My First Time with a Guy

I started transitioning a while back but it wasn't that noticeable. As a boy I was rather feminine. I wasn't especially noticing guys. I liked girls, and guys, but girls were the ones who apparently liked my femboy sort of look. In fact, in my teenage years I think that's what got me to score. Feminine as I was, there was never anything happening with boys, even though I had male friends. But a few times, when hanging out with a girl that's a friend, things turned hot. And I had some sexual experience before I started to transition.

As I got older, I felt more and more like a girl. At 5'3 feet tall, and 110 pounds I was almost petite. I moved away from my town, leaving it behind for no specific reason. I was already taking hormones, but given my baseline it wasn't super noticeable. When I moved to the city and got my first job though, I was no longer Kyle. I was Kelly, and I loved it. No one seemed surprised either.

As time went by, my appearance became more girly and attractive (at least according to the people I knew in the city). And II found myself attracted to boys more. Girls too. I frequented a bar that had a LGBT scene, but all it got me was girls, again. BI girls curious about doing it with a trans girl were there, and they were fun, but not one tuned into something serious. And I was too shy to talk to the guys, who in turn didn't approach me either. Maybe I wasn't that attractive. There were plenty of girls there who had work done, and looked a lot sexier, that's for sure. I relied on hormones, and cosmetic treatments that were actually increasingly effective. But slow to take effect, as I was careful not to do something dangerous.

One day, a few months after I was living in the city, and old friend said he was moving there too. We stayed in touch so he was up to date on who I was. Jack asked me if I knew about decent apartments. As a successful software engineer he could probably afford something good, but he was clueless. And my building was decent, in a good neighborhood. I found him a place on the same floor, bigger and better than my flat though. When he came to look t over we hung out. Jack was really nice, complementing me on how I look, making slightly inappropriate comments which I was dying to get from a guy, and being generally fun. His only fault was calling me Kyle. It was Kelly, I corrected him and he tried, but called me Kyle a few more times. But' it wasn't a big deal. It was the first time in forever that I spent time with a guy friend like that. At night he drove home, but the next day he closed the apartment. Two weeks later Jack was living two doors down from me.

We hung out a lot. We would go to different bars, including my bar. Jack didn't drink that much, because he's a big guy, and it took two or three pints of whiskey just to get him tipsy. One night though, we hung out at his place. We shared some exotic Rum he got on his latest business trip. At some point, we were watching something and I lay across the sofa. Jack was sitting, and I put my legs on his. I wore a tank top and short shorts that just barely covered my ass. Jack didn't deem to mind. At some point, I noticed the bulge in Jack's shorts. And then I remembered the changing room after gym class. Even in underpants, you could notice he was hung. Even flaccid you could see a noticeable presence under the fabric. And his soft shorts couldn't hide it when he started getting hard. I got spooked, but also excited. I moved my foot to his groin, and started touching. Jack moaned in pleasure, in his deep voice. I kept on rubbing, and he put his hand on my thigh, touching me. He moved to my inner thigh, just an inch from my cock. I suddenly realized, as I got hard, he might not know I'm still packing down there.

But that wasn't an issue, apparently. Jacks hand moved to touch my balls, and dick, and now I moaned, in a voice that was actually pretty girly. He liked it. Jack pulled me up to sit and kissed me. His big hands holding me. He wasn't super tall for a guy. Something like 6'1. But he had a somewhat apish physique. Big shoulders, big hands, super muscular legs. But not hairy. So here I was, kissing a hot boy, finally.

After the kiss he took my shirt of. I had perky tits and puffy nipples. Jack started licking and sucking my nipples. One hand just holding me, the other fondling my small round ass. It was awesome. He finally moved away. Took his shirt off, and shorts, and underpants with them. His tool was hard and big. I tried putting it my mouth, but could only fit the head. I sucked it a big. Jack smiled at my inexperience, and gave me instructions. I licked the top, and then his balls. And then covered his shaft with my tongue. I tried sucking again, and this time did a little better, just a ting bit deeper in my mouth, still no throat.

After the sort-of blowjob, Jack put me on his shoulder, like a caveman, and took me to bed. In bed he undid my pants and let my panties on. I lay on my back, my cock was peeking out of the small girly underwear. He slid the front part down just enough to expose my dick and balls. I was accustomed to blowjobs, but his was different. Jack was better than any girl cocksucker. He sucked my balls, and it was awesome. He then easily fit all of my mid sized cock in his mouth and gave me the oral of champions. A few minutes into it, all I could do is nut in his mouth. Jack apparently swallows. He smiled, got my panties down, finally, and turned to lick my ass. It was nice. Not my first rimjob, mind you. But what came next, was one helluva first.

Jack positioned himself on his knees in front of me, and opened my legs. He moved closer, and held my legs in a birthing position. His tip touched my balls. It was incredible. But also scary. I never had anything bigger than two fingers in my ass. And even that I did rarely. Jack first put his dick on mine. I got hard again and it was amazing. I though to ask for lube, but didn't. He got lotion, and put a little on my rectum. And some more on his tip. I was shaking with excitement, anxious, scared, happy, nervous. It all intensified as he entered me. His dick pierced my ass in a sharp movement. I felt my muscles contracting, my rectum closing around him as I felt the pain. He asked me to relax, and I did.

There was some improvement, but my muscles were super tense. I could feel something between early soreness and contraction pain you get from doing sports without stretching. He inched further, and started moving inside me. Finally, the pleasure came. His huge dick must've touched my prostate from the inside. It was amazing. And still painful. Jack pounded me like a mallet duck. Pleasure, pain and even a sort of exhaustion came and went, most of the time coming in together. My dick was no longer hard. I was focused on relaxing my ass, and it improved the sensation quite a bit.

Pounding and pounding, he was making me feel all these new things I knew nothing about, but an hour ago. Finally Jack was getting ready to finish. He slowed and inched his dick as deep as he could, stretching my rectum so hard. A felt a huge stream of semen in my ass. What a sensation! Another new, that I absolutely loved. And another, and a smaller third. I could still feel his dick convulsing inside me a couple more times. He took it out. My gaping ass was dripping semen on is bed. He said not to worry, and it was actually a bed cover, I first noticed. He cleaned us both up with wet wipes.

Jack got me under the covers, and got next to me. We lay under the covers, cuddling and kissing. My left leg in between, his. My right on top of his left, and my penis pressed against it. Getting hard again. My ass was sore and aching, in real pain. But I was on cloud nine. His dick and balls lay flaccid now, touching my lower belly and pubic area. My small tits were pressed against his chest. We made out for what seemed like an hour, and afterwards I finally stated gathering my clothes.

I told Jack how amazing it all was, and he promised the next time will be even better.

I went to my apartment to sleep. The next day I couldn't sit for long. But I slept like an angel.