From Boss to Boyfriend, Chapter Four

“On the third date?!?” Eric exclaimed via text message. “That’s weird as hell.”

I lounged in briefs beside the fire pit on my balcony with a glass of chardonnay and stared at my best friend’s reply regarding yesterday’s momentous evening. I didn’t disagree, but still something gnawed at me. I replied, “I dunno. It was a little much, but kinda sweet.”

“Omg,” he shot back. “When have you ever liked a guy who was sweet?”

He knew all my secrets, much to my occasional chagrin, and he wasn’t wrong—I had a bit of a bastard fetish. Self-obsessed hedge fund managers, stuck up professors, sullen NYPD officers, and the like were the typical subjects of my frequent though short-lived infatuations. On the surface, Mike fit the bill, and I never would have pegged him for the sort to make a romantic proclamation. But more surprising, I might have liked it, if only just a little bit.

“What did you say?” Eric interrupted my ruminations. “The face you must have made…”

“I just kinda stammered until he kissed me,” I answered. “He stayed over, but we never talked about it.”

“Did you fuck again in the morning?”

“Yeah”

“Well, at least you finally banged him. I don’t think you’re ready for that clinginess though.”

In truth, I was the one feeling clingy. Mike had hardly spoken to me outside of our work and a few scattered responses to my texts. I drafted a confession in the message window, but deleted it and wrote instead, “Haha. You’re probably right.” This was one secret I preferred to keep to myself.

I gulped the last mouthful of wine and stood up a little unsteadily. Between the drinks and a glance at the sofa my boss had pounded my ass upon the night before, my briefs were bulging and my ass aching.

Striding toward the bathroom, I pulled up Mike’s Facebook profile on my phone. He had just a few scattered posts dating back weeks, mostly tagged by friends, but I opened his profile picture and swiped a few times until I found one I liked. His bright, perfect teeth in a goofy smile with those burly arms crossed over his chest, the fabric of a blue polo stretched tight over him mass, and a decent view overlooking Midtown.

I pulled open a drawer and inspected a row of dildos, arranging by ascending size, and let my hand hover over them until I selected the one best approximating Mike’s generous endowment. It felt satisfying to squeeze it in my fingers, to shut my eyes and imagine the moan he’d make.

Dimming the bathroom to a warm haze, I pulled off my briefs, knelt on the floor, and let the shining brightness of Mike’s face fill my vision as I squirted a dollop of lube into my palm and reached back to rub it between my taut cheeks. I shuddered at the cool slickness but chewed my lips as my fingers warmed it and coaxed it inside my tight ring. My slender fingers hardly fazed me as I slipped them, one after the other, inside and worked myself open in preparation.

“Oh, open me up, daddy,” I whimpered in one-sided conversation with the absent object of my desire. “It feels so fucking good, sir.” It felt silly, but when I gazed at Mike’s face I could nearly hear a reply in that low, rumbling voice.

I remembered his eagerness, his aggressiveness, and forced my fingers deeper to make myself gasp at the sudden pang. Still, my digits couldn’t match his—those thick, rough hands with their coarse tips and that iron grip. I needed more.

Circling my fingers inside me, I took another palmful of lube and greased up that fat dildo as I whispered, “Fuck, you’re so big. You want to fuck your boy’s pussy with that huge cock?” 

Fucking right I do, you little slut, he would have said. He would have kissed me, engulfing my lips in his with such a hunger it felt like he’d eagerly swallow me whole.

I couldn’t wait.

I brought the swollen head of his slicked cock to my hole and slipped out my fingers to make room for the marvel of a man. Pushing myself back, I howled as his girth forced its way between my cheeks, but once his head popped inside I couldn’t stop myself. That engorged mushroom burrowed up into me until his bulbous balls were snug against my ass. 

Tears streamed down my face as I whined to his still, smiling visage, “Oh fuck, Mike. I can’t believe you just shoved right in there.” 

This ass is mine, isn’t it? He would have asked, smacking my muscled cheek for good measure. I should get to play as rough as I like with my new favorite toy.

I crossed my arms over my chest, hands grasping my shoulders and elbows tucked against my stomach, as I imagined those powerful forearms squeezing me into submission. I rose up along the length of Mike’s member, my insides squeezing every veiny inch, and let myself drop. 

That’s it, Avery. Fuck that tight little ass on daddy’s big dick.

With every plunged, I loosened just a little. I changed the shape of myself to accommodate him and it drove him wild. “I’m yours, Mike,” I whispered, gazing at him in awe of the way his presence could make me feel even when it was just imagined.

You want me to breed this hole again, boy? He would have barked. Empty these big nuts right inside you?

“Oh fuck yes, daddy,” I shouted, engulfing every inch of him and squeezing him tight until I trembled with pleasure and my own dick spewed its excitement onto the marble floor. 

He would have filled me with his seed. He would have seen the ecstasy all over my face and had no doubt of how I felt about him. He would have claimed my body and never let me forget to whom it belonged. He would have said, I fucking love you.

As I collapsed sideways to the cool floor, Mike unfailingly engorged inside me, I whispered, “I fucking love you too.”