Crossing the Line - Again

He didn't expect this.

Well, in all fairness, he should have. But he didn't.

He knew she was a very sensual, sexual being – even if she had forgotten that part of herself during the past several years of emotional abuse by a husband who made her feel as if she was sexually incompetent and undesirable. On the contrary, it was clearly evident to him. It showed in how she carried herself...in her sexy bedroom eyes...in the gentle, casual touches she frequently gave him and all her other friends. She probably didn't even recognize those signs of latent sexuality apparent in her behavior and demeanor, but he was a keen observer of human interaction. He always had been. And because of that, he should have anticipated that actually acting on one of their sexual fantasies together would make him feel this.

But he didn't.

This was his first thought as he woke from a brief nap, holding a desirable, fascinating, sleeping woman close in his arms. And his next was this...

What now?

Over the past 7 months, they'd developed a tight friendship that just tilted on its axis an hour ago by sharing this new level of intimacy with her. That friendship was very important to him, perhaps even more than he'd ever admitted to himself until this moment. The moment when he wondered if he'd lost it forever by becoming her lover.

But God help him, he didn't regret what they'd just shared. As he watched his new lover sleeping and saw the smile on her lips, knowing that it was there at least in part because of him, he couldn't bring himself to wish that he could go back in time and never knock on her door. No, that just wouldn't be close to honest, and he was honest to a fault. The truth was no matter what consequence he would face for this choice, if he had the chance again, he'd make the same call. Watching her blossom in front of his eyes, slay her demons with his support and encouragement, and become the woman he suspected she'd always been deep inside was worth whatever price he'd have to pay. It was time to wake Sleeping Beauty and determine how much this would cost him.

He leaned down and gently claimed her lips in a soft, sweet kiss meant to awaken her. He was rewarded by a sleepy, but still turned-on lover reaching down between them to stroke his rapidly rising manhood. It appeared that the cost was going to be deferred. She wasn't done with him yet. Thank God.

What was a man to do when a gorgeous, sexy woman stroked him? Why, stroke back, of course!

He began by stroking with his tongue, using it to open her lips and taste her sweetness once again. Then he allowed his hands to do some stroking of their own. Her breasts were a nearly perfect fit for his hands, and as he was a boob guy, he enjoyed the chance to rub them, to make her nipples hard by running his thumbs around them.

He heard her slight moan and knew that if they didn't stop this soon, it was going to go farther than the incredible oral sex they'd just shared. Before that happened, they needed to talk, to make sure that in the heat of the moment they didn't make decisions guided by passion that should have been far more intentionally reasoned out.

As much as he hated to, he eased up the kiss and put a little more space between them.

"Tired of me already," she teased when his lips left hers. She smiled as he reached for her hand and brought it to his lips for a kiss, effectively stopping her from continuing to arouse him by stroking his cock.

"Never. But before I take more than you're offering, we need to chat for a minute, my friend," he told her, hoping with all his heart that she indeed still was.

"This did sort of take us both by surprise, didn't it?" she asked.

"Well, I did come here with the intention of us having some fun together, but I have to admit, I'm a little blown away. And by 'a little', I mean totally and completely stunned," he replied.

"Hey! Did you think I was gonna be bad at this?" she asked, faking a hurt she didn't feel. She knew what he truly meant, because she was feeling it, too. Being with him overwhelmed her senses and she was still reeling a bit from it, truth be told. But she wouldn't miss the opportunity to make him squirm a bit. It was fun to watch.

"No! Not at all! I mean, why would I have ever come asking for it if I thought you were not going to be any good? That just doesn't make sense," he replied, scrambling for some way to tell her how amazing she was without giving away how he was truly feeling.

And that was really the problem here, he realized with sudden clarity. He was feeling. This wasn't just sex to him.

It didn't matter that he intended for this to be like his many other sexual adventures over the years. It didn't matter that his plan was for this to be a one-time thing. No, those things didn't matter because actually being with her and experiencing what they had already changed those ideas. She wasn't like anyone else he'd ever been with. And he'd give everything he owned for this not to be a one-time thing between them.

