Chapter 1

Sam and I had been friends for as long as I can remember. We met way back in preschool when he stole some crayons from my cubie, I complained to the teacher and he cried his eyes out until the end of class. That image right there- that's the Sam I'll always think of. I don't remember how we became friends, I think I've always felt sympathy for people who cry. And Sam cries a lot. 

Later in middle school I was constantly protecting Sam from bullies. They would make fun of him for being skinny or having long hair. But that's the look we were going for back then. Sam and I were big into Rock and Metal. We decided we were going to start a garage band and be big like Nirvana. Then we could leave our shitty town and play for big cities across the States. Sam had a great voice too, that kind of androgynous tone that makes for amazing vocal range. Unfortunate for him I played the guitar like my hands were made of dead fish... It's funny now but back then we actually believed we had a chance. 

But that was then. Things began to change around High School. 

Sam started acting different. He wore tighter fitting clothing and grew his hair out even longer while I switched to tee-shirts and crew cuts. But it wasn't just his appearance. While everyone's voice started dropping lower and lower, Sam's voice rose an octave. Every word out his mouth was smooth and cheerful. Even the way he walked was different. I had seen professional models on the runway walk with less grace. One or two times I actually caught myself starring at Sam's butt for a little too long. 

"Are you starring at my ass?" Sam asked me once.

"It's hard not to when you're squeezed into those" I joked.

Without missing a beat, Sam pulled his jeans down under his butt and slapped it a couple of times, laughing like a fool. It was actually kind of nice the way it jiggled a little with each slap. I had to remind myself that this was my best friend. You know, the same guy who likes to fart in a doorway right before you enter a room. That guy. 

All of these things had gone over my head. I think it's harder to see people change when you're constantly hanging out with them. But then Sam did something very unexpected one day. He wore a dress to school. And it was getting more difficult to ignore the obvious.

I could talk about the whole 'dress incident' for days, but it's a big thing that I don't really want to get into here. Long story short: The teachers complained, the students were merciless and Sam never wore a dress to school again. The sad part is that with Sam's figure he was actually pulling it off! 

Shortly after this, Sam said he wanted to talk to me about something after school. We were in his room, sitting on his bed playing Xbox. One minute we were joking around, the next Sam got quite. He looked real serious. 

"Henry," he said, "I think I'm a girl."

It took my brain a few minutes to process this. Truthfully I wasn't really surprised, but it was still awkward to hear a confession out of nowhere.

"That's cool, man- I mean, uh, yeah dude" was the only thing I could muster.

Things were a little tense between me and Sam for a few weeks, but he never said anything about it again and I eventually got used to thinking of Sam as a girl. To be honest he looked more feminine than most of the girls we went to High School with! I still had to protect Sam from assholes jocks who had nothing better to do than mess with guys half their size, but nothing serious ever happened. Most of the time people never even noticed. He was very convincing, and whenever we went out to public places guys would actually approach him and ask for his number! Sam never seemed to be interested though. At that point I wasn't sure what he might be into. 

Whatever the case I didn't mind all of the attention Sam brought with him. I could never get girls to pay attention to me, and here was Sam in his tight jeans and long curly hair laughing like a giddy school girl at all of my dumb jokes. But something still nagged at me in the back of my mind. There was a lot I didn't know about this side of Sam and I was determined to learn more.

My chance came in the form of Sam's parents leaving for a short vacation. Apparently his father had left an unopened case of beer in his garage fridge. This might not seem that big a deal but for us it was a once in a lifetime opportunity. Me and Sam were never invited to parties at school and neither of us had the guts to pay an adult to buy alcohol for us. An entire case of booze with no adult supervision for the next week was too good to pass up.

"You better get your sorry ass down here before I drink it all," Sam yelled at me over the phone. I could already tell he had a few.

"Alright," I told him, "but try to save some for me, okay?"

I drove as fast as I could. When I got there Sam answered the door with an empty can in his hand and a funny look on his face. His hair, usually meticulously curled, was a frizzy mess. He was wearing a tight tank top and even tighter sweatpants. You could see just about everything in those pants. 

"It's about time," he said "you ready to get fucked up?"

"It's just beer, Sam."

"Yeah, twenty-four of them, and you're not leaving until we empty every. Last. One."

I hurried him inside before the neighbors heard any more of drunk Sam. We filled a cooler with ice and carried it up the stairs to his room. I had a difficult time not staring at Sam's butt as it practically wiggled in my face. When we got to his room I was surprised to see that Sam's new identity didn't make its way into his living habits. Empty soda bottles and piles of books and games littered every corner of the room. The only difference was that instead of a mound of dirty boxers in the corner there was instead a dainty heap of panties. We both started drinking, Sam more than me. I was lying on the bed, sipping my beer, trying to pretend that the taste didn't bother me. Beer definitely isn't my thing, but it did the job just fine. Only three cans in and I was starting to feel a little more relaxed. Sam had a small pyramid of empties next to him and seemed to be doing just fine. 

