Straight to Sissy Ch. 05

DISCLAIMER: This chapter contains themes which could potentially turn off certain readers. This includes, but is not limited to, watersports and forced exhibition. I do hope you read with an open mind, but if this isn't your thing, don't worry! The story will progress quickly and I hope you join me for future chapters.

Chapter 5 of the adventure. After spending the previous evening learning what it means to serve a man, I'm hoping for a bit of a breather. But my Master, perhaps sensing my vulnerability, has other plans.

I woke up the next morning in a bit of a daze. The events of the previous evening felt like a dream, but the soreness in my ass reminded me it was very real. I reached for my phone to check the time. 10:30!! And two texts from my new Master. I shot up in bed, suddenly shaking in anticipation. For some reason, I hadn't considered he'd be contacting me so soon.

The first message came in at 7:45 and read, "What is your schedule today sissy?"

The second was at 9:50 and simply said, "Answer me slut"

I leaned my head back and groaned a bit, immediately regretting having slept in. Hopefully Master would be a bit merciful after using me so thoroughly the night before, I thought. My cock twitched as I opened the reply screen.

"I'm very sorry Master, my schedule is open today, how can I be of service to you"

I figured at this point it was smartest to be as subservient and eager as possible. I had no idea what was in store for me but I had to treat the situation cautiously.

As I waited anxiously, I wondered if I'd get another round of cock today. Even though I had cum while getting fucked the night before, it didn't satisfy me like a real orgasm would. I had gone into last night thinking it was an experiment, but as my little clit twitched again I realized perhaps I would start craving it.

The buzz buzz vibration of my phone brought me out of my spontaneous cockdream.

"You could have been of service to me two hours ago when I first contacted you. Have you already forgotten your most important sissy rules?"

It came rushing back to me. Master's cock buried in my mouth while he told me my most important rules. My sissy emotions.

My fingers shook as I typed my response.

"No Sir, I was just tired after serving you last night. Please let me serve you again today!"

I couldn't believe I was already begging to be used. His reply was immediate.

"You dumb slut. You should know "tired" is no longer an emotion you have. What good are you to me if you're asleep?"

I felt like he was being ridiculous but his seriousness only added to the gravity of the situation. I felt all I could do was plead for forgiveness.

"I'm very sorry Master, I will do better next time! I don't want you to be disappointed in me."

"Good. Know that I always expect a timely response from you and you will continue to learn your place sissy. I'll have you on a proper schedule soon enough. Don't expect this transgression to go unpunished. Now get your little hole plugged up and over here. You have 30 mins."

An address followed. I shot up in bed again and fumbling with my phone, I plugged it into Google maps.

Fuck! A 25 minute drive! Barely any time to get ready.

At this point I was shaking like a leaf as I tried to clear my head. Okay, first things first I thought. The small buttplug was still on my bedside stand, right where I had left it the night before.

I grabbed it and reached down between my legs. I was still a bit wet from the night before, and almost without thinking, I spit on the plug and pushed it steadily into my hole. It sank in almost too easily, as if it was always meant to be there.

Looking down, I saw the same clothes I wore the night before. I quickly threw them on, figuring it didn't really matter what I wore, since I'd be naked sooner or later anyway. Practically running to my car, I checked my phone for an ETA. 3 minutes late. How had I already wasted so much time!

As I drove, it was difficult to concentrate on the directions. My mind continued to wander to possible punishments I would have to endure. Of course I knew of the usual BDSM type punishments, like spanking or bondage, but I felt that this man was particularly inventive and ruthless.

Glancing down I suddenly realized I had made a wrong turn. Fuck Fuck Fuck, I thought, seeing that I was now running 5 minutes late. I felt my hole clench on my plug as I tried to refocus on driving. I'd just have to endure another punishment I suppose.

As I pulled up, the house felt familiar, but also somehow different during the day. Jumping out of the car, I ran to the door and remembered another rule. I must always be naked and kneeling. Did this apply to this situation? Standing there at the door, I wondered what to do. There was more traffic on the street now, and it seemed like every window in sight was watching me.

