Mom's Best Friend: A Virginity Lost

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

She said this in such a sultry way, my already semi hard cock again became completely erect because of her, and I wondered at the possibilities of this encounter in a place where there was no possibility of my mom coming out of the bathroom and walking in on us.

God, I wanted this MILF. Am I repeating myself?

I took off my shirt, shoes and socks.

It didn't seem like she was watching, but as soon as I was down to my shorts she ordered, "Shorts too. We can't have any grass clippings cluttering up the house before a showing."

"Okay," I nodded, knowing my boxers would do nothing to hide the tent in my shorts.

Once I had them off, Kendra strolled over to me. I saw that she still wasn't wearing her heels and I found myself obsessed at the sight of her purple painted toenails showing through her silk hose. And by this time you won't be surprised to know that the sight made my hard cock flex.

She made no secret that she had noticed. "Did I make you do that?"

"It has a mind of its own," I joked weakly, even as my eyes remained where they were: gazing rapturously at her stocking-clad feet.

"You're the only guy I know who stares at my legs and feet but not my tits," she said incredulously, standing very closely in front of me.

I forced my gaze away from her feet and took in her tits briefly (which were also awesome) before gazing into her eyes (which were gorgeous) and admitting, "I'm a legs guy."

"But specifically you're a stockings guy aren't you?" she asked, so close to me I was getting lost in her perfume.

"Um... yeah," I confirmed, trying desperately not to look at her feet... which was what I really wanted to do.

"Well, I'm a 'big cock' girl," she said, reaching for my throbbing dick before adding, "and you have exactly what I want."

I groaned as her hand squeezed my cock.

"While you were in the shower what were you masturbating about?" she queried knowingly, as she reached inside my boxers.

"Oh, God," I groaned, her warm hand was on my cock again... and unbelievably it was so different this time. No worries about my Mom. No distractions. Just her and me. As her hand slowly stroked my raging hard-on, I couldn't believe the feelings I was experiencing. Each movement sent shivers through me and unlike the 'get the task done' focus I always had when I was stroking myself, I wanted this to last forever.

"Your cock is so fucking big, Eddie," she purred. "How do you not have the girls lining up?"

I laughed, "That is funny. Girls lining up for me? Put even one girl in front of me and I forget how to speak."

She surprised me again as she dropped to her knees and tugged my boxers down, continuing, "No, sweetheart, I'm serious. If the girls learned how big you are they would be fighting each other to have this thick dick pounding them."

"I don't think soooooo," I answered, forgetting how to speak right then and there as I watched her take my cock in her mouth.

I didn't know anything could feel so good until the first time she'd had her mouth around my cock, and now she was doing it again.

I mean you imagine this moment a dozen times a day as a guy. Cheerleaders, teachers, MILF's like Kendra, anyone actually, sucking your cock, but an inexperienced imagination cannot possibly capture the intense, surreal, euphoric sensation that I was experiencing right now.

As she slowly bobbed back and forth on my cock, I knew I wasn't going to last long. I sure wanted to. I had no idea when I could possibly have a girl do this to me again, but the reality of her volcanic ocean of a mouth, the most beautiful oxymoron in the universe, was too much.

I warned in under a minute (hopefully I would last at least thirty seconds), "I-I-I'm going to come."

Her response gave me a double shot of confidence and pleasure as she moaned on my cock, sending vibrations right through me as she simultaneously began bobbing faster, just like the porn stars in the many videos I watched online.

I was wondering if she was going to swallow when I suddenly erupted into her mouth. She kept bobbing, milking every drop out of me, yes swallowing, and I came so hard my knees buckled a bit as the most intense orgasm of my life ripped through me. I groaned, "Ohhhhh, God."

She kept sucking, although slowing down once she had taken my full load. She then stood back up and said casually, "God, I was craving that. 'Crave' is a strong word, but you earned it. Now go shower."

Before I could think of anything to say, feeling like I was on a sexual version of 'Punked', she turned round and casually returned to her cupcakes.

I left the kitchen toward the hallway, my cock still hard, completely naked and trying to process what had just transpired.

Once I decided I didn't care to rationalize anything, but just savour a fond new memory, I smiled as I reached her bathroom and realized the most amazing thing: I had just received my first blow job. I had just received my first blow job and it was from one of the women I had fantasized about doing exactly that hundreds of times.

