Ashleigh's Diary: Rise of the Slut

Dear diary,

It's been nine weeks since my last entry. I told Jenna about the experience with the military guys. It's the first time I've ever felt like a woman has lusted to be in my position. Maybe all those years of me talking about my relationship with Max didn't exhibit true happiness and fulfilment. It's not until you're out of something that you really acknowledge that you weren't 'living' -- you were just getting by.

I said goodbye to that girl a little while ago. I couldn't tell Jenna about the office encounter with Josh. It's crazy, but Josh actually got back together with his ex. Then they split, then she revealed she was pregnant. I... Don't even know what to say on that one. Life is happening and it's happening FAST.

I've been trying to suppress things -- my urges, desires and impulses. Maybe I'm going too crazy. Is it concerning? I just know that I can't live without really enjoying myself sexually. I've had offers to sleep with other men, per their hungry DM's, but I just wanted something that made me feel alive.

Have a got a juicy one for you... I was made to feel alive by somebody who I didn't expect. I took an internal promotion and have gotten to know James quite well. James is our Interim CEO, working occasionally at our office, in between here and our other branch 35 miles away. Is it bad that after not seeing him for some time, I scoped out his ring finger?

Sadly, James is married. Note the 'happily' part not being featured. It's amazing when you're sitting in on meetings and having 1to1s what a man will reveal to you. Especially as a younger woman. I always wondered how older men viewed me. I know, now, that I have something they want. In fact, something they need.

A guy in his late 40s hasn't fucked a pair of cheeks like mine. The old me would think that's incredibly cocky. It's just the truth. They can't get enough of girls with huge, good quality asses. The type of fillet mignon butts that their wives don't and will never have. They're ticking away on the age clock, you see, and me, well, you could argue I'm in my prime.

I was invited to go on a business trip with James. All I needed was one more little hint, and I was determined to make him mine. As if the looking at my ass, revealing a lack of sex in his marriage and issues around his wife's attitude wasn't enough. I needed final confirmation. I soon received it when James and I got to the check-in desk of the hotel.

"So, to confirm, you have a double room, on the 5th floor. Here is your card key and enj..." The hotel receptionist said, before being interrupted, "double room? It was twin I would have ordered, I'm 99% sure." James contested.

"It's fine. Those beds are huge anyway. C'mon, boss. Let's head upstairs." I said, smirking.

I made three people turn bright red in that instance. The receptionist, who struggled not to laugh, along with James and then even myself. I thought, fuck it, I won't see that receptionist again. And, besides, I now knew this was either an elaborate plan, or I'd just made the best of a situation spontaneously. I know, I'm a naughty fucking bitch.

As James and I went into the room, I embraced the luxury. We didn't have anything going on until the morning and he suggested heading out for food. I told him that I had everything I needed right here. I caught his eye, as he took his tie off. James looked at the floor, then at me, asking, "are you sure there's enough space here? We can look at a twin."

I envisioned myself looking like somebody out of a movie, as I sat on the edge of the bed, with my legs crossed, looking up at him. I pictured Margot Robbie in the Wolf of Wall Street. I looked into James' eyes and said, "this bed suits me absolutely fine, James."

James looked at me, then his wedding ring. I can't believe it, but I bravely pitched a gamechanger, as if I hadn't laid out my intentions already, saying, "take it off if it makes you feel better."

He moved closer to me and I didn't move or hesitate. Instead, I chose to offer him the final set of words that he needed to hear. I told James, "you can have me on one condition. You treat me like a disposable, naughty fucking slut. Your slut. And I will never tell a soul. Do we have a deal?"

James took a moment, comprehending if this was real. He immediately nodded and moved my hair out of the way. I arched my neck back, looking at him and non-verbally screamed, "fucking ch0k3 me, Daddy."

Taking the hint, he kissed me, gradually placing his hand closer towards my neck. I laid back on the bed with him side mounted on top of me. My hands were above my head, emitting true, submissive behaviour. I was his naughty girl, and now, my neck embraced a strong hand around it.

