tagMatureMilf Tails: She's So Shy!

Milf Tails: She's So Shy!

bylovecraft68©

Author's Note: Welcome to the latest installment of Milf Tails. This series has gone over very well and I'm glad everyone is enjoying it. I hope that enjoyment continues with this new edition. Lovecraft68

*****

I pulled up in front of Dave's house and sat in the car working up the nerve to ask to borrow money. Not that he wouldn't do it; but I knew things had been tough for him and his mother in the year since his father had left for California to chase some slut he'd been banging.

But I could pay him back next week when I got my paycheck from Stop and Shop and really needed the money today. I looked down at the passenger seat at the bouquet of colorful flowers I'd spent the last of my money on. The flowers were for Kim who had called me yesterday to say we were through because she didn't think I paid enough attention to her.

I didn't feel that was true and had the sinking feeling she knew it too and this was a cop out to start seeing someone else. But Kim was pretty, a lot of fun and, when in the mood, a damn good lay, better than the two other girls I'd messed around with back in high school.

I didn't think she was 'the one' as my mother would say, but she was a great 'miss right now' and I didn't want to give up on it just yet. As I got out of the car and made my way up the walkway to their door I reviewed my plan.

Go to the apartment she shared with her room mates, give her the flowers, apologize, then if that got me back in her good graces take her to Lupos where her favorite local band was playing. Which is why I needed fifty bucks, I had a few bucks to spend but the tickets were twenty five a pop.

I knocked and fidgeted until Dave opened the door, "Hey Sam!" he stepped aside for me to come in, "What's going on?"

"Oh, well um..." I stopped, once again feeling bad about needing a favor. Noting he was wearing his Domino's shirt and cap, I stalled, "I thought you had Friday nights off?"

"Someone called out and I could use the hours," He shrugged, "Besides I'm riding solo since Tonya dropped me and I needed to be out of here tonight anyway."

"Why do you have to..."

"Why do you look nervous?" He cut me off.

I sighed, "Kim broke up with me."

"Oh, well, hey, welcome to the club." He grinned, "Want to borrow some hand lotion and exchange links to dirty movies?"

"Hopefully not yet, I'm going to try and get back with her."

"Good luck, but I need to get going soon, you need anything?"

"Yeah uh...I feel like an ass asking, but I'm trying to get her to go to a show with me tonight and you wouldn't happen to have fifty until Wednesday would you?"

"Jeez, not that much, no." He shrugged. "Sorry, Sam."

"It's okay." I shrugged, "I figured you might not and..."

I stopped at the sound of heels on the hardwood floor and looked up to see Dave's mom, Robin enter the room. Normally I would have said hello, but normally, Robin wasn't dressed the way she was now.

Dave's mom was hot, damn hot, but in a prim, sort of girl-or in her case-milf next door- way. Robin had gorgeous blonde hair she wore up or pinned back with a head band most of the time and wore little if any make up. She was on the taller side and had legs that went on forever, but did everything she could to hide them.

Her mode of dress was either business suits with shapeless baggy slacks or skirts that were always knee length. The only reason I knew she had nice legs was I'd been sleeping over here and there since I'd been fourteen and had seen her in shorts a couple of times and one thrilling instance of seeing her in a bathing suit.

Even then, as soon as she realized I was there, the shorts were replaced by loose fitting jeans and she had quickly left the pool the time I'd dropped by and seen her sun bathing. She had emerged from the house in a long sundress that had gone down to her damn ankles.

Robin wasn't chubby by any means, but not exactly petite and the couple of brief glimpses of her wearing something that flattered her figure displayed a sweet curvy ass and a pretty damn impressive set of tits.

I'd always found it odd that it was the fact Robin didn't show herself off that turned me on about her. Must be that expression, leaving things to the imagination and I would be a liar if I tried to deny imagining her body many times in the six years I'd been friends with Dave.

But right now...Robin had quite a bit on display and I was not minding at all! She was wearing a short red robe that barely went past her ass and a pair of red fuck me stiletto heels that strapped around her ankles.

Those shoes did amazing things for her already damn fine legs and my eyes enjoyed the long journey up and down those shapely legs, lingering on her lush thighs. The robe was open at the top enough to show some cleavage-something she never displayed- and the sight of the round tops of her breasts caused my heart to skip a beat.

