Andy looked horrified. "I'm sorry...if it had been me, I never would have told anyone."
"I know you wouldn't," Sylvia said. She stood up again in case he needed a bit of space, and it occurred to her now that her pleated skirt and white blouse made the perfect virginal outfit. Suddenly that seemed totally inappropriate, but Andy didn't appear to mind. "But I told you that to show you, well, maybe you were smart to wait until the time was right! I sure wish I had."
"Thanks, but really, I waited too long. That's why this is all so weird to me now, since I've had all these years to wonder what it's like, wanting to do it but being afraid at the same time because I don't really know anything about a woman's body and feeling like now it's too late to learn."
"You probably know more than you think you do, Andy." Sylvia knew all too well how the more a man thought he knew about women, the less he really did in most cases. "But you know, I could teach you. Think of it as my Christmas present!"
Andy looked delighted, and Sylvia was sure he was rock hard. "But I didn't get you anything," he teased.
"You could give me your virginity, couldn't you?"
They shared a passionate laugh, and Sylvia beckoned for Andy to stand up and take her in his arms again. He did, and soon they were sharing their first kiss. He was a surprisingly good kisser for a novice, playful but not too aggressive with his tongue, and Sylvia saw it as a good sign. When it was over, Andy said, "You'll understand if I'm not much good at it?"
"I said I would teach you, didn't I?"
"Yes, yes of course. I just hope I don't seem too clueless about your body," Andy said. With a wry grin he added, "Or frightened of it. I have to admit that's been a problem before."
"I could tell you some stories about my period and give you a heart attack," Sylvia said pertly.
Andy was silent for a moment, then burst into a hearty laugh. "Thanks, I needed that," he said, and Sylvia sighed with relief as she squeezed him again. Bringing up the ultimate gender taboo had been a big risk, but the shock was just what Andy needed to get over his intimidation, she figured. And evidently it had worked, as now he melted back into her arms and the tension seemed to evaporate. He kissed her again, and this one went on for quite some time. Sylvia rubbed his back in circles with both hands, and he followed her lead and did the same. Already he seemed more comfortable with the intimacy. Maybe that was her imagination, maybe it wasn't, but Andy was not complaining in any event.
Outside, the storm was in full-force now, with the snow pouring down in big wet flakes and visibility near zero. Where Sylvia normally would have drawn the curtains, it seemed only fitting to keep the beautiful sight open to them; there was no risk at all of anyone in the street seeing a thing, if indeed there even was anyone in the street. The idea that there might be only thrilled her more, though it also occurred to her that it would likely make Andy uncomfortable. But Sylvia thought of a compromise. "Let me turn the lights off," she said. "That will give us some mood lighting."
"I'll get them," Andy said, and he made for the switch by the door. That gave Sylvia time to light the three red and green candles she'd collected in the Secret Santa exchange at work, which had been gathering dust on her dresser all week. The glow and the piney scent went perfectly with the view outside. She turned back to see Andy walking gingerly back around the bed. He was laughing nervously.
"Are you feeling okay so far?" she asked him.
"Fine," he said. "Just nervous. Performance anxiety, I guess."
Sylvia couldn't think just what to say to that. So she said nothing. Better to show him he had nothing to be frightened of. Instead she took both his hands in hers and guided him to sit down on the bed. Then she sat alongside him and leaned in for another kiss. Not wanting to push too hard after all he had told her, she kept things fairly vanilla for the time being, rubbing his chest playfully again and again but not reaching below. His mild moans and sighs indicated that he was content with that next step. She awaited some sign from him, perhaps touching her legs or breasts, before pushing him any further. In the meantime, she enjoyed his increasingly bold kisses and his hands on her back and shoulders.
The delightful mild petting went on for what felt like at least ten minutes to Sylvia, though she never looked at the clock. Although Andy seemed to be at ease, he never showed any sign of pushing the envelope. Sylvia concluded that she would just have to nudge him a bit. Only fair, really, when she had offered to teach him. After one final lingering round of tongue-wrestling, she pulled back just a bit. Andy withdrew his hands, and she took them both in hers. "I told you we don't bite!" she teased, and she placed his hands on her breasts, even taking care to set his thumbs over her nipples, which were now hard enough to be felt through her clothes.
