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.
The board meeting was scheduled to start in just a minute. I could hear voices outside, waiting to be let in. Nothing for it but to move forward.
I stood and pulled my boxers and pants back up. After fastening my belt, there was no way to miss the large erection tenting the front of my slacks. I grabbed one of the extra printouts and used it to cover myself as I walked to the door.
Before I opened it, I glanced at Cheryl to confirm she was ready. She nodded as she buttoned up her blazer, so I unlocked the door and let the board in. They didn’t even notice me as they filed in, greeting one another and starting conversations.
I was desperate to go see Liz, but I forced myself to stick around long enough to see whose seat Cheryl had fucked me in.
The board was a collection of notable women in business, who had all bought early stakes in the company. But my money was on the one board member who stood out: the only man in the room other than myself. He was tall, with a dark complexion and grey at the temples. Everyone else seemed warm and friendly, but he had a scowl on his face as soon as he walked in.
Sure enough, he strode purposefully to the far end of the table. I didn’t know if there was assigned seating, or if he intentionally chose the seat most symbolically opposed to Cheryl’s. Either way, he clearly considered it his territory. I watched him drop into the chair, oblivious to the large wet spot on the carpet.
I was curious about the backstory between them, and how he and Cheryl had ended up on literally opposite sides of the table. I wondered how many times she had masturbated in his chair to give herself a psychological edge over him.
But I wasn’t curious enough to stick around. My cock twitched demandingly in my pants, and I hustled to the elevator, eager to see Liz.
That was the longest elevator ride of my life. I swear it stopped on every floor, and everyone in the office got on and off. I felt that in the close space the smell of sex coming off me must have been unmistakable. I kept my eyes glued to the floor, and the papers carefully held in front of my hard-on.
At long last, I got to my floor and practically ran down the hall, past Cheryl’s office to Liz’s. The door was closed, but remembering that Cheryl said she was expecting me, I walked in without knocking.
Liz’s office was similar to Cheryl’s, but a bit smaller. There was a bookshelf along one wall full of business-school books and vibrators. She had a modern-looking desk with a big leather executive chair. Against the window was a couch, framed by a great view of downtown. But my attention was on Liz.
She sprawled across the couch, grinning crookedly at me. Her shirt was untucked and unbuttoned, revealing a thin lace bralette that did nothing to conceal her nipples. She had hiked her skirt up around her waist. Her underwear was tangled around one ankle, caught on a high heel. One hand was squeezing her breast, while the other held a large purple vibrator. I recognized it as one of the new models the company had just released.
She squirmed languidly as it rumbled against her clit. Her bare pussy glistened, wet and inviting. My cock, which had started to soften during the eternal elevator ride, twitched at the sight. I dropped the papers I’d been covering myself with and shut the door behind me.
“Hi, Mike.” Liz bit her lip and let her eyes drift down to my erection. “I was hoping you’d come to see me.”
In answer, I unhooked my belt, kicked off my shoes and started undressing.
“Oh myyyyy,” she drawled. “Looks like you’ve got some unfinished business to complete.” She clicked a button, and the buzz of the vibrator intensified.
My clothes fell in a heap, and I stood naked before her. My semi-erect cock was already swelling back to life. The room smelled noticeably of sex, but I wasn’t sure if it was coming from me or her. Or both.
“Is there something you’d like, Mike?” She blinked innocently at me, and I mentally cursed. She was going to make me ask.
“Liz,” I croaked, my voice husky with need as I moved closer. “I, uh…”
“Go on,” she purred, “Tell me. Tell me what you want.”
“Please help me cum,” I blurted.
“Good boy!” She carelessly tossed the vibrator to the other side of the couch, leaving it rumbling away by itself as she dropped to her knees and took my cock in her hand. She grinned at me when she felt it throb with anticipation. Then she wrapped her lips around me.
My cock stiffened quickly in the heat of her mouth. She swirled her tongue around the tip and took me as deeply as she could. I gasped as she bobbed her head, trying to swallow more. After a moment she pulled back and pumped her hand along my shaft, her lips still sealed around me.
