The Freshman

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Ann Douglas
Ann Douglas
3,178 Followers

"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 blonde 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," David 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.

"I have it on no less an authority than my daughter, Diane, that it's quite common for young men to have sexual fantasies about older women," Whitney said. "And in that same thinking, I'm sure it's not that unusual for a mature woman like me to have a fantasy or two about a young man like you."

"I don't know what to say," David said.

"Don't say anything then," Whitney whispered as she took David's face in her hands and kissed him.

It was not the sort of kiss you normally expected to see a fifty-one year old woman give a young man less than half her age. Whitney's tongue invaded David's mouth with a vengeance, exploring the soft wetness found there. After a moment's hesitation, David responded in turn. He couldn't believe the stuff of his secret fantasies might actually be coming true.

"That was nice," Whitney smiled as they broke the kiss.

"Yes it was," David agreed a little sheepishly, feeling like he was a sixteen year old on his first date.

"Shall we try that again?" Whitney asked.

"Oh yes," David agreed.

If anything, the second kiss was even more intense as Whitney took David's hand and pressed it to her breast. As their lips parted again, she pulled his head down to where his hand had rested. His nostrils filling with the sweet aroma of the perfume Whitney had earlier splashed there, David kissed the soft exposed area of her supple mounds. His tongue explored the depths of her cleavage as he felt the softness of her hand come to rest on the hardness of his cock. For a few seconds, the young man worried that he might actually come in his pants.

"While this wouldn't be the first time I've done it in the woods," Whitney said as she rubbed his cock ever so slightly, "I'm sure we could find someplace a little more comfortable."

David nodded his head in agreement, unable to find his voice as he realized how far Whitney was willing to take what was happening.

"Didn't we pass a motel a few miles back?" Whitney asked rhetorically. "I'm sure we could find a empty room."

"Yes," David managed to say.

Almost amused by the young man's discomfort, Whitney suggested that she drive.

David barely said a word on the five minute drive back to the motel, silently staring instead at the beautiful woman sitting beside him. Whitney considered the idea that perhaps she was going too far too fast as she glanced back at the young man. Then as quickly as the thought appeared, she dismissed it. Too many times in the last twenty months she had let things go too slow.

Pulling into the parking lot, she was glad to see the vacancy sign at the entrance of the small motel lit up. She would've really hated to have to drive all the way back into town.

"Should I go and get us a room?" David asked as they came to a stop, his excitement finally subsiding enough for him to act his age.

"Only if you let me pay for it," Whitney replied. "After all, this was my idea."

With that she handed him a few bills from her purse and watched as he practically raced to the management office. Sitting in silence for the brief time David was gone, Whitney felt more excited than she had for ages. It had been a long time since she'd had a sexual adventure.

"Room nine," David said as he came back to the car. "It's right over there."

Locking the car door behind her, Whitney followed David the short distance to the last room at the end of a long row.

The motel hadn't been here the last time Whitney visited the lake. She had once overheard Diane and a few of her girlfriends talking about it back when they were in high school. Imagining what kind of dump it must be, Whitney had told Diane that if she had to have a place to go with a boy, she'd rather they'd use the small apartment over the garage. There was no way she was going to keep her daughter from sleeping with her boyfriends if that was what she wanted to do, but at least Whitney could make sure they had a safe, clean place to do it in.

Most of the guests who registered at the Lakeview Motel were those referred to as "short stay guests". Usually married men with women not their wives, or young unmarrieds who for one reason or another didn't have a place of their own to go. The illicit nature of the clientele seemed to add to the excitement of the moment.

The room was better than she expected out here in the middle of nowhere. Filled with your basic motel furniture, it looked as nice as any other Whitney had been in over the years. All she really hoped for was for it to be clean and private, so finding it like this was definitely a bonus.

"It's a nice room," David said for lack of anything else.

"Yes it is," Whitney agreed.

