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Lucky Leap Day

Category: Mature
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There must be something inherently lucky about February 29–leap day.

That’s the day I went to get my hair cut by the gal Carla who’s been cutting my hair for over a year. She does an excellent job and has an interesting personality, so I always wait for her. To tell you the truth, I originally selected her because she’s good looking.

Anyway, the place was extremely busy, and I had to wait a long time for Carla. With all the magazines taken, I had nothing to do but gaze at the receptionist, a to-die-for gal who looked to be only 18 or so–a long-legged slender girl with a picture-perfect ass stuffed in skin-tight jeans, luxuriant shiny brown hair to her waist, big, pendulous breasts beneath her thin turtleneck sweater, and a beaming smile on a beautiful young face. Definitely a 10. Her name tag said “Ashley.”

When I first checked in, she paid me no mind–didn’t even give me a second look. In fact, why would anyone give me a second look that day? I looked like crap: Not having showered or shaved, with spatters of oil on my dingy tee-shirt from changing the oil in my car earlier, I was far from my usual well-dressed, well coifed self. And I was old enough to be her dad.

I was the very last customer of the day, and as the crowd thinned, I struck up a conversation with Ashley. She was reading a magazine, glued to an article in it. I was standing across the counter from her and asked her what it was she seemed so interested in. She said she was reading an article.

“What’s it about?”


“What kind of sex?”

“Sex with an older man.”

Hmmmm. If there was ever a long shot, Ashley was it, but this magazine article may have opened up an opportunity, be it a remote one. Probably an article written by a horny older dude, like me, I surmised. I asked her to tell me more about the article. “It says a young girl should experience an older man at least once in her life because they are more patient and creative and interested in the woman’s pleasure.”

“That very well may be true. I don’t know about other middle-aged men, but that certainly describes me.”

“Really, now?” she rejoined, with an apparent interest. We went on to another subject, but Ashley was looking back at me a lot more now, maybe even flirting, as she seemed to be veritably posing–sticking her fine butt out way more than necessary and squeezing her big boobs together with her upper arms. Was it just my imagination that her nipples were more visible now than before?

I pictured myself banging her doggie over that counter, she sucking me while I sat on it, and titty-fucking her while she gazed at me with those big brown eyes. I chuckled to myself when I recalled the advice of a sports psychologist who said you must repeatedly visualize the activity to make it more likely to come to pass.

Finally, Carla was ready to cut my hair, so I sat in her chair while talking with her and keeping my eyes on Ashley in the mirror. This did not go unnoticed by Carla, and she commented that my attention seemed to be riveted on Ashley.

I asked Carla about her and what she thought my chances were. Carla said Ashley had recently broken up with her boyfriend and that I should “go for it.” In a little while, Carla walked over to Ashley and said something to her I could not hear. Was she putting in a good word for me or telling her to beware of the dirty old man?

When Carla finished my hair, the only people left in there were she, Ashley, and I, and it was closing time. I was trying to craft the right words to make a play for Ashley when the Papa John’s Pizza delivery guy knocked at the now-locked front door.

Apparently, someone had been pulling the old practical joke of sending a pizza to a place that didn’t order it, and the guy was pissed. It was 6 o’clock and I was hungry, so I asked the girls if they wanted to buy it anyway and split it. Carla said she had dinner plans with her boyfriend, so I asked Ashley if she’d like to share it with me.

“That’s a great idea,” she said, I hardly believing my ears. “I’m famished, but we’re closed, and we gotta get out of here. I’m driving that white Integra out there, so follow behind me and we’ll eat it at my place. OK?”

Well, I didn’t have to think about that invitation, so I bird-dogged her in my car, running a couple of “pink” traffic lights to keep up. Was she in a hurry to get naked or was she trying to lose me?

We drive for several miles and she turns into a very upper crust neighborhood and wheels into the driveway of a large, expensive home. Parked under the carport were a big Benz and an Escalade. Obviously, her “place” was also her parent’s place, and I was momentarily dejected at the notion of meeting a mom and dad who were quite possibly younger than me. And the Ducks Unlimited sticker on the luxury SUV suggested he owned a Benelli 12 gauge with which her dad might enjoy splattering my brains.

She unlocked the back door as I followed her into the kitchen with the pizza. “My folks are on a cruise, and my sister won’t be back until around eight, so we’ve got the place all to ourselves,” Ashley said, smiling wide and striking her sexiest pose. I could not have received a go-ahead more clearly if the letters FUCK ME NOW had been inscribed on her teeth. I felt like a ton of bricks had been lifted from my shoulders, and, giddy with relief, I just blurted, “Let’s eat naked, shall we?”

