Swiss Miss Sissy, Chapter 15a

By Bambi

Chapter 15: Past indiscretions. Cheryl spends the last day with Miss Rosenberg.

My time in the penalty box passed in darkness, since they kept me blindfolded for most of the duration. I once heard that keeping prisoners blindfolded is a simple but effective method to intimidate them, as it messed with their sense of time. I can confirm that is true. As I stared into the void, my other senses screaming as Mistress worked her wicked art on me, I had no idea how long I had been there already and how much more I had to endure. She had said she would keep me in the penalty box for six hours, and always seemed to honour her word, but I was never certain whether hours had passed, or mere minutes. Especially not when a mixture of exhilarating pain and merciless pleasure merged together into a intoxicating delirium that clouded whatever judgement I had left.

Due to that dreamlike state I cannot recall everything they put me through, but I remember certain events with a modicum of certainty.

I'm pretty sure they didn't bother with putting me in a special bondage outfit, but just kept me in the frilly pink outfit and heels I was wearing as they bound me to some contraption. Mistress stood behind me as her hands slowly stroked my breasts while she whispered in my ear. Threats and wicked promises she spoke as she kissed my neck and bit my earlobe. She told me about the various delightful torments she would subject me to, but never in detail. Just enough for me to become utterly terrified as my mind started to imagine what she'd do to me, making me beg and plead for mercy. She'd laugh viciously as I she heard the gag smother the words in my mouth.

Bernadette and Jeanne were present too. I occasionally heard someone laugh that I'm sure was not Mistress or felt more than one pair of hands on my body. At one point Mistress said she was taking a break. As her heels moved towards the door and exited the penalty box, I slumped in my bonds and gave an exhausted sigh, thinking I had a brief moment of rest. But suddenly I heard a chuckle right behind me and everything continued, just as viciously as before.

I remember being suspended from the ceiling. They fitted some harness around me, then put loose chains around my wrists and ankles. Something clicked as it was connected to the harness on the back, and I heard the whirring of a small motor. Then I felt the pull at my back as a chain tugged at my harness and dragged me upwards. I squealed into my gag and kicked my legs furiously as I tilted forward, my heels and soles scraping the floor without finding traction. Then I just felt air beneath me as the motor hoisted me up even further and I hung horizontally.

The chains on my ankles and wrists jingled as I struggled. I don't know what I wanted to achieve as I was dangling there from the ceiling, but for once my bonds were slack. I had freedom to move arms and legs. I started to fight, grunting angrily into my gag as I pulled on my bonds. Fear feeding a reckless fury that made me feel I could tear myself free.

I could force my hands just almost in front of me before the chain that connected my wrists to the back of my harness came under tension. I kicked and shook my legs that were connected to the floor somewhere. I swear I would have kicked Mistress if she was close enough!

I heard Mistress laugh as I struggled and squirmed. 

“Would you look at that! Looks like our naughty sissy has some fight left in her,” she said in an amused tone. “My, you are so delectable when you are angry...”

Another engine started whirring, and clicking was audible as a chain started to move. But it was not the chain I was suspended on. Dismayed I realized tension was increasing on my wrists and ankles.

Clack-clack-clack-clack I heard as my hands were pulled behind me towards the ring on my back. My legs were pulled to the floor, down and to the sides until they were completely stretched. Furiously I shook my head despite my tight collar, as my arms and legs were now fully immobilized, allowing only a few inches of movement.

Mistress’ heels clicked behind me, and she took up position. I grunted as she pushed her strapon against my sissy-hole. My plug had been removed earlier and now the tip of the penetrator applied pressure against my sphincter. I grunted again. No longer furiously, but out of desperate fright.

“Oh come now, my dear. Don't give up just yet. I expect you to put up a bit of a fight,” Mistress spoke. “Here, let me make it easier for you.”

The engine whirred again and I heard the chain go clack-clack-clack. My bonds went slack and I could move hands and legs, albeit less than before.

