How I Became a Cad

Thanks to Wicked Inside for editing & feedback. Thanks to everyone in the forums who provided valuable feedback on my first story, The Coldest Night of the Year.

*****

MONDAY

I should have known better than to take a summer internship that my stepdad had gotten for me. He was less interested in improving my resume than he was in getting me out of the house. But my options were limited. By limited, I mean I had exactly one. It was May, ten years ago, and I had just finished my freshman year at college.

The internship was in a nameless office park in the middle of some godforsaken suburban wasteland out past the airport. It was one of those places where Chipotle passes for Mexican and Starbucks for coffee.

The guy I was subletting from was some sort of engineer who'd gone back to China for a funeral, or a wedding, or maybe just to spend a couple of months eating real Chinese food. I had no idea, but the place felt like a CIA safe house - nondescript, cheaply furnished, and in the shadow of an on ramp.

I made the bold decision to walk the two miles to work. I'm pretty certain I was the first person to actually walk on some of those sidewalks. Did I mention it was hot? It was hot as fuck.

I arrived at the office park. The developer who had thrown the whole mess together had been too embarrassed to put his name on it. The building itself was a glass box. It was gray and grimy-looking. I suspected it had been gray and grimy-looking the day the building was completed. I was feeling like I'd already done a full day's work on an Alabama chain gang.

I entered the lobby. I was hit by a blast of AC that froze my sweat-drenched shirt to my body. I found my employer's name next to the elevators: Fletcher Freight, Suite 701.

When I hit the seventh floor, the elevator opened onto an empty reception desk. I wandered behind the desk, looking for a cubicle dweller who could help me find my new boss. I almost caught the eye of a man at standing next to a laser printer, but he started fiddling with the buttons so he wouldn't have to make eye contact. A woman next to the coffee machine started sorting the K-cups.

At this point, a short woman in a unflattering business suit came striding across the floor to meet me.

"Are you Jay?" She asked. I nodded and stuck out my hand. Her handshake was more firm than I've gotten from most men. "I'm Barbara Sloan."

"Hey," I said. "Sorry I'm late. Turns out walking here was a stupid idea."

"You're right," she said. Barbara reminded me of every sorority sister I knew in college, only with a milfy patina. She had dark brown hair down past her shoulders, a pinpoint Oxford shirt, and the obligatory pearl necklace. I suspected she was hiding a respectable rack under the starched cotton. I stole a glance at her left hand. This was before I learned how to be subtle when doing a ring check. She glared at me. She was a thirty-something, single, aging cheerleader, and pissed off about it. "Fuck you, asshole," she said with her eyes.

"Come with me," she said. As she led me down the hall, I wondered what her ass looked like under all that flannel. I also noticed that most of the cubicles on the seventh floor were empty, or filled with packing boxes.

She led me to a desk in one of the empty cubes. There was a stack of paperwork waiting for me. "Fill out these forms. Take your time. I'm not going to be able to deal with you till after lunch."

I scrounged a pen from one of the empty cubes and commenced slogging through the forms. A couple of times, to relieve the tedium, I went over to the mens' room to masturbate.

It was going to be a lonely summer. My girlfriend Christy was interning on a marine biology vessel in the southern Pacific. No phones, no email.

Back in my apartment, I made a mental note to budget my orgasms. I'd pretty much hit my limit at the office. But, as boring as my office was, it was nothing compared to that fucking apartment. So, I found myself sitting in that tiny hot room, listening to the freeway and the TV in the next apartment, watching porn with my dick limp and used up.

TUESDAY

I was wandering the seventh floor on my afternoon break, looking for a new place to jerk off, when I came to the corner office. The door was open. I could see dark wood paneling and hear jazz coming from inside. I peeked in.

There, behind a massive wooden desk, sat a woman. She looked up. She was backlit by a huge window, so I couldn't get a good look at her, but I could feel her examining me. "Who are you?" she asked.

"Um, I'm a summer intern. One of the expendables in Sector 7G." I heard her snort at the Simpson's reference. That was a good sign.

"Come over here and tell me how it's going."