I got in the shower, noticing there was a towel lying on the closed toilet seat. Had Kendra planned this all along?

As the water hit me, something else hit me: my clumsy humiliation of falling down the stairs and getting caught with my pants down (literally) had been a blessing in disguise.

Fuck, the world worked in mysterious ways.

I showered, washed my body thoroughly, including my cock and balls, just in case, by one more miracle, she was up for even more.

I got out, dried off and wrapped the towel around me... my cock finally in a flaccid state.

I started heading to the kitchen when I heard Kendra call out, "In here, Eddie. There is one more thing you need to work on before the open house."

I turned into the open door of her bedroom and gasped. Kendra was draped across her bed, naked except for a garter belt and stockings, bra and panties: all of them shiny black.

"Is this one of your fantasies, Eddie?" she asked, as she slid one stocking-clad foot up and down her other leg.

"Y-y-yeah," I stammered, in awe of what I was witnessing... my cock instantly snapping back to attention at lightning speed.

"Come here," she said, gesturing with her stocking-clad toes to wave me over. "And drop the towel."

I obeyed both orders as I dropped the towel and walked over to the bed literally salivating at what I was witnessing... refusing to pinch myself in case this was a dream.

When I reached the bed, she moved her feet to my cock and correctly prophesied, "I'm thinking you've never gotten a foot job."

"N-n-no," I stuttered, as both her sheer silk-clad feet wrapped themselves around my stiff rod.

"Have I mentioned how much I love your cock?" She asked demurely as she began giving me a foot job.

Finally building some confidence, beginning to emerge from my paralysis from everything she had done since I had set foot on those stairs, I answered slyly, "I think you may have mentioned something about that."

"That's the first thing I heard, and I haven't stopped thinking about it since," I admitted with heartfelt sincerity.

"And your mother rejected my very generous invitation of fucking me," she said coyly, as her toes rolled over my cock head. "Or eating me."

"Yes I heard that too," I groaned, the feeling of her sheer silk gliding across my cock head was amazing.

"Will you be rejecting those offers?" she pursued, now stroking her right foot across my chest.

Her silk foot on my chest also felt amazing. The idea of fucking her or eating her were both fantasies I would love to make come true. My confidence at an all-time high, I told her, "From you, those are offers I would never refuse. I think I'd kill myself first."

As she straightened her leg completely, her toes now reaching my lips, I took her silken clad ankle in my hands, opened my mouth and began sucking on her toes.

"Mmmmmm, that feels good," she encouraged. She added, her tone suddenly stern, "I want you to remember your promise."

I replied, "I think that is one I can keep."

As her other foot was massaging my balls, she emphasised, still sternly, "I'm serious, Eddie. I can be very sexually demanding and I'm going to want the use of this big dick on a regular basis."

I removed her toes from my mouth, wanting to warn her that I really had no clue what I was doing, "Ms. Williams, I have to warn you I've never done any of this before."

"No one has had this big dick yet?" She asked, genuinely surprised.

No," I admitted, before giving the sole of her foot a tender kiss. "Before you, I've never even kissed a girl."

"So I have an eighteen year old virgin in front of me?" she asked, clearly even more excited, before adding, "and none of that Ms. Williams crap. You call me Kendra."

"Yes, Ms... Kendra," I quickly corrected.

""So this delicious, hard, thick, delicious cock is all mine?" she asked, moving her foot back to my cock.

"You're the only one who has ever shown any interest in it," I responded, my insecurity clearly apparent.

"That won't be the case once the girls know you're carrying around an elephant's trunk," she predicted, returning to giving me a foot job. "Even your Mom was impressed."

"She was?" I asked, the idea of fucking my Mom the only fantasy I had stroked to more than my ones of doing Kendra.

"Oh yeah, didn't you see her go red when she saw it?"

"That was anger," I corrected, even though I now recalled her glancing furtively at my cock once before she'd left my bedroom after catching me ejaculating all over myself and had again noticed my hard cock through my sweats as I walked away from the kitchen table.

"No," Kendra shook her head, "that was 'Holy fuck! My son has a huge mother fucking dick! The scolding was her attempt to cover up her sudden fascination and her need to look like a proper mother."

I groaned hearing Kendra say 'mother fucker', the idea of me being a 'mother fucker' a dream to cherish.