"You like that?" he asked.
"I love it," she said. "Can you feel, under your thumbs? That's because you've done such a good job so far!" She placed her hands over his, and directed his caresses. "Oh, that feels wonderful, Andy. Now you do it without me." And she removed her hands. He was a bit clumsy, pressing a bit too hard and not paying as much attention to her nipples as she would have liked, but certainly not bad for a first try. Besides, just knowing that they were Andy's hands ensured her enjoyment no matter how amateurish he was at this stage. As he gained confidence and his strokes became more pleasurable, Sylvia leaned back and propped herself up with both hands behind her on the bed, and threw her head back to savor his touch. "Feels so good," she whispered a couple of times.
She also spread her legs, in hope that he might take the hint and make the next step himself. To help him along, Sylvia placed one hand on his thigh and leaned in for another kiss. She squeezed his thigh gently and rubbed in place, and reached ever so slightly inward with her fingers before rubbing more gently up and down his leg. The hint worked: with her breasts no longer a convenient reach for both hands, he touched her knee and drew his hand slowly but surely upward. The delightful sensation made Sylvia wish she had removed her tights, but even with the fabric in the way it felt delicious. Perhaps she could think of an artful way for him to help her off with them.
On that thought, she opened her eyes and whispered, "Well done. That feels great."
"Want more?" he asked.
"Of course I do, but I think we need to get some things out of the way first, don't we?" Once again she took both of his hands in hers, and placed them around the top button of her blouse.
Andy undid the button, as if unwrapping a delicate antique. Sylvia was ready to tear off both their clothes by then, but she found his ultra-gentle approach endearing and only looked down with a smile as he made his way down between her breasts, over her belly, then tugged the fabric gently out from under the waistband of her skirt to undo the last button. Sylvia had the cuffs long since undone by then, and was more than happy to dispense with the garment. She anticipated him taking a long look at her in her bra before anything else happened. But she was pleasantly surprised. He eyed her adoringly for only a moment before taking the initiative on her breasts with both hands. Sylvia voiced her approval and lay back flat on the bed while he caressed her, his technique already showing definite improvement. It did occur to her a moment too late that he wouldn't be able to undo her bra with her lying on her back; but maybe that would encourage him to explore elsewhere. Those first tentative strokes on her legs had been wonderful, and she was hungry for more.
In the meantime, Sylvia took a chance and set about unbuttoning Andy's shirt. She did it slowly enough for him to ask her to stop if he was getting uncomfortable; but evidently he wasn't, and soon his top had joined hers on the far side of the bed. Sylvia then sat up and took him in a fierce embrace, giving his hands the perfect access to her bra clasp. To her mild surprise, he had no trouble undoing it. "Well done, you!" she teased as she looked down to watch him liberate her breasts. "I doubt too many guys could do that on their own the first time."
"I've imagined it so many times it felt like I'd done it for real before," Andy explained.
"I've imagined you doing it too," Sylvia said. There was no need for Andy to tell her he had not imagined doing it to her; that didn't matter now.
Andy did not need her to guide his hands to her breasts this time. His touch felt twice as delightful on her naked flesh, and Sylvia allowed herself to give in to the passionate expressions she had mostly kept in check up to now. "Oh, Andy..." He leaned in to kiss her on the lips, but Sylvia had other ideas; gently she pushed his head down to her breasts. He seemed to be a faster learner with his mouth than with his hands, and soon his light sucking and licking on her nipples had her whipped into a vocal frenzy. Sylvia was enjoying it all so much that she didn't even realize how loud her responses had become until the sensation stopped and so did she.
Sylvia opened her eyes, and saw Andy sitting up and looking a bit concerned. "Andy?" she asked. "That felt beautiful, why did you stop?"
"I thought it might be too much," he said. "You sounded so worked up there, I was afraid I might hurt you."
"Oh, Andy!" Sylvia was getting frustrated now, but she stopped herself just in time with a reminder that he had never done any of this before. She stood up, and reached out her hands to help him to his feet. "Andy," she said patiently, "When I make those noises, that's a good thing, I promise. I'm sorry, I didn't stop to think what that must sound like to someone who's never heard them before. But I assure you, what you were doing felt wonderful. You're a fast learner with these." On the word "these," she once again placed his hands on her breasts. "But I think we have a lot more to learn." On that note, she ran her hands lightly over his chest. "It's okay if you feel like making noise when I touch you too, you know. It makes me feel good to know I'm making you feel good."