"Hey Sam," I said.

"What's up?" he asked.

"So uh... ah nevermind."

"What is it?" 

"It's dumb," I said, "don't worry about it."

Now I had peaked his interest. He leaped from his chair hopped up next up me on the bed. Maybe it was the beer but he smelled really nice. I wondered if he showered with feminine products. 

"Tell me!" he demanded, pinching my arm with his nails.

"Ow! Okay, jeez!" I submitted.

"I was wondering what you..."

"What I what?" he asked.

"What you want. You know, now that you're a girl." 

I immediately felt dumb asking it. I didn't want Sam to feel uncomfortable, not after things had starting getting back to normal. Sam must have understood how I was feeling.

"How about this," he said, putting his index finger to his nose. 

"You can ask me any question you want, and I'll answer it."

"Okay," I said.

"But," he continued, "I get to ask you any question I want in return."

This seemed fair, I was worried what questions he might have in mind, but at the same time I was too curious to let this slip away. 

"Deal."

"So are you attracted to girls, or do you like guys?" I asked.

Sam thought for a second. "I'm not sure yet," he finally admitted, "but I'm leaning more towards guys?"

I was satisfied with this answer. 

"Okay, now it's my turn," Sam said with an evil grin. 

"Are you an ass-guy, or a tits-guy?" He asked, poking me in the stomach.

"Really? That's your question?"

"Yes it is," Sam said, crossing his arms over his chest. 

"I guess I'm an ass man," I said.

"Makes sense," Sam shrugged. I couldn't help but feel there was something more in that question. 

This exchange went back and forth for a while. I would ask Sam a serious and thoughtful question about gender and sexuality and Sam would ask something embarrassing and personal to get a rise out of me. By the end of the first hour Sam had some serious blackmail material on me and I was more confused than ever. Eventually I got tired of it and decided to ask something equally humiliating. 

"Okay," I said, "so you wear panties now, right?" 

"Uh-huh," Sam nodded. Unsure of what I was about to ask.

"So where do you keep the package?" I finished, watching his cocky smile slowly fade into one of embarrassment. 

That's it, I thought. That should put an end to his little inquisition. But Sam came back with something I never saw coming.

"Here," he said getting up from the bed, "I'll show you."

Sam dropped his yoga pants around his ankles. My jaw nearly hit the floor. He was wearing a cute pair of pink panties with a blue waistband. My eyes ran up his legs. They were completely hairless, and had a nice curve to them. And the way the panties hugged his slender hips- I couldn't believe what I was seeing. It was uncanny.

"Pretty good, right?" Sam teased, "and then I just tuck it like this."

Sam spun around and bent over, raising his butt into the air. I watched as the pink fabric stretched across my friend's perfectly shaped ass. You could see the faint outline of his dick though the taut cotton panties. A little below I could make out a small bulged where his balls were neatly tucked away.

"Sam, that's..."

"Freaky, right?" He laughed, "I thought you might-"

"No," I interrupted.

"That's really hot, dude."

Sam stopped laughing. His face turned a bright red and he stood up straight. The room was quite for an uncomfortable amount of time.

"You think it's... hot?" Sam finally asked.

At this point the beer had wormed its way into my brain. There wasn't anything left to filter the stupid things I was saying. "Yeah, I mean, you've always had a nice ass. You know that." Sam looked at me like I had just shot him. I didn't really understand what I was saying. All I knew was there wasn't any use trying to get out of it now.

"Are you... you're messing with me right now." Sam looked a little angry.

"No!" I blurted out, "I really like your butt. I think it's cute."

What the hell was I saying! This was it, things were going to be weird again now. I couldn't look Sam in the eyes but I knew he was locked onto me. I waited for the worst. 

"Wait right there," Sam said, "I want to show you something."

He walked to the other side of the room where his closet door was, never taking his eyes off me. I watched as he slipped inside the closet and closed in shut. My mind was racing. I had no idea what was going on, but I knew whatever it was it was my fault. I thought about leaving right then and there, but I knew that wasn't an option. About five minutes later the closet door opened and Sam's arm and head poked out.

"Okay. You ready?" He asked. There was a nervous tone in his voice. 

I nodded my head.

Sam slowly crept from behind the door. He had changed his clothes, and was wearing a dress now. A simple white gown that fell just below his knees. It was only the second time I had seen Sam in a dress, but somehow it felt natural on him. Like he had been wearing the wrong kind of clothes all of his life. I never wanted him to take off that dress, and at the same time... I sort of did. 

"What do you think?" Sam asked.

"It's beautiful," I told him. 

