The Freshman

by Ann Douglas

Caution: This Mature Woman/Young Man Sex Story contains strong sexual content, including Ma/Fa, Consensual, Fiction, Oral Sex, mature woman young man sex story, middle-aged woman fucks barely legal, young stud fucks older woman sex story.

Desc: Mature Woman/Young Man Sex Story: Whitney Pennington had one advantage over her fellow students in Late Twentieth Century History. What they only knew from textbooks had been her life.

Whitney Pennington paused outside the classroom and took a deep breath. Like so many other college freshman, the short haired blond found her first day of classes at Northern California State a rushing kaleidoscope of sights and sounds. One that, at times, seemed overwhelming.

She didn't think it possible, but her heart was racing even faster than it had been when she woke up this morning. Too nervous to even try and have breakfast, she'd settled for just a cup of tea to settle her nerves. Whitney couldn't remember the last time she had spent so much time picking out clothes as she had last night. She finally settled on a rather simple yellow blouse and blue skirt. First impressions were always the most important, or so she remembered her mother saying while she was growing up. Not for the first time today, the tall woman wondered if this whole college thing might have been a mistake.

"It's just nerves," Whitney said to herself as she took a second deep breath to calm herself. "I'm sure every college freshman goes through the same thing."

With that, she stepped through the door and into her afternoon history class. What she didn't say to herself was the fact that most nervous freshmen weren't fifty-one years old.

The buzz of conversation stopped for a moment as she stepped into the room. The same thing had happened in English Literature earlier in the day. Most of the eighteen and nineteen year olds mistakenly assumed that she was the Professor and stopped what they were doing. This time, rather than add to the confusion, Whitney quickly moved to the closest empty seat and sat down. This brought a new topic to the conversations as they realized that she was also a student.

A few minutes later, the actual History Professor walked into the room. To Whitney's surprise, even she was at least twenty years younger than the new freshman. She introduced herself as Professor Rodriguez and welcomed them to Late Twentieth Century History.

Whitney listened intently as the Instructor outlined the syllabus for the semester, taking notes of the highlights. The more she listened, the more Whitney thought she was going to like this class. She had always been fascinated by history. If things had gone differently in her life, she might have considered becoming a teacher herself.

But as someone once said much better than she ever could, life was what happened when you were busy making other plans. Whitney had found herself pregnant the summer following high school graduation and back in those days, there was no consideration of not getting married. In 1965, the sexual revolution had yet to come to Greenridge Falls.

As bad as her situation seemed back then, the seventeen year old had it a lot better than the last two girls in town who found themselves in the same predicament. Whitney loved the father of her child, and he loved her. Stephen Pennington had been her very best friend practically since kindergarten. No one even raised an eyebrow when they rushed to the altar.

What followed were three plus decades of married life that saw two more children added to the fold. It was an almost perfect life, one that only ended, in the words of the minister so long ago, "till death do you part."

At fifty, Whitney found herself a widow with three grown children, two of whom were married. To that, she could add three grandchildren, a newborn girl and two teenage boys. Her oldest son, Jack, had grown up working in the family business and easily took over when her husband died.

After a year of just keeping herself busy, Whitney had mentioned to her daughter Diane that she was thinking of taking a few courses at the local University. Something to pass the time and indulge some of her interests. The youngest of her children immediately thought it was a great idea and encouraged her to enroll the very next semester.

"You'll love it," the twenty-six-year-old accountant had said. "You'll have a lot of fun, and think of all the cute guys you'll meet there," she had laughingly added.

Whitney had to laugh as well. Ever since she had hit puberty, Diane had boys on the brain. If you compared photos of Whitney and Diane each at sixteen, you would've thought them sisters rather than mother and daughter. Just as tall as Whitney, Diane had inherited her bust as well. A fact that wasn't lost on the boys in her high school. Her hair was a darker blond than her mother's, but they both had a perpetually cheerful face.

"Sure, I can see them now all lining up to date the old lady," Whitney had laughed in return. "After all, just think how popular someone who can walk into a liquor store and buy beer can be."

Joking aside, Whitney had agreed with her daughter and enrolled for a few courses. Aside from a few moments of hesitation, it had so far been a good experience. By the end of both the class and Professor Rodriguez's introduction, the older woman was glad she hadn't chickened out. Something she had considered a few times.

