Devil's Bargain

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.

"I'd like that," Jeremy replied, withdrawing both hands and taking a step back.

"What shall it be first?" Angela asked as she placed one hand on the top laces of her blouse and the other on the side zipper of her skirt, "the top or the bottom?"

"The top, please," he replied, his eyes riveted on the impression of her nipples against the fabric.

"The top it is then," she smiled, having known the answer even before she'd asked the question. From the first time she had let a boy take off her top back in high school, few men had failed to view her breasts as their primary object of interest.

Carefully, slowly, Angela pulled open the laces that held the blouse tight against her bounty, while at the same time, pulling the bottom of her shirt out of her skirt with her other hand. Then, taking hold of the sides of the white blouse, she pulled it up and over her head.

"Oh wow," she heard the teenager say under his breath as he took in her large breasts straining against the confines of her bra.

While dressing for the evening, Angela had specifically picked this particular bra when she laid out her outfit. The material was firm enough to hold everything in place, but sheer enough to allow the impression of her silver dollar sized areola to be visible though her blouse. With the blouse off, well it left little to the imagination. She normally reserved it for job interviews and certain first dates.

Jeremy's eyes never wavered as Angela reached around and undid the rear clasp, causing the garment to first fall loose around her arms, and then drop off completely as she helped it along. If it was possible his eyes opened even wider as, bringing a hand to each breast, Angela massaged them softly, restoring the sensitivity that confinement had dulled. Slowly, she turned her body a bit to the right, and then to the left, giving the young man a good long look.

While she had no doubt that he'd seen a bare breast before - no boy who'd grown up with six sisters could've failed to have gotten at least a few glimpses along the way - Angela was certain that he'd never had the time to really appreciate the view.

One that Jeremy now certainly was appreciating as Angela arched back each leg just high enough to slide off her low heeled shoes. Once out of them, she dropped to just about the young man's height, which suited her fine. There were some things that just worked better if both parties were about the same size.

"So tell me, my young friend, how do the old lady's boobs compare to the ones you normally look at?" Angela asked whimsically.

"They're beautiful," Jeremy said, his eyes now focused on her fully excited nipples. "They're even better than Francesca's."

Before Angela could wonder who Francesca might be, a flush of embarrassment on Jeremy's face gave her the most likely answer. She'd bet a night's tips that was the name of one of his six sisters. There had been a family photo out in the foyer, and from what she had seen, just about all of his sisters had been "gifted by the boob fairy", as she heard her son once remark. Obviously, Francesca, whichever one she had been, had been gifted just a bit more than the rest.

The best way to ease his discomfiture, Angela decided, was to give him something more to look at. That in mind, she undid the zipper on her skirt, letting it drop down to the floor. No sooner had she stepped out of the now loose material around her ankles than she kicked it to the side. Then, leaning forward, she slipped her fingers under each side of her panties' waistband and slowly eased that down her legs as well.

By the time she'd stood back upright, the focus of Jeremy's gaze had dropped considerably. From the expression on his face, the forty year old was pretty certain this wasn't a sight he'd seen before - at least not outside of the pictures in the magazines that boys his age always seemed to manage to get hold of despite their mature rating.

Many women Angela's age, she knew, preferred to let their pubic hair grow wild, much as their mothers and grandmothers had done in the old country. Some younger women, however, preferred to trim it so tightly as to resemble that of a prepubescent girl, or so she had heard. Angela preferred to just trim it enough to keep it neat, especially since, with no ring on her finger anymore, it was more likely to been seen and hopefully appreciated by more than one man. From Jeremy's reaction, a lack of appreciation didn't seem to be a concern.

"Now it's your turn," Angela said after giving Jeremy a bit more time to take in the naked view.

Without moving his eyes, Jeremy brought both hands up to the buttons on his shirt and began to undo the uppermost ones. He'd gotten as far as the third one when Angela suddenly asked him to stop.

"On second thought," she said as she took a few steps to bring them only inches part, "it might be more fun if I do it."

After giving Jeremy a quick kiss, Angela picked up right where he'd left off, slipping the shirt off him as the last button was undone. The buckle and top button of his jeans followed, along with the zipper which, mindful of the valuable asset beneath, she lowered with infinite care.

That accomplished, she slid her hand down his pants and under the waistband of his briefs. She closed her fingers around the cock that she knew she'd find far from soft, smiling as the touch caused Jeremy to let out a loud, pleasing breath.

