A House Full of Women Ch. 01

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45-year-old Jack gets it on with a college virgin.
6.1k words
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Part 1 of the 7 part series

Updated 06/11/2023
Created 11/06/2021
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Jack Martin couldn't believe the letter he received from his alma mater.

It seems that, twenty-three years ago, when Jack graduated from the small liberal arts college in Southern California he had attended, he had actually failed to fulfill one of the requirements for graduation. He had taken an English class and had dropped out about midway through the semester. The result was that he had taken an Incomplete in that course, and as a result he was not only short of credits for graduation but, because he was an English major, also short of credits in his chosen field. It hardly mattered that Jack was now a successful insurance agent; his degree was technically invalid, and in order to have a legitimate degree he would either have to take that class again or take an equivalent class.

Jack just laughed when he first read the letter, thinking it must be some sort of joke. But it was clearly written on official stationery from the college's bursar, so it must be authentic. Making a few quick phone calls, Jack learned that the class he had taken decades ago was no longer being offered, so he decided to sign up for another class offered by the English department--a class on Hemingway designed mostly for juniors and seniors. He chose this largely because it was held in the late afternoon, so that he could take off from his office late in the day without losing too much business. It began in January (the commencement of second semester) and would finish in May.

What the other students would say when a forty-five-year-old businessman wandered into the classroom, he could only guess. But he found out pretty soon.

The class was, to his surprise, taught by a woman. Somehow he thought Hemingway was radioactive to women, given the aggressively masculine tendencies of most of his work. Not only that, the teacher--sorry, professor--seemed a few years younger than Jack.

This was going to be a bit of a trial.

The professor, Colleen Jameson, couldn't help putting Jack on the spot from almost the moment the class started. As he shuffled in, sitting discreetly in the back, she eyed him with a smirk and said, "Well, class, we have an unusual student among us, one"--she looked down at a sheet of paper on a clipboard--"Jack Martin, Class of 1997. Jack is here to do a little remedial work. He may be a little out of practice in a college setting, but no doubt his life experience will enlighten us all."

There were a fair number of chuckles at the middle-aged, gray-at-the-temples man who was trying desperately not to be noticed by this gaggle of students, any one of whom could have been his children.

And Jack ran into immediate difficulties once the class got underway. The manner of instruction was not at all what he was used to, and the discussion relentlessly focused on issues of race, class, and gender rather than the flow of the narrative or the distinctive language Hemingway had evolved.

One classmate took immediate pity on Jack. This was Vanessa Claiborne.

The definition of the word "demure" could have been devised with her in mind. A slender, almost waif-like twenty-year-old with flowing blond hair and only modest curves at bust and hips, she had a constantly wide-eyed expression that suggested both surprise and a hint of fear. Although she contributed a lot to the class discussion, she tended to drop her eyes whenever she spoke to a specific person. Her voice was high and soft, and she never raised it.

But her heart ached to see this older man floundering in a setting he was clearly unfamiliar with after all these years. She could tell he was getting more and more frustrated. So, one day after class, she managed to overcome her innate shyness and sidle up to Jack, saying: "Sir, may I help you?"

The expression was ambiguous, so Jack said, "Help me how?"

"Well," Vanessa said, blushing a little, "it just seems to me that you need a little guidance about how things are done now. I--I hope you don't think I'm speaking out of turn, sir."

Jack gazed on this lovely, delicate creature. "Good Lord, no! And none of this 'sir' business. I'm just a student like everyone else. You can call me Jack."

"Okay . . . Jack," she said with a smile that sent a dagger into Jack's heart.

But their initial attempt at a "study date" didn't go so well. They tried sitting down in a coffee shop, but it rapidly filled up with noisy students. They then fled to the college library, but this place--once a hushed cloister dedicated to the worship of the printed word--had now been transformed into a high-tech zone where laptops buzzed and beeped, and where specifically designated "group study areas" were just as noisy as that coffee shop was.

In desperation, Jack said, "Um, Vanessa, I don't suppose you'd care to do our studying at"--his voice suddenly descended to a whisper--"my house?"

"Your house?" Vanessa said with a gulp.

"I live only a few blocks away. I've been there for many years."