"Excuse me," a voice from behind Whitney said as the classroom was emptying out. "Are you really a student in this class?"

Whitney turned to face the owner of the voice. A young, clean shaven man with black hair and a baby face. A few inches taller than Whitney, he had the look of an athlete about him.

"Yes I am," Whitney said in a tone that was a little defensive, "believe it or not, I'm a Freshman."

"Oh I didn't mean anything by it," the young man, who Whitney estimated was no more than nineteen, said as he quickly caught the defensive nature of the older woman's tone. "I just thought you might be someone auditing the class, that's all."

"I guess I am being a little defensive," Whitney said in a kinder voice. "Let's start over. I'm Whitney Pennington."

"David Jordan," he said with a warm and wide smile. "It's nice to meet you."

"And it's nice to meet you, David Jordan," Whitney smiled back. "What can I do for you?"

"Well, I asked if you were really a student because if you were, I was wondering if you've given any thought to a study partner for the course?"

"A study partner?" Whitney repeated.

"Yeah, there's a lot of reading in this course and I figured that it would be a lot easier if I had a partner," David went on. "History's never been my best subject and I admit I could use the help. When I saw you I figured you might be a good choice."

"Who better than someone who's lived most of the history that the course covers, right?" Whitney said.

"Oh, I didn't mean it like that," the young man quickly said. "I just saw how you were taking so many notes and figured that you were someone who was going to take this course seriously. Most of the students take this class just to fill the history requirement. I hope to do better than just squeak through."

"Why don't we have a cup of coffee and talk about it?" Whitney suggested. "That is if you don't have another class or anything more pressing at the moment."

"That would be nice," David smiled.

As they walked out of the classroom, Whitney felt that despite their age difference, she had just made a new friend. Not a bad start for her college career.

David, as it turned out, was older than Whitney had first assumed. A sophomore and already twenty-one, he was getting a late start on college life as well. But not as late a start as Whitney, the older woman had laughed.

A star pitcher on his high school baseball team, David had originally planned to go to college on an athletic scholarship. An injury to his shoulder in his senior year had cost him that chance. His arm had since healed, but he'd never regained the speed or accuracy that might have been his ticket to the majors.

Determined to still get an education, the dark-haired young man had gone to work and saved every penny he could to pay his way. Then, finally, David had managed to get enough of a non-athletic scholarship to make up the difference and here he was.


Over the next two months, David and Whitney became good friends. Most times it was easy for Whitney to forget that she was old enough to be David's mother. A frequent visitor to the Pennington household, David struck up a friendship with Diane as well. For a while her maternal instinct took hold and Whitney hoped the friendship between the two young people might lead to something more. But it quickly became apparent that friendship was as far as it was going to go.

Midterm exams appeared on the horizon before they knew it, and Professor Rodriguez lived up to her reputation as one of the hardest graders on campus. When the grades were posted, only a third of the students in her class had passed. Of that third, Whitney and David had the eighth and tenth highest grades, respectively.

"We need to go out and celebrate," David said as he read off the posted grades to Whitney over the telephone late that afternoon.

"I'm afraid my celebrating days are a little behind me," Whitney said as she tried to imagine the wild partying that would be going on in the dorms following all the stress of exam week. "You go and have fun, and then you can tell me all about it."

"It won't be any fun without you," David countered. "I'd have never have passed that test without your help."

What had appeared to be a joke the day he'd asked Whitney to be his study partner, had instead turned out to be their secret edge in class. Having lived many of the events they talked about in class, Whitney brought a personal perspective to the lessons. It was a whole lot easier to learn something when you thought of it as something more than a bunch of lifeless facts and figures from a book.

"Well you helped me enough with my math course," Whitney replied. "It was payment enough for you to tutor me in a class you took last year. Trust me, I'd be really out of place at the dorm parties."

"Forget about the dorm party then," David said. "Let me take you out to dinner, I owe you that at least."

"Well," Whitney hesitated. "I guess that would be all right. But nothing too fancy or expensive. I know you can't afford to just throw money away."

"Great, how about tonight?" David asked excitedly. "I could pick you up about eight."

"Well that is a little short notice," Whitney mused. "But I guess tonight would be fine. Why don't you let me make the reservations?"

