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Boss Lady

"Being the downtrodden live-in chauffeur for a sexy, slutty, self-centered celebrity has its rewards."

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The door popped open as the shapely blonde and the handsome stud approached the car. The spaghetti straps of her little black dress were challenged by her full bust, and the hemline showed more of her legs than if she were wearing his white shirt. That shirt was half unbuttoned and his tie draped loosely as she had started undressing him before they left the club. She dove inside and he followed. An older, smaller limousine, the seats formed an “L”, with the forward-facing seat at the back connecting to a long bench seat facing the door. It gave her more room to stretch out.

Already on her back, she pulled those straps down to release her tits. Shrugging off his jacket, the guy unfastened his belt and shoved his pants and underwear down to his knees in one move. Lifting her skirt, he lowered his face between her legs, but she grabbed his head and pulled him up.

“I’ve been humping your leg for an hour,” she moaned. “I’m ready. Put that thing in me.”

Two groans sounded as he slid easily into her well-lubricated slot.

“Come on, fuck me!” she demanded when he started slowly. He picked up the pace as she raised and spread her legs, their grunts and the slapping of flesh the only sounds.

Her voice was like a whinny when she peaked, but she gasped, “Keep going, I’m not done.”

Sure enough, there were two more like it as the guy kept pounding. After the third, his growl signaled his eruption; her sigh could have been satisfaction or disappointment. In any case, he slowed and settled on top of her.

There were no words, no cuddling, just two sweaty bodies pressed against each other in the aftermath. It was hardly a minute before the sound of her snoring broke his daze.

Lifting himself off her, he looked down at her slack face and disheveled body and decided there was no need to prolong things. He quietly opened the door and slipped out, only managing to get his pants back up when he got to his feet outside the car. The door clicked shut.

“Home, Boss?” I said softly, expecting no response. Waiting until the guy disappeared back inside the club, I started the car and drove off.

Parking in the attached garage meant nosey neighbors and paparazzi with drone cameras wouldn’t see us arrive. She hadn’t stirred since we left the club, so I figured she was out for the night.

On my knees, I slipped one arm under her shoulders and the other under her legs and worked my way back out of the car. Setting her down in the doorway, I got to my feet, wedged my shoulder under her arm around my neck, and carried her into the house. She stirred a little, not really waking up but holding on and making it easier.

“We’re home, Boss,” I said, laying her in her bed. Rolling her on her side let me unzip the back and pull her dress down and off her body. Laying it on a chair, I covered her, turned off the light, and left her. “Goodnight, Boss.”

You know who she is. I’ll call her Holli Wuud so you won’t know for sure since there are at least a dozen women who fit the same description. In her thirties—more or less—she has always liked to party. Using her talents, both professional and personal, she has become famous enough and rich enough to have the life she wants.

Her previous driver was a friend of mine. When he got engaged, he knew he had to quit and recommended me. I almost lost the job the first day. While holding the door open for her to get in, she asked me if I knew how to get to a particular private nightclub.

“Yes, ma’am,” I said.

She turned and slapped me across the face as if I had called her a cunt.

“You’re fired,” she snapped, then paused long enough for me to think she was serious, before smirking, “if you ever call me that again.”

For years, I had called my passengers “sir” or “ma’am”. She wanted me to use “Holli” and hated “Ms. Wuud” almost as much as “ma’am”. It just didn’t seem right to me, especially in front of other people. We finally settled on “boss” as the non-sexist, respectful way to refer to her.

The job was sort of a throw-back. Like a coachman, I lived rent-free in a cottage behind the garage and was at her disposal any time, day or night. Some parties started after midnight, and I almost lived in the car as I waited for her.

There were perks. It gave me an inside view of a lifestyle I had only imagined, including her active and varied sex life. I was totally free when she was away traveling or skiing or on some yacht, sometimes for weeks at a time.

Long before I showed up, she had decided she didn’t need any more DUIs and hired a driver. When she realized the limo could be a portable motel room, she bought this one. Older and too small for groups, it was perfect for a quick fuck at an event or on the way from one party to another. She could get laid, drunk, high, or some combination and know that she was safe and would make it home—if she wanted—at the end of the night.