She motioned me over to a leather club chair next to the window. I walked across the room. Her office was enormous. As soon as I crossed the threshold, I felt like I'd been transported out of the grimy glass box and into a private club. Through the two walls of windows, I could see a panorama that included a golf course, the posh suburbs adjoining it, and the city's skyline in the distance. From the seventh floor, the neighborhood seemed less like something from a William Gibson novel. Between the thick Persian carpet and the wood paneling, we were completely isolated from the office outside.

I took my seat. It was the first touch of luxury I'd felt since I'd arrived. I was now on the other side of her desk, so I could get a better look at her. The chair was a few inches shorter than hers, so I found myself looking up at her.

"Marie Fletcher," she said. She didn't rise or offer her hand.

"Jay," I said. "I'm working for Barbara Sloan."

"How do you like that?" She asked. Marie was remarkable. Her face was tanned, with high cheekbones and a strong jaw, surrounded by a mane of blonde hair. She was wearing a mint-green linen suit, with a short skit that showed off her legs. Her white heels complemented the suit and echoed the white silk blouse that she wore under the suit jacket. It was cut low, so that I could see her magnificent tits. I don't think I'd ever reacted that way to a woman in her fifties. She brought to mind Martha Stewart's younger, hotter sister. I didn't need to search for her wedding ring, because it was enormous.

I suddenly realized that I hadn't answered her question.

"That bad, huh?" She said, chuckling. "Barbara can be kind of a bitch."

She spent the next two hours asking me where I grew up, what my parents did, what college was like, how I spent my spare time, what my girlfriend was like, why wasn't she here, and a ton of other personal questions. She was perceptive and empathetic. She revealed nothing about herself, but soon knew everything about me. After about two hours, she rose, clearly intending to walk me to the door. This gave me the first full view of her classic hourglass figure. I didn't know anything about clothes in those days, but it was obvious even to me that she'd had that suit carefully tailored to show off her curves.

She offered me her hand. When I took it, she pulled me up from the chair, bringing us face-to-face for the first time. In those heels, her eyes were level with mine. I gulped. I think she could tell I was disarmed.

"I'm glad you're here," she said, returning to a businesslike tone. "Is the internship meeting your expectations?"

"Well, it's a little slow right now."

"Let me see what I can do," she said. Putting her hand on the small of my back, she guided me across the carpet to the open door.

"Oh, and before I forget..." She leaned forward conspiratorially, "When you masturbate tonight, I want you to think about me."

I was speechless. Before I could respond, I'd crossed the threshold and Marie had shut the door behind me.

***

I shuffled down the hall, dazed and hard. By the time I reached my desk, Barbara was sitting in my guest chair.

"I got a call from Marie," she said. "I'm to give you a more challenging assignment." She was obviously pissed that I'd managed to go over her head. She was sitting there, about three feet from my crotch, where my cock was still throbbing from my encounter with Marie.

As she stood up, Barbara handed me a booklet, "The Elements of Freight Forwarding".

"You can study this for the remainder of the day." I wondered if she could hear my eyes glazing over while she talked. "When you get in tomorrow, I'll have a project worthy of your talents waiting for you." I nodded and kept my mouth shut. Then she lowered her voice. "I'd be very careful if I were you."

Then she left.

***

Back in the apartment, I listened to the traffic while Googling Marie Fletcher on my plastic iBook. It turns out that when you run an air freight company, you can keep a pretty low profile. But I was able to piece together a story.

Marie had founded the company when she was thirty. She had built it into a regional economic power purely on the force of her personality. I wasn't surprised she was a sales powerhouse. I'm sure every shipping manager in the region had tried to get in her pants. But it was also clear that she knew how to build a business. Ten years ago, at the age of forty, she'd married a lawyer, the prominent heir of a powerful local family. Then, about eighteen months ago, the shipping business went into the shitter.

That's when she brought in Barbara as chief operating officer.

The unimaginative trolls at Fletcher Freight called her "Barb the Barbarian". She had been cutting expenses for the last year. Last month, she had laid off two-thirds of the company. The following week, she went on vacation, leaving the survivors to pick up the pieces. It turned out that, against all odds, Barb was a bigger cunt than I thought.

I thought about Marie's breath on my ear. An electric chill ran through my body. Remembering her words, I became instantly hard.

