Milf For Hire

Author's Note: Welcome to my first story of 2014! I decided to kick off the year with a simple, but fun filled naughty little fantasy featuring a young man discovering a dirty little secret about his best friend's mom. So let's get the New Year rolling! LC

*

I opened my eyes and smiled, tonight was the night! After six weeks of saving every extra dollar I could, I was only twenty dollars short of the two hundred I needed and I was going to make that this morning! I lay there staring at the ceiling, my cock already stirring as I envisioned the night to come.

Glancing over at the other side of the room, I saw Jimmy was still asleep. He was lying on his side with his back to me and sliding my hand under the covers; I grabbed my now fully erect cock and started to stroke it. Closing my eyes, I thought of a pair long well shaped legs wrapped around me and imagined what those big tits would look like out of her sexy black lace bra. I could all but feel the wet heat of her mature pussy and just as good; the warm, wet and experienced mouth of an older woman who knew how to suck cock better than any girl my age.

I thought of that long blonde hair trailing down my stomach, fanned across my thighs. I had no idea what her face looked like, but pictured big blue eyes to go with that blond hair. Those eyes would be looking up at me while her lips were wrapped around my cock. My hand moved faster and I held back a moan; I was already close. My mind jumped to having her on her knees, grabbing those curvy hips and watching that well rounded ass while my cock slammed into it.

I would be fucking her as hard as I could and with no complaints because older women loved getting it hard and fast and could care less what you thought of them, they were just out for a good hard fucking. I'd whip my cock out and tell her to roll over and spray my hot cum in her mouth and all over her face. Unlike other girls I'd been with she wouldn't say no, because end of the day I would be paying good money for her to do anything I wanted and most likely a hot cougar like her would love...

"Oh!" a gasp escaped me as my cock exploded in my hand and I felt a warm sticky stream of cum splash onto my stomach.

I continued to pump, all the time imagining my load going into a pretty mouth and not all over myself. When I was finished, I lay there with my heart pounding while holding the sheet over my sticky stomach.

"Hey Nick, you awake?"

I quickly slipped my boxers up and dropped the sheet, wincing as it stuck to my stomach. Sitting up, I looked over to see Jimmy was now sitting on the side of the bed facing me. Shit, how long had he been awake?

"Yeah." I said simply.

"Good," Jimmy got up and after stretching, picked up a pair of sweat pants and slipped them over his boxers. Walking towards the window he said, "It's going to be a great day. Look at it out there." leaning on the windowsill he took a deep breath, "Clear skies, only in the seventies and it's a Saturday after a week of rain, we're going to get some calls today!" Facing me, he asked. "We got Mrs. Williams at eight and The Donovan's for nine thirty, but that's it right?"

"So far." I said. "But you're right, we'll get more."

"Well do me a favor, and check the e-mails and bump our ad, I want us on top of those other guys."

"Yeah, sure."

I started to slide my legs off the bed and could feel the sheet sticking to me. There was no way I could get up in front of him. After a minute he asked, "Well?"

"Oh, well I...I'm not wearing anything."

Jimmy scrunched his face up, "Come on man, why would you do that?"

"Habit." I shrugged, "Anyway, you want to turn around for a sec?"

"No problem, I don't want to wake my mother up laughing."

"Yeah, okay. More like you don't want her to come in here and see me naked, I'd end up being your step father."

"Asshole." He said, but laughed and started to turn around.

I slipped out of bed and was just reaching down to grab my jeans to toss on before I showered, when he turned back around.

"I knew it!" he exclaimed, pointing at my crotch where there was a large wet stain. "You were jerking off, you pig!"

"I..." oh, what the hell there was no denying it. "Hey, what can I say?"

"Dude that is nasty!" he waved his hand disgustedly at me, "Do that shit at home will you?"

"Oh, like you've never done it at my house?" I pulled my underwear down, causing him to turn his back to me. Slipping my jeans carefully over my cock, I zipped them up, "You've been sleeping over there once a week since we were in middle school."

"You're right, I did." He turned back and grinned at me, "But I had an excuse, I was thinking about your sister in the next room."

He laughed and I held back from saying anything. Jimmy had been busting my balls about my older sister Kelly for years. He had a thing for her, but had promised me as my best friend he would never ask her out, but that didn't stop him from busting my balls. I usually fell for it, but time gave it back to him.

