DILF of the Day - 11/9/23
It started innocently enough. Mr. Gordon asked for my personal number before he left for a few meetings in Montreal, just in case anything came up. He only texted me twice that week, once to make a few urgent updates to his keynote presentation and again to change his flight home from Friday morning to the evening.
My boyfriend, Nick, thought it was wrong that Mr. Gordon had me working outside office hours. I smiled and nodded along with his indignant rant, but I honestly didn’t mind. It made me feel important; If the boss needed something, he knew he could rely on me. I didn’t have to counterfeit the smile on my face I realized that Mr. Gordon trusted me.
Mr. Gordon took me to lunch the next week. He told me to call him Jeff. Not wanting to abuse his generosity, I tried to order a salad, but Jeff interrupted, “He’ll have a ribeye, actually.” I didn’t say anything as the waiter nodded, sneaking a curious glance at me. As the waiter left, Jeff grinned and said, “You deserve it. You’re practically my right hand man.”
Jeff got more talkative after our lunch. And Nick started getting frustrated with how much time I spent “fielding his texts” as I misleadingly called it. The truth was that barely any of Jeff’s texts were work-related by that point. He wanted to know everything about me, and I’d be lying if I didn’t admit the feeling was mutual.
I’d never clicked with someone so much older than me; Jeff was pushing 50 and I had just turned 23. I once thought of Nick as a wise, old soul even with just a few years on me, but he suddenly seemed like a child in contrast to this mature, worldly businessman. It didn’t help that Nick started throwing tantrums about my ‘obsession’. He threatened to give Mr. Gordon a good talking-to, and a quiet part of me wanted to see that.
Honestly, everything had been friendly and platonic up to that point, but I got to telling Jeff about my relationship problems. He was supportive and sweet. He told me stories from his divorce, mostly a litany of What Not To Do’s.
“But is the sex good at least?” Jeff asked in his characteristically forthright fashion.
“It used to be…” I admitted.
“Isn’t that always how it is? ;)” He started writing another message, but it sat in purgatory for a long moment. “Does he at least blow you? ;)” he finally added.
I felt my cheeks blushing and I felt glad that Nick had gone to the grocery store. Part of me knew I should stop the conversation there, but that part wasn’t connected to my fingers. “No, but I guess I prefer being the one to do that.”
“You like servicing him?”
My chest tightened with tension, but I found myself nodding. “Yeah…”
“I bet he likes that ;)”
I chewed my lip as I replied. “I guess, but he wishes I were more versatile.”
“Hahaha, weird. What man complains when a guy wants to worship his dick?”
“Haha, straight ones? :D” I joked.
There was a bit of a pause in the quick conversation, but just as I was about to change the subject, Jeff wrote, “Not all of us ;)”
I stared at those four simple words and my dick hardened in my shorts. My fingers were shaking when I went to reply. “Really?”
“Really.” A few seconds later, a photo pushed his message up off the screen. Jeff sent a selfie where he stood in front of a bathroom in nothing but a pair of briefs, heavy with a coiled cock. I could practically feel my fingers running through the thick brown hair on his firm chest. I imagined his heart thumping against my hand through his powerful pecs. Another message appeared, “You should serve a man who will appreciate it.”
“I wish I were on my knees right there,” I admitted.
“Meet me in my office in at 4:30. Tell Nick I called you in to help with a presentation for Monday.”
I almost stopped myself. I almost said no. But I couldn’t do it. “Yes, sir.”
“Good boy,” he wrote, adding, “It’s time for my right hand man to take my right hand’s place on my manhood ;)”
He fed me a massive load, oozing down my chin onto the carpet in front of his desk, and promptly fucked another into my ass for good measure. When I went home late that night, I saw a message pop up on my screen as I got out of my car in the driveway.
“Tell Nick you have a headache. I don’t want to share you with him.”
“But he’ll be pissed… and I can’t have a headache forever…”
“Just until I get you a new place closer to me, babe ;)”
I guess it was my choice when I broke up with Nick. It was my voice, but the words were Jeff’s. He was in my head and in my heart, and the force of his personality pummeled mine into submission. But he didn’t want to change me; he wanted me to be who we both knew I was. I was his whore, and it made me happier than I ever hoped.