“How could I have ever done anything so stupid?” Angela Giordano asked herself, the question unanswered in the silence of the empty room.

Not that the forty year old blonde really needed to ask the question. Her answer was as clear as the reflection in the mirror on the bedroom wall. She had allowed sentiment to overcome good judgment and made what was proving to be a disastrous decision.

Last month, two days before he was supposed to deliver a check for their son’s tuition at Kingsbridge Military Academy, Angela’s ex-husband, Sal, advised her that he didn’t have the funds to cover it. A business deal had gone sour and it would take another few weeks for him to recoup.

Angela had gone ballistic, raging at her former spouse, but in the end she knew that was futile. The money wasn’t there and like the old saying went, you can’t get blood from a stone. It was her own fault, she knew, because she agreed to forego alimony in exchange for Sal taking on the full financial responsibility for Paul’s education. She knew she would eventually get the money, but not in time for the Fall semester.

She’d called the registrar’s office and tried to work out a payment plan, only to be told that was against policy. Kingsbridge had a long waiting list, they said, and if she couldn’t pay the amount in full, Paul’s space would go to one of the applicants on that list.

Her parents, with whom the fourteen year old lived because it was closer to the school, offered to give what they could, but even with their contribution Angela was still a thousand dollars short. A sum that, even in 1972, was considerable. With any possible option quickly exhausted, her likelihood of raising the money seemed slim indeed. So much so that, in her desperation, Angela was willing to make a deal with the devil.

Not that Tony “the Hook” Moretti was really the devil, but depending on whom you listened to, he was damn well close to it.

She’d first met Tony back in the summer of ‘70, a few days after she’d started working at Romano’s, one of the neighborhood’s more popular eateries. The ‘alleged mobster’, as he was always referred to in the newspapers, had a weakness for the old world cuisine that the restaurant was famous for, and made it a habit to frequent it at least twice a week. The well dressed seventy-four year old had taken an instant liking to the buxom waitress, insisting that she wait on his table whenever he came in. Since he always left a sizable tip and, aside from a playful pat on the ass now and then, left her alone, Angela thought herself fortunate.

It so happened that Tony had come in the night before Paul’s tuition was due and couldn’t help but notice the look on the waitress’s face that said something wasn’t right. Unable to enjoy his meal, the balding hood asked her to sit down and tell him what was upsetting her so.

“Is that all?” Tony asked with laughter as Angela finished recounting her story and what to, her at least, was the insurmountable amount she needed.

Angela watched in astonishment as Tony looked over his shoulder and gestured to one of the three men who always seemed to accompany him everywhere. The dark suited man stepped over from the spot where he had been surveying the dining room and leaned low to listen to the older man’s instructions. He nodded his head as he listened, then reached into his jacket and produced a roll of bills thick enough to choke the proverbial horse. Sitting across the table, the stunned blonde could see that every bill in the roll was a hundred, the total easily twice what she made in a year.

‘Omigod, is this really happening?’ Angela asked herself as Tony’s associate laid ten bills on the table before putting the roll away and stepping back to his original vantage point.

“Just think of it as a loan,” Tony said with a broad smile as he slid the small pile of bills toward Angela.

“No, I couldn’t...” Angela hesitantly replied.

Before the words left her mouth, Angela’s mind filled with the risks of incurring an obligation to a man like Tony Moretti. She’d been around long enough to know there was good reason why he was called “the Hook”, and the price some people found themselves paying to get off it.

“Of course you can,” he insisted, not making any attempt to withdraw the money from in front of her. “It’s just a little loan,” he repeated, pausing for effect before adding, “for your son’s education.”

Staring at the money for what seemed a very long time, Angela found it hard to resist the temptation to simply pick it up and solve her money problem. Only the thought of what the loan might ultimately cost her stayed her hand.

If nothing else, the predatory smile that Tony gave her should’ve convinced her that this was not a good idea, but even that seemed to pale against the idea that Paul wouldn’t have to leave school.