Nervously glancing around, I decided I couldn't risk another punishment. In one swift motion, I threw off my clothes, rang the doorbell and knelt. Anxiously, I looked around again and then decided to put my head down. I waited for what seemed like an eternity, hoping no one would notice a naked boy, kneeling in front of a door in broad daylight.

Finally, I heard footsteps and the door opened. Almost immediately, I tried to crawl in, but Master moved quickly to block me. I looked up at him, pleading.

"Ah look at you sissy, you've progressed so fast! Already naked and kneeling begging to come inside to be used. Who knew you'd be such an eager sex toy?"

At this point I felt like I was going to have a heart attack. "Please please Master let me come inside!!!" I begged.

"But you're late slut! You know that means another punishment? Maybe I should leave you out there for another 6 minutes!"

"Pleeease no Master!! I'll do anything!!"

"Was that a "no" out of your filthy mouth sissy? You'll wipe that word from your vocabulary and now I have a third thing to punish you for!"

I groaned and meekly put my head down offering a "Yes Sir."

"Turn around slut, let me see that plug!"

Accepting that at this point I'd be out in the world for all to see, I turned around on all fours, leaned forward and spread my ass to show off my plug.

"Now there's a good girl, showing off her first piece of jewelry, sparkling in the sunlight."

I felt myself beaming a little, finally receiving some praise for what I was putting myself through. I decided I would accept any situation for my Master if it meant I could feel appreciated.

"Turn around and look at me, slave!" he demanded, sternly. I spun around, kneeling meekly in front of him, looking up obediently.

"Okay slut, now you'll have to endure your first punishment today. Hopefully you'll learn that saying "no" is no longer an option for you. You should always offer and even beg to do anything I might enjoy and I rather enjoy the idea of you waiting out here for me. So why don't you stay right there like that, perhaps you'll be ready to serve me after some time outside."

I started to open my mouth to protest, before realizing better. He slammed the door in my face, leaving me there, naked and kneeling on his stoop. I looked around nervously, and an ominous fear of being watched washed over me. I felt an urge to retreat to the safety of my car, but I knew that would be a very bad mistake.

Cars whizzed by as I wondered how long I would remain here. Maybe if I just didn't move, no one would notice me. I shivered as I felt a cool breeze against my skin. The sun gleamed high in the sky, and I felt myself squinting in the bright sunlight.

Suddenly out of the corner of my eye, I saw a dog appear from behind a bush as it made it's way down the road. "Oh my God," I thought to myself, "someone is coming." I was mortified, but remained frozen, like a deer in headlights bracing for impact.

My heart dropped. A beautiful blonde woman appeared next. Her hair was pulled back in a tight ponytail, and a tight teal sports bra hugged her large breasts. Black, capri-style yoga pants and white joggers completed her look. She had a slight smile on her face, clearly enjoying her walk and the beautiful weather.

I quickly looked away, back towards the door, shifting awkwardly on my knees, hoping she wouldn't notice me. Every second felt like an hour as I could hear the distinct sound of her walking behind me. As my anxiety increased, I stole another look back towards her. She was looking right at me, with a confused look on her face, and I hurriedly looked away again, shifting my hands to cover my exposed crotch. I felt the tip my penis in the palm of my hand, small and shriveled in embarrassment.

I could hear the footsteps continue down the road, and finally, I mustered the courage to have another glance to see if they were gone. I could see her round, soft ass accentuated by the yoga pants as she walked away. Just days ago I would have been yearning to grab an ass like that, imagining the view as I fucked her from behind. Now I could only whimper as I waited patiently for my own ass to be used.

Moments later I finally heard the door open again.

"What a good little whore waiting patiently for her Master! Would you like to come inside sissy?"

"Yes please Master," I mumbled.

"Good girl, why don't you crawl in here before the neighbors see!". He chuckled.

I crawled through the door and stopped, kneeling in the entrance looking up at my new Master. "How the hell had I gotten myself into this predicament?" I thought. Just the night before, I had messaged this man out of simple curiosity, only intending to see what serving a cock would be like. Not commit myself to it fully. My mind flashed through all I had experienced the night before and I felt my little clit spring to life. I wasn't sure what was happening to me, but I would have been lying if I said I didn't like it.

