Transition Pt. 01

Graduate school was starting in a month and my nineteenth birthday would occur just before then. I was a bookworm. A tall, skinny, pretty boy with a fantastic memory and a confused heart.

My Mom named me Riley and I began walking and talking earlier than most. I loved playing in my mom's closet and dresser drawers. Her clothes were colourful and soft, her perfume was like a mountain mist and her jewellery sparkled like a pirate's treasure.

When mom and I were alone, we would build a magical world that made me feel welcome. When my dad was home, that part of me was denied. In clothing stores, I was attracted to pinks and purples, only to leave with greys and blues.

I wanted my ears pierced like mom, but she said dad would not approve and not to even consider asking him. I lived in two worlds. One with mom and the other with dad.

A few years before puberty I asked mom if the hospital would cut off my penis and leave me with a vagina. That was the day we had a family meeting and dad learned I wanted to be a girl.

He thought I was gay with a fetish for female clothing and struggled with his biases and his concern for me. As puberty approached, my sexual interest was clearly in boys. I would go camping with my guy friends and I developed a huge crush on Mark.

The first time I saw him naked was at the lake. We dared each other to go skinny dipping and his broad shoulders thrilled me as much as his rounded bottom. I would have welcomed a kiss, but all I got was ... "What are you looking at, fag."

I delved into books and study. I was not a part of my guy friend's world and not accepted into the girl's world. Only with my mom did I feel like myself. She taught me all about fashion and makeup and to believe that happiness would come.

Dad would attend my school events and beamed with pride at my pins, badges and trophies. Unfortunately, the more I needed his hugs, the more he pulled away.

Mornings became the worst. Waking up with a hard penis reminded me of how much I didn't want it. Even worse was the day I learned about masturbation. I heard guys talking about jerking off and naming a few girls that had done that to them.

I masturbated that night and my body shook in magical bliss. Nothing came out and I was thrilled with the tingles that had shook my body.. Maybe I wasn't totally a boy. My mom and I talked about sex and she told me that eventually that would change and dry orgasms would lead to wet ones. I knew about sperm production and the prostate and I told mom that maybe I didn't have one.

A few months later that belief was shattered. I was laying on my bed, eyes closed with hand moving up and down. Although I hated my penis, I loved the pleasure it gave me. I imagined how it must feel for mom to have dad inside her. How wonderful to be held and share an orgasm. The head of my penis expanded and the glorious anticipation took my breath away. In a flash I was crushed as gobs of wetness landed on my neck, chest and tummy. Yuck!!

But, curiosity took over and I touched it with my fingers. Part repulsed and part aroused, l licked some off my fingertips. I did this over and over until there was no more left. None left, except for a pearly drop at my pee slit.

I was about to swipe my finger over it when a thought occurred. I shifted and stretched, moving one way and then the next, bent far enough to lick the drop and slide my lips over my cock-head

Gentle laps with my tongue and pressure with my lips soon made me tingle and suddenly spurts of wetness splashed into my mouth. The first cock I sucked was my own.

Guys would brag about hand jobs and some swore they got blow jobs as well. I swore on my grandmother's grave that I had gotten a blow job and I thought I would become one of the guys.

My one time crush, Mark laughed. "And who was the guy that sucked you?"

Punching him may have been the guy reaction, but before I could turn and run, one tear led to another.

"Did you suck him back?" All his friends laughed.

This encouraged him more. "You probably want to suck me."

I ran home and cried on my bed. Two nights earlier I had masturbated with those exact thoughts.

Soon after I saw a girl in the lunch room that kept to herself, but had always caught my eye. I sat with her and over the next week we became inseparable. She was a closeted lesbian and the first person, other than my mother, that thought of me as a female.

Our first kiss came at the top of a Ferris wheel. We had had a magnificent time all day and she just leaned into me a pressed her lips to mine. She slipped her tongue into my mouth and my panties became wet with precum. Our tongues twirled and our moans harmonized in a hot duet.

"Are you wet too," she asked.

I laughed and nodded yes.

"That's the last time I let you borrow my panties and then kiss you."

"I hope that's not our last kiss," I said.

"Definitely not," she replied.

The wheel stayed still for five minutes and we kissed the time away.

Our physical lovemaking didn't progress much beyond kissing. We masturbated each other once and even tried oral. She didn't like cock and I didn't like pussy, but we did love each other.

Dad was thrilled. He didn't know what I was, but seeing us kiss and hold hands made his world seem right. Months later, he was diagnosed with cancer and before summer's end, he was gone.

Between Christmas and New Years, mom had driven to her sisters and a drunk driver had sped through a red light and smashed her life away.

If not for Leah, I would not have survived.

Dad had left a life insurance policy and so had mom. There was more than enough money for my education and living expenses and lots left over for a transition.

Part 2 to Follow.