After the interview, I had no idea what to expect from my new job. Would every day be filled with sexual innuendo, fingering, and blowjobs? Not so much. It turns out that even an administrative/sexual assistant still has new-hire paperwork. There were orientation sessions to attend, forms to fill out, and computer accounts to configure.
My desk was just outside Cheryl’s office. It still felt weird to be on a first-name basis with one of the most powerful executives in the world. Of course, she did tell me to cum on her chest within an hour of meeting me, so perhaps a degree of informality was appropriate.
Liz, it turns out, had her own desk right down the hall. Her office was practically identical to Cheryl’s but without a waiting room or assistant. She didn’t need either one since she spent nearly all her time working from Cheryl’s couch. “Learning at the foot of the master,” she called it.
Their working relationship was intense. They were both driven and shared a sense of impatience with a world that sometimes still struggled to accept powerful women. They often spent the entire day together. Working lunches spent brainstorming. Strategizing during exercise breaks in the executive gym. Ordering dinner so they could work late.
I would see them when they walked past my desk, or when they called me in to give me tasks. Liz liked to flirt, but Cheryl was all business. I was so busy trying to get my feet under me that by Friday afternoon, I was starting to wonder if I had somehow imagined the whole interview.
I was trying to figure out how to configure my email filters when Liz emerged from Cheryl’s office. She winked at me and walked out with an exaggerated roll to her hips. I watched her leave and then shook my head to clear the distracting memory of her thighs wrapped around my head as I went down on her.
A moment later Cheryl appeared and told me to follow her to the boardroom. I knew from her calendar that she was presenting the quarterly report to the board of directors in half an hour. I assumed she was going to show me how she wanted the room prepared, so I grabbed the stack of printouts for the board members and followed her.
In the elevator, she made small talk, asking how I was enjoying the job so far. As I answered, she made a point of looking me up and down. I hadn’t had a chance to buy new clothes yet, and I felt underdressed in my khakis and cheap tie. Especially compared to her.
She was wearing a tailored charcoal blazer over a silk blouse and matching skirt. My eyes drifted down her nylons to a pair of shoes that I assume cost more than my last paycheck. She turned to face the door, and that angle gave me a peek down her shirt at her cleavage. Trying to be professional, I looked away. I did my best not to remember standing over her, shooting my load on her tits.
The boardroom was the best conference room in the building. A long mahogany table dominated the room. It was surrounded by fancy chairs from an Italian company. They had tall mesh backs, no armrests, and looked more expensive than comfortable. One entire wall was floor-to-ceiling windows with a view of the river. On the opposite wall was an enormous flat-screen display with a complicated video-conferencing rig. It was currently showing a screensaver of tasteful photos from the ad campaign for the company’s latest high-end vibrator.
Cheryl directed me to set a printout at each seat. As I did, she paced back and forth behind her chair at the head of the table. It took me a moment to realize that she was nervous because it seemed so out of character. It was interesting to realize that even Cheryl Sandstrom got nervous before talking to the board.
Finally, she took a deep breath and turned to face me.
“Mike, I’ve got a little ritual I do before every board meeting, and I’d like your help with it today.”
“Um, do we have time?” I glanced at my watch and raised an eyebrow questioningly. “The meeting’s in 15 minutes.”
“Don’t worry,” she chuckled, “It won’t take long. Normally I do this by myself, but I think it’ll work even better with your help. Will you lock the door?”
“Sure.” I walked to the door and locked it, wondering what sort of ritual she didn’t want anyone to walk in on her performing.
When I turned around, she had removed her blazer and was carefully folding it over the back of her chair. Then she walked around the table, motioning for me to follow her. I did, watching as she moved to the chair at the opposite end, furthest from her seat. Before she sat down, she grasped the hem of her skirt and shimmied it up around her waist. Then she hooked her thumbs under the waistband of her nude-colored thong and slid it down over her thigh-highs. I stopped in my tracks and gawked at the dark hair of her neatly trimmed bush as she stepped out of her underwear.
