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The Midnight Train Going Anywhere

Category: Mature
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It wasn’t until that very moment that the full gravity of the nation’s economic downturn hit Lisa Ross. The newly hired Vice-President of marketing at an upstart South Florida publishing company, the previous handful of jobs Lisa had, air travel (usually first class) had been the mode of choice. Now she found herself seated and staring out the window of an Amtrak train as she prepared to embark from Miami to Washington, D.C. for a weekend conference.

Lazily thumbing through a section of the presentation she was going to give at the Expo, Lisa knew there was certainly a golden opportunity to make some waves for her new company. On the other hand, as shaky as the economy was, she also wasn’t going to miss an opportunity to put in some valuable networking time in case the need to find another new job presented itself.

Keeping her fingers crossed no one had a ticket for the seat beside her, a lump of trepidation formed in Lisa’s throat each time a straggler made their way down the aisle. It wasn’t that she felt uncomfortable mingling with complete strangers, she fancied herself a very social person, but given her recent relationship issues, not to mention the humbling experience of having to take a train on a business trip, Lisa really wasn’t of a mind to make small talk about the minutia of life.

It was only a few minutes from departure time, and Lisa was just beginning to feel comfortable enough to sit her laptop down on the seat to her left when she looked up at the last few approaching passengers. When she did, her heart nearly stopped.

As a polished and poised 34 year old business woman, one who admittedly was rarely ever at a loss of words or confidence, Lisa suddenly found herself reverting back to being an eager but somewhat awkward college undergrad when she saw one of her former professors from the University of Miami enter the cabin looking for his seat.

“My God… that’s Dr. Jerden,” she mouthed, immediately kicking herself for not taking the time to do her hair and make-up before getting on the train for the long trip.

“He’s aged some, but he still looks good,” she noted, doing her best not to make direct eye contact as the unsuspecting older man followed the herd down the aisle.

Unsure quite how she’d handle the situation when Dr. Jerdon walked by, Lisa found the previous 15 years or so passing before her eyes as he approached.

Dr. Garrett Jerden had been Lisa’s English Professor her Sophomore year at Miami and helped set her up with two internships over the Summer while she was there. There was nothing more to their relationship than a typical teacher-pupil dynamic, but Lisa certainly saw the now 62 year old man as a mentor and certainly someone she learned quite a bit from, and held in deep regard for some of the doors he helped open for her right out of school.

So there was simply no way Lisa could avoid making eye contact with the man as he walked past, and after a few seconds of excited pleasantries, Lisa invited Dr. Jerden to take the available seat beside her.


Garrett was taking the train up to Maryland to visit his Son and Grandkids for the weekend.

A Widower for a little over a year, he’d always been a train enthusiast and it was his preferred choice of travel when time wasn’t a factor. To say he was shocked when he locked gazes with Lisa would have been an understatement. Still teaching two classes each semester, there had literally been thousands of students that had walked through Dr. Jerden’s doors, but only a handful of them really stood out.

“Lisa Sanderson,” he exclaimed the instant he recognized the girl staring back at him two rows ahead.

“Well it’s Lisa Ross now… or at least for a little while longer,” she smiled back before leaning forward and giving the Professor a big hug.

Once he was seated and the train departed the station, the two spent the next few hours lost in conversation. Lisa consoled Garrett on the loss of his Wife, he listened and gave some rather sage advice about the impending dissolution of Lisa’s marriage. The two talked about careers and changes to the academic landscape along with a million other trivialities of the day. By the time they looked up and realized how much time had passed, they were well into South Carolina, nearly half way to D.C.

The extended conversation with Dr. Jerden created quite a transformation internally for Lisa. She couldn’t remember the last time she’d had such an intimate and in-depth conversation with a man. Having grown up with an emotionally, and often times, physically absent Father, for some reason Lisa seemingly gravitated over the years to men just like him, her now estranged Husband being the king of that unfortunate crop.

Even as a doe-eyed college student however, Lisa always felt a measure of comfort in Dr. Jerden’s presence. His paternal aura combined with his acumen in the field, not to mention his humble an unassuming presence made it easy for an impressionable young woman to fall under his spell. Even then Lisa knew Garrett Jerden could have had his pick of the pussy on the co-ed buffet, but never once did he give the slightest inkling he’d be interested in crossing that sacred line that so many of his fellow professors freely did. She even remembered how quant and romantic it was seeing how he always kept the picture of his Wife and kids on his desk, as if showing them off for the whole world to see.

To hear his Wife had died caused such a stroke of sadness to shoot through Lisa that she’d subconsciously extended her left hand and closed it tenderly around Dr. Jerden’s right as he relayed the story.

