This story contains explicit sex between high-school aged brothers, with one of the brothers dressing and presenting as a girl. If you'd rather not read this, then don't. (Incest, transgender, gay, bisexual)
Ever since I was twelve, I knew I was different. The other boys would joke about the girls and their newly discovered periods as if it was the funniest thing they would imagine, yet still strangely drawn to the idea. I, on the other hand, was wondering what it would be like to have one myself. Sometimes I felt like I wanted to be a girl, but I had no idea how that could be possible. A couple of the boys had kissed girls, and I knew from those gossiped conversations and from television and movies that boys were supposed to kiss girls. But it was never something I was interested in. In fact, I not only wasn't interested in kissing girls, but I was interested in kissing a particular boy.
It was my brother, Jake.
Jake was a year younger than me, and when he turned eleven, I decided that I had to do something about my infatuation with him. At the time we shared a room, and so late that night, probably about eleven o'clock, I went over to his bed and leaned over him, one arm on his other side.
He was beautiful. He had golden locks, unlike my brown ones, and they were wavy down the sides of his face. He was shirtless, as he always was when he slept, and I placed one hand on his chest.
"Jake," I said. He stirred a little bit. I leaned a little closer. "Jake..."
He opened his eyes sleepily and said, "Awe what is it, Andy?" It was then that he looked down to see my hand on his chest.
"I wanted to give you your birthday present from me," I said to him, and fingering away a couple of loose strands of my long straight hair, I leaned down to his lips. Gently, I pressed my lips to his, basking in the wonder of my first kiss.
I pulled away and surveyed his expression. It was the same sleepy look I had found upon waking him. No--there was something different. His eyes were glazed. He was starting to cry.
"Is there something wrong?" I asked him. I prayed to God there wasn't.
He smiled. That smile. "No," he said. "It's just I like to kiss you." He threw an arm around my neck and pulled me back, and we kissed again. We kissed for about a half-hour before we decided we should go to sleep.
-=-=-=-=-
My dream would have been to grow up lovers with my brother, but as time progressed, he grew more attracted to the girls he went to school with. I found myself still attracted to boys, but there was always something that drew me back to Jake, despite his growing away from me.
For my sixteenth birthday, my friend Julie, who had seen how I had shaven everything all over my body, bought for me a waxing kit. Julie was the only one at school who knew I was gay. Incidentally I was the only one at school who knew she was a lesbian. We were best friends, and it worked well for us, since we could tell each other about anything that happened in our lives.
After my sixteenth birthday, I started using the money I had been saving from working down at our local youth center as a counsellor to make some big purchases. I always wanted to know what it was like to be a woman, even when I was very young, so I bought a selection of skirts, tops, and makeup. I figured that my own hair was long enough, being very straight and shoulder-length, that I could do anything I wanted with it and have no need for a wig.
One day Julie was helping me dress up as a woman. As I placed the three-inch black pumps over my fishnet-covered feet and stood up, running my hands over my black skirt. I walked over to the mirror and, looking at the beautiful woman I was, said to Julie (who was sitting on my bed), "I want to have sex with Jake."
There was a pause. I continued to look at myself in the mirror, disregarding Julia behind me. I watched her rise behind me and approach, embracing me from behind.
I had taken a leap of faith, and she was trying to accept me. A tear came to my eye. "Thank you," I said. it was all I could say.
"It's all right, Andy. But can I ask you a question?"
"All right."
"Have you two ever done anything before?"
"When we were little. We kissed and stuff."
"Why this big step now? You know that he's straight. Well, and he's your brother."
I shook my head. "I don't know, Julie. It's just that he... I want him. And something inside me tells me that he wants me too."
Julie was quiet for a moment, then I heard her sniffle. Then she said, "Let's get a look at you, you fine woman." She spun me around and I saw a smile on her face. "God, Andy. You're gorgeous."
I beamed at her. I had confidence in my appearance. It wouldn't be something I would necessarily like to wear in public, but it made me feel good. Very good. Like it was my true self. I felt more like a woman then than I had ever felt a man.
Julie stopped checking me out and looked up at my eyes, her eyes widened.
"I think I have an idea, Andy."