Whitney couldn't help but wonder if the young man would be as nervous as he appeared to be if he was here with a woman his own age. She knew from their talks that he wasn't a virgin, having had the normal share of girlfriends in high school and his first year of college.

"Maybe," she thought as she excused herself to use the restroom, "that's part of what he fantasizes about. The more experienced older woman and the inexperienced young man."

When she reemerged from the bathroom, Whitney was only wearing a bra and panties, having left the rest of her clothes carefully folded on the vanity. Both undergarments were black lace and designed more to display than conceal. Whitney wasn't sure what possessed her to put on something so scandalous when she was getting dressed. She just knew she didn't want to wear the boring plain whites that were her normal fare.

"I hope you're not too disappointed," Whitney said as struck a pose, putting her best assets forward.

"You're beautiful," David said breathlessly.

"Well let's just say that I'm not in bad shape for a lady my age," Whitney laughed as she stepped over and put her arms around him.

The kiss she gave him was brief, with just a glimpse of her tongue passing between his lips. She held him tight for a few moments more, then took a step back.

"Why don't we make you a little more comfortable," Whitney said as she undid his tie and then the buttons of his shirt.

When his shirt was half undone, Whitney kissed the small area of his chest visible in the opening of his v-neck T-shirt. Nearly hairless, his chest was hard and smooth. Once his shirt was gone, the v-neck followed.

Fingers outstretched, Whitney ran her long red nails across David's chest, playing with his small male nipples as she passed over them. On a playful impulse, she leaned over and kissed each of them, using her nimble tongue to tickle the tips. Her late husband had loved it when she played with his nipples. From the look on his face, it was apparent that David shared that enjoyment.

As if to even the odds, David in turn reached up and undid the front clasp of her bra. The lacy nature of the undergarment had allowed a good look at both her hidden flesh and areole, but once the thin material fell away they were revealed in all their splendor.

David wasted not a moment in placing a hand beneath each of her breasts, lifting them one at a time to his mouth. Using his lips and eager tongue, the young man covered her mounds with wet caresses.

"Mmmmm, that feels nice," Whitney said, meaning every word.

As much as she wanted to continue and finish undressing her young lover, she waited and let him have his fun. Ever since she first developed, she knew her breasts fascinated men.

Whitney eased herself back and sat down on the edge of the bed, guiding David next to her. It was a much more comfortable position for him to play with her breasts. With his hands, mouth and tongue, the young man massaged her mounds, taking the thick nipples between his lips again and again. Whitney stroked the back of his head, playing with his dark hair and mouthing words of encouragement. All the while she could feel herself becoming wetter and wetter between her legs.

Whitney guided David back up to his feet and undid first his belt, then the button and zipper of his pants. With a strong grip on the waistband, she pulled on his pants with enough force to send them dropping down to his ankles. A thin smile formed on her lips as she focused on the thick bulge beneath his white cotton briefs.

The blonde-haired woman ran two long outstretched fingers over his hardness, outlining it with her nails. Leaning forward to kiss it, she left the imprint of her lipstick on the white material. Then, just as she had done with his pants, she pulled his briefs down to his ankles.

Freed from the restraint of his briefs, David's cock sprang to attention. Six inches long and slim, it was a monument to young manhood. Enthralled by its beauty, Whitney kissed the base of it, then the shaft, and finally the tip. She wrapped her fingers around the base and ran her tongue up and down its length, drawing soft sighs from David. Sighs that quickly grew to a loud moan a few moments later as Whitney took his cock deep into her mouth.

"Oh God!" David exclaimed as he felt his cock enveloped by the rich wetness of her mouth.

More than three decades of experience took hold as Whitney drew David's manhood deeper and deeper within her. Faster and faster, she moved her head back and forth, sliding his cock in and out of her mouth, using both her tongue and lips to drive him to ecstasy. Strong fingers gripped his ass as she held him tight against her, swallowing almost his full length.