David was so excited that he quickly agreed. That pleased Whitney as she had already decided to make the reservations at Alberto's. The owner was an old friend and would be more than happy to make sure that the bill David got in no way reflected the actual cost of the meal. Whitney would pay the difference herself.

"You going out?" Diane asked as she stepped into the kitchen and heard her Mother on the phone with the owner of Alberto's.

"Why yes," Whitney replied. "David wants to thank me for helping him with his midterms by taking me out to dinner."

"Just dinner, huh?" Diane said.

"And what's that supposed to mean?"

"Oh come on, Mom," Diane said as she sat down in the adjacent chair, "you can't tell me you haven't noticed the way he looks at you."

"Don't be ridiculous," Whitney said. "I'm old enough to be his mother."

"But you're not," Diane countered, "and some guys are turned on by things like that."

"You can't think he's considering this a real date?" Whitney said.

"Maybe," Diane mused, "maybe not. But I think you should ask yourself if you consider it a date."

"What?" Whitney said in surprise. "You can't be serious. He's twenty-one years old for goodness sake."

"Last time I looked, that was legally an adult, and then some," Diane grinned.

"Okay, enough is enough," the older woman said. "This is just two friends going out to dinner. That's it."

"If you say so," Diane finally said in an unbelieving voice. "But I'll make sure I knock before waking you up in the morning," she laughed.

With the sound of her laughter still in the air, Diane turned and left the kitchen, leaving her mother even more confused. In the beginning, the fifty-one year old thought her daughter was just joking, then realized that her youngest was quite serious in her suggestions.

Whitney poured the last of her coffee into the sink and rinsed out the cup. Whatever wild fantasies her daughter's imagination might conjure up, Whitney had made a dinner date in a few hours and she had to get ready for it. Dropping the coffee cup into the dishwasher, she headed upstairs to shower and change.

Fifteen minutes later, wrapped in a large white bathrobe, Whitney stepped out of the shower, her body still warm from the heat of the water against her skin. She stepped into her bedroom and sat down at the vanity.

Whitney sat there for a few moments, looking at her reflection in the large mirror. Try as she could, the blond couldn't get her daughter's comments out of her mind. If nothing else, her words had highlighted the absence of sexual satisfaction in her life.

Since her husband's passing, Whitney had only gone out on a few dates, mostly with friends that had also been friends of her husbands. Of these, only one had ended in any sexual activity. She remembered it as being a less than fulfilling experience. At least compared to those she had shared with her husband.

Brushing her hair, Whitney wouldn't have been human if she didn't consider how it might feel to actually act out Diane's fantasy. Many a night she had played with herself as she ran fantasies through her mind. The image of the dark-haired young man filled the center of the mirror before her as she absentmindedly slipped her hand beneath the fold of her robe and stroked the nipple of her breast. A nipple she found erect and hard.

Allowing herself to drift along in the fantasy, Whitney pulled open her robe to allow greater access to her breasts. Dropping her hairbrush onto the vanity, the blond took hold of her other breast as well, her fingers caressing the hard tip.

Whitney had always loved the touch of soft hands on her mounds, be it her own or that of a lover. Nature had been kind to her, gifting her with breasts that were just large enough to be sexually attractive yet also small and firm enough to have successfully endured her years.

Deeper into the fantasy her mind wandered as one of her hands slid from her breast to down between her legs. There to find, despite having just come from the shower, her pubic mound was moist with arousal. Her fingers gently probed within, sending a small tingle inside her.

She closed her eyes and let out a small sigh, picturing in her mind's eyes what David might look like nude. How his body might feel pressed against her own. His hard young cock between her legs, buried deep within her.

"Mom..." came Diane's voice from the doorway of her mother's bedroom.

Snapped out of her erotic musings by the sound of her daughter's voice, Whitney quickly closed her robe. She hoped Diane hadn't noticed what she'd been doing in the reflection of the mirror.

If Diane had noticed the image in the glass, she gave no indication. Whitney turned in her chair to face her, her hands holding her robe tightly closed. Dismissing the last of the carnal imagery from her thoughts, the older woman asked her daughter if something was the matter.

"I just wanted to apologize," Diane said as she stopped at the edge of the vanity. "I think I might've upset you by what I said in the kitchen."

"There's no need to apologize," Whitney smiled at her youngest. "I think I might've overreacted a little. I actually thought you were serious."