I swore I could see a hint of red lace and wondered what was beneath it. Completing this damn sexy makeover of my friend's normally proper mother was her long blonde hair was not just down, but teased out. There were some blonde ringlets framing her face and I was struck with how pretty she was.

The deep red lipstick she was wearing added to that beauty, showing off her full lips and a mouth that definitely looked as if she would be good at a very specific skill.

"Dave!" She exclaimed, Startling me out of what had to have been some blatant staring. "I thought you were at work!"

"No," He shook his head, "I told you they didn't need me until seven, I was just leaving, when..."

"Sam!" Her eyes fell on me, "Oh my God!" I had to hold back a laugh as her face turned as red as her robe. "I...I am so sorry! Look at me!"

"Don't be sorry," I laughed, "I'm not."

I realized how bad that sounded, but noticed Dave didn't seem upset, in fact he laughed too,

"Hey. See that mom? I told you, you were Milf!"

"Dave don't be rude!" She waved her hand at him and I caught a glimpse of her long red nails.

A quick glance back to the shoes showed off her toes matched and I wished I could get a damn picture of her like this, but something told me my imagination would hold onto this image for quite some time.

"I'm...I wasn't excepting you to be here. I heard the door and thought it was..."

"Ralph." Dave now had an unhappy look on his face. "Don't worry I'll be gone in a couple of minutes."

"Fine." She tightened the robe around herself, "And I'm sorry you saw me like this Sam. Even if you're not, it's not very proper."

"No worries, Miss Warner." I shrugged, "You're not showing that much." Although for her she was and I wouldn't be opposed to seeing more.

"I am." She looked down at her legs, "And it's not like...well, I know what I look like I'm doing."

"What you will be." Dave rolled his eyes, "You're a grown woman, mom, and its okay to have fun."

Her blush deepened and despite the fact I saw her as hot...I just wanted to take her in my arms and give her a kiss, she was so damn cute! I'd never met a woman so good looking who was so shy.

"Well, okay, now that I made a fool of myself in front of my son and made Sam see more of me than he would want to, I'm going to go in my room and die of embarrassment."

I bit back a remark that Sam would want to see much, much more and said, "I have to go too." I looked at Dave, "Thanks anyway."

He nodded and I watched Robin leave the room and walk down the hallway towards her room. I drank in the smooth backs of her legs and marveled at how high those damn fuck me shoes were. Whoever Ralph was he was a luck bastard! I looked up to see Dave watching me ogle his mother.

"Sorry, man." I grinned sheepishly.

"I don't care." He sighed, "Hate to say it, but I'm glad you made that dumb remark."

"You are?"

"Yea, I am." He shook his head, "You know, Sam, my mom is really a beautiful woman. In fact mom, or not, I think she's pretty hot.

"Whoa!" I laughed, "Dude, that's your mom!"

"I didn't say I wanted to touch her, you moron." He punched my arm, but was grinning, "This isn't one of those crazy taboo porn movies. My point is she's shy and doesn't think she's that good looking."

"Well would you rather her be slutting around, showing it off?"

"No, but I'd like her to be confident enough to see she is attractive and feel better about herself so she would meet someone."

"It seems she has, Ralph?"

"Ralph is a prick like my dad." Dave said disgustedly. "He makes cracks that she's not bad looking for her age, but that's okay, he thinks she's pretty."

"One of those." I shook my head, "I hate those guys."

"I do too, but Mom kept hiding herself away and he's the first guy she has dated since the divorce so I figure at least she has someone for now and when she sees he's an asshole and dumps him, she will know she can find someone."

"I still can't believe she really doesn't know she's hot!"

"My father met her in college and she was shy and he fed into that. He loved that she dressed boring and showed nothing, no competition for him. Then we find out the prick was fucking any young intern he could get his hands on."

"Yeah, that sucked, your mom is too sweet for that, she deserved better."

"And when she caught on and confronted him?" Dave was now pacing back and forth and looking agitated.

I stood there and let him rant, figuring the last year had been pretty upsetting for him as much as his mom.

"My asshole father then blames my mother for his cheating saying she was a prude, she dressed like an old lady, and she wasn't a confident woman so she drove him to it; made her feel bad about herself."

"That's low, man."

"Yeah...when he left I did everything I could to get her out and to meet someone and to dress sexier. I know that's odd for a son to do, but I wanted her to see guys reactions to her and see she has a lot to offer in every way. She's smart and sweet and pretty, she needs to know guys see the pretty part. Her friends tried too, but nothing."

