Where did My Damn Key Go Pt. 02

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Part 2 of Jared's torture.
5.1k words
4.58
17.8k
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Part 2 of the 3 part series

Updated 06/08/2023
Created 04/09/2018
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It didn't take me long to find something to wear. The lucky choice of attire was a sexy school girl's outfit I used to wear in a lot of my "private" encounters. It was complete with a blouse and plaid mini skirt. To make sure I was up to bitch's standards, I threw on some makeup here and there to give me a bit of an edge.

A little bit of lipstick here, some mascara there, it was my usual routine with crossdressing. If I wanted to be pretty, I could make myself look damn attractive. That I know for sure. But now I was doing it for the sake of my locked up manhood.

At the living room clock, the time showed 7:58. I had just a little bit more time. But even I didn't waste those precious moments. I went over to the bathroom mirror gave myself a once-over, looking at every inch of my body. I looked cute enough. To be honest, I looked damn right delicious! I always loved my school girl outfit.

I managed to give myself just enough of a fake bust to give a little eye candy up front. And I already had a nice plump ass in the back. Add a pair of white lacy underwear and I was ready to play the innocent little school girl being sent to detention. So many good times were had with this outfit. But sadly, none of them could distract me from the current situation.

I glanced at the clock one more as I reached for my phone, dialed the number once again, and waited as the busy tone repeated itself. On the third time, I heard a voice from the other side.

"Good evening, my little pet," The female's voice chirped. I was beginning to hate that fucking voice. It made me want to smash her face in.

"Just get to the point. Alright? Now-"

"Ah, ah, ah," She said cutting me off. "I'm the one in charge now, pet. Now unless you want your key back, you will do exactly what I say. Now is that understood? "

I thought for a moment. I thought real hard. I was in no room to trade, compromise, or even talk about the current situation. She had me by the balls, both literally and metaphorically. And all I could do was follow suit and pray that she delivered in the end. I swallowed before speaking. "Yes," I managed to say.

"Yes, Mistress," she said right after. "You will refer to me as Mistress. Understood pet?"

God, I really wanted to deck her so much. But I played along. "Yes... mistress."

I heard a giggle from the other side and I swear she was probably smiling with a devilish grin on her face. "Good girl," she replied. "Now, I want you to go to this address immediately. It's two-thirty-eight, Hollow Way Boulevard. I'm sure you can find your way around to get there."

"Yes, mistress," I replied dryly

"I thought so, "she said. "But don't dilly dally. I will not tolerate my pet being late. Understood?"

"Yes... Mistress." I felt like a mindless zombie repeating myself over and over again. It was starting to get irritating. But I had to keep on going with this game. She let out another giggle as she spoke.

"Good to hear. I'll be waiting, my pet." She then hung up.

I placed a hand on my temples as I went to my computer. Thank God for the internet sometimes. If you wanted to find something quick, All you had to do was Google it. Need a number? Google it. Need a recipe? Google it. It was one of the many marvels of this age of technology.

Yet, I had such a primitive device strapped to my cock. Nevertheless, I found the directions with ease, copied them to a loose slip of paper, and headed out the door. It was now time to meet her, sadly not on less stressful terms.

About ten minutes had elapsed while I ventured down the sides roads of town, keeping my form away from any wandering eyes. I loved my outfit to death, but I wasn't the type of guy to show it off in the middle of public. If it was a private show, I'll be all for it. I'll even have a lot more fun if the person I was "entertaining" was blindfolded.

But out here, I felt naked. The cool wind didn't help at all as the breeze constantly swiped at my skirt. But I managed to get to my destination without any major difficulty, occasionally slipping in a nearby hiding place here and there to avoid the crowd's sight. I made it.

Before me, was a small house. There was nothing out of the ordinary that I could see. It looked too small to suggest that she was a multimillionaire big shot. And it was smack dab right in the middle of a neighborhood. It was odd at first. But I was starting to understand her point of view a little. I mean if I was a two-faced bitch, I wouldn't want to stick out like a sore thumb.

Her place looked similar to the other houses around hers, sharing similar qualities. All of them were made from brick and wood, had one driveway that led to a garage, and was only one story tall. Good thing there weren't any dogs out. The last thing I wanted was her neighbors being alerted about a cross-dressing man that was approaching her house.

