Ms. Sandstrom's Assistant Pt. 05

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Kara helps Mike explore his submissive side.
4.8k words
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Part 5 of the 5 part series

Updated 03/18/2024
Created 11/09/2017
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"Liz, stop," I hissed, as she tried to lead me into the shareholder event on the first floor of our office building. "I can't go in there like this!"

"C'mon, Mike, no one's gonna know." She couldn't quite keep a straight face as she said it, though.

I turned away as a small group of people in fancy clothes walked past us to the coat check. When they were gone, I gestured pointedly to my crotch. She stifled a laugh. My thin dress pants did little to conceal my erection. It twitched eagerly, as if aware of Liz's attention.

"It's, uh," she hesitated. "It's not that noticeable."

"Come off it, if I walk in there like this I could get arrested."

"Oh please, no one's gonna call the cops." She nodded politely at another couple walking up to the coat check as I turned away again. "You might end up having to talk to HR but trust me, those girls know how to party," she laughed knowingly.

"I... That's not the point, Liz! We need to talk to the research team about the pill!"

"They went home already. Besides, they said not to worry unless it lasts over eight hours."

"It's been seven!"

"Which is less than eight."

"Can't we go back upstairs to your office and take care of this?"

"We 'took care of it' three times already!" She sighed. "...Look, I bought this dress special for tonight." She gestured at the slinky red backless gown. She looked phenomenal and knew it. "Cheryl's expecting me to make the rounds and talk to board members. I'm not gonna mess up my hair or makeup just to make you cum again."

"Fine, then I'll go take care of it."

"No, no, take a breath. The research team was clear. We could do it a couple times, but then we were supposed to find out how long it lasted. You're freaking out about nothing. This can't be the first time you've had a boner in public. Just, you know, cover it up."

"I'm telling you, I can't go in there, Liz!"

"Ugh, fine." She looked around and spotted the door to the coat check room. "Okay, come in here."

She opened the door and pulled me in. The room was divided in two by a partial wall. On one side were several rolling wardrobe carts, shelves of cubbies, and a folding chair. On the other side was the coat check counter. A young blonde woman in a black dress shot us a curious look.

"Hi Kara, thanks again for working the coat check tonight. This is Mike, he's having a bit of a panic attack, so he's gonna chill here while I go in, okay?" Kara nodded and turned her attention to a couple who had just walked up to hand her their jackets.

"Mike, that's Kara. She's the new front-desk girl. You just sit here and be calm. I bet once you get your mind off it, things will settle down and you can come to join me at the party. If not, I'll be back to get you in a little while. Then I promise I'll take you upstairs and it'll be worth the wait, okay?"

I nodded, and she gave me a quick kiss on the cheek and bustled out the door, greeting several people by name on her way into the event.

Over the next fifteen minutes, Kara hustled back and forth, hanging up coats and jackets, and handing claim tickets to partygoers. Eventually, the flow of guests slowed and stopped. Kara pulled her stool over to sit next to me and regarded me curiously.

"Panic attack, eh?"

"It's not a panic attack," I responded a bit too forcefully.

"Alright," she said, shrugging. "So, why are you hiding from your girlfriend?"

"She's not my girlfriend, she's my boss, and I'm not hiding, I just can't go in there."

"Why not?"

Exasperated, I pulled my hands away, so she could see the large tent in my pants, which had not settled down even a little.

"Oh!" She grinned. "I see the problem. Does, uh, does this happen often?"

"No, I... look, you know what the company makes, right?"

"Yeah, I'm aware," she rolled her eyes. "It's only the most famous sex toy company in the world."

"Right. But they've also got an R&D department, including a pharmaceutical team."

"Huh. I never heard of that."

"Most people haven't. They license stuff out or produce it through holding companies."

"Okay, so I guess you took some kind of new boner pill?"

"Not exactly. My boss, Liz, convinced me to take a pill designed to reduce the male refractory period."

"So you can do it again after finishing?"

I nodded. "Liz told me this pill was practically ready for the market, and it would let me go several times in a row."

She laughed. "You make it sound like a work assignment."

"It kinda is?" I shrugged. "It's a long story. I'm the assistant for the two women who run the company. This kinda stuff comes with the position."

"So... you're hooking up with Liz?"

I nodded.

"And Ms. Sandstrom?"

I nodded again.

"Cheryl Sandstrom, the CEO of the company, and Elizabeth Holman, her second in command, are both fucking their shared assistant?"

