tagMatureMom's Best Friend: A Virginity Lost

Mom's Best Friend: A Virginity Lost

bysilkstockingslover©

Summary: Nerd gets break of his life when MILF seduces him after seeing his big cock.

Note 1: This is a 2016 Summer Contest Story

Note 2: Thanks to Tex Beethoven, Robert, Dave and Wayne for editing.

Mom's Best Friend: A Virginity Lost

"God, if I don't get fucked soon I think my pussy will shrivel up like a raisin," Kendra, my Mom's best friend, said out of the blue.

I was just coming down the stairs and I shouldn't have overheard that! It was just before lunch and I had finally woken up just minutes ago following a wild night of dungeons and dragons that had gone until 3 am. I froze, and even held my breath for a few seconds. I really shouldn't have heard that!

Kendra was a super-hot MILF, my mom's best friend from high school, a cheerleader who had gotten knocked up on prom night (the biggest cliché in the world) and now at 41 was single. Both of her kids were gone all summer working overseas, and her divorce final a few months ago.

She had been the stereotypical hot cheerleader with blonde hair, blue eyes, big tits, a great ass and toned tanned legs. She was no longer a cheerleader (duh), but she still had all the rest in spades!

Her daughter, Tierra, was in my graduating class and was a younger, even bigger tittied girl who messed up a great head start by being a complete bitch.

I had enjoyed many a stroke fantasy on Tierra and her mother.

I knew for an absolute fact that my buddies and I were the only eighteen year old virgins in the entire universe. For the record, we were geeks, not nerds... which is a very important clarification to make... because it meant we were not academic geniuses... we were just technologically suave as well as major gamers (both video as well as board game).

In other words, I wasn't ugly, or super scrawny, I was as average looking as they came. I just had a heck of a time trying to talk to any girl... as did the rest of my gaming group... thus why the only parties I had ever attended were birthdays and game parties.

We also shared many movie nights... always raunchy sex comedies that made us envious.

It started with 'American Pie', but my dad's massive DVD collection had hundreds of eighties movies and our main go to movies included: 'Mischief', 'Private School', 'Private Resort', and the classic 'Porky's'.

God, high school seemed so much more fun back then and the guys getting laid didn't look so perfect like all the male models that star in teen movies now.

My Mom laughed, "I'm pretty sure that isn't how it works or my pussy would be a prune."

"You at least have Jake," Kendra said, Jake being my dad.

Mom scoffed, actually scoffed, saying, "He lasts a minute and then falls asleep."

"A good man makes sure you come first," Kendra said, information that I instantly filed in my long term memory... one more piece to the enigmatic puzzle that was the opposite sex.

"Yeah? Well Jake doesn't munch cunt at all," Mom replied, sounding long term frustrated. Plus, hearing my mom use the 'C' word had my mouth dropping open even as my cock went from asleep to rigidly alert in 3.5 seconds.

"Well, no one eats cunt better than your first," Kendra quipped.

Mom laughed, "Wow, that was a long time ago."

"I still remember you protesting you weren't a lesbian," Kendra said, laughing.

My hard cock flexed in my pants at my sudden vision of Kendra licking Mom's pussy.

"Well, I wasn't," Mom replied.

"You were that first night," Kendra disagreed, "and a lot of other nights after that."

Mom added, "And days, too. Remember when I went down on you in the girl's bathroom during chemistry class?"

"How could I forget?" Kendra laughed. "Next period I sat in English trying to concentrate on Hamlet with cum trickling down my legs."

"You should've worn panties," Mom quipped.

"You wouldn't let me! It gave you easier access so you could snack on me. Once you got the urge for my cream pie you never wanted to wait," Kendra countered.

"Man, that was a lifetime ago," Mom breathed with a sigh.

Kendra said, her tone playful, "Maybe it's time to travel back in time."

Mom gasped, "Kendra!"

I pulled my sweats and underwear down and began stroking my seven inch cock.

"I'm serious. I need a good fucking very soon and maybe that good fucking can be from you," she said.

Mom gasped yet again, "Kendra, what has gotten into you?"

"Nothing, and that is the precise difficulty," Kendra answered. "Seriously... I need you either to come and munch on my pussy, or to fuck me. Do you have any cucumbers?"

Maybe they would have fucked right then and there but that was the threshold when too much blood had finally reached the tipping point as it had travelled from my head to my cock, so I fainted and tumbled down the stairs.

