It Was Hot Drilling My Boss’s Ass for the First Time

The tight ring of her sphincter gripped my cock at its root. She had all of me buried in her bottom when I heard the angry buzz of the vibrator, as she rubbed it on her clitoris.

“Ethan, come to my office,” my boss ordered. “Now, please.”

The line went dead. There was no option but to comply.

“Come inside, Ethan,” she said, closing her notebook and placing her hands on her expensive desk.

I took several steps towards her, while the woman eyed me distinctly predatory. Everyone around the office feared Carla Johnson, the CEO of the pharmaceutical company I worked for. She was a rather attractive blonde woman, considering she was in her late fifties and she ruled the company with an iron fist.

“I like you, Ethan,” the woman said while running her fingers through her hair. “I think you’re sexy… Young, fit, and sexy.”

She turned from me, walked across the room to lock the door, and then turned a small dial on the wall. The lights immediately dimmed. “And I like my boys young and fit and sexy.”

She paused and gave me a smoldering look.

“I think you fantasize about me. Would you say that was true, Ethan?”

“Mrs. Johnson, I-I don’t think…” I managed to stammer, a little overawed by the woman.

“Do you think about me when you masturbate, Ethan?”

Without waiting for my response, the woman went on.

“I have some very special needs…” she paused, staring at me again.

My stomach flipped at the intensity of that look; I sensed something huge was coming my way.

“I keep lovers, most of them about your age, fit, strong men who can keep it up for hours.”

I felt the heat from her eyes and my cock ached, pre-cum dribbling insidiously, as Mrs. Johnson revealed her sex life to me in a low, husky voice.

“Would you like to be one of my boys, Ethan?” she asked eventually.

I decided, or rather my penis decided that, yes please, we would. We wondered, my erection and I, just what being one of her “boys”’ entailed.

“I think,” the woman continued, taking my silence for approbation, “that I’d quite like you to be my special boy. The one who gets the thing none of the others do.”

How many boys were there? Was this woman a nymphomaniac?

“Do you know what my special boy does?”

“No, Mrs. Johnson,’ I responded, my erection pulsing and my hands trembling.

“Mrs. Johnson,” she laughed. “I like the way you say that, so formal. I wonder, Ethan, will you call me Mrs. Johnson as you’re stabbing my ass with your cock?”

Stunned I blinked, my mouth hanging open like the village idiot. I’d be drooling from the mouth next instead of just my penis. It took me a moment to comprehend her meaning. Had I really heard that correctly? Mrs. Johnson wanted me to fuck her in her ass?

“Take your clothes off,” she instructed and I immediately started to undress.

In just a matter of seconds, I stood before her naked and watched as she admired my body.

“Somebody likes me,” she said and nodded at my erection. “That’ll fill my ass nicely.”

The blonde woman grinned and continued. “That’s exactly what I want, Ethan; I want you to stuff my asshole with that cock. Stuff me so full of meat and then fill my rectum with your cum.”

She was incredible; the things she said to me were pure filth. I was shocked and surprised, inflamed with desire, and I’d do anything she wanted.

Carla Johnson rose from her seat and came to me. Wrapping her hand around my cock she kissed me deeply.

“Mrs. Johnson,” I moaned as she broke the kiss after stroking my cock a few times.

She smiled and started unbuttoning her white blouse. When she turned and offered me her back, I realized what she wanted and unclasped her bra. Next, she teased me by unbuttoning her pants and unzipping them, before looking back over one shoulder, blonde hair falling down her smooth, flawless back. Easing the top of the pants down, she exposed half of her asscheeks.

“Do you like my ass?” she asked.

I gulped and nodded.

“Most men do…” she said and slid her jeans lower.

I touched my cock.

“No, no,” she scolded. “No touching until…” she paused, smiling evilly, “Until I say you can, you naughty boy.”

I dropped my cock as though it burned my fingers.

“Would you like to kiss it?” she invited, wriggling her ass like a bitch in heat. “My husband loved to kiss it.”

She rolled her eyes as she lowered her pants to the tops of her thighs.

“And he loved to tongue my dirty hole,” she finally added in a whisper.

Moments later, with her pants bunched at the back of her knees, Mrs. Johnson, still wearing the black stilettos, knelt on the leather couch, her arms along its back, and presented her back to me.

“Lick me, Ethan,” she hissed at me, eyes flashing diamonds. “Right there.”

A long red fingernail pointed to the puckered stain of her sphincter as her fingers splayed her cheeks wide.

I fell on her instantly, dropping to my knees to worship at the altar of my boss’s anus. I licked her tight ring liberally, tasting her hole as my wet tongue squirmed into the forbidden opening.

“Oh, fuck,” she groaned. “So enthusiastic. I’ve never had anyone get straight to it like that. You’re so deep in there … that’s beautiful.”

Not only did I lick her sphincter, but I slurped and slobbered over her cunt as well. She gasped when I fingered her front and back simultaneously, groaning and calling me lewd names.

“My boys can use my cunt,” she sighed. ‘But my special boy can only have my ass.”

Mrs. Johnson pushed me away from her body and I fell to the floor, panting for breath. I was crazed with lust for the woman.

