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Foot In The Door

A typical teen aged boy learns some valuable lessons from a not so typical, older single mother…

She did not know I was watching. She did not know I could see. But I could. There it was; right fucking there. I could not believe my eyes.

There is something mesmerizing about seeing your first naked, live and in person, vagina. It is both mysterious and shocking. It is not like the first time you see a picture of one in a glossy magazine, or the first time you see one in action on the VHS tape you and your buddies rented and watched on the VCR back in the 1980's. Seeing a real life woman’s vagina is fascinating, because it is real.

It is like happening upon a car crash before the emergency services arrive. You know it just happened. You do not know what caused it, but you are now witnessing the immediate aftermath of someone's actions. You almost feel privileged to be the one, or one of the first to see it, but with that privilege comes great responsibility.

Do you call 911? Do you stop to assist? Or do you slow down, pretending you are concerned, while you look for carnage? Do you secretly hope that you will have a morbid story to tell? Do you convince yourself that those other people will help so you do not need to, and you just drive by? Will you be somewhat relieved, yet disappointed, that no one is maimed or injured? Whatever the action or reaction, you stare, with your intrigue affixed to the first shiny or glistening object that grabs your attention.

With your first vagina, your eyes widen in disbelief and your eye brows uncomfortably raise, your heart races and your body uncontrollably perspires, you feel your cheeks tense from your ear-to-ear smile, and then it becomes difficult to breath.

You become paranoid because you now have seen something you were maybe not yet supposed to have seen and you hoped like hell no one catches you looking. It takes a few moments longer to realize the tension around your groin, but you are pleased with that reaction. You feel confident that if, and or when, you are called into action, your burgeoning manhood will meet the challenge.

To a young man, it can be somewhat confusing, and yet life affirming, but you never ever forget your first.

She was a friend of a friend of the family's. She had been invited to a barbecue, not a special occasion, just an outdoor summer dinner for family and a few friends. She and her children were visiting her friend as they passed through during their summer vacation.

Divorced and openly admitting she was glad to be, Cathy was a pleasant lady that my parents seemed to be quite fond of. Mom's friend had commented that Cathy was staying with her before continuing on her way to Yosemite. She and her kids were only in town for a couple of days, but Mom insisted Carol and her family join us, as Mom would demand of any friend of a friend. They too seemed to have a connected past.

We all sat or lounged around on our deck while my Dad tended to the barbecue. The handful of adults conversed across from me, while I took in some rays, trying to add some color to my pasty white, undeveloped teen body. It was either that or play with her kids. I was saving that as a last resort retreat from potentially being engaged by embarrassing drunken adults.

Cathy sat up while straddling the chaise lounge, and I sat across and a little to her left. On this hot day that it was, light clothing was worn by all, me shirtless and only in shorts, and Cathy in a cotton tank top, which I could on occasion, see her bra straps peak out from under the tank's shoulder straps.

As I listened to Van Halen on my Sony Walkman, since I was neither engaged nor interested in the adult's conversations, I watched those indulging adults make fools of themselves. The sound track to my mid-1980’s seemed apropos for their outlandish behavior. They all laughed and hugged and pretended to be people they were not. I thought all that was missing was some cocaine. Mom said that some day, as an adult, I would behave the same way.

What-EVerrr, Mom!

As if!

My attention then turned to Cathy as she shifted on the chaise and kicked off her flip flops. I then noticed that that action had caused her shorts to ride up and open, providing me with a clear view of where light met dark.

At first, I was uncertain what I saw, but I knew panties did not look like that. It was hair, short curly dark hair, even darker than her straight, shoulder length hair that she had pulled back into a pony tail.

I wondered why her secret hair was curly and not straight. Would she need to cut it on a regular basis? If not, would her vagina look like a yak or one of those exotic looking cows that has long hair covering its eyes? I concluded that was not the case. I had never seen pictures like that, nor had any of my more so-called experienced friends mention it. I could be wrong, but until proven otherwise, I will assume my working theory was correct.