"What the...?" Mom gasped, her maternal instincts kicking in as her precious little boy fell down the stairs, his sweats and underwear at his ankles.

Both women rushed to the end of the stairs to discover me on my back, unable to move in excruciating pain, my hard cock saluting them both.

I stammered, "I-I-I'm sorry, I didn't mean to...!"

"Well, he doesn't get that from his father now does he?" Kendra exulted, staring at my erect dick.

"Put that thing away," my mother demanded, mortified, but still sneaking a look at my cock.

"Okay, but take your time," Kendra smiled, amused as hell and still devouring my rigid cock with her eyes.

"Kendra, don't encourage this," my Mother said.

"What? He's eighteen," she said, as I struggled to wrestle my sweats up my legs. "He is, isn't he?"

"That has nothing to do with it," Mom said, clearly still appalled by what had just happened and probably also very worried about how much I had heard.

Sweats and underwear now in place more or less, I scurried upstairs, trying to fight through the pain coursing through me, as Kendra called out to me, "Very impressive, Eddie."

"Kendra!" My mom scolded.

"What? It is very impressive. You have to admit that," Kendra said, "How long has it been since you've seen it?" just before I slammed my bedroom door shut and unfortunately couldn't hear my mom's next response.

As I collapsed on my bed my head was swirling with emotions:

-Embarrassed at being caught with my pants down... literally.

-Excited at all I had just heard and learned about my mom's lesbian past.

-Flattered that Kendra liked my cock.

-Aroused by my mental pictures of Kendra and my mom eating each other out.

-Really intrigued and flattered that Kendra liked my cock.

Replaying the shocking words I had heard and the shocking truths from the past I had also heard, my cock was still rock hard. It seems that lust overrides shame. Ask me if I care.

I closed my eyes and began jerking off, imagining Mom and Kendra in the throes of lesbian passion. Now I should note here that although I've had many fantasy girls starring in my stroke fantasies, Kendra is my number two and as sick and twisted as it may seem to you... get over it! What do you know?!... Mom has always been my number one... especially when she was wearing her white and red nurses' outfit with sheer white pantyhose.

I furiously stroked my cock, imagining Mom eating Kendra's pussy... still in awe that Mom had been a lesbian in high school.

In under a minute I was inches close to coming when my door burst open and Mom gasped, "Jesus Christ, Edwin!"

I was too far gone to have any control as my load erupted out of me and my cum flew through the air as both Mom and Kendra watched, but with very different facial expressions.

"Wow, that is a lot of cum," Kendra admired, again obviously impressed as she stared eagerly from behind my mother.

Mom was far more shocked than impressed. "Come downstairs once you clean up," she said tersely as she briefly glanced down at my cock before stalking away.

Kendra however, remained to watch as the final rope of my cum fluttered down to my stomach, the look on her face one of mischievousness. She winked at me before also leaving.

I was again mortified even though I had never come so hard in my life.

I stood up, cleaned my mess and changed clothes.

Nervously I headed downstairs, even though I was kind of curious how much trouble Mom would be willing to announce I was in with Kendra listening.

I walked into the kitchen and Mom and Kendra were in a sixty-nine, their heads buried in between each other's legs.

I'm sorry, dear reader, I was just kidding... although that would have been awesome.

They were at the table looking at each other but not talking.

"Have a seat, Edwin," Mom instructed, sounding as nervous as I felt.

I did, avoiding eye contact.

"How long were you eavesdropping?" Mom asked.

"A while," I mumbled, feeling guilty.

"Did you hear the entire conversation?" Mom asked.

I nodded, trying to avoid speaking as long as possible.

"Well, I'm not happy about you listening in on a private conversation, but we shouldn't have been having such a conversation in the first place," Mom said, glancing at Kendra.

Kendra finally chipped in. "Alice, he is eighteen. He knows that adults have frank conversations and sometimes those conversations are sexual."

"Yes, but...." Mom began.

"Enough, Alice," Kendra interrupted my mother, something I had never seen anyone brave enough to attempt. Mom was a strong-willed woman and not one to be told what to do.

To my surprise, Mom closed her mouth and waited.

I looked up from my lap for the first time, to see my Mom's face as red as the fiery gates of hell, not out of anger though, but embarrassment.

Kendra said, "I'm sorry you heard that conversation Edwin. It was just me whining about my lack of a sex life and me fondly recalling some wonderful times I'd shared with your mother in our past."