“I’ll tell you what,” Tony said, seeing her hesitation, “since you are my favorite waitress, why don’t I give you thirty days without penalty to pay me back?”

“What exactly does that mean?” Angela had asked, her resolve weakening the longer she thought about it.

“You pay back the same amount you borrow,” Tony explained. “It’s as simple as that.”

If Angela had taken her eyes off the money on the table and glanced in the direction of Tony’s money man, she would’ve seen a look of astonishment on his face. A loan without any points meant that Moretti wouldn’t make a dime off the transaction - something that was, in his experience, unprecedented.

“And if I can’t pay it back in thirty days?” Angela asked, a small caution still remaining.

“Then we’ll work something out,” Tony smiled. “Don’t you worry.”

Nevertheless, worry she should’ve.

True to form, Sal called her a few days before the note to Tony was due, saying he’d had another financial setback and she would have to wait a bit longer. So it was with trepidation that she’d gone to tell Tony that she didn’t have the money to pay him back.

When she’d served Tony his lunch that afternoon, he didn’t say a word about the loan being due, at least not until he had finished his meal. Then he simply said that she should have a seat and the two of them would talk. When she nervously sat down across from him, she was surprised when he waved away his ever present bodyguards, as if he didn’t want them privy to their discussion.

“That is not good,” Tony said when she finally told him that she didn’t have the thousand dollars to pay him back.

“I can give you about half right now,” Angela said, “then the rest and whatever interest you think appropriate in a week or two.”

“It’s not that simple,” Tony replied, a hint of disappointment in his voice. “The deal was that you would pay back the amount in full. I can’t go back and change it now; people might get the idea that I was getting soft.”

“I know, but I don’t have it all,” the waitress said, regretting not for the first time today that she’d taken the bargain.

Tony didn’t say a word, picking up instead the small cup in front of him and taking a sip of his espresso.

“Wait a moment,” Angela said, recalling something Tony had also said when they’d made their deal. “You said that if I didn’t have the money, we’d work something out.”

“Yes, I did say that,” the older man acknowledged as he replaced his cup on the saucer. “But that usually involves someone repaying their obligation with a service in lieu of cash. Something that carries a value equal to what they owe. Are you sure that you want to do that?”

Angela thought about it a moment, considering what other options she might have. With few forthcoming, she figured she had little choice.

“What kind of service are we talking about?” Angela asked, a bit fearful of the answer.

“A personal service,” came the reply.

“Could you elaborate on that?” Angela asked, not liking the inflection in the older man’s tone or the look of satisfaction on his face.

He hesitated for a long moment, taking the time to look to his left and right to be sure no one else was in earshot. Then he leaned in close to Angela and, in a low voice, explained the exact nature of the service he required. As she listened, Angela turned pale.

“Don’t you have women who already work for you that would be better for this sort of thing?” she asked once her composure returned, recalling another business his name had been linked to.

“Do you think I would trust one of those whores with something like this?” Tony abruptly replied, his voice rising in volume for the first time she could ever recall.

Stunned into silence, Angela listened carefully as Tony explained exactly what he wanted, a look of surprise filling her face as he expanded on the reasons why. Following his instructions, she wrote her address down on a slip of paper and passed it across the table. As she rose to leave, the aged gangster told her to make sure she was available this evening.

“A car will come around about eight to pick you up,” he said, raising a hand to both dismiss her and at the same time call back his associates.

As she rose and walked away, Angela could feel the eyes of her coworkers on her and wondered how they would react if they knew what she was going to have to do to satisfy her debt.

A late model car with tinted windows pulled up in front of Angela’s apartment house at five minutes to eight. Spotting it from her front window, she had no doubt that was the ride Tony had alluded to. Taking a deep breath, she grabbed her bag and started downstairs hoping to make it outside before any of the neighbors took notice.

The two men, both the driver and the one who had opened the back seat door, said not a word during the ten minute ride to the east side. There, after parking in front of a waterside luxury apartment building, the second man again opened the door for her and said his first and only words.