"Maybe I was thinking about your mom."

"My mom?"

"She is pretty damn hot." I walked over to his desk and opened his lap top, "Best looking cougar I know."

"Don't be a jerk, my mother treats you like you're my brother."

"Maybe I'd rather her treat me like a cub; her little boy toy." I grinned as he frowned and tapped the side of my head as if thinking, "Maybe she lays there and thinks about me."

"Yeah I bet she does. All those sexy things like the time you threw up when we took you to six flags and, oh." he snapped his fingers, "The time she caught you peeing in our pool and especially that time she found a pair of her panties in that bed" he pointed to where I had just gotten up. "Pretty sure she knew I didn't take them."

I felt myself turning red, "I was fourteen and they were mixed in the sheets! I...I just was looking at them."

"Got eyes in your nose?" he asked.

We stood there staring at each other then after a moment we both burst out laughing.

"Okay," I waved my hand at him, "You got me, those were the only panties I'd seen that weren't my mother's or sisters."

"Could have at least brought a pair of your sister's over as a trade."

"Whatever, anyway I wasn't thinking about your mom." I grinned, "Got something hot going on tonight and, well you know, sometimes it gets to be too much"

"Wow, score!" he reached out and slapped my arm. "Anyone I know?"

"Nope." No one I knew either, at least not yet.

"Who is she?"

"I'd, uh, rather not say. It's sort of a hook up, nothing serious and I don't want to kiss and tell."

"Fine, be like that." He shrugged, "But speaking of my mom, roll up those sheets and I'll toss them in the wash, she don't need to be seeing your spooge."

"Fair enough" grabbing my underwear I tossed them in my gym bag and yanking the sheets from the bed, rolled them up in a ball.

Turning around I threw them at Jimmy who caught it and with a look of disgust made a show of holding the bundle at arm's length as if it were going to bite him.

"I'm going to run down and put these in the wash, bump the ad."

"You bet." I told him as he left the room and headed downstairs.

Sitting at the desk, I opened a browser and brought up Craig's list. Finding services I scrolled down until I found our ad for landscaping and after copying it, clicked new add, pasted it in and hit submit to put us back at the top of the list. We had done lawns last summer, but didn't make too much money. All we had was our cars and people would look at us funny when we would show up with lawnmowers and rakes sticking out of our trunks and backseats.

But this spring, Jimmy's father, who for the most part was pretty useless, had come up big and given Jimmy his old ford 250 pick up so he could make more money landscaping to help with school. So far it was only late July and we'd each saved over a thousand dollars. My parents took half to put in the bank for books and school expenses and after I paid for insurance and gas and had some fun I was still usually broke, but pretty content as there was nothing I really wanted.

That was until a few weeks ago. Figuring Jimmy would be a couple of minutes I clicked out of services and went over to adult services. As all the ads came up featuring young college age girls who were offering their services at hourly and half hour rates, I began to scroll through them, looking for the one that had caught my eye over a month ago and had since been obsessed with.

"Shit." I whispered when I didn't see it on the first page. "Please be around."

I hit the second page and halfway down sighed with relief at the words Milf for Hire! Clicking on the words I sat back and smiled at the picture that came up. It featured a woman from the neck down dressed in black lingerie that included stockings, lace panties and a transparent bra that showed not only her large round tits, but her nipples were visible. She was leaning against a doorway, with her hands under her tits, cupping them.

Although her face wasn't visible there was plenty of long blonde hair showing and I could not imagine that she wouldn't be as beautiful as her body. And that body! I would never say she was chubby, but she had a full set of hips and her thighs looked soft and inviting. Her ass looked to have some curve to it and overall her body was a sharp contrast to the slender girls I went to school with.

Most of them had smaller perky tits and tight little asses. Not that I was complaining, I'd had some serious fun with the couple of girls I'd been with at PC, but the woman in the ad's body seemed so...I kept coming back to the word inviting. The fact that it belonged to a woman who according to her ad was over twice my age was one hell of a turn on. Pulling my eyes from the picture, I read the ad that by now I was sure I could quote by heart.

"Are you tired of those skinny inexperienced little things in those other ads? Well if you are, then I'm the woman for you. That's right, woman, not a girl. This forty two year old Milf is sexy, fun and most of all experienced!