As he closed the door I noticed a thick, pink leather collar with a matching leash hanging from the knob. The word "SISSY" gleamed across it, the metal letters almost seemed to glitter in the light. Master snickered, looking down at me. "Looks like you're excited to serve me again today slut. I like that you're eager but don't worry, we'll get rid of those pathetic little hard ons soon enough." I gulped, smiling nervously.

I craned my neck letting him place the collar around my neck. The leather felt cool and slick on my skin as I heard a lock click behind me. I gulped again, much more aware of my submission as I swallowed.

He pulled the leash tight and led me down the hall to the bathroom. I could feel the plug shifting in my ass as I crawled, a now ever present reminder of my new purpose. When we arrived at the bathtub, he pulled me towards it, "Get in." Crawling over the side, he gave me a swift slap on the ass as I fell in awkwardly.

I sat back on my knees, looking up at him solemnly.

"Now I was going to break you in with this a bit more slowly, but you can think of this as punishment for oversleeping this morning. It's also a valuable lesson for a whore. You'll soon become accustomed to the taste of my nectar and if you really are to become a perfect sissy, you'll eagerly await it."

I nodded, nervously, fully aware of what was to come.

I could see the outline of his cock through a pair of navy gym shorts and I felt myself staring. I couldn't help it!

He pulled it out as I looked up almost in a trance of admiration, my mouth agape with lust.

"You like what you see don't you sissy?"

I gulped, "Yes Daddy,"

He pulled it out of his shorts, shaking it in my face, snickering.

Suddenly I saw a geyser shooting down at me, seemingly almost in slow motion but too fast for me to react. It hit my open mouth and filled it quickly as the liquid started flowing down my cheeks and neck.His piss continued hitting my mouth like a fountain and then he began to redirect his stream, coating my face and hair, covering any remaining dry parts of me.

Finally, I could sense his stream subsiding and he moved it down my chest quickly, pissing on my penis and then back up my chest.

I was breathing heavily, sputtering a bit, trying to regain my breath after the deluge on my face. It felt as if it had gone down the wrong pipe and was dripping up my nose and stinging my eyes.

"Thank you Master," I muttered mindlessly. He tucked his beautiful member back into his shorts as I stared and panted. He pulled his phone out, snapping a few pictures, smiling gleefully. "We certainly need to commemorate this moment, don't you think sissy?" He asked, laughing.

"Yes, please Master. Thank you again," I whined, suddenly eager to please him.

He laughed, "You know, this is why I love sissies. I can already tell you're going to be one of the best. No self respecting person would let me do this! But look at you, you love it! You're little clit's been hard this whole time!"

I smiled. I knew his comment was meant as a criticism but it did make me feel special, unique and appreciated. "Sure, this might be a little gross," I thought, "but I really want to please Master."

"Well sissy, I hope you enjoyed your golden shower. I'm sure it will be the first of many, But now it's time for your next lesson. I looked up at him, feeling the moisture drip off my hair and down my back as I nodded in agreement.

"You have far too much hair for a girl don't you think sissy?" He reached into the cabinet under the sink as he spoke, retrieving a pack of female razors and a pink bottle of shaving cream.

I gulped. I didn't have much body hair, and I wasn't what you'd call a masculine man, but realizing what was next required with me I hesitated with fear. What if people noticed?

I nodded meekly. "But I..Sir..?"

Don't even think about it bitch!" He yelled as he spit on my face. "Do you really want to find out what I'll do if you don't start obeying me without hesitation?"

I gulped again. "No Sir."

"Then sit up you fucking whore! This is an important step for you and I know you don't want to disappoint me so get to work! I don't want to see any hair below your fucking eyebrows when I get back." He threw the razor and the can towards me and turned the water on the overhead shower. The shock of the cold water hit my skin, causing me to jump and spasm, clenching the plug still in my hole.

"I'm so sorry Master, yes Master," I stammered, clutching the razor, looking down at my body as I shivered in the cold, unsure of where to begin.

"Don't forget to shave around that sweet pussy of yours, you want to make sure it's extra pretty for your Master! And don't even think about turning on the hot water, you certainly don't deserve that privilege," he said snickering as he left the room.