[Patreon Exclusive] HIS NEW GIRLFRIEND: Chapter 1 (Patreon)

It was a stupid bet, a bet I never should have made. Of course the Leafs were going to lose against the Penguins—why did I think otherwise? Because the odds were good, that’s why—too good to turn down. But Goddamnit, I should have turned them down.

Had I won, James would have given me his brand new bike. His grandma got it for him for his birthday, and it was probably worth close to a thousand dollars. I needed a new bike, and the one I was in the market for wasn’t nearly as nice as James’s. I know, I know—I know what you’re thinking. You did all of this for a bike, Kyle? Yes, I was an idiot. I really thought I was going to win.

The Leafs were on a winning streak. Auston Matthews scored four goals in his debut for crying out loud, and Crosby was out with a concussion. Besides, I really didn’t think being James’s slave for a week would be so bad. My school was on spring break and his wasn’t until the next week. I figured, even if I lose, I’ll really only have to be his slave evenings and the weekend. Had I known he would drag me to school with him, maybe I wouldn’t have taken the bet. But I did, and I lost. Now, I was bikeless and a slave.

How bad could it be, right? James and I had been friends for years, since the first grade, back when we were still in the same school. He wasn’t out to torture me… Or so I thought.

The moment that horn sounded and the Leafs formed a line towards their locker room, heads down in defeat, my heart sank into my gut. James had a smirk on his face that suggested he already had the whole week planned out in great detail. And I was about to find out with certainty that he did indeed. “You officially belong to James Fischer,” he said to me, that smirk still resonating on his face.

How bad could it be? How bad could it be? The question was pinging around my skull. How bad could it be?

“Look,” I said. “We need to set some ground rules. I’m not eating dog shit off of the ground or anything like that.”

“Nothing harmful,” he said. “That’s fair.”

“And I’m not giving you my money or buying you anything. I’ll go to the store for you—fine, whatever—but it’s with your cash. Got it?”

“Sure. But you will go to the store for me when I want you to,” he said. That smirk got bigger. What had I gotten myself into? Goddamnit. He had something on his mind, something bad. I took a breath. I was psyching myself out.

I learned a lesson from all of this, I really did. That lesson was: there’s no shame in backing out of a bet, breaking a promise. I know that sounds bad, but believe me, sometimes it’s better that way. Don’t be stubborn like I was. I learned another lesson, too: don’t make bets with James Fischer.

“Why don’t we start with that?” he said. “Go to the store and get me a bag of chips. Right now. I like Dill Pickle, Lays.” He handed me a five dollar bill.

“Alright, fine.” I stood up and started towards the door.

Then, he said, “Wait!” and I stopped. That smirk—that godforsaken smirk. There was more. And in that instant, I regretted my idiotic bet. I even started to regret our whole friendship. “I want you to go in one of your sister’s dresses.” He was biting his lip, containing his laughter.

My legs trembled. “Are you crazy? No way.”

Then his smirk vanished and he became very serious, brow lowered, eyes dark. “Don’t back out on this bet! You lost fair and square, and you agreed to the terms.”

“I’m not going to the store in my sister’s dress.”

“Why not,” he said, that smile returning. “You have that long, beautiful hair. Why not compliment it with a nice dress.” He laughed. Now I was regretting growing my hair out. And for the record, some of the coolest men in history had long hair. Vikings had long hair. Every member of Led Zeppelin had long hair. Scott Hartnell had long hair, too. There’s nothing wrong with long hair—but I digress.

“I’m not doing it. But I’ll go get your damned chips.” I turned back towards the door.

“Don’t do what I say and I’ll show everyone that clip,” he said.

I froze. I’d forgotten about the clip—that fucking clip. A few years back, James came over to my house, unannounced, and burst into my bedroom with a video camera. He caught me with my dick in my hand and some bouncing jugs on my computer screen. So what? Every teenager masturbates—it’s not like I was doing it out on the street, or watching kiddie porn or anything like that. I was alone, in my room. And at least once a week since then, James used that video for his own bidding—blackmailing me over the smallest things. I was already practically his slave, even without the damned bet. Thank God we didn’t go to the same school. That would have been a real nightmare.

What choice did I have? At least at the store, chances were no one would recognize me. If James put that video out, all of my friends would see it. All of the girls in my school would probably catch wind of it. I would be ridiculed and outcast. “Let’s go pick out a dress, shall we?” he said.

“Fine,” I said. “But after this week, that tape is destroyed.”

“Deal,” he said.

My older sister was in college, and for Spring Break she’d gone off to Cancun with some friends. Meanwhile, my parents were in Cabo. I had the house to myself for the week, and thank goodness for that. The last thing I needed was to have my sister or parents walk in on me trying on a dress.

“This one,” James said, picking out a black, skin-tight number. “You’ll need a pair of shoes, too. Lets hope your sister has big feet.” My stomach turned. Unfortunately, my sister’s feet were probably around the same size as mine—maybe a size smaller, but not small enough that I couldn’t cram them into her shoes. He pulled a pair of black wedges. “I think we have your outfit for the ball, darling,” he said and then he laughed. Looking at the outfit, I started to wonder just how bad it would be if my whole school saw that tape. I mean, it’s not like you could see my cock in the footage, just my back and a flash of porn on the screen before I clicked away. Maybe no one would care—maybe they would all understand. Yeah right, and maybe I’m a Chinese jet pilot. “I’ll give you a minute to change,” he said, and he left the room.