"All those young girls are doing is going through the motions, trying to get you off and out the door for the next one. But this hot cougar is out for more than just the money, honey! When you're with me you're not only enjoying me, but I am enjoying you just as much because this slutty little blonde loves to get a good hard fucking as much as you love to give one!"

"So whether you're a gentleman my age looking for a fun time or a young man who wants to know what it's like to be with a real woman, two hundred dollars will get you all that you want and more!"

I went back to the picture and for the hundredth time wondered what had me so interested. I had never been into Milf or cougar porn before. Truth be told, the only woman in her forties I considered hot was Jimmy's mom, Wendy. I wasn't alone in that. Poor Jimmy had been getting his balls busted about his mother for years.

I grinned at the thought that the panties they had caught me with weren't the only pair I'd gotten. I'd smuggled a black pair out of his house once and had jacked off with them several times while thinking about my best friend's mother. I still thought she was hot, but no longer used her inspiration.

Once I'd started dating it had gotten me over thinking of Wendy along with the fact that when I'd gotten a little older I realized this was my best friend's mother and she had been very good to me. Wendy even kept it from my parents about her finding me with her panties. I recalled when she found them and I tried to stutter out an apology she simply said, "Boys will be boys and there's worse things than a cute boy thinking I'm sexy, but let's not let it happen again, or I'll have to tell your folks." She'd never mentioned it again, but it had taken a month before I could look at her without blushing.

But other than her, no older woman had done it for me and even Wendy was mostly because she was the first woman I knew who I thought was sexy. So I found it odd this ad grabbed me the way it had. I'd only found it by accident when Jimmy and I were working on our first Craig's list ad and for fun he had decided to click on the adult services. While he was joking about which ones he would pick or wondering if any of them were fellow PC students he had spotted this one and clicked on it.

Jimmy had laughed and said, "Man, imagine fucking someone your mom's age?" then after a moment had added, "Bet a woman that old gives a hell of a blow job." He had clicked off of it, but the ad stuck in my mind and later that night I'd looked at it again. After that I'd gone online and watched some milf porn, which I'd formally had no interest in and became hooked.

Now it was all I thought about, how much better an older lover could be. The girls I had been with were fun, but fun for my age, which is what they were. They were still a little shy and hung up on some things, a woman that age? She would know exactly what she wanted, how to get it and would be damn good at it. But even though I was watching movies my thoughts kept turning back to that add, the fact there was a woman that age available that would do whatever I wanted was killing me.

Finally after three weeks of jerking off, including several times while staring at the picture in the ad it occurred to me why not do it? I could save up the money and it's not like anyone would know. I'm sure it was something my parents would frown on, and I wouldn't tell any friends, especially Jimmy because I would never hear the end of it.

Once I'd decided to chase my fantasy I'd looked at the ad every day hoping that whoever she was she would keep doing this. Right now all my bills were paid including the money to my parents to go in the bank. I had a hundred and sixty stashed and after the couple of jobs today would have two. Staring at the ad I wondered if I should contact her now. No, I had to get to work and...

"What are you doing, looking at hookers again?" I jumped as Jimmy came up behind me. "Shit, all the hotties we saw and you're looking at the old lady?"

"Like you wouldn't tap that." I responded, pointing at her.

"I wouldn't pay for it." Slapping me on the shoulder he laughed, "Hey, Nick you want to bang a cougar, Miss Jennings is single!"

"Ugh." I gave a mock shudder, "Dude, she has false teeth."

"Then she can take them out and give you a gum job!"

I shut the computer off and got up to see Jimmy tossing a t-shirt on. "You about ready to go?"

"I have to shower."

"Why, we're going to get all sweaty." He reminded me, "But really, you know if you want some desperate housewife go hit the bar over on Broadway lot of lonely ladies there."

"How do you know?"

"Oh, well..." he looked away.

"No! You fucking dog!" I exclaimed "Have you really...?"

"I'm not proud." He made a show of hanging his head, "But she was lonely and upset and I took one for the team and made her..."

"How old was she?" I asked.

"I don't know, maybe thirty," he grinned wickedly, "Old enough to know some tricks."

"You never told me."

"It's none of your..."

We looked up at the sound of heels coming down the hallway.

