I couldn’t keep my eyes off of the elegant older woman sitting in the top row of the bleachers at the matinee of the ritzy horse fair.
I also couldn’t help but notice that she was making a less than subtle production out of lowering her designer sunglasses and looking me up and down, smiling in a cat-that-wants-to-swallow-the-canary way. Younger women, or at least women who were my age, didn’t begin to know how to smile like that.
The fact that I guessed our ages to be at least twenty years apart did nothing to diminish the palpable chemistry with the impromptu Mrs. Robinson, even from afar. I was reveling in the fact that she was overtly flirting with me, and behind my girlfriend’s back. That made it more wickedly exciting, but I didn’t expect it to be anything more than it was, harmless flirting with a lady old enough to be my mother.
But, oh, so fucking sexy, in a classy, though coquettishly slutty way. She seemed to look right through me, and I could feel my loins stir as I became legitimately aroused by her brazen staring.
I was diverted from my surreptitious gazing by a nudge and a question by my twenty-three-year-old college sweetheart, Stephanie, who was standing next to me along the railing of the horse ring in the Main Line section of Pennsylvania, home in every May to one of the longest standing traditions in the equestrian world, the Devon Horse Show.
“I said I’m going to get a cotton candy, do you want anything?” Steph tried to follow the direction of my eyes, to no avail, as I quickly turned back to the show. “And what are you looking at, anyway? The horses are over here.”
I smiled at Steph and rubbed that spot on the bottom of her backbone that literally made her purr, like clockwork. “I’m fine, baby, nothing for me. Just enjoying the blue sky. You go on ahead, I’ll wait here, OK?”
Out of habit, I gave Stephanie a twenty, even though I was struggling for every dollar and Stephanie was the eldest daughter of a Fortune 500 company’s top executives.
Steph never seemed to grasp that every once in a while, it might be nice for her to come out of pocket to pay for an event here, a dinner there, a movie every now and then. She had everything handed to her on a silver platter throughout her life.
Me? I was trying to find a better job than my current gig as a landscaping account representative, after having recently been cut by the Cincinnati Reds organization after two years of playing minor league ball in their organization.
Ya know how some armchair athletes recant their glory days, and chalk up the end of their careers to an injury or some other act outside of their control? Well, my sports demise was much more simplistic. I couldn’t hit the curve ball.
So, here I was, at age twenty-four, trying to literally decide what I wanted to be when I grew up. I could marry for money, I thought, watching Stephanie disappear into the crowd of fair-goer patrons.
But truth be told, as pretty and aristocratic and wealthy as she was, Steph bored me silly, especially in the bedroom. I was true to her during my brief albeit nomadic baseball career, but had to admit to myself that perhaps that was a mistake.
I sighed inwardly and was still lamenting my fate when I heard the husky though alluring feminine voice just behind me.
Her unmistakable upper-class accent was pure Philly Main Line. To a trained ear like my own, it was an easily recognizable tone of haughty old money, a unique dialect honed over generations in a caste system of the pseudo-elite.
It’s hard to describe, exactly, but try to imagine combining the cadence in the voice of Rocky Balboa’s wife Adrian with the Duchess of York’s. That’s old Philly money, trying desperately to outrun its urban roots by pursuing New England-based, Ivy-League educations, but being betrayed every time one opened their mouths to speak.
“That’s one of the Cheryl Sanderson’s daughters, Stephanie, isn’t it? Lovely girl, simply lovely. Is she your little girlfriend, I presume?” The implied arrogance in the question was so pronounced as to be condescending, but then I turned to face the inquisitor and instead, I felt my heart race in tandem with the resumption of the twitching in my shorts. It was Mrs. Robinson, descended from the bleachers. How the fuck did she get down here so fast?
That question was quickly forgotten as the woman invaded my personal space, pressing up next to me along the rail so that her firm breasts pressed into my arm as I peered at her over my half-cocked shoulder, not yet having the chance to turn around fully. Her long, tanned legs bumped into my own as she wrapped an arm under mine, and her sweet scent of expensive European perfume overpowered me, rendering my sense of speech mute.
“Cheryl Sanderson and I are on the board together at Rosemont College.” My aggressive mature admirer cooed into my ear as my dick jumped like a show pony in involuntary though discreet mutual admiration. She then changed subjects rather abruptly. “My name is Lynn McDevitt, and you are simply scrumptious. So much cuter than the other young man I saw Little Miss Sanderson with last year at this same event.”
While still trying to absorb that blockbuster, I recoiled just a bit and stepped back to take a close-up look at the comely forty-something woman tightly clutching my twenty-four-year-old arm. Though the comparison was not apt at the time, when I look back on the event with the benefit now of twenty-five-plus years hindsight, every time I see Diane Lane today reminds me of how my new friend Lynn McDevitt looked to me on that fateful Spring afternoon of 1985.
