Boss's Orders by Dan Thomas

No matter what sex your boss is, it always pays to be nice to them. Sometimes it’s a good idea to be REALLY nice and do something special for them.

I think it was Benjamin Franklin who said that when it came to bedding wenches, older women were more appreciative. Ben certainly knew what he was talking about. And I might add--from personal experience--that older women can make younger men more appreciative too! You should know that I am twenty-three, single and keep myself in shape and women find me attractive. Recently I was laid off from this dotcom company after the economy went south. There I was with rent and car payments coming due. I scoured the want ads but there wasn't much. Finally I had to take this job under the heading "general clerical," for far less money than I was used to. The company I went to work for was a small real estate office. So small, in fact that it amounted to just three people: the broker who owned the place, one salesman--and me. The broker, Beth, was this plush bodied, busty, stylish ash blonde in her mid 40s. She certainly didn't dress her age. In fact, she wore these short, hip-hugging skirts and low cut tops that a lot of younger girls wouldn't have dared to. I'm sure catty women would say Beth dressed like a slut. To me, she looked mighty fine.

I'd never worked for a woman before. And when I told my drinking buddies my boss wore a skirt, they warned me to watch out for signs of bitchiness. Frankly, Beth was the best boss I ever had. She was easy going and had a great sense of humour. You wanted to work hard for her. Most days I spent behind a computer, processing sales contracts and loan applications, while Beth and her salesman were out showing houses. A lot of times I answered the phone and took messages. Usually Beth would return to the office about six in the evening, quitting time. I'd give her any messages and wind things up before going home.

One evening last week she arrived late with a dark look on her face. I could tell she was down, so I asked her if she'd heard any good blonde jokes lately.
"Just me," she blurted.
"Pardon?" I said.
"I'm a joke. A big sale I've been working on for months just fell through. I'm forty-four years old, divorced, stressed out--and if I don't get laid pretty soon, I'm going explode!" Her face blazed red. She quickly apologized, saying, "I'm sorry I unloaded on you, especially that last part. It was inappropriate."
"Nah, that's okay," I said, and meant it. She started to sob. "It's just...just that I miss having intimacy in my life," Her voice was quaking. "Just someone touching me." I couldn't believe it, a woman with her looks, I figured she had a date every night! I felt bad for her. Hesitantly I left my chair and went to her. I reached and touched her right shoulder, worried that I was crossing some kind of employer-employee line that I shouldn't. "Thank you," she said, patting my hand. Standing behind her, I began to massage her neck. "That feels so good," she moaned. I felt her muscles relax. "Here," Beth said, removing her jacket. She was wearing one of her low cut tops. I looked over her shoulder and stared at a luscious expanse of glossy cleavage, all held in place by nude coloured bra straps and lacy cups. My dick pulsed.

Beth swept her long hair aside so I could get to her shoulders. I stroked between her shoulder blades, squeezed her bare, upper arms. Then my hands massaged her soft shoulders. The woman's skin was smooth, silky. I tried not to stare at Beth's plunging cleavage, but had little luck. I massaged above her ears, the sides of her face. "You have a nice touch," she complimented me. As her muscles slackened, my dick fattened. Beth pulled her head back, exposing her throat. Gently I stroked up her throat and under her chin. My fingers went back down her throat. Damn, those fabulous tits were inches from my fingertips. "Use your nails," she said. I scratched at the creamy skin. Beth closed her eyes, a dreamy look on her face. She whispered, "Lower, please." I scratched lower, began to tickle the cleavage. Beth giggled. Discreetly I pressed my hard groin against the back of her chair. "Feels so good," she repeated. My nostrils flared from the scent of her perfume, made stronger by her body heat. Those tits...I licked my lips. My fingertips snuck lower on her chest. Beth had a smile on her face. I went for it!
My fingers grasped her generous tit mounds and squeezed. Beth's smile broadened.

The hefty hooters flopped out of their bra cups. I aggressively manhandled the jugs, thumbed the big brown aureole. "Good hands," she murmured. The nipples hardened under my ministrations. "Yes," she whispered. I began to hump the back of my boss's chair. Beth scowled. Quickly I snapped my hands off her tits and backed away with this embarrassing boner in my pants. "Sorry," I said. Beth stood, her magnificent jugs still out of the bra cups and fully exposed. She said, "Why are you sorry?"
"I thought..." my voice trailed off.
She removed her bra, looked at my groin, smiled and said, "I was just thinking we'd better turn off the lights and lock the front door, so we're not disturbed."
I grinned. "Right."
Beth crossed her left forearm over her bare boobs while she locked the front door and turned off the fluorescents.
As she walked towards me, she removed her arm and jiggled her awesome breasts at me, laughing. I reminded her there were other stores still open in the shopping centre, so someone might see us.
"Then let's give them a good show," she said. With that she pushed me against the wall and aggressively felt up my aching nut basket with her sharp fingernails. Her tits ballooned against my shirt front, and her breath came in short, hot pants against my face. We locked lips, our tongues searching for each others tonsils.