But how did he even begin to have that conversation with her? They were laying here naked in bed with each other, both of them wanting to do something other than talk right now. How did he tell her that this was more than wanting her, more than desire, more than he expected?

She saved him from that decision by starting the conversation herself.

"You know, I have fantasized about this, dreamed about this, but now that we've actually done this, I have to tell you...it was so much better than anything I could have imagined. Thank you for being willing to do this with me."

"Hey, babe. I'm no martyr. I didn't do this solely for you. I did this because I wanted it just as much as you did. I think this was just as amazing as you do. One day you need to believe that," he responded.

"Oh, I know you enjoyed it. But I also know that you did this primarily for me. I wasn't ready to be so blown away by this. And if I wasn't, I'm betting you weren't either. So I just want to know, what's next? Because I have to tell you, if you leave it up to me, we keep working on the list. I want to try my entire Top 5 list with you. Is that what you want, too?" she asked.

He could scarcely believe what he'd just heard her say. He had known her for months now and knew that she wasn't a typical woman in many regards. Oh, she was physically all woman, and he now had first-hand knowledge to back up that statement. But her directness, her lack of coy game playing, trying to coax him into her bed, her willingness to tackle this head on and honestly, rather than dodge and weave away from the subject...the bluntness of her question was completely unexpected! He had to admit, not only did he appreciate her honesty, but he also found it a huge turn on. She didn't want to play the kind of games where she teased him and taunted him. She just wanted to be with him, and she had made it known. His respect for her was growing exponentially. As was his desire.

"Absolutely yes," he replied. "In fact, the sooner the better." And with that, he closed the space between them he had put between them minutes ago and drew her up close to him, letting her feel the physical reaction he had to her words.

"Oh, honey! It's time to put that to good use," she whispered close to his ear, and then began kissing and licking her way from his neck to his lips, where he took over the situation, claiming her lips in a deep, hot kiss. His tongue mirrored the thrusting movement his cock would likely do soon. She moaned her approval and kissed him back just as intensely.

"Number 2 next?" he asked as they broke the kiss, his voice husky with desire.

"Well, my number 2 was your number 1. I wanted you to make me cum with your mouth and tongue. And oh, my how you did! How about your number 2?" she replied, her voice just as deep as his.

"My number 2 was your number 1. I wanted you to swallow my cum after you gave me a blow job. And you did it like a pro," he replied, and then kissed her remembering how hot it was to see her lips on his cock, sucking him for all she was worth.

"Time for number 3 then," he said when their lips parted. "The only question is, your list or mine?"

"How about both?" she suggested. "After all, we did pretty good the first time."

"Babe, if you think that was 'pretty good', I'm wondering what it's gonna take to get you think it was amazing?" he teased.

"Well, let's find out," she replied. "Yours first."

"Absolutely. Feasting on your breasts is something I've fantasized about for a long, long time," he answered. And then he set out to make number 3 on the list happen.

For as long as he could remember, he'd appreciated women's breasts. He loved them to be just big enough to fill his hands in terms of size, with nice, red, puffy nipples that just begged to be sucked on. He enjoyed looking at them, petting them, licking them, kissing them, and sucking on them.

He began by laying her on her back and massaging her shoulders and upper arms. He enjoyed hearing her quiet, soft moans of approval, and seeing the smile that graced her beautiful face. Slowly, he worked his way toward her chest, enjoying watching her squirming, even though he hadn't really done much yet.

When his hands finally reached her breasts, he did something that would make this more enjoyable for both of them. He rolled to his back and brought her with him on top of him.

"Sit up, babe. I want to enjoy you fully," he directed her. She complied easily and quickly, not at all worried that she was too heavy for him. The time for that kind of insecurity was long past between them.

When she settled on top of him, his cock was very near her pussy, and served to remind her of her own list of sexual adventures. Her own number 3 could happen very, very easily from this position. She'd keep that in the back of her mind, but right now, it was time to enjoy his hands and mouth on her.

