[Patreon Exclusive] Roommate Dares: Chapter 2 (Patreon)

I had a bad feeling that I was going to regret taking Jake up on the bet, but I managed to push it to the back of my mind. How bad could it be? One day, in the house. Jake liked to sleep in, and he spent most of his day watching television and playing video games. At the very worst, he would make me do something like rub his feet—which I wasn’t looking forward to, but I had a feeling he wasn’t going to be quite that cruel. I figured I would just be spending the day cleaning up his bedroom, doing the dishes, maybe polishing his shoes.

After winning the bet, Jake left. “I need to pick some things up from the store.” He was out late. I’m not sure when he finally got home—sometime after I’d already fallen asleep for the night.

He woke me up while it was still dark outside. He flicked on my light and said, “Rise and shine, cupcake! We’ve got a lot to get to today, and you’re not even dressed yet.”

I looked at the clock. It was 5:30 AM. Who gets up at 5:30 AM on a Saturday? I rolled over and tried to fall back asleep, hoping he would just leave and try again later. Instead, he came to my bedside and shook me. “Get up—I’m serious.”

With a deep sigh, I sat up. It took a moment for my eyes to adjust to the sudden light in my room. I could see through blurred vision that he was holding something in his hand—a black shirt. No, it wasn’t a shirt at all. It was a dress, with white frills. “What the hell is that?” I said, my voice groggy.

“It’s your outfit for the day.”

As my eyes adjusted further, I took a closer look at the outfit. It was a French maid outfit, probably from some skimpy lingerie store. “I’m not wearing that,” I said.

“Yes you are,” he said.

“No way,” I said.

“You were the one who wanted a no-money bet. You agreed to the terms. Now, this is what you get.”

I tried to think of some excuse out of wearing the stupid little outfit, but he was right: I agreed to the terms of the bet. I should have spent a minute hammering out the details, making sure I wasn’t agreeing to a day of ludicrous humiliation. But I had no excuses, no outs. “Fine, give me the stupid dress.” I said, reaching my hand out for the little outfit. He handed it to me. It was pleasantly soft to the touch, made from satin and lace. Holding it in my hands, I realized how small it was, hardly enough fabric to cover half of my body!

“You’ve got forty minutes to get ready before work starts,” Jake said, and then I realized there was more than just a dress in my room. On the floor was a pair of black high-heels, on my desk was a pair of lacy panties, a pair of lace cuffs, and a lace headband to match the dress. Behind the lacy undies and accessories was a small box filled with makeup and a mound of hair, which I realized was a wig after a few seconds.

“Are you serious?” I said.

“Yeah, you’ll put on all of it. And I don’t want you to do a half-assed job. I want you to get nice and dolled up, like you mean it.”

A cold shiver ran down my spine. I tried protesting again, but the argument led to the same comment. “You agreed to the terms,” he said. I should have just made a stupid money bet. I had plenty of his money still, after all. “I’ll be in my room when you’re ready.”

He left me alone to get ready. I got undressed and then held up the tiny pair of panties. So this was what he was out all night doing? Going around, buying women’s undies, shoes, and lingerie? I looked at the shoes. How did he even find shoes that would fit me? I didn’t have the biggest feet in town, but I liked to think that they didn’t make women’s shoes in my size. I suppose I was wrong.

I slipped the panties on. They were tight, and were hardly able to hold my junk in place. With a sudden movement, my balls would fall out the edge of the tiny strip of lace. Next, I slipped on the French maid dress. Even with no one around to see me, I felt utterly humiliated, though I will admit that the soft satin felt nice against my skin, and I liked the way it felt below the waist, with nothing constricting me in any way (except for the little panties). I’d never worn anything that left my butt open to the fresh air before. Regardless of how it nice felt, it was still terribly embarrassing and awkward.

The dress had pads built into the breasts, as if it was made for women with no tits—or maybe it was made for men who liked to dress up (or for men who lost stupid bets they never should have agreed to).

On top of the makeup kit was a small pack of pink disposable razors. I figured that meant he wanted me to shave. I thought about skipping the shave and hoping he wouldn’t notice (my leg hairs were thin and blonde, and hardly noticeable already) but I didn’t want to end up in another argument that led to ‘You agreed to the terms’, so I took the razors and the box of makeup to the bathroom. I shaved my legs until they were smooth and shiny.

Then, I started with the makeup. I didn’t know what half of the stuff in the box was, so I skipped most of it. I stuck to the self-explanatory items: the eyeliner, the eye-shadow, the brow-filler, the lipstick, the mascara. It was all a lot harder to use than girls made it look. At one point, I poked myself in the eye with the mascara, and it hurt like a son of a bitch.

People had always told me that I had nice, big eyes, but I never really believed them until I was standing in that bathroom, wearing mascara and eyeliner. The added contrast made my eyes look huge, and bluer than they’d ever looked before.

I looked surprisingly pretty with all of the makeup, but I still didn’t look like a girl (which I was quite happy about)—until I put the wig on my head. The addition of long hair seemed to transform me drastically. Suddenly, I looked like a woman (I actually looked a lot like my cousin, who I’d always thought was a babe, though I’d never admit it out loud). Knowing I was probably going to spend the day doing housework, I tied my new hair up into a bun, behind my head, and then I slipped on the lace headband. I was hoping that tying my hair back would take the womanly look away from me, but I was wrong. I still looked shockingly like a woman. Had I not known any better, I would have thought I was staring at a woman through a window, not at myself through a mirror.

I slipped the lace cuffs onto my wrists, a little pink bow around my thigh, and then I stepped into the high-heels. I nearly fell over, the heels were thinner than my pinkie finger. It took a few moments before I was able to stand up straight, and longer before I felt comfortable enough to walk.

Jake knocked at the bathroom door. “It’s been forty-five minutes. Are you ready yet?” he asked.

I looked in the mirror. There was nothing left to do, but I didn’t want to leave the safety of the locked bathroom. As I reached for the doorknob, my heart sank into my gut. I felt so idiotic. Why was I even going through with it? If I just said ‘screw it’, what could he do about it? Take me to court? There was nothing stopping me from taking the little dress off, washing off the makeup, and locking myself in my bedroom for the rest of the day, but for some reason I couldn’t bring myself to do it. I had to honour the bet that I’d agreed to. It was only fair.

I stepped out from the bathroom and watched as his eyes lit up. “Holy shit,” he said. “You—you actually look like a chick!” His lips parted as he looked down my body.