"What's your mom doing up before nine on a Saturday?"

"I have no..."

He stopped at a knock on the door and Wendy calling, "Hey you guys decent?"

"Yeah," Jimmy called back as I reached down and grabbed a Red Sox shirt from my bag and started to put it on.

"I should say as decent as a two twenty year old boys can be anyway." Wendy laughed as she entered the room.

"Morning, Wendy, I..." I stopped in mid sentence when I saw her.

Wendy was wearing a black skirt so short I doubted she could bend over in it and a pink short sleeved blouse that wouldn't be anything special if the buttons were secured. Instead the top half was wide open exposing a red shirt beneath it that was low cut to where I could not just see the top half of her tits, but a red lace bra.

Her long blonde hair was down despite how hot it was outside and I noticed she was wearing eye shadow to accentuate her blue eyes and her lips were painted a deep red. Catching myself staring at her chest, I dropped my eyes down and was now confronted with her almost totally exposed legs. Wendy sun bathed by the pool every day and her legs were not only long and well shaped, but as tan as I was from working outside all summer.

Her legs were made to look even better by a pair of what had to be four inch black heels. Unable to help it, my eyes worked the length of her legs right up to the hem of the skirt which I swore couldn't be more than a couple of inches lower than her crotch. If she sat across from anyone today they would be getting a show.

She was standing with her legs slightly apart and I couldn't help staring at the inside of her thighs. Like the woman I was hoping to meet tonight her thighs weren't slender, but still had a nice shape, thick some of the guys at school would call them.

"Mom!" Jimmy spoke up, "What the hell are you wearing?"

"I'm going to work."

"Like that?" he pointed, "Can you sit in that thing?"

"I'm working at the lounge today." She shrugged, "I won't get tips in jeans."

"The lounge is open this early?"

"I..." she paused then smiled, "No, but I'm seeing George for breakfast first and figured I'd give him something to think about."

"Him and everyone else." Jimmy shook his head, "That's way too short of a skirt, mom."

"I'll keep that in mind

dad"

she said with more than a little annoyance in her voice.

"Yeah, okay." Jimmy sighed.

"Anyway, I came in here to tell you I'll be home for a little bit later, but I'll probably be gone for the night before you get back. There's left over pork chops and mashed potatoes in the fridge."

"Where you going," he looked annoyed, "George's again?"

"Yes," she told him, "Why, do I need permission?"

"No, just wondering why he never stays over here."

"Maybe he's afraid of my guard dog son." She reached out and touched his cheek, "I love that you look out for me Jimmy, but I'm a grown woman and I feel more comfortable at his place. I don't have to look around his house and be reminded of your asshole father. I'll be home for breakfast okay?"

"Sure." Wendy kissed him on the cheek and as she turned away gave me a little wave. "You boys go out and make some money today!"

"Maybe I should wear a short skirt." I laughed and ignoring Jimmy's dirty look went on, "Maybe I would get better tips."

"Nah, you don't have the legs for a skirt." She told me, then surprised me by adding, "But you do look good with your shirt off, bet some of the horny housewives would tip you extra then."

"Mom." Jimmy sounded aggravated.

"Oh, honey." She laughed, as she turned away from us "It was just a joke."

She left the room and I saw Jimmy still looked pissed. "Everything okay? I was only joking about the skirt."

"I'm not mad at you. Mom's been acting weird. She comes and goes all the time and she's dressing like...well you saw her."

"Yeah, but she's a cocktail waitress right?"

"Yeah that was all she could find when her office closed, but she works messed up hours. She'll be gone three four hours, come home, go back out later, she says she splits shifts."

"I take it you don't like the boyfriend?"

"I might if I ever met him."

"You never met George?"

"Nope, not yet, and I don't know why. I mean he's banging her every Saturday night and some Friday's too, so I guess it's serious, but she won't bring him around."

"Maybe she thinks you'll give him a hard time."

"Whatever."

"Hey, Jimmy, she's single and she is pretty damn hot. Good for her."

He stared at me, then smirked, "Your sister is single and pretty hot too, maybe..."

He stopped when his cell started ringing and picking it up off the desk he answered, "Hi, yes this Jimmy." He gave me a thumbs up, "Sure Miss Clancy, we can get there today, how's eleven? Great, we'll be there."