Good Girl Ch. 02: New Beginnings

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Sissy takes a big leap toward her new life.
4.1k words
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Part 2 of the 7 part series

Updated 10/29/2023
Created 10/17/2023
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A few weeks had gone by since Mark and Miss Anne helped me learn some things about myself. I spent as much time as I could dressed while I practiced with make-up and my feminine mannerisms. I became more accustomed to my clitty cage. It became part of me - a reminder of what separates me from men like Daddy.

I never looked for the cameras Miss Anne had hidden throughout the house. As much as she has done for me, I did not want to be disrespectful.

I also grew to enjoy the thought of her, and whoever else she may have let in on my secret life, watching over me. She rewarded my faithfulness with an occasional care package. Body washes, lotions, bath beads, and candles arrived one day with a handwritten note about keeping sissy skin soft.

Another package arrived later with an assortment new panties, a sheer crotchless bodystocking, and two pink collars with the words "Princess" and "Cumslut" on them.

Occasionally, I would receive a text message from "Mommy" when I would try something new. The first time I tried on the collars, I wore them both so that they read "Princess Cumslut". She approved. I was rewarded the next day when a delivery driver dropped off yet another package.

This one required a signature though. I had been spending the day cleaning the house and prancing around in a cute sundress. I was feeling so good that when the doorbell rang, I answered it as I was. A pretty young woman was holding a medium sized box. She gave me a subtle double take and then read the box, "I have a package for Princess Cumsl...?". My face was flush, but I finished her sentence, "Cumslut. Yes, ma'am. I'm Princess Cumslut". She paused a moment and then responded with a laugh, "Well, you go girl. Can I get your signature Ms. Cumslut?" I signed her device and as she walked away. I could hear make a phone call while walking toward her delivery van, giggling, "You won't believe what just happened."

I closed the door. I just told a complete stranger that I'm a cum slut and a princess. My humiliation quickly turned to excitement for my new package, however.

I received an immediate text notification: "(Mommy) LOL, That was precious, sissy! We should do that more often... I think you'll enjoy this package the most."

It felt heavier than the last few. The shifting weight as I carried it to the bedroom peaked my curiosity. This box was full of sex toys, lubes, restraints, and what appeared to be a shower hose with a metal dildo attached to it. As I examined that shower hose, I received another text from Mommy, "That's for keeping yourself clean. There are instructions - follow them carefully. I have fun days planned for you, Ms. Cumslut ;P"

Moments later, "(Mommy) Also, start small at first. I can't wait to see which ones are your favorite. Use lots of lube. Don't worry about running out. I will send more when you need it." I could sense her excitement for me.

I sorted the toys by type. There were a lot of anal toys. Dildos and plugs of various shapes and sizes filled most of the box. Some looked like real cocks. Some looked far from realistic. Some were intimidating. I lined them up on the bedroom dresser and ran out of space.

Amongst the toys were two books: a guidebook to anal sex for beginners and another a guidebook to becoming a good bottom. I read both cover to cover that night.

I put the new toys to use immediately. I explored different positions. I used them in bed, on chairs, and in the shower. I tried different angles. Some had suction cups that I could stick to a surface and imagine I was riding Daddy. I preferred those to the manual ones. When I left the house I was plugged and wearing panties as Mommy instructed me.

My fantasies had focused more on penetration since Daddy probed my pussy with his fingers. The feeling sent waves of ecstasy through my body and I wanted to explore the sensation more. I suspect Mommy caught on as my viewing habits began to trend toward anal sex and pegging.

The next couple weeks passed uneventful as I worked around the house. There were no new showings and I wondered if I would see Daddy again soon.

Mommy offered encouraging messages as I began training with the new dildos and plugs. She told me when she wanted me to be plugged, when she wanted me to use a dildo, and when to go up a size. She was training me to take bigger and bigger cocks. As I did, my body ached for cock more and more. I was becoming a size queen. I suspected my training was going as Mommy planned.

One day, I was mowing the front lawn as a moving truck pulled up in front of the house. I watched as muscled workers carried boxes and furniture to the house across the street and through the garage. I had it bad that day and found myself fantasizing about the four big moving hunks carrying me into the house like a piece of furniture and then taking turns on me from both ends. I played the fantasy out in my head in detail. I felt like I was in heat. The lust boiled up and I made up my mind to get some moving muscle dicks. Before I realized I was lost in my daydream, I had finished the lawn and the moving truck had left. I sighed in frustration and went inside to fuck myself silly with a veiny black dildo while I showered. But this time, the experience was different. The new dildo Mommy picked hit a spot and my legs buckled. What on earth was that? I attempted to reproduce the feeling by varying my depth and angle until suddenly I found it again.

