Timmys New Roommates Pt 01

My name is Tim Howard. I'm a 42-year-old legal secretary who works at a very successful law firm. I'm quite smart and good at my job. Lacking the confidence to become an actual lawyer, I stayed in my position and became quite proficient at it, as it fit my personality. I was naturally quiet and submissive, which made me well-suited for the role of working for top-tier lawyers.

The firm was quite hierarchical, and we were expected to show respect to the lawyers in charge. I was a natural fit, and I did well being ordered around. I was also very precise in my work, which earned me a decent salary. This allowed me to afford a comfortable two-bedroom condo. I lived alone, and as a short, slightly overweight, shy man, I had very little luck with women, or rather, no luck at all. But I learned to accept my virginal, safe life.

Every year, a new crop of young, hotshot lawyers would come in, and one of them, Trent, fit the classic "Greek god" look, complete with a Harvard degree. He was excelling. As good-looking and successful as he was, he was also a super nice guy, even taking the time to talk to me on occasion about sports, as we both liked the same teams.

One morning, he came in upset because a major pipe had burst in his apartment and he needed a place to stay quickly. I had a free room, and thinking it would be nice to have a cool young guy live with me temporarily, I offered up my condo. Trent gratefully accepted. Since he was a young hotshot lawyer, he was out on the town most nights with his successful, high-status friends, but occasionally, he would stay in, and we'd watch our teams together. It was really nice. He wasn't the greatest at keeping the place clean, but I didn't mind cleaning up. It was nice to have some company, even though he never considered inviting me out with him.

About a month into staying at my place, he started seeing a gorgeous 20-year-old girl, Brandy. I hadn't met her at first, as he would only bring her over late at night, after the bars, when I was in my room. I did see her through the window a couple of times. She literally looked exactly like a young Megan Fox--a "mean girl." She was super loud in bed, which would give me a raging hard-on as I quietly jerked off in the other room, like the sad loser I was.

One evening, I came home after going to the grocery store and found Trent and Brandy sitting on the couch, watching TV.

"Hey buddy, this is my girlfriend Brandy. I don't think you two have met yet," Trent said.

I gave a nervous hello and introduced myself as Tim.

"Hi Timmy! It's lovely to meet you finally. I hope I haven't kept you up at night. I'm quite loud during sex, and Trent really brings it out in me."

I stammered a bit and awkwardly said, "It's fine."

"Wow, all those groceries! What are you making for dinner?" she asked.

I told her I had some tuna steaks and asparagus. It was on sale, so I bought some extra to freeze.

"Oh, wow! Trent said you're a talented little chef. Can you make some for us, Timmy?"

"Uh... er... sure," I awkwardly said.

"Oh, yay! Just let us know when it's ready," she said.

Even though I introduced myself as Tim, she went right to calling me "Timmy," which I hated, but of course, I said nothing.

Dinner took me about an hour to prepare, and I added a salad, which I hadn't planned on but thought would be appropriate since more than just myself was eating. Nobody ever offered help as they just sat and watched TV the entire time. I set the table, plated up a serving for everyone, and went out to tell them dinner was ready. Trent hopped right up, saying how starving he was, and Brandy walked by me toward the table, patting my cheek while thanking me.

"Timmy, do you have any wine?" Brandy asked.

She said ice water would be fine. Apparently, along with cooking, I was expected to get drinks as well. I went to grab Brandy's water, and Trent yelled for a beer, which I did have.

"You know, Tim, you really should have a bottle of red and white in the house in case you bring a female friend back ever," Brandy said as I made my way back to the table.

Brandy then spent the rest of dinner inquiring about my love life and why I didn't have a girlfriend. She pressed me about the last time I had sex, which was a resounding never, but I kept giving dodgy, awkward answers until Trent actually saved me.

"Oh, come on, babe, leave the poor guy alone. He just made us this great dinner."

Brandy gave me a devious look. "Okay, fine, I'll leave him be," she said, then paused and gave a wry smile. "For now."

Trent grabbed his plate to clear it, but Brandy stopped him, standing up to kiss him.

"Timmy doesn't mind cleaning up, do you, Timmy?"

"Uh... er, no, that's fine."

"Good boy. Now come on, lover, let's go to bed. I've got lots of energy now."

So, there I was, stuck cleaning up the meal I prepared while they went off to have sex upstairs.

The next run-in I had with Brandy was a couple of days later, on a Saturday. It was around 8 p.m., and I was home alone. Trent had left--apparently, he, Brandy, and some friends had a private table at a hot new club that was opening. I was just happy to have the TV and living room to myself after a long week of work. I was in my sweats with a pint of ice cream when the door clicked open and Trent and Brandy walked in, looking fabulous. She was in a super sexy, short dress with her cleavage bulging out and those super expensive high heels with the red bottoms. The dichotomy between them and me, in my grubby sweatpants with my pint of ice cream, made me immediately self-conscious.

"Hey, buddy, I spilled a damn soda on my shirt. Just gotta make a quick change," Trent said as he ran up to his room, leaving me alone with Brandy. She sauntered over and sat in the sofa chair with a big smile.

"So, Timmy, no hot date for Saturday, I see? Just you and the ice cream?"

"Uh, er, no," I awkwardly said, as she sat comfortably, swinging her crossed leg, reveling in my discomfort. She looked over toward the TV.

"What are you watching?"

"Uh, er, it's Star Wars: The Empire Strikes Back."

She laughed. "Jesus, Timmy, you definitely have the movie tastes of a 40-year-old virgin."

I got red-faced and just awkwardly looked around as this 20-year-old mocked me, and I did nothing. Luckily, Trent came down at that moment.

"Hey, babe, you ready?"

"I guess so, even though I would like to play with little Timmy some more," she said, while standing up to clutch Trent's arm.

Just when they were about to leave and leave me alone in my humiliation, Trent turned back.

"Hey, Tim, you're doing the laundry tonight, right?"

"Uh, yeah, I was planning on it."

"Awesome. Any chance you could throw an iron on that white linen shirt I have? We're going to a wine tasting tomorrow afternoon, and I was hoping to wear it."

Brandy then interjected, "Wait, he does your laundry for you?" she said, chuckling.

"Well, I couldn't figure out the damn machines here, so he offered to help me out."

"Oh, do girlfriends count?" she asked, rubbing his chest. "We were gonna have to leave early and drop off my stuff at my parents' so their maid could do it. But if Timmy could do it, we could spend the morning in bed."

"Hey, bud, any chance you could help a bro out with that?" Trent asked.

"I promise it's not too much, Timmy. It's in Trent's trunk," Brandy said, resting her head on his shoulder.

Of course, me being spineless, I just said, "Sure," and followed the gorgeous couple to the driveway as Trent popped the trunk. I was shocked to see four huge baskets of laundry. Was I really expected to do all this for her? Trent seemed kind of in a hurry and actually came around and started unloading them as I stood there, dumbfounded.

"Uh, is all this her stuff?" I asked, which Brandy heard from the front seat.

"Oh, it's not that much, Tim. I'm sure you can find time during your busy Saturday night of ice cream and movies," she said, dismissing me with a wave.

I just sat there like a loser as Trent got in the car and started backing out. Then he stopped, and the window came down.

"Oh, and don't forget my lingerie is expensive and needs to be hand-washed, Timmy," she said, blowing me a mocking kiss. She started chuckling to Trent as the car sped off.