Milf Tails: Back in the Saddle

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.

"So good to see you!" Mom exclaimed as she released our guest and stepped back from her, "Come on in!"

As mom moved to the side, Savannah stepped into the room. My first thought was she was vastly over dressed. She was wearing a long black dress coat that went down to her knees and was tied at the waist. What I could see of her from the neck up however, did catch my attention. Savannah's auburn hair was curly and one side of it was down across her shoulder and was so long it trailed down past her where I imagined her breasts would be inside the overcoat.

Her skin had an olive tint to it and I recalled mom had mentioned she was originally from Brazil. Her huge dark eyes were peering out from the longest lashes I'd seen and she was flashing a huge smile that in addition to her perfect teeth caused me to notice her full lips, the type women went and paid for injections to have.

"Why hello my friend!" she replied. "It's been to long!" giving mom a quick up and down look, she nodded approvingly, "You haven't changed at all, Carol. Bet your friends are all jealous of you, just like high school."

Savannah's voice was soft and smoky, with just a hint of an accent and the sound of it caught my attention immediately. It was the voice some of the women on the web cams used and could probably make saying, 'what's for dinner' Sound sexy.

"I don't know about that!" Mom laughed, "But it sounds good." Looking at her best friend she frowned, "What's with that jacket? It's over seventy five degrees!"

"I wasn't sure." She shrugged, "I've been in Texas for twenty years and all I remember about Rhode Island was that it could be eighty or eighteen. Besides, I was out of room in my bags so figured I would just wear this."

"Well, take it off before you sweat and catch a cold." Mom told her.

"Let me just grab my bags." Savannah gestured over her shoulder to the two large suitcases on the porch. "I have more in the rental car, but I'll get those later."

"Just come in," Mom told her "Cory, can you get Savannah's bags, please"

"Sure." I said, walking over to them.

"Cory!" Savannah exclaimed as I started to pass her to go onto the porch. "It's great to finally meet you!"

"Oh, jeez," Mom laughed, "Where the hell are my manners? Cory, this is Savannah."

"Nice to meet you." I said offering her my hand.

"And a pleasure to meet you." Savannah said softly, taking my hand between the two of hers. "I've heard so much about you!"

"Um... same here." I said looking down at our hands.

Savannah's skin was darker than mine and her hands were soft and smooth. Her slender fingers ended in long nails painted a deep purple and standing this close I could smell her perfume. She gave my hand a squeeze as she spoke,

"I have to say Cory, I've seen a lot of pictures of you, but they don't do you justice. You are a good looking young man."

Her hands left mine and to my surprise she placed them on my arms and gave my biceps a firm squeeze, "And the neck down is pretty impressive as well." Looking me in the eye, she added softly, "You must be making some lucky young lady, verrrry happy."

Those last few words came out in a purr and I swallowed hard as her deep brown eyes stared into mine.

"T...thank you." I stammered.

"And those eyes." She continued softly, "Bet you just melt the girls with those don't you?"

"I..uh, look like my dad." Was all I could come up with and I felt like a moron even as I did.

"That you do," she nodded, "But," reaching up she touched her fingernail to my cheek, "You don't look as miserable as he did. Your father was never happy, you look very sweet, Cory, and nothing will get you more with a lady then being sweet, right Carol?"

"Right, that and silly things like a job and no bad habits."

I started to ease away from Savannah, but she held my arm tighter and with a smile that seemed to have more than just good intentions behind it whispered, "Damn, you're eyes are beautiful."

This was said so softly I'm not sure mom picked up on it and my racing mind wondered if that was exactly how her best friend wanted it.

"So are yours." I replied just as quietly and hoping she wouldn't think I sounded stupid.

Savannah's smile grew and she gave me a wink that made my heart flutter.

"The bags Cory." Mom said in a tone that now caused my heart to miss a beat.