I felt Mistress push harder against my sissy-hole. “There you go. Now then, give it your best shot.”

“Humpfh!” I shouted as my fury returned. I struggled in my bonds. I could move my hands up to my sides, shaking them as if I could find grip on the air and crawl away from Mistress' penetrator. I tugged my legs, tried to kick, but the room to move my legs was limited and I could not touch Mistress as she was in a the blindspot directly behind me.

The pressure on my hole increased. By now I should really know better, but I resisted it nonetheless. I squeezed my rectum to keep the penetrator out.

“That's it! Keep that nasty big cock out of that cute butt of yours!” Mistress encouraged me happily. “Push harder! Don't give up!”

And I didn't. I fought with everything I got. As Mistress pushed I could feel my torso move forward slightly on its suspending chain, but the dildo did not go in. I dare say I felt pride on this little victory.

“Excellent. Well done my dear,” Mistress said. “Now then, you may put this big dildo where it belongs, Cheryl.”

I grunted. Get that thing away from me, I wanted to shout.

Mistress reached around me, easily avoiding my grasping hands. I felt a wicked sting as she pinched both my nipples.

“Humpfh!” I cried. Distracted by the pain, I realized too late I had relaxed my body. I felt my torso swinging back in the chain, impaling myself on Mistress' dildo in the process. I tugged on my shackles as the dildo slid in deeper and deeper. I only stopped moving when my behind bumped against Mistress thighs.

I kept struggling while the dildo prodded inside of me, arms and legs shaking. That amused Mistress greatly.

“Why, I've never seen a sissy so happy for having a big cock in her ass. Wait until you feel this.” She started to rock my body on the suspending chain, moving the strapon in and out without actually moving herself.

“Oh my, what are you doing Cheryl? Moving that tight little hole up and down my strapon. You are actually fucking yourself, you naughty sissy.”

I kept on struggling some more as she moved me up and down the shaft of her penetrator, but it didn't last long. Finally I just accepted it like a proper sissy should.

Big mistake. Whatever Mistress desired of me, it was not meek acceptance.

“What is this? Giving up? I think not!” She slapped my behind, pinched my earlobe, tugged my hair. I squealed in distress.

I felt someone pinch my clitty, then a crop struck my thigh. I squirmed in my bonds, but Mistress continued her assault.

I heard clack-clack and my bonds became a bit more slack. Mistress continued hitting me with her crop, sharp stings biting me on my behind, my back, my hands and even my cheeks. Encouraged by extra the freedom of movement, and shocked by the vicious stimuli Mistress poured over me, I freaked out and went into a frenzy. I kicked and swung my arms and cried and screamed in my gag.

“Much better.” I heard her say. Then the engine whirred again. Clack-clack-clack the chain went, and my hands were pinned behind my back and my legs immobilized. In my panicked tantrum I raged against my bonds, but all I got for my efforts was some useless shaking with my legs, a couple of sore wrists and a lot of muffled grunting that Mistress ignored as she pumped me while simultaneously teasing my clitty.

Goodness help me, I was getting hard! As excitement began to flow through me, I relaxed and stopped struggling.

Clack-clack-clack. My bonds went slack once more, and the pain returned as she began striking me with the crop again. She said something but I didn't hear it as the panic returned and my basic fight-or-flight response took over and I impotently raged against my bonds.

Clack-clack-clack it went, and once again I was securely bound. Mistress taking me from behind as one hand teased my clitty, while the other worked other erogenous zones.

And just when I thought I was about to come, she stopped. “Not yet, deary. Let's drain your energy before we drain that little clitty of yours, shall we?”

I heard the engine whirr and pleasure was replaced by pain and desperate struggling once more.

This cycled continued, again and again. I lost track how many times. She never let me orgasm, but each time letting me come so close.

“My goodness, Cheryl. You are an energetic little sissy, aren't you? What has Christina been feeding you?” Mistress asked me as some point. I only grunted in response as the cycle repeated again.

