Becoming Chastity Pt. 02

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This is a series about a trans girl (18) and an older man (34). If that’s not your thing, I understand. Please continue to enjoy my other work. Thanks!

When we got back into the king-sized bed I snuggled right into Dominic’s side. He felt warm and safe. I hadn’t felt that since I was a child, laying on my father’s chest. But now I had a new father figure. Dominic was my Daddy now and I felt so loved and cared for in his big arms. A tear rolled down my cheek and I smiled to myself like a silly girl, in love for the first time. A few moments later we’d both be asleep.

I woke up the next morning laying on my tummy with the sun coming in through the big tall window that took up most of the wall on my side of the room. My Daddy was laying beside me, kissing my neck softly as he stroked my back.

“It’s time to wake up, Chastity.”

Hearing him say my name made a smirk break across my face and I laughed. Chastity. I turned to look at Dominic over my shoulder and he kissed my lips. He groaned softly into my mouth and I felt his manhood swell against the back of my thigh. Daddy was hungry for my body.

I pulled away from the kiss and laid my head back down, then closed my eyes to pretend like I was going back to sleep. My smile gave me away. I lifted my butt up and gave Daddy a good view of my cute little ass, still in the lacy white panties I’d been wearing since the night before.

Dominic climbed on top of me and forced my hips back into the bed with his own. I let out a gasp as he dominated my body with his big hands. I was completely at his mercy and I could tell he liked that a lot.

I felt just how massive his cock was for me. He was at least 10 inches and so thick. I felt him grinding it against my ass, only the thin fabric of our underwear separating our skin.

“Daddy please…”

His hands were on either side of my head and they held the weight of his toned upper body, as he rocked his lower half down against my butt. I reached up and held onto his wrists as he simulated the sex he wanted to make to my boy-pussy.

“Fuck..” He growled and flexed. His cock was laying between my cheeks now.

“I want you to be my first, Daddy.” I said meekly. I knew I wanted it, but it was still hard to say out loud.

I felt Dominic pull his cock from his underwear. He slapped it on my ass, making my plump little cheek jiggle. He yanked down my panties. I let our a yelp as he manhandled my teen body. I felt him spread my ass open and spit on my hole. Instinctively I flexed it tight.

Daddy pressed a thick finger against my little asshole and circled his spit around my rim. Once I was sufficiently wet, he pushed his finger in. Even as I took a deep breath and tried to relax, my hole wouldn’t open for him. His index finger was too big.”

Patience, sweetheart. You’re not ready.”

Dominic rolled off of me and laid back on his side of the bed, offering me a frustrated smile. I knew he wanted to fuck me. And although I was relieved Daddy had stopped pressing on my tight asshole, I pouted. I wouldn’t be able to give him my cherry right there in the morning light.

He brushed my messy hair from my face and tucked it behind my ear. “Do you want Daddy to take care of you? Help you get your ass ready to take me?”

I blushed and kissed him deeply, then climbed on top of him, straddling his lap. “Yes, Daddy,” I giggled and bounced up and down for a few second and then stopped.

I looked down in wonder as I saw our mismatched sizes. I was barely 4 inches, less than half the size of my Daddy. It didn’t matter. It felt good to be pressed against him. I leaned forward, laid on Dominic’s chest and let out a sigh. I felt so content. We cuddled like that, grinding softly against one another until it was finally time to get up and start the day.

*****

When we got out of bed it was 10:10am. I followed Dominic to the closet he picked out a clean white dress shirt from gemlik escort the rack. I turned around and he helped me put it on. I stepped in front of his mirror. The shirt matched perfectly with the white bra and panties. I brought the sleeves of the shirt to my nose and breathed in the scent of my Daddy’s clean laundry.

Daddy patted my butt and smiled, “Come on, I’ll make you some breakfast.”

I took Dominic’s arm and held him tight as we walked out down the hall to the front of the apartment. Once in the kitchen, I took a seat on the stool next to the granite counter top and pulled my knees to my chest.

Dominic opened the fridge and started to prepare our breakfast. He had put on some grey joggers and every time he turned to face me, I couldn’t help but to admire that big snake of his. God, I wanted to satisfy it in every possible way.

Dominic sliced some fresh fruit and put it all in a little bowl. Strawberries, raspberries, blueberries and mangos. He put a dollop of greek yogurt on top and handed me my bowl.

“Mmm… Yum… I love berries!” I said with a big smile.

“That’s good,” Dominic said as he spread the avocado on his sourdough toast. “So this is the first step in your preparation.”

“It’s important to eat clean like this before I fuck you.” He took a bite and folded his arms in front of his bare chest as he chewed.