My big black veiny cock instantly became my favorite new friend. I felt pleasure swell up inside me not unlike the feeling I had playing with my clitty before it went into Mark's cage. I found a rhythm that felt incredible and I began pounding myself right at that spot. After a few minutes, my entire body began to tremble and my clitty leaked little spurts of cum as I moaned in delight. I didn't even touch it!

A puddle of cum formed at the front of my cage, and without hesitation I caught it in my free hand and smeared the half teaspoon of my own cum on my tongue. It tasted different from Mark's delicious cum. It was thinner and didn't have much flavor. Nonetheless, I was happy to have any cum in my mouth again, even if it was my own. I cleaned up my toy and cage and finished my shower.

When I exited the restroom, there were multiple messages waiting for me:

"(Mommy) Keeping going, princess. I can tell you're close!"

"(Mommy) I'm so proud of you. Your first auto-sissygasm!"

"(Mommy) Good girl, now swallow it"

"(Mommy) OMG, You're such a dirty slut"

"(Mommy) I think it's time for your next lesson, sissy"

"(Daddy) I'll see you tonight, slut"

I was floating on clouds. Mommy's praise was enough, but I could not stop thinking about Daddy's message, and his cock. I wanted to be ready for him.

I went to my closet to find the perfect outfit - something that said "Please fuck me" that would make his cock hard.

Then three more messages:

"(Mommy) No more eating today. Use the shower hose to clean yourself good at 5:00."

"(Mommy) When you are clean, put on both pink collars, the crotchless body stocking, the ankle and wrist cuffs, and insert the pink puppy tail plug into your pussy"

"(Mommy) I want you kneeling on the bed at 6:00 with that pussy in the air. Make Mommy proud, slut"

Time passed slowly at first. Then 5:00 came and I began my preparations as Mommy instructed. I was prancing around the house and singing, giddy with the anticipation of how Daddy might use me. I climbed into the shower and cleaned myself as the manual instructed. After the shower, I used my favorite moisturizing lotion that came in one of Mommy's care packages. It had light accents of lavender and linen and left my skin soft. I slid into my pink sheer bodystocking, fastened the Princess Cumslut collars around my neck, and locked the restraint cuffs on my wrists and ankles. I wondered why we needed these as I didn't have anything onto which to lock them.

It was 5:45 so with the last several minutes, I lit candles around the room.

Then I retrieved the pink puppytail plug and a bottle of lube and got into position on the bed. The plug was one of the larger ones, so it took some time to work it in. Once I was adequately lubed, I was able to lock it in place. I felt full and I could feel the vibrations of the wagging tail when I moved. I wasn't going to be able to walk with this monster planted inside me. I could only crawl or present my hole. I supposed that was the point of this particular plug. So, I placed the bottle of lube on the nightstand and got into the most fuck-me position I could assume with my pussy facing the door. I passed the time enjoying the sensation of the plug spreading me open.

Minutes passed like hours until I heard the front door open. My heart starting racing again with anticipation. I was eager for Daddy's approval.

Footsteps trailed around the house for a few minutes and then I felt the draft from the bedroom door opening. I wagged my puppy tail for Daddy and then felt a sharp slap on my exposed ass. I heard Daddy's voice for the first time in weeks, "You keep shaking that ass, but don't move yet, slut." Then I felt something cold slide under my legs. Moments later there was a clicking sound at my right foot.

Daddy's rough, powerful hand grabbed my left foot and spread my legs further apart. A second click. I realized my ankles were shackled to a spreader bar. I had seen those in bondage videos. I recalled how soundly each of those sluts took a dick and my excitement grew.

Then something I wasn't expecting - Daddy reached up between my legs, grabbed both of my wrists and pull them under me between legs. The sudden loss of my support caused me to tumble forward face first into the mattress and my puppytail went higher into the air. I let out another gasping whimper as I felt Daddy lock my wrists to the spreader bar between my ankles.