-=-=-=-=-
Julie's idea was brilliant. Since Jake seemed straight, I would present myself as a woman to him, but still his brother. Perhaps my appearance would turn him on; Julie had said that when I dressed as a woman it certainly turned her on. That made me even more sure that the plan would work. Now I only needed to decide a time.
I waited until it was a Saturday night and my parents had gone out with friends drinking. It would be just Jake and I that night. I spent about an hour prettying myself up, and waited in my room until I heard Jake's shower turn off. I took a deep breath and walked down the hall to his door. I knocked lightly and called for him. After a second, I heard him tell me to come in. I took another deep breath and turned the knob.
I saw him lying on his bed in his boxer shorts, which clung to his lean, slightly moist body. He was reading some magazine, and hadn't looked up to see me yet. I walked sexily over to the bed and took a seat on the edge.
"Jake."
He looked at me, and his eyes got wide. He spun around his legs and sat beside me on the bed.
His voice was trembling. "Andy, what's..."
My voice was trembling too. "Jake, do you remember when we used to kiss and touch each other when we were younger?"
He was silent. He was too busy checking me out. "YES," I thought.
I reached over to him and placed my arms around his waist. He put up no resistance. Not physically anyway.
"Andy, what are you doing?"
"Kissing you. What's so wrong with that? We've done it hundreds of times." I leaned in for the kiss. I kissed him. I pulled away from the kiss. I was euphoric with the flood of memories, and with the feeling of kissing the object of my desire for years. I noticed that my freshly applied lipstick left a slight residue on his lips where I had shown him my love.
Jake didn't move at first. But then he took the back of my head with his hand and pulled me in for a second kiss. This one lasted longer. Much longer. He even opened his mouth and put is tongue in mine. I sucked on it playfully before continuing to kiss him. I placed one hand on his thigh and felt his boxers moving slightly. With a quick glance between kisses, I saw him getting hard. This was my dream come true. I took my hand and rubbed it over his hardening cock until he was completely erect. I pulled his dick through the hole in his boxers and began to jack him off while kissing him.
He reached over to try to touch where my cock would be, but I pushed his hand away. Grabbing his hair and pulling his head away, I said, "I don't have one tonight." He let out a breath of air and pulled my head in again.
I broke the kiss, noticing the lipstick on his face, and smiling I leaned down into his lap. Licking once from his balls to the head, I encircled my lips around his engorged member. I could hear him exhaling with relief of the sexual tension that I had caused--that I had caused! I was in ecstasy as I dove down around his cock, taking it as far as my throat would allow without completely gagging me. My tongue was swirling all around him, tasting what I had longed to taste for so long.
As I pulled off to look at his face, I continued to jack him off with my hand. I leaned in and kissed his beautiful face.
"Jake?"
"Yeah?" he managed to say.
"I want you to take me."
He paused for a moment, as if questioning within himself whether he should or not. A pang of fear entered into my mind. What if he doesn't want to fuck me? I took the moment of his irresolution into my control and thrust his cock down my throat, past my gag reflex, to the point of no return. And I must have done something right, because in an instant, he pulled me off his dick and, grabbing my waist, threw me onto the bed.
He reached up my skirt and grabbed my panties, pulling them down very forcefully, before spreading my legs wide and coming up to kiss me passionately. He placed his dick at the entrance to my hole and said, "Andy?"
"Yes?" This time it was me who barely managed to get it out.
"I love you." And with that, I could feel him pressing into me, his dick starting its journey into my ass. I felt just the head break into me, but I couldn't take it anymore. I reached around, grabbed his ass, squeezed as hard as I could, and pulled him in. His moan of pleasure shot his warm, sweet breath all over my face, and I felt him pulling back out a little, then back in. He was fucking me. My brother Jake was fucking me in the ass. I could not have been happier.
For a few minutes, all I did was lay there with my arms above my head on the pillow, basking in the beauty of him, letting him use me as a temple of sex. Soon, he was telling me that he was coming, and I braced his ass again and right when I knew it was happening, I pulled him in and wouldn't let him go. He shot his cum time after time into me, and I could feel it inside me for each strain. When he was done, he took his time before pulling out of me and flopping next to me on his bed. For a few minutes, we didn't say anything, and merely enjoyed each others' presence. Eventually I turned over and put one arm onto his chest, cuddling with his side.
"I love you too, Jake."