From then on, we became more like best friends than siblings, telling each other everything, sharing secrets, keeping inside jokes and covering for each other when we broke rules. I was always to afraid to tell her how I felt about her, as I didn't want to ruin our newfound friendship, and this continued up until the day that she took me aside because she had something really important to get off her chest. We sat on her bed and I held her as she told me that she was in love with her friend, Katie, and that she thought that she was a lesbian. I was surprised, of course, but mostly just saddened to know that she would never love me as I loved her.
Time, I think, to give some background. My name is Bryan, and I was 16 at the time of these events. I lived in a friendly suburb of a big city in Australia with my mother and my sister. My mother was a director of a large company, and was often away for two or three days a week at events or conferences. This left us pretty much to our own devices. For fun, I liked to listen to music and I swam casually at the beach, but that was as far as my athletic abilities went. I was very thin and quite small; not muscular but without much fat either. I had shoulder-length brown hair that I normally kept in a ponytail – an homage to some of my favorite rock bands.
My sister Sophie was a year older than me, and while I attended a public school, she had received a hockey scholarship to an all-girls school. She was about an inch taller than me at 5'5”, very fit, and had short brown hair. She had an incredible figure, which, I must admit, I frequently lusted over. She look very natural and had a flat stomach and gorgeous 32B breasts.
A few weeks passed and ,while I felt privileged to know my sister's secret, it left me tormented inside, to the point where I became very withdrawn. I started eating a lot less and focusing less on schoolwork. Things came to a head one weekend, when my mother was out of town. I decided to “celebrate” failing a maths test, by retreating to my room with a bottle of vodka. Things were made worse by the fact that my sister was having Katie over and was planning on telling her how she felt. I heard them come in, but, half the bottle already in me, I fell asleep shortly after.
I was awakened a while later as something sat on my bed. I looked up to see my sister looking at me. “Sorry,” she said, “I didn't mean to wake you.” “That's okay” I groaned, rubbing my eyes. “How did things go with Katie?” With that, she looked a little saddened, and I sat up and hugged her. “I'm so sorry,” I whispered, “was she weirded out or was it okay?” “It was okay, she just didn't feel the same, but she said she'd keep it a secret.” Maybe it was the alcohol talking but I felt like I had to say something, vodka-fueled though it might be. Maybe in the morning I could claim I was still drunk. “I would've been happy to be in her shoes,” I whispered, almost to myself, “You're smart and kind and sexy. She's a fool not to want you.” I felt Sophie tense as I spoke, and she sat up and looked at me. “You really feel like that?” she croaked, tears welling up in her eyes. “Of course I do!” I said, knowing all the while that I was digging a deeper hole. “I've loved you for so long. It just hurts to know that you won't love me the same way.” “Oh Bryan,” she sighed, “Of course I love you. You are so kind and caring. Just because I'm attracted to girls doesn't mean I don't love you. There's a difference between being in love with someone and wanting a physical relationship with them. I just need someone who can do both for me.” “Yeah, I guess,” I muttered, “But I do want that. Sometimes I wish I could become a girl. Maybe then you'd think of me like that.” With that, she leaned in and kissed me. I was quite taken aback, but soon started to reciprocate. Eventually, she broke away. “I know you would,” she whispered, “That's why I love you. Why don't I show you what I'm willing to do for you?”
She began to move toward the end of the bed and moved to unbuckle my pants. “But, I thought you don't-” I said, before she cut me off. “This is for you, to show you how much I love you. This is just a one-off thing. Just because I don't like guys, doesn't mean I won't enjoy making you, and only you, feel good.” She slowly pulled down my trousers, to reveal my penis already fully erect in my boxer shorts. She quickly removed those, and proceeded to wrap her fingers around my shaft. As she started to stroke up and down, a bead of pre-cum appeared on the tip. She lowered her head and stuck out her tongue, slowly licking it up. She looked up at me then, and began to lower her mouth over the head of my penis. The sensation was electric as she sucked gently, drawing me further into her mouth. She then started to bob up and down as the pleasure mounted. I tried to hold off as long as I could, but eventually I had to signal to her that I was about to explode. She pulled me in as deep as she could as a wave of pleasure ran through my body and I came deep in her mouth. She slowly removed me from her lips and, my cum still in her mouth, she moved up and kissed me, forcing her tongue into my mouth so that I could taste myself on her tongue. She broke the kiss and then swallowed, nestling up against me. She whispered one last “I love you.” before we both fell asleep.
The next morning I awakened surprisingly fresh, with the details of the previous night fresh in my mind. My whole being wanted to repay the favor, but I remembered her insistence that it was a one-off, and I didn't want to ruin anything by making her uncomfortable. I turned to see that Sophie had left the bed at some point during the night. I walked downstairs to find her in the kitchen making breakfast. I greeted her as I went in, but she turned away and didn't say anything. After a minute, she turned back to me, asking if I remembered the conversation the previous night. “You said last night that you would like to be a girl, so that I would be attracted to you. Did you mean that?” “Of course,” I said, “I love you so much, and I'd love to show you how much, like you did for me.” “After last night, I went back to my bed, but all I could think about was those words, and the thought of making you into a girl. I must that the thought got me a little worked up...” she said quietly, looking at the floor as she spoke. “Would you be willing to let me experiment with you today? It'll just be the two of us and I promise I'll make it up to you.” It was hard to refuse, after what she had done for me, against her tendencies, so I agreed, wondering at how bad it could be. As soon as I agreed, she looked up at me beaming and ran upstairs telling me to come up to the master bathroom in five minutes.
Five minutes later, I slowly made my way upstairs, wondering at what was in store. I entered the bathroom to see my sister sitting on the edge of the bath with a robe on. She had the shower running and directed me inside. Despite the events of the previous night, it felt strange getting naked in front of her, but I quickly stripped down and entered the shower. She then dropped her robe to the ground as I stared at her, mouth agape. She was completely naked from head to toe, showing off her toned body. She was completely hairless from the neck down and my eyes were instantly drawn to her smooth pussy. “Now, now,” she laughed, grinning at my wide-eyed stare, “this day is for my enjoyment, not yours!” She then grabbed a razor from a cabinet and entered the shower with me. At the sight of the water flowing over her breasts, I was willing to agree to anything, so I agreed when she asked if she could shave me. It was a strange sensation, feeling the razor run over my legs and armpits but as I left the shower, I found myself enjoying the look of them in the mirror. With my small feet, they could easily pass as a girls legs. I became a little worried as Sophie told me to spread my legs. She took a can of shaving cream and applied it liberally to my balls and the base of my penis and I stayed frozen still as she began to slowly drag the razor over the skin, leaving it smooth and bare, before turning me around and doing the same to my ass. She then took a tube of moisturizer and, telling me I'll enjoy the next part, started to rub it in everywhere she shaved, including my tender balls and the length of my shaft. I thought briefly that I might get lucky, but it ended as soon as it started, however she seemed to spend a lot of extra time on my ass which surprisingly felt quite nice.
Following this, she led me to her bedroom. I was surprised when I looked in her full-length mirror, that with my penis flaccid at the time, I looked very feminine. That was the point, and there was no permanent changes, but I was a little worried that I was liking the view. While I was admiring, Sophie was rummaging through her closet, and she returned clothed, and with a handful of clothes of all different colors and styles. “Here, put these on.” she said, handing me a black lace thong, tied at the sides with ribbon bows.