"Where did she meet this guy?"

"A friend fixed her up, but surprised her so she couldn't say no. He's a jerk, but...like I said maybe she gets back in the saddle then says "Hey I can do this" and move on."

"So I guess tonight is saddle time."

"Yeah, my ass needs to not be here, so good thing for work. But it's her birthday so I'm glad she won't be alone."

"Shit, I didn't even tell her happy birthday!"

"That's okay, tell her next time. I have to..." He stopped and slapped his head. "Shit!"

"What's wrong?"

"I'm so stupid!" He laughed, "I'm thinking I'm broke because I put my money away for insurance, but I's not due until Next Friday."

"So you can lend it to me?"

"Yeah, but fuck!" He looked at his watch, "I have to go! Go in my room, in the top drawer of my desk there's an envelope, take fifty."

"Thanks man!" I shook his hand, "You'll get it back!"

"I know and hey, do me favor?"

"What?"

"If you see my mother again...tell her she looks nice, don't be a perv, but tell her happy birthday and how beautiful she is."

"Odd request, but sure!" I laughed, "I won't be lying!"

"Keep it in your shorts and just be nice to my mom, she could use it."

Dave left the house and as I headed down the hall to his room I thought I would like nothing more than to be 'nice' to his sweet and sexy mom.

*****

I hurried into Dave's room and looking in his desk found the envelope and removed the fifty dollars. Closing the drawer I looked at the small digital clock on his desk and frowned, it was close to seven. Kim went out Friday nights with her friends and if I wanted to catch her at home, my ass needed to get moving.

I exited his room and stopped in my tracks when I saw Robin walked away from me towards the living room. She was on her cell and I stayed where I was, taking advantage of being able to stare at her legs again.

"Ralph, what do you mean, you're not coming? All week you said you were coming over!"

Uh-oh, I thought and silently padded down the hallway. I didn't want her to see me, but didn't want to get caught lurking in the hallway either if she turned around.

"But...but honey, it's my birthday!" She was getting upset and I felt my stomach sink.

She turned the corner to go into the living room and I quickly reached the end and waited for a chance to bolt out the door so she wouldn't know I had heard anything.

"Ralph, please...I...I bought something new and...and fun." She paused, "Yes, that kind of fun I...I know I've been kind of shy, but its my birthday and I thought I could give you a gift too."

She hadn't slept with him yet. She was shy! She had crossed the living room and as she started to enter the dining room off of it I quickly made my way to the front door to leave. I eased the door open and as I stepped out heard Robin raise her voice. I couldn't make out the words, but a few seconds later, I heard her yell, "Then forget it you asshole!"

Good for her, I thought, then frowned when I heard her sob. She came walking back into the living room and as I slipped through the door I caught a glimpse of her walking past with her head down, crying. She headed for her room and part of me thought about asking if she were alright, but didn't want to embarrass her.

I walked to my car wondering if I should call Dave, but then he would either leave work and get in trouble or spend the rest of the night worrying about her. I got into my car and as I went to start it, my cell rang. I saw it was Kim and answered,

"Hey, Kim!"

"Thought you were coming over?" She asked.

"I never said that." I looked at the flowers and smiled.

"I heard you were, but you're not here."

"I had to stop for a couple of things." I rolled my eyes, I'd told one of her friends I was thinking of trying to talk to her tonight, big mistake.

"Guess I'm not that important then." She said, "But tell you what, get here in fifteen minutes and maybe I'll let you take me out and...if it's fun, maybe we have some fun."

I was ready to tell her I was on my way when my mind quickly replayed her last words...what a bitch! I had wanted to try to make it work, but seriously?

"Sam, you there?" she asked.

"Yeah, I'm here." I looked down at the flowers then glanced at Dave's house and thought of his mother in there crying. She was a sweet woman who was now alone on her birthday and here was this stuck up bitch taking it for granted I would jump when she snapped her fingers.

"Well, you coming or not?"

"No." I said, "But I bet you will be as soon as you find some jerk at the club tonight."

"What did you say?" She demanded.

"I said, piss off, Kim, I'm not going to be used." I hung up on her and leaned back in my seat.

It wasn't like I was in love with her or anything, but it still sucked getting treated like that. Well at least I could just give Dave his money back. I looked at the flowers and wondered what I could do with them, then thought of Robin. I smiled at the thought I could give them to her and say they were for her birthday, make her happy.