With her patented glance at the floor, she said, "Your wife probably wouldn't want me there, even for studying."

Jack glanced down at the naïve young girl--a petite five foot two to his five foot nine. "I don't have a wife, Vanessa--not anymore."

She finally raised her eyes to him, but they were filled with alarm. She was unable to speak.

"If you'd rather not," Jack added hastily, "we could just forget about the whole thing. I'm sure I can manage somehow without your help."

"No, no," Vanessa said, shaking her head. "I'm just being silly."

"I don't want to put you in an uncomfortable situation."

"It's fine, really it is. Which way do we go?"

So they tramped to Jack's house, which was literally a five-minute walk from campus. It was a pretty large place: two stories and a basement, four bedrooms and two and a half baths, and built in the 1940s--which, for this part of the country, made it count as ancient.

"Wow," Vanessa breathed as she wandered into the house, dumping her backpack on the sofa in the living room, "what a huge house! You live here all by yourself?"

Vanessa immediately realized she'd made a faux pas. You didn't use to live her all by yourself--you had a wife once.

"Well, I have a lot of stuff," Jack said, even though the place was anything but a hoarder's paradise. It was in fact austerely but tastefully furnished, and Vanessa had to resist lapsing into the sexist assumption that it was Jack's ex who had been in charge of the décor.

They had a good study session, and several more followed. After a few weeks Jack began to get the hang of how literature is taught these days. He didn't like it all that much, but he figured he could get by with at least a gentleman's C.

But it was Vanessa, far more than Hemingway or the grim and cynical Professor Jameson, who became the focus of his interest. This girl--he couldn't help thinking of her as a girl, even though in the strictest sense she was a full-grown woman who could vote, drive a car, and do almost all the things (except drink alcohol) that adults do--was such a fetching creature that he couldn't believe she wasn't already spoken for. But then he sensed that her very demureness might have been a barrier to her being snatched up by the oversexed and boisterous males on campus, who generally wanted females more willing to flaunt their "assets" and let every Tom, Dick, and Harry know that they were "available."

After one study session, which extended well beyond six o'clock, Jack placed a hand gently on Vanessa's arm and said, "You've been such a help to me--may I take you out to dinner?"

She blushed again--and again gave Jack that look of apprehension, even fear, that he had come to know so well. Now it was his heart that ached for causing this poor girl unnecessary alarm.

"I'm sorry, Vanessa," he said, "I shouldn't have said that. It's not right--"

"I'll be happy to," she said in an almost inaudible voice. "I don't get taken out very often."

Once more Jack cursed the damnfoolishness of the college boy.

"I can't imagine any woman who deserves to be taken out more than you do," he said fervently. "I know lots of good restaurants that I'd love to introduce you to."

Now she was blushing crimson. It was almost painful to watch. She couldn't meet Jack's gaze.

Her chest was rising and falling rapidly. Licking her lips, she at last managed to say, "That would be wonderful. But--but I'd really like to change. What I'm wearing wouldn't be suitable."

Jack gave her clothes a quick glance. It was a simple outfit of blouse and pleated skirt--typical schoolgirl attire.

"You're fine as you are," he said.

"No, no!" she cried. "I really want to wear something else. Can you take me back to my rooming house before we go to the restaurant?"

"Sure thing, if it means that much to you."

It was a very short drive to her house. Jack said he'd stay in the car while Vanessa changed, to give her maximum privacy. To his surprise, she emerged only a few minutes later--but what a transformation!

She was now wearing a form-fitting black dress that went down to her knees. It had a surprisingly low-cut neck, although she wasn't exactly well endowed in the chest. But this was one girl--no, woman!--who didn't need a robust bosom or bottom to be beautiful. She had also managed to put on just enough makeup to brighten her face without in any sense looking like a tawdry "painted lady."

"You're lovely, Vanessa," Jack said in genuine admiration.

He could have predicted that she would blush and look down at her hands, unable to reply.

The dinner--at a Japanese restaurant that Jack favored--was heavenly. He was impressed at how well she manipulated her chopsticks: he could barely get the food into his mouth, and scooping up rice with chopsticks proved so impossible that he was reduced to the shame of asking the waitress for a fork. Vanessa smiled at his awkwardness, but it was a genial smile that had a lot of sympathy in it.

