A Train Ride to Remember

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A college student meets an older woman on a train.
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136 Followers

"Time!! Please put your pencils down and pass your examination booklets to the front of the room. Hope to see all of you next semester," the professor exclaimed.

Having just completed his last exam of his first semester of college, Parker was overwhelmed with joy. He had spent the majority of the semester working up to that moment, spending endless hours in the library instead of partying like most freshmen. Parker kept telling himself that it would all be worth it after graduating when he lands a great investment banking job.

Without hesitating, Parker packed up his calculator and pencils. He was out of the classroom door within seconds. Cruising down the quad and taking a shortcut through the library, he was headed towards his dorm room. Before the exam, he had spent the majority of the morning packing his stuff to bring home to New York for December break.

"Hey dude, I'm heading home," Parker told him roommate. "I'll be back the weekend before classes start up again."

"Damn man. Your finals schedule was ridiculous," his roommate responded. The college scheduled finals for a 2 week period at the end of each semester. Parker, by pure luck of scheduling, was done in the first 3 days.

He picked up his duffel bag full of dirty laundry and headed to the bus stop. Parker was headed towards Boston's South Station to catch an Amtrak train. On the bus ride he reflected on how his semester went.

"Fuck. I barely accomplished any of my goals this semester," Parker thought to himself. "What's the point in going away to college if I'm not going to enjoy it?"

Number one on the list of things unaccomplished was getting laid. He had only had sex once before, with a girl he met the summer before college began. But it went so horribly that Parker needed a new chance to redeem himself.

Between his constant study habits and his quiet demeanor, he didn't meet a lot of girls. He was actually a decent looking young man though. His body was relatively athletic due to four years of high school soccer. He had a nice tan which complemented his big brown eyes and dark brown wavy hair. But unless a girl was going to jump on top of him in the library, he wasn't getting laid anytime soon.

Arriving at South Station, Parker looked up at the departure board to see when the next train was leaving - Regional Service to New York's Penn Station. Luckily, the train was almost ready to leave, so Parker rushed to the window and bought a reserved coach ticket.

The train was near empty since it was midweek morning. Parker's finals schedule was paying off, since the train would likely have been packed a week later with everyone traveling for the holidays. Inside the car, there were perhaps ten other people scattered around. Parker found his assigned window seat midway down the car. He got comfortable and was ready for the train to start moving.

Right as the train was pulling out of the station, Parker felt a shadow over him. He looked up to see the figure of a woman standing in the aisle putting her luggage onto the overhead racks. The woman gave Parker a smug little smile and sat down next to him. Parker was too annoyed to look directly at her. His first thought was that the train was pretty empty, and that even though everyone had assigned seats it probably would be fine if she moved elsewhere. That way he wouldn't feel so claustrophobic and both of them would be much more comfortable. But he was too afraid to say anything.

Then she crossed her legs. Parker, without thinking, glanced down to see a nicely tanned and rather toned thigh. Suddenly, she was much more welcome to sit with him if she wanted.

Trying not to make it too obvious, for the first couple minutes of the train ride the young man snuck glimpses down at her legs. Occasionally she would ever so slightly shift her body weight, raising her dark blue skirt revealing a tiny bit more of her thigh. While she was looking down at a woman's magazine, Parker felt compelled to get a better look at her face.

Ever so casually, he looked directly at her and was quite surprised. While he was expecting a woman in her 20's or 30's, here was something completely different. She was much older, probably closer to 50. But she looked great for her age. Her shoulder length brunette hair surrounded the soft tanned skin of her face, only slightly showing lines that revealed her true age. She had a youthfulness about her, while still showing that she was clearly a mature woman.

Parker pulled out a magazine and pretended to read it in between glances at her firm legs. The magazine also helped in disguising the stiffening of his cock in his pants.

Suddenly, out of the blue, the woman looks over at Parker. She opens her mouth and asks, "Do you know how long this train takes to get to New York?"

Dumbfounded that she was talking to him he quickly looked up from his magazine and managed to get out the phrase, "Umm what?"

"How long does this train take to get to New York?" she replied.

"Oh. Well like 4 hours."