"Yup."

"That's hot," she said.

"Look, I dunno if I'm supposed to be telling anyone that. I'm kinda distracted right now. The point is, Liz had me try this pill, and it works. We did it three times in a row. Then Liz wanted to see how long it would last, I've been hard ever since, and I'm kinda going crazy."

"Why don't you just jerk off?"

"Liz told me not to. She said it's important."

"Ohhh," she nodded knowingly. "I get it."

"What?" I said. "What's to get?"

"She's your mistress. You have to do what she says. This is a control game."

"What?" I scoffed. "No, it's not like that."

"It sounds like it's like that."

"It's not, trust me." I crossed my arms. "I'm not doing a good job explaining. I'm still figuring out how this situation works, but it's not, like, a domination thing."

"Sure." She winked. Before I could protest, she held up her hands as if to wave my objection away. "Look, no judgment. I've been exploring submissive relationships myself. It can be exhilarating to give someone control. To place your trust in someone like that."

I frowned. My cock was throbbing desperately, and I was painfully aware of how close she was sitting.

"The first time for me was really eye-opening." She bit her lip. "I was on this robotics trip during my senior year of high school. My roommate snuck a guy in, and she caught me watching them fuck. I thought she'd be furious."

She crossed her legs, squirming. "But she came over and told me she knew I was watching and it turned her on. Then she started touching me and telling me what to do."

Fuck me. I pressed my hand firmly against my cock, not rubbing it, but trying to get some relief. She saw, and scooted her stool closer, leaning in conspiratorially. Her breath was hot in my ear. Her breast was pressed against my arm.

"She sat on my face and made me lick her while she fingered me. Then she had her boyfriend fuck my mouth while she got me off, and I ended up covered in his cum."

Groaning, I started rubbing my cock through my pants, but she slapped my wrist and stood up.

"Ah-ah-ah, Mike, your mistress wouldn't like that. She told you not to."

"She's not my..."

"Not your mistress, I know," she said, scoffing. "In college, I tried to explore this side of myself, but all the guys I met either didn't really get it, or they were a little too into it. This one girl, though..."

She glanced behind her to make sure there was no one waiting at the counter. Then she spread her legs and lifted her skirt, revealing a simple nude thong. Slowly, she reached down and started stroking with one finger, teasing me with the shape of her lips as she pressed against the thin fabric.

"This girl, Mike, she got it. She knew what I needed. She took charge. She told me what to do. She explored my boundaries with me. She'd meet me between classes and take my underwear, or she'd make me unbutton my top until I felt exposed. She'd make out with me until I was flushed and dripping, and then make me go back to class and wait all day before she would let me cum."

Kara watched me hungrily as she rubbed herself, enjoying the effect she was having on me.

"One time she sent me to class with a remote-control vibrator and teased me until I thought I was going to leave a puddle in my seat. I ended up running to the bathroom and rubbing one out in a stall. That night, she spanked me for the first time."

Kara bit her lip and squeezed her legs together around her hand. After a moment, she slowly pulled her underwear down. I strained for a glimpse, but her dress fell back into place. As she straightened up, she held the soaked fabric to my face. The heady smell of her arousal filled my senses. I let out a choked groan and gripped the chair tightly. I wanted so badly to pull out my cock and start stroking, but I knew she would stop if I did.

"I learned if I did what she asked, she would reward me. I would come back to her place flooded with desire. She would sit on the couch and drink whiskey and have me lick her pussy until she gushed in my mouth."

As she talked, Kara unbuckled my belt and unbuttoned my pants. I was panting and eager as she pushed her wet panties into my boxers. I whimpered and lifted my hips to press into her hand, but she pulled away, leaving the fabric wrapped around my twitching shaft.

"Then she would make me cum. I was always so turned on by that point, that it never took long. She'd bend me over the back of the couch and finger me until I was screaming. Then she would call me a good girl and clean me up and hold me until I fell asleep."

She moved forward, slowly lifting her dress. Her lips glistened wetly, bright pink against her pale skin, crowned by a wispy tuft of hair. She straddled my legs, standing over my cock, which was twitching urgently and barely contained by my boxers.

"I also learned if I disobeyed, I would be punished. She introduced me to nipple clamps, spanking, strap-ons, and more. Fuck, this is turning me on telling you all this."

She gasped as she pushed a finger between her lips, pulling it out again to spread her wetness over her clit.