"Oh I was serious," Diane said unexpectedly. "I really do think a little fling might do you a world of good. What I'm apologizing for is trying to press you into it. That's something that you should decide on your own."

"You could really see me having a fling with a twenty-one year old boy?" Whitney asked.

"I could see you having a fling with a twenty-one-year-old man," Diane replied, stressing the last word. "I think you deserve to have some adventure in your life. And I know, as sure as I'm standing here, that Dad would've felt the same way."

"You really think that?" Whitney asked. "You really think your father would want me to bed a man younger than any of our children?"

So intent was Diane on answering her mother, she totally missed the fact that David had been upgraded in her mother's question from boy to man.

"I know that he'd want you to be happy with anyone who made you feel good," Diane countered. "You can't tell me you don't enjoy being with David. And not in the same way as you enjoy being with Jack, Billy or me."

With that, Diane left her mother alone once more.

When she thought about it, Whitney had to admit she did enjoy the time she spent with the younger man. When they were alone, it was easy to forget the difference in their ages. In fact, there were times when the twenty-one-year-old seemed more a mature adult then a number of the men currently in her social circle.

"Oh Steve," Whitney asked quietly of the framed photograph on her dresser. "What do you think I should do?"

Of course no answer was forthcoming from the smiling face of her husband, frozen forever in time. But as she looked into the rich blue of her lost love's eyes, it suddenly occurred to Whitney why she got along so well with David. In all the ways that counted, he reminded her so much of Steve Pennington.

"Mom, David is here," Whitney heard Diane call from the bottom of the stairs an hour later.

Taking a final look at herself in the mirror, Whitney said that she would be right down.

"She'll be right down," Diane repeated to David when she walked back into the living room. "Can I get you something while you're waiting?"

"No, I'm fine," David said with a smile.

Diane took a good long look at David, decked out in what had to be his best suit. She had to say, he was looking pretty good. If she couldn't convince her mother that he'd be a good thing for her, the twenty-six-year-old was tempted to find out how good herself.

"I hope I didn't keep you waiting too long," Whitney said as she stepped into the room.

David turned and was about to say not at all, but was struck almost speechless at the sight of his date for the evening. An almost silent wow was all he could manage.

Diane was surprised by her mother's appearance as well. It had been a long time since she'd seen her dressed like this. The rich red dress she wore had been sitting in the back of her closet since before her Dad had died. Whitney had bought it for their twenty-fifth anniversary party.

It was low cut enough to show off her still impressive bust, but proper enough to be respectable. Around her neck she was wearing the string of pearls that once belonged to her grandmother. It was a testament to how well she took care of herself that Whitney could still wear it after all this time.

"Shall we get going?" Whitney asked as she picked up her purse from a small side table. "The reservations were for eight."

"Have fun you two," Diane called out as she watched them walk out the door. "Don't do anything I wouldn't do," she added in a much lower voice.

Whitney paused and looked back, giving her daughter a cautious look.


"Mrs. Pennington, how nice to see you again," Salvatore Alberto beamed when he spotted Whitney coming through the front door of his restaurant. "It's been far too long."

"Thank you, Salvatore," Whitney said with a warm smile. "Has everything been arranged as I asked?"

David was greatly surprised that Whitney had spoken to Mr. Alberto in flawless Italian.

"Of course," the seventy-two year old owner smiled. "Everything is as you requested, my dear. I can guarantee that you and your..."

The old man paused for a moment, unsure of how to refer to her escort. Over the years he had seen a long procession of patrons requesting a quiet dinner with an equally long line of nephews, nieces and younger cousins.

"Friend will do, Salvatore," Whitney filled in the blank.

"Ah yes," he grinned knowingly. "I have personally selected a nice table in the corner..."

"No table in the corner, Salvatore," the blond interrupted. "I'm just having dinner with a classmate. There's no need to give anyone any reason to think it's anything more."

"Not a problem, my dear," Salvatore replied, used to making sudden changes for old customers. "Dominic, please escort Mrs. Pennington and her guest to table four," he said to the waiter at his elbow.

"Is there a problem?" David asked Whitney, unable to follow the conversation in Italian.

"Not at all," Whitney explained. "Mr. Alberto and I are old friends. We were just talking a moment to catch up, that's all."

"Oh," David replied as he followed Whitney and Dominic to their table.