“Kinda kinky, huh?” she smiled. “And another great idea!” And without a moment’s hesitation, she kicked off her shoes, pulled the turtleneck off over her head, wriggled out of her jeans, and stood there in sock feet smiling in sheer panties and bra. I literally pinched myself to make sure I was not dreaming.

I followed suit, stripping down to my boxer briefs and socks. “I’d like YOU to take off my undies, and I’D like to take yours off myself,” she said. That seemed like a fair deal to me, so I walked over to her to do just that.

She gently rolled my shorts off, and blew her warm breath on my cock and balls as she bent down to remove my socks. Then she stood upright, smiled, and presented herself for underwear removal. I picked her up by her slim waist and sat her on the kitchen counter.

I unfastened her 3-hook bra and slowly pulled it off her shoulders. Soft, pliable, heavy D-cup breasts spilled out. Her dark red nipples, pointing slightly upwards from the half-dollar size areolas, pointed up even harder in the cool kitchen air. Oh my god, these boobs were nice! I squeezed them, circled each nipple once with my tongue, and kissed them hello and, temporarily, good-bye.

“I have very, very sensitive nipples, so thanks for being so gentle. That article was right,” Ashley said. I must find out who that author is and send him a generous donation, I noted to myself.

With great restraint, I left the nipples and moved downward, but I detoured the pubic racing stripe visible through the sheer panties, deciding to leave the best for last, and rolled off her socks, revealing the slimmest, softest arched feet, with extra long toes, I’ve ever seen and felt. I ran my thumbs firmly up her arch from heel to ball, and softly kissed each toe. Exquisite!

Then I smoothed my palms slowly up her silky soft slender legs up to her panties and blew my hot breath through the material right into her warm crotch in a long exhale. She inhaled suddenly and deeply, and I smelled the wonderful aroma of her pussy, the moisture of which began to print through the thin fabric.

As I hooked my fingers into the panties, she stiff-armed herself up off the counter so that I could easily slip them off her buns and down her legs. Then, she leaned back against the cabinet, pulled her feet up to the edge of the countertop, spread her legs wide, and reached beneath her buns to pull her pussy wide open. Nobody could say Ashley was shy.

The thin stripe of hair on her mons pointed like an arrow at the glistening exposed clit centered over dark red, engorged pussy lips. Drops of juice dripped down the middle onto the counter. She smoothed her delicate long fingers upward along the inner surface of those pussy lips until they brushed across her love button.

“I just shaved this morning,” she said through open lips, her eyelids at a sultry half-mast.

I circled her tiny anus once with my tongue and slowly licked up between her pussy lips before pausing to suck her clit with an intentionally loud slurp. She quivered and pushed her crotch firmly back against my mouth, signaling to do that some more. I continued my oral ministrations, enjoying her beautiful bare twat in its own right, and the extra-juicy libations were a double bonus in that they quenched my considerable thirst. Perhaps Ozarka could offer this in a five-gallon bottle for the office. I licked and sucked her pretty young pussy and clit until I counted three quivering orgasms, a little one, a medium one, and a much bigger one. That should do it for now.

I disengaged her pussy, picked her up, and planted her standing on the floor facing me. As I closed my eyes to kiss her so-soft facial lips, she plunged a lengthy and agile tongue into my mouth to swirl sensuously in a dance with my own tongue. What a wonderful kisser Ashley was!

My hard cock snapped up right between her legs against her hot and wet pussy lips. In a flash, she wrapped her arms around my neck and legs around my hips and impaled herself to the hilt on my raging erection as she gasped for air, breasts heaving against my chest.

“Let’s not rush this now, Ashley. Let’s eat that pizza before it’s stone cold. We’ve got plenty of time.” “Exactly like the article,” she said, opening the box and feeding me a big slice.

In truth, the pie was already cold, but it was undoubtedly the best pizza I ever had. I mean, there I was nude sporting a boner in the kitchen with a naked young horny 10 with rigid nipples pointed toward Mars and juice dripping down her thighs from a freshly shaved pussy. Pizza does not get any better than that, folks.

In fact, we really did NOT have much time–about an hour as it was almost seven and her sister would be returning around eight–so I scarfed a fourth piece of pizza and washed it down with a Diet Coke we shared.

Ashley got back on the counter in the same position she was before, only this time she pushed her glorious breasts together between her thighs pressed firmly against her chest, creating deep cleavage, as I ate her pussy and asshole with delight while she moaned and ran her slender fingers through my freshly cut hair.

I would occasionally turn north to suckle her very sensitive nipples while keeping my fingers busy on her twat. So many excellent parts, so little time. She kept using her legs to pull me into her, and so, though I could have eaten her ’til kingdom come, I knew she needed ye old meat in the hole.

