Milf Tails: She's So Shy!

"You're just saying that." I grinned.

"No, not at all, you're a nice looking boy, Sam."

"Well if you want me to believe that you have to believe it when I say how pretty you are."

She looked at me for a moment, then burst out laughing, "Deal!"

"So, what happened, why were you crying?"

She sighed, "Its my birthday and I had plans with Ralph. He's the first guy I've dated since the divorce."

"Wasted a lot of time." I told her, "Guys would line up for you."

"Please," She waved her hand. "Anyway he said he wanted to take me out tonight, but I figured instead we would stay in and..." She stopped and I laughed when she blushed again, "Sorry! I shouldn't talk like that."

"Come on, Miss Warner, I'm twenty, not twelve." I shrugged, "You wanted to have a fun sexy birthday, nothing wrong with that."

"I guess, but Ralph calls and starts saying he can't come get me and I tell him what I was planning and he said he would come over." She looked down, "Then he says "It's about time you woke up, I didn't think you'd ever be ready to put out."

"What a prick!" I exclaimed, "Oh, sorry, Miss..."

"First off don't be because he is a prick. Second..." She smiled, "Call me Robin."

"Robin?" I repeated.

"Yes, after all we are having an adult conversation, right?"

"Sure."

"And as I said before, and meant it, you are a man now, not a boy." She cocked her head and looked me up and down, "That girl's doesn't know what she tossed away, Sam. You're attractive, smart, funny and sweet and sweet is rare at your age," She rolled her eyes, "Or Ralph's age."

"I don't think I'm sweet." I said that as my eyes fought to stay on her face and avoid the cleavage her robe was showing off.

"I do. Look at you. A Friday night and here you are talking to your friend's mom because you saw she was upset."

"Its your birthday, you should be happy and having fun, not crying and being alone."

"Hmm." She gave me an odd look, then one of the shy little smiles she was known for, the kind that seemed out of place on woman her age, especially one with her looks. "I think you're right, I should be having some fun, shouldn't I?"

"Hell yeah." I nodded, "Hot milf like you? You should be out celebrating and..." I gave her an exaggerated wink, "Who know, maybe getting lucky."

"I have to admit, it's been a long time since I've gotten lucky." She frowned again, "If I ever was. It took me a long time to realize Dave's father wasn't as good to me as I thought he was. He blamed me for fooling around with those girls, said I was too boring and dressed..." She shrugged, "like an old lady."

"You dress proper, not slutty and that makes you hotter, because you don't put it out there for everyone, you leave it to the imagination." As she had done, I put my hand over hers, "You're a sexy lady, not some slut."

"Sometimes I wonder if I could be both." She sighed, "Lady in public, but..." She blushed again. "Fun where it counts."

"Oh, I bet you could, you just need the right guy."

"Who would be the right guy?"

"I don't know." I thought about it, "I think someone who appreciates you and not just that you're pretty and sweet, but..." I hesitated, and then figured what the hell, her own son told me to make her feel good about, "That you're sexy."

"I'm sexy?"

"I told you that, but not slutty sexy, but...like classy sexy." I shrugged, "Cute sexy too, the way you look, but you still blush? That's hot and..."

I stopped because I sounded pathetic, telling my best friend's mother she was hot multiple times in the same damn sentence.

"You know, I am kind of hot." She nodded.

"Not just kind of you're...oh."

I felt like an idiot when she removed the comforter. My eyes fastened on her legs when she bent her knee and ran her nails along her thigh. That thigh was smooth and damn inviting looking and as her robe slid back I had to force myself not to look to the left and try to see between her legs.

"Sweating." She said, "Hot in here."

"A little, I guess."

"Maybe because I'm lying down." She turned to the side, swinging her legs off the bed.

Robin was now sitting next to me and before I managed to raise my eyes to her face, I caught a look inside her robe and saw the inner half of her left breast and a hint of red lace.

"So back to me finding this right guy."

"Well, I think you have to leave the house to do that," I laughed.

She smiled at me and moved over so her hip was touching mine. I could smell her perfume and her long blonde hair was tickling my arm beneath my sleeve.

"Who says?"

What did that mean? I gave her a nervous smile and forced a laugh, "Hey, you have someone hiding under the bed?"

"Not under it, but maybe on it."

"On..." I stopped when she put her hand over mine.

