My Lucky Penny 1: Radical Honesty

Note : This story is completely fictional!

*HEADNOTE* This story is not simply pornographic. Worry not, I will get into detail during sexual scenes, but I will also be concentrating on storyline as well. Enjoy the story...

I don't know who intially wrote this program, but the stupid fucker ought to be fired.

Hi. My name is Caleb O'Connor, and I'm a computer software programmer for a company called InaTech. Fortunately I work out of the home, meaning I never have to actually "go" to work. It's a good thing, really, as it's doubtfull anyone there wants to work around a gothic cross dresser. Of course, the only person I've met there is the head boss when I was interviewed. I actually showed up in my black vinyl pants (with an extended zipper in place of a button), my black vinyl halter, and extremely feminine arm bands that reached from my elbows to the back of my hands. It was obvious to me that he was uncomfortable seeing that. But of course, after a demonstration of my programming skills, it was the furthest thing from his mind.

So there I sat in my living room, on my bean-bag chair, with my laptop computer on my lap. I remember being dressed in a few of my favorite things: my black pleated skirt, short-sleeve button-down blouse (which I would never tuck in), fishnet stockings, and knee-high buckle boots. Most styles of panties weren't big enough to contain me, so I only wore them when I went out, or if I wore a mini skirt. There were always spikes around me neck and wrists, that was a given. So was black nail polish and face make-up.

I was frustratingly engorged in a segment of serously corrupted code when my roomate, Josh, came down the stairs. See, the house was like a duplex, but instead of renting a second floor, the house owners rented to us their finished basement.

"Caleb, will you turn that shit off?" Josh complained, referring to the techno music I had playing. He was also gothic, but more stereotypically so, preferring heavy- and death-metal music. "What are you doing anyway, and why the hell are you dressed up?"

Good eye, I gotta credit him that. Subtle as the differences were, Josh had learned to discern between dressy and casual for me. I guess what really tipped him off though, were my high pig tails that reached my shoulders (I usually let my hair hang loose).

"As to you first question," I began, still typing, inhaling my cigarette, "a million things." Truthfully, it was only four things: my previously described work, Windows Media playing my techno music, chatting with friends online, and playing a real-time MMORPG (Massive Multi-player Online Role Playing Game).

"As to the second, my sister's coming today. Remember?"

Penny O'Connor, my sister. She was coming to live with us for the summer, a place she knew she could relax and get some writing done. She wrote horror books for a living, and ranked right up there with names like R.L. Stine, or even Stephen King. She was also attending college to become a video game programmer.

I could care less about all that though, I was just happy to have her for the summer. I've always had a crush on her growing up, and to be honest I still have one. Penny wasn't celebrity-grade sexy, but she certainly was not ugly. You could say she had a certain "x-factor" about herself.

"When's she gettin' here?" Josh asked.

I looked at my watch. "Should be soon." No sooner than I stopped speaking did our doorbell ring. "Speak of the devil," I said, setting aside my laptop and putting out my cigarette. I jumped up and ran to answer the back door.

The door flew open, and there stood my radiant sister, dressed in a chrome-colored skirt-suit, her blond hair pulled back into a low pony tail. She dropped her one duffelbag (which appeared to be her only luggage), as I scooped her up into my arms for a spinning hug

I had to set her back down quickly. Just holding her so held a level of excitement, and I could not afford a hard-on without anything under my skirt. I picked up her duffelbag and led her downstairs.

"I'll be sleeping on the hide-a-bed out here," I explained, "so you can use my room."

*****

It didn't take Penny long to settle in. She relaxed most of the evening, enjoying mine and Josh's company. By nine, Penny had retired to her laptop, which she had set up on the desk in my room. Two hours later, she was still working. I brewed some coffee and brought her a glass.

"Hey," I said quietly, slowly stepping into the room.

"Oh, thank you so much," said Penny as I handed her the hot coffee. She sipped it and smiled. "I see you still remember how I like it."

"How could I forget?"

I stepped behind her chair and began massaging her shoulders. She instantly relaxed at my touch. A soft moan escaped her lips, and her eyes closed as her head rested against my body. I figured this might happen; earlier I had changed from my fishnet stockings to my fishnet pantyhose. They wouldn't stop me from getting an erection, but at least it would be well hidden.

What an erection, too!

"So what's on your mind?" Penny asked me. How did she always know? Then again, she is my big sister.

I sat on the bed and sighed. Penny turned her chair to face me. "I guess honesty is the best place to begin. I like you, Penny. Ever since our early teen years, I've like you."

"Your point?" Penny asked, confused. Then it hit her. I could see it in her expression. "Oh. 'Like', as in 'crush'. Caleb, I admit I had a crush on you too when we were younger. But I've grown up."

"Have you?" I challenged. When she didn't answer verbally, she did so with her eyes. They gave away that the feelings still lingered. I knew what to do. I rose and headed for the door.

"Caleb, wait!" Penny called out to me. She had stood by the time I turned, and I slowly approached her once again.

"Wait for what?" I inquired, though I had not the patience for an answer. Gently I closed the gap between us so our lilps met. Pressing out mouths firmly together, my sister and I began wrapping out arms around one another. I pulled her body close, allowing my rock-hard arousal to feel her in full.

Penny pulled away.

"Our family hates you enough for cross dressing," she reminded me.

"And they hate you for approving," I added.

"We shouldn't add incest to it."

I grabbed my sister's ass and lifted her, causing her area to grind against my own. "Think about it," I requested. Finally I left the room, leaving Penny to her thoughts.