My Boss Fucks My Ass In The Coffee Shop — Don’t Tell His Wife!

When my boss walked through the door of the coffee shop I work in with a face like thunder, I knew the last customer of the day was going to be the most memorable.

My co-workers had already left for the night. It was getting on for eight o’clock and I was half-way through cleaning up. He usually only opened the store — he was never there for closing.

“Amy,” he said plainly, nodding his head as he approached the counter. We hadn’t spoken much since the argument.

“Mr. Whittaker,” I said. “Like a drink?”

“I’ll take a mocha skinny latte.”

I sighed inwardly, trying not to let it show. I even hated his coffee orders.

“Problem?” he said.

I forced a smile. “Not at all.”

“Do you need to take a name?”

I twisted my mouth, desperate not to give his terrible joke validation.

“If you just take a seat, Sir.”

He moved away from the counter, placing his wallet back in his long-coat and taking it off. “Sir,” he said curiously. Beneath he wore his dark-blue shirt and gray suit-pants. He was still wearing his tie from the morning, even though he’d left work hours ago. I hated how serious he took himself some times.

He sat across from the counter and I could feel his eyes on me the whole time I fixed his drink. The milk frothed up and I tossed it in glass, adding a shot of coffee and chocolate.

“It’s ready,” I said, setting it down on the counter.

“Is that how you tell all your customers?”

“Not all of my customers are assholes.”

He stared across at me, pursing his lips. I don’t know if he’d come in here for an argument, but he was getting one nonetheless. I always found it unforgiveable what he did to Sheryl, his wife.

I put both hands on the counter as he approached, waiting for a response. He calmly picked up his glass and turned back to his seat, sitting down.

“I’m not the bad guy in all of this.” He said it as though he was announcing it to the room.

“And how do you figure that?”

“There are things you don’t know, Amy.”

“Enlighten me. All I know is you were quite happy fucking Sheryl’s best-friend before she found out.”

He shook his head in silence.

“So what is it?” I demanded.

I watched as he put the glass to his lips and took a sip. His face looked calm, making me even angrier.

I threw my cloth down and stomped around the other side of the counter, moving to the door and twisting the lock closed. It was almost eight.

I walked to his table and pulled out a seat, sitting down and staring at him opposite.

“So tell me,” I said.

He was still quiet.

“Tell me!”

I was desperate for him to say something that would make it all make sense. I didn’t want to hate him, but he’d left me little choice. Before the whole thing unraveled I was become quite sweet on him.

“Sheryl isn’t exactly a saint,” he said.

“Go on?”

“Look, I didn’t do this because I was in a happy marriage, okay? When you’re older, maybe you’ll understand.”

“I’m nineteen! And from the way I understand it, you fucked her best friend for no reason.”

“No reason?!”

“So what happened?” I growled desperately.

He pursed his lips again, keeping his silence. I don’t know why he seemed so intent on protecting her if she’d truly been so awful.

“I think you’re lying,” I said. “You’re lying because you know how much of an asshole you are.”

His lip curled in anger. I could see it behind his blue eyes, welling up inside him.

“You’re a lying, cheating asshole, Mr. Whittaker. Nothing more.”

I pushed my chair out and grabbed the cloth from the counter, scrubbing way harder than I needed to and hoping he would do the decent thing and leave. He couldn’t fire me for being honest … could he?

“You want to know?” he asked, his voice trembling in anger. “You want to know why?”

I concentrated on the cleaning-rag as I rubbed furiously at the marble counter. He approached behind me, putting his body close to mine.

“Because I caught your precious Sheryl getting fucked in the ass by one of your colleagues,” he said.

He pinned me to the counter with his body, but I couldn’t pay that any mind. All I could think of was the sinful thought of my older friend getting pounded in the ass. Anal sex was something that had always fascinated me. I wondered how people could possibly like it.

“Sheryl would never!” I cried, defiant.

“Oh yeah? Why don’t you ask her all about it?”

“Who was it?” I asked.

He pushed his hips forward against me. “Carl.”

“Damn,” I hushed, filling in the blank features of the guy behind Sheryl with Carl’s handsome face. It made sense: I hadn’t seen him at work in months but the rumor was that he quit.

“See now how she’s not so innocent?”

“Oh my,” I gasped, realizing suddenly what the huge bulge was that was pressing against my tight butt.

“So while I was at home your adoring, perfect mother was getting her asshole fucked by one of my employees.”

I swallowed hard, feeling him become stiff behind me as he spoke of her sinful encounter.

“Mr. Whittaker,” I hushed, my body tense in suspense.

“You want to know exactly what she was doing?” he said, his hand moving down my back.

“Yes,” I hushed, staring forward.

“You want to know what it feels like to have it stuffed in your ass — like my slut wife?”

“Yes!”

