Not Careful Enough Ch. 03

When I woke up in the morning I woke up grinding my hips into the mattress. I was trying to get morning wood but unable to on account that my dad's friend had locked my penis in a pink chastity cage when he found my pictures of me wearing women's lingerie.

I had a dream that I was back in the garage. My knees on the cold hard ground and a big hard cock was weighing on my face. I woke up when it started to spray my face with thick ropes of cum. When I woke up I had a phantom sensation that my face was covered in cum again. I had to touch my face to be sure.

I looked at my phone to see what time it was. It was really early but I already had several messages. One from my dad.

"Hey kiddo sorry I didn't get to stay for breakfast but I got called into the base early. There should be plenty of food in the fridge. Mom should be back this weekend."

That wasn't uncommon so I wasn't concerned but the other messages were from Jerry.

"Good morning baby girl. I'm going to be over early this morning to get you started off right."

Another message was attached to a picture of his hard cock in his hand.

"Can't stop thinking about that sweet mouth of yours."

I rolled over and pressed my face into my pillow and screamed. He was coming over without my dad being home. That didn't seemed to stop him from fucking my face in the garage but I knew it was holding him back. Now there was nothing to hold him back. I was nervous and frustrated and really horny. I haven't gone this long without at least jerking off for a little bit.

My phone chimed again and I looked at it and saw another message from Jerry.

"I'm in the driveway, come let me in."

My heart sank and I jumped out of bed and looked out the window. Sure enough Jerry's car was in the driveway. I put on my robe and rushed downstairs. I opened the front door and found Jerry and some woman.

"Good morning, girlie. This is Natasha, she is going to give you a makeup tutorial."

He motioned for Natasha to come in. When they crossed the threshold I stepped back and closed the door behind them.

"This is a lovely home," Natasha said in a thick Russian accent.

"Thank you...." I said kind of awkwardly.

"Gerald says that you would like to look like a beautiful woman. I can help you. Where are the supplies?"

"Um in my room... " I pointed behind me.

"Go get. We wait," she said.

Looking at Jerry and back at Natasha I awkwardly turned and went upstairs to my room. I pulled out the big box and dug in it to find the makeup kit. When I got downstairs Natasha and Jerry were in the dining room. She had set up a mirror and lights and some other makeup.

"Good. Sit." She commanded.

I am nervous now. I've never had makeup on before. My hands were sweaty and I was getting those nervous shakes where it looks like you're shivering.

When I sat down I stared into the lights and the mirror. I couldn't really see the woman but I could see the objects she brought to my face. She applied so many things I didn't even know what was happening. It wasn't until the pink lip gloss that I got a good look at my transformation. I was shocked.

"That's my pretty girl," Jerry's voice rang out.

I immediately felt self-conscious. I really did look pretty.

"Okay now go change." The woman commanded.

I got up and marched up to my room. Once in my room I realized that they didn't tell me what to put on. They were making me choose my own outfit. I sifted through the box and found a schoolgirl outfit with pink trim that matched my lips. I opened the package and put it on.

The hard shell of the chastity cage made a slight bulge in the pink pleated skirt but with my makeup and now my makeup I really looked like a girl. It didn't hurt that my short blonde man bun could be mistaken for just a short ponytail.

As I left my room and descended the stairs all eyes turned to me. I could feel my face getting warm and wondered how much it let on I was blushing. Why was I blushing?

"My work here is done." The woman said.

She was already mostly packed up. When she closed her case and walked to the door it was dawning on me. She was going to leave me alone with a man that has already forced me to suck him off and now that I look like this there was no telling what he was going to do to me.

I stared at her walking away and through the front door. I turned to look back at Jerry and found him already staring at me hungrily. I averted my eyes and suddenly felt really self-conscious that the link skirt I was wearing barely covered my panty covered butt.

I took a deep breath. My back was facing Jerry and I heard his footsteps behind me. Before I realized how close he was I felt hands wrap around my waist. I shuddered and retreated into myself. His big strong hands ran up and down my body.