I was very tired by the time I was introduced to what Mistress called the 'rocking horse'. She had removed the blindfold, enjoying the dismay in my eyes as she guided me firmly towards the unfamiliar item. I had difficulty staying upright.

“This cost me a pretty penny, Cheryl. I hope you like it,” she said.

'Rocking horse' was actually a poor description. It looked more like a small version of one of those mechanical bulls you find at funfairs or carnivals. But where those machines are intended to throw their passengers off, this one bristled with straps and shackles to keep its rider firmly in place. The central part did look like a stylized European dressage horse though.

“Did you know that women can orgasm when riding a horse?” Mistress told me. “It's true. The shaking, rocking and vibration, the rubbing of the saddle. Very stimulating. Especially when you wear those tight riding pants. Unfortunately, I hate horses, which is a bit of a problem. I wanted something to replicate the experience without all the disadvantages of an actual horse.”

She attached the chain of my collar to a hook, keeping me in place as she turned towards something that looked like a control panel. Like I could actually go anywhere...

“But then I figured: why settle for just the stimulation of a mere horse ride when I can take it to the next level?” She pushed a button, and something inside the device came to life. From the saddle of the rocking horse two things suddenly appeared. A pair of dildos now pointed upwards from the saddle. My mouth would have been agape if it wasn't already gagged. 

“As you can see, it was made for me, but...” She pushed another button. The forward dildo retracted into the saddle again. The other one still stood firmly erect. “...I figured that my lovely guest should have the honour of 'riding her in', so to speak.” Her smile was from ear to ear.

I must have backed away in dismay, as suddenly my leash was taut. Mistress started unbuckling the straps and shackles on the horse. “I've added these features just for you,” she said with a grin as she undid a solid metal cuff. It snapped open with a short click loud enough to make me wince.

“There we go,” she said as she opened the last bond. She unhooked my leash and started pulling. “Come here, Cheryl. Let's get you strapped in.”

“Noff! Nohpfh!” I muttered as I shook my head. I tugged at the handcuff that still bound my hands behind my back. Using what little traction my heels gave me, I pulled on my leash. With whatever energy I had left, I resisted.

Which was pathetically insufficient, and Mistress just grinned as she slowly but inexorably pulled me towards the saddle. “Don't be silly, my dear. Sissies just love a little pony ride. Especially if the pony rides her.” She pushed a button on the control panel, and the remaining phallus started to hum as it began to vibrate.

I squirmed and struggled against my leash, but Mistress effortlessly placed me next to the saddle. “There's a good girl. Now, raise your foot. Put your leg over the saddle.”

I grunted as I cursed into my gag, tugging my leash. Mistress slapped me in my face.

“Cheryl! Behave!” She yelled at me, her sharp tone more vicious than her slap. Confused, tired and downhearted, I gave up my resistance. But not fast enough to Mistress liking. She slapped me again. “Raise your foot, sissy. Now!” she yelled in my face. I obeyed.

Unexpectedly, she cuffed me around the ears. Confused and scared, I felt tears in my eyes. “Oh for goodness' sake...” I heard Mistress say. “The other foot, stupid girl!”

Balancing precariously on one high-heeled shoe, I raised my right foot and put it over the saddle. The 'horse' was close to the ground (it was only a fancy torso with no legs) and I cleared it easily.

“Good. Put your foot down on the other side. That's it. Well done.” Mistress spoke. I stood there astride over the horse, the saddle directly below me and the phallus pointing straight at me.

“Now sit down. Don't worry, my dear. I'll make it more comfortable.” She turned to the control panel, and the dildo slid back into its resting place inside the contraption.

I was still reluctant, and mistress put her hands on my shoulders to urge me down. I rested my behind on the saddle.

“Put your feet in the stirrups, Cheryl.” I obeyed and placed my high heels in the metal frames, with the sole of the forefoot and the heel on opposite sides of the short metal bar. “Good girl. Now hold still.”