'My, this feels impressive,' Angela thought as she judged the length and width of his manhood, finding it more than she expected.

She stroked it a few more times, producing an even larger reaction from Jeremy as it grew harder in her hand. Matching smiles filled both their faces.

Withdrawing her hand after a few more playful tugs, Angela turned her attention to his jeans which, after she had pulled them down around his ankles, Jeremy took a step back out of . He took a further moment to rid himself of his sweat socks, dropping them behind him before stepping forward again. Close enough for Angela to place the flat of her hand his shorts, the bulge in which she again began to massage softly.

As she caressed his cock through the thin cotton, Angela reached under his t-shirt with her other hand, stroking his lightly haired chest, rubbing the tips of her fingers against nipples almost as hard as hers. The excitement of her touch was evident in the increase in Jeremy's breaths and heartbeat, causing in turn an increase of her own.

Pleased with herself, Angela gave his cock one last fondle before bringing both hands to the sides of his undershirt to lift it up and over his head. Leaning forward, she gently kissed each of his nipples, taking a moment to caress each with the tip of her tongue. Until now, Jeremy had never realized how sensitive they could be.

"You like that, don't you?" Angela asked as she pulled back just a bit.

Jeremy nodded his head in the affirmative.

"Good," Angela smiled. "I think we're going to find a lot of things that you are going to like."

With that, she brought her hands to the sides of his briefs and in one quick motion, pulled them all the way down to the floor. The sudden action cause his erect cock to spring upward, bouncing a few times before coming to rest at an almost perfect forty-five degree angle.

'That,' Angela thought as she took in his maleness, 'is one beautiful cock. It would've really been a shame if he had turned out to be into boys.'

Lost in her appreciation, Angela didn't realize, at least for a few more moments, that Jeremy was looking for her to say or at least do something. Once she did, she simply smiled and turning to the bed, pulled down the spread and sheet below. The invitation was self explanatory.

-=-=-=-=-

As they both climbed in the bed, it was obvious that, unlike the one Angela had glimpsed in the master bedroom, Jeremy's small twin was not designed for two people to use. Still, neither of them was about to complain. In fact, having both of their naked bodies already pressed against each other would probably more of a help than hindrance.

Jeremy wasted no time on reaching out to explore Angela's mature but still enticing body. As she might have expected, his hands went right to her breasts, discovering for himself their warmth and softness. With youthful enthusiasm, he pressed his palms against the soft flesh, his fingers rubbing against her nipples, discovering their hardness.

With one hand still on her left breast, Jeremy ran the other down the length of Angela's supine form, across her stomach and down into the valley between her legs. His eyes opened wide as his fingers came to rest on her wet mound, the tips slipping past the fold to caress the deep wetness within.

Pausing to take a deep breath, Jeremy used his fingers to gently open a path into her, his thumb sliding upward to where, according to a 8mm film he and a few of his classmates had secretly borrowed, a woman's clitoris was supposed to be. A couple of breaths later, a look of triumph filled his face as Angela let out a soft moan, telling him he had indeed found it.

'Impressive,' Angela thought, recalling that her ex-husband hadn't even bothered to learn where her clit was until well into their relationship, and then only after she had finally complained that he kept missing the mark.

The thrilled teen played with it for a minute or so, observing Angela's reactions to his touch. Reactions that excited him even more. Then, shifting his position, he turned his attention back to her breasts, this time replacing the touch of his hand with that of his mouth.

"Oh yes, that's also nice," Angela purred as she felt Jeremy's lips close around her left nipple, his tongue sliding back and forth against the hard tip.

As he had been with her clit, he was a bit overeager at first, but soon got the hang of what he was doing, especially after Angela whispered a quiet but helpful instruction in his ear. Back and forth his tongue twirled, sending tiny but pleasing ripples across Angela's chest.

Angela turned to give him easier access to her other mound, an invitation he happily took. He did much better the second time around, his effort bringing a broader smile to the older woman's face, reflecting an almost childish delight as Jeremy continued to play with them. She had long ago realized that she would never fully understand the male gender's fascination with big boobs, but she was always more than willing to enjoy the benefits of it.

Shifting again, Jeremy rolled on top of her, pressing his body against hers. Their mouths met once more and tongues fervently intertwined. She could feel his hardness pressed against her core as he rubbed it back and forth. Experience told her what was going to happen if he kept going, and while she didn't mind him enjoying himself, she was sure she could show him a much more enjoyable way to do so.