Penthouse Letters: Hollywood Edition

Dear Penthouse: This never happens to me. After our broadcast this morning, I called the new production assistant into my office. About 5’8”, legs that won’t quit, and an ass so tight, it’s practically begging to get pinched. “You wanted to see me?” she asked. We’ve been playing this cat and mouse game since she started here. I offered her a seat and pressed a button under my desk. My office door slammed shut. She started, her pupils dilated with wonder and raw, primal feeling. I could see her muscles tense up. Happens to women all the time when they’re ready for me. That’s when I slid the box across the desk. Her hands shaking with desire, she slowly removed the lid and peered inside. “Oh.” she said. The color drained from her face as all the blood rushed down to her hot spot. She was rendered speechless by desire—you get used to having that effect on women when you’re a public figure. “It’s a dildo,” she said finally. “And small enough to slip in your carry-on…among other places.” I winked. “I figured you were slim.” When she came to, I pressed the green button under my desk. Thank God for Betty in HR. What a treasure.

Dear Penthouse: This never happens to me when I’m feeling good about myself. I was on the road, hanging out with a young comic after a show. She said she really admired my work. You always wonder, my work? If you follow my work, consider yourself warned. I leaned toward her, sucking in my gut. I saw her eyes twinkle with admiration. She looked like an angel. The kind of woman you hope will watch as you milk yourself dry. She asked how it was being out on the road for so many months. I shrugged. “It’s what you do, when you’re dedicated to this craft,” I said. “Do you mind if I jack off in front of you?” She tittered with nervous delight, eyeing the door. Two people coming together like that always makes you feel like a teenager again. I pulled out my engorged member, struggling with the button fly, hating how it looked, just there, plain as day, in my hands. I began to yank. She shook her head in wonder. My palms were slick with sweat, thank God. “So…were we going to talk about the Comedy Central pilot after this?” she asked. “Yeah, yeah,” I wheezed, turning to spill my essence on the nearest laminate surface.

Dear Penthouse: This never happens to me—well, not never. I mean, I’m a pretty old fashioned guy, I guess you could say. Gin and tonics. Suits and ties wherever you go. Sinatra records. When I was just starting out, if a man wanted to overpower a woman with his immense body weight, shove his erect penis into one of her orifices, and then hire another country’s secret service to intimidate her into silence, that was just a man on his way up the ladder letting off some steam with an admirer. I guess I’ve kept my head down in my work for so long, I haven’t really noticed the mores have changed. Anyway, I had seen this girl’s reel. Beautiful girl. Real talent. You have an obligation to nurture talent, if you’ve reached a certain point in your career. I went into the bathroom and retrieved the monogrammed robe and handcuffs that I asked the hotel to leave for me. Humming ‘The Way You Look Tonight’ to get her in the mood, I strode back into the sitting room, where she was leafing through New York Magazine. I let the robe drop past my shoulders. She looked up and gasped. That gasp said it all. “I want to drink you,” I said. She began to say something about having to go back downstairs to the reception. I smiled and shook my head. Uma Thurman once told me I have an unforgettable smile, and I guess it’s true. “One phone call, and you’ll be slinging ten-dollar handjobs underneath the 405 by the veterans’ cemetery for the rest of your life,” I purred. She put up a little fight, the way they do so that you don’t think they do this for just anyone. Boys will be boys.