Darren's Apartment Ch. 01

Chapter 01: Remembering Jenna

This series ties together characters from my Traveler series and my Ben Around series, but it can be enjoyed without having read the other series. I hope you enjoy it.

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"So, I'm moving back to Boston," said Jenna.

Darren was nearly dumbstruck. Never in a million years did he think Jenna would be moving back. She had been living in Baltimore for six years, and during that time, she had only contacted him once or twice a year.

Darren's sister had always been a bit flaky that way. The last time she was in Boston was just after he had moved there. Jenna crashed at his apartment for a couple of months after having city-hopped twice post-college. After a short stay and two failed jobs, she packed up and went to Baltimore.

Given Jenna's history, it wasn't surprising that she was hopping towns again. It was, however, surprising that it took six years for it to happen. It was even more surprising that she called her brother to tell him. She was never good at keeping in contact, and when she left for Baltimore, there was still a little bit of weirdness between them.

There was no use thinking about that now. "Why are you moving back to Boston?" he asked.

"I got a job as a Senior Architect for Lockwood," she answered.

It was a surprisingly good reason. "Good for you, Jenna," he said. "When do you start?"

"A week," she replied. "Can I crash with you for a while?"

A week: that was the Jenna that Darren remembered. It was a wonder that Jenna, who never seemed to plan properly, had succeeded at all in a career that demanded she come up with plans.

"Sure, you can stay here a while," he answered. "I don't live in the same apartment anymore."

"I know you moved, silly," she said.

"Oh yeah? What's my address?"

"I don't remember."

They both laughed. It was a good feeling. It broke the ice. Must be things weren't weird between them anymore.

They exchanged niceties, plans and Darren's real address, and the phone call was over.

There were three of them growing up in Omaha, Nebraska. Darren's eldest sister, Monica, was the organized one. She knew what she wanted and went after it. She pursued finance, married her college boyfriend, Jeff, and they moved to San Diego. Darren had been out to visit a couple of times, since she had moved there, and it was always a good time. Monica was always a good one for setting Darren up with attractive women when he needed to get laid. The last time, it had been a rambunctious blonde from Seattle, named Shannon, who was one of Jeff's business acquaintances.

Jenna never got along with Monica. As the middle child, she was always a bit more of a free spirit, and that got on Monica's nerves. Jenna had three majors before settling on architecture, so, in actuality, she graduated from college the same year as Darren, even though she was two years older than he. She got a couple of false starts in her career, bouncing from Omaha to Dallas to Pittsburgh before attempting to find something in Boston. She was only in Boston for two months and was fired twice during that time.

Darren benefitted greatly from witnessing the successes and failures of his sisters. From early on, he was more level headed than Jenna, but more flexible than Monica. He got along with both just fine. Both of his sisters were attractive, which meant they had attractive friends, which meant that Darren's house was a revolving cast of attractive females to observe. It helped him understand what women want.

Or so he had thought. While understanding what women want, Darren didn't have a natural sense of swagger. He didn't have the confidence of a star athlete or a savvy businessman. He was drawn to technology. He studied programming and became a programmer. By twenty-three, he was already on his way toward a profitable career, and that certainly helped with women, as did moving to Boston, which provided a much higher pay scale. By the time he was twenty-nine, he had moved into a much nicer apartment, a high-rise of about eighty apartments, and he was on the 19th floor.

The apartment was quiet. It was getting to the end of the day. He surfed some porn for a while but found his mind wandering. It had been a while since he had thought about Jenna. His memory took over, even as he continued to stroke his erect cock.

It was six years ago. He was in the living room of his old apartment, a laptop in front of him with a video of a guy going balls-deep into a busty waitress, or flight attendant, or whatever. He didn't remember the details.

He had forgotten that Jenna was in the apartment. Caught up in the moment, he had unzipped his pants, pulled out his dick and had begun to stroke himself.

"Where do I do my laundry?" Jenna was saying as she entered the room. "Oh shit!" she exclaimed. "Are you jerking off?"

Darren closed the lid of his laptop. In his panic, he neglected to cover his exposed cock. He was at a loss for words. Jenna was wearing some form-fitting low-rise jeans and a black t-shirt with no bra. She was barefoot and her auburn hair was a bit messy, as opposed to the way it usually was well groomed. She looked comfortable. She looked sexy.

"You fucking pervert," she said, stifling a giggle.

"Jenna," he said. "I'm sorry. I forgot you were here."

She bit her lower lip. Darren was surprised that she still hadn't run from the room in horror. "Just jerking off to some porn, then?" she stated the obvious.

Darren nodded.

"Is it good?" she asked.