Sensing that I had stopped, she looked up at my startled expression and beckoned me closer. As I approached, she handed me the scrap of lacy fabric. Her expression was businesslike, but the twinkle in her eye revealed that she enjoyed the effect she was having on me.
“Hold onto these for me. I’ll want them back later.” She settled down in the chair, leaning back, spreading her thighs, and smiling confidently. My cock twitched as she reached down and parted her lips, letting me see the pink of her inner folds.
“Mike.” My eyes snapped back to her face. “Help me get ready.”
I didn’t need any further encouragement. I stuffed her thong in my pocket and dropped to my knees.
She stifled a surprised laugh as I immediately buried my face between her thighs. I knew we didn’t have much time, and I intended to make every minute count. That laughter turned to sharp gasps of pleasure as I traced her contours with my tongue. I savored her taste, dipping inside before continuing to explore.
I sucked one lip and then the other into my mouth, pulling gently and swirling my tongue over and between them. Glancing up, I saw her staring at me with hunger in her eyes. My cock was already throbbing with excitement.
Her hands tangled in my hair, pulling me firmly against her. She rolled her hips, grinding against my face and growling with need. I responded in kind, probing deeper inside. It felt like she was opening to invite me in. The taste of her cream grew stronger the further I went.
“More,” she groaned. “Use your fingers.”
I moved upward, circling her clit, and she moaned, dropping her head back against the chair. I slipped one finger into her sopping pussy, and then another. She began breathing in short, staccato bursts as I started to fuck her and lick her clit at the same time. For a long minute, her grip on my hair tightened almost painfully, and then she shoved me away.
I leaned back on my knees and wiped her juices from my chin. She lay there for a moment, gasping and squeezing her thighs together. Then she pushed to her feet and indicated I should take her place.
“Pull down your pants, Mike,” she said huskily. “Hurry.”
Eagerly, I undid my belt and let my slacks and boxers fall around my ankles as I dropped onto the chair. My erection jutted upward, a smear of sticky precum on the tip where it had been straining against my underwear.
Cheryl moved forward to straddle me. I reclined and slid lower to make the angle work better. She put one hand on my shoulder and leaned against me as she positioned my head between her lips. Then she lowered onto me, and we both gasped as my cock slipped inside. I reached up to squeeze her breast, but she swatted my hand away.
“No,” she gasped as she started fucking me. “I don’t want my top… ahhhh… to get wrinkled.”
She closed her eyes and settled into a slow and steady rhythm. Her inner walls felt velvety around me, her heat seeming to radiate through my body. She was muttering under her breath, but I couldn’t make out the words. I gripped the seat of the chair tightly, and my cock swelled inside her.
I was swimming in the sensation of fucking Cheryl — the smell of her arousal, the heat of her body, the taste of her pussy still on my tongue. I stared at the way her lips wrapped around me, slipping up and down my shaft. I felt overwhelmed and knew my orgasm was approaching.
“Oh fuck,” she blurted, as if she’d sensed my thoughts. “I’m gonna cum.”
Her left hand darted between us and started rubbing urgently against her clit. I winced as she dug her fingernails into my shoulder as the orgasm rippled out from her core. She rocked in place, her thighs squeezing me tightly. She let out a long, low, animalistic groan, and I felt her insides pulsing around my cock. A warm gush of fluid washed over my balls.
But just as I reached for her hips, ready to fuck her against me until I came, she stood up and stepped away. I was left gasping, my cock throbbing and twitching, her fluids dripping between my legs onto the carpet. She was already slipping her skirt back into place. Sensing my dismay, she leaned in and gave me a kiss on the cheek.
“Don’t worry, Mike, you did great. I don’t have time to help you finish, but after you let the board in, you can go see Liz. She’s expecting you. Now, come on, up and at ‘em.”
She turned her back on me and walked away, smoothing the wrinkles from her skirt. Aside from looking a bit flushed, it was like nothing happened. You’d never know that minutes ago she’d ridden me to orgasm, or that her thighs were slick with her own cum.