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.”
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.
“My god, I was a fool to think I could stay away from you,” he said.
Next, he slapped the top of his desk twice and told me to take off my skirt but keep my panties on. He sat in his chair while my legs rested on his shoulders. He buried his nose into my panties.
“Fucking delicious,” he said with a smile.
At first he touched me through my panties. Then, me moved them to the side and started teasing my clit. Finally he ripped them off and ate me out. He was so amazing. I loved having him taste me. I wonder if the smell of my pussy lingered on his face when he went home.
Weeks continued much the same. He’d send me a message that said, “Come here” or more to the point “Get in here!” I sucked him off at least twice a day and he fingered me and tasted me just as often. Sometimes I would surprise him while he was on a telephone call and get on my knees, pull his cock out and suck away. It was funny how he had to continue these important business calls without talking funny (although once in a while there was an uncontrolled moan). He never stopped me and confessed that he fucking loved when I did that. I loved our oral sessions. Of course, shortly after he started fucking me. He told me he just couldn’t control himself and he was dying to be in my pussy. Most days I went home completely sore after being pounded by Mr. Dean about 5 times a day. The man had stamina.
Then one day he decided he wanted even more. I could tell he had a terrible fight with his wife the night before, because he was brooding. Not that our sex life was getting boring, but I think he wanted to try new territory. It had to be exciting for him that I was basically his little slut. I never said no and worked hard to make him cum as often as I could. I wore garters and stockings, short skirts and tight tops. Eventually he hired a “temporary assistant” to basically do my job while I worked on him. I don’t know who did his work.
An instant message popped up on my computer. “I need you right now. Door is closed but come in. Lock it behind you.”
I did what I was told, always excited to please my boss and have great sex in the process. He sat at his desk looking mellow. He tilted his head toward the table, ordering me to look. What I saw was a surprise: A bottle of K-Y and dildos of varying sizes.
“You told me you’ve never had anal. I haven’t done it in a long time and so I want to fuck you in the ass.”
“Um, ok,” I was intrigued.
“I need you to take off your skirt and panties and bend over the table.”
It wasn’t the most romantic proposal, but one I willingly obeyed. Mr. Dean pulled apart my ass cheeks and started licking my asshole. It felt different, but really good. Sometimes when we were fucking he’d put a finger in my ass which excited me; this was even better. I moaned as his tongue went inside my asshole. Then he put a finger in front of my lips and told me suck on it. I did as I was told. He pulled out the wet finger and started playing with my asshole. First, just going in circles on the outside, then plunging his finger in.
He breathed in deeply. “Fuck, baby, you drive me crazy. This little asshole needs a good fucking, and I’m going to deliver.”
He couldn’t see me but I smiled in delight. I was so wet and excited. I couldn't even imagine his huge cock fitting in my tiny asshole.
“Ok, what I’m going to do is start with the smallest dildo and work my way up. If this takes all day, that’s fine. I’ve cancelled all my appointments,” he said.
I heard something being poured and realized he was putting lube on the toy. He started with a dildo abut twice the size of his finger. He inserted it slowly and methodically then moved it around in my asshole and it was really exciting. I felt so naughty. He kept pausing to ask if I was okay.
“Good job, honey. Now I’m going to use the next dildo. It’s bigger. Just relax.”
Again, he lubed up the dildo. It took a little more time getting it fully up my ass, but he did. I felt fuller. He started rubbing my clit with one hand and with the other started fucking my ass with the dildo. I moaned in pleasure.
“Do you like that in your ass, baby?”
“Oh god, yes!”
I could feel his hard cock in his pants as he’d sometimes rub it against me. There was one more dildos left, the last one slightly smaller than my boss’s cock.
The third dildo was predictably harder to insert; he couldn’t get it in past the tip. Mr. Dean took a break and rolled me over onto my back. He ate out my pussy and ass until I came. However, he was relentless. He ordered me to bend over the table again and went right back to putting the large dildo in my asshole. This time it slid it more easily. I was clearly relaxed from my orgasm. Again, he started fucking me with the dildo. It was a unique sensation; pleasure with a bit of pain. Clearly the visual of the dildo filling up my ass was exciting him. He pulled it out slowly. I figured we’d take another break. I was wrong.
I heard him unzipping his pants. I looked behind me and saw his huge cock.
“I don’t think I’m ready yet, Mr. Dean!” I said.
He crouched over me, his lips right next to my left ear. He then whispered, “Who is your boss?”
“You are,” I said.
“Good. It seemed for a second like you forgot. You’re going to take my cock up your little asshole whether you’re ready or not, understand?”
I was shocked by his domineering manner. He’d never pulled the boss card before, but I guess he never had to. Truthfully, I loved that he took charge.
A second later he was rubbing the inside of my asshole with lube. Next, he was pouring some on his dick and rubbed it in.
“I need you to relax, ok?”
“Yes, Mr. Dean.”
He put his cock just on the outside of my hole, teasing me. then, slowly, he inserted the tip. I groaned in pain.
“Relax, relax, baby. I just need to stretch you out. I’m going to put more of my cock in you.”
He went in another couple inches. It hurt like hell. I underestimated. His cock was much bigger than that last dildo.
“Mr. Dean, stop!”
“Shhh, it’s ok. It’s halfway in now. You’re doing so well. We’re almost there.”
I couldn’t believe he wasn’t stopping and I could tell the fact that I was protesting was getting him more excited because he thrust the rest of his huge cock inside me ass.
“Ow, no no no,” I pleaded.
“Holy fuck, you took it all. Good girl! Your little asshole is absolutely strangling my cock. Jesus!”
He started thrusting very slowly, taking his cock almost all the way out and then inserted it balls deep. I bit on my lip and tried not to think about the pain.
“Oh, Christ, your fuck hole is amazing!” he blurted out.
Now, he started fucking me at a faster pace. When he did this, he reached his hand to my pussy and massaged my clit. I couldn’t believe it, but he was right. I had gotten used to his thick cock and I started enjoying getting my ass fucked. I started moaning in pleasure.
“Oh, you like it now? You like my cock in your tiny ass?”
“Yessss!” I squeaked.
“You are such a good little slut. Oh, yeah. Look at you taking my thick cock. You were meant to be mine. I own this ass now!”
“Yeah,” I replied. “Fuck my ass harder, Mr. Dean. Please, harder!”
He drew in a breath and started pounding the fuck out of my asshole. He continued diddling my clit. I loved that I was pleasing him, that he taught me how to get fucked in the ass.
Suddenly, the loudest groan escaped his lips. He stopped moving, and I could feel his hot cum squirting in my asshole. “Fuuuck yeah, baby. Oh, you’re my beautiful slut. Jesus Christ!”
After that day, we became even more obsessed with fucking each other. Our affair started spilling over into after-work hours. We’d get a hotel at least 3 nights a week to continue our frenzied fucking. He would take me out to dinner, buy me sexy lingerie and perfume and other gifts. His favorite thing to do by far was pounding my ass.
I have the best job in the world!
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