[Patreon Exclusive] Roommate Dares: Chapter 3 (Patreon)

He was unfortunately right—I did look like a chick—that was the worst part of it all. At least if I had looked ridiculous, we could have just both laughed it off. It could have been a funny memory. But instead, I looked kind of sexy, and to someone who didn’t know any better, I would have looked totally genuine. It was a good thing we agreed to keep everything within the confines of the house, because I could tell Jake was getting some ideas as he stared at me. He would have loved to set me loose in a bar full of drunk men to get hit on and slapped on the ass. A nausea overcame me. What if he invited friends over to see me? There was nothing in the rules against others coming into our house for the day. I thought about asking him not to invite anyone over, but I didn’t want to give him any ideas, so I kept my mouth shut.

“What do you want me to do?” I asked, feeling stupider and stupider with every passing second.

“Well first, I want you to start speaking like a lady. It’s a real turn off when you speak with that deep voice,” he said. My voice wasn’t naturally deep, but I suppose it was deeper than a woman’s voice.

“Seriously?” I said.

“Seriously,” he said. “You have to do everything I say today, remember?”

After a deep sigh, I did my best girl’s voice. “How does this sound?”

His eyes lit up. “Surprisingly good. Where did you learn to do that?” he said.

My heart sunk further into my gut. My girly voice sounded shockingly genuine. But where did I learn to do that voice? I had no idea. I’d never done it before. It wasn’t like I’d ever practiced doing a woman’s voice. It was just… natural.

“Oh, and you’re going to call me master for the rest of the day,” he said. “And I want you to stay in character. No breaking character, or there will be punishments.”

I bit my tongue. “Yes, master,” I said, sticking to my girly voice. I didn’t want to find out what punishments he had in store for me, so I stuck to my character. I couldn’t keep my focus away from our windows, which were open. In a few hours, our neighbours would be waking up and all they would have to do is look towards our house to see me prancing around like a girl, in lingerie and heels. It was bad enough that Jake saw me all dolled up. The last thing I needed was to have the neighbours peering in through our windows. “What can I do first for you, master?” I said.

“The dishes haven’t been done in a few days. Why don’t we start there?” Our dishwasher was broken, so I was stuck doing almost a week’s worth of dishes by hand, scrubbing each one while Jake sat at the table behind me, reading the newspaper. I kept reaching back to tug the skirt of my dress down. It just barely covered my ass, and if I gave it a minute or two to ride up, my whole ass would be out.

Putting the clean dishes away was the real challenge, in those skimpy high-heels. I nearly fell over a few times, trying to stand up on my toes to reach the upper shelves, but I got the hang of it near the end of my hour-long dish-washing marathon. “What’s next, master?” I said.

“The house needs a good vacuuming,” he said with a grin.

So that was what I did next. I started in my own bedroom, being sure to get under the bed and in the corners, and then I made my way into the living room. He sat on the couch, watching the television as I vacuumed around him. I was standing right next to him when he said, “Be sure to get under the coffee table.” I had to bend over to get under it, which was especially embarrassing because I knew he could see right up my dress, at my mostly-bare ass. He gave me a little slap, making me jump. “Good girl,” he said with a laugh.

He seemed to know just how to make the whole experience especially humiliating. I looked to the clock, hoping hours had flown by and the day was nearly finished. But it was only nine in the morning—a whole day of being Jake’s lady-slave still ahead of me.

As I continued to vacuum the house, I noticed Jake in the window reflections, staring at me with that grin on his face. I’d seen him win thousand-dollar bets before, and he didn’t nearly look this satisfied.

It was around noon, and I was dusting, that I looked back at him and saw him holding up his phone camera. “Smile,” he said with a laugh. I felt all of the colour rush out from my face.

“What are you doing? Delete that,” I said, reverting to my natural voice.

“Hey, no breaking character!” he said.

I took a deep breath and said it again, this time in my girly voice. “Delete that video, master,” I said.

“I’ll delete it at the end of the day,” he said, slipping his phone into his back pocket. “Now you have a good reason to follow all of my commands.” His grin grew even bigger. “I’ll let that last little slip slide, but from here on, you’ll be punished.”

If that video got out, my life would be over. All of my friends would mock me endlessly. I would probably end up on some viral video website, unable to find a job for the rest of my life. And my God, the thought of my parents seeing that video… I’d sooner be dead.

“What’s next, master?” I said, reluctantly.

“The hardwood needs a good polish,” he said. He went over to a grocery bag and pulled out a bottle of hardwood polish that he must have bought the night before. The whole day had been meticulously planned out. With a sigh, I took the polish, got a rag, went down on my knees, and I started scrubbing the floor with the polish, starting in the corner and working my way out. It was especially humiliating, being on my hands and knees in a piece of women’s lingerie, but at least the house would be cleaner than ever.

I looked over my shoulder at one point and caught him staring at me. He looked away swiftly and pretended like he hadn’t been staring at all. It almost seemed like he couldn’t help it, like he was actually a bit attracted to me. I couldn’t entirely blame him. Every time I caught my own reflection in, I was surprised by how good I looked. Hell, I looked sexier than most of the girls at my work, and apparently I had a physique women killed for. With my legs shaved and smooth, I looked like I could have been a leg model, for crying out loud.

Making the most of my situation, I decided to have some fun. I started teasing Jake. “How does it look, master?” I asked as I continued to scrub the floor on my hands and knees, my exposed butt facing him.