To avoid intruding, I would stay out of sight, the divider seeming to give her and her guests privacy. There was even a button for her to press to talk to me. But the cameras and microphone let me observe and respond to her whether or not she pressed it.

The first time I carried her to bed was after a studio party at a hotel. She had returned with an older guy in an expensive suit to where I waited in the parking structure. They stopped behind the car and she dropped from view. He leaned on the trunk with one hand for a couple of minutes. When she stood up, he didn't even touch her before turning and walking back inside.

"Asshole producer. Said he'd get me a part," she complained, pouring herself a drink and rinsing her mouth before she swallowed it. Already slurring her words, she had a few more as I drove home.

She was passed out when I turned off the car. It was a cold night, and I didn't think I should leave her in the car. Nothing I did roused her, so I decided I would drag her inside. Completely limp, once I got her out of the car, there was nothing to do but carry her.

I whacked her head a few times going through doors, but she would hardly notice with the hangover she was due for. Initially, I headed for the couch but figured she'd be more comfortable in her bed. She hadn't yet undressed in front of me and her clothes were all in place, so I left her that way, although I did slip off her shoes.

Later I learned her modesty was less important than her expensive dresses that she could easily rip in her sleep. If she was half-asleep, I would help her undress—she rarely wore underwear. If she was totally out of it, it was easier to strip her than to wake her.

Holli liked sex a lot with a lot of different partners but was pretty traditional—at least what I saw in the car. One man at a time was the usual. A few times she was buzzed enough to play around with a woman, but it was more silly than sexy.

One time, she brought in a couple. You know their names; I’ll call them Oscar and Emmy. It wasn’t exactly a threesome, but some kind of bet. The event was a casual barbecue. All three wore slacks but were swiftly naked.

Emmy was on her back and Oscar immediately started licking her pussy. "Three times," she told him. "I hope your tongue is up to it!"

“Hey, I didn’t say ‘go’ yet,” Holli protested, settling into the back seat where she could watch Emmy’s face. Playing with herself with one hand between her legs and the other grabbing a boob, she tried to catch up.

Both women were breathing heavily and moaning within minutes, but Emmy peaked first.

“Shit!” cursed Holli. “I know you aren’t a good enough actress to fake that.” Oscar raised his drenched face to laugh. Apparently, Emmy needed to rest because he didn’t dive back in.

“There it is,” Holli groaned as her fingers danced over her snatch. It seemed the couple was familiar with her orgasmic song because they didn’t dispute it.

Holli had barely paused and was using her juices to forge onward. Bending one leg up to her chest, she reached one hand around it to fuck herself with her fingers while the other hand ground against her clit.

“Let’s go,” Emmy whined to the distracted Oscar. Tearing his eyes away, he went back to working on his partner.

It was usual for Holli to want more than one climax, so it was not a surprise that she reached her second before Emmy did. Despite a mouth and four hands stimulating her, it was not a close heat.

“Keep going,” groaned Emmy when Oscar took a breath after she matched Holli. The way she squirmed, she might have been better off with a brief rest.

Meanwhile, Holli relaxed and stretched out. She had fetched a dildo from a drawer and was sliding the realistic, if supersized, organ in and out of her dripping hole.

“That’s cheating!” exclaimed Oscar when he noticed it. Before Emmy could react, he moved up between her legs, shoved his cock into her cunt, and started fucking wildly.

As their bodies gyrated, it was easy to see the difference between Holli’s real tits and Emmy’s enhanced—although she denied it—pair. Holli’s rippled while Emmy’s bounced.

The grunts and gasps got louder. With Emmy’s legs around him, Oscar was plowing her as deep and hard as Holli was doing with her implement.

“I-win-I-win-I-win,” my employer neighed as she wiggled in ecstasy.

That seemed to launch Oscar and his grunting ejaculation did manage to get Emmy across the finish line. She wanted to protest, but the pleasure hormones that soaked all three convinced them to argue it another time.

A few months later, Holli had been water-skiing and jet-skiing with friends. She was worn out when I brought her home, so I didn't expect a call, but I never knew when she might get a text about a party.

Her voice on my phone was anguished. “Come to my bedroom! Hurry!”

Wearing sweats, I had just opened a beer to watch a movie, but I ran to the house. She was sitting on the side of the bed, grabbing her right leg—completely naked.