He began by taking both of her boobs in his hands and gently massaging. The pressure he used was hypnotic and caused her eyes to close in pleasure. Slowly, he changed the pressure a bit so that it was not quite so gentle. Not rough, really, but more insistent. Her eyes stay closed, but her mouth opened slightly as she moaned her approval. He smiled. Exactly the response he wanted.

"Lean toward me, honey," he requested after a few minutes of the sensual massage. She did and was rewarded with his tongue circling one nipple while his thumb circled the other.

"Oh!" she exclaimed, grinding her crotch against his rising cock, wishing he was inside her pussy. The assault on her senses between his mouth, his hands, and what she could feel stiffening beneath her was amazing.

"Soon, baby," he promised. "Soon. Hang on for me, OK?"

"God, yes! Anything. Just don't stop what you're doing. Ever!" she replied, her voice husky with desire.

Encouraged by her response to him, and overcome with the desire to make his mark on her, make his lovemaking something she would not soon forget, he began sucking and nibbling on her nipples, more rough than anything she'd ever experienced, he knew.

Her limited experience hadn't prepared her for what this would do to her. She felt wanton, ready for anything. The slight pain she felt at his hard sucking and the use of his teeth on her tender nipples was erotic, pushing her to places in her mind and body that she'd never been before. She instinctively knew that he could take her farther if she let him. So she invited him, let him know that he could do whatever he wanted to do with her in this moment.

"My God, that feels so good. More, babe...I want more. Harder. Please," she whispered in his ear as he changed breasts and continued his exploration of her breasts.

"Oh, honey...there's more. Don't you worry. Just enjoy," he replied.

And she did. Immensely.

He took his mouth from her nipples and she sat back up more fully, each of them grinding against the other. His cock strained to get inside her, a pleasure that he denied himself for the time being. As they were pressed intimately together, he squeezed her breasts close together and with both hands on her nipples, pinched them until she squealed. Not in pain, but in pleasure. Sure, there was a bit of discomfort, but it was nothing in comparison to the ferocious need she felt to be manhandled by him.

Had he anticipated that this would be happening tonight, he'd have brought his nipple clips so that she could begin to train her nipples to appreciate this kind of pleasure/pain. Her horizons were being broadened far more rapidly than he imagined she'd want, however. He'd just have to bring them next time.

Next time. Yes, by this point, he acknowledged, there would be a next time. He still wasn't ready to examine all the feelings swirling around in his head about this, but he was clear enough on that. This was not a one night stand. Not for either of them. The rest they could work out later. Right now, there was far more pleasure to be shared.

Once her nipples were good and red, he let them loose and gently kissed and licked them, soothing them after the rough time he'd just given them.

As she felt his cool breath gently blowing on her sensitive nipples, she made a decision. She wasn't going to wait to be asked for her number 3. She'd waited her entire life, and most often been disappointed. Nope. Not this time. She gathered her courage about her and reached down between them to touch his beautiful dick.

"Time for my number 3, babe," she whispered and leaned down to kiss him greedily while she positioned his cock at her entrance and impaled herself on it in one rapid move.

He was shocked. Stunned, really, and beyond turned on by the wanton woman who took it upon herself to stuff his cock in her cunt. When did this quiet, reserved, beautiful woman decide she was taking charge of her own pleasure and his? He moaned against her lips at the sheer pleasure of being sheathed inside her tight pussy. God, had anything ever felt so good, he wondered.

When the kiss broke, he was still fully seated in her and reached up to caress her breasts and speak to her.

"Well, well. Look who's getting bossy and demanding in bed," he teased her.

"Oh, honey. You ain't seen nothing yet. I'm quite afraid you've unleashed an animal in me," she replied, blushing at her admission.

"Look at me," he directed, and she did as he demanded. He stopped caressing her breasts so he had her full attention for what he had to say.

"There is no reason for you to be embarrassed or ashamed of enjoying what you're doing right now. My God, you are so sexy sitting on top of me. I've imagined this in my head so many times, and never once did I think you'd be the one to have the guts to take my cock and ride it. I figured if I wanted that to happen, it'd have to be me that initiated it. Do you have any idea what this is doing to me, seeing you take charge of your own body, using it to give and receive pleasure? I am more turned on than I think I have ever been. Don't belittle yourself by feeling anything other than proud and empowered," he admonished her.