I was helpless and vulnerable. A little fear had mixed with anticipation and I was a primed fucktoy for Daddy. He slapped my puppytail which sent shuttering vibrations through my pussy. I moaned out, "Oh, Daddy. Please use me." His voice trailed away as he left the room, "Oh princess, we will." I heard Daddy's voice call out into the house, "She's in here and she's ready". I felt a larger presence enter the room.

I heard unrecognizable voices:

"Looks like this bitch is in heat"

"She needs some dick"

"You have to breed a bitch if she's in heat"

I felt a gentle, continuous tug at my tail. Pleasure mingled with a little pain as the bulbous plug popped out. Then I was empty. I felt cool air rush into the hot cavity left by the plug's removal. Then, I felt someone bump the bed behind me. I could hear zippers coming down, buttons unfastened, clothes piling on the floor. Four? Five? I couldn't make out he number of unique voices I heard.

Then a voice said, "She got the lube ready for us. This bitch can't wait to get fucked." As he walked toward the lube at head of the bed, he passed my eye level and I saw his waist. His cock was pointing straight out from his body, swaying back and forth as he walked. I couldn't make out the size. But, long.

He walked passed me again to the foot of the bed toward my waiting pussy. I heard the squirt of the bottle and the wet sounds of a lubed cock being stroked. The bed shifted and then steadied. I felt a hand grab my left hip.

Daddy walked toward where my head lay on the mattress, caressed my face and offered his thumb again. I sucked it for a moment and then I felt a heavy cock slapping my hole like it was a door knocker.

Daddy pulled his thumb away and laid my phone down where I could see the screen.

A message notification rang out:

"(Mommy) Welcome to your new beginning. Make Mommy proud, slut."

I felt the head push against my pussy. My body offered only a moment of resistance before giving way to his meat. The cock plunged into me inch by inch, tunneling down until he stopped and I felt a hand on each hip.

"Ready bitch?" the voice called from above me. I could only reply with a meak whimper, "Please fuck me, sir". He started slowly fucking me at first while grasping the side of my ass. I was in heaven.

His cock was commanding right of way and my pussy yielded. Before long I could feel his pace start to quicken and his hips bounced off my ass. There was a deep burning, ache when he bottomed out the first several times. I knew he was pushing my limits. I had felt that while under Mommy's training.

That soon gave way again to pure pleasure. He was giving me his full cock. He wasn't as thick as the largest dildos Mommy made me train with, but he was at least as long. His thrusts were causing me to moan and whimper.

Then I heard him begin to grunt and without warning seven or eight warm spurts flooded my hole in quick succession. As commotion filled the room, I heard camera shutters snapping. My impregnation was being documented by an unknown number of men.

Where would these images and video end up? I wondered for a moment. Then, the rest of my breeding party cheered as he planted his seed deep inside me.

Many more than four or five where in the room. I must have miscounted by about half. As his eruptions subsided, I felt my inaugural breeder withdrawal from my hungry pussy and he released his hold on my ass. I longed for him to push himself back inside me. I had gotten used to the sensation and now I felt empty.

Dismounting both me and the bed, he announced to the room, "She's lubed up now! Next?"

My phone began to chime:

"(Mommy) Look who just became a cumdump. You took your first load like a real slut."

"(Mommy) I enjoyed watching your first breeding. Get comfortable, sweetie. Only one down, and I see a line growing. You're in for a long night."

"(Mommy) p.s. I have a surprise for you when they are all done using your holes. Have fun. ;)"

While I was reading Mommy's words of encouragement, I hadn't noticed that Daddy's second friend had already gotten into position. This time, I felt strong hands grip my pelvis and rock me back.

His powerful arms held my torso horizontal so that Daddy's third friend could sit at the head of the bed. As Friend 2 slid his cock into my cum-filled hole, he let my hips slip slowly forward so that my face lowered into the lap of Friend 3.

Friend 3 grabbed the sides of my head and guided his shaft into my salivating mouth. The gathered crowd stirred again as someone called out, "Spit-roast that bitch!"

I could hear hips slapping against my ass through my muffled throat sounds and gasping breaths. I was a two-holed fucktoy being used by a couple of horny old men. It felt perverse and degrading, and I loved every second.

I could still hear the camera shutters and see the flashes. I wished to look into the lenses so the world would know what a cock-hungry, cum-drunk slut I am.

I heard the man I was sucking say something and then I felt the man inside my pussy rock me back. Friend 3 pulled my mouth of his sloppy wet cock and rose to his feet. I looked up longingly to see the cock that I wished was still in my mouth.