James lifted my top and he made love to my tits, unclipping my bra in one take. My hips raised and he removed my jeans. I was now only in my baby pink thong, which had a soaking wet patch. James loved what he saw and I felt my neck clamped, along with my erect nipples making their way into his mouth.

I moaned his name, James, and he told me he loved what I had just called him. I took a moment, smiling, then called him Daddy. My first pure DILF. FUCK! Single life was amazing. I stripped James down on the bed, and be whispered, "naughty girls get spanked."

This was music to my fucking ears, as I instinctively bent myself over his lap. I'd overlooked that his huge, man hands could weigh down some huge thuds. As this thought crossed my mind, I was spanked over and over and over. FUCK, it hurt so good. My cheeks were getting redder and redder. They felt hot, flushed and used.

I had to be a good girl for Daddy. I pleaded with him to keep going, despite the overwhelming urge for him to continue. The sound of my ass being spanked filled the room and I was thrown onto the bed. James mounted me and I perked my D-cups up, whispering, "I want Daddy's dick in my mouth."

"What do good girls say?" James asked, raising his eyebrows.

"Good girls deserve dick, Daddy. Please, baby. I want you dick. Can I have i..." I was interrupted by the exposure of James' cock. Oh my fucking god. It was quite literally 8" long. My eyes opened fully and I likened it to the size of my forearm.

I anxiously swallowed, opening my mouth and resting the weight of his dick on my tongue. I focussed on his mushroom head, inducing moaning, as he reached back and played with my clit from the top position. The perks of having a huge cock, I suppose. I was soaking wet for James. I'd been sharing an office with a man concealing THAT top-tier dick. The type of dick I'd only seen in porn and heard one of my friends talk about.

I licked, sucked and fondled my way into James' good books. Minutes later, as much as I loved sucking dick, I asked if I could bend over for Daddy. He picked me up, powerfully carrying me towards the bathroom. He put me down, turning on the rainfall shower head and told me to get into the shower.

As I stepped in, I naturally got onto my knees and he propped me up. I heard the words any woman would want to hear, "bend over for Daddy, Ashleigh." I placed my forearms on the shower wall ahead of me, with the water running down my back. My feet came wide a part and I braced myself.

I had my hands placed behind my back. My cheek was pressing against the shower wall, making me feel like his little play thing. I gasped as the biggest cock I'd ever seen and sucked made its way into my pussy. I felt 10% pain and 90% sexual euphoria as he proceeded to warm me up, then fucking me harder and harder.

I came within the first few minutes. Almost a record time for me. I'd been upgrading and upgrading when it came to my sex life. I was so fucking lucky to be hooking up with a man like James. How was his wife NOT enjoying that dick? It's uncanny that I thought of her, as his phone rang on loud in the bedroom.

"That bitch can wait. She's forgotten what the word sex even means." James mumbled.

"I'm your good fucking girl. I'm your pleaser. It's me that deserves that cock, Daddy." I sharply responded.

With that, James moaned and I sensed he was about to cum. I prepared and got onto my knees, with him practically fucking my face. Put it this way, big cocks and BIG cummers. James' cum glided down my throat and I heard moaning of, "swallow it all, bitch." I felt like a nasty fucking slut and I loved every moment of it.

James hopped out of the shower. I saw in the reflection of the mirror that he slipped something into his mouth. He saw me look, saying, "it's a blue tablet. I'll be ready again in 5."

I paused, eagerly awaiting him to re-join me. He continued, "I knew after seeing the office camera that you were a freak."

I froze. James went again, saying, "don't worry. Only I've seen that footage. I knew you'd be easy. You remind me of a slut I fucked in college from the Cheerleading squad."

Why, oh why, after all of these encounters, did I find myself looking in the mirror and feeling like an absolute whore? I told him I was a slut for him. I braced myself for round 2, taking comfort in the luxury of a hotel room, having fucked my stud DILF boss. I loved being called a good girl.