Can I Try

Author's Note: OK, so this one is a fantasy I have had for years. Growing up I didn't really have any friends, but that wasn't always true. I don't feel bad about not having friends as a kid now. I think it makes me better to my current friends. I also think all the time alone contributed to what little writing skill I have. Randy was a friend I had when I was very young but he moved away when we were in third grade. This is what I would often fantasize about if he had stayed and we'd grown up together.

This one departs from my usual Trans focused erotic literature. I don't know why when I think about Randy I imagine my transition coming later, just a weird aspect of my sexuality I guess. I have it planned for two parts. Anyway, I hope you enjoy it.

Can I Try? (Chapter 1)

Randy's features were highlighted in the darkness by the glow from the screen as he concentrated on kicking my ass at Mortal Kombat. His blonde hair framed his face, just a little long and unruly. His face was beautiful and becoming more masculine by the day. I thought they complemented my more delicate and feminine features, but would never admit that. My heart fluttered as it always does when I look at him this way, one of my many secrets. I flipped my shoulder length dark hair out of my big blue eyes and turned back to the screen hitting combinations as fast as I could to fend him off.

Randy was my best friend and he was spending the night at my place. We both just turned 18, adults now, but it still felt like we were kids. We were on the couch pull out bed in my living room, my Mom upstairs either sleeping or reading. Randy finished me off as he always does with a devastating combination resulting in huge block letters "FATALITY".

Randy almost always picked Scorpion or Raiden as his character. He also almost always won. I always played Jade, a female character. She's just so beautiful, I like being her for just a bit. Randy gave up teasing me about my picking female characters in video games years ago. I think he liked looking at them too.

"I'm done." He said matter of factly and setting down his controller.

"Me too." I replied with a sigh of defeat.

"Is it time yet?" he asked.

"Yeah, should be." I said looking at the clock on the wall. It was past 11:30, when the soft core porn came on the premium channels.

I went and checked the stairs to make sure my Mom's door was closed. It was. I ran over and switched to TV and made sure to turn the volume down. There was a softcore skin flick on already and two impossibly beautiful people were going at it on the screen.

Randy and I were shirtless in our PJ bottoms and sitting cross legged on the bed. Our mouths hung open and I could immediately feel my cock growing. It wasn't as good as when I got hard in panties, but the fact that Randy was there with me and probably getting hard too made it really exciting.

You see I was Randy's best friend, but I was also completely in love with him. I wanted to be his girl fried so badly. OK, so that is weird, I am a boy right? I still couldn't help thinking of it that way.

I should also clarify the panties thing. I like to dress like a girl when I can. My Mom actually knows and she bought be some stuff so I would stop going through hers. We're a pretty liberal family that way, just me and my Mom.

Randy's family wasn't the same. His parents were religious and very conservative. They instilled in him such a fear of everything he swore he didn't even masturbate because he was afraid of going to hell. I didn't have any such compunction. I pleasured myself all the time, mostly thinking about Randy.

It was because of this conservatism that I had a hard time getting him to agree to watch porn with me. He tended to avoid things that made him horny because he'd get frustrated. I was really hoping tonight I could give him some relief. Both of us talked about girls all the time, but neither of us really had any prospects of actually dating anyone.

"Shut it off." He demanded just as the scene was getting really intense.

"Why?" I complained, "It's just getting good."

"You know why." He responded testily "It's just frustrating."

"Do something about it." I retorted.

"I can't."

"I'm going to." I replied laying back on the bed.

"Right now?" he asked incredulous.

"Yes." I said, pulling down my PJ bottoms and exposing my modestly sized but very hard cock. It was smooth and hairless because I shave what little body hair I have.

Silence fell and I could feel his eyes on me in the flickering light of the TV. I reached over to the end table and grabbed some hand lotion I had cleverly left there earlier and rubbed it into my cock. I moaned a little as I started rubbing. Randy was just staring at me and saying nothing. It was hard not to cum right away because I was relishing him watching me.

After a bit I got some more lotion and used my other hand to reach between my legs and start rubbing it into my ass.

"What are you doing?" he asked breathless.

"It feels good to rub here too" I said, moaning a little to emphasize the point.

"No fucking way." he said incredulous.

"Mmm hell yeah." I said, pushing my middle finger into my ass.

"Wow, you're really fucking weird" He responded as I started stroking my cock and slowly fingering my ass.

"Whatever," I replied as he stared on mesmerized, "it just feels good."

It was a good thing the soft core porn on the TV was on a dialogue scene or I would have cum too quickly and things wouldn't have happened the way they did.

"Can I try?" Randy finally said.

"Finally!" I thought to myself, though to him I just nonchalantly said "Sure."