“He’s waiting for you in apartment 28D.”

Stepping into the lobby, Angela was barely given a second glance by the smartly dressed doorman. Evidently, the manner of her arrival was enough to dispel any questions about her business in the exclusive building.

Nor was a word said by the elevator operator, almost an anachronism in this day and age, as he took her up to the twenty-eighth floor. It took less than a minute to find 28D, this high up there were only four apartments on each floor. She rang the bell, waiting apprehensively for someone to answer the musical chimes.

The steely haired gentleman, also in an expensive three piece suit, that answered the door could’ve been interchangeable with the three who normally accompanied Tony to Romano’s. It was obvious from the onset that he was more than just a butler.

“If you’ll kindly wait in the parlor,” he said, motioning to the room off to the right.

As Angela took a few steps in that direction, she noticed him reach for and put on a hat that had been sitting on a nearby chair. Then he stepped out into the hall, closing the door behind him. Evidently, he’d been instructed not to wait around for the festivities.

Alone for the moment, Angela paused at the large mirror on the hallway wall and checked her appearance. She’d gotten her hair cut a few days before by a beautician who was also a neighbor and willing to wait until payday, so no worry there. Clothing wise, she’d chosen a moderate length, black skirt coupled with a low cut, white peasant blouse - one that best displayed her most prized assets. Finally satisfied that all was as it should be, she turned away from the reflection.

Stepping into the sitting room, Angela felt her breath taken away. Not only was it larger than her entire apartment, but it was decorated with antique furniture that seemed more appropriate for a museum than someone’s home.

A large bay window filled the far wall, beyond which she could see the lights of dozens of small boats scattered across the lake beyond. It truly was an awesome sight - almost enough to make her forget why she was here.

The sound of movement behind her reminded her as in response she turned in the direction from which it came. Face to face with the new arrival, a look of surprise filled her face. To say he wasn’t what she’d expected was an understatement to say the least.

“Hello, you must be Jeremy,” she finally said, extending her hand in greeting.

The young man, who looked much younger than the seventeen years she knew him to be, made no attempt to reach out in return. Wearing a tan short sleeved button down shirt and jeans over a slender build, the teenager had short sandy hair and soft effeminate features.

“Yeah, I’m Jeremy,” he finally said.

“Well, it’s nice to meet you. I’m Angela,” the older woman said as she withdrew her hand but closed the distance between them with a few steps.

“I know who you are,” Jeremy said, a trace of irritability in his tone.

‘This is not going to be as simple as I thought,’ Angela mused as she took note of it.

Her thoughts flashed back to what she had been told a few hours before during that private conversation at Romano’s. How late in life, well past his prime, Tony had finally been blessed with a son to carry on his family name. That he had received this blessing from a much younger woman who was not his wife didn’t seem to matter.

Sadly, the baby’s mother didn’t survive the birth, but the infant was immediately taken in by Alyssa Moretti, who had already given her husband six daughters, the youngest of whom was only now reaching maturity. In fact, the apartment they were in now belonged to her, a place in town for when she visited the city and didn’t want to travel back out to their country estate.

“I can handle that the kid wants no part of the business,” Tony had said in a hushed whisper, “but the idea that he might not be all man, well, that’s something else.”

“What do you mean?” Angela had asked.

“He’s seventeen and has no interest in women,” the older man said in frustration.

“Well some boys are late bloomers,” Angela had suggested, not initially catching what the old man was insinuating.

“Not in my family they aren’t,” he said, his voice rising in volume for a few seconds before dropping again. “I was fifteen when I had my first woman.”

In a quick retelling, Tony told her of how he’d lost his virginity to a woman more than twice his age while working at a restaurant not unlike Romano’s. In fact, in many ways, Angela reminded him of the woman in question, which was why he probably had developed a fondness for her.

“You do this for me,” he said, “you make my boy a man, and we’ll call it even.”

It was, Angela thought, referencing a now famous line from one of the year’s most popular movies, an offer she couldn’t refuse.