Auburn hair with just the hint of gray speckles hung in delightful curls down her bare shoulders. When she finally lowered her shades, her green-brown eyes danced and sparkled in the sunlight with the promise of playful promiscuity. Her tanned and freckled chest was covered just above her proportionate breasts by a white ruffled-collar sleeveless cotton blouse. She wore fashionably pleated khaki shorts with open-toed sandals that perfectly augmented lean yet muscled calves. Main Line chic adorning her tight, athletic mature body. As I said, coquettishly slutty in a high-brow way. Flirty and lusty.
She was……well, flusty. Yeah, that’s it. I had invented a word, just for her.
Lynn McDevitt was flusty. Very fucking flusty, indeed.
As much as I was trying to deny my attraction for the overtly ambitious Lynn McDevitt, the fact that she kept pressing her surprisingly firm boobs into my arm caused my personal show pony to keep rearing its precocious head. Down, boy. I was also still trying to come to grips with her statement about Steph at last year’s event. Could it be true…..?
My head was spinning from a variety of tactile sensors, when I felt my palm being opened by Lynn’s long and persistent fingers and a business card soon filled it. “One o’clock tomorrow. A personal picnic lunch on my veranda.” I glanced down at the card with an address scrawled on the back. I not only knew exactly where it was, it was just a few blocks from Stephanie’s parents’ house. Yes, of course, she still lived with Mommy and Daddy, which meant we had to occasionally get creative for some sexual activity. I harbored no doubts that Lynn McDevitt most definitely did not live with Mommy and Daddy, though the large shining diamond on her left ring finger did give me some ambiguity regarding her relationship status.
Just then, I saw Lynn’s face up with contrived glee. “Stephanie, darling! I’ve just keeping your friend here occupied while you got your candy. He’s so yummy, some hungry birdie might try to swoop down and gobble him up. How are you, darling girl?” Stephanie tried to protect herself by waving the stick of cotton candy like a shield, but it was too late. Lynn had planted an overtly insincere bear hug on her.
Then Lynn moved in for the kill, and Stephanie never knew what hit her. She was outnumbered in this battle of feminine wares and guile, one-to-one. Lynn’s one was more than Steph’s one.
“I just saw your mother last week, and she told me your long-time boyfriend was finally home after playing ball and got a nice job in landscaping.” Lynn scrunched her eyes in mock confusion. “But, this isn’t the same young man you introduced me to here last year, is it?” Steph’s face contorted in a pained grimace. She was busted. She looked as if she wanted to shrink and hide behind the pink fluffy taffy in her hand.
Lynn recognized her jab had hit its intended target flush. Realizing that she had accomplished her goal of both mortifying Stephanie while pissing me off, Lynn now continued her charade and tried cavalierly to brush aside her remarks. “Oh, well, now that’s none of my business, is it? Perhaps I’m just mistaken. Mea culpa.”
Stephanie’s face had turned a hue that approximated that of the cotton candy. I seethed at her as Lynn gripped my arm more tightly. It was only then I noticed that she had never let go of my arm. Lynn turned to me and batted her eyes like a southern belle at a debutante ball. “While I’ve been so busy protecting you while Stephanie was away, I never did get your name, handsome.” She extended an downward turned palm, expecting me to grasp it. Instead, I took two steps back, which resulted in me wrestling away from Lynn’s grip, but also distancing my personal space from Stephanie.
“My name is John, Mrs. McDevitt. John Brinkman.” I glared at Stephanie, who almost trembled. You could almost hear the file cards in her head, desperately groping for words that would probably start with, “I can explain….” She didn’t need to, her eyes rendered her guilty verdict loud and clear.
“If you’ll excuse us, Mrs. McDevitt, I think Stephanie and I just remembered we have somewhere else to be. It was nice meeting you.” I almost pushed Stephanie towards the exit in that same spot on her backbone that I had been gently caressing just ten minutes ago. She failed to purr this time.
“Well,” Lynn said in a sing-song voice. “I do understand. I’m sure you two need to get caught up on a lot of things.” The irony was as thick as her disingenuousness. “But, Stephanie, sweetheart, do tell your mother I said hello.”
And then, as I guided Steph towards our pending argument, we heard over our shoulders, in a classic double-entendre that left little room for misinterpretation, “Oh, and John, don’t forget to stop by my house. I’d love to have a proposal for getting my lawn mowed and having my garden properly attended to.”
Not surprisingly, Stephanie used Lynn’s blatant ‘flustiness’ as the best offense for her defense. While she was accusing me of leading on a “old hag dartboard”, in Stephanie’s words, I was discovering that Stephanie had indeed ‘seen’ an old high school beau of hers ‘a few times’ last season when I was playing baseball.