I stopped touching myself and grabbed the lotion and squirted some into his outstretched hand. I was super excited that I was going to see his naked cock. I could clearly see the outline of it pressed hard against his PJ bottoms. It looked bigger than mine for sure, it was making my mouth water.

He rubbed the lotion over his fingers with his other hand. What he did next surprised the hell out of me. My eyes just about popped out of my head when he started to reach for me! I guess I misunderstood what he meant by "Can I try?"

His hand slid lightly over my slippery little cock, barely touching it, then just as lightly across my tight sooth balls and down between my legs. Then he pushed his finger into my tight ass, easily pushing past my resistance.

My back arched and I let out a long hard moan as I realized I was holding my breath while this was happening. I couldn't believe this was happening! He hesitated just a moment before he started working his finger in and out of me. I was so overwhelmed by it all my body just responded automatically, moaning and writhing under his thrusting finger.

The soft core porn on the screen was starting to heat up too. A muscled stud was kissing and groping this blonde girl's big fake tits. Randy pushed as second finger inside me. It was just too much. I reached down and grabbed my cock hard and squeezed, my body shuddered violently and bucked against Randy's thrusting fingers. Hot cum splashed across my belly as my back arched hard and I tried not to cry out.

"Holy fuck." Randy exclaimed as my breathing started to return to normal. "Holy fuck." he repeated.

My belly was completely soaked in cum, my PJs bunched around my ankles. Looking up at Randy I could see him squirming and trying hard to fight nature. He was looking down at my cum soaked body and back and forth to the TV screen. On the screen the blonde girl's head was now bobbing in the stud's lap. I saw that and I knew what I had to do.

I reached up and pushed him back onto the couch cushion.

"What the fuck?"

"Shut up." I said and meant it. I grabbed his PJs and worked them down his hips to his thighs, exposing his gorgeous big cock. I say big because it was bigger than mine. Mine is maybe a little over five inches long, thin and has a lovely delicate upward curve to it and it is almost feminine looking in a way. I know girls don't have cocks, but if they did they would look like mine, or at least that is what I think.

Randy's wasn't huge, probably six and a half inches, but it was thick, straight with a big head. It looked like it belonged on a man. I didn't look long though because I needed to do this quick before Randy freaked out.

I grabbed it in my hand, god it was so thick hard and throbbing, I immediately brought my head down, sliding my soft lips over the head. My mouth was salivating like crazy, which lubed up his shaft quickly. I let him slide deeper into my mouth, my tongue caressing it lovingly. I was rewarded with a groan from Randy. I went down deeper, I pushed myself, breathing heavier through my nose and working my throat, I wanted to take him all but I couldn't quite.

I took him as deep as I could and stayed there for just a few seconds that seemed to stretch on forever. I was savoring the moment as much as his gorgeous cock in my mouth. Something inside me slipped into place, like gears meshing properly for the first time. I felt gloriously fulfilled and everything felt so right with the world. As I started sliding my lips lovingly up and down his raging hard dick I was euphoric. This is something I was meant to do, what I was made for.

I didn't have long to savor it, by about the third time I moved my head up and down he started trying to push away, his legs moving frantically under me. I held his hips in place with my hands and took him deep two more times fast and then just held the head between my lips as he started pumping hot cum into my mouth.

I knew what cum tasted like, had been tasting myself for years after I would masturbate. I generally had developed a taste for it. This was different though. The physical taste was more or less the same as mine, I wasn't enough of a connoisseur to really tell the difference, but combined with that euphoric feeling of rightness, pride of pleasing someone I was so attracted to, well it was the most amazing feeling ever.

All of these thoughts and feelings were going through my head as I struggled to swallow all of his load. It just kept coming and coming, spurt after spurt. It filled my mouth and spilled past my lips and over my fingers. I kept sucking gently as I worked what had escaped back up his still throbbing cock to my mouth the greedily lick it up.

At last he subsided with a huge sigh and I felt all the tension leave his body. I finally took my mouth off of him, I swallowed the last bit and rolled over to lay next to him. I looked over at him, his expression unreadable as he looked up at the ceiling, looked up at nothing. I joined him.

"Are you OK?" I asked after several minutes of just listening to him breathe.

"Yeah." he replied, sounding unsure of himself. I was pretty worried about how he was feeling.

After another few minutes he asked "Does this make us gay?"

"Only me I think." I replied. I was happy to take on the responsibility if it lifted the weight off of his shoulders, helped him not feel shame. It was just a label with stupid arbitrary rules attached, I felt feminine and right in that moment, I wasn't afraid of the label.

He turned to me, his hand caressed the side of my face more gently than I could ever imagine him doing. He looked me deeply into my eyes and said "I'm not so sure." His lips closed the distance as he kissed me.