[Patreon Exclusive] HIS NEW GIRLFRIEND: Chapter 4 (Patreon)

I showed up at James’s school without warning James. I figured I would go in, get his stupid little act over with, and then start preparing for the dance. I didn’t want him wasting my time with planning, telling me what to wear, how to do my hair, my makeup, telling me what to say. In his original offer, he just asked that I make an appearance to sell his stupid little lie, so that’s what I did.

It was lunch when I showed up with a sandwich and a banana in a brown paper bag. He was at his locker, back towards me. I was dressed to kill, to turn heads. That morning I’d shaved my legs (even though my blonde body hair was practically invisible), plucked my eyebrows, waxed my downstairs. I’d absorbed a few YouTube makeup tutorials and I’d taken my look to another level. I took my sister’s old school uniform and made a few adjustments, shortening the skirt, tying the top up in a knot to expose my belly. I picked up a box of hair dye from the drugstore and I’d given myself some highlights. I was pretty impressed with myself, to be honest.

More heads than I cared to count turned as I walked those halls, my heels clicking against the floor as I went. As the heads turned, they became silent. It wasn’t until me and my wave of silence were ten feet away from James that he turned around and froze, his eyes locking onto my body. I reached his lunch out to him. “You forgot your lunch, babe,” I said. And now the heads turned to James, who was still frozen. He wanted a hot girlfriend, that was exactly what he got.

“Thanks,” he said, eyes still wide. He held the bag awkwardly, still not sure what to do with it. I wondered if he’d forgotten our agreement altogether or if he was just taken back by my new look, my undeniable sex-appeal. I felt incredible in that outfit, in those heels, that skirt floating down around my thighs. I kissed him on the cheek, leaving behind a deep red impression. “I had fun last night,” I said and then whispers broke out around us.

He forced a smile. “Really?” he said stupidly. His eyes continued to explore my body while he stood totally frozen.

I stepped in close to him. “Really,” I said into his ear before reaching down and grabbing his package. He was surprisingly big down there. The crowd oohed. “See you at the dance, Friday.”

Then, I turned to leave. As I left, someone whistled. Even the girls were staring at me with a mix of wonder and jealousy in their eyes. Now I couldn’t wait for the dance. I couldn’t wait to leave all of these boys a dripping, drooling men on that dance floor.

When the night finally came, I was ready. I spent the whole day preparing, picking out the perfect outfit, applying and perfecting my hair, my makeup. Kylie’s voice was now second nature. I discovered that, with some clever contouring, I could create the convincing appearance of cleavage with my sister’s lower-cut dresses. The dress I picked out was a deep red with a slit along the leg that ran up all the way to my hip. I was irresistible. I would be the talk of the night, of the week, of the whole damned school year. I felt great, better than I’d ever felt in my entire life. I was starting to think this was who I was meant to be, this was who I was—Kylie, not Kyle. And to think, all of this started because of some stupid bicycle.

When I stepped into that gymnasium, as expected, heads turned, dates got jealous. I could feel their gazes locked onto my body, my chest, my ass. Who could blame them?

I walked around the room, looking for James, but he was nowhere to be found. So I found a spot on the edge of the party and I waited, soaking in all of the gawking glances that came my way. Unlike the more mature and more inebriated men at the club, the boys at the dance weren’t teeming with confidence. They all stared at me like I was the eighth wonder of the modern world, but none of them dared come to talk to me, to ask me to dance. Though I could see in their eyes they wanted to more than anything.

Then I heard his voice. “Kylie?” he said. I looked over and it was James. His cheeks were red. Even he, knowing my secret, couldn’t deny what I’d managed to accomplish, who I’d managed to become. He wasn’t laughing now, he wasn’t smirking. He was dressed nicely, in a good suit, hair nice and proper. He reached his hand out and said, “Care to dance?”