Mistress walked over to the side, and snapped the metal cuff shut around my ankle. Then repeated the process with the other foot. I could hardly move them.

With my feet secured, she turned to the wide leather straps at my thighs. She wrapped them around my legs and buckled them, fixing me in my sitting position.

I mumbled in surprise as she undid my handcuffs, but she did not let go of my wrists as she moved it in front of me. With her free hand she picked up the reins of the horse. They were made of leather, and so were the thick cuffs attached to them. She wrapped one around my wrist and with a metallic click closed the locking mechanism. My other hand was next.

Mistress looked at her handiwork, but didn't seem satisfied. She opened a clasp on the reins and started to tighten them, pulling my hands forward in the process until my arms were almost stretched.

She stepped back and gave me a good look. Her smile betraying her satisfaction. I must have been quite a sight, a girl in a pink dress sitting astride on some toy horse holding its reins. My gag and the consternation in my eyes must have been the icing on the cake.

“Why, don't you look positively adorable!” Mistress said elated. “Little sissy all ready for her horsey ride. Well, let's make it a ride you'll never forget.”

She pushed a button and I moaned in dismay as something beneath me started to move. It could mean only one thing, and sure enough I felt something sharp prod me between the ass cheeks.

I moaned as it pushed upwards. I still had some clearance around my thighs, and I pushed myself up. The dildo stopped moving, but kept pressing on my little hole. I squatted precariously over the saddle, the thigh straps not allowing me to stand upright. At least I managed to prevent the phallus from going in.

Mistress sniggered as she saw me struggle. “Oh no, no, no, silly girl. You need to sit down to enjoy a horse ride. Here, let me help you...” She put her hands on my shoulders and put her weight on me.

I moaned and grunted as she forced me down, the dildo moving up in my rear. “Relax, my dear. Let the horse do the work,” she said as she put more weight on my shoulders. She suddenly twisted my nipple, and pain shot through my chest. I lost my focus and whatever grip I still had. I fell the final inch on the saddle.

“Humpfh!” I grunted as the dildo pushed deep and hard into me.

“There you go,” Mistress said wickedly. “Now let me make sure you don't fall off...” She tightened the leather straps around my legs, then let go. I tried to force myself upward, but I could not get high enough to get myself of the penetrator in my behind. Defeated, I slumped back onto the saddle.

“Looks like you are ready,” Mistress said with a smile as she pushed buttons on the control panel “I'm almost done too... Yes, that should do it. Well, here goes...”

Her finger went to a big red button on the control panel, but stopped just above it. Her face stood pensive.

“I really shouldn't. It was not made for two people... But what the heck! One time won't break it, right?” She walked over to the horse and sat down right behind me, astride on the rear of the mechanical horse. She put her arms firmly around my waist, then kissed me in the nape of the neck.

“You comfy, sweetcheeks?” She asked me teasingly. I just grunted. “Good to hear. I certainly am. Let's begin.”

With her one hand she reached over to the control panel, and pushed the red button.

Nothing happened.

My heart jumped a little. I was horrified about my position as it was, and whatever this contraption was supposed to do, I was glad it didn't work. And purely out of spite, I rejoiced in Mistress' surprised disappointment.

“What the...?,” she said with annoyance. “Did we break it already? What a piece of crap!” I had to suppress a snigger.

Then an engine came to life. A vibration ran through the horse and an electric motor started to work. The horse began to move upward. I squealed in shock and fright.

“Ah, that's it. Hold tight, honey,” Mistress said, now elated. “Here we go!”

We had risen over two feet before the actuators had decided we were high enough. I looked around in fright, my dazed mind unable or unwilling to grasp what I was caught up in.

Then the horse started slightly rock and vibrate.

“Teehee. Do you feel that? That's exactly like the walk of a horse.” Mistress said with amusement.

I felt something, all right. In my behind mostly. But not any specific gait of a horse.