"It does feel good," Andy said. Allowing his enjoyment of her touch to become more vocal now, he also slid his hands downward from her breasts and gingerly slid a few fingers inside her waistband.
Sylvia was delighted. "Why don't you help me off with the skirt?" She reached back and unzipped it. "Don't be shy, there's nothing under there that I don't want you to see!" Andy looked delighted as well as he pushed the fabric gently down over her hips and downward. Sylvia stepped out of the pooled garment and grabbed it up off the floor, explaining how easily it would get wrinkled if left there, and laid it out on the window seat.
Clad only in tights and panties now, Sylvia felt like a perverted ballerina, and she loved it. The look accentuated her wide hips, which sometimes made her feel chubby, but men seemed to like them. Andy was no exception, judging from the adoring glances he was now giving her. "Now," she said, slipping her arms around him once again, "The lesson is going very well, isn't it? Do you feel comfortable so far?"
"Wonderfully so," Andy whispered. "You're...beautiful, Sylvia. I'm so sorry I didn't give us a chance before." He was teasing her breasts again, and his touch was perfectly gentle now.
"Never mind that, Andy. It was worth the wait, and what better time of year for this?" She glanced down at his jeans, and had no doubt of what was pushing its way out just behind them. The next step was up to him, but maybe he needed some more guidance. "Now, do you want to take my tights off, or shall we get these off you first?" On "these" she brushed the front of his jeans and caught a short but wonderful feel of his hard cock.
"Only seems fair for me to strip down to your level, at least," Andy said, and he reached down to undo his belt buckle.
Sylvia was thrilled as she watched him unzip his jeans. Not wanting to push him too fast, she kept her tights on for the time being, though she was itching to be free of them. Andy, for his part, smiled but wouldn't look her in the eye as his jeans dropped to his ankles. Sylvia could see why he was once again acting shy: the poor dear was wearing tightie-whities! She hadn't seen any such thing since high school that she could recall, and she hadn't missed the sight. But any risk of making Andy uncomfortable was offset when she remembered she was wearing plain gray panties that probably wouldn't be all that attractive to him either. She had, after all, not expected this to happen today!
Making a mental note to buy him some boxers at the first available after-Christmas sale, Sylvia stroked his almost-visible cock. One thing about tightie-whities, she admitted, they had plenty of give for a moment like this! Andy's breathing grew faster and more audible as she rubbed, though she kept the motion slow at first. Time for the next lesson. "Remember what I said about how it's okay to make noise, Andy?"
"Good! So if this feels as good as I hope it does, don't be shy. Am I pressing too hard?"
"No...a little harder is okay," Andy said, and Sylvia complied. "Yes! That's great. Ohhhhh!"
"Excellent job, Andy," she said. "Now can we get these out of the way?" She reached her fingers inside the waistband of his briefs, but didn't push down until he nodded. His rock-hard cock sprang to full attention as she slid them down past it. "Oh, Andy, that's so beautiful," she cooed, taking it gently in her hands. "Now let's lay you back..." She gave him a gentle push and he lay on his back before her, his erection pointing at the ceiling. Sylvia wanted more than ever to remove her tights and panties, which she knew were wet to the touch, but first it was time to put him a bit more at ease with this latest boundary they had knocked down. Straddling his legs, she took his cock in one hand and teased his balls gently with the other. "Now, Andy, it's your turn to teach me. How do you like to play with it?"
"Play with it?" Andy asked between husky sighs.
"Silly boy, don't you expect me to believe you don't masturbate!" Sylvia ordered him. "I do, you know."
"That sounds beautiful!" Andy said, but he still didn't answer her question.
"Well, you'll be welcome to watch me do it sometime if you like," she told him. "But first, show me how you do it. That's how I'll know how to please you." She withdrew her hands and waited.