“Cramp,” she groaned. She was trying to stand up to stretch it out, but couldn’t get her balance and I was worried she was going to fall.

“Lay back,” I said, bending to grab her leg. With her ass at the edge, I raised her leg straight up. Putting one hand on her foot and keeping her knee straight with the other, I leaned to stretch out the knotted muscles.

Her angry yowl turned into a whimper as the spasm relented.

“Relax, breathe,” I calmed as I moved her leg, gently testing the limits of her range of motion.

After a few deep breaths, she focused on me. “Why are you staring at me?”

Indeed, my eyes were glued to her face. Once the urgency passed, I had time to see her full breasts gazing up at me. Looking instead down the leg I was holding gave me a great view of her bald, open pussy. I had seen her naked before, but never like this and not while she was watching me. Her unhappy face was all I had to fend off my growing erection.

“Sorry, Boss,” I apologized. “Just making sure I didn’t go too far.” She didn’t react to my ambiguous comment as I lowered her leg.

“I overdid it today, and now my muscles are punishing me,” she sighed. “It’s too late to call Jason,” she named her customary masseur. “Do you know how to give a massage? I don’t mean foreplay, I need therapy.”

“I’m not a professional, Boss,” I admitted, “but I do know the difference. On the wrestling team, we would do each other.”

Since then, I’d had occasions to apply my skills to women.

“I don’t need you to suck my cock,” she wise-cracked. “I need you to relax my muscles so I can get to sleep. I have to be up early for that interview and don’t want to look like shit.” She shook her head as she looked me up and down. “Get the massage table and we’ll see how it goes.”

I got it out of the closet and set it up. She laid face-down, which let me do her arms, shoulders, feet, and legs without getting close to anything sensitive. A few words and soft moans calibrated me to the pressure she wanted. Her sweet ass beckoned me and I had to adjust my pants several times to defuse my hardon.

Her thighs and butt were the sorest since she had been water-skiing. Her ass was soft but not flabby and my fingers pressed into her flesh. My hands were slippery from the oil as I stroked her inner thighs.

She seemed completely relaxed and I thought she might have fallen asleep. I had decided how to lift and carry her to her bed if she was before I asked, “Is that okay, Boss?”

Lifting her head, she started to roll over, saying drowsily, “What about my happy ending?” On her back, she squirmed into the middle of the table. Suddenly her eyes opened wide as she looked at me.

“Shit, I forgot you weren’t Jason,” she laughed. “I’m so relaxed, it would be a shame for me to get tense to get myself off. Usually, he would finger me. Are you up to it?”

My normal inclination would be to discuss crossing a boundary like this first. I didn’t want to lose this job or screw things up between us. As far as I knew, she was sober, although sleepy. Insecurity made me want to ask if she was sure, to be certain I understood what she wanted. But the wrinkled lips peeking out from the divide in her smooth mound were too tempting.

Slipping my hand between her thighs, I slowly slid upward. Her legs parted slightly, giving permission to proceed. It wasn’t the first time I had massaged a woman and given a happy ending; despite never expecting to be doing it to this woman, I recalled a detail that made me stop—massage oil wasn’t intended for vaginas. I quickly wiped my hand on my sweatpants then licked my fingers before reaching to part her lips.

As I gently explored, I discovered sufficient dampness to allow my fingertips to glide over her folds. My other hand skated over her belly and sensed no tension as I probed deeper. Finding her opening and probing inside confirmed the source of the wetness. Her deep even breathing showed her trust.

Having scouted the territory, I began to work on her in earnest. Her eyes were closed and her face relaxed in a satisfied smile. Before long, her flesh was slick with her lubricant, sliding easily between my fingers. A soft moan accompanied an impatient shifting of her hips. Using two fingers, I breached her entrance and spiraled my way in, the heel of my hand resting above her clit when I could go no deeper.

She squirmed to meet my caresses as I alternated bursts of thrusts with flurries of twists. So focused on my right hand, I was surprised when she took my left and moved it to her breasts. I hadn’t dared to stray that far north, but my palm discovered the stiff nipple atop that squishy mound. Her gasp as I pinched it told me it was the missing piece.

She began to make the sounds I had often heard in the car. I paid tribute to both nipples with one hand while the other stirred her cunt. The back of my mind was trying to enjoy the sight, sound, and feel of this beautiful magnificent woman who was being pleasured by me; the front was desperately hoping I didn’t do something wrong before I got her across the finish line.