"Now you look like the part." He whispered in my ear.

His breath was warm on my neck and sent shivers down my spine.

"Do you have it in?" He asked in a husky voice.

Before I could speak he already had a hand up my skirt and down my panties. I felt a finger touch my butthole.

"I didn't have a chance... " I defended myself.

"How about we do something about that?"

He then started to push his finger into my hole. I tried to squirm away at the sudden invasion but he held me tight. Once he was in he started pressing on my prostate immediately. I gasped with a new sensation.

"That is one tight pussy Mary."

I moaned unwillingly as I bit down on my glossy lips.

"How about we take this up to your room?" He suggested.

He removed his finger from my hole and I felt a sudden emptiness and longing. I caught my breath and led him up the stairs into my room. Once in the room he closed the door behind me and pulled out his phone.

"Now how about you get on your knees."

He pointed the phone to me and I slowly sank to my knees, never taking my eyes off the camera.

As he walked towards me I gulped nervously as he fiddled with his zipper. Once he was standing over me and my head was tilted up towards him he pulled out his hard cock and slapped me in the face with the weight of it.

"Be a good girl now and maybe I'll let you out of that cage for the day."

I raised a hand to his hard shaft and pointed the head to my mouth. As I wrapped my lips around his bulbous head I was aware of the straining pressure in my crotch.

"Who knew the captain had such a cocksucking slut for a daughter."

I knew it was rhetorical but even if I wanted to reply I couldn't because Jerry now had a firm grip of my short ponytail. All I could do was glare at him as I bobbed my head on his thick, hard cock.

"You ready to get fucked bitch?"

This time I tried to shake my head but with his hand firmly in my head he nodded my head in agreement as he forced his cock deeper into my mouth.

"That's a good girl. Take that cock down your throat. Such a good cocksucker. I know you want it."

I coughed and choked on his big cock in my throat. I tried to push him off but he held firmly in place. When he did release me I dislodged his cock from my mouth and caught my breath. I leaned over heaving when I felt him push me over.

I caught myself with both hands but now he had hands on my hips and pulled me up so I was on my hands and knees facing away from him. I looked over my shoulder at him as he raised my skirt and lowered my panties. He dribbled a generous amount of cold lube onto my butt and rubbed it in with his hand.

My heart was pounding as I watched him apply another generous amount to his own cock.

"Please! I don't think I can do this," I told him over my shoulder.

He gave me some gentle pats to my bubble butt and chuckled.

"Don't worry baby this will only hurt for a minute. If you had used that bigger butt plug this would have been easier."

He pulled my hips back with one hand as he held his cock with his other. I felt the head of his bulbous cock pressed against my lubed ass. I faced forward and arched my back and steeled myself at the intense pressure at my backdoor. It hurt the more he pressed into me. I squeezed my eyes shut and grit my teeth.

When the head of his cock broke through the seal I screamed in pain and felt my eyes well up. He then began to push his cock deeper. Into my ass. I continued to groan and push my back on him. I pushed my hand back on his leg.

"Please stop! You're too big! It hurts. Please stop!"

He didn't stop. He just continued to push slowly but firmly into my ass with his big, hard cock.

"Almost there baby. Just take some deep breaths and relax. Trust me."

The pain led to a burning pressure and I could only imagine his big cock tearing me open. I couldn't take a good deep breath. I was practically hyperventilating. Finally he stopped pushing deeper into me and we just hung there. My ass was pulsing and squeezing his thick cock.

When my body seemed to calm down and relax I felt the pull as his cock retracted nearly full length before being pressed back into me. This time though it didn't hurt. It didn't really feel like anything except tingly. I only felt the internal pressure and the compression on my prostate.

"How's that numbing lube feel?" Jerry asked.

Astonished, I admitted it didn't hurt anymore.

"It's better. Oh my god. You're still really big."

I was now breathing heavily for an entirely different reason. Now it was because he was rhythmically fucking me in the ass. I just watched as the world jolted back and forth.