I dropped her off in a huff in her parents’ driveway, irrevocable damage done to our relationship. I realized that I had perhaps jeopardized a life of marrying into wealth, yet somehow I was strangely relieved.
That’s a story not worth doting on. There is a much better story to tell. This is Literotica, after all. And I had a coming-out party awaiting me beyond my wildest imagination.
So, also not surprisingly, I pulled my rickety Grand Victoria (yup, I really drove one) into the long winding driveway off of Conestoga Road at precisely one o’clock the following afternoon.
It was a gorgeous Sunday in May, and I no longer had my usual date with Stephanie, and I wasn’t in the mood for golf. I needed something to fill my afternoon. And Lynn McDevitt obviously had a yearning to have some things filled of her own. It made for a fortuitous clash of needs.
I was somewhat surprised when I rapped on the huge front door and she answered the door herself. I half-expected a French maid or a tuxedoed butler named Jeeves or something. She was dressed in a pink and white flowered button-down sundress that displayed an ample view of those alluring freckle tits. My first thought was of Gene Wilder’s line in the movie Young Frankenstein…”What knockers!” They weren’t huge, not by any means. They were just,…well,…they were perfect.
“I was hoping you’d show,” Lynn greeted me, sounding a bit embarrassed, which threw me off a bit, since her demeanor yesterday walked the tenuous tightrope between ambition and aggression. “I was wondering if perhaps you’d be pissed off at me.” This made me at ease, and changed my impression of her instantaneously.
I shrugged, walking into the vestibule that was impressive enough to temporarily divert my gaze from Lynn’s cleavage. “I’ve never been prone to shoot the messenger. Besides, when it all came out in the wash, I have a pretty good inclination that wasn’t the only time Steph had entertained someone else.”
Lynn’s countenance now appeared soft and empathetic in this private setting , a marked contrast to her Catwoman public persona yesterday. “Well, it was not meant to hurt you, that’s for sure.” She smiled almost bashfully, and that resulted in a rise in my tenting shorts. Then she confessed, “However, I did have an ulterior motive in being a pushy old broad.” She stepped towards me, essentially pinning me to the door.
“And what is that?” I asked, assuming I may already know the answer, but figuring it wouldn’t hurt to get verification. My hands had almost unconsciously glided to her hips, and I held them lightly, encouraging her advance.
She leaned into me, pressing her leg into my now-bulging crotch. “Let’s have lunch later. Kiss me.”
Lynn’s kiss immediately taught me that whatever I thought I had discovered about a great kiss was now secondary to the way this mature woman massaged my lips and tongue with her own talented, hungry, wet warm mouth. I caressed her hair, wiping it from her face, as my head spun wildly as we were lost in the moment. It wasn’t as much sexual as it was sensual, a deep, probing kiss that extracted both passion and emotion, a true connection of deep chemistry unlike anything I had experienced.
The first kiss of a lifetime.
Reluctantly, after about perhaps five minutes or so of escalating embrace that seemed to extend for an eternity, Lynn leaned back, broke the kiss, and exhaled. She brushed the tangled mane of red-gray curls from her face, and her eyes blazed into mine. “How old are you?” she inquired.
“Twenty-four. How old are you?”
She grinned like a little girl. “Forty-eight. Isn’t that just symmetrically perfect?” She leaned in again to gently suck on my earlobe. “How many times can twenty-four go into forty-eight. Twice?”
I moaned into her own ear. “At the very least. For starters. This is new math, there will be remainders.”
Lynn’s hand began to snake down my belly and I felt it stumble for my belt. For some reason, I held her wrist to impede her path. I had to ask this question. I had to know.
“Where is your husband?”
She nodded, as if in acknowledgement that it was indeed a very fair question that we should address before proceeding. “You mean my estranged husband. He’s in London, wont be back for several weeks. His firm has an office there.” She looked at me almost pleadingly. “But the marriage is in name only, it’s been dead for years. But we must keep up appearances, for the sake of social circles, the height of Main Line hypocrisy.”
Lynn took me by the hand and we walked in silence to an over-sized couch in one of the rooms just off of the vestibule. I wouldn’t call it a living room as much as it was just one of several large foyers. In any event, she gently eased me down onto the couch and began to reach for the top button of her dress. Slowly. “Enough about my marriage, or lack thereof. My turn to ask questions. Agreed?” I nodded my assent.
“One candid question, one honest answer equals one button. Deal?” I felt my cock twitch, threatening to literally burst through my shorts. Since I hadn’t felt the need for underwear today, I wondered if Lynn detected the small stain of pre-cum forming next to my zipper. The twinkle in her eye after her glance in that direction told me that she did.
