The Odyssey of a Transgirl Pt. 03

If you haven't read the first two chapters of my story I encourage you to do so.

I went from the greatest living situation, having sex with two beautiful women, to being homeless and having absolutely nothing, in the blink of an eye.

I called the only person I trusted and who would understand me: my best friend's mother, Beverly.

I told her the entire story; she said I could stay with her as long as I wanted, and she would come and get me.

I stood outside the bus station with my suitcase, looking pathetic, when Beverly pulled up in her SUV.

She walked over and gave me a warm, comforting hug.

"It will be alright." She assured me.

We arrived at her house just after dinner.

My best friend, Greg, came up to greet me.

"Mom said you got kicked out of your place," Greg said.

I hesitated with my answer until Beverly spoke up for me.

"Yes," I answered unsurely.

"Greg, take Sam down to my craft room, that is where Sam will stay," Beverly told Greg and added. "For as long as you want, Sam, okay?"

"Okay," I told her and smiled.

Later that night, I was getting things ready in my new room, sitting on the day bed when Beverly knocked and came in.

"Getting settled in?" She asked.

"Yes. Thank you so much for everything. "I told Beverly.

"No problem, Sam.' She answered.

"I've decided on Samantha," I told her.

"Beautiful name," she said, smiling.

Beverly hugged me lovingly.

"What have you told Greg about me being...?" I asked.

"About you being trans? No," she said. "I think that would be best coming from you."

"What if he hates me afterward?" I asked.

"You need to trust him as a friend. He is a good person. I am sure he will understand," Beverly explained.

"Okay." Was all I could muster.

"Everything will be alright in the morning." Beverly comforted me.

"Now lie down and get some sleep, you must be exhausted."

She tucked me under the covers and then gave me a not-so-motherly lingering kiss on the lips.

She stared at me, conflicted, until she turned to the door.

"I will be strong. Good night." She said as she closed the door.

I fell asleep right away.

The next day, everything was so much better. Greg and I hung out and played video games for hours. Although weighing heavily on my mind was how to tell Greg about me dressing in women's clothes and being trans.

I talked it over with Beverly, and we decided it was best just to show him. So, after dinner, Beverly helped me get dressed and do my makeup and hair. After we were done, I looked in the mirror, and I had to admit I looked great.

I followed Beverly into the family room where Greg was on his phone.

"Greg, Sam has something to tell you," Beverly announced.

Greg looked up as I stepped out from behind Beverly.

Greg didn't recognize me at first, but then the realization hit.

"What the fuck?" Was his first response.

I immediately had a fight-or-flight response. I decided to fight.

"I'm trans," I stated.

"I don't get it?" Greg said, confused.

I looked back at Beverly.

"I will let you two figure this out. Call if you need me." Beverly said as she left the room.

"I like dressing as a girl. I am a girl. That's why I got kicked out," I explained.

"Are you a girl or just like to dress like a girl?" Greg asked.

"Both, I guess," I answered.

"This is a lot," Greg said.

"I know, I'm just trying to figure it all out as well." Pausing to take a deep breath, I said, "I hope you are okay with this."

Greg paused for what felt like an eternity and finally spoke.

"Yeah, I'm okay. It's just going to take a bit." Greg said.

"I understand," I said.

"What do I call you?" he asked, the thought just popping up.

"Samantha or Sam," I told him.

"Well, that's convenient. I like Samantha," Greg said, smiling.

A few minutes of awkward silence passed before Greg spoke again.

"Fortnite?" Was all Greg had to say.

"Yes!" was my quick and happy response.

The rest of the night was the same as before, good friends having fun. Just this time I was wearing a blouse and skirt. I was so relieved and happy!

At the end of the night, I happily bounced back to my room. I opened the door to find Beverly naked on my bed, playing with her pussy. I closed the door behind me.

"I am so sorry, Samantha. I tried to control it, but I need you to fuck me!" Beverly said lustfully.

I pulled down my skirt, opened my blouse, and moved quickly to the bed.

Beverly reached and put her arms around my waist.

She kissed my stomach and trailed her kisses down to my panty-covered cock.

She pulled down the waistband of my panties, exposing my very hard shaved cock.

Beverly smiled up at me and then took my cock into her mouth!

Beverly expertly sucked on me, taking me deep into her mouth with ease. It was the most amazing feeling of my young life. Then, Beverly fell back on the bed and spread her legs.

"Fuck me right now, Samantha!" Beverly urged.

I took my cock to the opening of her very wet pussy and quickly pushed it in. She moaned as I entered her. I began to piston my cock into her. The rhythm between us was almost instant.

Beverly spread her legs and grabbed her feet above her head.

"Give it to me, Samantha! Fuck me!" Beverly cried out.

I started to pound her even faster. She began to moan even louder.

"Fuck, Coming!" She announced.

Beverly started to spasm violently. It was like she was possessed. She came for almost a minute before regaining control.

This was too much for me, and I told her I was going to cum.

"Cum inside me. It's alright." She told me breathlessly.

A few more strokes and I was shooting my hot load into this beautiful woman's pussy. The best orgasm of my life.

We lay together in each other's arms before she got up to get dressed.

"Samantha, I am happy you are here. This won't be a regular thing, okay?" Beverly told me.

"Okay," I answered.

Beverly closed the door, and I drifted off to sleep.

Things were indeed going to get better.

I have been living at my best friend Greg's house for three weeks now.

Every day, I dressed as a girl and lived life as one. His entire family accepted me, even Greg's father, who was in the military.

Beverly, Greg's mom, was especially encouraging. 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 went out with Beverly and Greg, they introduced me as their cousin from out of state, and even though 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 much, 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 as he got comfortable.

Including:

"Are you a top or a bottom?"

"Bottom, I think, not sure, I am pretty passive, but can be forward at times," I answered.

"Do you like men or women better?"

"Both. I am very turned on by both sexes," I said honestly.

Then I told him about Max, Sarah Jane, and Ruby Mae.

It was great to tell someone.

He was astonished and grinning.

Then a revelation.

"I think I might be bisexual, too," Greg confessed.

I was gobsmacked.

"Jees, you think you know a guy," I said sarcastically.

We both laughed. More ice broken.

"Do you get erections?" Greg asked bluntly.

"Yes. I have one now," I said, blushing.

"I do too," Greg stated, "Raging hard-on, actually."

I looked down and saw the tent growing in his sweatpants.

"I can see that," I chuckled.

I answered every question he had wholly and honestly.

It was a great bonding experience. We were both incredibly turned on.

"Are you wearing anything underneath your skirt?" He asked cautiously.

"Yes, panties," I said," Would you like to see?"

"Yes," Greg said breathlessly.

Smiling, 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 skirt.

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.

Then I let my panties drop to my ankles and started stroking my seven and a half -inch circumcised cock.

Greg watched me, intently stroking my cock for a few minutes before he took out his cock.

I had never seen his cock before. Greg had a monster nine-inch uncircumcised cock, and it was rock hard.

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, looking up at him, then grabbed the base of his cock with my hand and pulled his foreskin back.

I put my mouth over his cock head and slid it into my mouth. Licking it like a large ice cream cone.

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 of many facial sessions! I took a lot of his sicky cum from my face and licked it off my fingers. It seemed to turn Greg on.

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.

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 frame was perfectly proportioned with her pert, supple breasts.

Beverly always asked me to be open and honest with her, and I always have been.

So, when Greg and I started having sex, I told her.

Surprisingly, she was supportive but also a bit jealous that I had another lover.

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.

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!