He couldn't believe she was asking about what she caught him doing. She was certainly not willing to just let him get away with it. He lifted the lid of the laptop to show her the video.

"No, no," she said. "I don't need to see it."

Phew. Darren took this to mean she was giving up on making him uncomfortable.

"Describe it to me," she said.

Shit. She wasn't going to let this go. Every moment she remained in the room was another moment of awkward discomfort for Darren. If only his erection would subside, he could zip up and walk out, but it didn't go away. He was inexplicably aroused.

"Describe the video?" he asked.

"Yeah," Jenna said. "Who's in it?"

"A man and a woman," he answered simply, as if that was going to make her stop asking.

"Yeah?" she said. "What are they doing?"

Darren couldn't help but laugh a little. "They're fucking," he said. "What do you think they're doing, making tea?"

"How are they fucking?" she asked. "On the table? Against a wall? In the shower? Is it missionary?"

"He's fucking her from behind."

"Ooh," Jenna said. "You dirty man. Do you like that? I do."

"Yeah," said Darren. "I like that."

"What does he look like?" she pressed. "Does he have a big cock?"

"Yeah," Darren answered. He had given up trying to get away from her questions. "It's pretty big."

"Is he as big as you?"

"I think so."

"Yours is pretty big," she commented.

"Thanks, I guess."

She leaned against the TV cabinet, her arms folded across her chest, looking intently at his cock. "Do you like watching a big, hard cock slide in and out of her?"

"Yes."

"Makes you want to stroke yours, doesn't it?"

"Yeah, usually."

"But not right now?"

"No."

"Why?"

"Jenna. Are you kidding?"

"Don't you just want to reach down and touch yourself? Don't you want to imagine you're that guy? Don't you want to feel like you're sinking your hard dick into her pussy?"

Darren didn't know what to say or do.

"What about the woman?" Jenna asked. "What does she look like? Is she blonde? Brunette? Redhead?"

"Sort of brunette, I guess," he answered.

"Sort of?"

"Brunette with some red."

"So, auburn, like mine? I'm flattered."

Shit, Darren thought. Now she thinks I'm fantasizing about her. Am I?

"It's okay," she said. "I guess it would be alright if you touched yourself. It's perfectly harmless."

"I don't want you to see me do that?"

"Why not?" she said. "You have it out. It's hard."

"You're my sister. It's weird."

"So?" she laughed.

"Stop fucking with me, Jenna. This is weird."

"Sure it's weird," she said, "but you keep looking at my chest, don't you, you big perv?"

"You caught me in a compromised position here," said Darren. "This isn't my fault. I didn't ask you to stand there while I'm hard."

"You don't have to stare at my tits either."

"I'm not st—"

"What about her tits? Are they my size?" she asked. Her hand ran under her black T-shirt, lifting it, exposing her belly button.

Somehow Darren's dick stiffened even more. "I'm not sure if they're the—"

Jenna's hand moved upward, pushing the shirt up as she cupped her left breast. Her fingers slid over the underside of her breast, lifting it, then over her nipple, which peeked between her knuckles. She continued over the top, lifting the shirt as she went and exposing her full breast.

Darren couldn't help himself. She looked so good. He was so turned on. His hand began to move to his cock.

Jenna giggled. "You are such a perverted fuck," she said. "Go ahead. I don't mind."

Darren wrapped his hand around his stiff cock and started to slowly stroke it.

"Mmm," she said. "How does that feel?"

"It feels good," he replied.

Jenna fondled her breasts through her shirt with one hand, as the other slid down her abdomen and under the waist of her jeans.

"Do you like jerking off for your sister, you dirty fuck?"

His eyes scanned her body. "Yes."

"Does it make you hard when I play with my pussy?"

"Yeah. You look—"

"I look what? Do I look hot?"

"You look fucking sexy." His pace quickened.

"I can tell," she said. "Jerk your hard dick for me, brother."

"I'm so turned on."

"More than the porn you were watching?"

"Yes. You look so good."

"Are you gonna cum for me?" she asked.

Did she really just ask that? He had avoided thinking of her this way for so long. He knew she was hot, but she was his sister. They weren't supposed to be doing this.

"I feel like I'm gonna cum," he said.

"Mmm. Fuck. Yeah. Stroke your big hard dick for me. I want to see you cum."

She certainly knew how to talk him into things. His face went red. His balls tightened and he began to shoot white streams from his cock.

"Fuck. That felt so good," Darren said aloud.

He opened his eyes. There was no Jenna. There was no TV cabinet. This was a different apartment and six years had passed. He wasn't twenty-three. He was twenty-nine.

And in only a week, Jenna was going to come.