So we fucked–first missionary with her ass on the edge of the counter and me standing on my tip toes on the floor, hands on the ankles of her legs bent up and back against the cabinets. Ashley’s pussy was just the right size for me—not too tight and not too loose—but sopping wet and just gorgeous to behold as I watched myself go in and out of her. She did not have a lot to say, but once in a while she’d puncture our heavy breathing with a “good dick,” “that’s it,” or “oh, yes.” It’s always nice to get favorable feedback.

Then she hopped onto me, like before, in a flying fuck position. I must say, she could do it in this awkward-for-most position better than any other girl I’ve ever done. She knew just how to center her I’d guess 120-pound weight on me and keep our collective balance while coordinating her thrusts with my rocking pelvis, she in control with a perfect mid-speed screw. All the while, she alternately kissed my lips, neck, shoulders, and tongued my ears. When she’d cum—and she did several times—her eyes would nearly close as her lips pursed out and her whole body would shiver like a person reacting to extreme cold. But Ashley was anything but cold, and this was obviously her favorite position.

Even so, with my hands on her firm butt most of the time, I got ever eager to look at that fine ass, so I steered her over to the other side of the kitchen, turned her round, and bent her forward. She pooched that ass out just as she had at the salon, and I did her doggie. What a marvelous derrière!!! Smooth, supple, and all muscle, rippling in little waves with each bang. No passive lover was she, as she rocked backwards in time to my forward thrusts, making a rhythmic and raspy “ugh, ugh, ugh,” amplified by the stainless steel sink her head hung over.

Now I’m not into intense pain, either giving or receiving, but if ever there was a spankable ass, it was Ashley’s, and I felt I would be remiss if I did not at least give it a couple smacks to see if she liked it. So as I continued the rhythmic banging, I slapped her right bun with an open hand. “Oh, yeah,” was her immediate response, so I smacked her left bun with my other hand. “Just a little harder,” she requested as she sped up the fuck pace a little. Smack, smack, smack, smack I played her buns like bongo drums, turning her buns pink.

Zany mind that I have, I pictured myself as Rikki Ricardo playing those bun drums. “Lucy, you got some splaining to do,” I joked. Though Ashley was less than half my age, she started laughing: Just about everyone is familiar with the old I Love Lucy show. Then I broke out into my imitation of him singing the Cuban classic Babalu, still playing her ass like drums. At that point we were laughing so hard that our fucking slowed considerably, though a good time was being had by all, as the saying goes. “You are insane,” she commented, correctly.

I pulled her long, soft brown hair into my hands and combed my fingers through it, smelled its fresh scent, and buried my face in its luxuriant thickness. She should do TV ads for shampoo, I thought, only her boobs might distract from the hair. I twisted it into a loose rope, making a brush with the end, which I used to tickle her anus. “Oh, I like, I like, I like. Keep doing that,” she instructed. And so I did, noting the goose bumps that pricked up across her buns and the changing patterns of tiny wrinkles on her brown hole.

Perhaps I would revisit this area a little later, but I felt her neglected breasts needed attention at the moment.

Those beautiful, pendulous breasts were hanging down like two big bell clappers, swaying to and fro with our fucking. They looked absolutely great hanging so far down like that, and they seemed to move in almost slow motion. I cupped them lightly from below, and let the hard nipples skid across my palms. “Good,” she said, reaching back to tickle my balls as she looked over her shoulder to check my reaction, which was one of pure sexual pleasure, so she continued the scrotal play.

She had exuded so much pussy juice by this point that her whole bottom was wet, or, to be more precise, her bottom hole was wet. Still thrusting methodically in and out of her pussy, I eased the tip of my thumb into that super-tight bottom hole. “Yeah,” she said, as it relaxed a little. I carefully rotated it back and forth and slipped it in past the first knuckle. “It’s OK. I like that, but go slow.” I wiggled my thumb some more and gradually worked it in up over the 2nd knuckle, then quivered it rapidly inside her as I fucked her pussy a bit faster.

Ashley’s fair skin began to flush, then with a long, rising “ooooooOOOOOOOOOOOO” crescendo and her whole body vibrating, she thrust back hard, sending my cock and thumb deeper than ever into her respective orifi, and she just clamped down both like a vice. “I’m cumming. I’m cumming. I cumming. I’m cumming,” she must have said forty times. Had she not been able to clamp her pussy so tight around the base of my shaft, I would surely have cum, too, and I was glad I didn’t, for I had other “plans de orgasma.”