He reached beneath the tassel of my apron, pushing his hand down into my yoga-pants and sliding them down over my toned, round ass.

“Oh, Mr. Whittaker!” I whimpered, feeling the moment get away from me. I bit at my lip and glanced back, unable to look him in the eyes just yet.

I heard him unfastening the buckle of his belt behind me, his racing breath against the nape of my neck.

“Put it in my ass,” I groaned. It was as though the revelation had awakened something inside me.

“You’re just as bad as her,” he growled. “Give me your spit.”

I looked down to see his hand upturned beneath my mouth. Without thinking I spat down on his fingers.

He moved his arm away and then I felt the wetness of my spit as he pressed it against my virgin asshole.

I gasped as his fingers touched me, rubbing around my tight knot and intriguing me more than ever. It felt good to have my ass teased like that, but I had no idea what I was going to be in for.

Soon I could feel the head of his cock pressing against the muscle and my mouth opened in a silent moan.

I stared forward, wide-eyed as the crown started to widen the muscle slowly. My eyes closed tight in a wince and a groan started it in pit of my stomach, eking from my neck as I felt my ass stretch wider than ever.

“Oh, fuck!” I grunted, slamming my hand my hand to the marble countertop.

His length surged into me, feeling like nothing I’d ever experienced in my life. His cock delighted my pussy from a fresh angle, hitting the pit of my stomach and taking the edge off the pain.

“See what your precious friend has been doing?” he asked, putting his mouth close to my ear. “See how much of a dirty slut she is?”

“I do, Mr. Whittaker!” I groaned, my voice rippling with cries of pain.

His cock plowed into me, stretching my tight asshole wide and threatening to split me completely. I should have first turned around to see what I was letting myself in for, because his cock certainly felt like the biggest thing that had ever been inside me.

The longer he kept himself inside me the more the muscle seemed to relax around him. He barely moved for the first minute or so, as though he knew my pain.

“How does that feel?” he hushed.

My brow furrowed. “Good,” I said, surprising myself. “You’re big though, Mr. Whittaker.”

I started to giggle and then he withdrew, snatching the laughter out of me quickly and replacing it instead with a wince and suck of air.

“We’re only just beginning,” he said ominously.

I could feel the throbbing pulse of his cock as it eased slowly through me, my asshole gripping him tight as though it never wanted him to leave.

He built his pace steadily, my head lolling on my neck as I became drunk with lust. I could feel my pussy filling with juices, but they were no use. I needed the wetness in my ass, but the body just isn’t built that way. I wish I’d landed a whole lot more spit on his fingers.

“Good girl,” he said now, pressing me against the counter as his hand came up the front of my body to grip my neck tight.

He clenched and squeezed and I felt the blood rush to my face and turn red as the sensation of his cock inside me became stronger. When he relaxed his grip the rush of oxygen made my head feel light, but the delightful pain in my ass remained.

“Keep your ass open,” he said now. “Hold it open for me.”

My hands spread my cheeks as he pulled all the way out, leaving me with a gaping butt as he rounded the counter.

“What have we got here?” he said, looking all over. I watched his cock bounce on his waist and I steadily teased a finger toward my ass, wondering what he was searching for. I was in disbelief when I circled the digit around the stretched hole to find it wide open. I’d never been able to do that before.

“Ah-ha,” he said, holding a carton of milk aloft.

“What will you do with that?”

“Just stay there,” he said, and he returned to me holding the carton.

He cleared the table he’d been sat at then he grabbed my arm and moved me over to it.

“Keep that asshole open for me,” he said, looking to the door and windows. Thankfully we dropped the blinds around an hour before closing the shop.

He pushed me forwards over the table and I felt the cool wood against my bare cheek, my hands still at each side of my ass and holding it wide.

“Good girl,” he said, and then I felt the surging length of his thick cock all over again. “Keep your hands there.”

He pressed deep and then pulled out of me again. Suddenly I felt a rushing, cool wetness and I gasped, my asshole gasping too as I realized that he was pouring the cool, white milk into it.

“That’s going in my ass!” I cooed.

“Damn-right it is,” he said. It was his intention all along.

I felt my inside fill up with the liquid, with some of it streaming down my leg and getting soaked up by my yoga-pants.

He dragged the pants down further and I stepped quickly out of my sneakers to let him get them off my ankles.

When I was rid of them I split my legs wide, looking back at him and watching as he poured the milk from a height, right onto my gaping asshole.

Some of it fell inside whilst the rest splashed across my flesh. My virgin asshole had never been treated to such debauchery, and it was all Sheryl’s fault.

“That’s good,” he said, and then he grabbed his cock again and pushed it inside.

The milk rushed back over his advancing cock, squeezing through the tiny apertures and firing back against his blue shirt.

He started to unbutton it, pulling it off his shoulders and tossing in on top of my discarded yoga-pants and panties.

