Becoming Chastity Pt. 01

Growing up trans in a small town was difficult. At the time I wasn't out yet and presented as a femme boy. I was bullied relentlessly at school and it wasn't much better at home. My Dad wanted a son who was more of the masculine ideal. Tall, powerful, good at sports, charming with girls. I was none of those things.

I was skinny and meek. I had a hard time making friends and had no interest in girls, so I retreated into my imagination and spent a lot of time by myself in my room. You can probably guess how I spent a lot of my time. Suffice it to say I started to figure out who I was and who I wanted to be.

My Dad was as supportive as he could have been during those years. I knew he loved me, but he couldn't hide his resentment for who I was, and more specifically who I was not. He became more and more distant and that hurt me deeply. My mom was out of the picture at an early age and my Dad was all I had.

I wasn't very social in high school which meant I was able to focus on my studies, eventually graduating near the top of my class. I was offered a scholarship to Stanford. My Dad was so proud of me for getting a full ride at a premier University. I realized how starved for his approval I was. He'd been so cold for so long that I began to crave his attention and admiration.

That Fall I headed out to Palo Alto and moved into an all boys dormitory. It was absolute Hell. Now not only was I getting bullied on campus, but I was forced to share a room with a guy who was fucking obnoxious. Once again, I retreated into my safe space. I signed up for a fetish dating site and made a profile.

Within a couple weeks I matched with someone and we began talking. His name was Dominic and he was everything that I had ever fantasized about. He was tall and muscular, had a great smile. Everything my Dad wanted me to be. At that time I still hadn't come out as trans, but it was starting to show. My hair was long, down past my shoulders and I always dressed in tight fitting clothes.

Dominic asked me to come over and I was ecstatic. This was the man of my dreams and he wanted me to come to his home. But then it dawned on me that I was still technically a virgin and he was probably expecting sex. Doubt started to creep in. What if I wasn't good enough for him? What if he rejects me? What if? But then I looked around at my 8x8 pigsty of a room and my roommate passed out and snoring, splayed out on his bed and thought, Fuck it.

*****

It was 7pm when I left campus and headed north on the 101 to San Francisco. Dominic ran a startup and lived in a penthouse at the top of a lavish apartment high-rise downtown. I left my car with the valet and took the elevator up to meet him. Once on his floor, I got lost down endless hallways, finally arriving at his place.

I knocked on the door quietly and a few moments later, Dominic answered. "Hello, you must be Tanner," He said with a warm smile. "It's so nice to meet you. Come in." Dominic was everything his photos promised and more. He had charisma and I felt magnetized to him immediately.

I followed him inside and his apartment was incredible. It was 2 or 3 times larger that the modest home I grew up in, with huge windows that showed off a stunning view of the city. "Can I make you a drink?" He asked as I felt his warm hand on the small of my back.

I felt electricity shoot through my body. "Sure. I'll have whatever you're having. I'm easy." I covered my mouth in shock. "I'm so sorry. I didn't mean it like that."

Dominic smiled and took my hands into his. "Relax. Take a deep breath." He said kindly. "Don't put so much pressure on yourself."

I looked up at him and smiled back. "Thanks. That's really kind of you to say." I blushed.

Dominic made us drinks and we took a seat in his living room, the sun setting on the city below us. He asked me questions about myself. I was shy and awkward per usual, but as time went on I could tell he had taken a genuine interest in me. It wasn't long before the topic of my gender identity came up.

"I... I'm trans. But I haven't come out yet. I really haven't ever told anyone. I don't know. I guess I'm not ready?" The truth was hard to say.

Dominic smiled. "Well you just came out to me. That's a big step." He got up from his chair and sat next to me on the couch. "So you're a girl. That's really exciting. You get to define a whole new persona. What should I call you from now on?" He looked deeply into my eyes, and for the first time, I felt like someone was actually seeing me for who I was.

"Chastity," I spoke with a burgeoning confidence. "My name is Chastity."

"Chastity... I like that name. Cheers." We touched glasses and finished our drinks. He took my glass and set them both down on the coffee table. He turned back to me and tucked my hair behind my ear. "Chastity," he said again. My name was like honey from his mouth.

I leaned forward and kissed him. My first kiss. He waited for a beat to make sure I wasn't going to pull away, and then he kissed me back. A deep passionate kiss, teaching my tongue to dance with his. I wanted him so badly.

After a couple minutes, he pulled away. "Come with me. I want to show you something." Dominic took my hand and led me down the hall to his bedroom. I took a seat on his bed and he disappeared into his walk in closet for a moment. He returned holding a set of lacy white lingerie. A bralette and a thong. "Put these on for me."

I stood up slowly and took the lingerie from Dominic with a sheepish smile. "Okay." I went to the bathroom and closed the door. I stripped down naked and watched myself in the mirror as I pulled up the lacy panties. They felt so good against my shaved legs. My small dick was already hard and leaking as I tucked it away inside the lace.

Next, I put the bralette on over my flat chest. I looked at myself in Dominic's mirror, turning to see my ass from different angles. My body was still skinny and boyish, but it was turning me on so much to see myself dressed as the girl I always knew I was.