It wasn’t that the forty year old divorcee had been celibate since she and her husband had called it quits. Quite the contrary, she saw no reason to give up sex simply because she was no longer married. But the men who occasionally shared her bed had all been more or less her own age. Not even on the coldest, loneliest nights had her fantasies ever involved someone little more than a boy.

A boy who definitely didn’t match the mental image she had formed of him beforehand. She had considered the idea that Jeremy might have no interest in girls because they had no interest in him - something a loving father might easily overlook. Teenage girls could be cruel in that regard, especially if a boy was considered unattractive or even just overweight. That had obviously proven not the case, as just one look at the high school senior said that he should’ve had those girls eagerly lining up.

That left the insinuation that his father had made, his concern that his progeny might not be all man. Angela could certainly understand how the youth’s appearance and mannerisms might suggest that, but she’d also learned long ago that appearances didn’t always reflect sexuality. She’d known more than one ‘manly’ man who’d actually turned out to be quite light in the loafers.

Another concern then crossed her mind. If Tony’s worries about his son were justified, what did he think she was going to be able to do about it - fuck him straight?

Finally remembering his manners, Jeremy offered Angela a seat on the nearby couch and, once she had taken it, took one himself on a adjacent chair. Before he did so, however, he asked if he could get her anything, only to be told that she was fine.

“Did your father explain what I’m doing here?” Angela asked, wondering how she could ever explain it if he hadn’t.

“He explained all right,” Jeremy said, the petulance in his voice now replaced by resignation. “The old man is worried that I might be a bit of a fruit and he wants you to find out for sure.”

“Are you?” Angela asked, deciding to go straight to the heart of the matter.

“Excuse me?” Jeremy asked in turn.

“Are you a bit of a fruit?” Angela repeating, using the outdated reference.

Jeremy was taken back by the question, then, instead of answering - he laughed.

“You find the question funny?” Angela asked.

“No, not really,” he said, his tone still reflecting his amusement. “I just find it funny your asking it in the first place - no one’s ever done that.”

“Well, since I did ask, is there an answer?” she added.

“Only if I don’t know is an answer,” he replied.

“Care to explain that?” Angela said.

“I do look at girls,” Jeremy said, “but there are times that I also find myself looking at guys too.”

“Have you ever done anything more than look?” Angela inquired.

“You mean like jerk off with another guy?” Jeremy asked, the tone of his reply suggesting that had indeed occurred.

“Actually, I was thinking of something a bit more substantial,” Angela expanded, “more a manner of doing something to someone else rather than simply with. Did you jerk off the other boy?”

“No, I’ve never done anything like that,” Jeremy replied, confirming her supposition.

“Have you every wanted to?” Angela asked.

“I’m not sure,” Jeremy answered.

“What were you thinking about when you were jerking off with your friend?” she asked.

“Jenny Marzetti,” Jeremy said almost automatically.

“Well, that should tell you something,” Angela smiled.

“Even if I was doing it with a guy at the time?” he asked.

“I would think who you were thinking about while you were doing it would be a lot more of an indication of your interests than who you were doing it with,” Angela suggested. “Also, I don’t think two young men comparing masturbation techniques, which is pretty much what I think you were doing, makes them homosexual. It takes a bit more than that.”

What Angela didn’t say was that she’d had a similar discussion with her own son just a few months ago. Evidently he and his roommate had done their own comparison one night and it had left him feeling a bit ambiguous afterwards.

“Maybe so,” Jeremy agreed, “but what does it make you when you find yourself checking out other guys’ equipment in the showers at school?”

“Curious?” Angela said with a smile, flashing back to her own high school years. “Jeremy, you might not believe it, but back when I was your age, I sometimes found myself looking at my classmates in the showers too.”

“Really?”

“Yes, really,” Angela replied. “All kids have a certain curiosity about their bodies as they grow up and it’s not uncommon for them to compare themselves to others.”