By the time their conversation started to peter out, Lisa found herself less than a foot from the older man as the surrounding gallery of travelers occasionally looked over at the talkative couple with a mixture of fascination and annoyance. In many of those onlookers’ eyes there was a clear twinkle of premonition of how the night would end for Garrett and Lisa long before they had a clue.


The Sun was just starting to set in the Western facing windows of the train as the attendants began milling around taking people’s orders for dinner. After talking non-stop for so long about such a varied array of topics, suddenly the words became tougher for Garrett and Lisa to find.

“So… is someone meeting you at the terminal?” Lisa asked as she looked hopelessly down at the unappealing menu.

“Yeah… my Son’s gonna be there… you know its a shame you already have the hotel lined up on the company’s dime… you’d be more than welcomed to come stay with us for the weekend,” Jerden offered.

“Ah… that’s sweet… probably not exactly what your Son and Daughter-in-Law envisioned… you bringing a lost puppy like me with you up to visit,” Lisa laughed.

“Maybe you’re right… it would probably raise some eyebrows… tell you what though… nothing on this menu is really jumping out at me… there’s this really great Italian place less than a block from the downtown train station… let’s grab a bite there if we get into DC in time,” the Professor offered.

“Your Son isn’t going to mind tagging along and being a third wheel is he?” Lisa smiled.

“Nah… let me grab my phone. I have an idea,” Garrett nodded quickly before thumbing in his Son’s number.

Listening as Garrett told his Son that he’d ran into an old college friend on the train and they were going for a drink or two once the train arrived sent a shiver of excitement down Lisa’s spine.

“He’s making up a story to spend more time with me,” she found herself thinking as she looked over at Dr. Jerden finish up the conversation on the phone.

“I told him I’d ran into an old friend and that I’d grab a cab to drive me out to their house after we’d visited out for awhile,” Garrett told Lisa after he’d hung up the phone.

“I know… I heard… you made me sound like an old grizzled colleague,” she playfully taunted as the energy began to swirl between them.


The restaurant Dr. Jerden had spoke of was everything he’d promised and more. Arriving about 45 minutes before closing time, the couple proceeded to stuff their face as the staff cleaned up around them. Like two overfed bears staggering out into the streets of DC a few minutes past midnight, the presence of Lisa’s hotel stood like a beacon just one block away.

More than a dozen taxis lined the curb between the restaurant and the hotel, each one capable of taking the Professor out to the suburbs where his family lived, yet the odd pairing continued to walk slowly past each one until they were at the hotel’s entrance.

Like two ethereal spirits in the night, arm and arm the two made their way to the desk to check in then up to Lisa’s seventh floor room.


Garrett’s cell phone woke Lisa up a little after 4am the following morning. It took several rings before Garrett was stirred awake enough to gain his bearings and reach for the phone in his pants pocket on the floor beside the bed.

“4:15,” she moaned when she looked over his shoulder and saw the time on the screen when he answered it.

“The first meeting’s at 8… good thing the phone rang or I’d probably slept right through it,” Lisa chided herself for not at least calling down to the desk for a wake-up call before things got out of hand a few hours earlier.

“Yeah… Yeah… Yeah… I’m fine… Yeah… .sorry for not calling… Yeah… got a room after the bar closed… Yeah… I’ll get there before breakfast,” Dr. Jerden sleepily apologized over and over to his Son who was wondering what the Hell happened to him.

“That damn Son of mine is treating me like a kid who stayed out all night without calling,” Garrett cracked after hanging up the phone and settling back own beside Lisa.

“He’s gonna think I hired a trick,” he laughed before nuzzling closer and kissing Lisa on the cheek.

“I hope I was worth the bill!!” the groggy younger woman giggled.

“Let me leave a tip down here just in case,” Garrett sighed without missing a beat before dipping his head under the covers.

The darkness of the unfamiliar bedroom enveloping her, Lisa could barely make out the lump of Garrett’s body as he descended under the sheets. Any cobwebs of sleep remaining in Lisa’s head quickly melted away the instant she felt his hands slip between her thighs. Biting her lip and yelping out loud, Lisa’s entire world filled with neon when Dr. Jerden walked his fingers through the same pussy he’d rambunctiously pillaged before they fell asleep in each other’s arms.

Casting a furtive glance at the hotel room door the moment Garrett lips closed around her damp and throbbing labia, Lisa rubbed the top of his twisting head through the sheet, imagining how it must have looked when he first walked her through that very door a few hours earlier.