In the midst of the meal, after some idle banter about nothing in particular, Vanessa was bold enough to ask: "What happened to your wife? I mean, to your marriage?"

Jack sighed wearily. "I wish I could tell you. Maybe, after twenty years of marriage, we just got tired of each other. Especially when our daughter graduated from high school--"

"Daughter?" she interrupted. "You have a daughter?"

"Yes. Her name's Eileen. She's a senior at the college."

The significance of the remark didn't escape either of them. Eileen was a year older than Vanessa.

"Anyway," he resumed, "once Eileen was out of the house, the troubles got worse. We started arguing a lot--over nothing! Was I going through a midlife crisis? Was she? I just don't know. So we just decided to split up."

"So . . . where is she now?"

"Oh, she's around. But I don't have much communication with her."

Vanessa quickly steered the conversation in a different direction, and the tension of the moment passed.

Jack took her right home afterwards.

From now on, their study sessions frequently evolved into dinner dates. Jack did indeed take her to all manner of restaurants--moderately priced to expensive--that he knew about; and although Vanessa protested meekly that he shouldn't have to pay, he always did. It was a strange relationship: in one sense he almost felt like her father; in another sense she became for him a symbol of his own desperate attempt to cling to youth. There were, of course, other ways he thought of her, but he sternly kept those out of the forefront of his mind.

But there was one time--a Friday--when he invited her back to his house after dinner; and to his surprise she accepted.

It was obvious that both of them were nervous when they drifted into the house. Jack at once put on some soft jazz music to create a soothing atmosphere. Then he went to the sideboard at the back of the dining room and said, "I don't suppose, Vanessa, you'd care for a liqueur?"

Once more a slight blush. "Jack, I've never tasted alcohol."

Oh, God! Here he was corrupting the youth! She was still a year away from being legally able to imbibe--but surely a little glass of Amaretto wouldn't hurt?

"Just try this," he said after pouring out a shot for her. "I think you'll like it."

She sipped it--and did like it, giving Jack the heart-rending smile that he did everything he could to elicit.

He sat down next to her on the sofa. She finished the drink, put it daintily on the end table nearest to her, and then--again to his surprise--rested her head against his chest.

The warmth of her body, and the delicate perfume she was wearing, were for Jack far more intoxicating than the liqueur had been. He gently placed an arm around her shoulders. Then, after some moments when he could detect that both their hearts were beating fast, he lifted up her chin and placed his lips on hers.

It was a soft, fluttery kiss--a kiss that two bashful teenagers might have given each other in the first flush of their mutual affection. It lasted a long time, and in the midst of it Vanessa snaked her arms around Jack's neck and pressed her lips more firmly to his.

He could barely feel her small breasts against his chest--but he did feel them. Then Vanessa made another move that surprised him: she clambered onto his lap while continuing to hold her lips against his, taking his head in both of her hands and holding onto it tightly.

He could feel her hot breath as her mouth opened. She no longer seemed like a girl: this was definitely a woman who was kissing him. And that's what led Jack to do what he did next.

He slipped a hand up her skirt and, as her legs parted, found the crotch of her panties. It was sopping wet.

And yet, Vanessa was so intent on the kiss that she didn't realize what was happening. The opening of her legs had been an instinctive reaction of her body, not of her mind. It was only when his fingers pulled aside the panties and fastened on her sex that she suddenly became aware of what he was doing.

At first she felt she should stop this unexpected invasion of her body, and she put a hand on Jack's wrist; but, aside from the fact that she wasn't strong enough to push his hand away, those questing fingers of his were creating such an overwhelming sensation of warm, glowing pleasure that she realized she didn't want him to stop. Instead, she held his head tight against her chest as he worked blindly--or not so blindly, for he clearly knew what he was doing as he stroked her labia inside and out, stuck a few fingers gently into her vagina, and, above all, rubbed her swelling clitoris with a rotating motion of his thumb.