The rising pitch of her moans and tension in her thighs told me she was close. I kept everything going, maybe a little faster, maybe a little harder. I might have mistaken her culminating vocalization for a giggle except for all the times I had heard it before. It was music to my ears as the orgasm gently contorted her body. I felt so proud that I was responsible for her goofy grin. Knowing her usual preference to continue, I slowed but didn’t stop my hands until she covered mine with hers.

“One is enough tonight,” she cooed. After holding me in place for a few deep breaths, she released me and sat up. “Help me get to the bed,” she said groggily. Steadying her on her feet, we took the few steps and planted her on the mattress. Taking one last longing look at her luscious backside, I pulled the sheet and blanket over her.

Deciding not to risk disturbing her by cleaning up, I just turned off the light and left. Outside her door, I couldn’t wait to sniff and lick her excretions. Needless to say, my cock was rock hard when I returned to my room. Without bothering to get lube, with my fragrant hand over my face, the other yanked my dick into the best orgasm in quite a while, solo or otherwise.

In the morning, I checked that she was awake in time to get ready for her interview. She was on her phone when I pulled the car around to pick her up. Halfway to our destination, she had finished her call and I saw her meet my eyes in the rear-view mirror.

“Even if it doesn’t mean you have a big dick, I’m glad you have big hands,” she laughed, her only acknowledgment of what happened.

It felt to me we had crossed another line that night, but I don’t know if she ever thought of it that way. She always just did what she wanted without any regard to rules or conventions. If that had happened my first week on the job, I would have balked but, by then, I had seen, touched, and carried her practically naked body on multiple occasions.

So maybe it was just a coincidence that things seemed to me to progress over time.

She probably never thought about the hold she had over me. I would do or put up with whatever she wanted. When she would insult or mistreat me in some way, it wasn't to intentionally cause me pain. Only caring about herself and only acting in the moment, she just did what she wanted, unaware or uninterested of how her behavior affected me or anyone else. One time, she sent me across town for her favorite sushi but, before I returned, she had left to party with some friends. It simply never occurred to her to send me a text and cancel my mission when she changed plans.

Her saving grace was her laugh. Even when it seemed targeted at me, she exuded such joy, I wanted to share her happiness. Whether she was reaming me out for not stocking the latest vodka in front of the guy that she wanted to impress or fuck or both, leaving used condoms and various bodily fluids from her evenings for me to clean up, or forgetting that I was waiting for her at one club when she went with friends to a different one and chastising me for not being at the second one, it was just the price of a front-row center ticket to the show that was her life.

The afternoon open house party at the producer’s mansion wasn’t her favorite thing. She was invited mostly to liven things up for the A-list celebrities and business bigwigs. It let her make and maintain contacts with people who could help her career, so she wore underwear and stayed sober.

The sun was setting when she arrived with a young guy in tow. I didn’t recognize him, so I wasn’t sure why she chose him until she got him inside. She grabbed for his belt and zipper and in a flash had extracted a substantial organ. Slurping it into her mouth quickly expanded it to porn size. She gagged a little trying to take it all, but I knew how she would want to use it.

Pulling her tank top off over her head and unhooking her bra had him mesmerized by her majestic melons. In this town, there were so many boob jobs; I think some guys didn't know what real ones were like. While he stared, she unzipped her skirt and pushed it and her panties down and off her legs.

“Get your clothes off,” she urged, laying back and spreading her legs.

“Oh,” was all the guy said when he realized he was just sitting there with his mouth open. He stripped off his shirt and pants in record time.

“Oof!” she grunted as he climbed on top of her. “That’s big. Give me a minute.” She squirmed underneath him, but her hands on his butt urged him deeper.

“That’s it,” she sighed as they began to move together. Before long, she had bent her legs up, knees wide, heels on his ass. He was pounding into her so hard I could feel the car shake.

“Oh, yeah, give it to me,” she gasped.

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Whether he misunderstood and thought she wanted him to do it or whether he just lost control, his loud groan and series of grunts announced his eruption. She wasn’t the type to fake an orgasm and probably assumed she would get another opportunity. But he slowed his thrusts and it became apparent that his cock was deflating.

