[Patreon Exclusive] HIS NEW GIRLFRIEND: Chapter 2 (Patreon)

It was Monday afternoon, a whole twenty-four hours after the incident at the grocery store when James knocked on my door and a tingle ran up my spine. I considered not answering, pretending like I was out. It had been twenty-four hours of peace, a seventh of my sentence easily served. But I knew if I didn’t answer, James would let himself in. Was the door locked? I couldn’t remember. It didn’t matter. If it was locked, he would have found a window to crawl in through. It wouldn’t have been the first time. So I answered the door. “What’s up?” I said. There was a small glimmer of hope inside of me that James had forgotten about our arrangement. It was a laughable glimmer of hope, but a glimmer none-the-less.

He thrust a piece of paper towards my chest. I took it from him. It was a poster for the Spring Fling, an upcoming dance at his school. “Friday night, baby, you and me,” he said.

That tingle in my spine spread through my whole body. “Huh?” I said.

“You’re going to be my date. I was going to ask Kirstin out, but Brett beat me to it, so fuck her. I don’t need her anyway, seeing as I’ve got you.”

I stared at him for a moment, trying to call his bluff, waiting for a slip—any slip at all. There was no slip. He was dead serious. He actually wanted me to be his date. “You want me to go to the dance with you?”

“Not you as in Kyle, of course. I was thinking you, as in Kylie.” He smirked and that tingle turned into a full-blown tremor. I argued with him and then he reminded me about the tape and that familiar pit in my gut returned. Once again, I didn’t have the option. “But we can worry about that on Friday.”

I thought about it. I knew a lot of people at James’s school, not just James. A few hours in a packed gymnasium was far more risky than a trip to the grocery store on a Sunday night. I couldn’t go a whole night without uttering a word. I would need to work on my voice. I would need to work on my walk, my mannerisms, everything. But like James said, I could worry all of that come Friday.

But the more I thought about it, the more outrageous the idea became. There was no way I could do it, no way I could pull it off. I mean, I didn’t have the most masculine voice to begin with but people would have caught on. There would be, after all, a lot of people I knew there—people who knew me, knew I was friends with James. And if they found me out, it would be insurmountably worse than that tape reaching the internet. Hell, maybe people wouldn’t even watch the tape. “No way. Not doing it,” I said. It had been decided. By a close margin, I would sooner take my chances with the stupid tape than go to the dance with James, dressed up in my sister’s clothing.

“But the tape…”

“Don’t care. Release it. I’m not going to be your slave all week and then go to the dance with you and then do God knows what else on the weekend. This whole bet’s gone too far. Release your stupid tape. See if I care.” I went to close the door but his foot stopped it.

“Okay, fine. Let’s make a deal, okay? You can have the weekend off. Just go to the dance with me.”

I considered it. Maybe I could go the whole dance without speaking. Maybe I could have James tell everyone I was a mute. I nearly laughed at my own thought—no one would buy that in a hundred million years. But there would be loud music there, as long as I stayed near the speakers, no one would be able to analyse my voice. I could show up late and leave early, not give anyone a chance to dig too deep. Besides, I already knew I made a convincing woman from an aesthetic standpoint. Maybe it wouldn’t be so bad. “Just the dance, right?”

“Well,” he said and then he bit his lip. “The dance, yeah, and you would have to come to school with me this week. Just for a bit, though. You know, so that people actually believe me when I say you’re my girlfriend.”

“Your girlfriend?” I snapped. That pit in my stomach turned to nausea.

“Okay, so I told everyone I was bringing my girlfriend from another school. Kyle, you have to admit, you make a hot girl. With a little bit of makeup, everyone in the school will be so jealous of me. C’mon—help a buddy out here.”

I could feel my skin turn from pale to green. I had the urge to slap the bastard but I kept myself under control. “So what are you saying? The dance and what else?”

“Just make an appearance at school with me some day this week. Come and give me a kiss on the cheek. Maybe bring me my lunch—say I forgot it at home. Tell everyone you spent the night—that kind of thing, you know? Make people know you aren’t just my cousin or something lame like that.” Oh, the irony, I thought. This was worse than bringing your cousin to the dance. He was bringing his best friend in drag.

“Not doing it.” Again, I would sooner take my chances with the tape and be done with this whole slave fiasco.

“Do it and I will destroy the tape and I’ll give you my bike. Promise.”