Still, I walked towards her house, being mindful of the front yard as I went to the door. I really didn't want to give her any more reasons to be pissed at me. As I approached the door, I knocked on it twice and waited. Then it opened, revealing the voluptuous female from the bakery again.

I was already ogling at how she was dressed, feeling my mouth agape at her appearance. She wore a black latex corset that pushed her breasts upward, giving them a nice little boost. Knee high boots encased her feet. Her hips swayed, parading her latex panties. A riding crop was in her shiny gloved hand, tapping the end at her palm. I couldn't help but stare. I was still angry at the sneaky little bitch. But my god did she look hot in all of that latex. For a moment, I stood there in awe, unable to speak.

She slapped her open palm again. "Inside my house, pet," She ordered firmly, holding the door for me. Part of me wanted to argue, wanted to snap at her. But the other half got the best of me, commanding my legs with a docile manner, entering inside. She closed the door as I entered. And before I could even get one word out of my mouth, she pushed me, hard, forcing me against the wall of the guest hall.

The tip of her riding crop shushed me as those domineering eyes pierced right through me. I couldn't help myself. I froze up, unable to speak or act, almost helpless as her ruby lips curled upward and small dark giggle slithered past them. "Now you're all mine. And just to make it clear. You WILL do exactly as I say, to the key. Any lip from you and there WILL be hell to pay. I will make sure of it."

Her presence seeped out of every word she spoke. My voice was stuck in my throat. But I slowly nod my head, biting my lip. Instantly she grabbed my arm forcefully and flipped me around, pushing my face into the wall. "Hands behind your back pet." I did what she said, placing them at the small of my back. Then, I started to hear clicking and the rattling of chains.

"W-wait." I managed to blurt out. "I was supposed to get the key from you, right?"

I was about to add more to my question. But she quickly snatched a handful of my hair, pulling me to her face, hissing into my ear. "Did I say you could speak, slut?" She said. Her voice sent chills, shivers that crawled all over my skin. Why did I felt so weak, so powerless? Each second I was in the room with her, I felt as if my pride as a free man was being stripped away.

She threw my head back to the wall and suddenly I felt the cold steel of bracelets around my wrists. I tested my hands for a moment, realizing that I couldn't separate them. Well, that answers my question if she put handcuffs on me or not. She snatched me from the wall when I was done, spun my body around, and returned my gaze back to her eyes, those evil ruling eyes. Her gaze was sharp and forceful, making it difficult for me to keep my sight locked on her.

"Now, my pet," She started again. "If you would like the privilege to cum again, then I suggest you be a good little girl." I could feel her finger brush against the metal of my cock cage. Please take it off. Please. "If not. That's always fine by me." She withdrew her finger and her smile grew wider. "I've always loved disciplining wild animals." I swallowed spit and averted my gaze. What did I get myself into?

My new mistress yanked my bound arm and pulled me down the hallway as I hung my head down, averting her eyes but still feeling her suffocating presence. All my resistance had been drained, burned out. Just like that, I was done. Was it because she had my key? Was it because of her look? It could be because damn she could wear a corset.

I was confused, silent, watching my surroundings as she guided me to the house. It was a small house. Nothing was completely out in the ordinary. The hallway and rooms that she guided me into reminded me of a nature cabin interior, giving off a very distant vibe to the area.

She then stopped, grabbed my face and pulled my gaze to hers. Those eyes. They were burning, radiating with absolute dominance. Just staring at them shattered my pride, ripped my dignity apart, and destroyed any ideas of defying her. I felt shivers tickle my skin at her glare, her aura suppressing any rebellion in me. I was losing this battle.

"Kneel," she growled and suddenly my knee went weak. My body fell to the ground, standing at my knees as I lowered my head. My mind was still remembering her glare, that strangling gaze. The heel of her boot rose up to the back of my neck, pushing my head to the soft rug below me. The act made my rear rise up in the air like a cat in heat. A small grumble crawled out from my throat. And she quickly responded with a swift stinging blow from the crop to my ass. "Did I ask for your opinion pet?" She snapped at me.

"I wasn't-"

SWAT!

"I didn't-"

SWAT!

I was wincing at the pain, grunting, curling my fingers. She had a good arm, that for sure. Either way, I decided to stay quiet, learning my lesson from the previous strikes.

