I worked at a posh office on the 58th floor of the Sears Tower. I grew up a Chicago girl and would never call it Willis Tower. If they ever try to rename Wrigley Field I think there might be an uprising.
My job didn't really meet my needs as far as challenges went. I was a glorified secretary. That English major did little good in finding a job with a living wage. I thought I'd write Catcher in the Rye from a female's point of view. Yeah, I needed to get on that.
Although the actual work was boring, filing, answering calls, typing letters, there was a very large part of my job that involved something that made me excited to come to work everyday with a skip in my step. I was fucking my married boss.
He was gorgeous. Tall, with large, strong hands, hazel eyes, and chiseled features and a huge cock. The truth is, I was in love with him, but I knew he wasn't in love with me, but instead with her. It hurt, and I hated the weekends, but I absolutely loved Monday through Friday.
Yeah, you could say I'm a whore, getting paid to fuck my boss. Well, that's not how it started and I don't believe he's a philanderer. One night, on the second Wednesday I had worked there, I was packing up my bag to leave. I usually stayed later on Wednesdays because I took a yoga class out on the lake that didn't start until 7:30, so I just hung around until then. I noticed my boss's light was still on, which was strange. He was always out by 6:00, having a wife and 4 little children to go home to. Maybe he was trying to meet some deadline, so I stopped by his office to offer assistance.
"Mr. Dean, do you need...."
I trailed off as soon as I saw his eyes were red. He'd been crying. It was really awkward, but long story short, he invited me out for a drink and spilled it all. He told me he would always love his wife. she was his high school sweetheart, and he didn't want to break up his family. But, his wife had no time to pay attention to him (understandable with 4 kids, but come on, the dude was hot). He said he dreaded going home because he felt invisible, unloved. His wife was now a roommate, a friend, not his lover. She had never been adventurous in the bedroom, always wanting the lights out and preferring only vanilla sex. He confessed that he'd only gotten a blow job from her once and he'd gone down on her twice and both times after about 2 minutes she pushed him away. He didn't want to cheat on his wife, but he was so lonely, and so fucking horny...
Three martinis later we were in a beautiful hotel room and I was doing my best to give him the most amazing blowjob of his life. Earlier, he had explained that we should only have oral sex. I guess he thought that wasn't cheating or something. His cock was fucking big (bitch didn't know what she was missing) but luckily I don't have much of a gag reflex. I was playful at first, sucking gently, changing rhythms and stopping to lick all the way from top to bottom of his cock and then sucking on his balls (that made him crazy). I decided the poor guy didn't need anymore teasing and sucked hard on that big glorious cock. I did not break eye contact with him once. He looked so grateful. The harder I sucked the faster my rhythm was. I couldn't fit it all in my mouth (deep throating lessons would come later) but didn't neglect any of his shaft or his balls with my hands. I was so focused on making him cum and was wet as hell. As I stared at him with his delicious cock in my mouth, his eyes rolled back in his head. As he started to cum, I pulled his cock out a bit and stroked him. He watched as his load filled up my mouth. I swallowed that hot cum and was dying to get off.
"Was that good?" I asked, feeling more like his assistant than his lover.
"That was amazing, so amazing. Thank you so much. That was just what I needed."
At this point I was worried that he was just going to leave me there alone and I'd have to play with myself. But I was very, very wrong. He gleefully announced it was my turn and ordered me to lie on my back. He started at my breasts, licking and sucking on them with fervor. He slowly, teasingly made his way down my body. I had pink satin panties on and he pulled those off with his teeth (OMG!). He stared at my pussy for a little while, spreading my lips apart and playing with it like it was a new toy.
"Your pussy is fucking beautiful. I love that you shave." He took in a deep breath. "Fuck me, you smell so good. I can't wait to taste you."
He dove right in. If his wife never let him go down on her, I wondered how he was so fucking good at this He focused on my clit just as I liked it, sucking and licking. He kept moaning, which vibrated through my pelvis. He stopped for a second, wet two fingers in his mouth, and explored inside my pussy with his thick fingers. He was looking so intently at my pussy, almost like he'd never really seen one before. This just made me even hotter.
He paused for a second and looked up at me. "By the way, you taste fucking amazing," he said.
"By the way, I could drink your cum by the gallons."
"Fuck, baby."
He buried his head once more and got to work. He took his two fingers and stretched my lips apart and massaged the inside of my cunt. Then, his fingers went deeper in. Holy shit, I think he was searching for my g-spot! He continued to suck on my clit. I'm not sure if he found the g-spot, but I can tell you my body reverberated for what seemed like more than 10 minutes. It was the most mind-blowing orgasm of my life.
After the hotel, we kind of ignored it for a while. He started telling me I looked nice every day, something he hadn't done before. When I brought in papers his stares lingered. He looked sad. I wondered if he needed a good fuck.
Then it started. The Monday after we tasted each other he started instant messaging me through our work computer system. Things like, "I miss your pussy on my tongue." "I can't stop thinking about you." "I dream about you giving me head every night." "You're so beautiful."
I wasn't sure how to react. I mean, I was happy because I didn't want it to end, but scared because he was my boss and was married. But, of course, I'd read these messages and my panties would get wet. I'd reply with: "You gave me the best orgasm in my life." "I loved your cum in my mouth." "I absolutely loved sucking your cock."
A while passed until I heard from him again. The wait was torture. Suddenly, my instant messenger popped up with 3 words: "I need you."
I walked into his office.
"Hello there, beautiful," he said
"Hi," I half-whispered.
He shut the door and grabbed me and kissed me with a hunger so palpable my panties instantly became soaked. He lead me over to his chair. He sat down and unzipped his pants. I got on my knees and sucked hard, never breaking eye contact. He came very quickly.
