The One Real Regret

by Janet Nissenson

  She obeyed willingly, allowing him to turn her slightly so that her back was to him. When he wrapped his arms around her waist, hugging her back against his chest, her eyes fluttered shut, her head falling limply back onto his shoulder. Not knowing what to do with her own hands she let them drift up to rest on top of his.

  Max’s deep voice was soft and soothing as his lips hovered near her ear. “You look lovely in this dress, Jill. I was worried, you know, that I was much too old for you, that you were far too innocent and unspoiled for someone like me. And while I still think that way, I was a little relieved when I saw you in this dress for the first time. It makes you look sophisticated, a little older. And very much like a woman.”

  “Ahh.”

  She exhaled softly as his lips teased the nape of her neck while at the same time his hand slid up her ribcage to gently cup her breast. His thumb brushed lightly over the already distended peak of her nipple, causing her to squirm in reaction.

  “Easy,” he murmured soothingly. “I can already sense how responsive you are, Jill, how much passion there is inside of you. You’re nowhere near as shy and reserved as you seem, are you, love?”

  That little endearment thrilled her, made her feel cherished and adored, just as the continued rasp of his thumb over her nipple was causing a warmth deep in her belly, a stirring in her pelvic area that was unfamiliar to her. She gasped audibly as his hand moved downwards over her stomach, and then lower still to that same region of her body where all of those new but extremely pleasant sensations were starting to swirl up.

  “Let me take this off of you, hmm?” asked Max as his fingers hovered over the clasp of her necklace. “I wouldn’t want it to get damaged or have it scratch you.”

  At her brief nod, he deftly unfastened the delicate gold chain and set it aside along with the bracelet she handed to him.

  “These two pieces look like they might be antique,” he mused. “Your grandmother’s, perhaps?”

  “Yes. She didn’t have a lot of jewelry, and most of it was too old-fashioned for my taste, but these I kept. They’re - well, sort of timeless, I thought,” she replied.

  “You’re exactly right. Classic, timeless, lovely. Just like you, Jill. And just like this dress you’re wearing. But as beautiful as you look in it, I think it’s time to remove it. May I?”

  Because she didn’t trust her voice not to crack or quaver, Jill merely nodded, keeping her eyes tightly shut as he began to slowly lower the zipper of the dress. Even though his hands were warm, she couldn’t stop herself from shivering as he carefully peeled the dress off her shoulders and began to slide it down off her hips. Her cheeks were burning with embarrassment, and she was relieved that her back was to him so that she couldn’t observe his reaction at seeing her in just her lingerie.

  Casey and Shoshana had insisted that she buy the horrendously expensive black lace bra and matching panties, along with a pair of sheer black thigh high stockings. And while she had initially felt a naughty little thrill at seeing how sexy she looked in the provocative lingerie, now she desperately hoped Max didn’t think she resembled a tart instead.

  But her fear was fortunately short-lived as he pressed a kiss to the back of her shoulder, his hands on either side of her hips as he whispered huskily, “Jesus, you’re so damned sexy, Jill. And your body is even more beautiful than I imagined it would be. Let me look at you now, sweet.”

  After helping her to step out of the dress and shoes, Max moved to stand in front of her, compelling Jill to keep her eyes even more tightly shut. She couldn’t stop the involuntary trembling that shook her from head to toe as she felt his eyes on her, no doubt inspecting her thoroughly from top to bottom.

  But her eyes flew open on a gasp when he trailed his index finger along the top of her low-cut bra, and then nearly recoiled in uncertainty when she met his burning gaze. She wasn’t precisely sure what lust looked like, but was fairly certain she was seeing it reflected now in Max’s dark eyes.

  “Perfection,” he whispered, his voice catching a little. “Utter perfection. You look - Christ. Like the perfect combination of angel and devil. Keeping myself under control tonight is going to be damned near impossible. It might even kill me. But it will be worth it.”

  Despite her shyness, Jill couldn’t look away or close her eyes as Max took a few steps back and began to undress. His movements were brisk and precise, as though he didn’t intend to waste a single second in the process. His beautifully cut suit jacket - this one of black pinstriped wool - was followed in quick succession by his burgundy silk tie, white shirt, shoes and socks, and finally his trousers, leaving him clad in just a pair of black cotton briefs.