I stared at the outfit. My whole being was rejecting the thought of putting it on. But Goddamnit, I had no choice. I wanted that tape destroyed once and for all. I slipped out of my clothes, even taking off my boxers (knowing they would just bunch up in the tight outfit, which would draw more unwanted attention to me). Then, I stepped into the dress and slipped it on. After I’d pulled the straps over my shoulders and awkwardly reached around back to zip it up, I looked into my sister’s full-length mirror. The damned thing fit perfectly. Damn my small stature, I thought. If only it wouldn’t have fit, then maybe James would have found some other punishment for me—something less humiliating (though, knowing James, that was unlikely). The only issue with the dress was the bulge of my cock. It was so tight that you could see the entire contour of my manhood, pressed firmly against my leg. I tried to tuck it, but it was just too obvious. Also, I clearly had no tits—I was as flat chested as a teenaged boy, unsurprisingly because that is exactly what I was.

My heart continued to burn inside of my turning gut. I couldn’t believe I was actually going through with this nonsense. But I had an idea that would make it somewhat tolerable: if I actually looked like a girl, no one would recognize me. At worst, they’ll think I’m my sister. We looked somewhat alike, some similar features (we were made from the same parents, after all). Or they would think I’m some chick that looked like my sister. But if I could pull off an authentic female look… First I needed to address the bulge.

I slipped a pair of my sisters panties on. They were tight, but they did they job, firmly tucking my cock and balls away. Creating tits was even easier. Apparently (and I had no idea until that very moment), my sister’s bras were all heavily padded. I didn’t even need toilet paper to look like I had a solid pair of B-cups. Luckily, the dress didn’t show any cleavage, so no one would suspect a thing. I looked back into the mirror. Damn. I was actually pretty convincing. I couldn’t grow facial hair to save my life (thank God for Swedish parents!). I thought about putting on some makeup, to really sell the effect, but I didn’t think it was necessary. I already looked terrifyingly like a chick. Without makeup, I was a solid six—totally mediocre, no risk of turning any heads. I wasn’t looking for attention after all, I was looking to blend in to the crowd. To get the job done as quickly as possible, with as little attention as possible.

“You done in there or what?” James called out. “I’m coming in.”

He stepped into the room and his eyes lit up. “Holy shit, Kyle!” he said. His jaw dropped. “You—you actually look like a chick! Damn, son. What’s the fun in that?” He laughed.

“Laugh all you want. Once you’ve got your chips, this is coming off.” I walked past him, straight for the front door. I didn’t wait around for him to add any more ridiculous conditions onto the bet.

It was a few blocks to the store, which gave me some time to figure out the wedges. They were only a couple of inches tall, but I felt like I was walking on drywall stilts. It was a long way to the ground, and I was far from stable. I must have looked drunk to all of the cars that zipped past. But by the time I reached the store, I had a good stride down.

My sister always watched that show, America’s Next Top Model. I’d been in the room a few times while she was watching it. On one episode, the host said something about walking as if you were on a tightrope when you’re in heels. I tried it out, stepping one foot in front of the next. I caught my reflection in a large window, and it looked pretty good. I think I was selling it.

Once in the store, I went straight for the chips, wasting no time. With his stupid Dill Pickle chips in hand, I made my move for the checkout. There was only one line open, and there were about five other people in the line. Damn. I was going to have to wait. I thought about stealing the chips, just walking out with them. I mean, I wasn’t exactly identifiable in my outfit. But what if I was caught? They would have realized pretty quickly that I was actually a man. It wasn’t worth the risk. So I stood in the godforsaken line.

A couple of minutes passed by. There were still a few people before me in the line. Another man had came up behind me and was waiting with his single microwave dinner on the belt. I made a point of not making eye-contact with him or anyone. Avoid attention at all costs—that was my new mantra.

Then, he grabbed my ass. It was a gentle grab, discreet, with his full hand. He got a good handful before pulling away. I leapt up and nearly screamed, but I contained myself. My voice would have been a major giveaway, and then everyone around me would have been staring at me. Hell, I think the guy in front of me lived just two doors down from me, his daughter went to my school. I had no intentions to go down that road. No way.

I looked back at the man and he winked at me. He was older than me by a good fifteen years—a full stubble beard and dark hair. He was maybe handsome by a woman’s standards, but who am I to say? I probably should have been disgusted but I was in too much shock. His grope was a confirmation that I was successfully disguised as a woman. Not only that, but apparently I was a gropeable woman. I bet a lot of ladies go their whole lives without being groped by strangers in grocery stores, and maybe that’s a good thing, but after just fifteen minutes, I wasn’t one of those ladies.

I bought James’s chips and left. I could feel the man’s gaze locked on my ass as I left.

Some energy inside of me erupted. I’d just gotten more attention in fifteen minutes as a woman than I had in my whole life as a man. Talk about feeling conflicted. I mean sure, it was negative attention. No woman wants to be sexually assaulted like a piece of meat. But damn, it felt good to feel attractive, to know that people noticed you, and not just noticed but admired.

I wasn’t even across the parking lot when I noticed James standing there, laughing. He’d followed me. He’d been watching from the window the whole time. “Hey there, Kylie! That guy slapped your ass! Holy shit!” He held his sides and nearly fell over in hysteria.

“Take your damned chips,” I said, thrusting the bag into his chest. I hated his satisfaction. Hell, I bet if he put the dress on and did the same thing, no one would have considered slapping his ass. Deep inside of me, it was almost a point of pride, a silver lining. But at the same time, I couldn’t wait to get out of the dress. So I continued on towards the house and the moment I was inside, the dress came off and my jeans and t-shirt came back on. I was just happy it was all over. At least I thought it was. But oh, how naïve I was.