Undeterred, she slipped out from under him, rolling him on his back and seizing his still substantial sausage. Squeezing and sucking, she tried to resurrect it. Despite several minutes of her skillful suckling, it remained a wet noodle.

“Sorry, I guess I was too excited by the chance to fulfill one of my fantasies,” he bemoaned. “You’re so hot!”

“Too bad it ended up being one of my nightmares,” she was unassuaged by his attempt to cover his failure with a compliment. Pulling a short robe out of a compartment, she moved to the rear seat. “You should go.”

He quickly dressed and left.

Interspersed with a dozen assorted profanities, she griped, “I can’t go back in and find someone else. Take me home.”

Depending on traffic, it would take an hour or two to get back to her place. As I drove, I heard the sounds of her annoyance and her downing a few drinks from the bar.

After twenty minutes or so, she called to me, “Find a place to park and come back here.”

The businesses along the road were closed for the day, so I found a spot behind a deserted building where we wouldn’t be seen. My job included cleaning and restocking her compartment. Based on her mood, I was worried she was going to reprimand me for some problem.

"Get in," she ordered when I paused, holding the open door.

The short robe was wide, leaving her fully exposed as she lay along the side seat where they had fucked. The placement of her hand suggested she had been fingering herself, apparently without success. Her nipples were hard and her face was flushed with excitement or the alcohol.

“That cock got me so turned on then left me high and dry,” she wailed. Then she laughed, “Actually, I was sober and quite wet, but you get the idea. You did such a good job after that massage the other night; I hope you can get me off. My hand is tired and my clit is sore and I’m getting more and more frustrated.”

Before I could consider if or how I should do anything, she dropped her right foot to the floor and bent her left knee up, opening her pussy. It was hard to resist burying my face in it.

“Relax, Boss,” I said soothingly. One hand gently stroked from her neck down; the other, from her thighs up. “Don’t try so hard.” My hands flowed over her breasts and belly. “I’ll take care of you.” I first kissed then gently sucked her nipples while my hand roamed her inner thighs and mound.

A soft moan finally indicated she was back on track, so I kissed my way down her torso. Giving her clit a rest, I massaged her outer lips. When I parted them, I found the leftover stickiness. I licked my fingers for my benefit as well as hers before swirling them into her opening.

Applying my tongue to her slit, I flicked teasingly, not wanting to overdo it. Instead, I focused on locating and probing her g-spot. The way she began to squirm, I was sure I had found it, so I kept at it.

“That’s good,” she sighed when she realized my intentions.

Applying my mouth to her apex, I drew her nub between my lips but let the internal drumbeat lead the way. Her familiar mewl told me she was building her excitement.

“Oh… oh… ooohhhhhh!” her voice echoed my surprise at how soon it arrived. My fingers felt the contractions and the flow that dampened the robe beneath her butt. Always music to my ears, her high-pitched staccato cry of pleasure confirmed her climax.

Assuming I was done, when she settled down, I withdrew my fingers and happily sucked them dry. I expected to get back on the road, but Holli had other ideas. From watching her many encounters in the car, I should have realized that once was never enough and two or three were the usual.

“Lay on your back there,” she grinned, pointing to the floor.

It all happened so fast I hardly had time to appreciate the view as she stood astride me. Looking up past her shapely legs and thighs to her round ass, my brain recorded it in slow motion as she squatted over me, opening and lowering her glistening cooch onto my face. Too soon, the glorious sight was obscured by her ass cheeks on my forehead, but it was displaced by the overwhelming scent and taste of her hot flesh against my face.

She steadied herself and gave me enough clearance to breathe and move and make use of my tongue and lips as I explored her folds. In reflex, I thought to reach for her unseen dangling boobs, but in the narrow strip of floor between the seat on one side and the bar cabinet on the other, my arms were trapped by her legs.

My face was bathed in her natural extracts, perhaps augmented by the delay in her release or the stimulation of her g-spot. As she squirmed and painted my lips and cheeks with fluids, my nose and tongue recognized an unexpected condiment—semen.

I had forgotten that the cause of this situation was the guy who came but didn't satisfy her. I tried to ignore it; just because I don’t like mustard doesn’t mean I’ll throw away a juicy cheeseburger. Happily slurping and nibbling a pussy I never expected to see up close, I wondered if Holli even gave it a thought.

