Author's note: Welcome to the second installment of my Milf Tails series. Thank you to all who voted on the first one (grateful Milf). I received some feedback saying the story was good "for what it was" but not up to my usual standard. First off, thank you for that feedback, I appreciate all comments I receive. As for the story being 'not up to par' I take that as a compliment, but would like to explain something. No one wants to eat the same food every day and by that token writing the same style all the time can be boring, especially when some of my work is intense and takes its toll. These stories are me 'letting my hair down" and saying. "Hey, let's have some fun and write some porn!" Hopefully you will come to enjoy that style and I hope to gain some new readers through it. But for my "regulars" never fear, there are plenty of stories like SWB and Damn Red Dress floating around in my head. Now, on to some hot cougar/cub action LC.
*****
"Hey, Cory, you almost done?" Mom yelled from down the hall.
"Yeah!" I called out, "I just have to get my lap top together!"
"Okay, but try to hurry, Savannah will be here soon and she's had a long flight and might want to rest."
"Well, God forbid, she waits another ten minutes." I muttered as I got down on my knees and untangled all the wires from the various devices on my desk.
"Don't be a jerk, Cory." Mom startled me from my doorway. "It won't kill you to sleep downstairs for a couple of weeks."
Looking over my shoulder, I saw mom leaning against the door and said, "I don't know why she has to come up here. We have a guest room."
"Guest room?" Mom laughed. "It's your father's old den that he stuck a bed in when I got sick of him coming home drunk. It's not a real bedroom."
Standing, I closed my lap top and put my speakers and other odds and ends on top of it. "So a woman you haven't seen in years get's my room and I get the crappy room?"
Mom rolled her eyes and gave her long blonde hair a toss. "Cory, Savannah has been my best friend since middle school. I haven't seen her because she made the mistake of following her asshole husband out to Texas." She sighed, "Least I was smart enough to pick a local asshole. Anyway just because she isn't here doesn't mean she's not still my best friend."
"Yeah, well I still don't know why..."
"Because it's the right thing to do!" Mom snapped. "My best friend just got divorced because her husband was cheating on her with everything that moves. She has nothing out there and is coming back home. She's already found a place, but it's a new building and it won't be ready for three weeks and in the meantime she's staying here in this room, understood?"
"I don't care she stays," I began.
"Well that's nice of you." Mom said as she walked over to me, "And she will stay in this room because its nicer and because my room is right down the hall and I know she is going to be upset at night and want to talk. Besides up here is the full bathroom and she may want to soak in the tub at night; you can use the shower downstairs."
"Fine." I nodded.
"Look, Cory," Mom put her arm around me. "She's having it rough and this is a good thing I'm doing for her. She's helped me plenty in the past and it's my turn. You're doing a good thing too by giving up your room for a little while." She gave my shoulder a squeeze, "Besides what have I always told you about doing a good deed?"
"That doing one will usually get you one." I told her.
"Right, it's karma. Do something nice, get something nice in return. And I raised you to be good to people Cory, you're a nice young man, not a tool like your dad."
"I'm not him." I shook my head.
"Not at all, but he would be selfish over something dumb like this; and I don't want you to be, okay?"
"Okay." I sighed, "But I don't have to like it."
"Good enough," Mom laughed and sliding her hand up rifled her fingers through my short black hair.
"Come on, mom!" I pulled my head back, "I just brushed it."
"And you'll brush it ten more times today, my pretty boy." She said, "And I bet I'm the only woman who would get yelled at for messing your hair up."
I felt myself blushing and she laughed, "You're adorable. Nineteen and even a hint of me talking about what you do with girls gets you embarrassed."
"Well, you know." I shrugged.
"I know, I'm a single woman remember?" she winked. "I'm sure you do just fine and as long as you're good to them and careful I don't mind what you do." She touched my cheek. "You're a good looking guy Cory, got your dad's hair and those killer green eyes." She shrugged, "He was an asshole, but a good looking one. You'll be a good looking sweet guy and make a girl very happy."
"Um, sure." I said evasively.
Not that I would want to talk to my mother about sex under any circumstances, but what made me more uncomfortable was the fact she seemed to think I was getting it a lot more than I was.
That was what my jerk of a father thought as well. Whenever I saw him he would make cracks about how I must be 'nailing' all those college hotties and having a blast for myself.
It was easier to just smile and give him a wink and say I did okay, than tell him the truth; that I'd only been with two girls. The first was Donna who I met in middle school and dated through high school.