I opened the door and saw Dominic standing in the middle of the room in only his black trunks. I could see his thick cock underneath stretched cotton of his underwear. He was already so hard for me. I swallowed hard.

Part of me wasn't ready for what was happening. But a deeper part of me wanted to worship Dominic's fat cock like the girls in the porn I liked to watch. He put his hand out for me and I walked towards him. I took his hand and he pulled me in close for a deep kiss. I could feel him pulsing against my flat tummy while he pressed his tongue against mine.

I felt him take my hands gently and guide them to his dick. It was so big, maybe 10 inches and very thick. I stroked it for him through his underwear while we kissed. It felt strange hold someone else's cock, especially one so heavy. Mine was barely 4 inches when hard. The weight of him in my hands made me feel powerful as I jacked him off slowly. Dominic groaned hungrily against my mouth as I worked him with both hands.

"Get on your knees, Chastity," Dominic commanded. I did like I was told and slid down his body, kneeling before my new master. He stroked my hair lovingly and leaned his hips forward, pressing his bulge against my face. "Breathe in deep. I want you to learn my scent." I did as I was told. It was intoxicating.

"Now take it out nice and slow," Again, I followed his instructions, freeing his cock from his underwear. I admired it in all its glory. My eyes looked back up for approval and his next command. "Kiss the tip."

"Yes Daddy," I said meekly and immediately felt him flex against my hand wrapped around his base. His eyes rolled back and I smirked. I found a kink. Dominic wanted to be my Daddy. I leaned forward and kissed around his crown. Soft kisses all over. Pre was leaking from the very tip. I tasted it with my tongue. His flavor was divine. I looked up at him again. "Can I suck it, Daddy?" I said innocently.

Dominic nodded and I smiled. I took his crown into my mouth and sucked on him gently. My tongue caressed the underside of his head, then circled around the edges of his fat tip while I stroked his shaft nice and slow. " Keep your eyes on me, baby." I looks up at him while I gave him my mouth. "Good girl," he whispered. His words made me leak in my panties.

He ran his fingers through my hair to the back of my head and made a fist. I pulled back and I looked up and him with a start. "Now spit. Spit right there." He pointed to his crown. I did as I was told and Daddy approved. "Very good, Chastity. From now on, when you suck my cock, I want you to spit all your drool right back onto it. You're not allowed to swallow until your mouth is full of my cum. Do you understand me?"

"Yes, Daddy. " My little clitty strained against the lace panties as Daddy began to train me, molding my submissive young mind. I went right back to work, sucking his fat tip. I relaxed my muscles and tried to work him deeper down my throat. I made it about halfway down his length before my eyes began to water. I gagged and thick drool escaped from the seal my lips made around him.

"Yes..." Daddy moaned his approval and pulled me off of him by my hair once more. My mouth was full of thick spit and it was leaking down my chin. I looked up at my Daddy and them back down as I decorated his cock with honey from my tonsils. "Very good, Chastity." And with that, he release his grip on my hair and put his hands behind his back. It felt like a sign of trust.

I used my drool to jack him off with both hands while I worked his massive cock deeper into my throat. Tears streamed down my face as I swallowed him over and over, pulling up more throat cum with every gag. I was making such a mess. Everything was slick with my drool. It was dripping down in long strands from Daddy's sack, my chin, and all down the front of my flat chest and tummy.

I looked up through tearful eyes and met my Daddy's adoring gaze. He was so pleased with me and for the first time in my life, I felt truly appreciated. It was time to return the favor. It was time to make my Daddy cum with my mouth. I refocused my sucking on Daddy's crown, my tongue massaging the underside of his tip. My hands picked up the pace, stroking his slick shaft up and down.

Daddy grunted his approved. He was getting close. I could feel him flexing against my tongue. I was hungry for his cum and he could tell. His thighs began to tremble and he let out a low sigh as he shot the first pulse of his orgasm into my mouth. I kept pumping my hands and sucking as Daddy fed me his warm seed. I opened my mouth so he could watch it fill with pearly white sperm. I milked out every last drop.

Daddy looked down at his mess. My tongue playing in his thick load as I showed off my reward with smiling eyes. Daddy's cum tasted strong, a mix of salt and sweet that I couldn't help but savor. "Chastity, you're such a good girl," His voice was warm with admiration and approval. "Now swallow." He commanded.

I obeyed. It took several gulps to get all of his cum down into my tummy, but when I was done I opened my mouth to show Daddy how well I follow directions. "Thank you Daddy." I beamed up at him with a big bright smile. I don't know if I've ever smiled that big and genuine in my entire life.

Dominic reached down, pulled me to my feet and kissed deeply. He took my hand and walked me to the bathroom. I saw myself in the mirror, covered in shiny drool and sweat. My hair was a mess. Standing there in the lacy white lingerie, I looked like one of the countless girls I fantasized about being in the porn I watched. He kissed my neck softly, nibbling and whispered, "Do you see yourself, Chastity? Do you see the real you? You're so beautiful." His love made my head spin. This felt like a dream.

Dominic used a hand towel to clean me off and then wrapped his strong arms around me and stood there with me while I admired myself in the mirror. I reached up and held onto his forearms with both hands. "Thank you so much, Dominic. That was incredible."

He kissed the back of my head. "Come on Chastity. Let's go to bed."