She smiled wickedly, "Sweetheart, you want to fuck your Mommy, don't you?"

I didn't say anything, which in itself was a clear admission of guilt.

"You really are such a bad boy behind that geeky exterior," she purred, before adding, "you probably inherited that from your Mom. She used to be quite the slut back in the day."

I looked up at her unable to speak, and unsure what I would say if I could. The fantasy of fucking my mother was raging through my head and was warring with the knowledge that in real life I was about to fuck her best friend. I couldn't hold on to both thoughts and I was incapable of abandoning either, and I felt totally overwhelmed.

Kendra provided a much-needed distraction by asking, "And you have never eaten pussy either?" By this point that was pretty obvious. I had never done anything.

I shook my head no.

"Well, I wanted your mom to munch my box earlier, but I think you will do just fine," she said, as she wrapped her legs around me and drew me towards the box in question with her feet.

I stumbled awkwardly between her legs and managed to get to my knees and was now staring at the black panties that were hiding the first pussy I would ever see that wasn't on the internet.

"Hungry, Big Eddie?" She asked.

I nodded, still mentally comatose.

She lifted her ass up and ordered, not a request but an order, "Can you help me with these?"

"Sure," I nodded, my hands trembling as I reached up to her silk panties and tugged them down, realizing that her panties were draped over her garters which confirmed my already obvious assumption she had been planning on seducing me all along.

I pulled them down to uncover pink, wet pussy lips, with just a tuft of hair above her clit.

Once I had them off, she simpered, play-acting, "Like?"

"Love is a better descriptor," I smiled, as I tossed her panties away and moved back between her stocking-clad legs, no longer shy around this woman... by this time I knew that Kendra liked me, which was unbelievable, but also unquestionable... so my shyness was now swept aside and replaced by a strong determination to do nothing but please her.

"Good answer," she purred, as she wrapped her silky sheer legs around me and pulled me in, face first.

I didn't need any more instructions as I began licking. I had watched a lot of lesbian porn and also read a lot about the art of cunnilingus in hopeful preparation for this exact moment.

If female blogs told the truth, nothing made a woman happier than a man who knew how to eat her pussy. So I had spent hours researching and understanding, at least in theory, the inner workings of the female anatomy.

Although she was already wet, I began by slowly parting her pussy lips and exploring... recalling that I should just tease the pussy at first by going slow... I wasn't going to just eat her pussy, I was going to worship it.

And her taste, which had often been described in derogatory terms by guys claiming to know what pussy actually tasted like, Kendra's taste was surprisingly pleasant and almost nondescript... like water.

Her moans encouraged me and she said, "Oh yeah, that's it."

My cock twitched against the bed as I lapped her pussy and her fluids began to leak out in greater quantity, and to have a slightly stronger taste than her original wetness.

As I had ventured my way to now exploring every nook and cranny inside and out with the wonder of a child, I was rewarded by the sounds of her heavier breathing and her gentle moans.

Then to my surprise she abruptly asked, "Want to lose your virginity, Eddie?"

"God, yes!!!" I cried eagerly, even while I thought that this was easily the silliest question a guy could ever be asked.

"Then come up here and fuck me with that monster dick," she demanded in the sexiest way a woman could ever utter such a sentence.

Although I had wanted to get her off with my tongue, I wasn't going to reject the offer of a lifetime! I moved up and between her legs, trembling slightly at the reality that I was about to lose my virginity to one of the two women I had already fantasized losing it to hundreds... maybe thousands of times.

My cock head at her glistening pussy, I took a breath and slid my cock inside.

"Oh fuck, yes," she groaned loudly, as my entire cock disappeared inside her delightfully warm pussy... it was quite different from her mouth which really hadn't been all that warm. But both openings shared a great feeling of intense overwhelming pleasure, each different enough to make them distinct, but both of them glorious.

Instinct and common sense took over as I began pumping my hips and fucking her... thankful I had already come in her mouth, so this time the experience would last longer for both of us.

"Harder, Eddie. Slam that mother fucking prick deep in my hole," she moaned, wrapping her amazon silky clad legs snugly around me.

"Oh God, so good," I babbled, wanting her to know I was enjoying this as much as she was.