"You know, today is my birthday and it was going to be a happy one. Know why?"

"You were going to um...have nice night?" As bold as I had been I wasn't about to say 'get laid'

"I was going to cut loose tonight." She tugged on the top of the robe, "I haven't worn this in a long time and I went out and bought something sexy for under it." She giggled "I think I blushed when I paid for it."

"Bet you did," I looked down as she ran her nails across the back of my hand and up my arm.

I shivered at the contact and my cock swelled as I let my eyes wander down to her chest where the robe had opened more form her pulling on it.

"I did, but when I got into it I felt so sexy!" She smiled, "I was so looking forward to not being such a good girl tonight." She sighed, "But then Ralph turned into a pig and I guess I'm glad it was before and not after."

"I agree."

"So I figured the night was ruined, then a good looking young man brought me flowers and told me how beautiful I am." She coked her head and winked at me, "And I know he's not lying because he's been staring at me since he came in my room."

My face grew hot, but not all with embarrassment. Her nails were running up and down my arm and my eyes were blatantly on her breasts and as she had just said, she knew it. Her breasts were rising and falling rapidly and when she stopped moving her hand and left it on my bicep I could feel her fingers trembling.

My heart raced at the thought Robin was into me and my cock was now fully erect and aching with desire. I was torn between going for it and kissing her or letting her make the first move in case I was wrong or she decided to change her mind.

"I have been looking," I said softly, "I like what I see."

"And I like you looking," she replied, "Which brings me back to my birthday."

Robin gave me a nervous smile that caused my heart to flutter and my cock to twitch, "I think that maybe, just maybe I might enjoy my birthday after all."

"Yeah?" I swallowed nervously as she caressed my cheek and leaned closer to me.

"Well, its up to you, Sam." Her face was inches from mine and her head tilted to the side as she continued, "Do you want to give me a lonely, sad woman a happy birthday?"

I had to hold back a 'hell yeah' and as I paused to try to say something that made me sound confident, I recalled who Robin was. She wasn't just a hot milf she was...

"But, Dave." I said, pushing the words out so I wouldn't change my mind, "He's...my friend."

"And he's my son and he's been pushing me to have fun, my son wants me happy. I think you can make me happy, Sam." She squeezed my arm, "I'd like to make you happy, after all we were both treated poorly tonight, so how about we show those jerks and have some fun together?"

"You...you won't tell him?"

Robin shook her head and stood up. Thinking she had changed her mind I asked,

"Hey, um...where are you going?"

"Nowhere." She lifted the ties to her robe and held them out to me, "I thought maybe you might want to un-wrap me and see what I bought today."

I took the ties in my fingers, "I thought you were supposed to be unwrapping things, its your birthday."

"Oh, I'll be opening a present soon," She stared pointedly at my crotch, "Looks like a nice big present."

"I...I don't know about that." My face grew red.

"Looks big and..." She licked her lips, "I know its all for me, isn't it?"

"Oh, it is."

"Well Sam," she said softly, "I'm not a very good cougar. I'm nervous, I'm shy and a little out of practice." She smiled down at me, "But I see you're a little nervous to and I like that. I...I don't want to be with a cocky jerk, I want to be with someone nice."

"I can be nice." I agreed still hesitating on pulling on her robe.

"But I want a nice person to not be nice with, but the longer it takes the more nervous I am so..." she let out a long breath, "How about you open my robe and see what I have for you?"

I was blown away by the fact she wanted me to make the first move. Pushing Dave out of my mind, after all Robin was right; he wanted her happy. He even told me to try to make her feel good! So in a way wouldn't making his mom happy be doing a friend a favor?

I pulled on the ties and as the robe fell open, I whistled, "Goddamn!"

Robin giggled and turned as red as the outfit she was wearing beneath the robe. The lingerie was a one piece made completely of red lace that exposed her breasts beneath it. The center was cut out to expose her flat stomach. The top clipped to a red thong that was no more than string with a patch of lace between her thighs.

Robin slid the robe from her shoulders, letting it fall to the floor and, still blushing asked, "Like it?"

"Love it, Christ you're so hot!" I breathed.

"Want to see the back?"

Robin turned around, showing off the fact that aside from one strap across the middle of her back and a red string between her cheeks, there was nothing there, but her smooth creamy skin. Her hips had some curve to them as did her sweet round ass. Unable to hold back, I put my hands on her hips, leaned forward and kissed the middle of her back.