Directly beneath her curly pubic hair, were the wavy folds of her vagina, labia I believe they were called. Somewhere between them, was her opening that penises went in and babies came out. Somehow, pee came out of there too, but not until many embarrassing years later, did I learn how that worked. When your girlfriend, while on vacation, gets a UTI, and it becomes so painful you need to rush her to the hospital, you quickly and unceremoniously learn where girl pee comes out. I still can not believe I did not figure that out on my own.

Thank Tom Cruise I was wearing sunglasses!

I glanced at the adults to ensure no one was watching me, and was praying Cathy would not shift positions or move to another seat. My prayers were temporarily answered and through my mirrored, Top Gun aviator glasses, I stared, trying to imagine what it felt like. Were her folds soft and spongy like my ear lobes, or were they firmer, more cartilaginous like the end of my nose? Did they engorge with blood and become aroused, like a penis, or were they just loose, floppy pieces of meat, like oversized skin tags? I had so many questions.

Clitoris? What the hell is a clitoris?

Again, this was something I embarrassing learned about from a girlfriend, and I learned about the g-spot from yet another gal, but that was not until my second year of college. Back then, I was fairly certain most women did not even know about the g-spot or what it does, until their teens were well behind them. And certainly, most guys did not have a clue what it was or where to find it, ever. Well, I recall hearing my Mom and a few girlfriends one time saying that, but at the time, I had no idea what they were talking about anyway. Her case in point.

Things got out of hand when my brain told my penis to take a peak. I had contained the little buggar during my pervy peeping time, but while I was preoccupied imagining Carol on top of me, straddling me, riding me like a bucking bronco, my penis snuck its way into one of my short's leg openings, stopping short of the seam and leered out. I noticed this potentially embarrassing situation the same time Carol looked at me, paused, and then returned to the adult conversation. She then nonchalantly turned her body, bringing her legs and feet together, on the other side of her chaise, facing away from me.

I swore I heard my penis say to my testicles, "Sorry boys, show's over!"


For the next thirty million minutes, I sat in sheer terror wondering if Carol knew I was peeping at her pussy, and more worrisome, if she had seen my hard on. If she did, my biggest fear was that she would say something to my Mom's and her mutual friend, or worse; she would tell my parents about their perverted son. At that point, I wanted to crawl under a rock and die. However, something told me, one thought of that dark, hairy wonder that I saw between Carol's legs and my pecker would push that rock off of us, saving both his and my life, thus enabling us to be subjected to more of life’s embarrassing moments and ridicule.

At dinner, we squeezed around the large table my Dad had painstakingly constructed many years ago. I was certain we would hear that story again for the billionth time. If no one commented on the size or his handiwork, my Mom would bring it up so they would.

Again, Carol and I sat across from one another. I was nervous as hell, but from what I could tell, she said nothing to her friend or my parents. This was good. Things were going well. I focused on my food and less on the inane grown-up chatter. My mind wandered and I wondered what David Lee Roth would do in my situation. I had a pretty good idea, but I was no DLR.

When one of Carol's kids dropped their fork, with it landing what I thought near me after it hit my shin, I volunteered to retrieve it. I bent over sideways and saw the fork closer to Carol's foot than mine. Since she and I were not on speaking terms, more so because of my shyness, I made the decision to go under instead of suggesting she pick it up.

When under the table and as soon as I reached the fork, I saw the same thing I had seen before, but this time, up close and very personal. However, I felt we needed to be properly introduced and first see if we had anything in common, before I used any of my moves.

Yes, it scared the bejesus out of me.

To my surprise, Carol pulled aside her shorts and parted her thighs, and I now saw what I had been searching for since before the first time my voice squeaked and cracked. I was near certain that her labia were spongy but I did not expect them to be glossy too. Yes, another thing I would later learn about how that worked, from my first girlfriend. While staring at Carol's glistening vagina, I heard her say my name but not what she had said. However, I definitely heard my mother's reply.