Sam walked back to my side of the bed and did a twirl. It felt like someone was sitting on my chest. 

"Can I... Would it be weird if I, uh..."

"Touched it?" he asked.

Sam bit down on his lip and nodded. I felt myself stiffen. My hand automatically reached out and grabbed hold. I started at his shoulders and worked my way down. The dress was silky and smooth fell perfectly against Sam's slender frame. I eventually reached the bottom. I should have stopped there but my hands were on auto-pilot. I reached out and cupped his cheeks. Sam's ass was soft and rubbery in fingers. I squeezed down and Sam gasped a little. 

"I'm sorry," I said pulling my hands back.

"No, it's fine" he said smiling back over his shoulder, "You can go under the dress, if that's easier..."

I didn't wait for another invitation. I slipped my hands under Sam's dress, running them up along his thighs until they hit his crotch. I stopped dead. I had always dreamed of putting my hands up someone's dress but this... It didn't matter. Guy or girl, best friend or not, It was far too late to turn back. I started rubbing the crotch of Sam's panties with one hand while the other hand groped his cheeks. I could feel Sam's breathing getting shorter and everything started heating up under his dress. I lifted up the back to get a better view. His panties were already drenched in sweat and clung tight to his crack. I pulled back my hand and found it slick with Sam's juices. 

Sam pushed me flat on my back and climbed on top of me. I could feel his hands undoing my belt. 

"It's not fair," he moaned. I had never seen Sam this way. It was like something had possessed him. Possessed both of us. I felt Sam's hand reach into my pants and take hold of my cock. It throbbed in his grip. He pulled it out and starred at it.

"You keeping this to yourself."

"Sam."

I watched as Sam's warm mouth wrapped around the head of my cock, and then disappear completely as it slid down his throat. I grabbed hold of his head, hooking my fingers into his curly hair. Sam worked my cock up and down, up and down, up and down. I could feel my head pressing against the back of his esophagus with every stroke. I looked down and saw Sam's cute face starring back up. I wasn't going to last long like this.

"Sam, I'm going to-"

"Nah yebt!" Sam yelled pulling my shaft out of his mouth and squeezing it hard. He climbed up further onto me and turned around, lifting up his gown. From here I had a perfect view of Sam's panties pressed against my swollen dick. He started grinding against me.

"Uhhh, Uhhh fuck," Sam was really getting into it now. I could feel his own cock rubbing through his panties against my thighs. I pulled the wet fabric aside to get a better view. Sam's balls fell out and stuck to my chest. I could see his tight little asshole now. It was the most incredibly sexy thing I've ever seen. I prodded it a little with my finger, watching it pucker. Then I slipped it in completely.

"Oooooooooh Henry," He let out a sigh. 

I started fingering his asshole and he rubbed harder and faster against my cock. 

"Sam, I can't hold it back anymore!" 

Sam jumped off and positioned himself on the bed next to me. He bent down low, spreading his legs apart while sticking his butt up into the air. 

"Please," Sam begged, "I want you to finish inside me."

That sight alone almost made me cum, but the idea of shooting my load inside of Sam was too powerful an image. I lined my cock up against his hole. Sam whimpered a little as I rubbed my head against his entrance. I slowly drove it forward, inching my way inside. With one final push I bottomed out deep within Sam's ass. Sam looked back at me over his shoulder. There were streaks of tears running down his face and the most beautiful, sexy smile I've ever seen. I started pumping into him. Slow at first, but then we got into a steady rhythm. My balls started slapping against Sam's junk. It made a satisfying "pap" sound with each hit.

"Henry! Mmmff Ooooh fuck me," Sam pleaded. I could feel him squeeze tighter around my shaft as I drove it in. 

"Turn around," I told him.

Sam flipped onto his back with my cock still inside. His dick made a tent in his dress, I pulled it back and it sprang forward with a small spurt. From this position Sam looked so vulnerable. I began pumping into him again, this time harder and faster. Sam wrapped his arms around my neck. He moaned with every push. My heart was pounding. I felt a surge of electricity shoot through all of my veins.

"Sam, uh uh. I'm gonna cum."

"Do it inside" he groaned in my ear.

I felt all of myself let go. I pumped three more times, trying to reach the deepest part of Sam's ass, and then I came. I came harder than I think I'll ever cum in my entire life. Every bit of me drained into Sam's sweet hole, filling him up to the brim. I pulled out and watched my fluids leak down his crack.

"I think- I ruined your- dress." I said between breathes. 

"That's okay," Sam said in a whisper. 

I bent down and kissed him. His mouth was sweet like candy. I think it was the chapstick he wore. 

"How long did your parents say they were going to be out of town?" I asked.

"They come back next week," Sam smiled.

"Good," I smiled back. "Then you're going to need a few more dresses."