I took his hand and he led me to the dance floor. He didn’t mention the elephant in the room, the fact that I was really a man. I knew James well enough to know that he wouldn’t be caught dead dancing with a man—but that’s what we were on our way to do. As we reached the dance floor, the song changed to a slow number. Even that didn’t deter him. Slowly, he brought his hands down to my hips and he took a step in towards me. I wrapped my arms around him and rested my chin on his shoulder. “You smell nice,” he said. His voice was almost shaken, still in shock. We started to dance. He led. He held me close. I could feel the ridges of his muscles, his pronounced football-player chest, his stacked shoulders.

Other men watched us dance, totally jealous.

His hands slipped down onto my ass and he gave me a squeeze. I looked him in the eyes. He bit his lip. What was that? Did he just do that on purpose? You couldn’t exactly squeeze someone’s ass by accident. But why? It was discreet enough that no one could have seen, but wasn’t that the whole point? To show me off? To be seen? The only reasoning I could think was that he was actually developing a thing for me. James—even knowing my secret, my true male identity—was developing a thing for me. Impossible.

Or maybe not. As we continued to dance, I began to feel his bulge against my abdomen. He was getting hard. I was making him hard. I gently wiggled into it, grinding it flirtatiously with my body. He got harder. Even through his pants, through my dress, I could feel it pulsing with his heartbeat. Holy shit, I was making him as hard as an iron rod.

And then my heart skipped a beat. I was getting hard, too. My own cock was beginning to grow and harden in my panties. “I need to go to the bathroom,” I said, before things got out of control. At any moment it could have sprung free. And the lighting in that gymnasium wasn’t nearly as forgiving as the low-lighting in the club. Not to mention the dozens of eyes that were aimed in my direction. I couldn’t take the risk. I slipped into a stall in the girls’ bathroom and I let my cock out to breathe. I waited for my heart rate to drop, for myself to relax. Slowly, my penis began to become flaccid again.

Then I opened the stall door and there he was, standing in the middle of the bathroom: James. “What are you doing in here?” I asked. He motioned towards the bathroom door, which he’d locked. Without saying a word he grabbed me, pulled me tight, and kissed me. At first I was frozen. Here was my best-friend of many years, arms around me, tongue in my mouth. And for some strange, fucked up reason, it felt right. I surrendered. We stumbled back into the wall and his hands began to explore my body. “Fuck, you’re so hot,” he said.

I ran my hands up and down his body, eventually finding the bulge of his erection. I massaged it through his pants, which seemed to power him up, raise his energy. I could feel his heart throbbing, beating against his chest rapidly like a Native war drum. I squeezed his cock. I wanted to make him come, to make him drool and drop to his knees.

“Suck my dick,” he demanded, so I did. I pulled his pants down as quickly as humanly possible and then I grabbed his dick like I needed it. Fuck, it felt so good, warm, throbbing in my hand. I ran my hand up and down his length a few times before plunging the beautiful specimen into my mouth. Who knew James had such a massive cock, such an impressive length? And it got so hard, like a damned steel beam. Sucking his cock, I nearly rubbed off all of my lipstick but I couldn’t have cared less, it felt so good, so right. He grabbed my head and started to fuck my face like a glorified sex toy. I should have been pissed—I should have stood up and slapped his face—but instead, I loved it. I let him plunge that slick cock down my throat as he pleased. Even though I was running out of breathe, it felt so fucking good.

He started to moan. But before he got too far gone, he took a step back. “Get up on the counter,” he demanded, pointing at an empty space between two sinks. I climbed up onto the counter and then he grabbed me by the legs and pulled me into position. He flipped up my skirt and ripped my panties down my legs. My heart skipped a beat. My erection was now out in the open, for him to see, so he could remember what he was doing—fucking a man—fucking his best friend. But he only paused for a brief moment, and it was surprisingly to admire my cock. He looked at it with glowing eyes and then slowly, he reached out and grabbed it, feeling it, holding it, squeezing it. He liked it. But his targets were set elsewhere: on my asshole.

He took his saliva-covered cock and lined it up with my tight little hole. I felt it press up and then push in. My body began to tremble—a combination of nerves and pleasure coursing through my veins. I was about to be fucked in the asshole by James and his big dick. The craziest part about it, I didn’t care. I wanted it more than anything. I wanted him inside of me with the thick log, pumping me hard, pumping me senseless.