"Yes, Jamie is a good boy," she giggled under her breathe, and then whispered, "He's just waiting for the right girl."

Fuck!!! That's Mom code for, Our boy is still a virgin.

I wanted to crawl away! I was already on my hands and knees. No one would miss me.

Ugh! Mom, how could you embarrass me like that?

I am certain if I had said that, my Dad would have responded something like, “That’s what parents are for, son.” Everyone would then have a belly giggle at my expense. Jerk offs.

After returning to my seat and wiping clean the fallen fork, I returned it to the kid. No thank you from him but an appreciative thank you from Carol. Her gaze got the better of me and I had to look at my food.

Her eyes asked if I liked what I saw. My blushing face and penis confirmed that I did. Dinner continued uneventful except for the searing ache in my balls. I knew I had to release them sooner or later, so I chose sooner, because I could not concentrate on anything else.

With a deck full of intoxicated adults, I decided to deal with my situation in the basement bathroom. I did not bother to excuse myself from the table, only saying that I would be right back. Even though I was going to jack off in the bathroom to the thought of one of our guests, I knew my mother would see no need for me to be rude about leaving the table. I then excused myself and left.

As I closed the bathroom door, that same foot that discarded the flip flop, was now preventing the door from closing. My first reaction was to apologize, hoping I did not injure her. My second reaction was sheer panic. Carol pushed open the door and then locked it behind her. She looked at me in a way I have not witnessed before.

Super. Instant. Hard On. Erection.

How does my body know these things?

"Did you like what you saw?" her pert mouth repeated what her eyes had asked before.

I started stuttering a response but her finger hushed my nervous lips.

"A reliable source tells me that you are still a virgin. Not many sixteen-year-old virgins around these days," she playfully mocked me.

I was speechless but before I attempted to respond again, she interjected.

"No, I'm not going to fuck you," she paused, "Today.”

In my mind, I heard a laugh track from the television show, Happy Days, and a collective and sympathetic, Awww from the audience.

“However, I do want to see you cum." This time, the audience cheered.

I still remember what Carol smelled like. It was like vanilla and flowers and...

Wait. What?

With my scared but dejected mind wandering, I had missed that last part.

"I want to watch you," she said. "I want to watch you stroke your cock and cum all over your hand."

This felt, for lack of a better word, unusual.

Then, for the first time since my mother and my doctor, a person with breasts touched my groin. I said nothing, giddy as fucking hell, I indeed said nothing, as she untied the draw string to my shorts and then pulled them over and down past my erection. My pecker stood straight out at her and I can still hear what she said.

" Yummy."

I took that as a compliment. Her smile confirmed that I should.

"We don't have a lot of time, so show me how you stroke it. Go ahead, Jamie, please."

Never had I beat my meat for, or in front of, a woman. Somehow, we seemed way past the point of me denying that I had ever masturbated, so I grabbed my shaft and started yanking on it as fast as I could.

"Whoa! Whoa!" she laughed. "Slow down before you hurt someone. Nice and slow, long strokes, like you are making love to a woman."

Little did I know then, but Carol gave me my very first lesson on how to properly treat a lady. Learn to make love first, then fucking later.

She watched intently as I slowed my pace, doing exactly as she instructed.

Nice and slow see, that's the way to do it. Nice and slow.

That time, I heard speaking some burglar character type from the show, The Flintstones.

Damn wandering, tangential mind.

Carol licked her lips as from out the tip of my penis oozed a large drop of pre-cum. I watched in extreme excitement, as her finger slowly move toward, and then brushed against the tip, removing my gooey, pearly gift.

She again cooed yummy as she brought the droplet of my man juice to her pointed, inflamed tongue. That action generated the first meaningful twitch in my balls. That very naughty smile of hers, as she swallowed that gift, brought the second.

"You should use lotion," she started to advise, but then interrupted herself, "Or better yet, baby oil."

She grabbed the bottle out of the mirrored vanity that she had just opened. Carol poured some over my fingers and watched as I worked the scented oil into the skin of my shaft.