If she had, it was likely soon forgotten as her libido reasserted itself. It became less that I was eating her and more that she was humping my face. From her asshole to her clit, from my forehead to my chin, she mashed every part of her against every part of me. There were long seconds of breathlessness as she negligently smothered me, concerned only with her pleasure, but her gasps became as loud as mine as she worked herself to another peak.

Her squeal of ecstasy came with another shower of nectars. She settled from a squat to a kneel as she leaned on her hands, sighing with pleasure. Although pinning my arms, it gave me room to breathe and to lap at her slick pleats.

In no hurry to escape my captivity, I was startled to feel her tugging at my belt. Needless to say, my cock had been trying unsuccessfully to burst out of my pants. She had a lot of experience doing so and quickly had my pants down enough to take my rod in her hand.

In my current position, the word inconceivable had lost all meaning, but that’s how it seemed that she would pay any notice to my ordinary organ. I knew I wasn’t worthy of her attentions, but I was too stunned—in the most delightful way—to do or say anything.

Holli briefly sucked the tip, certainly finding the pre-cum I had surely been producing since I touched her body. She squeezed and tugged, perhaps trying to decide if it would get any larger.

“That’s all I have,” I chuckled. On a good day—and this was a good day— it was technically longer than average. More noticeable was its thickness, more like a beer can than a long-neck bottle.

“Well, I want one more, so let’s see if it works,” she giggled.

When she stood up, I thought I could get off the floor, but she wasted no movement turning around and squatting on my pole. The shock of the sudden hot wet grasp made me worry I would shoot immediately, but she leaned forward, one arm on the seat, deciding if it was worth rearranging.

She started to bounce and my hands leapt to her swinging tits. Her orbs overflowed my large hands and I flicked and pinched her nipples as I kneaded their softness. Grinding herself against my pylon, she rode me with a steady rhythm. I thrust to meet her as best I could with my limited range of motion.

Fortunately, her subsequent orgasms didn’t take as long as her first, so I didn’t have to hold out for too long. She closed her eyes and leaned backward, sadly taking her boobs out of reach, as she moved faster. Propping herself on the seat and one arm behind her, her cunt pressed hard against the top of my shaft, giving her more of what she needed without giving me too much.

I had seen this face before, the unfocused stare with the grimace of anticipation, but I’d never been the cause. Despite knowing how fleeting the moments of exhilaration are, they ticked by slowly as I watched her body convulse gracefully. The wonderful melody of her fruition spread warmth through my chest.

Whether it was my hesitance to assume she would want me to do so or the distraction of watching her rapture, I stayed on the edge but did not go over. As soon as she regained her senses, she rose from the less comfortable squat and flopped on the seat.

“Let’s go home,” she said drowsily. She watched me get up and seemed to notice me stuffing my still raging hardon into my underwear but said nothing.

Napping for the further hour it took to get there, she revived when we exited the freeway and put her clothes back on before she had me pull up to her front door. She hopped out, leaving me to park and clean the car as I would after any other outing.

But I jerked off three times that night with the robe, damp and redolent with her essence before I tossed it in the laundry.

You know who the musician is, too. But like Holli, I could tell you a lot of details and there would still be dozens of possibilities. Over time, she fucked more than a few of them. I’ll call him JK.

He had acquired cash and fame a few years earlier with some sizzling beats that became standards. Like Holli, he was enjoying success, working just hard enough to keep things flowing. I sensed compatibility on multiple levels when I drove them to a series of clubs and parties on a few occasions.

Although they had never done it in the car, I assumed they did elsewhere based on how they acted in public as well as the way they talked as I drove.

“Home,” she texted me from the back when he sat next to her in the rear seat. She would do that when she didn’t want to interrupt her mood. As far as I knew, it would be his first visit to her place. They were getting hot and heavy as I drove but were still clothed when I dropped them at the front door.

“Stay on call,” her text beeped as I parked the car. She would warn me not to undress if she thought she would be going back out. Sometimes when she had a visitor, she’d have me go pick up dinner or something. I didn’t think anything of it but had a soft drink instead of a beer.

It was over an hour before I got the next text. “Bedroom.” Expecting a food order, nothing was unusual until I stepped into the room. Then everything was.