In her mind’s eye Lisa could picture the ghostly image of Garrett leading her into the room, his right hand placed gently around her waist as he closed the door behind her. Once in the sanctuary of the suite, it was as if every bit of sexual tension that had grown between the two exploded like a punctured kettle.

Unlike the times way back in school when their eyes would meet for a fraction of a second in the lecture hall, or the times she would visit his office only to be faced with that awkward moment of silence that always came when the realized the were alone, or even the previous few hours they’d just spent side by side on the train, now there was nothing to stop them, no teacher/pupil entanglements, no marital vows that mattered on either side or wandering eyes of strangers to shy away from, simply a man and a woman alone in a hotel room, attracted to each other on a multitude of levels aching to lose themselves in what the other had to give.

Laying there in bed, her legs spread wide beneath the sheets as the Professor’s tongue lapped feverishly through her pussy, Lisa stared off into the darkness, re-living in her mind how the couple must have looked as Garrett gracefully waltzed her across the floor before finally pinning her against the far wall of the room.

Squirming in bed as Dr. Jerden ate her out in real time, Lisa could feel her nipples tingling as she harkened back to how good it felt the first time the older man squeezed them through her shirt as his kissed his lips down the side of her neck. Remembering how she wrapped her left leg around the back of Garrett’s right to pull him even closer, they hadn’t been in the room three minutes before Lisa found herself fumbling with the buckle of the Professor’s belt.

The wanton eagerness of their primal advances resulted in a tornadic trail of clothing being strewn across the room as they rotated like a bottle top, arm in arm from one end of the suite to the other. Lisa had told Garrett back at the restaurant that all she wanted was to get to the hotel room and take a long hot shower to wash away the residue of such a long train ride. For better or worse, the shower she spoke of would have to wait.

Lisa remembered the seismic shock that rippled through her body the instant she reached her hand inside Dr. Jerden’s pants and closed it around his cock. From the way the older man’s knees buckled, she was pretty sure he was feeling the same electricity as well.

Freeing herself from their embrace a few seconds later, Lisa dropped to her knees as if by primal instinct and took her place at Garrett’s feet. Her face at perfect eye level now with his crotch, Lisa pumped the growing shaft of the Professor’s penis until it was flaring wildly in her clenched palm.

“AAHH… AAAHH,” Garrett gasped each time the younger woman’s fingertips brushed up and down the smooth, stretched skin of his manhood.

Oh how he’d dreamed of doing this with Lisa way back when she was a student of his. Like most any male educator, he’d fantasized about doing such a thing with many of his female students, but to actually have it happening caused Garrett to brace both his hands down on the top of Lisa’s head to keep from toppling over in gleeful and appreciative shock.

Kneading his fingers through Lisa’s thick, luxurious brown hair, Garrett looked down and heard a chorus of angels singing in his ears when he saw the kneeling girl’s mouth open and the head of his cock disappear between her soft, warm lips.

Reaching down with both hands and caressing Garrett’s head beneath the sheets, Lisa squirmed and bucked her hips on the mattress as she rubbed her pussy against the man’s buried face, the entire time re-living in her head how good it felt to take his dick into her mouth for the first time.

For starters, even for someone as vivacious and vividly beautiful as Lisa, the only man she’d been with over the past eight years was her Husband, the same Husband she had now been estranged from for nearly a year. So it had been that long since she’d had a penis anywhere close to her mouth, but it didn’t take long for Lisa to fill with a prideful sense of control having a man quiver in that special way above her each time she slithered her tongue around the tip of its bulging head.

Even though Garrett was the oldest man by far she’d ever been with sexually, other than the salt and pepper coloring of his pubes tickling her nose, there was nothing about him that told Lisa he was old enough to be her Father. His cock jerked and lurched in her mouth just like a teenager’s as he massaged his fingers soothingly into her scalp.

It was only a matter of time before Garrett started swaying side to side, giving the appearance of a large tree gradually being felled. Licking her tongue seductively up and down the base of his jutting penis, Lisa shamelessly looked straight up at him from her spot on the floor, making sure their eyes met for several seconds before ingesting his cock once again, this time nearly swallowing the entire thing whole as he looked down in awe.

“God Lisa… this is better than I ever imagined,” Garrett gulped between heavy breaths as he teetered above her.

“You actually thought about me doing this all those years ago?” she teasingly asked when she pulled her mouth away for a moment.

“YES… and many times since,” he sighed unapologetically.

“Me too,” the girl on her knees nodded before extending her lips back around his saliva drenched staff.