The rocking and vibration increased. “That is a trot,” Mistress said helpfully.

I moaned in my gag. The rocking of the horse was bad enough, but the dildo had started to vibrate as well.

The tempo increased further. The horse started tilting forward and backwards rapidly. “This is a canter, when a horse has three legs in the air and one on the ground.”

I didn't listen to her. I was preoccupied with trying to stand up, as the penetrator had begun to move up and down. I desperately wanted to get off, but my bonds kept me firmly in place.

Then the horse started to gallop. It rocked up and down as the horse ran at full tilt and took me along for the ride, airtime interspersed by shocks as imaginary hooves touched the ground. The movement of the phallus matched its pace.

Mistress was laughing like a little girl. A strange sound coming from someone who usually was so stern, mean and domineering. I heard her gasp as well. I guess she wasn't kidding about women and horse riding.

The horse tilted left, then turned right as if evading some unseen obstacle. “Whee!,” Mistress shouted.

I breathed heavily as the dildo went up and down inside me, its vibrations causing shivers down my spine. The rocking of the horse moved the penetrator in unexpected ways, causing discomfort and delight in equal measure.

I squealed as the horse jumped over something, and I groaned as the dildo pushed in deeper as we landed. “Yeehaa!” Mistress called out with elation.

The horse went into a steady and rhythmic trot, and I felt the saddle shiver and vibrate. I felt it in my groin. The front of the saddle touched my clitty and sissy-bells. It was true, I was excited.

The horse sped up again. Behind me Mistress laughed while I moaned into my gag.

The ride got rougher and the horse began to twist and turn.

“Whoa! It is starting to buck. Hold tight, Cheryl,” Mistress called out.

Strapped down as I was, I wouldn't fall off, but Mistress had to hold on tight. Her arms held me like a vice. She didn't seem to mind though.

“Whoohoo! Ride her, cowboy!” I heard behind me.

My mind was elsewhere though. The penetrator had started moving faster than ever. I mumbled in my gag, uttering words of both shame and ecstasy.

Up and down and round and round the horse went. Mistress now held me one hand holding the other one high, like a rodeo star. I just pulled my bonds in some vain effort to get off.

“Relax, dear.” Mistress said. “Enjoy it. Here, let me help.”

With her free hand she reached around me and under my skirt. Her fingers found my hard clitty. As the horse pranced and bucked, her hand teased my sissy-parts. I could feel her fingers touch and stroke up and down the shaft.

The horse now moved faster than ever, and I was sure Mistress would be thrown off. But she remained seated, one hand around my waist, the other touching my clitty faster and faster. Just as the horse pranced, rearing itself high, I came. With a gasp, a moan and a shudder, I orgasmed.

As on cue, the horse slowed down and came to a complete stop. I gasped from my climax, while the device lowered itself to its starting position. I was still breathing unsteadily as Mistress stepped off the back of the horse.

For a while I was surrounded by bliss. But eventually that euphoria faded and I noticed the sticky wetness between my legs, and my behind felt very sore. I really wanted to get off that darned horse. Still gagged, I tried to plead with my eyes for Mistress to untie me. She smiled in response.

“Well, that was fun. Want to go at it again?”

I shook my head. No, please no.

“I thought as much.” She grinned as she pushed the red button again. I squealed as the horse rose up and started to move around. The penetrator started pumping as well.

“It's not fair you should have all the fun,” Mistress called out from the side. “Let me join in too.” She picked up a wicked bull whip, which she uncoiled around her.

The turning of the horse took her out of my field of vision, but a sudden sharp crack next to me made me groan with fright.

“This will do just fine,” Mistress said as the horse turned me towards her again. The leather of the whip was curling around her like a living serpent.

The horse pointed its behind towards Mistress. A sharp sting went through my left thigh, making me grunt and moan. Another one hit my behind.

“Woohoo! Ride her, horsey!” Mistress called out as the stings of the whip and the movement of the horse and dildo started to encompass my entire existence.

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