He pushed in and I clenched. “Holy fuck,” he said in a elated state of his own. He revelled in the moment for a few seconds, silent, still, my asshole clenching his big meat tightly. Then, the race was off. He fucked me like the horny teenager he was, ramming my ass senseless with impressive speed, impressive force. His toned hips slapped against my increasingly numb butt cheeks with every revolution. I began to relax and he sunk deeper.

It felt incredible, every inch of his veiny, hard dick inside of me—his bulbous tip sliding in and out of my tight hole. “Fuck me! Fuck me! Fuck me!” I yelled, and he sure as fuck did.

He held my thighs tightly, holding me in place so I wouldn’t slide back from the force of his relentless blows, which were getting faster and faster, harder and harder.

“Beat my dick,” I said, and he followed the command without hesitation. He grabbed my cock and started to beat me off while he pumped my asshole mercilessly. I let my body slump back. Euphoria had consumed me completely. There was no resisting surrender, no holding back. That euphoria reached its climax, I screamed, and my cock erupted like a volcano, shooting straight up and covering my body, his body, his hand, the counter, everything. I had no idea I was capable of such a load, such tremendous volume.

He screamed out loud and then I felt it—my ass filling up with warm cum. My eyes shot open wide and my body tensed. My asshole clenched onto his dick as to not let him go, as if it wanted every last drop of his gooey substance. A man just came in my asshole. My best-friend just came in my asshole. We stared one another in the eyes. “Shit,” he said, the realization hitting him like a sack of bricks.

I didn’t know what to say back. Nothing had ever felt so good, but he was… James. And I wasn’t Kylie. I was Kyle. Everything suddenly seemed wrong, broken, misplaced. That familiar pit returned to my stomach. “I should be going,” I said. I adjusted my skirt, wiped the cum off of my stomach, and then I left.

My heart wouldn’t stop racing. I couldn’t quite process what had happened. Had I just lost a friend? Did I make a big mistake? Had I fallen too far into this guise, into this Kylie character? And if so, why did it feel so good? So right? It wasn’t remotely fair that this was the way the world worked, how society operated. If I wanted to be Kylie, I should have been able to be Kylie, no?

There was a knock at my door, but I didn’t answer it. Instead, I found myself face to face with Kylie in the mirror. I’d lived up to my end of the deal. I got his chips, I made the appearance at his school, and I showed up at the dance. That was that—I could just leave it all behind me. Get my stupid new bike, forget about the tape, and never see James again. It wouldn’t be hard to do. We went to different schools, after all. I could apply at an out of state university and never come back, never think about it—forget it all ever happened, pretend it was all a nightmare.

“Hey,” a voice said behind me and I nearly had a heart attack. It was James. He must have climbed in through the window. “Why’d you leave?” he said.

I didn’t know what to say back. I felt humiliated, ridiculous. I couldn’t bare to have him look at me, not like this. Standing there, I wished there was some way to turn back time, to reset everything. Let him release the stupid tape. Or better yet, never make that bet at all—have some common sense and know the Leafs would lose the game. But I couldn’t do any of that.

“You should go,” I said. It came out in Kylie’s voice, unintentionally. That was going to be a whole endeavour, trying to retrain my voice for when I returned to school, for when my family returned from vacation.

“I don’t want to go.”

“Why?” I said.

“Kylie—Will you be my girlfriend?” he asked. He wasn’t laughing. He wasn’t smiling. His face was dead-serious. His cheeks were red. He was laying himself on the line, putting himself out into an unforgiving place, risking bitter humiliation.

My lips parted but I had no words. I tried to think of something, anything, but nothing came out. Was this another one of his games? A set up for a joke? If it was, he was doing a masterful job keeping a straight face.

He stepped forward and kissed me on the lips, and I knew he was serious. “Please?” he said and I melted. Maybe I was wrong—maybe I could be Kylie. Who cares about right and wrong—does such a thing even exist, really? It’s all just hypothetical nonsense, black and white, right and wrong—who cares?

“Okay,” I said. I couldn’t contain myself. I fell into his arms and he held me tightly. Screw wrong, this felt right. Finally, life felt right.

THE END