"Shit. I'm going to miss my meeting," the woman started speaking frantically." I knew I should have flown. This was such a stupid idea. If I don't please these clients I know I'm going to get fired. I just know it...And then what the hell am I doing to do with myself?"

Parker stared at her not knowing what to say, or even if he was supposed to say anything at all. It was a rather awkward position that he was in. The woman closed her eyes and took a deep breathe. She looked back at Parker, who looked like a deer in headlights.

She said, "I'm really sorry. I didn't mean to freak out like that on you."

"Not to worry. It happens to the best of us."

"Thanks. I'm Jane."

"Parker." He reached his hand out to shake hers, overjoyed at being able to touch her soft skin.

"Lovely to meet you Parker."

Jane uncrossed her legs and moved her body to better face the boy. It was apparent the woman's legs weren't her only great feature. In the split second that Parker moved his body towards her, he managed to catch a peek at what appeared to be an ounce of cleavage showing. Without making it too obvious, he adjusted his body again to get another quick look.

She wore a white and blue striped button-down blouse. With the top button undone, a little of her large natural looking breasts peered through. As Jane spoke she ever so slightly leaned towards the young man, as a person who was genuinely interested in the conversation would do. Parker attempted to do his best to keep the conversation going while trying not to look too noticeable with his downward gazes.

It was pretty mild, casual conversation. He explained his academic life while she discussed her career in advertising sales. Both seemed content with having a conversation to pass the time on an otherwise dull train ride. Plus Parker was pretty excited by the short glimpses he could sneak at this other woman's body.

At one point, Parker attempted to suavely look downwards at Jane's magnificent legs. He waited for a short break in conversation when he knew she wasn't looking directly at him. His eyes glanced as far down as they could without moving his head, which would have been too obvious of his intent. When his pupils finally reached their destination, Parker was treated to a fantastic view of Jane' toned thighs.

Her legs still uncrossed, Parker followed them up with his eyes from her feet to her knees, all the way to her skirt. Suddenly, his heart started pounded uncontrollably because in amazement he realized her could see up her skirt to her inner thigh. His erection, which never completely went away, was now hard as ever.

Parker looked back up at Jane's face, who apparently was already staring right at him. Immediately Parker assumed the worst.

He thought to himself, "Damn it!! She definitely caught me staring at her. I'm such an idiot. She's probably totally creeped out now."

Parker turned away because he couldn't bear to look Jane in the eyes.

After what seemed to be an eternity to the boy, Jane finally opened her mouth and said, "So what do you want to do after college?"

"Umm. Go work on Wall Street," Parker barely mumbled out.

"Oh really? I'm sure you'll be very good at that."

In his mind Parker was freaking out because he didn't know whether he has been caught or not. Was she playing it off that she didn't see? Or maybe she didn't care? All he knew was that he wasn't going to take any more chances, which meant no more cheap views.

As the conversation continued, it was apparent that Jane wasn't going to make any reference to Parker staring at her. About half an hour into the ride, the train rolled into the Providence train station. A couple of new people got onto the train, but very few ended up sitting in the car Parker was in.

"I'm kind of cold," Jane said to Parker. "I should get my fleece blanket from my suitcase."

The woman turned towards the aisle and stood up. She reached up towards the overhead bin to try to get to her luggage. It had shifted while the train was moving, so it was now deeper into the compartment. Not being very tall, on her first attempt she realized it was too far to grasp.

Her next attempt, Jane stood on her toes to better reach. As she did, Parker started to take notice. The further she would extent her body, the higher her skirt would rise. Parker couldn't help himself but to look. By the time she was finally able to grasp her suitcase her skirt allowed for a fantastic view of her silky smooth legs. Suddenly, Parker got a millisecond glimpse of what appeared to be red panties.

"There we go," Jane said as she was able to finally come down with a blue fleece blanket. She unfolded and covered herself with it.

Disappointed, Parker thought to himself, "Fuck. Now I can't see anything. I guess sneaking peaks was fun while it lasted."

"Parker, I'm being rude. You're probably cold too. You are welcome to share my blanket with me."

"Oh thanks Jane. I appreciate it." He cast a smile in her direction. The truth was that he wasn't cold, but he just wanted to be closer to her body.