After just a moment's hesitation, Andy wrapped his right hand around it loosely, and began rubbing his palm up and down over the head -- a technique Sylvia had seen before. She enjoyed the view in silence with the flickering of the candles dancing on his wonderful body, which writhed a bit beneath hers as he thrust his hips back and forth slightly. "Think I started doing it this way when I was about thirteen," he told her. "Maybe a bit younger, can't remember for sure. Before that I used to lie face down and hump the floor. Can't remember why I changed."
"Beautiful," Sylvia said just above a whisper, now leaning down to stroke his chest again. "Thank you for sharing that with me. Do you want to finish yourself off now?"
She hoped against hope that he would say no, and to her relief he did. "No, I want to finish what we've both started, Syl." With that he let go of himself and propped himself up on his elbows, admiring her as she had been admiring him.
"Wonderful!" Sylvia could not hide her relief at his response. She climbed off him and stood up. "Are you ready to see all of me?"
Andy answered only with an expectant chuckle.
The moment was nothing like what Sylvia had imagined so many times alone in her bed, where she had seen him gracefully removing one layer after another in the heat of foreplay. There had been many variations, but none of them had involved her simply leaning over to pull her tights and panties off. Of course, they also hadn't involved hers being the first female body he had ever seen, and that gave her a delightful tickle as she kicked off the last of her clothes and stood nude before him. "See? Not so frightening, is it?" she asked, exulting in the first-time rush she was sure he was feeling.
"It's the opposite of frightening," he said, and he stood up with his hands out. The cheesy line notwithstanding, Sylvia was overjoyed at his reaction and could feel the spark of his touch even before his hands landed on her breasts. "I've imagined this so many times," he whispered as he cupped one hand tenderly over her breast and ran the other down her side. If his caresses were still a bit clumsy and tentative, that only endeared her more to him, and she sighed happily as he ran his hands over her, even allowing the occasional giggle when he tickled her here and there.
Sylvia returned the favor and reached down to rub him gently as she had watched him do to himself. "Don't be shy with your reaction," she reminded him, and he wasn't. Her light strokes were met with delicious gasps and sighs, and he reciprocated with strokes on both of her breasts that took her breath away as well. Not wanting to bring him over the edge before they even got in bed, she kept her strokes light and slow, enough to tease him pleasantly, and soon he showed no sign of apprehension, only delight.
But there was one boundary left to cross, and after a few minutes of running their hands about one another, she realized he wasn't going to cross it himself. Emboldened as he seemed to be with her upper body, he always kept his hands above her waist. Sylvia had, of course, met other guys like that -- there seemed to be a lot, though she didn't know why -- and she had expected this would be another hurdle for Andy. It would be a fun one if she played it right, though. Gently, she took his hands in hers and squeezed them lightly. "I think you're definitely ready for the next lesson, Andy, don't you?"
"What's left to do, get in bed?"
Sylvia couldn't help laughing. "Don't play dumb with me! You know what you haven't explored yet."
"Sorry..." Andy looked sheepish, and his erection seemed to die off.
"Don't be sorry. I know it's a lot all at once. But I promise my vagina doesn't bite, Andy."
He laughed, and looked a bit more relaxed at her use of the big word.
Sylvia took his hands again, and placed them just inside her hips, on either side of her pubic hair triangle. "It's for you to share, just like I did with you, Andy," she said. "Go ahead, touch it!"
She was pleased to see him getting hard again as he slowly, reverently reached his right hand into her pubes. He ran his fingers through them carefully, barely touching her skin at first, then rubbing a bit harder with his fingertips only. Sylvia let him play there for a few minutes, enjoying the pleasant mild tickle and anticipating more. He never came within an inch of her clitoris and he never felt how wet she was for him, but his touch was nevertheless delightful as once again she mused that she was the first woman he'd ever touched this way. "Do you like that?" she asked when it appeared he was at a loss for what to do next. "I do. It feels wonderful to have you get to know my body like this."
"For me too," Andy said. "I'm sorry I hesitated."
"You know, you still are hesitating a little bit," she told him. Then, pointing to the headboard, she said, "Sit back on the bed, spread your legs."
Andy did as he was told. "Why?" he asked as he settled himself.
"I told you before, I'd let you watch me masturbate," she told him. "But instead of that, I'll show you how to do it for me."
"Gee, I don't know if I can..."