I saw it glistening with my spit, as a rope of his cum sprayed across my face from my right check to my left forehead. I flinch at the unexpected baptism. Four more shots fired point blank into my shocked face. Each caused me to flinch to the enjoyment of the room. The last one found it's way into my gaping mouth. Camera flashes lit up the room. I smiled gleefully at them as thick cum slowly trickled down my face.

I savored what I could catch in my mouth, swallowed one big load, and showed the room my tongue to a round of applause. As the furor died down, Daddy's second friend planted himself deeper inside me, locked his arms around my waste, and grunted his forceful load into my bowels. I felt like a bitch being mounted by a stray. I could feel his breath in my ear and his heavy balls rattling my clitty cage with each thrust. His cum was very hot and it found it's way deep inside me.

Friend 4 and 5 immediately took position where the others had been. The room was getting hornier and the hard cocks were growing impatient. As I was getting spit-roasted by my next two customers, two older men took position on each side of me. From the corner of my eyes, I could see them stroking their meaty shafts while playing with their nipples. They meant to plaster my face. Friend 5 was ready to nut and he assumed position above me. This time I was ready. I looked up, opened wide and accepted all three of their gifts almost simultaneously. Whistles and shouts filled the room as I took another load in my sissy pussy. The horny energy in the room spurred me on. I craved the approval and attention. I couldn't have realized how I need it until I experienced it.

Cum streamed from my face onto the bedding. I wanted it all in my tummy but my hands were shackled and I was at the mercy of the room. I swallowed what I could catch and then found myself pleading for more cock, more cum.

The room filled with laughter as I began to degrade myself for their pleasure. Daddy stepped forward and freed my wrists from the spreader bar. I greedily swept the cum into my mouth and swallowed it down.

I looked up and phones were pointed at me from all angles. My display was being recorded by almost a dozen men. I smiled and waved to the cameras. Giggling through a sticky smile, I asked "Are you proud, Mommy?" I could finally see all of Daddy's friends who came for my special day. I was in awe at the amount of cock in the room.

My phone chimed:

"(Mommy) I only counted seven loads. You're only halfway done. Get to work, whore."

My pussy felt slippery and loose. I reached back to feel it with my newly freed hands and my fingers plunged into a gaping hole. I had to use four fingers just to feel the sides, but they slide in with little effort Witnessing the shock of my transformation, Daddy whispered in my ear, "You've been cunted, princess. You have a real pussy now. You'll be taking a lot of dick from now on". I looked in his eyes and said "Thank you, Daddy" in a pleading tone that really sounded like I was begging for more.

He stood tall and shouted, "Next!"

Two more swinging dicks stepped up and I was put to my hands and knees. The man in my pussy was big and had a curve to him. Within a few thrusts, he found my magical spot I discovered my veiny black friend and I was lost in the room. He could sense that he had me on the edge and he started to pound my button.

I heard somebody loudly ask, "has anyone popped the pinata?"

"No!", the room shouted back. My body spasmed, I let out a loud, effiminate shudder and sissy juices dribbled from my clit. The room cheered and I could hear voices shout, "We have a winner!"

I didn't know what the shouting meant, but suddenly our champion was releasing a much deeper, guttural moan as he pulled out and shot his seed into my gaping hole. The man in front of me release a few jets of cum into my mouth and pulled out as a forth and fifth shot across my painted lips. I wonder if my mascara was running down my face mixed with the loads I had taken. Was my lip gloss smeared across my face? I could only imagine how slutty I looked.

The last three men picked me up and put on the floor, kneeling beside the bed, as they each face fucked me in turn. I took all three loads down my throat, kissed their drained balls, cleaned their cocks and coyly thanked them for the privilege.

I felt like I had a liter of sperm swimming in my stomach. With every movement, more leaked from my gaping hole. I was a mess, as was the floor and bedspread.

With the last cocks satisfied, I felt a sense of accomplishment. Daddy gestured to the champion of our mystery contest, "Claim your prize". The curved-cock god picked me up, threw me over his shoulder, and carried me out to the foyer.

Daddy told me to kneel in the middle of the room with my hands behind my back, kneed spread. My dozen beautiful cocks formed a half circle behind me and Daddy snapped pictures of my achievement.

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SC_sissy
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