[Patreon Exclusive] Roommate Dares: Chapter 4 (Patreon)

The Canucks lost the game badly and I won the bet. Jake was too upset with the outcome of our wager to continue making commands for me. He had me make him dinner, clean up the dishes, and then he said, “That’s enough for the day,” and he went into his bedroom for the rest of the night.

In a strange way, it was kind of disappointing, taking the little French maid outfit off, pulling off the wig, and washing off the makeup. In minutes, I went from looking sexy and full of energy to being my regular, old self with shaved legs. It was too bad men couldn’t wear makeup out in public. I looked way better with that eyeliner along my eyelids, and that mascara bringing out the blue of my eyes. The makeup did such an amazing job bringing out all of my good qualities. Without it, I just looked like… me.

I slipped back into my regular clothes and then started thinking about what I was going to do the next day, now that I got to be the master and Jake was going to be the slave. I sat and thought for a while. There were hardly any chores left to do around the house—the house was already cleaner than it had ever been before. And would I dress him up in the French maid outfit and the makeup, like he did to me? We were about the same size—it would all fit. If I didn’t, how could I match the humiliation? How could I get adequate revenge?

I looked over at the small pile that I’d spent the whole day wearing. How could I one-up him?

I had an idea. I grabbed my wallet and headed down the street, to the little sex-toy store where I can only imagine was where Jake went for the French maid outfit. They had just what I was looking for: a remote-controlled, vibrating butt plug. It was embarrassing, buying the little device, but it wasn’t nearly as embarrassing as spending my whole day down on my knees, in women’s lingerie.

I could hardly sleep that night, thinking of all of the things I was going to make Jake do. I even ended up waking up before my 5:30 AM alarm, full of energy, ready to make Jake’s life a humiliating hell, the same way he did to me.

“Rise and shine, beautiful. Time to get ready for the day,” I said, holding up the little French maid dress, the same way he did when he woke me up the morning before.

He groaned and rolled over. “Fuck,” he said, knowing there was no way out, seeing as I’d followed through with everything he’d asked from me. Now it was his turn. I handed him the dress and the wig and said, “I’ll see you in forty-five minutes.”

From the living room, I watched him walk from his bedroom to the bathroom with his outfit in hand. I couldn’t wait to see how he looked. It was a long forty-five minutes in anticipation, especially at six on a Sunday morning, when even the morning news wasn’t on. I watched hockey highlights from the night before, reminding me of my sweet victory.

After forty minutes, I went and knocked on the door. “I forgot something,” I said.

“What?” he called out from the other side of the door.

I opened the door slightly and placed the butt plug on the counter. “Put that in your ass,” I said.

“Are you kidding me?” he said.

“Hey—stay in character, or there will be punishments,” I said, unable to keep the grin from my face. I made a point of not looking into the bathroom, not wanting to spoil the surprise until he was fully ready and dolled up.

When he finally emerged from the bathroom, he had a long frown on his face, probably because he knew he looked great—just like when I was in the very same outfit. It fit him perfectly, making his tush look great and his legs long. He didn’t seem to have nearly as much trouble with the heels as me. “You look beautiful,” I said with a laugh, though I wasn’t really kidding. Before he emerged, I wasn’t sure what to expect—whether he would look good or like a man in a dress. Was it a coincidence that Jake and I both looked like convincing ladies when in drag, or was there something special about that dress and that wig, that had the power to make any guy look like a sexy girl?

I wondered if he had the butt plug in. There was no real way of knowing, without asking him to bend over and show me, and to be honest, I didn’t want to see his asshole or anything under his dress for that matter. I was enjoying the female-illusion and I didn’t need anything to ruin it.

“Let’s get right to it, shall we?” I said.

I started him at the bookshelf. For the longest time, I’d been meaning to rearrange all of our books into alphabetical order, based on author names. He dropped down to his knees with a sigh and started to pull the books out.

“Let’s hear your best girl voice,” I said.

I heard him let out another reluctant sigh. “How’s this?” he asked.

His voice was surprisingly great—again, without much effort. Maybe there was something about the outfit that really did bring a man’s femininity out.

He kept trying to pull the skirt of his dress down, to hide his bare rump, but it was especially hopeless once he got down to the bottom shelf and had to bend down all the way. Between his bum cheeks, I could see a slight bulge in his panties. It was the base of the butt plug—he really did have it in his ass!

I took the remote and turned it on, making it vibrate in his rear-end. His body became tense for a moment, his toes pressing out. “Keep going,” I said, biting my lip to stop myself from laughing. I slowly turned up the power of the vibrating butt plug as he filled the shelf with books.

He started to slow down once I had the plug up to it’s middle setting. He took a deep breath and then let a little, “Oh fuck…” slip out, under his breath. I decided to turn the butt plug off for a little bit. It was still early in the morning, and I wanted to get a lot more out of him yet.

Next, I had him cook me a late brunch: waffles and bacon, with a side of neatly sliced fruit. While I ate, I made him reorganize the fridge and clean the shelves. It was starting to seem like he was getting more comfortable in his new role. Either he got sick of pulling his dress down or he just stopped caring if I could see his butt, but he stopped tugging it down while he bent over, focussing his attention on the task at hand.

He bent over cutely, keeping his legs straight, his feet close together, and his butt perked out. I don’t know if he was doing it on purpose, trying to tease me the way I teased him the day before, or if that was just the way he naturally stood in heels. Standing in heels is very hard, after all—but they made his legs look great.

I was surprised that he hadn’t made me rub his feet the day before. So after the brunch dishes were cleaned up, I asked him to grab a bottle of moisturizer and meet me at the couch. I had him sit on the floor while he held up one foot at a time, rubbing gently at first and then really pressing, getting in deep. He was pretty good at giving foot massages. He managed to get right in-between my toes, relieving tiny pressure points I didn’t even know I had. Instead of massage oil, I had him use moisturizer (because we didn’t have any massage oil).

As he rubbed away, I let my head rest back against the couch while I thought of what I could get him to do next. Finished with my feet, he started to rub my calves. “How’s this, master?” he said.

“That feels nice,” I said. I felt like he was going to massage me to sleep, I felt so relaxed. I hardly noticed him working his way up to my thighs, running his hands up and down my still-smooth legs, spreading moisturizer. His fingers gently crept up the legs of my shorts and found the bulge of my cock. He started to rub.

I looked down at him. He was looking into my eyes, smiling devilishly. He continued to rub my cock carefully, stroking it between his heavily-moisturized fingers, getting it hard. I let out a deep sigh.

I forgot for a moment that he wasn’t actually a woman, that he was my roommate—and had been for over a year. And now he was rubbing my cock, getting me erect, and I was doing nothing to stop him. The day before was repeating itself. I bit my lip, trying to overcome the pleasure, to put an end to the act, but I couldn’t do it. Instead, I reached into my pocket and pressed the button on the little remote, turning the vibrator back on in his asshole. His body perked up and his eyes opened wide.

He had beautiful green eyes that I’d never even noticed before he had a full face of makeup. He had nice, full lips, too. He pulled down my shorts, taking my boxers with them. I was suddenly tense, my shoulders up near my ears, my heart pounding viciously. It was as if I’d lost all my sensibilities. I bit my tongue hard.

I had to put an end to it before we got carried away.