“Why would you have to compare yourself to anyone else?” he asked, staring right at her large mounds.

“Honey, I wasn’t born with these puppies,” she laughed, emphasizing the point by putting her hands beneath each and lifting them slightly. “Believe it or not, I was one of the last girls in my class to hit puberty.”

As Jeremy digested that particular bit of information, Angela dwelled on the fact that much of this kid’s confusion could’ve been avoided if someone had simply sat down and just had a frank discussion with him, much as she was doing now. All he really needed was some honest answers in place of the misguided ones he had formulated on his own.

Over the next forty odd minutes, Angela endeavored to answer any question that Jeremy could think to ask. She did so with the same honesty that she used with her own son. When she had come of age back in the late forties, she would’ve given most anything to have someone do so for her. Instead, all she had to go on was the often wrong, sometimes disastrously so, advice circulated among her classmates - a half score of whom found themselves mothers before their twentieth birthday. That Angela hadn’t been one of them had just been luck.

“Anything else you’d like to ask?” Angela said after Jeremy fell silent for a minute, digesting her answers to his last few questions.

“I can’t think of anything else,” he finally replied after thinking about it for another long minute.

As he digested what he had just learned, Jeremy couldn’t believe how wrong the men he’d grown up around were about sex and women. He’d never directly asked any of them the questions Angela had just answered, of course, but he was an keen listener. Most of the time, his father’s men barely noticed he was around when they talked about their wives and girlfriends, of whom most seemed to have both, and they spoke quite openly of their sex lives - at least, what involved the girlfriends.

“So what are you going to tell my father?” Jeremy asked.

So involved had she been in educating the young man, Angela had momentarily forgot the reason she was here. She was absolutely certain that Jeremy wasn’t what his father feared most, but would he accept that simply on the basis of her discussions with the young man? And he was indeed now a young man in her eyes, and not the boy she initially took him to be.

“I’m not sure what I’m going to tell him,” she admitted.

“You could just tell him that we did it,” Jeremy suggested.

That thought had occurred to Angela and the idea of lying to Tony Moretti was frightening - even more so the consequences of him finding out she had lied. A man like Tony lived in a very black and white world, one in which, when he gave an order, he didn’t expect it to be subject to interpretation.

“I’m not sure that’s a good idea,” Angela replied.

“You’re probably right,” Jeremy agreed after thinking about it.

Angela was in a quandary. An hour ago, before she had walked into the apartment and actually met Jeremy, she’d thought that she’d give the kid an emotionless, fast fuck and be quickly on her way. Now that she had gotten to know him a bit, she couldn’t bring herself to do it, if it wasn’t something he also wanted.

“I’ll just have to find a way to explain to your father why we didn’t,” she said, hardly convincing herself of the possibility, much less the teenager.

“I don’t think he’s going to be very understanding, “ Jeremy pointed out.

“No, I suppose not,” Angela agreed.

“So ... maybe we should give it a try,” Jeremy suggested, this time with much less hesitation in his tone.

Angela was about to repeat her desire not to lead Jeremy into something he didn’t want, but then realized that might no longer be the case. Things had indeed changed in the time she’d been in the apartment. Whatever reluctance he might have previously had, it was clear much of it had been based on his flawed preconceptions about what happened between men and women. Now that he had a different viewpoint, he genuinely wanted to give it a try.

“Are you now saying that you want me to...” she started to say, only to be cut off in mid-sentence.

“Yes, I think I’d like that very much,” Jeremy interjected, his voice now conveying recognizable eagerness.

“You wouldn’t feel more comfortable your first time with someone your own age?” Angela asked, wanting to be totally certain.

“No,” Jeremy quickly replied, “I mean, I want to have sex with girls my own age, but ... I think doing it the first time with someone who really knows what they are doing would be a lot more fun.”

‘That certainly makes sense,’ Angela thought, remembering the blind leading the blind approach of her own first time.

She also now let herself admit the fact that the thought of having sex with a young man barely older than her son had, after getting to know him a little, indeed caused a wetness that had been long absent between her legs.