We were together all four years and she was the only girl I'd slept with. But she got a great offer to go to USC and I wanted to go to college locally so I wouldn't be leaving my mother alone with all the bills.
The second girl I'd messed around with was Tara a few months ago and it hadn't gone well. She was two years older and brought me back to her dorm room after a party. I was used to Donna and so nervous I couldn't get it up. Tara decided to help me along by going down on me and I came in her mouth in seconds. She didn't seem too happy, but I made up for it by returning the favor.
I'd always enjoyed that with Donna and must have done a good job as Tara got off pretty hard. But when it came to sex, she again had to coax me with her mouth and I'd barely lasted a dozen pumps before going off. We lay there for awhile in awkward silence, then she decided to get me going again and it was just as quick. She didn't ask me to stay the night and I gratefully slunk out of her room.
That was the last time and although I got more than few offers from girls who wanted to date, as well as those looking for just sex, I was now gun shy and afraid of embarrassing myself. Fortunately Tara hadn't gone around saying anything, but who knew if someone else would?
Mom's cell phone rang and stepping away from me he answered, "Hey, are you almost here?"
Turning from her, I slipped my lap top, mouse and other stuff into my book bag and grabbing the small suitcase I had tossed a few days worth of clothes in, walked past mom and headed downstairs.
As I carried my bags down the carpeted stairs and headed into the small room that would serve as my home within my home for the next few weeks, my mind continued on its path of my currently nonexistent sex life.
I'd had a couple of chances as parties. Just like Tara, a couple of point blank, hey, let's have some fun offers. They were hot and into me and I'm sure would have been a great time, but my first thought was not, "hell yeah" it was, "what if?". I now had it in my head I might not be able to and was turning down sex when I should be enjoying it.
Tossing my bag on the narrow single bed and frowning in distaste at the faint cigar smell that resisted everything mom had tried in the room since dad left, I put my lap top down on the table. Right now that lap top and the porn sites bookmarked on it were my sex life. It was pretty hard to let down your hand.
Even my fantasies were becoming sexy thoughts of what I would do to certain girls if given the chance turning into wondering could I? I was good looking, surrounded by pretty girls and horny all the time, yet afraid to try anything for fear of failure.
Just as frustrating was I had no one to discuss it with. Mom was good about talking to me about pretty much anything, but telling ones mother they went off to quick and had a hard time getting it up was not an option. My father was a macho prick who would be mortified his son was not the stud he obviously thought he was and I didn't trust any of my friends not to either bust my balls, or worse, tell someone.
I'd gotten to the point I'd gone onto a porn site that had an advice column and posted my question. I received several responses including hiring a prostitute. The explanation was they were paid to make me happy and I could relax and not give a shit what they thought.
The second answer was a sexual surrogate and one person had posted they were a lonely mid forties housewife and if I was ever in the New York area to look her up and she would be happy to patiently teach me to relax.
That had started a slew of responses about how an older woman would be the key. They had experience, knew what they wanted, weren't afraid to tell you what they wanted and guys their age couldn't keep up.
They would be more than happy to show me how to please a woman was the general consensus. For me that was no help. I knew milf and cougar porn was big on the net, but I had never gotten into it. Maybe because I'd never met a woman my mother's age that was all that hot.
Not that my mother wasn't attractive for her age and a couple of her friends weren't bad, but as for what Milf's were shown looking like on the net? I could honestly say none of my friend's mother's would look too good parading around in miniskirts and fuck me shoes.
Then again, I never looked beyond my friend's moms. Maybe at the clubs there might be...I made a disgusted noise as I pulled my clothes out and began putting them in the old scratched up bureau dad had left behind.
It was getting pretty bad when I was beginning to think about going out and trying to find a desperate housewife to show me what to do. Besides, my lack of confidence even intruded there. If these women were that experienced and knew what they wanted they sure as well would want more than a nervous kid who couldn't last more than thirty seconds.
I jumped when the doorbell rang and heard mom running down the stairs.
"Cory, Savannah's here!"
"Wonderful." I turned in time to see mom all but fly past the doorway and had to smile, it was good to see her so excited, since dad had left she'd had a lot of ups and downs.
I walked out into the living room to see mom had thrown the door open and was hugging someone tightly. As I approached all I could see was a pair of black clad arms around mom's back and some long reddish brown hair.