Holli stood there as I had never seen her before. The sheer black teddy left nothing to the imagination; both it and the black stockings were uncharacteristic for her. She usually dressed for comfort, style, and practicality. The way she laughed at my expression, I figured it was some kind of joke.

My shock at seeing her dressed that way was immediately exceeded at the sight of JK. He was naked with his hands cuffed behind the back of the chair he was sitting on. The string of expletives he was generating showed he wasn’t expecting my arrival.

Holli’s mirth was clearly multiplied by both of our reactions, mine being less vocal. “You can leave any time you want,” she said, leaning and pressing her chest against his face.

When he quieted down, she continued, “We’re going to resolve our bet.” She said it to both of us, but I had no clue what she meant.

“Take your clothes off,” she instructed. Even more clueless, I quickly stripped. “Look at that little cock,” she ordered. A glance at his lap confirmed who she was talking about. Obviously not fully erect, still his was longer and as thick as mine would get. Engorged, it would dwarf my best hardon, although, at that moment, her characterization made mine shrink in embarrassment.

She nodded for me to turn towards him so he could confirm my inadequacy. “No way,” he growled.

“We’ll see,” she said. Fortunately, my poor penis had not found a way to flee my body because she peeled the garment down her torso, freeing her marvelous mounds. Sitting on the edge of the bed, she pushed it down her legs, scraping the stockings off as well.

"We don't need that anymore," she snickered. The costume had apparently served its purpose in getting JK to agree to be handcuffed. By the time she stood naked and stretched her arms toward the ceiling seductively, my dick had achieved its maximum dimensions and throbbed in anticipation—of what, I had no idea.

“Tony,” she almost never used my name. She stepped to me since I was immobilized by the situation. “You’re going to fuck me.” Her hand stroking my chest made my heart race faster. “If you make me cum with your cock, you can fuck my tits. You can give me a pearl necklace.” Her laugh showed her total delight, which I shared despite expecting it to ultimately be at my expense.

Each of us looked back and forth at the other two, Holli chortling, JK swearing, and me trying not to hyperventilate. She climbed onto the bed and positioned herself so he would have a good view. It took her beckoning to unfreeze me, and I timidly approached her. She spread and bent her legs slightly.

“No coaching,” JK interjected, “and no faking!”

“As you discovered, I never fake an orgasm,” she sneered in response.

“Just do what you would normally do,” she encouraged me. Her confidence in my abilities was unjustified. In the year or so that I had been working for her, my opportunities had diminished and I was out of practice. In the months since she rode my pole in the car, it had been only my hand and imagination.

Luckily, my fantasies included foreplay. Surveying her luscious body as I knelt between her feet, I could see she needed to be warmed up. Unsure of myself, I lifted one leg, resting her ankle on my shoulder as I massaged her leg. Going as far as cupping her buttcheek with my outer hand, I stopped inches short of her crotch with my stroking fingers on her inner thigh. Repeating with her other leg, I then settled on my arms between them.

Skipping her genitals for the moment, I bent to kiss and nuzzle her belly, tracing her ribs as I worked my way to her breasts. Her nips were poking up before I got to them, but my lips sucked and chewed them to full stiffness. As much as I wanted to continue upward and kiss her on the mouth, I sensed that wasn’t what she intended—this was sex, not love.

Her sighs and occasional whimpers were a good sign, and I slipped a hand downward before deciding to move on. Tracing her slit revealed some dampness so I moved to increase it with my mouth. She twitched as my lips grazed her smooth vulva.

“No fair licking your clit,” JK interrupted. “Anyone can make you cum that way.”

I lifted my head, but Holli pulled me back down. “Don’t be insane,” she protested. “Of course he can lick me.” Releasing my head, she spoke softly. “Just don’t overdo it. It’s your cock that matters.”

I didn’t pause to check, but that last comment may have made it grow another inch as it danced in readiness.

Lifting and spreading her thighs, I dove into her folds, reacquainting myself with her flavor and aroma. “What I normally do” would have been to bring her to the verge of a climax, if not through it. Instead, I kissed and nibbled her sweet flesh with only an occasional slurp that sent a shiver through her.