“I’m amenable to your terms. Please proceed.”
She twirled the top button between her thumb and index finger teasingly. “What’s the age of the oldest woman you’ve ever been with?”
“Um….twenty-nine. I think.” I furrowed my brow in recollection.
“How old were you at the time?”
“Hey, un uh, no dice. That’s a separate question. Undo a button, please. No cutting corners.”
Lynn smiled and willingly acquiesced. More freckles appeared, and the hint of a pink bra cup became barely visible. “OK, happy? Now then, how old were you at the time?”
“Nineteen, I believe.” This time, the dress opened to display both of her bra-encased globes. They were not the shape of most forty-eight year old women, to put it mildly. Lynn began to run her hand over the top of her left breast, almost absent-mindedly. She bit her upper lip in contemplation of the next series in the inquisition.
“How was young Miss Stephanie Sanderson in bed?”
I had to put that in perspective. I pondered for a moment, wondering how forthcoming I should be. “Well….” I hesitated. “She liked to fuck, that’s for sure. But I almost always had to initiate everything.”
Lynn looked at me with feigned sadness, fidgeting with her half-opened button. I broke all the rules of responding to depositions with the disclosure in my next sentence. “And she hardly every gave me a blow-job. And when she did, she wasn’t real good at it.”
Lynn seemed to enjoy this revelation tremendously. The dress cascaded off of her shoulders and fell loosely around her mid-section. Even her flat stomach was scattered with adorable light brown freckles. I became harder, if anatomically possible.
“Did she swallow your cum?”
I laughed out loud at this one, sputtering back a cough. “Swallow me? That presumes she sucked me until I came. Wishful thinking.”
The next button revealed the tops of Lynn’s matching pink bikini panty. (This was long before the days of thongs.) She uttered a bonus question, providing a multiple choice, of sorts. “Would you like to cum in my mouth….?” Before I could eagerly respond enthusiastically, she continued. “…..Or on my face?”
This was a win-win scenario by any stretch of the imagination. I thought of the newly revived game show Jeopardy and its young host who had replaced the legendary Art Fleming. “Um, I’ll take ‘face’ for two hundred, Alex,” I smirked, trying to be amusing.
She kicked off the dress as it fell to her ankles. “Hmmm, is that thing as big as it looks?” She stared directly at the pronounced lump in my lap, threatening to burst through the seams.
“Again, no fair, you’re out of buttons.”
Lynn looked down and grimaced in mock despair. “Well, well, so we are.” She reached around her back and I heard a small ‘snap’. The brastrap loosened on her shoulder and fell down one forearm, exposing the tan line on one breast, just covering the hardened nipple. “I guess we’re onto hooks, now, aren’t we?”
She knelt in front of me and pushed my legs apart. This time, rather than discourage her, I watched silently as she undid my own shorts and slid my zipper halfway down. “Have you ever fucked a woman in the ass?”
One hand reached to extract my cock from its Bermuda-shorts prison cell, while the other unhooked the remaining bra snap. She didn’t even wait for an answer. She moaned when she saw my cock pop from its hiding place. She stroked the stream of pre-cum from my cockhead and down the base of the whole shaft.
“Yes, once. That twenty-nine-year old.” I admitted proudly, while trying unsuccessfully to keep my voice from trembling, but by now, Lynn didn’t appear as interested in her abbreviated game of ‘strip twenty questions’.
“My God, you’re huge!” She inhaled sharply, using a second hand to surround my pole. Then, she spoke almost to herself, softly, as if taking inventory. “Hmmm, I don’t know if that will fit back there.”
Just in case, she began to trace small circles of saliva that dangled from her tongue, and lathered them all over the base of my dick, all the while mumbling almost trance-like, “Unngh, so big, so thick. Beautiful. My lucky day. You’re a baseball player, right? Jeezus, did you even need a bat? What a pleasant surprise……”
I have to confess that her words were almost as big a turn-on as her expert oral administrations. I hadn’t been with all that many women at that point, and the ones I had been with were more or less ‘girls’, as relatively inexperienced as I was, with the possible exception of Miss Anal Twenty-Nine-Year old.
A few had told me how ‘big’ I was, but to have my size validated by a woman such as Lynn McDevitt, who most certainly knew her way around a cock, was the utmost compliment. My ego rose like my cock at that moment in time.
Lynn looked up at me wickedly, with obvious evil intent in those mischief-filed eyes. “Do you know I know magic tricks?” She lifted my shaft to allow unfettered access to my testicles and began to hum as she sucked on the heavy walnut-sized balls.