“It looks good,” he said, his voice cracking slightly as he said it.

Next, he had me dust the counters and tables. As I went to dust the coffee table, I made sure to bend over far, getting my tush right near his face. I heard him take a deep, controlled breath in. When I turned around to face him, his cheeks were red. I did my best not to giggle, realizing I was right—he really was infatuated by me. “What’s next, master?” I said, standing over him, looking down.

“My bed needs made,” he said. “And I could probably use some clean sheets.”

I went to his bedroom and started to strip the sheets off of his bed. He came and stood in the doorway, watching. “You know, you actually do look like a girl,” he said with an awkward laugh.

“Because I am a girl,” I said with a grin, keeping in character. I was getting carried away with my character, getting too much of a kick out of his sudden attraction. It was kind of nice, feeling like the centre of attention, having him swoon over me the way he was. I’d never had anyone swoon over me before.

“If I didn’t know any better, I would believe it,” he said.

As I bent over the bed to pull the sheet over the mattress, he stepped up behind me and put his hands on my hips. “You have the curves and everything,” he said.

“What? Do you like it?” I said.

He ran his hands down to my thighs, and then up, this time going under the skirt of my dress. “Yeah,” he said. He took a deep breath. He took my panties gently and slipped them down.

“What are you doing, master?” I said.

“Shh,” he said, bringing my panties down to my knees, letting my cock and balls hang free. He brought a hand up to my butt and gently ran his fingers along the curve of my rump, ending with the tip of his thumb at my asshole. “You’re tight,” he said.

My heart was racing. I don’t know why I was letting him go on. I don’t know why I wasn’t protesting—or saying anything at all. I just remained frozen, bent over the bed, as he gently caressed my ass, and carefully ran the tip of his finger around the rim of my asshole. After a deep breath, I was finally able to say, “Stop. This isn’t a good idea.” But my body remained frozen, putting up no fight.

He undid his belt and then unzipped his fly. “You agreed to do anything,” he said, and then I felt his big, warm cock press up between my butt cheeks. He was throbbing, already erect. I could feel his thick veins pulsing, pumping blood into his solid rod. “Just be quiet,” he said. “And don’t tell anyone about this.”

I felt the tip of his cock press up against my tight hole. I closed my eyes. Still, I put up no fight. The bet had gone way too far, but I was letting it go on. Why? Why wasn’t I stopping it?

He pushed in, penetrating my virgin asshole. I clenched tightly and then his hand found the centre of my back. “Just relax,” he said. I took a deep breath, gave the muscles in my body a moment to relax, and then he slid in deep, stretching my tight hole wide. His cock was much bigger than I ever imagined it to be (not that I had ever imagined his cock before). I could feel every single inch of it, sliding in, throbbing warmly. It was a weird feeling, being stuffed completely.

He started to thrust slowly, breathing heavily as he did so. “Fuck, that feels good,” he said under his breath.

It didn’t hurt, but it didn’t feel good either. It just felt… strange, like a heavy pressure in my rear-end, plunging me over and over. “Oh shit,” he muttered. He started coming down harder, sinking his entire length into my body, pressing his pelvis up against my tush.

Suddenly, he hit a spot that sent a jolt through my body. I became tense, overwhelmed by a warm tingling. “Right there,” I said as the euphoria filled my body. His angle was just perfect. I don’t know what he was hitting, but it felt amazing—and now, he was hitting it over and over. My cock started to become erect. “Harder,” I said.

I melted into his bed. The pulsing euphoria grew stronger and stronger until I couldn’t handle it any longer; I started to moan uncontrollably, rolling my head from side to side. He grunted with every swift penetration. He slapped my ass and then grabbed a handful, squeezing tightly. “Fuck, you’re so fucking hot,” he said.

“Fuck me, master. Fuck me harder,” I said, pushing my tush back into his hard pelvis, getting as much of his cock inside of me as I possible could.

“I’m going to come,” he said.

“Come in me, baby. Come in me!” I said.

He grunted loudly and then he filled me up, his hot load blasting out in huge waves. I screamed, my fingers curling into his bed sheets.

He stepped back and I felt it rush out, his big, hot load. I remained on the bed for a moment before peeling myself up. The room was silent for a few minutes as we both caught our breath, and then he said, “Better put a fresh sheet on.” He left me alone in the bedroom after that.

I couldn’t believe it—I’d just let my roommate fuck me in the ass, while I was dressed up in a little piece of skimpy lingerie. What had gotten into me? And now that we’d fucked, how could I ever look at him the same? Would we ever talk about it, or were we just going to pretend like the act never happened? It must have been equally embarrassing for him—if not more embarrassing—seeing as he was the one who initiated the sex with his male roommate.

When I finished with his bedroom, I returned to the living room to get my next order. Jake was sitting on the couch, watching the pre-game show for a hockey game that was about to start. “What can I do now, master?” I said.

“Make me some lunch. I’d like a ham sandwich, with lettuce and tomato, mayonnaise and mustard, but no crusts,” he said.

I looked at the television. “Who’s playing?” I said.

“The Capitals and the Canucks.”

“I bet the Capitals take it,” I said.

He looked at me with a sudden grin on his face. “What do you want to bet?” he said.

“How’s about the same as yesterday,” I said. The room became silent. It was my chance for revenge, and he knew it—he knew I would be going just as hard on him as he went on me, but I could tell that only made him want to take the bet more.

“Deal,” he said. He watched the whole game from the edge of his seat.