tagMatureMilf Tails: The Benefits Package

Milf Tails: The Benefits Package

bylovecraft68©

Author's Note: Welcome to the latest installment of my Milf Tails series. I am happy to say these stories are being received much better than I expected, so thank you to all who have commented and voted. During these stories I've tried my hand at putting my spin on some common fantasies and for this one...what young man hasn't fantasized about his hot older boss? Enjoy. LC68

At the sound of footsteps I looked up from the paperclip I'd been nervously twisting while waiting for Mrs. Sanders to come back into the conference room. She had ended the weekly production meeting fifteen minutes ago, but asked me to stay behind and wait for her while she returned a couple of phone calls she had missed during the hour long meeting.

That wasn't what had me nervous. Every week when the meeting ended she would ask the interns to stay behind and quiz us then dole out our tedious assignments for the week and tell us she would see us again on the intern only meeting next Thursday.

This week, however, she had dismissed the other interns, including her son, my longtime best friend Steven, and told me to hang back. That had earned me several concerned looks from the other interns and Steven as well. The summer was almost at an end and the company could only keep three of the five of us. Once they left I'd sat and fidgeted, hoping to hell the axe was not going to fall.

The door opening and closing behind me signaled that moment might be coming soon and I took a deep breath when I saw Mrs. Sanders come around from behind me. That deep breath brought with it the scent of her perfume which although I had no clue what brand it was, knew I loved it and it made it hard to concentrate when she was close to me.

Well it was one of many things that had that effect on me, I thought as she came into my view. Not only was Selena Sanders my best friend's mom and current employer, but was far and away the hottest woman I'd ever met. For a mother of a son my age, she looked as good if not better than women half her age.

Like many natural redheads, her skin was fair to the point I had once said she looked pale and was firmly told that when describing a woman the term was fair unless I liked being single. That fair skin was a sexy compliment to her long lustrous bright red hair and deep blue eyes that were always focused in an intense stare and never seemed to miss anything, including I am sure, catching me checking her out more than once.

As beautiful as those eyes were they were the second most attractive feature on her face behind a pair of full luscious looking lips that looked tailor made to be wrapped around a cock. Best friend's mother or not, those lips had been a permanent fixture around my cock in my dreams since I'd been old enough to know what a blow job was.

"Austin?"

I blinked and saw Mrs. Sanders was sitting on the edge of the table next to me.

"I called your name twice."

"S...sorry Mrs. Sanders. I was um...thinking."

"Oh?" She raised her eyebrows, "About what?"

"Well the, uh, those quarterly numbers. They seemed kind of..."

"That's what you were thinking about?" she sighed, "How disappointing."

"Disappointing?" I repeated.

"Very." She slipped her black blazer off, "I was hoping you were thinking of something more creative."

I didn't answer right away as my focus was on her chest. Beneath the blazer was a tight lacy sleeveless shirt that looked as if her impressive tits were going to burst out from. The shirt was low enough to show off the top halves of her well rounded milky white breasts and left some of her lower stomach bare.

"Not very creative at all today are you?"

"Well, um, I'm not sure what you want me to tell you Mrs..."

"Selena." She said, tilting her head and giving me a rare smile, "No one else is here and I've known you since you were a kid, so how about Selena?"

"Okay." I nodded trying to keep my eyes on her face.

"That's right we know each other very well." She pulled the clip from her hair and giving her head a shake sent her long hair cascading down her shoulders. "I'm very comfortable with you."

"You are?" I asked staring as she slid along the table until she was sitting on the edge less than a foot away from me.

"Very. You know me outside of here so I don't feel like I always have to put on an act with you." She touched her hair and laughed, "I can let my hair down."

Lifting her leg she slipped her red heel off and I was vaguely aware of the sound of it hitting the floor. My attention was more on the way her skirt had slid up her thigh when she bent her leg. Not only was I getting a view of most of her leg, but was able to see her black stockings were thigh highs. The black on her creamy skin looked damn hot and a trickle of sweat made its way down my back.