I was able to find a few pictures of Marie at various fundraisers. I don't think anyone ever took a bad photo of her. There she was, a blonde Amazon dressed in a series of remarkable gowns, each fitting her so tightly that it looked like she had been sewn into them. In every shot, you could see not only how amazing her breasts were, but that they complemented the curve of her hips, thighs, and ass. There was no question those tits were real. She was as perfectly proportioned as Mae West or a real-life Jessica Rabbit.

In that moment, I decided I was done with college girls. I wrote a terse break-up email to Christy. She wasn't likely to see it for weeks, but I needed her out of the picture.

I put down the computer and unzipped my jeans. I closed my eyes as I thought about what Marie had looked like right before she leaned over and whispered in my ear. I imagined her reaching into my pants at that moment. Biting my ear. I pulled out my cock and started by teasing it lightly as I imagined she would do. I reached up under her tight jacket to grasp her breasts. I could feel her hand tighten on my cock, stroking me faster. Before I was able to undress her in my fantasy, I came like a fire hose.

WEDNESDAY

I had no trouble getting to work on time the next day. I was hoping Marie would be waiting for me at my desk. By the time I got there, Barb had already dropped a pile of papers on it. But on top of the stack of crap was a square envelope. Stuck to the outside of the envelope was a yellow sticky note that said simply, "Come by my office at 4:30". I opened the envelope. Inside was - literally - an engraved invitation.

"Join us on Friday, June 3, 2005 at 8:30 pm to celebrate the return of Barbara Sloan from her much-needed vacation and the rebirth of Fletcher Freight." Below that was written in beautiful script, "Jay: I hope you'll be able to join us, Marie." As if I'd miss a party at her house. Then I moaned at the prospect of not seeing Marie before the end of the day. My thoughts ran wild at the prospect.

"Come with me." It was Barb. She'd come up behind me while I'd been imagining Marie's bedroom. She knew how to ruin a reverie.

Barb marched off down the hall, to the closest corner of the seventh floor - the corner furthest from Marie's office.

"Here's your project. We had to lay off 73 people last month. There wasn't time to properly process any company property in their possession." Damn straight, I thought. You'd already bought your plane ticket.

"The only thing we care about are the computers. I've ordered a shredder and a dumpster for rest of it. I want you to check each cubicle, and confirm that the computer in that cube is the same as the one described on this inventory," she handed me a stack of paper.

"While you're checking the hardware, I also want you to delete any personal files that you find. That'll do until the IT department has time to properly reformat the drives and auction off the computers." I had a feeling that there was more to this than met the eye.

"Am I looking for anything in particular?"

"Our IT guy is a Jehovah's Witness. I can't count on him to look the other way if we find anything, um, ..."

"Compromising? Incriminating? "

"Your words, not mine. I've marked a few systems on the inventory I think you should start with."

Barb turned and left without saying another word. She wasn't going to explicitly ask me to erase any illegal porn on the computers, but the assignment was clear enough.

I spent morning trolling the directories of ancient Dell desktops looking for porn. Barb was pretty much right about which employees were the most obsessive wankers. Most of the office pervs had had the good sense to encrypt their stashes. But, naturally, I found a bunch of naughty GIF's, a few with Barb's face amateurishly Photoshopped onto them, but nothing straight-up illegal.

So I spent the day looking at porn, thinking about Marie, and trying not to jerk off. I'd decided that I wanted to keep my edge for when I saw her. The day crawled by.

At 4:28, I made my way over to Marie's office. She was waiting for me, leaning against the edge of her desk.

"Come in," she said. "Close the door behind you, and stand right there. " She pointed to a spot in the middle of the room. I could hear jazz coming from speakers on the wall. "Do you like Miles Davis?" She asked. I figured she was talking about the music, so I nodded. Marie said nothing, but it was clear she know I was bullshitting.

"Are you coming to my party on Friday?"

"Yes," I answered. I tried not to sound too eager, but I doubt I pulled it off.

"Do you have a suit?"

"No. Does it matter?"

"Oh, yes. I want you looking your best. I figured you didn't have a nice suit, so I'm going to get you one."

"That's not necessary."

"I insist." She unfurled a tape measure. "Turn around and raise your arms. Marie proceeded to wrap the tape measure around my chest. She measured my neck and then the length of my arms. "Undo your belt. I want to get your waist." She pushed my jeans down a few inches, wrapped the tape around my waist, getting me in the right position by putting her hand on my ass and pushing. She left it there longer than she needed to get a measurement.