The conversation over dinner was almost better than the food, which as always was first rate. Whitney couldn't remember the last time she had enjoyed herself more. Certainly not with the last two men she'd been to dinner with.

"That was a great meal," David said as he gently pushed the now empty plate away from him. "I really enjoyed it."

"Yes it was," Whitney agreed. "it was almost as good as the company."

David blushed at the compliment. A look of embarrassment that threatened to become all too real as Dominic appeared at his side. In his hand he held a small leather folder containing the check.

David figured this little celebration was going to take all of his emergency cash. Now that it was over, he didn't really mind.

His eyes lit up as he saw the total at the bottom of the check. It had to be an error.

Now it was Whitney's turn to ask if there was something wrong.

"No, nothing's wrong," David said, a grin on his face. "In fact, I think everything's pretty right."

Whitney just smiled as he paid the bill.

"Well it's still early," David said as they pulled away from the restaurant, "would you like to do anything else?"

"Well it is almost nine-thirty," Whitney said as she glanced at the dashboard clock, "an old woman like myself does need her sleep."

"Oh, okay," a confused David replied.

"Honey, I'm only kidding," Whitney laughed. "I've been known to stay up almost till the end of the eleven o'clock news."

David now laughed as he realized she was playing with him.

"What would you like to do?" Whitney said. "We are, after all, supposed to be out celebrating."

"Well, I guess we could catch a movie at the multiplex," David suggested.

"Oh it's much too nice a night to be cooped up in a stuffy movie theater," Whitney replied. "Why don't we go for a drive along the lake. I remember it being especially lovely this time of year."

"Okay, the lake it is," David smiled, glad that the night wasn't coming to an early end.

A half hour later, they were driving along Lakeshore Drive and Whitney found the fresh air to be as invigorating as she remembered it. It had been a long time since she'd come this way.

"There's a small turn off just ahead," she said as she pointed to David's left. "At least there used to be. If it's still there, turn onto it. There should be a nice outcropping where we can park. The view is magnificent."

Less than a minute later, an open dirt road appeared to the left and David turned on to it. As Whitney had remembered, it led up to a clearing with an unobstructed hundred and eighty degree view of the open lake.

"Wow," David exclaimed as he put the car into park, "this is really beautiful."

"Yes it is," Whitney agreed. "More lovely than I remembered."

"Did you come up here a lot?" a curious David asked.

"You could say that," Whitney replied. "I think the first time I ever came up here I was even younger than you."

"Thank you for showing it to me," David said, his attention fixed on the vista before them.

"There's a path down to the water," Whitney remembered. "Let's take a walk."

Guided by the light of the full moon, the two of them made their way down the path to the shoreline. Whitney took off her shoes and walked barefoot onto the small beach. A gentle wave splashed up onto the sand and over her feet.

"It's been a long time since I've done that too," she laughed.

Reluctant to get himself wet, David instead sat down on one of the large rocks that framed the small beach. He watched as Whitney stared out into the darkness.

"David," Whitney said, "how do you see me?"

"Excuse me," he responded.

"How do you see me?" she repeated. "What am I to you?"

"My friend," the twenty-one-year-old said without hesitation.

"Just a friend?" she asked further.

"I don't understand," David replied.

Whitney turned and walked out of the surf to sit next to David on the rock.

"My daughter seems to think that you might have a thing for me," Whitney said.

"A thing?"

"An attraction," she clarified.

"Oh."

"Do you?" Whitney asked.

"I guess maybe I do," David said after a few moments hesitation.

"But..." Whitney added as she sensed there was more.

David seemed reluctant to explain further.

"I won't be offended by anything you say," Whitney offered. "As you've probably noticed, I'm a real big girl."

"I am attracted to you," David said. "I think about you a lot. Even though I know I shouldn't."

"You're going to have to explain that one to me," Whitney said.

"I..." he began, then hesitated. "I can't."

Whitney placed her hand on his shoulder and spoke softly.

"David, do you have sexual fantasies about me?" she asked.

"Yes," he answered almost inaudibly, as even in the dim light she could see his face turning a bright red.

"Honey, there's nothing wrong with that," Whitney said reassuringly.

He didn't seem convinced.

"Would it make you feel any better if I told you I've had erotic daydreams about you too?"

David looked at Whitney in disbelief. It never occurred to him that she could possibly have the same feelings, the same desires.

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