“You’re absolutely certain?” she asked one last time, almost fearing the possibility that she might change his mind.

When that didn’t happen, it was hard to be certain which of them was more excited at the prospect of what was to come.

“Is there a bedroom we can use?” Angela asked with the broadest of smiles.

Taking Angela by the hand, Jeremy led her through the apartment and down a long hall where there were doors leading to adjacent bedrooms - one on the right and two on the left. All three doors were open. The teenager paused for a moment at the single room and, looking over his shoulder, Angela saw that it was almost as large as the living room and decorated in the same style. Obviously it was the master bedroom and belonged to Jeremy’s adoptive mother.

She wasn’t sure how she felt about doing it in his mother’s bed, an act that might open up all kinds of things best left unexplored. Thankfully that wasn’t his intent, as he then continued onward, coming to a stop and taking a step inward to the second, much smaller room. It only took the briefest of glances to know that this was his room, the décor being unlike the rest of the apartment and reflecting the tastes of a young man.

As she followed him inside, Angela realized that there really shouldn’t have been any doubt as to which room he would take her into. After all, even though it was only half the size of the master bedroom with only a small twin sized bed, this his was his personal space. A place where he could lay night after night and remember the loss of his virginity.

“You have a beautiful room,” Angela said with a smile, trying to put Jeremy at ease.

“Is it okay if I kiss you?” Jeremy unexpectedly asked, his mind obviously already on more than idle banter.

“Of course you can,” Angela smiled, pleased with his desire to get started. She took a few steps closer to where he was standing by the bed. “But I want that to be that last time you ask me if you can do anything. I want you to feel free to touch me anywhere, or in any way that brings you pleasure. This is your moment, and I want it to be as special as I can make it.”

Following her lead, Jeremy also took a step forward, bringing the two of them close enough to embrace, and as their lips came together, he kissed her. A kiss that was more than what you would share with a friend but still less than one you would with a lover. A second kiss followed, then a third, each tipping the scale more toward the latter until Angela felt the tip of the young man’s tongue press against her lips and eagerly opened her mouth to receive it.

‘This boy’s had some practice,’ Angela thought as she brushed the underside of his extended tongue with the tip of her own. She of course had no idea with whom, but it was obvious that this wasn’t his first time on first base.

That thought was interrupted by a familiar pressure against her left breast and Angela didn’t have to look down to know that Jeremy was already making a move towards second base. The touch lasted but a moment, then it was unexpectedly withdrawn.

‘Obviously, whoever has been teaching him to kiss drew the line at touching,’ Angela thought, taking the withdrawal as a reflex action. Without hesitation, she reassuringly took hold of his hand and placed it back on her breast. A warm smile reaffirmed what she had said just a few minutes before - that no part of her was off limits.

Encouraged and finally getting the message, Jeremy unbuttoned the middle buttons of Angela’s blouse, creating a gap large enough for him to slip his hand through. A loud gasp slipped from his lips as the tip of his fingers pressed against her bare flesh. While his hand slid down the deep crevice between her breasts, the blonde leaned closer and gave him the longest, deepest kiss yet.

Jeremy surprised Angela as, in response, he brought his free hand down her back, slipping it under her skirt and against the cheeks of her ass, squeezing that soft flesh. He had indeed gotten the message loud and clear and was eager to explore all there was to explore.

“Mmmmm, that feels nice,” Angela said in a soft, encouraging moan as his hand moved across her cheeks.

Normally, Angela liked to be a more active participant, but right now she thought it best to let Jeremy proceed at his own pace. Besides, she added, he was doing quite well in that regard, she added as she felt him move his hand around to the front of her body, caressing the dampened mound between her legs through the equally wet panties that covered it. His body tight against hers, Angela could feel the racing of his heart and the quickness of his breaths.

“Why don’t I take these things off so they won’t be in your way?” Angela suggested, referring to the clothing that was limiting his explorations.