Far sooner than it had ever taken when she was doing this act herself, Vanessa felt the telltale signs of her culmination emerging; and when her orgasm exploded, proceeding from her sex and radiating out all over her body, she cried out sharply while her slender body quaked and shivered. Now she was holding on to Jack's head and shoulders desperately, as if she were a drowning woman clinging to a piece of driftwood. And Jack, knowing well how the female climax can be almost indefinitely extended by gentle fondling, sought to prolong her paroxysm to unheard-of lengths. At that moment he wanted nothing but to give her as much ecstasy as it was humanly possible to give.

At last she had to push that hand away, and she noticed how it was glistening from the veritable river of fluid that had poured out of her. She was now so overwhelmed with embarrassment--this was, after all, the first time she had ever come in someone else's presence, and come because of someone else's actions--that she was unable to look Jack in the face. But he gently pulled his head out of her grasp and looked up at her, even as some final shudders coursed through her frame.

"Did you like that?" he said softly.

With a shy smile she said, "Yes, it was wonderful."

The question now became: was Vanessa prepared to do anything more? She was well aware that few men would be satisfied at giving pleasure without receiving any of their own; but she wasn't at all sure she was prepared to do anything along that line. So she wasn't entirely surprised when Jack began carefully undoing the buttons on her blouse.

She watched him fixedly as he worked, and when he finished he parted the blouse and pulled it off her shoulders. Now another concern overtook her--one that had haunted her for years.

"I'm afraid I don't have much in the breast department," she said lugubriously.

But that didn't deter Jack, who unfastened the clasps of her bra and tossed it aside as he had done her blouse.

What lay revealed to his gaze was an extraordinary sight. He had never seen breasts quite like Vanessa's. It was, strictly speaking, true that they were modest (he later learned that her bra size was 32A); but they weren't really "small." They actually covered a large part of her upper chest; it was simply that they were soft little mounds with the smallest nipples he had ever seen, even though those nipples had become hard and erect from her excitement.

"They're beautiful," he breathed. "You're beautiful."

He made her get off his lap, then gently peeled off her skirt, stockings, and panties until she stood naked in front of him. She instinctively placed hands over her breasts and delta, but after a while gave up the effort to cover her nudity as futile. As she endured his gaze with increasing courage and even a certain pride, he was struck both by the delicacy of her physique and also by its intense femininity. She didn't need flamboyant curves to proclaim what a gorgeous woman she was; her overall bearing was enough to reveal her as a quintessential female, from her oval, faintly melancholy face framed by blond curls to the sloping shoulders and those exquisite breasts to the gentle flaring of her hips to her strong thighs and tapering caves to her small, dainty feet. And when, unable to resist a full inspection of this divine creature, he made her turn around, he took in the firm back and soft curves of her bottom, so small that his hand could have almost entirely covered one of the cheeks.

Making her face him again, he was also struck by the near absence of fur on her groin. His wife had been proud of her luxuriant bush, and he'd relished it too. But the sparse black hairs on Vanessa's mons augmented the impression of her youth and innocence.

"Do you shave, dear?" he said.

"No," she replied, puzzled that he could even ask such a question.

Without another word he picked her up--she was, of course, light as a feather--and headed up the stairs. Among the four bedrooms on the second floor, one was clearly a master bedroom, with its own bathroom and a spacious four-poster king-size bed dominating the area. Her eyes widened at the very sight of the bed, with all the symbolism it carried. After he had placed her on it, he retreated to the middle of the room and slowly undressed.

It was now her turn to watch him raptly as he removed one piece of clothing after another. But when he finally pulled down his boxer briefs and stood naked in front of her, she clapped a hand over her mouth and gaped in awe--and fear.

"It--it's so big," she whispered.

Jack's member, which had been hard for some time, was a full eight inches long.

"I guess it's a little bigger than average," he said modestly. "But I'm sure you'll manage."

He climbed into bed, amused that at first she tried to slide away from him as if he had some contagious disease. But the moment she felt his skin pressing against her own, from head to toe, she relished the sensation and threw her arms around his neck, receiving his kisses and caresses with the full realization that it was her own desirability that was causing Jack to be so stimulated. But when he made her lie on her back, placed his body between her legs, and was about to enter her, she blurted out in a rush of words:

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