Lisa didn’t need to be a genius to sense Garrett’s orgasm was steadily building. From the way his knees buckled to each side of her cheeks to the short, choppy gasps leaving his lips, she steadied herself knowing a thick wave of the Professor’s semen could wash down her throat at any second. Sucking even harder, as if desperate to taste the sticky proof of his lust for her, a tremor of confusion and disappointment reigned through Lisa’s soul when he reached his fingers down to her chin and gently nudged his cock free from her mouth.

“I might only have one good shot in me… .I want to make it count,” the 62 year old man breathlessly admitted before beginning to step out of his pants, his shiny prick bouncing like a fleshy sword in front of him as he helped his former student to her feet.

Despite his best efforts at decorum, Garrett couldn’t camouflage his eagerness and quickly reached out to squeeze Lisa’s breasts through her top. Leaning in to kiss her on the center of her throat, Garrett used one hand to fondle the young woman’s titties while using the other to grope her behind. Seemingly on fire as he caressed Lisa’s body, he finally nudged his lips up to her ear.

“I want to fuck you,” he whispered to her. “I need to fuck you!”

Lisa didn’t say a word, she simply reached down once again and tugged at her mentor’s erection before helping him strip of her of every stitch of her clothing.

To see Lisa’s nudity reveal itself one strand of fabric at a time was a transcendent moment for Dr. Jerden. Having been with the same woman most of his adult life until she died, to see a feminine specimen as youthful and vibrant as Lisa sent one jolting rush of adrenaline after another through Garrett’s system as her breasts spilled free from the bra cups he helped unclasp.

His temperature rising as he traced his hand down Lisa’s smooth, flat stomach, Garrett felt his rickety knees just about give way when his fingertips dipped into the warmth of Lisa’s puckered vaginal bloom. Kissing her on the lips and he pulled her tightly against him, Garrett stood there in a daze as his former student continued to stroke his ready and willing cock.

His eyes closed, losing himself as he inhaled her divine perfume, it took a few seconds before Garrett realized Lisa was starting to pull away so she could drift down onto the bed. Instinctively, he grabbed her by the waist.

“No, ” he calmly insisted. “I’ve got a better idea.”

Flipping the naked woman around, Garrett pressed his hands down on both of Lisa’s hips and proceeded to walk her briskly towards the large window in the room that faced downtown DC. His rigid cock bouncing off the side of Lisa’s thigh with each step they took, Garrett prayed he wouldn’t cum before getting her there.

The scenery of all the monuments all lit up against the backdrop of the crystal clear night sky provided a glorious sight for both of them to stare out at from their seventh floor view. The one thing that immediately stood out was the Washington Monument towering over everything in the distance, its gaudy phallic presence overpowering for Lisa as Dr. Jerden pulled her asscheeks apart and mounted her pussy with divine purpose from behind.

Gazing out over the regal DC landscape as he buried his penis deeper into Lisa, Garrett positioned his feet to the outside of hers, imagining how the sky outside would look filled with the Fourth of July fireworks display.

Clenching his hands around Lisa’s waist, Garrett gracefully pulled her crotch backwards against his as she spread her hands out to each side of the window sill for support. The wet and fervent grip of Lisa’s vaginal muscles clinging immediately to his cock, as soon as Garrett saw Lisa had braced herself he began pumping forward with all the accumulated, pent-up lust he had for her.

It had been so long since Garrett had such a young and eager pussy constricting around his cock, he stood there behind Lisa with the incredulousness of a school boy having his first fuck. With the advantage of knowing now what he didn’t know then however, it didn’t take him long to seize the opportunity and run with it. Slipping his hands along the front of Lisa’s torso, Garrett anxiously squeezed and kneaded at the young woman’s heaving breasts, feeling her nipples pulse and grow between his fingers each time he rammed his pelvis forward.

Eventually sliding his hands up and over her tanned, well toned shoulders, Garrett marveled at how every muscle in Lisa’s beautiful body seemed to flex and flare as she absorbed his virile assault. Finally slipping his fingers into the thick, flowing locks of Lisa’s light brown hair, Garrett felt goosebumps rise across his bare skin as the softness of her mane enveloped his hands each time she jerked her head back and forth.

Another minute of this Garrett knew he’d cum, and cum hard. This time however, it was Lisa and her devious mind that had other ideas.

Stepping back and allowing Lisa enough room to twist around, Garrett stood there with nothing but a hard-on and a blank look on his face as he waited for his former pupil to make some sense of the situation. When he saw the way she propped herself up on the window sill facing him, he started to understand.

Watching Lisa extend her legs invitingly out to each side, Garrett’s eyes immediately gravitated to the same gaping pink bloom his cock had just been buried inside. The semen in his balls rising to a steady boil seeing the way Lisa pinched and tugged at her nipples as she stared him down, Garrett felt as if he was walking on air as he stepped towards her.