My body shivered as I digested what he was implying. I hadn’t given it much thought, but it made sense. I needed to be clean and ready for my Daddy whenever he needed me. I took a slice of strawberry in my mouth and nodded obediently.

*****

We finished breakfast and Daddy took my hand and led back to his room. He crossed to his bathroom and over to the freestanding bathtub to draw us a bath. When the water temperature was right, he stood up and took me in his arms.

Daddy took my face in his hand and pulled my mouth to his. I shrugged the dress shirt off of my shoulders and then reached for the waistband of his joggers. We undressed one another and enjoyed the feeling of our naked bodies pressing together. When the bath was ready, Dominic turned the water off and we slipped in together.

There was a comfortable silence between us as I laid there, my back against his chest. He washed my body carefully.

When he got to my chest, I reflexively covered up a bit. “Sorry. I… I get a little shy sometimes.”

“There’s nothing to be shy about, Chastity.” His voice was warm and he kissed my ear.

“I just… I wish my body was more feminine, you know? I want my body to reflect how I feel inside.”

“I can help you with that,” he whispered against my ear. “But one thing at a time, sweetheart.”

Daddy told me to get up and on my knees, with my little ass out of the warm water. I did as I was told and wiggle my butt back and forth trying to be cute. Dominic laughed and smacked my ass softly. It made me jump. Then I felt my Daddy’s finger on my little hole once more. I looked at him with trepidation and bit my lip.

“It’s alright, Chastity. Relax. There’s no rush.”

I took a deep breath and exhaled slowly. I closed my eyes and cleared my mind. Daddy pressed his soap fingers against my little ring for a while, letting me get used to the pressure and helping me connect with the muscles I was trying to relax for him.

And then I felt one finger slip in. I tensed up on instinct and tightened around the invasion in my most private place. “Oh God!”

“Shhhh… It’s alright, sweetheart. You’re okay.”

I nodded nervously, as Daddy left just the tip of his finger inside my butt. After a few moments, he slid in a little. I tensed again, but then felt him pulling out slowly.”

Breathe, babygirl. In and out.”

“Yes, Daddy.”

He took his time fingering my ass. Each time his finger pushed a little deeper. After a few minutes, the pain and the fear began to give way to inegöl escort an intense pleasure I’ve never known. For the first time, I was being penetrated my a man and it felt incredible. With my eyes still closed, I started moving back against Daddy’s soapy finger. In and out.

“Good girl, Chastity. You’re doing so well.” I could hear the smile on his face. I was making Daddy proud. It made my little clitty leak.

It wasn’t long before Daddy slid another finder inside me and I bit my bottom lip. Immediately the discomfort returned. But this time it only took a few moments for the pain to melt into a warm tingle.

“Can I touch myself, Daddy?”

“No.” His curt response made me shiver as he butt fucked me with two fat fingers.

“Okay, Daddy.”

He fucked me like that for a few more minutes, until I was nice and stretched. Finally, he pulled his fingers out and I let out a little whimper of disappointment. He rose out of the water and I looked up at Daddy standing there with water glistening. He looked like a Greek God. Fuck. I wanted to worship this man for the rest of my life.

“Stay right like that, babygirl. Ass up in the air.”

I obeyed. Dominic rinsed the soap out of my ass with clean water. When he was finished, he gave me his hand and helped me out of the tub. We kissed deeply, and then toweled off.

*****

Once we were dry, he walked me to his closet and pointed at the rack on the far wall.

“Find something cute to wear,” he said with a pat on my butt. I giggled and again, did as I was told. It felt so natural to take orders from Daddy. There were so many pretty outfits to choose from. It made me think of the other girls that must play with Daddy and my heart sank a bit. A bit of jealousy crept in, but I did my best to push it out of my mind. That morning and the night before, I was the only girl for him.

When I came back out, I had on a simple yellow floral print sundress with orange poppies and green leaves.

Dominic looked me up and down. “God damn. You look so good, Chastity.”

“Thank you, Daddy,” I blushed hard.

Daddy was in a white t-shirt and tight black trunks. He sat on the bed with a towel laid out next to him. On it were a myriad of items. Daddy walked me through each one, explaining how and when to use the enema and then the douche to clean myself for sex.

“In the meantime, I want you to wear a plug for me. It will help you stretch throughout the day.”

I nodded, sheepishly.

“Use your words.”

“Yes, Daddy,” I said with a giddy smile. “I’ll wear a plug all day and stretch my butt for you.”

“Good girl. Now come here and lay across my lap.”