While I unbuttoned and removed Beth's top, she unbuckled my pants. Once she'd peeled my trousers down, she thrust a hand under the waist band of my briefs. "Damn!" I howled, when her fingers closed around the shaft of my erection. She snapped my underpants down and hand jacked my cock. Meanwhile, I lowered my head and planted kisses all over her remarkable tits. The freckled mammaries were weighty and playful in my hands. "I haven't seen one of these delicious things in a long time," she said, eyeing the length and girth of my erection. I tongue whipped the right nipple, sucked in on the meaty jug until my mouth was full of sumptuous tit. My tongue swabbed across to the other breast, trailing shiny spittle on the snowy flesh. Beth squeezed my family jewels. I winced. She whipped her hair out of her eyes and observed, "Your balls are so hard, young man." I lowered my hands and raised her skirt. Then I planted my palms on her luxuriant ass, which was encased in smoky panty hose. I played with her shapely butt, swept a hand around front to wedge it between her thighs and feel the pocket of heat and moisture at her groin. Brazenly I stuck my thumbs under the waist band of her panty hose and peeled it down below her rump. I then placed my palms on her sweet cheeks and spread them. "Naughty naughty," she minced. My right middle finger slipped down the cleft between her buttocks, plowed up into her steamy cunt.
I laughed and said, "Your pussy is so wet, ma'am." That nasty finger of mine rimmed the cunt lips before sticking up inside her again. I stroked the slick walls. Beth moaned, bit down on her lower lip. The cunt fluttered around my finger.

It was her turn to tease. Impishly she whipped her nipples against mine. "Damn, that feels good," I snorted.
"Does it bother you that I'm forty-four?"
I grinned, showed her how my dick was trying to fuck her belly button. "What do you think?"
She craned her head and kissed my purple cockhead.
"You taste good," she said.
"Thanks, boss."
Beth thought what I said was funny, told me if I wanted to hold onto my job, I better damn well do what I was told.
"Yes, ma'am." I said.
"Your boss wants you to fuck her brains out."
"Yes, ma'am!"
"But first I'm gonna suck that cock of yours."
Beth swept away the crap on the salesman's desk and pushed me back onto it. My ass splayed on the cold desk top as my cock poled up. Her tongue was at the base of my shaft in no time, licking up my veined rod as if it were an all day sucker. My toes curled. My ass twitched. "Have I told you I like your cock?" she breathed.
"Yes boss." Her teeth closed in on my fat knob, and I gasped. My temples throbbing, I watched Beth's lips snap down my foreskin and snail along my fat shaft. I needed something to do, to keep my mind off this blow job I was getting, or I was gonna explode. So I peeled down more of her panty hose and ran a hand down her expansive stomach to the "v" of her closely trimmed bush. I placed two fingers on the vaginal slit, spread the labia. While I diddled the button hard clit, Beth vigorously blew me.

Beth flared her brown, wanton eyes at me, breathed through her nose. I thrust my arm up and buried two fingers in her squishy cunt. I stammered, "I-I want to eat your pussy." Beth wriggled her panty hose off, climbed on top of me and straddled my face between her thighs. We were now locked in a tight 69 position. Right above my nose was the best playground a guy could ask for. Immediately I stretched the pussy wide with my thumbs and jammed my tongue into the gaping pussy hole. Beth swayed her hips, poked her tongue at my ball sack. My tongue stroked along the roof of the pussy and Beth cried out. I raised my head, took a deep breath and repeatedly tongue porked the juicy quim. The woman's mouth snared my manhood, pleasured me with teeth, tongue and lips. My nuts distended with semen as an itchy heat invaded my scrotum, dick shaft and asshole. My tongue wandered to Beth’s puckered anus, rimmed the rosebud. I cried out. Damn, she was really putting her teeth into it now! She panted, "Do you want me?"
"I gotta have you now!"
Beth swung a leg over. But before I could make a move, she pinned me back down on the desk, this time with her legs straddling my hips.
"Boss lady on top," she reprimanded me.
"Yes, ma'am." Her heavy hanging tits brushed against my face. I took hold of the wonderful jugs, squeezed them together. The nipples popped into my hungry mouth.
"You like my tits, don't you?"
"Uh-huh," I mumbled.
"Let me know if you like this."
She pulled my tits from my face, pinched off her right nipple and ran it up my spittle shiny dick shaft, right along the big vein. A shock of pleasure racked my nuts. For an older babe, Beth sure knew some new tricks. Now she smothered my erection between her cleavage and tit fucked me.My toes curled. I cinched my ass and dick muscles. When my dickhead peaked out from between Beth's big tits, there was a droplet of pre-cum on it. The blonde giggled and said, "Looks like I have an employee who needs some immediate attention."
"Oh yeah, baby," I moaned.
She thrust her right leg out and spread her thighs. Beth's pussy yawned open. With a bitchy look on her face, she grabbed the base of my shaft and slapped my knob against her twat. "Still want to fuck this old pussy of mine?"
"Yeah!" I snarled.

Beth sat on my cock. My back arched. The cunt gripped me in its fluttering sex heat. "So tight..." I said.
"What did you expect?" she snapped. I grabbed her tits and squeezed. Beth rose and lowered her butt. A ring of feminine muscle stroked the length of my fat woody. I held on tight to the tits and bucked my hips to match her coital rhythms. "Fuck me--harder!" she demanded.
I banged my hips, spiking deep. Flesh slapped against flesh. We began to sweat. Beth's pussy quivered and flexed tighter. The itch in my balls flared out of control. I shrieked, "I'm gonna...!"
"Come for me, baby!" she cried. I fired one, two jets of cum inside her clenching cunt. "Yes!" Beth snarled. Her ass rose and lowered--fast. My rod was foamy with spent load. I grunted, managed a final spurt. Beth teetered forward and collapsed with her jugs mashed softly against my chest.
I ran my fingernails down her backbone, gently cupped her voluptuous buttocks. With my heart pounding in my ears, I thought about how this mid forties blonde was one of the best lays I'd ever had. I gathered my courage and told her. She kissed me, caught her breath and said, "Sucking up to the boss, eh?" I boomed a big laugh. Finally she conceded I did very good work, as she observed my spunk oozing out of her raw vagina. Perversely, she thrust her fingers up inside herself and licked them clean. Like I said, Beth was one of those bosses you wanted to work hard for.