"Baby oil closely resembles the feel and viscosity of a woman's pussy, but not the smell," she informed. "But NOT the smell," she repeated, feeling the need to do so.

It did not matter. Carol had inadvertently imprinted upon me the association of baby oil and sex. After that, whenever I smelled baby oil, I felt a twitch in my trunks. I had hoped that association would fade and eventually go away, but it never did.

"As you stroke your Kkock... " Oh, I did love how she said that. "The friction from your moving hand will warm the oil, and in turn, warm the skin on your Kkock."

She was right. It did. Both things.

"What you are now feeling, is what it feels like inside the walls of a woman," her evil, taunting voice informed.

Carol then lowered her shorts, exposing her trimmed muffin. I dare not call it that because it sounded funny, so in my mind, I kept to the correct medical term of vagina. Since we were barely on speaking terms, I did not think pussy was appropriate either.

I stared as Carol ran her fingers through her dark fur, before she used both hands to part her labia and expose her fabulous delta. Yes, the area that I did not know then, but now do, which hides and contains the clitoris. It was fascinating, and it also looked as if she too had poured some baby oil over her genitals.

Carol never asked because she knew the answer, and I soon answered one of my earlier questions.

Ear lobes. Soft, wavy earlobes with little ridges, like large fingerprints.

Pussy prints? Nah.

I continued to stroke slow and long, as she guided my fingers over her lovely labia, all the way to the back end of her vagina. She held them there and gave me and my penis our second lesson.

"Jamie, the entrance is back here, not up front."

She then pressed my finger tips inside, and I felt for the first time, the slippery warmth of the insides of a woman. I was ready to blow.

"Baby boy, remember that your first time, okay?"

I eeked out an okay just as she gave me my first taste of womanly nectar. I savored her scent and flavor as she lowered herself to the fuzzy mat on the bathroom floor. She then licked the second pearly drop from the end of my dick.

"Now, this is very important. When you are ready to cum, tell me. When at a party, a girl doesn't want to wash cum off of her face. She'll then need to reapply her makeup. Same goes for cum in her hair. Just remember, when you are ready to cum, tell her."

"I'm cumming," I grimaced as Carol's mouth immediately attached to the knob of my penis, giggling as her lips locked along the shaft just after the bulbous head. I came so much I felt like I was peeing in her mouth, but I was not, thankfully. That would have been bad, I suspect.

I felt my body rapidly twitch and blindly, I enjoyed the pleasure that was my first orgasm with a girl. When I heard Carol swallow, I opened my eyes to her hers now closed, and the action of her constricting throat. Her one hand now overlapped mine as her other hand vigorously worked between her legs, rubbing herself into a frenzy.

Her tongue began swirling around the smooth head of my penis, while she squeezed my shaft. Unsure what to do, I removed my hand so she could grip me on her own. I stood and watched this amazing thing happen that I have only before, seen in pictures or on video.

When she started to tremble, and her tongue stopped swirling, I thought that Carol must be having an orgasm. I was correct and I took notes. Carol made whimper-like noises as she came, which she muffled by forcing my penis deeper in her mouth. I watched in awe as this woman, at least fifteen years older than me, climaxed at my feet. I had nothing to do with it, but I still felt I contributed in some small way.

After we cleaned ourselves, Carol told me to return to the table first, and then she would follow shortly behind me. After I sat down, and then Carol, my Mom looked at me, then Carol, and then my Dad. Her motherly suspicion sent shivers down my spine, but that was only my perception. Mom was tipsy and returned to the conversation with the grand, hostess smile that she had worn all day.

Carol returned to her kids with an offer of more food and drink, which they both accepted and denied. Her foot then found the leg hole than my inquisitive penis had before been spying on her from. Carol's toes greeted my balls, including her big one squirming its way inside my ass. She then curled her toes around my shaft and massaged my engorged cock, just as Mom served her famous, strawberry shortcake dessert. Shortly after that, Carol and I returned to the bathroom where we both had a second helping.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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