Rachael Ch. 02: School Years

CHAPTER 2

School Years

Dad was killed in an automobile accident in July, a drunk driver hit him as he went thru a green light and the other driver ran a red light. He died instantly as the truck hit him in the driver's door. Life with my prudish mother was going to be a lot different. I was still off the male hormones and my body was developing more like a girl than a boy. The doctor tested my female hormones and they were off the chart. My body was telling everybody I was a girl.

Mom didn't understand and didn't want to understand, so I avoided the talk with her. The loss of my dad was difficult for her and she turned away from me and into herself and her prudish ways.

That school year was brutal for me. I dressed like a boy but felt like a girl. Confusion is only a word, what I was living was a nightmare.

Dad had left me some insurance money and I started to explore the world of boarding schools. I found a boarding school several hundred miles away that was for girls only and I made an application to attend. The major thing for the school was could I pay the tuition. I could, thanks to Dad, so they let me in as a girl, not knowing any different. I got a new wardrobe of girlish uniforms and started classes in the fall.

The new school was great for me, I studied, I got great grades and I didn't have to deal with the boy/girl issue at all. I kept to myself, didn't let anyone see my penis and started working on my breast growth. When I talked to the doctor about what I wanted to do he switched my hormones to estrogen and that helped everything. I was becoming a woman and I loved every minute of it. I graduated from the school three years later with honors and was accepted at a nearby university. My education was going to continue but soon I realized that I needed some other schooling as well.

The Senior Prom at our little girl's school on the river was a big deal. When I was a junior, I worked on the prom, so the seniors would have a good time without all the hassles of making it happen. When I was a senior, I wasn't sure what to do about a date. I had never really dated a boy or had a prom dress either for that matter. I had been out with some of the girls when they had boyfriends come to town, mostly as "the other girl." Once or twice they brought somebody for me to talk to. I even got kissed once. That was okay, and I made sure things didn't get too far. I did not want to be discovered.

One my roommates insisted that she bring her brother to the prom for me as my date. She showed me pictures of him, talked about him to the point I suggested she should take him not me. That didn't work out so well, she got pissed but we made up and I agreed to go with him. They had to drive a couple of hours to get to our school and they would come together, her boyfriend and her brother.

I figured out a few things to help me hide my manhood. I learned that the testicles could go back up into the cavity they came out of and you could put your penis over them between your legs and hold the whole thing in with a feminine pad. Double protection. This looked pretty good in my non-sexy full panties, in white cotton of course. My breasts had filled out to a nice B cup so that was handled.

The dress was going to be a little difficult until one of my classmates revealed that her mother was a dress maker and that for the mere sum of one hundred dollars, I could have my very own prom dress. I of course came up with the cash from my insurance stash and picked out something from a catalogue. Measurements were taken, and everything was set. The big weekend arrived, and I was nervous as hell.

My date was charming, and we danced a lot, drank punch and even walked outside a time or two to experience the night air on the river. The setting was beautiful, and the juniors had done a remarkable job with the decorations. My date held my hand for a while as we walked and was a perfect gentleman.

After the last dance his sister and her boyfriend disappeared, and we really couldn't find them. My date wanted to head home, it was late, and they were traveling together. We walked the banks of the river, talked about lots of things and at some point, he backed me against a tree and kissed me. I liked the way he kissed and responded to him by holding on and pressing my breasts against him. He liked that too. I didn't like having my back to this big old tree, but I didn't want to disturb the really good kissing that was going on. He brought a hand up and cupped my breast at one point and that felt pretty good, so I let him fondle both of them. He reached inside and found my nipple. I pulled a shoulder strap down and exposed it to him, so he could suck on it and away he went.

He really was being a perfect gentleman until I felt a hand reach down and start to gather my dress for a leg assault. The dress was long, and he had to gather it up before he could feel what he wanted to feel. I responded by picking his head up off my nipple and kissing him some more. He lost his reach for the dress hem and I pressed hard up against him. To say he had a hard on would be an understatement and he pressed it against me as hard as he could. I slipped a knee between his legs and let him hump on it a little. He seemed satisfied for a while and we continued kissing there against the tree.

I was having a ball, no pun intended, and he was starting to stress out. I could tell his dick was in control and he wanted me to give it up, let him pull my panties down and stick it in me. That wasn't going to happen. He moaned and bitched about how much it hurt, and he needed to fuck me to relieve the pain and pressure. Too bad. I knew better. But he had been nice to me all night and I felt he deserved something.

I reached down and felt his erection and worked my fingers into his zipper. I pulled the zipper down and reached into his tighty whities and pulled him out. Now I had him exposed and could squeeze him and roll his foreskin up and over the head, back and forth, sending him into even more frenzy. To his credit again, he didn't push, he asked and begged, but he didn't push. He stopped bitching when I got a good grip on him and started to give him a good stroke. He stopped kissing me and I stopped stroking him. That kind of confused him until I reached up with the other hand and pulled his face to me, he kissed me again and I stroked again. I guess he got the message.

I had not sucked a boy's dick, so I prepared myself for the initial try. I was about to go to my knees for him when he got very animated and tried to pull away. I had a pretty good grip on him, and he froze in place.

"I'm gonna cum," he said.

I stopped stroking him and just held him steady for a bit and I thought he was going to relax, suddenly he convulsed, and I felt the hot wet sticky juice in my hand. I had waited too long. It was probably for the better. I retrieved his hanky from his jacket pocket and cleaned him up as best I could, I wanted to lick it but resisted. Not the time or place really. That's when I got my first lesson in men.

He put it away, zipped up and said, "I really have to get going." Little did I know how often I would hear those words in my future? Yes, he took my arm as we walked to the car and he was still charming. His sister was in the back seat with her feet against the window. We got there in time to watch them finish and the two boys left in a distinct hurry. I am sure they had a wonderful conversation on the way home. My roommate and I wandered back to the dorms and she told me all about her first time. She was surprised that I didn't get laid, acted skeptical even. I told her that it didn't happen. I guess he didn't like me enough was the way I left it. I never heard from him again, but then again, I was off to the university before I had time to worry about boys. I knew I was a woman now. I knew I could get men when I wanted. I just needed to learn more about how to deal with them when I got one. Ha Ha.