"Oh, that was nice." She sighed. "Please do it again."

"You don't have to say please, trust me." I told her.

Moving her long hair to the side I pulled her back towards me and kissed the back of her neck. Robin purred and I proceeded to place a series of soft kisses across her shoulders, then between them, working my way down her back.

"So nice." She moaned, "That feels so nice!"

To my surprise she moved over so my leg was between hers and sat down on my knee. I was wearing shorts and I felt the heat from her pussy against my bare leg. Putting my hands on her shoulders, I continued to kiss her.

My cock was throbbing and as sexy as her outfit was, I was dying to get her out of it, but took my time. Robin wasn't a sex starved milf from the porn movies I watched, Robin was sweet and looking to be enjoyed.

I wanted to enjoy her and at this point knew this was no game and was sure she would get around to making sure I enjoyed her as well. I continued to kiss her back, I let my hands slide down her arms, then around her waist. She sighed when I caressed her soft stomach, then taking my hands in hers guided them up to her breasts.

I moaned as I fondled her large heavy breasts and Robin gasped when my fingers zeroed in on her nipples. I rubbed them through the thin lace and Robin slid further up my leg, until her back was against me. She let her head fall to the side, exposing her neck and I fastened my lips to her soft skin.

Robin purred and moved her hips, grinding her ass onto my swollen cock. I slid my fingers inside the inner part of the lingerie and teased them along the edges of her tits. I pushed my hand down further and she whimpered when my finger came into contact with her bare nipple.

"Take it down." She whispered, while taking my hand and placing it on the strap on her shoulder.

I removed my hand from onside her top and taking the straps slid them down her arms. Robin removed her arms from them and once more leading my hands brought them to the clips that were attached to the thong.

My fingers were shaking, causing me to fumble with them for a moment. I was further distracted by her working her hips, sliding her ass along my cock.

The shorts were thin cotton and I moaned at how good her rubbing it felt. The clips gave and pulling the top from around her, Robin tossed it to the side. I made to draw her back into me but she stood up and hooking her thumbs into the thong, pulled it partway down her ass.

"Want to see?" She asked, looking at me over her shoulder and giving me that adorable shy smile.

"Damn straight."

She pulled the string down a little more, "You sure?"

"Stop teasing you little tart!" I laughed, "Let's see the birthday girl in her birthday suit."

"Oh, I don't plan on teasing you, honey." She winked, and then with a sexy little shimmy worked the thong down over the curve of her ass.

The crotch of the thong stuck to her pussy as she tugged it down and as she bent over to push it past her knees I licked my lips at the sight of her pussy peering out from between her thighs. She playfully kicked the thong off and turned to face me.

"Oh my God." I whispered at the sight of my best friend's mother completely naked in front of me.

Robins tits were amazing, bigger than those of any girl I'd messed with before and standing up well for their size, her large nipples were light pink and as hard as my cock. My eyes wandered down her soft stomach to take in the small patch of blond fuzz just over her pink slit.

"I take it you like?"

My answer was to stand up, pull her into my arms so quickly she released a startled yelp, and press my lips to hers. Robin moaned as I kissed her hard, while crushing her against me and her arms slid around my waist as she eagerly returned my kiss. I pushed my tongue against her lips and I moaned when hers darted out to meet it then slipped into my mouth.

As we kissed my hands roamed over her body, caressing her back, her arms, the sides of her breasts and then cupped the well rounded cheeks of her ass. I gave them a squeeze, marveling at how soft she was and loving the enthusiasm of her kiss. Robin was all but attacking my mouth as she ground against me.

I caught a glimpse of us in the mirror. The fact I was still in my shorts and t-shirt and this gorgeous woman was naked in my arms was an additional thrill. As if on cue, Robin tugged on the bottom of my shirt and pulled it up to my chest.

I broke the kiss long enough for her to pull it over my head and toss it away.

"You have far too much clothing on." She told me, then leaned back in and kissed me.

Her hard nipples were poking into my chest and she wiggled side to side, working them across me. Her tongue danced across mine once more and I felt her unsnap my shorts. I groaned when she worked my zipper down and without hesitation put her hand in my boxers and grabbed my cock.

