The first trans girl I was with was Chrissy, except back then she was still a he though a very feminine he. I saw him around school and also in the neighborhood. Smoking hot. Chrissy was tall and slim with long brown hair that he usually wore in a ponytail. He was a dark-eyed Hispanic with a very graceful and sexy way of moving. He was quiet, reserved. I always had the feeling it was a case of still waters run deep. I had already been visiting with a fem gay man, much older than Chrissy, so I noticed (and appreciated) Chrissy very much.

When I saw Chrissy around high school he was usually with his posse of fem boys, so I was too shy to try and talk to him but it was hard not to stare at him. I was sure he did not know I existed but it turned out he did. (I found out later some of the fem bitches in his posse had seen me eyeing him and teased him about it.) One morning when he was by himself he actually stopped me in a deserted school hallway and said hello in a soft sexy voice. He smiled seductively and said it seemed like I had been checking him out. I had to smile too and I told him I thought he was really sexy. He seemed pleased but the way he was looking me in the eye made me think he wasn’t sure I was serious. Then the bell rang and kids started pouring out of classrooms. Chrissy playfully stuck his tongue out at me and then walked away. I had a massive hardon the rest of the day and, when I got home, I went straight to my room and jerked off for him.

After that, when I saw him in the hallway, he still didn’t pay any attention to me but then we met late one Saturday afternoon in a neighborhood park. We were both taking a shortcut. I was coming back from downtown and he was heading downtown. I said hi and he started to walk past me without saying a word. I was devastated that he was ignoring me but I saw him steal a glance at me and then recognize me. Then he stopped and said hi. He was in a white tee shirt, revealing smooth and slim tan arms, his tight jeans showing off his long legs and round little ass. I felt awkward and nervous but my attraction to him was strong and I tried to make small talk. I said it was a nice day, I had been downtown. Chrissy shrugged and said, “Yeah.” I still had no idea he was interested in me but it was became apparent very quickly that he was. He said, “You’re Ron, right?” I was shocked he knew my name. I said yes and…at that point I realized: I still didn’t know his name. So I asked. He very matter-of-factly said his name was Chrissy.
Chrissy was a bitch but he was no sissy bitch, he was more the street bitch type. I soon discovered he didn’t waste any time. He gave me a very bold look and asked me did I like “gay guys.” I smiled and said I did “if they were sexy bitches.” He giggled at this and then glanced around. I was certain he was about to come onto me and the thought made me breathless. He narrowed his dark eyes and asked me did I want to do something. I said, “Oh yes.” He was eyeing me intently, and I was becoming very excited; he had this really sexy girl quality. As I would discover, in addition to being horny for me, Chrissy liked to take charge. He said in his soft voice we could “go over there,” into some bushes in a stand of trees. I followed him, we walked quickly before we were spotted. The little clearing wasn’t a very romantic spot, empty beer cans littered about, crumpled cigarette packs, some used condoms here and there, an empty pack of rolling papers turned inside out and even a discarded hypodermic needle under one of the bushes. But I didn’t care, I was elated and horny.
Chrissy acted so serious, almost somber, but he was acting increasingly girly, and it seemed very natural. I guess what didn’t seem natural was when he was being straight. He asked me had I ever been with a gay boy and I said yes. He asked me had I liked it. I said it was awesome and he seemed very pleased. For the first time he smiled, a very sweet sexy smile. “It’s someone in school?” he lisped. No, I said, it was an older gay man, adding, “He’s very fem.” Chrissy seemed to think about this. Then he said, “Well sweetie I think I’m sexier than an older guy,” and he gave me his little crooked grin, a kind of self-conscious smirk that I would become used to seeing. He stepped closer. His face was very smooth, his eyes very dark. I thought he was really pretty, with delicate features, pouty lips and very sexy eyes. Then he very vampishly asked me to kiss him. I half expected it and I immediately leaned forward, slid my arms around his slender waist and pressed my mouth to his moist soft lips. Kissing him was awesome. He had his mouth open and I pushed my tongue in his mouth. He used his tongue to lick mine. He took my hand and he leaned back against a big tree trunk. We stared at each other for a moment and we kissed again, a long passionate kiss. When our lips parted he giggled and shyly confided my kisses were making him very hard.

This is when things began to go differently from what I expected.

He gave me a very hot femmy look and whispered did I want to feel how hard I was making him? I gently felt his dick through his jeans and he giggled and squirmed with a delighted smile on his face. His dick felt not only rock hard but huge. He asked me did I like it, did I want to see it? Before I could answer he opened his jeans and pulled them down. He had blue panties on under his jeans and he slid them down as well, almost to his knees. His thighs were slim and very smooth. His dick was at least 8 or 9 inches long, with a medium thick shaft that tapered to a cone-like knob. A skin rocket! He was uncut only, looking at his dick in the park by the tree, he was so hard I thought he was cut. He gave me his self-conscious little crooked grin as he watched me looking at his dick and asked me did I want to “do” him. This wasn’t at all what I expected but I was eager to serve him anyway he wanted. He leaned back against the tree and I got down on my knees. I licked his knob and then kissed it, holding his dick by the shaft. His dick tasted fleshy and clean, very warm. Delightful. Then I opened wide and took his knob in my mouth. I slowly sucked his dick into my mouth, rubbing it with my lips and tongue. He had curly dark-brown pubic hair around the base of his dick and on his tummy just above it. It was bristly and it tickled my face. I heard him give a little moan and say, “Oh God, God,” almost under his breathe. I didn’t expect him to cum in thirty seconds but after three or four minutes of sucking him I began to wonder if maybe he didn’t like the way I was doing it. For one thing, his dick was so long I couldn’t get it all in my mouth, I couldn’t deep throat him. The best I could do was about a half, maybe two-thirds, of his cock. But in another couple of minutes he began to moan, deep involuntary moans which I found very exciting. He gently put his soft hands around the back of my head. He gasped out that, “You’re going to make me cum, Ron!” I looked up at him while rhythmically sucking his knob, rubbing the back of it with my tongue. His eyes were closed and when he opened them we exchanged looks of lust. He squealed, “Oh Daddy can I cum in your mouth, baby?” I grunted and he put his head back. I felt him tremble, then he caught his breathe and began squirting thick streams of creamy jizz into my mouth. I sucked and swallowed until he went dry. Then I gently licked his dick as it began to soften. Finally, he sighed and stepped back, his dick slipping from my mouth. Again, the crooked little grin, and he bent over and pulled up his panties and jeans. He caressed my shoulder but he seemed to be avoiding kissing me. He giggled and told me that it had been awesome. He said, “Oh Ron I feel so wonderful right now.” Then he smiled sweetly and told me, “I got to go baby, I got to meet my sister. She’ll be pissed if I’m late.” Then he bent over -- I was still on my knees -- and gave me a quick kiss on the mouth. Without another word he turned and walked back to the path. He never looked back and I felt really down. I couldn’t believe he had left without making me cum. A hand job or something. I wondered if he was really meeting his sister. Maybe it was just an excuse. Maybe he decided he didn’t like me after all. But he was the street bitch type and the feeling I had of having been used was deeply exciting. So my feelings were hurt but at the same time I felt very grateful to him. Before leaving I whacked off in the bushes. When I shot my load I called his name.