"I'm not ashamed. But I am surprised. I didn't think I could do this. But what you're doing to me tonight makes me feel stronger and more desirable than I ever have. I want you. I want you to fuck me. But I want to fuck you, too. And that does make me a bit uncomfortable and out of my element. I've never been this desperate, wanton woman before. But I have to tell you, I like it. I like it a lot," she returned, smiling at him.

"Well, honey, by all means. Fuck me."

And she did. Bad knees and all, she began to raise and lower herself in a rhythm that he found and matched, making the penetration even deeper and more satisfying for them both. The look of sheer joy on her face overwhelmed him. This was how she deserved to live life, he decided, knowing that she was woman enough to satisfy a man. Knowing without a doubt that she was desired, sexy, respected. He would do everything in his power to make sure that this happened for her. He didn't know how, had no idea what that would mean, but this was the life she deserved, not the one she had been resigned to up to this point.

When he saw that she was close to her climax, he made a decision that would finish off both of their number 3's in style. Her first, though. He reached between them as she continued to ride him for all she was worth and found her clit. He was treated to her moan as she slowed her rhythm and began to ride out the pleasure building in her as he massaged her clit and brought her to a full orgasm. God, she was gorgeous when she was overtaken by pleasure. Just beautiful, he thought.

When she had completely stopped riding him and sat still atop his still erect cock, he spoke to her.

"Do you trust me?" he asked.

"With my life," she easily and honestly replied.

"Good. Now that you finished your number 3, I'm going to finish mine. Climb off, baby, and lay down, please."

She did as he asked, wondering what he had planned and hoping it would bring him to his climax. It hadn't escaped her notice that he had yet to cum. But hopefully, whatever he was about to do would remedy that situation.

He straddled her, sitting slightly higher than her waist, and at first, she thought perhaps he was going to use her mouth to finish off their fun. But he had other ideas. His number 3 sexual adventure was all about breasts. And so he reached down to her pussy and used some of her own cum to wet her breasts a bit, and then squeezed them together around his cock. A perfect fit, if he did say so himself.

"Here, let me help you," she offered, and held her tits tight against his cock. He planted his hands on the mattress near her head and began to thrust into her boobs, feeling his balls slap against her tits before he pulled back and thrust again.

She moaned in surprise at how good it felt to have his hard penis rubbing against the sensitive skin of her breasts. He moaned at the pleasure of feeling her tits surround his cock and fully sheath him in their wonderfulness.

Sooner than he'd have liked, he felt the familiar tingle of his spunk getting ready to blow. He warned her that it was close, and then suddenly it wasn't close. It was happening. He wondered what she'd do, how she'd handle this. He needn't have worried. His sexy woman had it handled.

She opened her mouth and caught the first few spurts as they reached her. The rest of the considerable load he blew she kept pressed to her chest tightly as she closed her tits upon his erupting cock. When she could feel that he was done, and she had swallowed her delicious feast, she let loose her tight hold on her breasts and let his cock free.

She licked it clean for him as he brought it to her lips, making him happier than he remembered being in a long, long time. And then she pushed him over the edge of the happiness meter.

"Since you love my breasts so much, I think you need to clean them, don't you?" she teased.

"It would be my pleasure," he returned and rubbed his semen into the sweet, soft skin of her breasts as if it were the most luxurious body lotion he'd ever applied. And in her opinion, it most certainly was.

As the warm afterglow enveloped both of them and the urgency of the moment faded into a sweet, comfortable passion, they snuggled together in her bed, him spooning up against the back of her, holding her breasts like the absolute treasure they were.

"Stay with me tonight?" she asked quietly, hoping his answer would please her as much as his lovemaking had.

"Yes."

There was much to discuss, much to figure out in his own mind, and then share with her. But for right here, right now, nothing else felt like the right answer. Yes, he would stay. Yes, he had an amazing time this evening with her and wanted it to continue. Yes, he would do this again – soon.