“Well,” I panted, gripping the armrests of the couch as I felt the seed begin to boil deep within. “You’re doing quite a magic job on me as it is. Damn. Amazing.”
She slapped my rocks across her pretty face, in a playful self-flagellation gesture, and I admit that the sight was made even more erotic as her wedding ring sparkled while she wanked my cock.
“Well, you ain’t see nothin’ yet, young man. Turn around and get on your hands and knees on the couch.”
This was a new one on me. But, who was I to quibble with a magician? She could saw me in half at that point as long as she kept doing what she was doing. I bent over tentatively on the couch cushion, wondering what her view was as my ass pointed directly towards her face. She then revealed the secret to her audience of one.
I felt her tongue begin to rim the edges of my anus. This was most definitely another first for me. She mumbled into my gaping asshole, her words almost echoing, and for the first time I felt a tongue penetrate my most sacred hole. “For my first trick, I’m going to make you whimper like a little schoolgirl.”
She accomplished that objective with alacrity. I’d always had kind of an anxious trepidation of anything even in close proximity of my butt (ass-a-phobia?), but Lynn’s warm, long tongue felt like a tender, relaxing massage, now that I was getting used to it. The fact that she was now stroking my cock in an awkward, almost upside-down position, was helping to alleviate any tension, also, that was for sure.
“Now,” she said, maneuvering herself so that she was almost lying vertically on the carpet beneath me. “I’m going to make nearly eight inches disappear.” In three of four impassioned gulps, with the dexterity of jockey on her stallion, she took my full length in her throat with one loud gulp accompanying each oral thrust.
I felt her nose bury into my patch of pubic hair. It felt surreal, beyond my most vivid fantasy. A married forty-eight year old vixen was deep-throating me from behind as I was in a thoroughly vulnerable condition, and loving every second. I was in complete surrender, thinking heaven couldn’t get any better than this, when I felt her pinky finger ease into my sphincter. My cock twitched and rumbled and I imagined that schoolgirls everywhere would have giggled in response to my squeals.
Intuitively anticipating my pending explosion, Lynn quickly flipped me completely around with surprising strength, and pointed my cock right at ground zero, otherwise known as her chin.
The semen erupted from my slit like a massive dam break, coating Lynn’s neck with a projectile-like force. Perhaps ten spurts shot like white volcanic ash over her forehead, between her eyes, on her fluttering eyelids, in her hair, on her cheekbone, and then, ultimately, the grand finale. She took her tits and wiped her erect nipples on my cock so that the last trickles of cum dangled from her pointy nubs.
I lay on the couch, trying to keep from hyperventilating, as I watched her scoop up the sticky, bubbly cum suds from her face and lick them from her fingertips.
All I could muster was, “Bra-fucking-vo, maestro. What a performance.” It was at that precise moment in time that I realized the virtues of an older woman’s charms. I was hooked. Yet far from done. Reciprocation was my middle name. (Well, actually, it’s Charles, but work with me on a little poetic license, will ya?)
I bent down to lift Lynn and guided her down next to me on the couch, and expressed my appreciation with a series of long, hot kisses. It was the first time I had ever tasted myself, ass and all, and the strangely pungent flavor was not entirely repulsive. (OK, OK, I liked it, it was hot! You happy now?)
My tongue went slowly into her mouth repeatedly, and she returned the favor. We sat there kissing for quite a while, until she began humping my leg with her wet crotch. I rolled her over on the couch, and began kissing my way down her sexy body. I was making it a point to enjoy every inch of her.
I tasted, smelled and felt her entire body. I spent a long while licking and sucking on her breasts. They were so firm and her nipples were sticking straight out. I was alternating between licking one and working the other between my fingers.
I began kissing down her soft, flat stomach, and the scent emanating from her crotch mixing with the sweet smells of her body lotion and perfume were intoxicating. I covered her tanned, flat, smooth stomach with kisses as I worked down to her sweet pussy. She was raising her legs into the air as my mouth reached the object of my desire.
I removed the sheer pink panty and looked at her bare pussy for the first time, and it was absolutely beautiful. Her lips were perfectly shaped, and they were all creamy with a delicate pale fluid oozing from her folds like a softly trickling stream. I inserted two fingers and began to explore, stopping to remove them and savor the buttery cream. Yum.
Her soft wisps of reddish pubic hair made a perfect path to her clit. Her inner lips were very pink, and her whole pussy was swollen with lust. I looked up from between her legs, over her tummy, and up past her tits to her face which was glowing with arousal and anticipation.
It was the sexiest sight I had ever seen in my life.
Her eyes were closed, and she was lost in passionate bliss. It was an incredible turn-on for me knowing that I had been a part of bringing her to this point of passion. That, and the fact I was about to lick the most beautiful pussy I had ever seen, was about to push me over the edge.