"Oh, sorry." I nodded and turning away from Savannah stepped on to the porch and reaching down grabbed the handles of her suitcases. As I lifted them and wondered what the hell she had packed inside of the heavy bags I heard my mother say something I couldn't catch, but did hear Savannah's reply of

"No worries, Carol, I'm no Mrs. Robinson." Something else from mom and Savannah laughed, "Just practicing I guess."

Feeling my face redden and hoping mom wasn't going to be pissed at me later thinking I was playing along, I opened the screen door and dragging the bags through said, "Do you want me to bring these upstairs for you?"

"Oh, that would be wonderful!" She answered as she untied the long jacket and began slipping it off. "If you could put them on the bed that would be great."

"No problem," I said picking up the cases, I lifted them higher than I needed to, trying to make a show of my arms bulging with the effort. "I'll put them..."

My voice fell off and I stood there trying to keep my jaw from hitting the floor. Beneath the long coat Savannah was wearing a tight low cut red blouse that showed off more than half of her smooth caramel breasts and I could make out the tops of a red lace bra.

Below the blouse was a black skirt that was so short calling it a mini would be doing it a favor. The skirt was as tight as the blouse and from my angle I could clearly see how it hugged her well rounded ass. Poking out from the skirt were the finest legs I had ever seen. Trailing my gaze down those legs I finally noticed the shoes she was wearing, were red heels that had to be at least four inches and made me wonder how she could walk in them.

Quickly following that thought was the idea those shoes were made for more than walking and most likely not the type that came off during sex. I had the vivid image of those shoes up in the air with those long legs spread wide. Staring at her smooth thighs and again admiring her beautiful complexion I wondered what her pussy would look like, or for that matter what color her nipples would be.

"Goddamn!" Mom exclaimed, "You say I look good? Holy shit, Savannah you look like you could be in a damn magazine!"

"Age is only a number," she replied and to both my delight and dismay, she put her arms over her head and with a laugh gave a quick spin for my mother.

That move sent her long hair whipping around and brought me another whiff of her perfume. I felt a stirring between my legs and was amazed to discover I was getting hard just standing here staring at her. "And after I lost that two hundred pounds of dead weight I'm feeling pretty damn young."

"And dressing it." Mom noted, "I wouldn't have the nerve."

"Well while I'm here I'll take your soccer mom ass shopping and we'll go hit a club." She winked at mom, "Maybe find us a couple of young men who want to be cougar fodder."

Oh, goddamn, I thought as my mother burst out laughing, cougar. That was exactly what Savannah was, a cougar the likes of which I only thought were on those porn sites and she was going to be sleeping in my bed for three weeks. I had no doubt when she was out with mom I would be slipping into my room and laying in my bed just imagining...

Mom's phone ringing cut into my thoughts and glancing at it, she rolled her eyes, "Its work, I have to take this."

"No worries," Savannah waved her off, "Do what you need to; I want to go change anyway." She laughed, "Don't think I wasn't thinking of that pool you brag about all the time."

"I don't know if it's warm enough for a swim," Mom said bringing the phone to her ear.

"Well, I'm going to anyway," she declared, then turning to me, smiled sweetly, "Cory will you be a dear and show me where I'll be staying?"

"Sure," I hoisted the bags again and this time the move wasn't lost on Savannah who made a show of looking at my arms again, "Ah, youth, it's wasted on the young."

"I guess." I said as I started to walk past her.

"Oh, it is." Savannah replied as she walked in front of me and over to the stairs. "See, girls your age think its always going to be fun. They're with good looking hot guys like you and the sex is great and they think it will always be that way."

I looked nervously over my shoulder, but saw mom was now sitting on the couch, her back to us while speaking on the phone. I didn't respond to Savannah's remark about sex as I wasn't sure what to say that wouldn't make me sound like a fool. It didn't matter as she began to climb the stairs ahead of me and continued speaking.

"But, trust me your mom and I can tell you that isn't true. We had a lot of fun in school." She laughed, "Your mother was not the good girl she wants you to think she is and I was quite a party girl."

I was having a hard time focusing on her words as she walked up the stairs ahead of me. Initially I wondered why she would go first seeing she'd never been here before, but right now I wasn't complaining.