"But, she graduated before me and moved away. I still follow her on Instagram."

I imagined pulling out my cock, grabbing her by the hips, and pushing her down on it. She seemed to read my mind because she shook her head.

"No touching, Mike. Your mistress wouldn't like it. Mine wouldn't either, for that matter," she purred. "My new mistress actually got me the job here. Her husband is on the board. Don't tell anyone, but I think she's hoping I'll be like a spy for her and get some info that would let him take control."

Some part of my brain recognized this as important information, but I was in no position to process it. She pushed another finger inside herself and started thrusting her hips, enjoying making me watch.

"She makes me flirt with her husband. She bought me a maid outfit. She has me go around with a feather duster and bend over in front of him. Sometimes she fingers me first, until there's a big wet spot on my panties. Other times she takes them away so he can see my pussy. Then she comes in and pretends to be shocked when she catches him watching me with a hard-on."

"Does he know?"

"Oh yeah, it's a game for the two of them."

"What, uh," I was having trouble concentrating while watching her finger herself. "What does she do when she catches the two of you?"

"She calls us names. She makes me go down on him. She says stuff like 'Is this what you want? You want this little slut to suck your prick?' It makes his cock so hard in my mouth."

Kara closed her eyes and moaned at the thought.

"She yanks down my top and pulls on my nipples until I squeal. 'Let's get this bitch's tits out. That's what you want to see, motherfucker? You get off thinking about her little tits?'"

Abruptly, she reached down and grabbed my hand, pulling it to her chest.

"Maybe it's okay if you touch me a little, Mike, but don't touch yourself."

I nodded eagerly as I groped her. I could feel her nipples harden through her dress and wished I could suck on them.

"She pushes my head down on his cock until I choke. 'Look at this slut, she loves it. Fuck, I bet she's dripping wet.' Then she reaches behind and shoves a finger in me and says 'I can't believe how wet this cunt is right now! She's been prancing around all day fantasizing about this instead of doing her fucking job.'"

"Oh my god," I moaned, watching her rub tight circles around her clit.

"Right? Sometimes she spanks me. It turns me on so much getting spanked while I suck her husband's cock. Between swats, she fingers me, alternating pleasure and pain. 'Listen to her moan! The little tramp is getting off on this.'"

I groaned, struggling to resist the urge to do more than touch her chest.

"Then she makes me climb in his lap and ride him while she berates him. 'Is this what you wanted? Is this why you got hard when she bent over and presented herself to you? Did you imagine burying your thick prick in her tight little pussy? Don't cum in her, you dog. I know she's a thirsty little slut who's only good for filling with spunk, but don't you dare.'"

"Fucking hell," I gasped. My cock twitched, and I felt a squirt of precum soak into her panties.

"Yeah. Sometimes she fingers my ass, too. She knows it makes my pussy clench, and it gets him right to the edge." Kara bit her lip, then laughed. "This one time, she stuck the handle of the feather duster up there while I was riding him."

"What'd you do?"

"I screamed and came all over him. Then he came inside me. She was furious with him. Normally she makes him cum on my face or my tits. She made him lick it all out of me."

"No!"

"Oh yeah," she purred, leaning into my hands. "It was so fucking hot. I think he was into it, you know. Some guys are. After that, she made him sleep on the couch while she helped me shower and let me stay the night with her in their bed."

"Kara, fuck..." My cock felt like it might explode. "I need..."

"I know. Pull down your pants. I want to look at your cock while I cum."

Eagerly, I lifted my ass and shoved my pants and boxers down around my ankles. My cock reached straight up, still wrapped in her thong.

"Fuck," she exhaled. "I wish I could give you what you need. But your mistress will not be happy if I ruin her fun." She pulled her fingers out and let me suck on them, coating my tongue with the taste of her pussy.

I groaned, and my cock twitched, straining for her.

"But I guess it wouldn't hurt for you to finger me if you promise not to... Ah!" Before she finished, I had two fingers inside her.

"Oh fuck, you're eager," she gasped, bucking her hips to fuck against my fingers. I pressed up, awkwardly trying to grind my palm against her clit while still fucking her.

"He really is," said Liz from behind us.

Kara squealed and jumped away from me, tugging her dress down. Turning around guiltily, she found Liz leaning on the counter. She had a carefully neutral expression as she looked from Kara to me. My pants were bunched around my ankles, Kara's wet panties wrapped around my cock, and I was shamelessly licking my fingers clean.