Lucky for him, the blanket wasn't terribly large, which meant both of them shifted closer to each other. Their arms touched as they both shared the armrest between the seats. On more than one occasion Parker felt her left breast rub against his bicep as she shifted position.

The train plowed through Hartford, Connecticut. Parker was starting to get extremely horny from all the cheap feels. His cock jumped slightly each time he felt her tits touch his body. The blanket helped well to conceal his raging hard-on, as he no longer had the need to put in the extra effort to hide it.

Conversation between the two was pretty casual. Jane mostly was asking about his life at school.

"So how are the ladies treating you?" Jane inquired.

Parker looked away from Jane's glare and responded, "I do all right for myself. No complaints."

"You are such a liar!! Parker, I can always tell when people are lying."

"No really, I do okay."

"Parker, I'm in marketing. It's my job to lie to people all day long. I know when people are exaggerating the truth."

"Well, what about you? Are you married? I don't see a ring on your finger."

"Divorced. It happened last year. I found him in our bedroom with a coworker. I was away for a business trip and I came home a day early. You can imagine my surprise when I opened the front door and heard moaning."

"Oh my god, I'm so sorry Jane. You deserve someone who will treat you right."

"You're so sweet for saying that."

Both of their arms still resting on the armrest, she moved her hand on top of his. Parker was surprised by the physical contact, but he tried not to let himself become too nervous. She squeezed his hand slightly, and started gently rubbing the digits of his fingers. Speechless, Parker gazed down to the blanket where his hand was being held. Meanwhile, Jane was staring right into Parkers eyes.

Jane opened her mouth to say, "You really are a sweet guy."

"Um thanks I guess."

"No, you really are. You should never change that about you."

Without notice, Jane lifted Parker's hand off of the armrest. Still in her grasp, she moved both of their hands towards his body. Jane rested their hands on Parker's knee. He looked up into her eyes. She looked down towards his crotch.

Her nails gently dug into his skin as she moved her hand towards Parker's inner thigh. Parker let his hand drop to his side. She began to rub back and forth, inching closer towards his fully erect cock. Parker's breathing became much deeper and his heart was pounding faster than ever. As both were staring at what was occurring in Parker's lap, Jane turned her head and softly blew into his ear.

The older woman's hand casually brushed over the top of Parker's raging hard on. On her second pass over his crotch, her fingers came to rest on the zipper of his jeans. With the palm of her hand, Jane began to press downward rubbing his penis through his clothing. Parker let out a quiet gasp. She continued to massage, feeling the outline of his stiff member in her hand.

"Let's see what we've got here," Jane whispered into his ear.

She pulled at one end of Parker's brown belt, yanking it through the loops and out of the buckle. With the side of her tits pushing against his body, she leaned closer to unbutton his jeans.

A rather audible zipping noise came from Parker's crotch. Already nervous, Parker was extremely worried that another passenger may have heard his pants being unzipped. He raised his head above the seats to see if any of the other people on the train were suspicious. Luckily for the two of them, the only people in the car appeared to be sleeping or reading.

Jane maneuvered her fingers through the hole of Parker's boxer shorts. She came to rest on the flesh of his penis. With each of her fingers one by one, starting with the pinky, she slowly wrapped them around his cock until she had a firm hold. Parker looked towards Jane as her tongue sensually licked her upper lip.

"Nice cock you have there," Jane quietly exclaimed as she snuck a peek under the blanket to get a look at it.

"Heh. Thanks." It was only thing that Parker could get out of his mouth.

Fully grasped in her right hand, Jane started jerking Parker's cock up and down. She began slow but sped up as time went on. There were several moments when Parker needed to adjust the fleece blanket as it started to fall to the floor. One instance in particular, Jane gave a rather violent tug, sending the blanket flying and leaving Parker exposed to the world for several seconds.

The train made a stop at New Haven, Connecticut. The conductor walked down the aisle towards the couple. Jane stopped what she was doing and the two moved their bodies further apart. The conductor continued straight passed the two, and moved on to another car. A man and a woman got up from their seats and exited the train, leaving about four or five others still in the car. Parker was relieved when he heard the doors closed and no one new got on the train.