"Well?" Her voice was rising, sharpening. It cut at me like a knife, causing me the shudder, cower, painting fear deep into me. That fucking bitch!

"... no, mistress," I replied meekly, earning me another smack from the crop. I bit my lip and closed my eyes. I can't believe this. I'm so pathetic right now. At any point in my life, I'd never stoop to such a low. And in a matter of minutes, the will in my voice was crumbling, breaking.

Her boot stepped off me, followed by more harsh whips from the crop. My lips pursed in a vain attempt to keep quiet, enduring, not showing any verbal response. Please stop. Please stop smacking me. Even though I didn't say those words, I could hear my mind beg silently, desperately wanting her to show mercy, not wanting to feel more of my new wrathful mistress. But finally, she stopped, grabbing her hair and yanking my head up slightly.

I groaned as a new device flashed into my view. Something made of metal was forced into my mouth. At first, the object's size shocked me, forcing my jaw wide open as she pushed it past my teeth. It was a ring with two straps that she pulled on tightly, fastening the ends at the back of my head. I tried to jerk my head away to dislodge the ring. But she fought back harder, holding my head steady as she finished securing my gag.

She walked in front of me and stuck her boot right in front of me. I looked up at her, hesitantly. I didn't know what she wanted. But I didn't want to get hit again either. All she did was look down at me with that same burning glare. "Clean my boot, pet," she ordered firmly. I blinked as I looked at her boot. She couldn't be serious. Did she really mean what I think she meant? Just swallow your pride, I told myself. Your dick is on the line. And there was no compromising with her.

I stretched my neck out and reached over to her boot, snaking out my tongue. The taste of her leathery black boot slammed against me as I lapped at the surface, scrubbing it diligently with my tongue. I moved as best as I could, maneuvering my head to get every angle. If only I could use my hands. If only they weren't bound by cuffs. Still, I kept going, despite the abuse that my palette was receiving. Now all I needed was approval. I heard her giggle as I continued to clean.

But, all of the sudden, She pulled me away from her feet. Her action threw me off guard. And before my brain registered the move, she had already shoved her hand deep into my open mouth. I choked and gagged in response. Not that I wasn't used to putting things in my mouth if you catch my drift. But a heads up would have been nice. I needed time to suppress my gag reflex. Now, I was jerking my head in reflex, groaning and resisting. The taste of her gloves coated my tongue.

I pulled away only for her to bring my head back with a forceful grip. With the same protruding hand, she slapped me across my face, marking my face with my own spit. Her emerald eyes fired a glare straight down at me, stunning me, causing me to rethink my next move. "You're only bringing this on yourself pet," She spoke with firm words. "I can be just as cruel, if not more, as the disrespect you give me."

I could feel her grip tightened around my neck as I looked up to her. Then she flung me down on to my back and pinned me to the floor with her heel, pressing the point down on my chest, injecting the pain deep in the flesh. She leaned down as her hand slithered into my skirt. I was too busy trying to adjust my cuffed hands to retaliate. But I felt her frisky fingers massaging the cold metal of the cock cage.

That teasing bitch! Just lightly touching it was making my member slam at the bars, quickly hardening, wiggling around to find freedom. But alas, there was hardly any room for my cock to thicken, leaving me even more frustrated than ever. "I'm only going to say this once, slut," she ordered, firmly molding her words with her ruby lips. "Unless you want to me to 'forget' where I hid your key at, you WILL do exactly as I say. Do I make myself clear?"

The question echoed in my mind. What was she going to do to me now? What was next on her list of evil? And when was I actually going to get my key back? So many uncertainties! So much pressure! Caving in finally, I nodded, trying to say, "yes, mistress," with an open mouth. But my words only presented themselves as a garbled mess.

A sneer formed on her face as she lifted her heel. "Good answer." God, what have I gotten myself into?

"On your feet, now!" She barked, turning her back on me as she walked towards the other side of the room. Her hips swayed as her heels clicked, keeping her same demeanor. How can something so evil own a body so sexy? I mean if I wasn't in this situation, I would be flirting with her madly in hopes of a chance to get a piece of that ass. But now was DEFINITELY not the time to be gawking over some tail.

I got up as fast as my legs could scramble, pushing up to my knees first before standing up. My cuffed hands made it difficult at first. But I quickly adapted. I hope I don't have to wear these for too long. I tested their strength. They were solid. But my mind started to worry a bit about blood flowing to my hands properly.

