Office Tramp - Sex Stories

Office Tramp

I was nervous to meet him at work but I was shocked when I stepped into his building. Of course we had discussed his job, but he hadn’t impressed upon me the successes of his company. As the shiny elevator doors opened to the marbled floor of his company, I stopped by the secretary’s desk to check in. “I’m, um, here to see Jacob.” The secretary glanced at me over the rim of her glasses while her fingers tapped over her keyboard. A moment later she said, “I don’t see he has any appointments or interviews. His schedule says that he has blocked off the next two hours for his lunch. I’m sorry. You will have to come back later.” I cleared my throat, hesitating. Finally, I said, “Um, I am his lunch date. I’m supposed to meet him in his office. It’s just that I’ve never been here before so I don’t know where that is.” The secretary looked at me skeptically. Jacob was sexy and fit. He was the epitome of “tall, dark, and handsome.” Me? I was considered overweight. I didn’t have the stick figure of some A-cup model. I had the hourglass figure of a woman that enjoyed chocolate shakes and cheeseburgers. Sometimes, I woke up in the morning and thought of myself as fat. Sometimes, Jacob rolled his face in my titties and squeezed my playful ass-cheeks, making me feel beautiful. The secretary delicately tapped a couple numbers on her phone. She had a muted conversation with her hand over the mouthpiece. After only a few seconds, she hung up, stood, and smiled at me. “Follow me, please.” ...

... Her heels tapped on the floor and her skinny ass swayed in her pencil skirt as she led me to a large, closed-in office with a heavy wood door. An even heavier looking wooden desk stood proud in front of large windows that overlooked the city. He was leaning against the desk with a snifter in his hand, smiling at me. He didn’t even look at the secretary as he told her, “Thank you, Angela. Please leave us.” He set down his glass and took my hands in his. “You know that thing we’ve been talking about?” I scrunched my nose, unsure of what he was referencing. “You mean painting the bedroom? Are you finally agreeing with me?” He smiled at me and said, “Nice try. No. You haven’t won on that yet. The other thing…” “Jacob, I don’t know what… Oh! Oh. That thing.” His smile grew even wider. “Yes. That thing.” I smiled back at him and wrapped my arms around his neck, sidling my body up next to his. “What made you decide that?” “I checked your browser history. I was trying to find something I had looked up previously but then I found …” I had to prompt him to continue, “What did you find?” “Porn. I stumbled onto what you watch on your computer. I didn’t realize that you were that into it and that you were already checking it out. Does it excite you that much?” My face froze. He went through my computer history and found my porn? Fuck. I didn’t watch easy little videos of romantic porn. I liked to watch a woman getting fucked. Hardcore. I wanted to watch her get her holes filled and smacked ...