"Something we have not done since college," Mom clarified immediately.

I felt a hand on my left leg, hidden from my Mom by the tablecloth as Kendra continued, "Yes, your mother turned all prudish once she met your father."

"I did not," Mom protested. "I just became an adult."

"Adulthood is no fun," Kendra sighed, as her hand slithered slowly up my leg.

"Oh Kendra," Mom sighed this time, "life is what you make of it."

"Exactly," Kendra said, as her wandering hand had finally ventured as far as my suddenly growing cock. "Life is for the now. Isn't that right, Eddie?"

Kendra squeezed my cock, deliberately leading the witness, but I only stammered, "I-I-I guess."

"Edwin, I'm sorry you had to learn about my past in such an embarrassing way, but that is in my past," Mom said, stressing the word 'past' as she made eye contact with Kendra.

"Okay, okay," Kendra shrugged, her hand now sneaking inside my sweats and grasping my raging hard on, "I was simply trying to break the monotony of our current lives."

I tried not to groan and give anything away as her hand slowly, secretly, stroked my cock. Another first. Nobody had ever done that before!

"My life is not monotonous," Mom defended standing up, as Kendra's finger rolled around my cock head. I glanced down at Mom's silk-clad white legs and feet, wearing her sexy nurses' outfit, making my cock jerk in Kendra's hand. I scooted my chair closer to the table.

"Marriage is monotonous," Kendra countered, "and that's unavoidable unless you cheat or swing," as her finger continued to roll around my cock head.

"I need to go to the washroom," Mom said clearly wanting this conversation to end, before joking to me, "try not to expose yourself again while I'm gone."

As soon as Mom had walked out of the kitchen, my eyes following her legs until we heard the door close, Kendra dropped to her knees, and gushed, "I want a closer look at your fucking snake, Eddie."

I was speechless, I had visualised so many feverish fantasies of moments very much like this one starring Kendra. And now she was crawling under the table, wanting to spend some quality time with my cock... meanwhile starring in my own, living colour, live action porn movie.

"Oh my, this thing is fucking perfect," she said, as she resumed stroking it. "How did I not know about this massive fuck stick all this time?"

I was paralyzed with indecision. My Mom would be coming back in a couple of minutes! But even if she walked back through the door this very instant, this was a dream come true!

"Want me to suck it, Eddie?" she asked. I tried very hard not to faint again.

"But what about Mooooooooom?" I prevaricated, even as I felt her heavenly lips wrapping themselves around my very sensitive rod.

"Oh God," I moaned, completely overwhelmed by what was happening and in awe of how amazing it felt to have a mouth slobbering on my cock. Kendra's mouth slobbering on my cock! You can fantasize about it, but nothing compares with the reality of having it actually happen.

She bobbed up and down for maybe a minute, slobbering sounds echoing, before I heard the toilet flush. Although I was in heaven, I knew I had to warn her, "The toilet just flushed."

She sucked for a few more seconds before she moved back up to her chair, leaving me with a raging hard-on. I quickly managed to stuff my cock back in my sweats a few seconds before Mom returned.

I asked, suddenly super uncomfortable and needing to deal with my cock. It was about to burst! "C-c-can I go shower?"

"Sure," Mom said.

I stood up, my now full scale erection patently obvious through the sweats I had put on. Kendra chortled, "You'd better make sure it's a cold shower."

"Kendra!" Mom said exasperated, even as she glanced down at my crotch and couldn't possibly avoid seeing the bulge in my sweats.

As I hurried from the room, Kendra responded, "What? I'm just giving him a great suggestion."

Mom laughed, "You need a cold shower."

"I need something all right," Kendra agreed, just before I was out of ear reach.

I wanted to keep listening, but was pretty confident that if I got caught eavesdropping again I would soon be guest of honour at a funeral... mine.

I got in the shower, cock fully erect, and followed Kendra's advice. I turned the water on cold... not freezing... but hopefully enough to calm down my beast that was already fully loaded for round two.

True confession time: I usually jerked off at least four times a day, and had once done it eleven times (but God was I chafed the next day).

This time my dick just laughed at cold water. It was always a tough fucker (haha) and after what I had just experienced remained cocked (haha again) and ready for action even as the cold water tried to extinguish the fire in my loins... overwhelmed by my memory of how good it had felt to have Kendra's mouth wrapped around my cock.