Calmly, Liz walked around to the door and let herself into the room. She stood there for a minute, trying to make up her mind how to handle the situation. I couldn't help but notice her nipples were poking through her dress.

"How long were you there, miss?" Kara whispered.

"Long enough to get interested," Liz replied. "I see that beast hasn't calmed down any," she observed, as my cock continued to throb with my heartbeat.

"I wouldn't let him touch himself, or help him cum," Kara said with a bit more confidence. "I told him you wouldn't be happy."

Liz nodded approvingly. "And what was it you called me?"

"His, um, his mistress."

"Well, I don't hate that," she purred.

"Liz," I started, but she cut me off.

"I'll deal with you later."

"But I didn't do anything?"

"Only because she stopped you."

I frowned. Kara bit her lip and looked pleased.

"Now, Kara, while I'm grateful you managed to keep Mike under control, you did get distracted from your job. I left him here to calm down, and I come back to find you both too aroused to think straight. If someone else had come up to the coat check, we'd be having a different conversation."

Kara hung her head.

"Okay," Liz said after a long minute. "Mike, poor Kara here tried to be a good girl, but you distracted her. Now she's so turned on it's literally running down her thighs."

Kara's face turned bright red, and she squeezed her knees together.

"So you need to make it up to her. But Kara, Mike here is uncontrollably erect because of a pill I asked him to try. He was already having a hard time before you started telling him about your adventures. So you need to make it up to him a bit, first."

"Yes, miss." Kara hesitated. "What do you want me to do?"

"To start, I want you to get on your knees and suck his cock. And don't touch yourself. It's not your turn, yet."

"Yes, miss." Kara dropped to her knees in front of me. Her eyes glittered with excitement.

"Mike," Liz cautioned. "You are not allowed to cum. If you're getting close, I expect you to let Kara know so she can slow down. You'll get yours later."

I nodded vaguely, barely able to think straight as Kara licked her lips and stared at my cock.

"Mike," Liz warned.

"Uh, yes!" I looked Liz in the eyes. "Yes, I understand."

"What about the coat check, miss?" Kara asked.

"It's a little late to think of that now, but don't worry. The party's just starting to wind down. I came out early to check on Mike. Still, you are a bit exposed." She grabbed one of the rolling coat racks and positioned it to block the view from the counter. "Now, I'll manage the front while you two get started." With that, she disappeared behind the coats.

"I told you she's your mistress," Kara mumbled, pleased with herself as she removed her panties from around my cock.

"No, she's--oh!" I gasped as she wrapped her lips around my head. The heat of her mouth felt incredible after being denied any stimulation for so long, and I immediately forgot what I was protesting.

Kara quickly fell into a rhythm, one hand wrapped around the base of my shaft and the other cupping my balls. I felt a building pressure, and she moaned happily as a squirt of precum coated her tongue.

"Fuck, Kara, you better slow down," I reluctantly mumbled. Disappointed, Kara rocked back, releasing my cock to slowly lick up and down my shaft. I felt the pressure recede a bit. "You're really fucking good."

"Thank you," she purred. "My mistress gives me a lot of practice."

"Was all that stuff you said true?"

"Every word of it."

"You weren't just teasing me?"

"I mean, I was doing that too, but it was all true. I think the reason it excited you so much is you've got a little submissive in you, too. I see the way you respond to Liz. Admit it, you like it when a woman tells you what to do."

"Uh, I guess that's kinda true."

"Does Ms. Sandstrom also tell you what to do when you fool around?"

"Yeah, sometimes."

"And does it turn you on?"

"...Yes."

"There you go," she concluded, taking me back into her mouth.

A moment later, Liz walked around the coat rack with a claim ticket and grabbed a couple items. She leaned over to whisper in Kara's ear. "Try to go deeper."

Kara moaned and changed her angle until I felt my cock bump against the back of her mouth. Liz winked at me and bustled back around to the counter. I tried to keep from groaning loudly as Kara swallowed and bobbed her head.

"Kara," I gasped, wrapping my hand around the back of her head. She was determined, rocking back and forth. I grabbed her ponytail and she nodded, squeezing my thighs as I pulled her closer. Abruptly, my cock slipped deeper and we both grunted as her lips reached the base of my shaft. Her throat was hot and tight and my cock was throbbing. She gagged, but let me keep holding her in place.

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