"Do you like it bitch? Does that big cock feel good fucking your ass like a sissy bitch?" Jerry grunted pumping into me.

I was getting delirious already. Everything was so surreal. I felt pretty. I felt like a pretty girl. I felt like a pretty girl getting fucked like a dirty slut. I couldn't help myself.

"... Yes..." I sighed, lifting a great weight from me.

Then he grabbed my ponytail and yanked my head back and he leaned over me and shoved his phone in my face.

"Yes, what bitch?" He growled.

"Yes I like it sir." I corrected myself.

"Tell the camera what you like," he commanded.

"I like getting fucked in the ass, sir." I tried not to voice my shame.

He released my hair and I hung my head. He gave me a firm slap on my ass.

"That's a good girl. Bounce back on that cock. Beg for more."

"Please fuck me," I whispered, my head still hung low in shame.

Jerry smacked my ass even harder.

"Louder bitch!"

I raised my head and turned back to see him holding his phone still. I steeled myself. I knew what he wanted. I figured if I played the part we could get this over with quicker.

"Please fuck me Daddy! I've been a bad girl Daddy! Punish me with your big hard cock in my ass Daddy!" I begged in my best girliest voice.

I was pulling from the sissy hypnosis video he sent me last night. He seemed pleased and put the phone down. With both hands on my hips he bucked hard and deep into me causing me to gasp and moan automatically.

"That's a good girl begging for it. Beg like a dirty slut you are."

He was thrusting so hard into me that I was practically drooling from mouth breathing. My eyes were having a hard time focusing everytime he stimulated my prostate with his big hard cock. He was fucking my so hard and fast.

"Fuck. Me. Daddy." I stammered out breathlessly, "fuck me. Daddy. Fuck me Daddy! Just like that Daddy!"

Jerry was grunting with every thrust now. It was turning me on even more. I could feel my penis flopping hard against me now. I could feel pressure building up behind my balls. It felt like I was going to cum. I've never cum while soft. This new sensation was incredible. I was moaning loudly now.

"I'm going to cum inside you bitch. I'm going to breed your sissy ass." Jerry growled animalistic and breathy.

I was fully delirious now. My eyes were rolled to the back of my head. I felt like a rag doll bouncing to and fro. My tongue was dripping out of my mouth. When he started to grunt and pound long and hard I felt it. His cock pulsed inside of me and I felt like I was filling up. As he pulsed inside of me I began to cum at the same time. While he was spraying my insides with his generous jizz I, on the other hand, pooled semen underneath me in a pathetic stream.

Jerry held me tightly in place until he stopped pulsing and then slowly pulled out of me. When he released me I collapsed on the floor. My brain felt like it was on fire or in a lightning storm. It felt like I was buzzing. I could feel something warm flow out of my sore ass but I couldn't dare move.

"Such a good girl," Jerry's labored voice rang in the ether. "An ass this good I got to share with the rest of the squad."

While I knew what he said I couldn't manage to voice my objection. I tried to move but was unsuccessful. I tried to beg him not to tell anyone but I couldn't form words. I just laid there on the floor and mumbled incoherently.

"Shh you rest now." Jerry leaned in over me and stroked my hair. "Rest now. I'll be back tonight to pick you up. Practice what Natasha taught you and wear something sexy."

He kissed my neck and felt shivers run down my spine. Then I felt something wrap around my neck. It was broad and tight but not too tight that it made it harder to pant but tight enough that I couldn't ignore it. I finally managed to move and brought a hand up to touch whatever it was around my neck.

It was a collar with a bedazzled 'sissy' on it. I just kept running my hand over it not understanding why I was feeling this.

"This makes you mine now bitch. When I pick you up tonight you better be wearing it. And plug that ass. We don't want you shrinking back down or else it'll hurt every time."

I stopped fondling my collar and managed to raise my head and focus just in time to watch him leave my room without looking back as he closed the door. I laid my head back down and listened as the doors closed and the car's engine started.

What have I become now?