Placing her foot on the table, she lifted her other leg and this time playfully kicked the shoe off. To my astonishment she spun on the table until she was now in front of me. She put her feet on the arms of my chair and I was unable to help looking between her open legs. Between the exposed flesh of her thighs was a black lace thong and as I tried to convince myself to look away she said,

"In fact I would love to be even more comfortable with you, very comfortable." She was speaking softly and finally managing to get my eyes off her crotch I looked down at her foot where I could make out her red painted toes through the sheer black material.

"See why I was disappointed in hearing you were thinking about work was I thought you were thinking about these."

Grabbing the bottom of her shirt, Selena peeled it up over her head and tossing it to the side cupped her large breasts that were now encased only in a transparent black lace bra.

"Holy shit." I whispered.

"You do think about them don't you, Austin?"

The bra clasped in the middle and as I watched with my cock thickening between my legs, she placed her fingers on the small silver clasp.

"You want to see your best friend's mom's tits?"

"Mrs...I mean Selena..." I swallowed hard, and then said in a barely audible voice, "Yes."

"Good, because I want to show them to you."

With a practiced movement of her fingers the bra fell away and my jaw fell with it. Selena's tits were by far the biggest I'd ever seen in person. Far bigger than the tits of any girl I'd fooled around with. Her nipples were light pink and pointing straight at me. Cupping them, she lifted them and teasing her nipples with her red nails asked, "You think a lot about these?"

"Oh yeah." I nodded, my head bobbing like an idiot.

"Yeah? Thought about my tits? What about my pussy?"

"I..."

"Bet you thought about my mouth haven't you, Austin."

"Um, I..."

My words turned into a gasp when pushing her legs out, Selena sent my chair rolling back a couple of feet. She slid off the table and onto her knees between my legs. Looking up at me, she grabbed my pants and ripped them open, sending the button flying.

"I thought about it." She breathed pulling my zipper down. "I've thought about wrapping my lips around this big hard," she licked her lips, "Young cock!"

She reached into my underwear and I moaned when her fingers wrapped around my throbbing cock and pulled it out.

"Hmm, is this all for Steven's mom?" she smiled, "You want your best friend's mom to suck you off? You want to cum in my mouth?"

"Yes, please." I moaned as she started jerking me off.

"Then ask." Her blue eyes, bright with lust, were staring into mine, "Be a man and tell me what you want!"

"I...Selena I want you to suck my cock." I said as firmly as I could manage.

"That makes two of us," still looking me in the eye she wagged her tongue provocatively at me then opening her mouth took my cock between her lips and...

"Austin!"

I jumped at the feeling of something striking my side. I opened my eyes to see Mrs. Sanders standing at the wall in front of the opposite end of the conference table. She was facing a projection screen that featured a graph and pointing to the numbers while speaking.

I looked around quickly at the two dozen people sitting around the large table and let out a sigh of relief that everyone was looking at her and hadn't noticed I had dozed off.

"Thanks man." I nodded over to Steve who, as always, was sitting next to me.

Shaking his head, he leaned over and whispered, "Look sharp, buddy. This conference trip is a big part of my mother deciding who stays."

"I know." I shifted in my seat and winced when my hard cock bent awkwardly.

Steven started to speak, then quickly turned back towards where his mother was now standing in front of the table, talking about why she felt this quarter's sales were down and asking what could be done about it.

With him no longer looking at me, I reached into my lap and shoved my still semi hard cock into a more comfortable position. I sat back in the leather chair and rubbed at my stinging eyes. The last twenty four hours had been a whirlwind during which I had barely slept.

Yesterday at five Mrs. Sander's had decided last minute she was going to take her interns to the conference in Chicago with her and we needed to be at the airport in two hours. I'd hurriedly thrown a bag together and when Steven picked me up he had told me his mother knew about this all along and was playing her "how bad do they want it" game.

On the plane ride she had sat between me and Mandy, who I was sure was a lock to get one of the three available positions the five of us were fighting for. The flight was four hours of trying to listen to everything she was telling us about the conference, reading the reports she had dumped in our lap and toughest of all, trying to keep from being caught gawking at her.

We were in the middle of a heat wave and Mrs. Sanders had worn a pair of black shorts that showed her long legs and a white shirt with a plunging neckline. Between her exposed thighs and the amount of cleavage she had on display it was a battle to keep my eyes straight ahead and I swore she caught me looking a couple of times.