  She’d never been this close to a nearly naked man before, just at the beach or the pool, and had only ever seen a fully nude male body in pictures or illustrations. But even with her rather hopeless lack of experience, Jill didn’t need to be told that Max’s male form was a work of art.

  He was lean and muscular at the same time, his bare skin darker than she would have guessed. His shoulders and arms were sculpted and defined, the sort of muscles one could only get from intensely focused workouts. His broad chest was smooth save for a dark ribbon of hair that bisected his torso and disappeared beneath the waistband of his briefs. His hips were lean but his legs were as superbly muscled as his upper body, solidifying her guess that he spent a lot of time in the gym.

  Her jaw gaped open in stunned admiration of his male beauty, and she couldn’t suppress a gulp of trepidation when her eyes dropped to the crotch of his briefs. He was fully aroused, his penis rising up to press insistently against the cotton fabric, as though impatient to be freed from its confines. And there was no possible way, she thought wildly, that he would ever successfully be able to fit all of - of that inside of the most intimate part of her body.

  The panic she was beginning to feel must have been evident on her face, because Max was quick to reassure her and calm her down.

  “Shh,” he soothed, cupping her cheeks between his palms and dropping a kiss on the bridge of her nose. “Easy, sweet. You look as though you’re about to face a firing squad or worse. I already told you that we’ll take this as slow and easy as necessary. So don’t look so frightened, love. The last thing I would ever do is hurt you. All right?”

  She nodded. “All right,” she whispered.

  “I think this would be easier if we were to lay on the bed,” suggested Max. “Especially since you look as though you’re about to faint.”

  He pulled back the duvet and patted the mattress. Dutifully she eased herself onto the bed, and forced herself not to freeze up when Max joined her there a moment later. But he merely took her in his arms, holding her close, and being careful not to allow his erection to make contact with her body. He caressed her with slow, gentle motions - running his palms up and down her arms and then the sides of her ribcage; squeezing the firm cheeks of her buttocks; trailing his fingertips along the flank of her thigh.

  Max kissed her then, his tongue making slow, lazy circles around the inside of her mouth, and she was so caught up in the pleasure that she barely noticed when he smoothly unhooked her bra and drew it away. He cupped one breast in his hand for a moment before lowering his mouth to her nipple.

  “Ohhh!” she cried as he sucked the pink tip between his lips before circling it with his tongue, feeling that tugging sensation all the way through her midsection and down to where she was wet and aching with some unnamed need.

  “Beautiful. Simply beautiful,” rasped Max as he switched his attention to her other breast. “Perfect, just like I knew you would be.”

  “They’re - they aren’t very big,” she managed to croak, her lower back arching off the mattress as his tongue flicked over the sensitive peak.

  He shook his head, his lips tracing a series of kisses between her breasts. “Bigger isn’t always better, sweet. And your breasts are more than enough, Jill - perfectly shaped and firm and very, very tempting.
” He squeezed both breasts between his palms. “And your skin is incredibly soft, so soft I want to see for myself if every inch of your body feels this way.”

  He proceeded to make good on his word, his hands, lips, and tongue touching nearly every part of her body until she was squirming in reaction, and her flesh feeling as though it was ready to catch fire. A light film of sweat broke out on her forehead and upper lip as Max’s caresses grew bolder, more insistent. She forced herself not to resist when he carefully slipped her lacy panties and then the sheer stockings off. And when he finally touched her there - slipping a finger up inside her tight vaginal passage - she cried out in reaction, her toes curling into the mattress as her hips, buttocks, and lower back lifted up off the bed this time.

  “It’s all right,” crooned Max as he eased his finger out. “Nice and slow, remember? Let’s try this instead to begin with.”

  He cupped her vulva in his palm, then rubbed the pad of his thumb against the hard, ultra-sensitive nub of her clitoris. The resulting sensations spiked through her nerve endings like an electric shock, and Jill found herself clutching handfuls of the bedsheets to stop herself from trembling all over.

  “Shh,” urged Max, prying the fabric out of her grip. “Just relax, sweet. You’re very responsive, you know, very easy to arouse. And very wet.”

  She forced herself to relax this time when he eased first one and then a second finger inside of her vagina, but closed her eyes in embarrassment when she realized just how wet she really was. Max, however, was having none of her shyness, and kissed both of her eyelids.