I do dearly love to make a woman cum, and Ashley had cum quite a few times, this last time being the Mother Of All Orgasms, so I was as happy as could be. I laughed out loud, remembering all the positions I’d fantasized about with her back at the salon, and that sports psychologist’s advice—correct as it had turned out—about the efficacy of the visualization technique!

“What’s so funny?” Ashley asked, still breathing hard from the Big O, and looking over her shoulder as she arched her back even more dramatically to look at my dick and thumb still buried in her holes. I answered, “Oh, I was just thinking about…” Fucking me in the ass?” she interrupted. “Listen, I liked my old boyfriend doing that, and that vibe thing you did with your thumb is great, but you’ve got a monster penis compared to him, so I dunno.”

He must have had a pencil dick, for my 7-inch-long, 2 & 1/2-inch-thick dick is nowhere near monstrous proportions. “‘Monster penis,’ eh? Flattery will get you everywhere, Ashley, but let’s not get hung up on buttfucking—today, anyway.” “I’m not saying I WON’T do it,” she backpedaled. “Relax, girl, we’re here to have maximum pleasure. Fuhgedaboudid.”

“Then, will you please let me suck your dick?” she asked. Like I was going to say “no” when she asked so nicely! She pulled up the 3-step ladder stool and sat on the edge while I stood there and fed her my meat. Damn! Ashley was a black belt when it came to giving head, paying careful attention to my balls by sucking and licking them while stroking my shaft up and down with both hands.

Gradually, she took me ever deeper into her mouth, putting her agile tongue to good use while tickling my balls with the tips of her immaculately manicured fingernails. She would alternate between worshipping my rod with her eyes as it popped out of her mouth while she licked it up and down, and looking straight into mine while she sucked it all the way up and all the way down. I almost came a half dozen times but managed to somehow choke back.

Ashley’s boobs were just made for titty-fucking, and I could not let the opportunity pass. So, while she was still sucking me so expertly, I spotted a bottle of extra virgin olive oil on the counter behind me and retrieved it with my long arms.

Withdrawing my penis from her mouth, I kissed her lips and face and ears and breasts for several minutes before pouring the oil all over those magnificent mammaries and massaging it in good.

“Are you going to make love to my boobs?” “Indeed,” I replied, “And, with your kind permission, I would like to cum between them and de-virginize this oil.” “Oh, I just love that,” she said, laughing and squeezing them tightly around my aching shaft, working them expertly up and down as I gently twiddled her hard, oily nipples between thumb and forefinger.

Ashley was one of those rare girls who can cum from breast stimulation alone, and apparently I was doing the trick, as she orgasmed two more times. As she came the second time, she squeezed her boobs very tightly together around me, and I let him rip, blasting a rope of cum up onto her lips, chin, and neck. She never even blinked.

On cue, she used her hands to milk the subsequent spurts right onto her breasts, rubbing the underside of my cock against her slippery, rubbery nipples until every drop of my man-goo was expended. To say that was a terrific climax would be the understatement of the century.

She licked the cum off her lips. “Mmm. Tastes great.” “Less filling,” I joked, borrowing from the Miller Light commercials.

I looked at my watch. Oh, shit, just a couple minutes before eight. I wiped the olive oil off my still 3/4-hard cock with a paper towel and jumped back into my scruffy change-the-oil-in-my-car clothes and gave her a good-bye kiss, cum still dripping from her chin and all over her neck and boobs and running down her tummy into her crotch.

“I’d really like to do this some more,” she said, “but my parents would totally freak if they knew I was seeing an, um, ‘man’ like you. You know you can find me at the shop, though.”

I told her I understood, and gave her another kiss and a friendly, “Glad you read that article.” “Me, too!” she said, not exactly rushing me out the door, despite the time. Now, to be honest, most women do not look their best when they are as Ashley was—just having had the shit fucked out of her, hair matted with olive oil and cum, and naked body drenched in them, especially under florescent kitchen lights—but I drank in one long parting look at her, and she was still a solid 10. I gave her a parting kiss, which she turned into a French kiss, before I broke it off with an open-handed smack on her butt and ran to my car. She stood there naked in the threshold of the door and watched me back down the driveway. “I owe you one!” she hollered, bending over and pointing a finger at her butthole.

I got headed out by going around the circle drive in front. As I pulled out into the street, there was a Civic just making a right into her drive, and I got a good look at the driver. She was the spitting image of Ashley, and had to be her sister, apparently her twin sister!

I wondered if she, too, had read that same article. Or maybe another one about twins doing a menage a trois. Perhaps I should have stayed a little longer to find out. After all, February 29th had already proven to be an awfully lucky leap day.

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