“Look at that,” he said behind me, and I wished I could see.

“What does it look like?”

“Beautiful,” he said. I never thought someone would use that word to describe milk pouring out of an asshole.

“I wish I could see.”

“Can you feel it?” he asked, pushing deeper so that more of the pure white liquid poured out of me.

“Of course I can,” I giggled.

“What’s it like?”

“Wet,” I said. “Big.”

“Feel good?” he asked, pulling out and seeming to relish the view.

“It feels incredible.”

I felt each ridge and vein surge through me, teasing my tight ring as he pumped himself into my body. It was safe to say that this wouldn’t be the last time I’d be getting fucked in the ass. I hoped it wasn’t the last time that it was him doing the fucking too.

Mr. Whittaker set the carton down on the table and then rained a slap down on my ass, filling the room briefly with the sound of a loud clap of flesh, followed by a shriek of pain.

“Mr. Whittaker!” I gasped.

He rubbed his hand on my reddening cheek. “Sorry, baby.”

I felt a sudden, tingling rush of excitement afterwards. “Do it again,” I said slowly.

“That’s my girl,” he said, pulling back his cock.

My ass gripped him as he withdrew, then it tightened as I felt the sting of his slap across my flesh again.

I exhaled with a deep, satisfied grunt, as though the pain was something I didn’t realize I needed.

“Damn!” I swooned, finally letting go of my ass and holding both sides of the table with my hand.

I started to push back against his cock, jerking him through me and using my whole body to bounce back against his huge, mature length.

“Let me see it,” I begged now, looking back to him with a pleading gaze.

He pulled out slowly and I turned around, staring at the white-washed cock. There was a translucent film covering his length and I saw for the first time just how big he was.

“That was in my ass?!” I gasped, staring at the impossibly big dick hanging on his waist.

“Sure was,” he said with pride,” holding the hilt in his hand and shaking it.

“Damn … can I suck it?”

He raised his eyebrows in surprise. “I’d love you too.”

I dropped to my knees and felt a blast of milk leave my ass and hit the floor. It pooled all white and I started to blush, but there was no room for embarrassment here. He had just poured a pint of milk into my ass — what did he expect?

“Wrap your lips around it,” he said, ignoring the milk leaking out of my butt.

I took his pants down carefully, taking off his shoes and removing his socks too. I wanted him naked in front of me so I could bear witness to his masculinity. I may never get the chance again.

I threw my blonde hair behind my shoulders and opened my lips over him, tasting the creamy milk that covered his stiffness. Feeling his arousal in my mouth was almost as good as feeling it in my ass.

I stared up and for the first time we locked eyes. I felt a pang in my stomach as I stared into the face of my boss, as though I should be guilty that he’d caught me. He smirked back and nodded, holding my cheek.

“Perfect,” he said. “You’re perfect.”

He reached down and grabbed my shirt, pulling it out from my apron and up over my head. I dropped his cock from my mouth and unfastened my bra, as though it was now a mere inconvenience.

“Fuck,” he hushed, and I looked up to see him staring right at my tits. “I had no idea they were so big.”

I took him fully out of my mouth and leant back, resting my tits between my arms and bunching them together on my chest.

“You like these?” I said, batting my lashes at him.

“Are you kidding?”

He stooped his cock to my chest and it took me only a few brief moments to realize his intention. I squeezed my tits around his dick and he took up the carton of milk again.

He poured it into my cleavage and then started to slide his cock through me, sprouting it out of the top of my tits as he began to fuck my chest.

“Yes, Mr. Whittaker!” I gasped, getting a front-row seat to proceeding now.

I stared down and marveled as his dick continued to emerge, drenched in the white of the milk that would break every so often and reveal the pink, delicious head below.

He fucked my tits for a moment or two and then I had him back in my mouth, tasting the creamy sweetness of the milk, coupled with the delightful stiffness of his forbidden cock.

I moved a hand down under the front of my apron, finding my wet pussy and teasing my fingers on my clit as I sucked him. He started to pump into my mouth, holding my head as I groaned with pleasure.

“My little slut,” he cooed.

I blinked up at him, moaning as my mouth hung wide. He fucked my face like I was his property, and I didn’t mind one bit. I wanted him to use me any way he needed to in order to get off. It felt like my only goal now was to have him come, however he wanted it.

“You are just perfect,” he said.

I didn’t ever think I’d feel good about getting fucked in the ass, but he had such a way with words that I felt as though he was doing me a favor.

“You want this cock back inside your ass, don’t you?” he said.

I looked up at him and nodded, letting his cock drop out of my mouth, followed by a dribble of milk.

“I do,” I said, putting on my most sultry of voice. “I want to feel your hot cum pour out inside me.”

I gripped and squeezed at his balls and he groaned as though I’d really done it now. He stood me up and I jumped back onto the table, splitting my legs wide and staring up at him now as he approached again.