When we got to the hotel Steven and I had sat up in our room until after midnight quizzing each other on the reports. He had gone to sleep, but I was nervous as hell. I wanted this job badly and was pretty sure Mandy was in and, as much as she treated him like anyone else, I had a feeling the bosses son was a shoe in for the second spot. That left me competing with Melissa and Allison for the last position and both girls were taking things as seriously as I was.

I'd finally shut off my laptop at three am and we had to be up at six. We'd been in meetings since eight am moving from room to room and making things worse was the air conditioner in this one was broken and the heat, along with the dull material had caused me to doze off. Speaking of the heat, I tugged the knot in my tie, loosening it slightly. I was sweating beneath my shirt and that dream had only made me warmer.

My eyes fell on the subject of that dream who was now once again facing the TV. Mrs. Sanders generally dressed professionally, but was not the stereotyped bitch in control who looked like she wouldn't know what a good time was or downplay her looks.

The skirt she was wearing was a perfect example of that. Although certainly not a mini, it was several inches over her knees and tight enough to show off her ass. Her well shaped legs were encased in the sheer black stockings featured in my dreams and accentuated by her heels which were high enough to be bordering on stilettos.

Far higher than any I had seen her wear before. In spite of the heat her long red hair was down and I was sure her 'business sexy' attire as she had referred to it in the past was a direct result of almost everyone in the room being male.

In one of our meetings Mrs. Sanders had addressed the girls telling them to never dress in a slutty or blatantly provocative manner, but there was nothing wrong with tastefully showing off what you had and being a distraction, especially if negotiating a contract. Distracting was what Mrs. Sanders had been ever since the day I had gone over Steven's house after school and saw her for the first time.

She had been on her knees in the garden and my eyes were immediately glued to her amazing ass in her tight shorts. When she had stood up and turned around I'd been blow away at how beautiful she was never mind the body that went with it.

Over the years my fantasies had ranged from the silly ones of a young teenager where I imagined her telling me how much she liked me and wanting to be my girlfriend. A couple of years later, once I'd discovered what sex really was and knew exactly what I was looking at, those harmless fantasies had turned into hardcore sex scenes.

At times I felt bad about it. Mrs. Sanders had always been damn good to me and treated me as if I were her own. But other times all I knew was she had a damn fine body, blow job lips and I would love to know what it would be like to fuck her.

Even when I started dating and having sex, she was my default fantasy. In my dreams as well as waking thoughts Mrs. Sanders had done every dirty act imaginable to me and loved every minute of it. Over the years she had cavorted through my fantasies in everything from a naughty school girl outfit to a variety of lingerie to greeting me in her office butt ass naked on her desk.

Apparently my desire for her was deeper than I thought. Two months ago when I had broken up with my latest girl friend Jen, Steven had commented that maybe I should try a different type. When I asked what he meant he'd said, "Austin, go for a blonde or a brunette that was the third redhead in a row that didn't work out." He'd then shrugged, "Unless you got some kind of fetish or something."

I'd gotten nervous when he'd said that wondering if he equated the fact that his mother was a stunning redhead. After all it wasn't like he was oblivious to the fact I thought his mother was hot as here and there he would laugh and tell me,

"Keep your eyes in your head, man, that's my mom." He said it good naturedly, because I was, as he always said, like a brother to him. That made me feel like shit, but never enough that his hot mom would not still be a frequent guest in my fantasies.

Lately it had been worse than ever. In the past I would only see her if I slept over Steven's or quickly if I was picking him up to go somewhere. Now at twenty two the two of us didn't do the sleep over thing too often and I missed them. Mrs. Sanders would usually walk around in some pretty tight shorts and tops and on occasions she would wander out at night or early in the morning wearing a short, sexy little black robe.

I used to think Steven's father was the luckiest guy in the world to be in bed with that every night, but it seemed he didn't think so. A year ago Steven told me his mother had caught his dad cheating and threatened to cut his cock off if he ever came within a hundred feet of her again.