She moaned into my mouth as she wrapped her fingers around my shaft and stroked it. Her lips slid from mine and my heart skipped a beat when she pushed my shorts and underwear down over my hips. Robin looked down at my cock as she pumped it,

"God, you're so hard!" she cooed, "You do want me, don't you, baby?"

"Yes, I...damn that feels good." I told her as her other hand cupped my balls.

"It does." She breathed, then licked her lips, "Bet it tastes even better."

My reply was cut off when she grabbed my arms, turned me to the side, then gave me a shove that sent me into a sitting position on the bed. The way she had angled me had put my back partially against her headboard and when she straddled my legs and sat on my lap she pushed me hard against it.

After a quick, hard kiss, Robin put her hand behind my head and pulled my face to her breast. I eagerly opened wide and sucked her nipple into my mouth.

"Oh, yes!" She cried, "Suck on them, honey! They so need attention!"

Robin was overcoming her shyness and I was getting the feeling my sweet little milf might turn into one of those porn wild cats after all. I circled her hard nub with my tongue several times before sucking it into my mouth and moaned when Robin reached between us and grabbed my aching dick.

She pumped it slowly while I switched to sucking her other nipple while rubbing the one I had just been licking. Robin sighed and arched her back, shoving her tit further in to my mouth. I put my arm around her, holding her to me and whimpered as she rubbed the sensitive head of my cock with the palm of her hand.

My cock was dripping and Robin resumed stroking me, her now slick hand feeling even better along my hard shaft. She placed my cock against her pussy and moved her hips, sliding me along the length of her soft wet pussy.

"Oh, fuck." I groaned around her nipple, "You're so wet!"

"I'm wet because I got a sweet and," she squeezed my cock, "Hard young man for my birthday."

Robin lifted her leg, placing her knee on my thigh, then did the same with the other so she was now kneeling on my legs.

Your cock feels so fucking good." She moaned, "I don't think I can wait!"

She slid my cock through the lips of her pussy once more, then shoved the head of my cock inside her and let her weight go.

We both cried out in pleasure as I penetrated her, plunging deep inside her hot, wet and every tight pussy.

"Yes!" Robin moaned in my ear as she ground her hips, working my cock further into her pussy, "Hmm, been a long time since I've had a nice hard cock inside me." She sighed, "And a nice big one too!"

She pushed her tit back into my mouth and I did the best I could to suck on it as she lifted her legs, sliding me most of the way out of her before sinking back down and taking me back into her wet heat.

Robin moaned softly as she rode me, bouncing on her knees on my lap. I put my hands on her hips and moved mine as much as I could, but being on the soft bed it wasn't easy. But it was okay because Robin began bouncing faster and harder and I moaned into her breast as she established a sexy rhythm on my cock.

Taking my face in her hands she lofted my head from her breasts and into a long, deep kiss. I put my arms around her and pulled her to me, crushing her breasts into my chest as she continued to ride me.

My hands slid down to her hips and I pulled on them, guiding her as she fucked me. Robin was sighing into our kiss each time she came down, pushing me deep inside her and I longed to be able to fuck her harder, but as before knew it would be better to let her decide how we fucked.

My patience was quickly rewarded when Robin eased from my cock, slid off my legs and to my delight put her back to me, guided my cock back into her and sat down on my lap. This time it was a soft moan we released when she sank back onto my cock.

She pressed her back against my chest and as I reached around to play with her nipples, she placed her soft feet on my knees and resumed riding me. Robin's head was resting against my shoulder and turning my head I kissed her neck as she moved slowly along my shaft.

I moaned as she was going slow enough that I could feel her tight wet lips massaging every inch of me. Reaching between our legs she rubbed my balls and my hips jerked, sending me plunging deep inside her.

"You feel so good," she moaned, "Baby; your birthday girl needs to come!"

Grabbing my hand from her left breast she shocked me by putting my fingers on her clit.

"Not so shy now!" I laughed in her ear.

"Been shy too long, honey! This girl needs to have some fun!" She moaned as I captured her clit and rolled her pink nub between my fingers. "And I'm going to have fun coming on my sexy young lover's nice big dick!"

She had slowed down her riding me, which was a good thing as had she gone any faster I might be popping off before she was able to come! I rubbed her clit in circles and she relaxed against my chest, moaning contentedly as I continued to stroke her nipple while playing with her pussy.