And once again, that damned bike was the difference maker, the buzzer-beater, my Achilles’ Heel. I needed a new bike, and it would have been nice to avoid the release of that tape. So I accepted the deal reluctantly and I became James’s girlfriend for the week.

I cringed at the thought. I’d become James Fischer’s girlfriend.

If I was going to survive the ordeal, I was going to need to practise, I was going to have to really become convincing. After James left, I found myself in my sister’s bedroom, digging through her closet, picking out outfits. My sister had some startlingly sexy outfits that I’d never seen before and I’m sure she wished to keep it that way. For instance, what was she doing with white lace lingerie? What was she doing with a Playboy Bunny outfit? I don’t remember her ever going as a Playboy Bunny for Halloween.

I tried on a mini-skirt that extended down to about my mid-thighs. It was white and black striped, like it belonged in a Parisian café. With it, I matched a pair of black knee-high socks, and a tight black top, once again using one of my sister’s padded bras to create some tits. She had a cute pair of white shoes that completed the outfit. I caught myself posing in the mirror, checking out my ass, my curves. I took a step back and shook my head. Don’t get so into this, I told myself. Don’t fall any further down this hole than you already have.

It was frightening. I could suddenly see why some men liked to put on women’s clothing. It was comfortable. It was sexy. It made me feel great about myself, about my body. For once, my small stature was being put to good use. I may not have been able to play football (like James) or basketball, or any ball for that matter, but I could look like a fox in girls’ clothing.

I shook my head again—again, Kyle, you’re falling too far down, getting too far lost. Get a grip on yourself. In one week, you will be done with this nonsense.

Next I was in the bathroom with a box full of makeup and hair products and accessories. I didn’t know what half of it was, but if I was going to pull this off, I needed to figure it out. Concealer, that was an easy one. Eye shadow—pretty self-explanatory. The mascara was a bit tricky but I figured it out. The deep red lipstick took a few attempts to figure out, too, but I got it quickly enough.

The hair—now that was the real challenge. I’d seen my sister using the curly wand before, but I had no idea how to use it myself. I turned it on and tried to imitate what I had watched her do, to no avail. So I unplugged it and went for the flatiron instead. That was more straightforward. You clamp it closed and run it down your hair. Then your hair is straight—easy. I even discovered that, by twisting the iron as you run it through your hair, you can make big loose curls which looked fantastic as far as I was concerned.

James was right. I was hot. I was a fox. Just staring at myself in the mirror, I got an erection. It popped out from my panties and pushed my skirt out. I tried to adjust it back into the thin, lacy undies, but it just popped back out again. That was something I was going to need to get a handle on. If my erection popped free during the dance, then I was in real shit—far worse than a million masturbation tapes.

But for now I was alone. So I reached beneath my skirt and started to beat myself off. My theory was simple: control it by getting it out of your system. Besides, how could you not jerk off standing face to face with a vixen like me? It was like watching a complete stranger, a gorgeous woman who happened to have a rock-hard erection. She was beating herself off so why shouldn’t I? I came all over the mirror, a giant, white, sticky load all over my beautiful reflection. Watching her cock cum like that made my legs tremble.

A few minutes later, my dick was once again flaccid, and I could continue working on perfecting my female persona. I hit up Google for some tips on how to sound like a woman. It was surprisingly easy. Maybe it was the years of choir-training I had, or maybe it was just that my voice was naturally high, but within an hour, I could do a girl’s voice so well, I could have had my own parents fooled.

I taped myself walking around my garage, practising the voice, and then I watched the tape. And holy shit, I was a woman. I was watching a woman. No one would have ever thought otherwise. The only way I was going to be caught was if my erection sprung out in public—and I was sure that was something I could avoid.

So I went back up to my sister’s room and started to undress. Then, I caught myself in the mirror and hesitated. Maybe, I thought, I needed to really be sure about this, about my persona, before I tried it out in front of people I knew. Maybe I needed to try it out somewhere safe, where if I was caught, no one would know who I was and I could get away without too much humiliation.

I’d never been in a club before. I wasn’t old enough yet. But I’d heard they rarely checked the girls’ IDs. The bouncer would be my first test. The question was, could I trick a whole club full of men?

I picked out a clutch from my sister’s closet—white to match my outfit—and I headed out for a place on the other end of town called Roadhouse.