After a frustratingly short time, she swirled her tongue around my head once more and stood up to kiss me. I wrapped my arms around her, urgently pulling her body against mine. She giggled and squirmed as I squeezed her ass, my erection pressing against her hip. When the kiss ended, she licked her lips and whispered in my ear.
“You’re lucky I like the taste of Cheryl’s pussy.”
I felt a surge of lust and tried to pull her back in for another kiss, but she slipped out of my arms and danced away from me. She let her shirt drop to the floor, then unhooked her bra and tossed it aside. Still wearing her high heels, and making sure I was watching, she strutted to the couch. I watched as she deliberately bent over the armrest, putting her elbows on the cushion and leaving her ass up in the air. She waggled her rear invitingly and winked at me.
I wasted no time getting in position. Her laughter at my haste turned into a gasp as I rubbed the head of my cock between her already wet lips. Then a squeal as I thrust forward, burying myself to the hilt. The sensation of her pussy suddenly wrapped hot and tight around me was overwhelming. I knew it wouldn’t be long before I came.
I squeezed her hips and started fucking her. Each thrust slammed her thighs against the side of the couch. She cried out wordlessly, her face buried in the crook of her arm. After just a few strokes I felt my orgasm swelling.
“Fuck me, Mike!” Liz moaned happily. “When you cum… ah! I want you to… ah, fuck! Cum on my tits!” For just a moment, she lost her words, slapping the couch as her pussy clenched around me. “Oh, I want you to cum… Please cum for me, Mike…”
“Liz,” I grunted, her words driving me over the edge, “I’m gonna…”
Before I could finish, she twisted around, popping my cock out and dropping once again to her knees. She squeezed her breasts together, showing me where to cum. I stroked my cock, and she watched eagerly, squealing in delight when the first spurt shot onto her cleavage. She continued to moan happily as my cum fell in ropy strands, covering her fingers and nipples.
When the last aftershock passed, and I released my grip, she leaned forward and took my head in her mouth. I gasped at the nearly overwhelming sensation as she licked up the last bit of my cum. When she released me, I staggered a few steps, before collapsing onto the couch.
She followed, sitting at my side and leaning on me. I watched as she ran her fingers through my cum. She hummed happily as she rubbed it into her skin and then licked her fingers clean. After a while, she pulled my arm around her, snuggling against me and cupping my hand over her breast.
I was just starting to doze off when she stood up to stretch. I watched, admiring the shape of her body as she yawned loudly and let her skirt fall back into place.
“Well, we better get dressed. Cheryl will be back from the board meeting soon, and she’ll want to chat about it. You should come to take notes.”
I nodded and started pulling my clothes back on. Liz put her bra and shirt back on, and untangled her underwear from around her heel, throwing it behind her desk. She was helping me straighten my tie and adjust my belt when she noticed the lacy fabric sticking out of my pocket.
“What’s this?” she asked knowingly, pulling the thong out and making a point of holding it up appraisingly.
“Cheryl’s underwear. She asked me to hold onto them for her.”
“Really?” She raised an eyebrow at me. “These are expensive. Don’t steal them. She’ll want them back.”
“What?” I stammered, “I wouldn’t! I wasn’t going to…”
“Relax!” She giggled and gave me a quick kiss as she tucked Cheryl’s thong back in my pocket. “I’m teasing you. Although…”
She walked over to her desk and picked up the underwear she’d just thrown back there. They were black mesh with pink trim. She strutted back toward me, and before I knew how to react, she shoved her hand down the front of my pants. I gasped as I felt her rub the thin fabric against my still-sensitive cock. She leaned closer to whisper in my ear.
“You can keep these,” she breathed, “But I expect you to jerk off in them and send me a photo in exchange.”
“Uh, okay,” I gulped as she pulled her hand out, leaving her panties wrapped around my cock.
“Great, it’s a deal!” She smiled and turned away to open the door. “Now, let’s get back to it.”
I followed her across the hall to Cheryl’s office, wondering if I was capable of keeping up with these women.
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<a href="//vermect.ru/stories/office-sex/-ms-sandstroms-assistant-part-4-the.aspx"> Ms. Sandstrom’s Assistant, Part 4: The Board Meeting </a>