What he thought he was getting she couldn't give I have no idea, except that Steven overheard his mother telling his aunt that it wasn't one woman, but that his father had been hiring escorts, young ones, barely eighteen from what he'd heard.

I thought it ironic that he would look for young girls while I was that age and would give anything to be with a woman who was twice my age. Once she was single and according to Steven hardly dated, my dirty thoughts were gaining more of a hold on me as I pictured her being lonely and horny, longing for someone to appreciate and take care of her fine body.

Things got worse when she hired me along with Steven as interns in her investment firm. I was now seeing her every day dressing in her sexy business woman attire and my mind was in overdrive. I was interning with three cute girls my age and had barely given any of them a glance.

They were pretty, but they were girls. Mrs. Sanders was a woman and one hell of a woman. At this point if I had a dollar for every dream or thought I'd had of her hiking her skirt up for me to fuck her over her desk, I would...

I jumped at the sound of a knock on the door. I turned in my seat to see Mr. Jenkins, the VP of sales pop his head in. "Selena can I steal you for a moment? They have an issue at the home office and need to speak with you."

"Of course." She nodded and placing her pointer on the table announced, "I'll be right back, please take this time to study the spreadsheet I e-mailed all of you and see where you feel we should concentrate our efforts next quarter."

She walked along the table and as she passed me I did the best could to follow her with my eyes as long as I could without turning my head. As she'd asked, I stared at the spreadsheet on my laptop in front of me, but heard most of the people around me start talking amongst themselves. I'd been staring at this thing since last night, but leaning forward, rubbed at my tired eyes and tried to focus.

"Hey, you better snap out of it." Steven said quietly.

"Trying to, but man I'm beat."

"Well when we get back to the room you better take a quick nap, a hot shower and grab a red bull" he slapped my leg under the table, "Because we're going to have some fun tonight!"

I looked around before speaking again, "Steven, you sure this isn't one of your mom's weird tests? You know, see who goes out and who works?"

"No," he shook his head, "She talked to me about it and it's legit. She said all of us worked hard all summer and she was giving us tonight to go out on the town as a reward. So stop worrying."

"I have to." I told him. "I'm not sure I'm sticking around."

"You will be." He sighed, "Forget about it for one night man, we're going to have some fun!"

I nodded, but wasn't so sure about it. Mandy had been to Chicago several times to visit family and last night had been talking about a great club she had gone to. Mrs.' Sanders had overheard her and then gotten us all together to announce that she thought it would be an opportunity to go out and relax.

She said the only restriction she would put on us was we were to take a taxi and not a rental car and she wanted everyone coming back to the hotel, not hooking up with someone and ending up who knows where.

Steven was thrilled because he and Melissa, a cute little brunette, who was currently looking his way doing had been flirting ever since she broke up with her boyfriend and he figured tonight they would break the ice at the club. He had also hinted a couple of times about me maybe giving him a couple of hours in our room if things went really well.

"You got that look on your puss." Steven cut into my thoughts and rolled his eyes, "Now what?"

"I'm tired and I'm stressed." I said softly, "You and Melissa are going to have a good time."

"You can too."

"Mandy has a fiancé and Allison has a girlfriend."

"Yeah she does and she is hot! You see her picture?"

"I did and she is." I agreed, "But that means we're just kind of..."

"There will be a club full of people and you're single!" he pointed out. "You'll find someone to dance with and have a couple of drinks." He winked, "I'm sure Chicago has redheads."

"Whatever, I might just hang back and rest."

"Twenty two, out of town with a chance to have some real fun and you're going to rest?" he frowned, "Man, even my mom says work hard play hard."

I avoided thinking about what Steven's mother did when she played hard, that is if she did. Steven had told me he had gotten to the point he was trying to get her to get out and meet someone and have some fun.

"Come on, Austin," he continued, "You..."

He stopped when the door opened and Mrs. Sanders came back in. She had an annoyed look on her face and didn't say anything until she had reached the head of the table where she addressed everyone.

"I'm sorry, ladies and gentlemen, but I have to cut this meeting a little short. It seems I have to work on something for home office that they need right away. So I guess the good news is you're all off the hook half hour early. You may all leave now."

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