No girl had ever touched my dick, and now that I had just had a just a quick introduction to a blow job I wanted more. You can't replicate pleasure like that just by masturbating.

Kendra had sucked on my dick while Mom had been just next door in the bathroom.

Fuck, she was definitely going to be my lone stroke session fantasy for a while... I even remembered a hot picture of her from Halloween when she was dressed as a slutty nun, the tops of her thigh high black stockings in clear view and her cute shoeless feet in those sheer silk stockings displaying her pink painted toenails.

That picture had been a stroke fantasy in the past and had just been promoted to the top of the queue for the next one.

I took a long shower, knowing if I lingered at least fifteen minutes Mom would probably have left for work.

And my cock, although determined, did eventually, and reluctantly, go into slumber once I stopped trying to figure out Kendra's intentions and forced myself to mentally replay the second world championship chess game of Capablanca vs Lasker in 1921 (I told you I was a geek.)

But even though I was now flaccid, I couldn't stop thinking about Kendra.

Was she just playing with my mind?

Was she so horny she couldn't resist?

Did my dick really impress her that much?

Fuck! I wish I was the kind of guy who knew how to hit on an older woman... but truthfully, I didn't have the remotest idea of how to hit on any girl, any woman.

I looked through the bathroom window at the driveway and saw Mom's car was gone, so I assumed the coast was clear and I went downstairs.

I arrived in the kitchen and saw a note not from Mom, but Kendra:

Hey Big boy,

I need someone to mow a lawn before my open house later this afternoon. Are you available?

Kendra

Thinking maybe, just maybe, please maybe, this could lead to something sexual with her and in any case I could use the money, I texted her:

Sure. When and where?

She texted back ASAP reminding me of her address.

I responded that I could be there in twenty minutes.

She responded that the lawn mower was in the shed in the back and it was unlocked.

I had mowed her lawn a few times before, so I knew the routine. The lawn was likely a disaster, but she paid well.

I drove to the address and as usual it looked like it hadn't been maintained all summer.

I sighed, knowing that this was going to take a while.

When I got to the shed I sighed again. The lawn mower was still an antique.

It took me ten minutes to get it going, but it finally started and for the next hour and a half I mowed the lawn. To make matters worse it had to be 100 degrees outside and my entire body had become covered with sweat within minutes. And this was a humid heat... you know the kind... where the sweat just sits on your skin without doing anything helpful.

Kendra came outside to her porch and gave me a wave, wearing an entirely different outfit than before, a nice red dress that showcased her big tits, and sheer black silk hose. Again no shoes. My cock was instantly hard again as I replayed this morning in its entirety... the real and the fantasy... especially my newest MILF stroke fantasy of Kendra being in awe of my cock and even saying so before sucking it into her wet mouth.

God, I wanted this MILF.

God, I wanted her mouth back on my cock.

God, I wanted to watch her sucking my cock.

God, I wanted to come in her mouth.

I waved back like a geek, totally distracted by this goddess, so of course I crashed the lawn mower into a concrete statue.

She laughed, and I shrugged at her, resuming the task at hand, even as my hidden cock secretly saluted her.

When I looked back up she had gone back inside. I sighed at my clumsy ineptitude... although that particular clumsy ineptitude had at least triggered my memory of the surreal experience of earlier today.

Although I knew it was unlikely, I held out hope that her comments, her looks and her brief oral embrace of my cock foreshadowed my fucking her.

God, how I wanted to fuck Kendra.

I finished the lawn, still covered in sweat, and went to tell her I was done.

Usually she paid me on the spot and that would be awesome. I wanted to pick up the new PlayStation game Resident Evil 4.

I knocked on the back door and she called out, "Come on in, I need some help inside."

I opened the door and warned, "I'm kind of sweaty and covered with grass trimmings."

"Okay. Then get undressed over there and go take a quick shower," she instructed, as she put icing on cupcakes.

"Really?" I asked, intrigued by her suggestion, even though she'd spoken rather casually.

"I've already seen what you hide down there Eddie," she said, smiling at me. "And I have to admit it is a pretty impressive package."

"T-t-thanks," I stammered, in awe of such flattery from the hottest MILF I knew... even hotter than her daughter, since Kendra was in no way a bitch.

"Well, hurry up, big boy," she grinned, "we've got lots to do and not much time to do it."

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