Samantha's Journey

By Samantha T

Published on Jan 4, 2025

Transgender

This is a continuing true story of my journey as a young trans girl.

No one was injured in the writing of this story.

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Hello. I was born a Samuel, and now I go by Samantha or Sam to make things easier for my friends.

For anyone that hasn't read the first two parts of my story, I encourage you to take a look at them.

I have been living at my best friend Greg's house for three weeks now. Every day, I was dressed as and lived life as a girl. His entire family accepted me, even Greg's father who was in the military.

Beverly, Greg's mom, was especially encouraging to me. She would take me shopping for clothes, shoes and even to the sex toy store!! She told me she was excited to have a girl to dress up, which turned her on.

I was becoming more and more confident about going out dressed as a girl. When I would go out with Beverly and Greg, they would introduce me as their cousin from out of state, and even when I did know the person, they didn't seem to recognize me or put it together.

Greg was surprisingly cool with me dressing up as a girl, even though we were best friends since we were six years old. We never talked about it in any great deal, but he didn't treat me any differently.

One day, I went to his room looking for him. He wasn't there, but I saw that there were pictures of transsexual girls on his computer. I moved a little closer to get a better look. I reached down and rubbed my cock, which was already hard. I decided to leave before Greg got back. I turned to go, but Greg was already there.

"Sorry, I didn't mean to invade your privacy," I apologized.

"No, it's okay. I guess I should explain," Greg said as he walked into the room.

"You don't need to at all," I told him.

"No, I do," he explained, "I wanted to find out more about you, to try to understand better."

Greg continued. "The more I looked and read, the more I was fascinated and turned on."

I was stunned at this revelation.

"It's not all about sex and porn, though," I explained.

"I know there are great resource sites that were very helpful to me," he told me.

"Great, thanks for doing that," I told him.

"I have questions, though, is that okay?" Greg asked.

"Yes, ask me anything at all," I said.

For the next hour, Greg quizzed me. They started slowly and easily, then became more explicit and direct. Including: What position I like? Can I get an erection? Do I like men or women better?

I answered every question he had wholly and honestly. It was a great bonding experience. We were both incredibly turned on as well. Greg asked if he could see me in my lingerie. So I did a little striptease for him. I slowly pulled off my sweater over my head. I bent over at the waist and pulled down my pants. I turned toward him with just my bra and panties on. My erection wasn't being hidden by my panties much.

"You look very sexy," Greg told me unexpectedly.

I thanked him and without thinking, put my hand on my cock and started rubbing it. Greg watched me stroking my cock for a minute before he took out his cock. I had not seen his cock since we were kids. Greg had a nine-inch uncircumcised cock, and it was fully erect. We watched each other as we stroked our cocks. It was quite a turn-on.

"Have you ever sucked on a cock before?" Greg blurted out.

"No, but I want to," I answered quickly.

Greg pushed his large cock toward me as if to offer it up to me. I smiled and then knelt between his legs. I looked up at him, then grabbed the base of his cock with my hand and pulled his foreskin down. I put my mouth over his cock head and slid it into my mouth. He moaned as I took him into my mouth.

I stroked my cock as I sucked on Greg's hard cock. I licked its sides and took it as deeply in my mouth as I could without gagging. After about fifteen minutes of me praying over his glorious member, he announced he was going to cum.

"Cum on my face," I told him breathlessly.

Greg pulled out his cock and stroked it over my face and awaiting mouth. He grunted and then shot his hot load all over my face! He came a lot, and my face was covered. This was my first facial of many! I took a lot of his cum from my face and ate it. This seemed to turn Greg on as he was mesmerized.

"Your turn," Greg told me.

I was shocked at this and wondered what he meant. He told me to get on the bed, and he took my seven-and-a-half-inch cock in his hand and he proceeded to jerk me off. It wasn't a blowjob, but enjoyable, just the same. I lifted my painted toes in the air and pushed my fingers in my asshole while he stroked. I told him I was cumming, and he stroked me faster. My hot cum blasted out of my cock, up to my stomach, chest, and onto my chin as well. I smiled at Greg after my orgasm subsided. I leaned over and licked my cum from his hand. It was a special moment between two friends.

We had similar nights like that over the years, but it never progressed beyond blowjobs and handjobs.

Beverly, Greg's mother, was the person that I trusted the most in the entire world. She was the first to encourage me and support me. When we became occasional secret lovers, we became even closer. Beverly was a stunning woman. She had long black hair, beautiful green eyes, and a perfect smile. Her skin was a golden brown from her Apache--African American heritage. Her petite five-foot--six-inch frame was perfectly proportioned with her pert, supple breasts.

Beverly asked me always to be open and honest with her, and I still have been. So when Greg and I started having sex, I told her. Surprisingly, she was supportive but also a bit jealous. She was happy that Greg and I could share these things as long as it didn't affect our friendship.

Beverly loved to hear about my online relationships as well and was often in the room as I chatted with them. When I explained my strong feelings for Max, she was cautiously supportive as well. He was much older than me, but I had a connection with him.

Max, or as I called him, Daddy Max, told me he was coming to my city and wanted to meet up with me. We had been chatting for eight months, and finally, we would meet! I was so excited!

Next: Chapter 4


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