He held his cock and went straight under my pussy, pointing instead at the sinful, puckered knot below that would ordinarily be out-of-bounds.

“That’s where you want it, huh?”

I looked up into him and nodded, locking my eyes on his as he started to push into me again. My brow furrowed but I remained focused, staring into him and watching the expression on his face turn to joy as he felt my tightness around him again.

“Oh, Amy!”

“That’s it,” I purred, aching a groan as I felt another sharp twist of pain.

I looked down to watch as his coarse hair press against my pussy and he docked home, all-the-way deep.

“Get it, Mr. Whittaker,” I insisted. “I want to watch you come.”

He pushed my thighs back and pulled me closer to him, slipping through my asshole and upping his pace quickly now.

My hand moved down and I started to spin my fingers on my swelling clit, dining out on the eroticism that I didn’t know anal sex could give me.

“Yes!” I gasped, staring into his lust-filled face as he looked down and watched me sheath his cock over and over.

The amazing sensation felt even better accompanied by my busy fingers and soon I could feel my own orgasm arriving on the periphery.

“Don’t stop,” I moaned, letting my eyes roll back as I closed them.

I concentrated on his movements and each one suddenly felt huge as he burst through me. I could hear the panting of his breath as he became excited and it was a privilege to know that I could elicit this reaction from a guy over twice my age.

“Come with me,” he hushed, and the request sounded so loving. I hadn’t expected to find romance with a cock deep in the wrong hole.

“Don’t stop,” I said again, holding my breath to focus.

I gasped and took several deep breaths, opening my eyes to stare up at him.

“I’m fucking close,” I urged. The haste in my voice was palpable.

“Me too, baby,” he strained, and he looked down to the source of his pleasure.

“Fill me with it,” I goaded. “Shoot it in my fucking ass.”

Hearing the words said aloud seemed to ignite something in me and when he spoke again it was all I needed.

“I’m gonna shoot this hot spunk in your ass.”

I never thought I’d hear him utter those words as long as I lived. The sound of him saying it hit me like an eighteen-wheeler. I gasped and felt the explosion of lust inside me, coupled quickly with the throbbing of his cock against my tight ring.

“Oh, Mr. Whittaker!”

“Oh, Amy!”

His chest filled with air as he took a breath. When he exhaled I felt the first blast of heat, firing deep inside me and warming my insides in an instant.

“Yes!” I cried, and my pussy spasmed with delight.

The contractions in my pussy rippled through to my ass just as he started to let off inside it. It was as though it was massaging the cum from his balls, squeezing tight against his shaft and then relaxing to accept the resulting blast of heat.

Every time my ass squeezed him it was rewarded with a fresh dose of cum. It felt much different to the milk from before. Not only was it thicker but it seemed to ease the passing of his cock that now glided through my once-tight muscle.

“Every drop,” I moaned, furrowing my brow with a look of pained pleasure.

He nodded. “Every drop.”

His cock swelled with each throb, throwing out hot rope after hot rope until he finally tailed off in a long groan.

The tremors of my own climax rumbled through me and I rubbed over my pussy with scissored fingers, squeezing up to the clit as he pulled back and watched his spent cock emerge.

I let out one final wince as the wide bulbous head of his cock popped free, then I watched as he jerked over himself slowly, pinching the last drop of cum off his cock and letting it fall on my pussy.

“Good boy,” I smirked, biting my finger.

“So now you see,” he said breathlessly, “how much of a slut she is.”

“It must be contagious.”

“It seems it is,” he said, holding my knee open and taking a look at my creamy slit. He hummed in satisfaction and I found myself blushing and closing my legs.

“No good being coy now,” he said.

With an asshole full of his hot cum I couldn’t help but agree.

“I still need to close down,” I said, looking back to the counter.

“I can leave you to it,” he said. “I just wanted to come and explain myself.”

“You did much more than that,” I said, blowing a shot of air up my face.

“I wanted to explain properly.”

I smirked at him, feeling the warmth of his deposit deep inside me. It was a brand-new sensation, but one that I knew I needed again. It was going to feel incredible having his warmth slide out of me for the remainder of my shift.

“So I’ll leave you to it,” he said, leaning over to kiss me.

I swooned, lingering my lips on his until he pulled back.

“Will you be back?”

“I might be,” he said mysteriously.

“I’m on late tomorrow too,” I hinted.

He smirked but didn’t answer. “I’ll see you soon,” he said, hopping back into his pants and getting dressed.

“I hope so.”

I watched him leave and turned the lock behind him, leaning naked against the blinds. I took a deep breath and slowly brought my finger beneath to touch around my ravaged hole. I could feel the viscous seed against my fingertip.

“Naughty Sheryl.” I’d be talking to her soon. I wondered if that would wind up just as sinful.