Author's note: I know I said my last story would be it for 2014, but the response to the last installment of this series was so good, I figured how about a late Christmas present for my loyal readers and hopefully some new ones as well. So far the feedback from the first two Milf Tails has been very encouraging and I hope I don't let you down with this one. LC68
Man was bed going to feel good I thought as I gratefully cruised into my driveway. I'd pulled third shift at Wal-Mart last night, filling in for a last minute call out then after a quick stop home to shower and grab breakfast had rushed to make my nine am class. Today was one of only two days during the week I had classes all day and I'd thought about not taking the shift, but it was eight extra hours and the money would come in handy.
Besides it wasn't like I had anything better to do at night after Melissa had broken up with me a month ago. "I think we're better off being friends." I muttered, shutting the car off and gathering my books from the passenger seat. Turned out that was code for "I'd rather go out with John, he's on the football team!"
Not that I shouldn't have seen that coming, Melissa was stuck up and all about image, but she was hot as hell and.... Actually not all that wild in bed, more the 'I'm hot, I know it, so enjoy me' type. But she was that hot and worth being a little boring. Guess at the end of the day I'd been caught up in image as well, enjoying the other guys knowing I was with her.
On that note, even sitting there in the car and as tired as I was, my cock began to swell. Between work and school I hadn't had much time for a social life and hadn't gotten any since Miss Priss and just the thought of her had me getting worked up. My parents weren't home yet so it looked like my plan for the next couple of hours was stroking it to some porn and a nap.
"Living la vida loca, Tom." I muttered, getting out of the car.
My cell rang and glancing at it, I saw it was Steve, "Hey, man, what's going on, aren't you at work?"
"Hey Tom, yeah I'm on break, I need a favor."
"What's that?" I asked, walking up the driveway. I was so tired every step felt like an effort and I couldn't wait to hit the sack, well after some relief, that is.
"I got a chance to stay a couple of extra hours tonight."
"Cool, I picked up hours last night, we keep saving we can go on that trip to Florida this summer." I whistled into the phone, "Nude beaches, Steve!"
"Yeah, I know, but about that favor?"
"Oh, sorry, I was thinking about tanned tits." I laughed.
"Get laid, Tom." He laughed in return, "Tits are all you think about."
"You don't?"
"Well...yeah, but I have a pair I can play with."
"Thanks." I rolled my eyes, "That's some way to ask for a favor."
"Sorry," he said sounding anything but. "I have class tonight and planned on having time to go home and eat and grab my book. Can you swing by my house and grab my Anatomy book and the notebook on top of it and drop it off here?"
"Aw, come on, man! You should have called ten minutes ago I was right by your house, I just got home."
"So it'll only take a half hour to grab the book and drop it off."
"Can't your mom do it?" I asked, "I worked all night and had class all day, my eyes are burning."
"She's not answering; she might be out by the pool and doesn't take her phone outside with her, says that's her time to not be bothered."
I didn't answer right away, instead I pictured Steve's mom, Karen by the pool. Saying my best friend's mom was hot was like saying Bill Gates had a few bucks, the woman was smoking! Last time I slept over Steve's, I'd spent a good part of the afternoon lounging by the pool with my sunglasses on so Karen, and Steve for that matter, couldn't see me ogling her. She'd been wearing a two piece red bathing suit some girls my age wouldn't wear and looked just as good in it!
I'd known Steve for five years and lost track of how many times I'd spanked it to his mother. Every time I slept over his house it was inevitable. I'd wait until I was sure he was asleep and laying there on the spare bed, not five feet from him, I would blow a load to the thought of Karen blowing me.
"Hello? You there?" Steve asked.
"Yeah," I answered, stopping at my front door and adjusting the raging hard on in my shorts. Jeez I needed to get some. "I was..." I grinned, "Just thinking about your mom by the pool."
"Don't be an ass." Steve replied, "I get that enough from the other guys."
"Hey, that frat Jack belongs to voted her cougar of the year!"
"I know."
"Hey, I'm just goofing with you, Steve." I eased up sensing he was annoyed.
I didn't blame him, Steve had been enduring comments about his mother since his friends were old enough to know what sex was and although he usually laughed it off, it did get to him sometimes. I felt a quick pang of guilt. I was his best friend and he was right, I didn't need to bust him up about it.
"Yeah, I get it, but it gets old." He replied, "So anyway, I know it's a hassle, but can you grab my books? I don't need them for a couple of hours if you need to do other things."
I now felt like a jerk and responded quickly, "No worries I'll head over now that way I and drop them off and come home and pass out."
"Hey, thanks, Tom! You're a real friend, buddy!"
"Remember that and see if Cindy has any single friends." I told him.
"Will do!" he laughed and hung up.
Well, at least I could probably catch Karen by the pool and perv on her a little without Steve around. Yup, that was me, a real friend.
*****
I pulled in front of Steve's house and before I exited the car, paused to run my fingers through my dirty blond hair, fixing a few strays that were sticking up. Getting out, I took a minute to tuck in the sleeveless black t-shirt I'd changed into.
After a glance at my reflection in my side mirror, I rolled my eyes and pulled it out. The fact I'd changed into it at all was idiotic. I'd been hitting the gym and getting some sun and a couple of girls at school had made remarks I was looking pretty good.
For whatever reason I always tried to look good around Steve's mother, well at least since I'd noticed she was a hundred percent bona fide Milf as hot as any of the ones I watched on the porn sites. In fact it was my best friend's mom who had unwittingly got me into checking out milf and cougar porn in the first place. I'd sit there and watch those lucky young bastards getting taken for a ride by a hot woman twice their age and wonder if any of that stuff ever really happened.
I supposed it did, but not that much. Steve's mother was hot, but she had a professional job, was always a mom first before anything else and acted pretty reserved around me and his other friends. Then again, that damn bathing suit. She had to know it drove me wild.
As I made my way to along the front of his house it occurred to me I'd only seen her wear it when it was just me around. When there were a few of us either she never came out or wore a one piece bathing suit.
Not that she wasn't hot in that too; but it was nowhere near as revealing as the red one. Last time I saw her in that, she had bent over to pick something up and I thought her tits were going to fall out. Those tits were big enough to keep her floating in the pool on their own and went along with a nice well rounded ass and just enough hips to give her a hell of a figure. No, Karen wasn't a slender little thing like Melissa or most of the other girls, she was all woman.
Speaking of that woman, a grin spread across my face as I walked up to the gate that led into the backyard. I opened it quietly hoping that Karen would be lying out on her chair and I would get some time to check her out. Last time she had been lying on her stomach and her ass looked so fine I'd slipped into the house and whacked off right in the bathroom while staring at her well displayed ass cheeks.
I frowned when I looked around and saw she wasn't out there. Closing the gate I walked back across the front of the house and peeked into the garage. Her car was there and with a shrug I went and tried the front door. It was locked so I rang the bell. When no one answered I pulled out my phone and texted Steve
"Doors locked and I don't see your mom anywhere."
He replied within a couple of minutes
"She might e taking a nap, there's a key under the stupid gnome in the backyard for the side door, just be quiet."
I went back into the yard and grabbing the key from under the gnome let myself in.
"Mrs. Williams?" I called softly, "I'm here to grab Steve's books."