"I'll be your stocking wearing slut any time you want, Eddie," she promised as I fucked her hard and deep.

"Stocking wearing... Oh God. That will be every day," I moaned, wondering what idiot could ever possibly reject such an offer.

"I'll keep you do that," she moaned, as she began flexing her ass up to meet my hard strokes, which made me somehow reach new depths that seemed to break the laws of physics. "Remember I have this house to myself all summer."

"I'm yours," I moaned, yes, 'moaning' being the operative word here; we were both moaning loudly and constantly. The pleasure was beginning to make my balls bubble for the second time in half an hour.

"Oh fuck, fuck, shit, yes, don't stop for an instant you mother fucking stud!" She ordered, strongly bucking her ass up to meet my strokes. "Fuck me like you want to fuck your mother, you dirty mother fucking stud."

Instantly I imagined exactly that... fucking my Mom... something I never had considered to be more than a silly boy fantasy... although the idea of fucking Kendra had also been something that I thought had zero percent chance of ever happening.

"Oh yeah, you want to fuck your Mommy, don't you?" she asked nastily, making this hot moment somehow hotter. She was growling at me now. "Tell me, you mother fucker, tell me what you want to do to your hot Mommy slut."

So drawn into the moment, so drawn into the lust, so drawn into my vivid visualisation of my greatest fantasy, as I kept fucking her as hard as I could, I shouted as loud as possible, "Yes, I want to fuck the hell out of my mother and make her my three hole cum bucket."

"Holy shit, you are a nasty mother fucker," she smiled approvingly, as she quickly shoved me out of her and rolled over onto all fours. "Now come and really pound my cunt."

I quickly jumped behind her and slammed back into her with all my strength as I gave an order of my own. "You got it, bitch. Now tell me what you want."

"I want a full time stud to be at my beck and call," she moaned, bouncing back on my cock. "I want that stud to be you." After a few seconds of her bouncing on my cock while I bounced it forward as deep as I could get it, she added, "I also wouldn't mind seeing you ream your mother's asshole while she buries her face in my cunt."

"Oh fuck," I groaned, my picture of that description instantly flooding the entire room.

"You really want to be a mother fucker, don't you!" she moaned, clearly close.

"And a MILF fucker," I added, grabbing her bodily, pushing her shoulders down and angling her ass up to really penetrate her... a position I recalled from a video I had watched recently.

"Oh yes, use me, you fucking stud," she demanded, as I fucked her as hard as I could.

"Fuck yes, pound me, fuck me, make me your slut," she babbled before screaming a couple strokes later, "Yesssssssssss!"

I kept fucking her as her orgasm cascaded through her, knowing I was pretty close too.

After a few more strokes, I knew I was very close and wasn't sure where to cum. I warned, "I'm not going to last much longer."

"Come in my cunt," she demanded. "I want to feel that load shooting deep inside me."

Permission granted, I let go and as my next forward thrust arrived deep inside her funnel of warmth I shot my second load in half an hour as far inside her as it could possibly go.

"Oh yes, fill my cunt with your cum," she moaned, looking back directly into my eyes with a mixture of lust and euphoria.

I hope I looked the same as I kept spewing my cum deep inside, now having experienced two similar, but different orgasms... the difference between coming into a mouth versus into a pussy was subtly different, yet similar... and both were amazing.

She rolled away from me and onto her back and gave me a big, satisfied grin. "For a virgin you sure can fuck!"

"I think I make up for my lack of experience with eagerness and an abundance of enthusiasm," I joked as I admired her big tits. "And lots of research online."

"I especially like your eagerness and enthusiasm: both of those things," she smiled.

"And I like both of those," I said, openly admiring her tits, pretty proud of my smoothness.

"You do, do you?" she smiled wickedly, confident of the spell she had over me. "You haven't even seen them yet, have you? I've been told they're pretty nice." She finally removed her bra and cupped her hands beneath the twin beauties, offering them up.

My fickle blood abandoned my head once again and I felt suddenly exhausted, as if every ounce of energy had been sapped out of me... suddenly realizing how Superman must feel when he falls prey to kryptonite... I wavered, almost collapsing on top of her.

"If you want to bury your face between my tits, go ahead," she offered. "They're still as neglected as my cunt was a few minutes ago."

I instantly buried my face between her luscious tits, finding yet another heaven this afternoon.