Suddenly, the dominatrix distracted me again. She returned back to me with a new toy in hand, a black slender cane that she ran her fingers up and down. Pulling up a nearby chair, she sat down, legs crossed, smirking at me as I stared at her with both fearful and vengeful eyes. Her hand extended and her finger gestured for me to come. "Don't be shy, my little sissy," She teased, her voice alluring. "I only bite if you want me too."

A small giggle was added to her last sentence. I wanted to glare at her, growl at her, curse her out. But I already know where that will take me. Defeated by the circumstances, I shuffled my feet and lowered my head, embarrassed. This was humiliating. No, this was degrading. As I got closer to her, I closed my eyes and avoided eye contact. Then, I knelt back down to her. But she placed a hand on my chin, forcing me to look back at her.

"Stick out that tongue of yours," She ordered. I instantly jerked my head out of the way, out of her grasp. She tried to wrestle her grasp on to me again, but I still fought her. Then suddenly, a very sharp pain exploded from my groin, causing my eyes to widen and to keel over a bit. I groaned through an open mouth as I noticed where she hit me at with that cane. That's just cruel! You can't just hit someone in the family jewels like that! "I said stick out your tongue. You WILL do what I say, slut," She said firmly.

I had to turn red at the sound of that word. It was true. I was one. Hell, I was a really huge slut. But, I wasn't going to let the slut in me consume me. This is not me the real me. I can control my urges. Needless to what I was and what I wanted to be, I submitted to her demands.

I let my tongue stretch out through the ring gag, hanging limply for her to see like a dog panting. She raised her cane up to the muscle and rubbing the tip up and down it. The taste of polished wood hit my palette again. It wasn't as bad as her heels. But it made me worried where she would strike me next with it. Her smile widened at my worried look.

"You have such a dirty mouth, pet," She said, "I just can't believe how much of a filthy talker you are." Suddenly, she slapped my tongue sharply, causing me to grunt through the ring gag. Another strike came, causing me to wince at the pain. I still held it out. "You even talked back to me when I was trying to tell you about your servitude towards me. And then there was the name calling." I tried to swallow spit. I had a bad feeling about this." Let's see. What was that you called me again? Oh, that's right. You called me a BITCH!"

Another strike!

"And you also didn't ADDRESS me properly."

Another strike!

"and you even had the gall to demand the key without permission!"

Another strike!

By now, I was already whimpering and crying out in pain. It was so much that my tongue began to retreat back in its wet cave. But she snatched me by my neck. "I said keep it out! Do it now!" she hissed at me. Her eyes burned into my skin as she kept those raging emeralds fixed on my skull. But I did what she said.

Out it went again as she continued to spank it mercilessly. This time she held on to my neck, making sure I didn't leave. She let me have it, giving one good smack after another as I beg desperately for her to stop. But my pleas were incoherent, unintelligible, only coming out as, "leasssh tah! Leeaash!" But the only thing she was paying attention to was her sadistic act, My eyes watering from the pain.

Finally, she stopped, letting go of my neck and letting me hide my tongue as I jerked away from her grasp, cowering in front of her. She stifled a laugh with her gloved hand, holding the cane in her other one. "I hope you enjoyed your punishment, pet," She said, "I surely did." I only looked at her, cautious of that smile. But I nodded.

"yeh, issress," I managed to get out, adding to my display. The gag was really getting in the way. But I just had to endure. I had to just play her game. The messed up part of this all was I starting to enjoy this. The spanking, her calling me a slut, the teasing she gave me. It was arousing me more than my one night stands. And why?! I didn't like this! I was trying to control my horniness, not make it worse!

She grabbed me by the hair again, opened up her legs, and stuffed my face deep into her grown. Her musk, the leather, all of it hit me harder than anything she did to me. It attacked my nostrils, taking away my supply of oxygen. My lung screamed for clean air as she rubbed my face all over her crotch.

"Feel free to take a lick, pet. You have my permission," She cooed saucily, letting out a delightful moan as she continued. Without thinking, my abused tongue came out again, lapping at more of her leather items. Deep down I wish she would rip off those panties and shove my face into her wet womanhood. God, I want her. I want to eat out that pussy and make her scream. The smell of her nether region was getting my libido revved up. And any second, I was about to beg and pant like an actual dog.

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