I lowered my face and inhaled her tantalizing aroma.
As I leaned in closer, Lynn raised her crotch to my face. My tongue slid right in and was instantly covered with the sweetest, creamiest, nectar in the universe. I thought it was good off of my fingers, but straight from the source was almost indescribable.
She arched her back and shoved her pussy into my face and I stuck my tongue in as far as I could. I began rubbing her perfect butt, and she was going crazy. She started begging me to stick it in. So, wanting to please, I slid my finger in as deep as it would go and began turning it as I slid it in and out of her tight bum.
The mature beauty was writhing at my every touch, and I was entranced with her body. I never knew that an older woman’s passion could be so intense, and that I could feel so captivated by pleasuring a woman twice my age in this way. It was like I could do no wrong. Everything I did turned her on even more. I was sucking on her clit and sliding my tongue up and down, and in and out of her saturated, sopping slit. I could tell she was getting ready to cum.
Lynn arched her back and grabbed the back of my head and pulled my face into her pussy. Next thing I knew, my mouth was being flooded with her juices. It was incredible! I almost couldn’t swallow it all. She kept cumming until I slowly pulled my finger from her tight ass, and my tongue from her slit. She lay there almost unconscious for perhaps about three minutes while I leisurely stroked my titanium-hard shaft, patiently awaiting her resurrection.
“Oh my God, WHO taught you to do that?” She said, finally stirring, as she looked up at me with a dazed but sated look.
I smiled down at her, admiring the look of sexual bliss adorning her still cum-splattered face. “I have a bit of an oral fixation, and yours is the most delectable pussy I have ever enjoyed. I could stay down there all day.”
She reached up and grabbed me by the back of my neck, pulling me down on top of her. “Kiss me,” she panted, in a demanding tone. “I want to taste myself on you as you fuck me.”
Lynn’s kisses were indeed electrifying. My cock needed no additional incentive, it was more than ready for prolonged action, but the way she kissed me remains imbedded in my brain to this day.
We kissed frantically, our tongues molding together like seasoned teammates, and the tip of my cock eased into her still soaking gash. She released the kiss for just a second. “Keep kissing me while you fuck me, stallion. Kiss me like you want to fuck me, and fuck me like you want to kiss me forever.” And just to be sure I understood, she grabbed the back of my ass and thrust it towards her target.
“And fuck me hard, rough. I like it that way, I need it that way. Don’t hold back. Let’s see how many times eight inches of twenty-four can go into this tight forty-eight year old pussy.”
A lot of times, as it turned out.
I’d never yet had a woman even remotely talk to me in this way, and it provided me with the life-long revelation that hot sex is only enhanced and augmented by an open, steamy, verbal dialogue. Or, in Lynn’s case, since I was still new to this (but a quick learner), a monologue. It helped that hers was riddled with obscenities and exhortations rarely heard publicly on the tranquil sidewalks of Lancaster Avenue. The dirtier she talked with filthy encouragement and directives, the harder I fucked her.
I grabbed her thin ankles roughly and spread her athletic legs as far as they could be spread and joined in the diatribe. “I have my own magic tricks, you fucking cockslut. I’m gonna split that hot cunt of yours in two…..”
She wailed as the tip of my cock banged against her cervix repeatedly. My cock audibly snapped each time I entered her as deeply as her snatch would allow, hitting rock bottom on the hard wall of the back of her pussy. Yet the more I thrust, the more she yelled for more. More. More cock……….
Lynn’s head had virtually disappeared into the couch cushions, such was the urgency of our frantic fucking. With each rocking of my pelvis, I felt her inner walls struggle to grip my dick, attempting to adjust and expand so that she could accept more length, more girth, more dick. “More, deeper, harder, more cock,” she screamed over and over, our aerobics rattling the crystal chandelier in the adjacent room.
Sweat poured from my brow and streamed onto her torso, and I became legitimately concerned that I would smother her, her face was buried so deeply in the upholstery.
And so I became the choreographer, picking her lithe frame up, high in the air, fucking her standing up for a few moments while we continued to lock lips while she mumbled every combination of x-rated rantings into my mouth, and then finally, I turned and plopped myself down on the couch, never releasing her humid pussy from my engorged cock, and slammed her down on me, reverse cowgirl-style.
I pulled her wrists back so that they were locked in my palms, assuring that I could continue to control her body, which by now, had unequivocally surrendered to the assault being perpetrated on her by my cock. I pulled her back towards me and began caressing her nipples with my free hand, and she was now close enough to me to swivel her neck around to kiss me once more. Every time her lips met mine and her tongue sucked into my mouth, the electricity within my cock rose exponentially. How did Lynn put it? “Fuck me like you want to kiss me forever….”