Whitney could feel the weakness in his legs and the building tremor in the rest of his body as his orgasm desperately sought release. A release that came a half dozen heartbeats later with an explosion of whiteness into Whitney's waiting mouth.

Even as David erupted into her throat, Whitney pulled him tighter against her, as not to miss of single spurt of his nectar. It was a treat that she had long denied herself. She continued to suck his young manhood until it had no more to give. Still semi-erect, it slipped out from between her lips. Whitney took the time to lick the last remnants of her efforts from its length and kiss the tip of it once last time.

"Did you enjoy that?" Whitney asked as she sat upright on the bed, knowing full well that of course he had.

"No one," David said as he stood naked in front of her, "has ever made me feel like that before."

The praise made Whitney smile. It had hardly been David's first blow job, but it was obvious he thought it was certainly the best. After so many years of practice, Whitney had learned her skills well.

Pulling David close to her once more, Whitney took his hand in hers and pressed it between her legs. He could fell the wetness through the thin material of her panties. Their lips met softly as he began rubbing her pussy with outstretched fingers. As he massaged the damp mound, a quiet cry erupted from Whitney's lips.

"That feels good," she said.

"I hope I can make it feel better," David replied. With that he slid his hand beneath the thin elastic and down against Whitney's wet bush. His fingers quickly found her clit and rubbed against it as well. This brought an even louder response from Whitney.

With Whitney still sitting on the edge of the bed, David lifted her legs and pulled off her panties. Dropping them to the carpeted floor, he ran his hands up along the length of her legs and then back again. He spread them apart, giving him a perfect view of the hairy blonde mound between them.

Without a further word, David dropped to his knees and replaced his hand with his mouth. An eager tongue darted out from his lips and slid between the folds of Whitney's sex. Up and down it traveled its length, savoring its flavor and spreading some of the excitement that filled the young man throughout the woman's reclining form.

"Oh baby, yes," Whitney said as she closed her eyes and enjoyed the sensation, intertwining her fingers across the back of David's head. "Right there, right there, that's so good."

Despite his lack of years, it was quickly obvious to Whitney that David was that rarest of finds. A man who truly loved to go down on a woman and was also good at it. He lifted her legs and draped them over his shoulders, giving him even greater access to her prize.

As waves of erotic delight rippled across her body, Whitney had to wonder why, with a talent as obvious as this, David didn't have rows of girls lined up to go out with him. Then she remembered her daughter's comment that some guys only got turned on by older women. Whatever the reason, she just wanted to lay back and enjoy it, hoping it would just go on and on.

Faster and faster David's gifted tongue and mouth devoured Whitney's pussy, driving her into a state of rapture. Passions long dormant rose to the surface with a vengeance, melting years off her.

"Fuck me!" Whitney called out as she writhed in a orgasmic build up, the likes of which she hadn't felt since she was a newlywed. "Fuck me with your tongue!"

As much as David loved making love to a woman with his tongue, he had a greater desire as far as Whitney was concerned. Pulling his head back from her saturated mound, he stood up and grabbed hold of his cock. With a single fluid motion, he plunged the hard manhood into Whitney's blondee framed pussy. An entry made all the easier by the copious amount of lubricants his prior efforts had produced.

"Oh God!" Whitney called out in a cry loud enough to be heard two rooms away as she felt David's cock fill her.

Loud as the outcry was, it hardly registered in David's ears. He was too intent on what he was doing. Wrapping Whitney's legs around his waist, the dark-haired young man lifted her off the bed and took hold of the cheeks of her ass. Whitney in turn wrapped her arms around David's neck, rising up and down on his cock as she did.

It had been too long since she'd felt a man inside her, at least in such an aggressive manner. Her one instance of lovemaking in the many months since her husband's death had been a rather bland encounter in the missionary position. One that convinced her that if that was the best she could hope for, then she wasn't missing anything.

Ann Douglas
Ann Douglas
3,178 Followers