Approaching the moment of truth, I moved up her body, briefly revisiting her bountiful boobs before my pole prodded her pussy. I pushed a bit into her entrance, taking my time working my way inward. Before I reached my limit, I lifted both legs, hooking my arms behind her knees, angling her channel upward, and opening her to get the maximum depth.

I had watched her get fucked dozens of times, so I knew her preferences. She had climaxed on a smaller, thinner cock than mine, although the fact that it belonged to a potential producer for her next project may have increased her excitement. But I could read her responses, knowing when she needed to coast, when she wanted to be pushed, when she was on final approach and more of the same was better than something different.

In the moment, JK disappeared; the promised reward was forgotten; it was just feeling and seeing and hearing and tasting and smelling Holli. I half wanted to hurry up and make her explode, and half wanted to keep going forever.

The familiar lusty smile spread on her face. It told me she knew she was there. Her fuse had been lit and there was no way to stop it. The difference was her eyes locked on mine, and it almost made me explode. Taking a deep breath as I prepared to continue thrusting through her orgasm moved me back just enough.

Her legs tightened against my arms and her ass bounced up from the bed as her cunt gripped my dick. If I had been able to consider my options, I would have emptied my load inside her. It was my fondest dream. But it wasn’t hers. Besides, the path had already been decided, so I resisted as I drilled her through her writhing and her equine exclamation that demarked her rapture.

Only that sound echoed in my ears until I became aware of the deep rumble of profanity from our spectator. He had lost the bet. The sound also roused Holli from her brief reverie.

“Ha! I win!” she crowed. “I win twice!” she added, looking at me. “It might not get any awards, but it certainly got the job done!”

I was in no hurry to extract my penis from the delightful grasp of her vagina, but she lowered her legs, ejecting me as she proceeded to the next act with no intermission.

“You must be ready to nut, so let’s not waste time,” she said, reaching for a bottle of lube on the nightstand. With a few pumps, she had a small pool in the valley between her peaks. She piled them up and mashed them together, forming a slippery crevasse.

Not pausing to wonder if I was dreaming, I gazed at the second-best place I had imagined penetrating. Swinging my legs around hers, I moved up her body until I was straddling her ribcage. Wanting to remember every millimeter of the feeling, I pressed the tip of my cock between her sweet pillows.

Considering the natural lubricant I wore and the artificial she had added, my pole slid easily into that warm and incredibly soft slit. Holli’s counterpoint as I moved gave me a full stroke, my cockhead barely emerging from her cleavage. Her apparent joy and enthusiasm quickly had me back on the edge. As before, I didn’t want it to end, but this time I knew how it would.

“Cum for me,” she reassured me, although my body was well past the point of no return. “Spray all over my tits and face.”

My groan warned of my first and largest spurt, which came as the tip peeked out, sending a jet onto her face and neck. Releasing one boob, she grabbed my shaft and aimed it at her nipple, decorating her chest with my titanium white. Milking and jerking, she extracted several days of accumulation until I had no more to shoot. She managed to squeeze a few more drops onto her other nipple.

I didn’t fully understand the glee with which she soiled herself with my jizz—until she announced, “Okay, time to lick this up!”

“Right, Boss,” I said, happy to do my duty after what she had allowed me to do.

“Not you!” she guffawed, shoving me off her before I could get to any of it. “Him!”

What had been a background of grousing became a loud “What the fuck?”

“You have to clean me up if you want a chance to outfuck that little dick,” she taunted him. Any offense passed through me in light of my recent accomplishments.

“Help him stand up on your way out,” she said.

Timidly approaching the bound man, I grabbed and lifted him under his arm with one hand while I pulled the chair from under him. Even with his hands behind his back, his towering form was intimidating, especially in the mood he was in.

As soon as he was on his feet, I grabbed my clothes and darted out of the room, not daring to watch as he bent to slurp my spunk from her body. It was dark, so I hoped there were no paparazzi with night-vision lenses as I dashed naked across the yard to my cottage.

After a hot shower, I managed to coax another few spurts from my “little” dick as I imagined what was going on in her bedroom.

Being at her beck and call twenty-four seven when she's in town seriously limits my social life. When she's away and I have time to hang with my friends, they sometimes ask why I don’t get a job with regular hours and higher pay.

“It’s the fringe benefits,” I chuckle.

 

Published 
Written by Trousseau
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