By now, I was an unabashed convert to the virtues of sexual endeavors with an older woman. But, greedy bastard that I’ve always been, I wanted more.
I wanted that ass of hers.
I pushed Lynn up, releasing her wrists, so that she could now bounce unencumbered on me. She placed her hands on my thighs to balance herself while I could now watch my dick squish in and out of her puffy pussy lips, now liberally dripping with a milky white liquid substance. (What a beautiful view.)
As if reading my mind for the eventual destination of my cock, Lynn dipped her fingers into her mouth and began salivating over three digits. She then reached back, all the while groaning and bucking her hips down onto my lap fiercely, and stuck first one, and then another finger into her rectum, twirling them around like miniature corkscrews in an attempt to lubricate and loosen her anal cavity.
She looked back to admonish me, pulling out her fingers with a ‘pop’, and then wagging them at me with raised eyebrows and a maternal scowl, which was ironic because she was old enough to be my mother. “There’s a time to be rough. This is not one of those times. You’re hung like a horse. Don’t ruin me. Go slow. Please.”
She raised her hips off of me, reluctantly pulling her steamy, humid cunt off of my beet-red member. My cockhead was literally being rubbed raw by the force and friction of our animated fucking. I could only imagine the bruises and bumps on Lynn’s vaginal walls and cervix. No wonder she wanted it in her ass. She needed to give her poor pussy a break.
With the careful precision of a surgeon performing micro-surgery, she reached around and with both hands, she pried her taut ass cheeks apart, causing her winking bung hole to gape at me teasingly. She fell back, her back on my chest, to brace herself against the upcoming anal penetration. She stuck yet one more finger into her anus after licking it with enough spit to put out a small brush fire.
A slight rise of her hips, and my cockhead slid into her as about a half-an-inch, just enough to make her wince. “Oooo,” she groaned in a guttural exclamation. “Aaah,” I exhaled, feeling the heat and vice-like grip of her tightest hole grip my cockhead like a flaming glove.
She rocked ever so slowly on me, and with each subtle gyration, my cock slid in perhaps about another quarter of an inch. Without turning around this time, she gave me additional counsel. “It’s close….aaahhh. When you hear and feel the pop, then you can go fast. Get ready……..”
About ten seconds later, I did feel the aforementioned pop, as her anal muscles immediately wrapped around my shaft like a collapsing wall of heated bricks. She leaned back more, grunting loudly now, and I grabbed her breasts roughly, groping the small grapefruit-sized orbs, pinching and pulling on the rubbery nipples until they distended almost a full inch from her areolas, and I began to nip on the nape of her neck as her hair flew wildly into my eyes.
“Oh…my….God, this is fucking amazing. Oh, fuck, what a feeling, unmmmmhhhhh. It’s like I have a flamethrower in my asshole, I’ve….unnnnh……I’ve never……….”
Just then, as my own balls were about to implode, I felt something unlike any sensation before or since. Lynn’s anal channel literally began to rumble, and I could feel her sphincter pulse and yawn around me, my cock now buried probably five or six inches in her forty-eight butt. She sat frozen on me for perhaps five seconds, perfectly still except for a barely perceptible trembling running through her inner thighs, almost as if she were suspended from an attack of vertigo. Then suddenly……….
“UNNNNGHHHH, OOHHHH, MYYYYY, GODDDDDDDDD. FFFFF-UUCCCKKKKKK…………” She shrieked like a exotic bird and shook like a screen door in a hurricane. Lynn’s body convulsed as if being manipulated by a puppeteer and I felt a splash of warm moisture on my lap, running down onto my thighs, spilling onto the couch. Her body writhed and gyrated and her skin turned the hue of the gills of a salmon, caught on the hook, my cock serving as the bait, flopping in desperate confusion.
All the while, I continued to pump my cock ardently into her bowels, and the more I fucked her ass, the longer and more animatedly Lynn orgasmed. When her body could literally take no more blissfully sweet punishment, she virtually catapulted herself off of me and onto the couch in a fetal position, rocking back and forth and mumbling incoherently. It wasn’t until that very moment that I realized that she had two fingers pressed against the nub of her clit. She was still frigging herself spiritedly.
From my vantage point just a few feet from her buttocks, I could see her anus opening and closing like the contracting entrance to a small tunnel, which is exactly what was occurring. I remember this scene every time I see a woman coming profusely. It’s an involuntary reflex. Their assholes always verify a gigantic orgasm in a truly authentic way.
I thought she was done, and I stood up and hovered over her tentatively, like a fighter who stood over an opponent was expecting the referee to initiate an eight-count. Yet, with perhaps her most impressive magic trick of the afternoon, she rose, Lazarus-like, and I gasped in shock as she grabbed my cock with two hands, and stuffed the raw meat into her mouth.