Finally, after kicking her pants and underwear away, she stood facing me. I had a few seconds to appreciate the full roundness of her swaying breasts before she padded away from me on bare feet.

I watched those buttocks as she moved away from me. I definitely had the impression there was more to Mrs. Johnson than she was showing. I could easily imagine her at the center of a gangbang. I wondered, very briefly while she grabbed a small tube of lube from her desk, if she had her boys in a group, one of them pounding her back door while she took the others in her mouth and pussy.

“Lie down on the floor,” she curtly instructed then knelt next to me when I complied.

The naked blonde took hold of my cock, sliding a fist along the length. She leaned down and kissed me again while I reached for her breasts. She broke the kiss and offered a long, thick nipple to me. I sucked at it, transferring my oral attention to its twin as I cupped those heavy tits in my palms.

Finally, a low growl came from her throat, and swung a leg over my head. Her juicy cunt was just inches from my face. I knew exactly what she wanted so I took hold of the woman’s hips and pulled her down to my mouth. I heard her gasp when my tongue probed at the sluicing opening at the front of her body; another groan escaped her mouth when I pushed a finger against her sphincter. I groaned when I felt her swallow my erection.

Her moist vulva, smoothly waxed, mashed against my lips. The blonde’s hips jerked as she fucked down onto my face, her clit sliding over my nose. She began to moan in earnest, lust obviously boiling inside her as desire slid from her cunt.

In reciprocation, I bucked my hips, forcing my cock into the back of her throat. It was too much and she gagged and coughed, spitting my drool-soaked penis out of her mouth, her eyes watering.

“You naughty boy,” she gasped. “I’ll let you use my mouth later. Now I want you in my special place,” she said and spun away from me.

Whatever the lady desired.

“It’s the control,” she explained nonchalantly as she squirted a dollop of lube into her hand. “It might seem like I’m being submissive, letting you do me in the ass,” she leaned forward, breasts hanging, and smeared the lube over my cock-head. “But I’m in control. It’s only you, my special boy, who I allow in there. And if I don’t allow it, it doesn’t happen.”

She then sat on the couch appraising me with a serious stare.

“I’m going to let you fuck my ass, but I’m in control, Special Boy.”

I nodded.

“On your back. Lift your cock upright,” she commanded and straddled me, her exquisite body hovering over me.

“Easy,” she said when my cock head nudged her body. “Nice and slow.”

I felt the natural resistance when my cock pressed against her sphincter.

“Slowly,” she urged, grimacing with an effort of balancing atop my hard cock. “My dirty hole doesn’t want to let your big fucker in,” Mrs. Johnson grunted, eyes closed.

Then I felt something give and she squealed. I felt her anus opening before me as I slid in deep.

“Oh, fuck, that feels so good,” the blonde woman gasped, eyes wide.

She looked down at me, her mouth hanging slack.

“Fuck my nasty ass.”

I held her hips tightly as she began to ride up and down on my cock. Her breasts swung and shivered as she screwed her anus around my penis. The woman angled her body in such a way that I remained wedged inside her as she leaned over to kiss me. Panting into my open mouth while our tongues danced wetly, Mrs. Johnson jerked her hips, somehow maintaining the incredible pressure at the point at which our bodies joined.

“God, Mrs. Johnson,” I burbled, “If you keep this up, I’ll…”

“You’ll what? Cum in my ass?” she asked, eyes wide with expectation.

She was upright again now, hands spread across my chest as she jerked her hips quickly back and forth.

“Not yet,” she gasped as she swung her leg over me to dismount. “I want to come too.”

She got up and went to her desk again. When she returned she held a small bullet vibrator in her hands.

“Now,” she said gleefully, kneeling on the couch, and presenting her ass to me. “Put it back in my ass and fuck the shit out of me.” She laughed at the pun.

I did as I was told, gripping her hips after I slid back in. The tight ring of her sphincter gripped my cock at its root. She had all of me buried in her bottom when I heard the angry buzz of the vibrator, as she rubbed it on her clitoris. Then I felt something pushing against my cock from within and realized she had three fingers wedged in her pussy.

We fell into a rhythm of slick fucking until everything clouded for me. Every empirical sense was overloaded. The sounds, the buzzing vibrator, the obscene squelching from the fingers in her cunt, the slick fapping of my own erection sliding in and out of her ass, Carla’s moans and filthy vocabulary were just part of it, there were also the sensations in my cock as her body fought to repel me.

“Mrs. Johnson…” I warned.

“Fucking do it. I’m going to cum too. Fill me up, big boy!”

I recall leaning over her and biting into her shoulder as cum spurted from me, bathing her insides. I think I took a handful of hair and roughly yanked her head back, twisting her neck as I wedged my cock deeper into her rectum and discharged a big load. I held her head at such an awkward angle, craning over her as far as I could as we both let the pleasure cascade over us, my mouth against hers, our tongues quick and ardent.

Finally, as sensibility returned, we lay, still joined at her back door, panting and not quite believing how intense the experience had been for both of us.

A chuckle escaped her mouth when, eventually, my diminishing cock slid from her used asshole. As soon as I slid from her, a big glob of cum dribbled from the opening I’d vacated.

“My special boy,” she snickered. “You can use my cunt if you like,” she added. “But in my ass is the best.”

I was inclined to agree.

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