Late Night Policy
The first few months after opening my own insurance company were relentless. Each morning, I arrived while the city still lay under a blanket of pre-dawn calm, my mind overloaded with tasks that needed my immediate attention. The office was small, a couple of rooms filled with the echoes of my solitary footsteps and the persistent hum of the aged air conditioner.
When the stack of unfiled policy applications nearly toppled over one morning, I knew I needed help. That’s when Lisa entered the picture. She responded to my job posting for an assistant, and her resume boasted the kind of organizational skills I desperately needed. But it was her composed presence and ready smile during her interview that convinced me she was the right choice.
Lisa adapted quickly, bringing order to the chaos of my startup venture. She had a natural ability to soothe frayed nerves—mine, mostly—with her easy laughter and thoughtful insights into the business. She wasn’t just helping manage the workflow; she was turning the office into a place where I actually wanted to spend my time.
The night that truly changed our dynamic unfolded unexpectedly. A major client demanded a last-minute revision to their policy, which meant an all-nighter was on the cards. We ordered takeout and hunkered down, surrounded by piles of paperwork and the soft glow of computer screens.
As we worked, the conversation drifted from the professional to the personal. I discovered Lisa was a weekend volunteer at a local animal shelter, a fan of vintage jazz, and had a hidden talent for modeling; Being a very beautiful young blonde girl it wasn’t hard to picture her modeling.
Sharing stories from my college days and entrepreneurial misadventures, I felt a connection forming that went beyond the usual employer-employee relationship.
By the time we put the final touches on the documents, it was past midnight. We were both exhausted, yet there was a palpable sense of accomplishment in the air. I looked over at Lisa, catching her in a moment of quiet satisfaction, and something clicked in my mind.
“Lisa,” I said, “I couldn’t have done this without you. You’re more than just an assistant to me; you’re like my work wife.”
She chuckled at the term, but her eyes sparkled with delight. “I’ll take that title, Josh. Just make sure you don’t make me deal with all the paperwork alone.” I replied with “never but I wouldn’t mind seeing some of your modeling work sometime” and here eyes lit up with excitement “I only have a couple of pictures with me on my phone” she said, opening her phone Lisa started to look through her photos and she showed me a few pictures of her on a motorcycle and she only had a bikini thong on.
She looked at me and asked “what do you think “ I replied “it’s amazing you are so talented and beautiful” I learned back in my chair and looked down at her butt and smiled, I could tell she loved showing off her beautiful body when she smiled back.
“I would love to see more of your beautiful work someday” I said to her, then Lisa smiled and said “ I got a great portfolio that I think you will love” I replied “really tell me about it” she said “it was a photo shoot to try out for playboy, I didn’t get published but it was a great shot”
I told her “look at me I’ve got a playboy model as a work wife” she smiled and sitting down in my lap and putting her arms around me we started to kiss, it didn’t take long for her to get down on her knees undoing my pants pulling my dick out, she started sucking me off, Lisa was really putting on a show looking at me while trying to swallow my member.
Lisa got up and took her slacks down bending over the desk, she had a very thick and golden tan ass, I placed my dick on her ass and she pulled her cheeks apart revealing her pink anus and pussy, I proceeded to insert myself into her pussy, Lisa was extremely wet like nothing I had ever experienced before and I could tell she was very much into what we were doing.
With every thrust deeper into her, my balls were slapping against her wet pussy making a magnificent sound from the contact over and over again, she said “I’m going to cum don’t stop do me harder” I gave her all I had grasping her hips firmly I had lifted her feet off the ground and was holding her up fucking her from behind as hard as I could feeling her wetness rundown out of her pussy onto my balls and down our legs till she screamed out “f u c k m e” as she orgasm.
I continued doing her for quite some time and was loving every second of it but I wasn’t ready to finish quite yet when she looked back at me and said “you can cum in me or on my ass or maybe you would like to cum in my ass?”
Not one to pass up a opportunity I Immediately pulled out and placed my dick on her ass hole, I started working on it when she wet her fingers and reached back and put it on her anus so I could get it in, I placed it back on the hole the head slipped right in; I stopped for a moment my dick pulsing, as proceeded back to pumping it into her ass; It didn’t long for me to be balls deep again but this time I was in her perfectly pink balloon knot and loving every second of it!
She was so warm and soft feeling with every stride I could feel her anus clenching to my shaft sliding from the head to the bottom of my shaft, my dick burned with pleasure the pleasure of forbidden fruit, I could feel my balls tightening up getting prepared to release, I was putting it off as long as I could enjoy every second of it till I couldn’t take it no more and I just released shooting my load inside her, my cum was so deep that when I slid my cock out, I spilt not a single drop.
Lisa slid her slacks back up, looking at me and smiling. It took me a second to put my dick away. and for a moment, I was hit with that post nut clarity this is amazing, but what have I done?
I knew one thing for sure.. things were about to get complicated, could we kept things, professional, and occasionally have fun in the evening? What would be the repercussions if she was to leave or get upset? I couldn’t think of any of these things very long when she asked if we had things to do late tomorrow.
As we parted ways in the empty parking lot, the term ‘work wife’ lingered in my mind. It was quirky but fitting. Lisa had become indispensable, not just to the functioning of the office but to the spirit of it as well. Driving home, I realized that amidst the endless paperwork and client calls, Lisa and I had started building something significant. Not just a business, but a partnership that I hoped would last as long as the company would.
6 comments
HOT 🔥
I’m glad you liked it. What was your favorite part about a story?
@Josh87707
When she bent over the desk. 😈
@YourDickToUse196 she knows what’s up 🔥