She ran two long fingers underneath my shaft and began to stimulate that incredibly sensitive area right at the base of the pubic bone, below the balls and just above the anus. Though I didn’t think it possible, this caused my dick to grow even longer and firmer. Feeling this, since my cock was buried deep in her mouth, Lynn knew that she had me on the verge again and could time my ejaculation pretty much any ol’ time she damn well pleased.
And the time was nigh, as they say in Scotland. Echoing my words from earlier, she let her mouth ease off my cock for just long enough to look up at me and utter, “My face for two hundred, Alex.”
She lowered her head and resumed her fun. I responded affirmatively with a generous helping of her second feast of face-food in the last hour or so, some of the semen coating over the same spots where there was now dried blotches on her skin and hair from the prior oral homage.
We curled into a mutual ball and cuddled, dozing out of sheer exhaustion for a few minutes until she glanced at her diamond Movado wrist-watch, between the two of us, the only thing we had on. Well, other than her wedding ring, of course.
“C’mon, let’s take a shower, and then have some lunch finally. We have a lot to talk about.” She pulled me up by the arm and kissed me again. Best kisser ever.
I tagged along as I watched her beautiful ass sashay in front of me, still red from my grips on her buttocks and still distended from my cock being up it less than five minutes ago.
“I didn’t get a chance to tell you, but the reason I was at the Horse Show yesterday is because I am an equestrian rider, and I have a performance on Wednesday evening at Devon. I’d like you to attend. I also have a dear friend I’d like to introduce you to, if you wouldn’t mind me ‘leasing’ you out to her for a…..ride. I think it’d be much fun to share you, if you think you could handle two forty-eight year-olds.”
“Wednesday night, hmmmm, lemme think.” I rubbed my chin, as if pondering my dance card. Lynn smacked my stomach playfully, knowing full well I would make myself available even if a plow horse had to haul me over. I thought about the prospect of a threesome. I’d never had one, not a FFM, anyway. “Are you serious?” I asked, hoping she was.
“I’m very serious,” Lynn winked, leading me up the stairs and into her master bedroom. “And don’t call me Shirley.”
Before heading into the bathroom, I couldn’t help but notice a picture of a stunning young redhead on Lynn’s dresser. The girl appeared to be about nineteen, the spitting image of Lynn. “Um, who’s that?” I inquired, resisting Lynn’s tug for a moment.
Lynn’s mouth opened in mock horror. “Oh, no, don’t you even think about it. That’s my daughter, Kelly, and she’s off limits. You’d break her apart. Besides, by the time I get through with you today AND my friend and I do you on Wednesday, you’ll never want to fuck a woman under forty-five again. She’s probably hornier than I am, if you can believe that.”
The mind boggled.
She turned on the shower as we climbed in and the warm water began to flow from the nozzle, therapeutically refreshing our bodies for the next round, which would ensue immediately.
Two forty-eight year olds, I mused. I wondered how many times twenty-four could go into ninety-six.
I was still considering that when Lynn knelt before me and took my flaccid cock in her mouth, thus resuming a new marathon event, this time in an aquatic setting. She sucked my cock into Monday morning, again and again. The virtues of an older woman.
On Wednesday evening, I stood by the rail of the main rind, waiting for Lynn’s turn to perform with her steed, when I heard a husky voice behind me. “You must be John, Lynn’s new ‘friend’.”
I turned to see a gorgeous, buxom blonde with an hourglass fixture. She extended her right hand as I saw the ring glisten on her left. “I’m Mary Ann Nelson. I understand we’ll be having a party tonight.” She visually measured me up and down like a hungry feline would eyeball a trapped mouse. “How nice.”
Seconds later, I heard a much younger voice from the grandstand holler, “Go, Mom! Woo-hoo!” Kelly McDevitt’s clear blue eyes then met mine, at the exact second Mary Ann Nelson entwined her arm in mine.
Kelly McDevitt may have been the hottest nineteen year-old in Delaware County. Talk about a conundrum. I intuitively knew I was going to fuck Kelly someday, and I found out later, Kelly knew instantly she wanted to fuck me.
“Hi, Mrs. Nelson,” the young freckled redhead yelled merrily to my older threesome-partner-to-be, her mom being the other member of the trifecta. “Is that your nephew or something? He’s cute! Aren’t you going to introduce us?”
Higher up in the bleachers, from the corner of my eye, I saw Stephanie Sanderson sitting with a heavily muscled young man, taking everything in with a frown.
There is always a lot going on behind the scenes at the Devon Horse Show. The best performances are not always in the ring.