Jane leaned in closer to Parker again. Her face pushed up against his, she licked his ear lobe.

She whispered in a sensual voice, "I love the way your young cock feels in my hand. I haven't seen a dick like yours in years."

Parker smiled. Somehow he mustered up the courage to say, "Can I see your pussy?"

Jane looked towards him and let out a little laugh. "Of course you can, baby."

She did a quick look around of her surrounding to see if any of the other passengers were paying attention. The remaining people on the train all looked half dead. No one was talking, and those that were awake were far enough away that they couldn't be aware of the debauchery that was occurring between Parker and Jane.

In one quick motion and without much notice, Jane lifted her body up and reached up her skirt. She grabbed a hold of both sides of her panties and in a flash pulled them down towards her ankles. Sitting on the ground were a pair of red silk panties that Parker had only seen a glimpse of before. Jane picked them up and stuck them in the seat between them so that no one else would see.

She lifted the blanket slightly in Parker's direction so he could have a peek. His eyes lit up as he stared down at her completely shaven pussy. Jane took his right hand and moved it towards her mouth. His fingers came to rest on her full lips. Jane opened her mouth and licked his middle finder. The top digitals of his finger entered between her lips, and Parker felt a warm sucking sensation. After several seconds, she pulled his finger out her mouth.

Jane looked into Parker's eyes and whispered, "Go for it." She looked down towards her pussy and up into his eyes again.

Fear started mounting in Parker, as his inexperience was making him extremely nervous. Even though he had watched a significant amount of porn, he was not quite sure exactly what to do next.

"Come on Parker. My pussy is waiting for you."

Even if he didn't know what to do, he knew he had to do something. Almost in slow motion, Parker hand rested on Jane's thigh and glided closer to her twat. Finally it rests between her legs. He gently touched the lips of her pussy. His middle finger lightly flicked her clit. Jane let out a soft sigh, so Parker knew he has to be doing something right.

Parker started moving his finger around her clit quicker noticing Jane's positive reactions. Her sighs started to get deeper and louder as time went on. He looked up towards her face to see she was desperately trying to bite her lip to suppress the noises coming from her mouth. After a couple minutes, eventually she had to pull his hand away since the fear of getting caught was getting too great.

"Did I do something wrong?" Parker said, obviously self-conscious of his inexperience.

"Not at all, baby. That was great. I just couldn't keep quiet enough so no one would hear us."

The train pulled into the station at New Haven, Connecticut. Several people entered the car in which the two were sitting. An elder gentleman walked down the aisle towards them. He gave a friendly smile to the pair as he passed. The blanket did well to cover up any inappropriate activity below. He eventually took a seat not far away. Several others would take seats nearby.

Parker whispered, "Well I guess that ends our fun."

She looked around the train to assess the situation. "Well not necessarily. I think I have a plan." Jane had a sneaky looking grin on her face. "Follow me."

Jane adjusted her skirt and got up from her seat. She began to walk down the aisle. Parker was a little apprehensive about having to stand up. After putting his cock back inside his jeans there was an obvious bulge for the world to see. Jane looked back to see what the holdup was, and motioned with her head for him to follow. He moved quickly towards her hoping no one would notice.

Towards the end of the car, Jane stopped walking. She looked around to see if anyone was paying attention. Everyone looked half dead. Jane grabbed Parker's hand, opened the door to the nearby handicapped bathroom, and pulled him in. She immediately shut and locked the door behind them.

The bathroom was large enough that it allowed for some room for the two of them. In one corner was a stainless steel toilet, and there was a small matching sink on the other side.

"Finally we have some privacy," Jane said. All Parker could get out of his mouth was a nervous laugh. "Parker, you are adorable. It's so nice of you being with an old lady like me."

"Come on Jane, you don't even look that old." With some trepidation he said, "I think you're actually pretty hot."

"Aw you are so sweet." She put her hands on his chest and moved in closer to him. Looking directly into his eyes she kissed him full on the lips. Parker put his hands on her waist and gave her a long passionate kiss back.

sb69
sb69
136 Followers
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