"Now, the inseam," she said. Then, she walked around in front of me and got down on her knees. She pulled my pants down around my ankles and ran the tape from the floor, up my leg, to my crotch. She appeared to make a mental note of the number. She then slid her hand up to my cock, which was just as hard you'd expect.

She smiled up at me as she stroked my erection through my underwear. "Did you think about me last night?" She asked. I moaned.

"Yes," I said. "I came really hard." I was about to come again in my underwear. I was aching for her to take me in her mouth.

"Me, too," she said. She stopped stroking me. She stood up, pulled my pants up around my waist, and buckled my belt for me. Then she closed her eyes as she kissed me hard on the lips. "It was exquisite." She paused for a moment, and then opened her eyes.

"My tailor will be here Friday at 1:30 with your suit." The whole time, I'd thought the suit was just a cheesy hustle to get my pants off. She'd apparently actually memorized my measurements while she was feeling me up.

As I regained my composure, I leaned forward to kiss her again. She pulled away. "Slow down," she said. "I shouldn't have done that." What the hell?

She walked over to her desk and picked up a handful of papers. "Please do me a favor and drop these off on Barbara's desk. I know she's anxious to get them."

I walked back to Barb's desk in a daze. My face was warm with excitement and embarrassment. My cock was rock hard. My legs were rubbery. I found Barb working on a spreadsheet. I dropped the papers on her desk. "Marie sends her regards," I said.

"Are you OK?" She asked. This was the first time that Barb had given me any indication she gave a damn about me.

"I'm not sure yet," I said. "Is it OK if I leave for the day?"

She waved me off like she couldn't give less of a shit.

***

That night, I was ravenous. I realized I hadn't eaten all day. I'd worked through lunch, driven by nervous energy. I also had no desire to return to my apartment.

I treated myself to the bottomless chowder bowl at the local Lobster Garden. It reminded me of library paste with rubber pencil erasers suspended in it. But I gobbled bowls full of the stuff until the refills stopped coming and I realized they were closing for the night.

I walked the mile home to the apartment, as confused and agitated as I had been when I left the office.

Marie clearly wanted to fuck me. But her teasing was starting to piss me off. She should have just pulled down my underwear and sucked my cock when she had the chance. I was beginning to realize that she held all the cards, and also that I couldn't expect her to behave like a college girl. She'd been fucking guys like me since before I was born.

When I got to my apartment, there was a small, gift-wrapped package sitting by my door. Surprised that the meth heads next door hadn't snagged it, I unwrapped the package. Inside were two CD's: Kind of Blue and Live at the Blackhawk. Miles Fucking Davis. Marie had been to my apartment while I was eating dinner. If I had been home, would she have knocked?

THURSDAY

I was awakened 7:30 by my phone. I rolled oven and flipped it open.

"Good morning, Jay!" Fuck. It was Marie. I cleared my throat and gathered my wits.

"Uh, hello?"

"Meet me in front of your building at at 8:30. I have a big day planned for us." My mind raced. What could she possibly have in mind? At this point, it could literally be anything.

I was standing in front of my building at 8:30 when a Mercedes sedan pulled up to the curb with Marie at the wheel. I climbed in. Like her office, the interior of the sedan was quiet, luxurious, and filled with music. Some sort of classical thing with too many violins.

"Good morning," she said. "I'm calling on customers today, and I thought you might like to tag along and learn something about the business."

"Sounds good," I said. To be honest, I was hoping she was going to take me to a hotel and fuck my brains out. But customer calls beat the hell out of cataloging the computers of the dead. I picked up the CD case on the center console and read it. Beethoven's late string quartets.

"I know that's a little intense for this early, but I'm in a reflective mood." Here it comes, I thought. She's going to apologize for not sucking my cock. "I wanted to apologize for yesterday afternoon. I was really only intending to take your measurements and I got carried away. That was thoughtless and disrespectful, and I'm sorry." Shit.

"Feel free to disrespect me."

"Heh. I was completely out of line. I was attracted to you the moment I saw you in my doorway, and I needed to know more about you. I loved the way you handled yourself while I was asking you all those personal questions. You're smart, funny, and hot. But I still haven't decided whether you're as remarkable as you seem, or if you're just a charming psychopath."