I grabbed the bouquet and made my way back up to the door. I hadn't locked it on my way out and let myself back in, this time locking it behind me in case her asshole boyfriend did show up, this way he couldn't just walk right in.

I looked for her in the dining room and kitchen and then headed for her bedroom. I hesitated outside her door and wondered how this would look. I then shrugged, how could it look? It's not like she would think I was giving the flowers to her because I was hot for her or anything. I listened at the door and frowned when I heard her sniffling in there.

I knocked and she called out, "Dave, is that you, honey. You forget something?"

"No, Miss Warner, its Sam, um...can I come in for a minute?"

"Sam? I...I guess."

I put my hand behind my back, hiding the flowers and opened the door. I figured she would have changed, especially seeing she told me to come in, but to my surprise-and pleasure-she was still in the sexy robe. I did notice the shoes were off and her long legs were stretched out on her bed. She was sitting up, her back against a pillow and a box of tissues next to her.

"What are you still doing here, Sam?" As she spoke, she grabbed the comforter and pulled it from the side of the bed, over her legs. "Everything okay?"

"With me? Sure, but you look like you're crying." I played dumb on having heard what had happened.

"Just some kind of disappointing news." She gave me a forced smile, "I'm okay, but..." Her eyes narrowed, "What are you hiding behind your back?"

"Well I felt like a jerk I didn't say it earlier so I ran down the street to get you something."

"Say what?"

"Happy birthday, Miss Warner!" I brought the flowers around with a flourish and handed them to her.

"Oh, how thoughtful!" She exclaimed and the smile she gave me made it worth blowing off that bitch and doing a good deed for someone who deserved it.

She took the flowers and smelled them, "They're beautiful!"

Recalling what Dave had asked me to do; I winked, "For a beautiful lady!"

"Oh, twenty and already using bad pick up lines?" She laughed, "That was smooth though and you looked serious."

"I am." I told her and wasn't lying, "You're a very attractive woman, Miss Warner."

"Aren't you sweet." She leaned over to her left and grabbed vase that had a single rose in it and tucked the flowers I gave her into it.

When she leaned over the sheet lifted up and I was given a good view of her bare hip as the robe rode up. I noticed a red string over her hip and figured she was wearing a thong under the robe, goddamn!

"So, um...why are you upset?"

"Oh." She returned to leaning against the bed, "It's nothing, thank you for the flowers and the pity compliments, but you can go."

"I meant what I said and...do you want to talk?"

"Please, its Friday night, a good looking young guy like you has to have something better to do than talk to frumpy old lady like me."

"Old lady? Hell no!" I shook my head.

"Old enough to be your mom." She pointed out.

"Age is a number," I pointed at her, "Look at you, Miss Warner, you look damn good. I wasn't kidding before." I grinned at her, "And milf's and cougars are the hottest thing in..." I caught myself

"In what?" She asked.

"Oh, uh..." I turned my head, "Porn. Sorry, totally not right to say."

She laughed, "You're blushing! You're a very sweet; I've always loved that about you."

"Thanks, you're sweet too." I smiled, "You were adorable out there when you were blushing."

"Adorable?" Her blue eyes twinkled and she laughed, "Oh, honey, you practicing for the club?"

"No I'm not that smooth." I looked down at her and realized here I was in her bedroom with her lying in front of me in a tiny robe with who knows what type of sexiness underneath it.

Not that anything would happen, but it was still a thrill and I didn't want to leave.

"But, you were pretty upset; sure you don't want to talk?"

"Please Sam, it's a nice offer, but like I said, I'm sure there is some pretty girl out there waiting for you." She paused, "Karen, is it?"

"Kim and we broke up."

"Oh, honey, that's too bad." She reached out and put her hand over mine.

I wasn't sure what was a bigger thrill, the contact or her calling me honey.

"It's okay, we weren't that serious and she was...well...kind of a bitch."

"Really? Or you saying that because you're mad."

I was going to say forget it, but she patted the bed, "Sit down and tell me about it."

I didn't have to be told twice and sat on the edge of the bed and turned to the side so I was facing her, As she sat there listening intently I told her about how Kim had broke up with me and my plan to get her back and how she had found out and what she'd said to me.

"Good for you, standing your ground." She patted my hand again, "I'm sure a good looking guy like you will find someone soon."

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