“I wanted to be able to look you in the eyes… to see your face when you came,” Lisa said with soft but primal clarity.

Grabbing the base of his cock as he took his place between Lisa’s thighs, Dr. Jerden’s shoved forward, his dick slicing into her womb like a sabre through hot butter.

“AAAAAHHHHHHHHH,” their sighs rose in unison as Garrett placed his hands behind his former student’s back, both to support her weight in the window and to shove her pussy hard against his raging manhood.

Pushing his cock all the way into Lisa’s drenched quim, Garrett was now face to face with the younger woman. Feeling her gasps wash across his face each time he hammered his prick home, every drop of liquid in the Professor’s body started to sizzle when he felt Lisa wrap her legs like a vice around his back.

“AAHHH… AAAHHHH… SO GOOD… Yessss Dr. Jerden… fuck me,” Lisa sporadically spat, digging her heels into Garrett’s hips as she locked her arms tight around the back of his neck.

Wanting to scream at the top of his lungs, just to tell Lisa how good it felt to actually have her, Garrett decided it was better in the moment to channel every ounce of energy he could into thrusting forward with reckless abandon, desperate to push through to the most debilitating rapture of his long and memorable life.

Feeling Lisa’s breasts bouncing crazily against his chest each time he crashed his groin into her’s, Garrett’s willpower to delay his gratification quickly began to melt as soon as she began nibbling on his earlobe and neck.

“Come on Doctor Jerden… Don’t Stop… FUCK ME HARD… Come On… Cum inside me PLEASE… Cum Inside Me Doctor Jerden,” Lisa hissed unrepentantly into his ear.

Considering the urgency and intensity he was thrusting into Lisa with, it was a blessing they were in such a well constructed hotel or there was a chance Garrett may have smashed Lisa straight through the glass and tumbled with her to the downtown street below. Instead, the window provided perfect support for Dr. Jerden to consummate his deed, not to mention creating quite a curious sight for anyone who may have been walking down the sidewalk at that late hour.


Even though it was still pitch black in the hotel room, every color in a space-aged box of Crayolas seemed to explode in Lisa’s head as Garrett feasted under the sheets, rolling her inflamed clitoris between his tongue and front teeth until she was squirming back and forth across the mattress like something from of “The Exorcist”.

Rocking wildly back and forth, Lisa clamped her knees tight around the older man’s head, as if trying to absorb his face into womb as he hungrily chewed her over the edge. Closing her eyes and gritting her teeth hard, Lisa allowed a tidal wave of orgasmic euphoria to wash endlessly through her body until she was left with no choice but to scream her joyous release out to the Good Lord above. Garrett never wavered as his former student came, his tongue now feeling like it weighed a thousand pounds with the dexterity of a cobra as he lapped up the drizzling sheen from Lisa’s sugary vaginal walls.

Feeling every bit of her pent-up lust spewing like the air from a stuck balloon from her frothing pussy, the only thing resembling how Lisa felt at that moment was the glorious rush Dr. Jerden felt hours earlier when he’d fucked her in the window sill on the far side of the room.

Nothing would fill Lisa with as much pride as she felt witnessing her former Professor’s release play out, feeling every muscle in his body tense and fire as he crumpled on top of her, sending wad after wad of his searing lust deep into her loins. Vividly remembering how she could look down and see the complete and utter joy on his face, Lisa had committed to memory the vibrations of his heart when his chest came to rest on top of hers just before the two finally turned their intertwined bodies against the window and gazed out over the beauty of the Nation’s Capital.

The visceral memory of that forever engrained instant sent yet another orgasmic shockwave ripping through Lisa as Dr. Jerden showed no sign of slowing between her legs. When she finally did ease the clutches of her thigh-grip around his head and pulled the sheets back allowing him to crawl up the length of her body and get some air, she felt a warm and appreciative tremor tingle down her spine seeing the shiny and drenched outline of his facial features smiling back at her.

“Thank You,” she untangled her tongue and managed to say, every nerve in her body jumping when Garrett kissed her softly on the belly button before easing up to suckle from both her raw and throbbing breasts.


The magical interlude lasted until the Sun started to peek itself over the morning horizon, gradually filling the room with enough light to tell both Garrett and Lisa they had places to be, she to her symposium and he to visit with his family.

What the two had shared had been something that was sparked a good 15 years earlier, and both, in the hauntingly frosted glow of the morning sunlight, agreed it had been well worth the wait. The only thing that would perhaps approach the bliss there were feeling as they shared those last few moments embraced in bed would be the naughty secret the two would forever share about what happened in the Amtrak bathroom during the train ride home a few days later.

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