hands pressed against me. I heard the slick sound of lube pouring onto my skin, and a gasp escaped my lips as I felt her slowly insert two fingers inside me. Jan’s steady thrusts had me arching my back in pleasure, allowing her to stretch me wider with each movement of her expert hands.
'You're so tight,' she whispered before sliding up another finger and pushing harder.