Once again, I obeyed his commands. He pulled the sundress up, revealing the pink bikini cut satin panties I’d picked from drawer. Daddy hooked his fingers in my waistband and pulled them down, leaving them around my ankles. I grinned and bit my thumb.

I heard the click when Daddy opened the lube, and felt the cool liquid on my skin as Daddy dripped it all over my ass and down my crack. Then I felt his warm hands begin to rub it in. I shivered and my little clit jumped against his thigh. His fingers pushed a good amount of lube inside my ass. To my surprise, I was still relaxed enough to take them.

A moment passed before I felt the cold steel of the plug on my hole.

“Now this is the smallest plug I have. It shouldn’t hurt,” Daddy soothed me with his words as he pushed the plug inside me, stretching my ass just a bit wider than his two fingers at the very widest part.

I whimpered as I was opened up wide and then let out a soft moan as my ass swallowed the plug.

“You’re doing fantastic, baby. I’m so proud of you.”

“Thank you, Daddy!” I wiggled my butt to show off for him.

“Once your butt gets used to this one, we’ll start going up in size.”He smacked my ass with his hand and scooped me up in his escort bursa arms and kissed me sweetly. “I’m going to take care of you this weekend, show you what to do. When you go home, I want you to make sure you stretch for at least a couple days before you come see me. Can you do that for me?”

I looked in his eyes for a long beat and the smile on my face melted away.

“I… I live in a dorm, Daddy. I share a room with an absolutely heathen and I get zero privacy.”

He studied my face for a moment and then spoke. “Well… would you want to stay here with me this week? You can commute down to Palo Alto to go to class and come back here to spend the evenings with me.”

It took a little while for me to register what he was offering me. “You want me to stay here with you?”

“Sure,” he smiled. “Just for the week… to try it out.”

I couldn’t contain my excitement any longer. I wrapped my slender arms around his neck and kissed him hard before breaking away to look at him with tears in my eyes. “Yes Daddy. That would be a dream!”

He kissed me back, pushing his tongue in my mouth while he groped my butt under my sundress, still slick with lube. We made out for awhile and I could feel Daddy getting hard for me again. I slid down between his legs and helped him get our of his underwear, freeing the enormous cock.

I looked up at him with an innocent smirk and wrapped my little hands around his root at the base. He was so long and thick. It was impossible to imagine him fitting this monster inside my little butt.

I worshipped his crown, kissing all around as he drooled pre all along my tongue. Daddy laid back on his elbows and watched his plugged princess worship his manhood. First, sucking on the tip, then taking him deep and deeper into my throat, just like the night before.

I gagged and coughed up drool, making sure to spit it all over his shaft to help my small hands glide up and down. I leaned in and sucked on his balls, slick with my throat cum, one at a time. I wanted to be his perfect little pornstar.

Finally, I felt the confidence he’d been building in me for two days now coursing through my body. I put my hand on his chest and pushed him on his back, then tried to lift his heavy legs. I couldn’t lift one leg by myself, but Daddy took the hint and pulled his leg up, resting the on my shoulders.

I leaned in and pressed my nose and mouth into Daddy’s asscrack. His slick balls were right on my face as I explored his ass with my tongue.

“Holy shit..” Daddy called out.

I needed better access. I pushed on his legs once more and Daddy bent his knees, pulling his legs up and making himself available to his little slut-in-training. One of my hands continued to work his shaft up and down while the other pulled his asscheeks apart so I could taste him.

I circled his little wrinkle with my tongue and then pushed it inside. Daddy let out a low guttural groan as I thanked him for being so patient with me. I felt so powerful, as I penetrated this man I’d given complete control to.

I’d always kind of known that I would be a total ‘bottom’, but in this moment, I knew for sure. My little cock was so hard, but I had no interest in touching at all. Daddy had become my everything and only his pleasure mattered.

I ate his ass and stroked his cock until he was ready to explode. His breathing was fast and shallow. I knew it was time for my reward. I leaned back and Daddy rolled himself forward, up to his feet now, standing in front of me. I opened my mouth and stuck out my tongue with big eyes smiling up at him.

“Ahhhhh…” I giggled a little at how slutty I was being. “Ahhhh…”

Daddy didn’t wait long. He painted my pretty face in his warm cum. When he was finished, I was covered and my mouth was full of his thick semen. He looked down at me, panting hard.

“Fuck…” He could barely speak, wiping the sweat from his brow. “Good girl. You’re so fucking pretty.”

I moved my tongue back and forth to show off my reward. I even scooped his load from my chin and the sides of my face in my mouth to make sure I could taste as much of Daddy as I could. “Now swallow,” he said, as he started to catch his breath.

I obeyed.

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