  “Look at me, love,” he coaxed. “Don’t hide from me, Jill. I want to see the look on this beautiful face when I touch you this way.”

  He thrust his fingers a little deeper inside, pumping in and out of her a little faster now, and eliciting another low moan from her throat. But she kept her eyes open as he’d instructed, her gaze locked with his.

  “That’s it,” he whispered encouragingly. “Keep looking at me, sweet. Tell me. Is this causing you any pain?”

  Jill shook her head. “N-no. It - it feels good. More than good. It’s - ahhh!”

  Without any sort of warning, all of the extremely pleasurable sensations Max had been stirring up - the kisses and caresses and whispered endearments - culminated in a powerful climax. Her legs quivered almost uncontrollably, and her head began to spin so fast she thought she might faint. It felt like her entire body was being consumed by a burning hot fever, and she thrashed to and fro in an effort to escape the heat.

  Max placed a hand on her belly, pressing her lower back against the mattress as he once again calmed her. “It’s all right, love,” he whispered soothingly. “Everything is just fine, Jill. My beautiful, sweet, Jill.”

  He brushed damp strands of hair off her forehead, his lips caressing her flushed cheek as her shudders gradually subsided. He held her close within the circle of his arms comfortingly, his hand continuing to rub her back.

  “Did I just - was that really..” her voice trailed off faintly, too dazed to complete her scattered thoughts.

  Max chuckled softly. “Yes, to both questions. That was your first official orgasm, love. Very unusual, I would imagine, for a virgin. Which only serves to prove what I told you a little while ago. You’re a very passionate woman, Jill. Despite the fact that your grandmother raised you like a nun, I suspect there’s always been this very sensual part of you just waiting to be set free. And,” he added with a kiss, “I’m very, very happy to have played some part in helping that happen.”

  “Thank you,” she whispered, kissing him on the cheek. “I can’t quite believe that just happened, though.”

  “But it did,” he assured her. “I saw it with my own eyes. The look on your face when you came was the most beautiful sight I’ve ever seen. And to know I was the one responsible for putting that look there - well, it made me want you twice as much as I already did. Speaking of which.”

  Max peeled off his one remaining article of clothing, freeing his cock from the snug confines of the black cotton briefs. Jill’s mouth fell open in a silent “O” of combined alarm and admiration at the sight of his long, thick penis, trying not to panic as the renewed fears of how her tight, virginal body could possibly accommodate that imposing male organ threatened to overwhelm her.

  He reached over and snagged one of the condom packets, tearing it open and then rolling the latex over his fully erect cock with ease. Jill concentrated on relaxing her muscles, focusing on her breathing, and trying very, very hard not to tense up in anticipation of what was to happen next.

  Max’s clever fingers slipped back inside of her vaginal passage again, this time spreading the lips wide. “You’re very wet, love, but this is still going to hurt like the devil, I’m afraid,” he murmured regretfully. “I’ll go as slow as possible, take this a little at a time. But I want you to stop me anytime it gets to be too much, all right?”

  Jill nodded, though she knew she would never ask him to stop, that she would bite her tongue or grit her teeth or do whatever was necessary to get through this. After all, he’d been so wonderful to her this evening, so kind and caring and attentive, that there was no possible way she would deny him the same sort of unselfish pleasure he had just given to her.

  But she couldn’t suppress a little gasp of alarm when he gently spread her thighs apart and positioned the tip of his thick, throbbing penis at the entrance to her body. Max squeezed her hip encouragingly.

  “Easy now, love,” he cautioned, and then began to guide his cock inside of her an inch at a time, being mindful to watch her face carefully to gauge her reaction.

  But for all of her fear of pain and burning and blood and other horrors, Jill was surprised and relieved that it really didn’t hurt much at all. There was a definite stretching of her inner tissues, and a sensation of fullness that felt unfamiliar and perhaps a little uncomfortable, too. She took a deep breath, then exhaled as Max thrust a little deeper.

  “All right there, sweet?” he asked, his voice hoarse, betraying the strain he was obviously feeling at having to hold back. Sweat had popped out on his forehead, and the veins on either side of his neck were enlarged. He was holding himself slightly off her body, using the strength of his upper arms to support his torso, and the muscles of his biceps and triceps were clearly defined from the effort.

  “Yes,” she replied breathlessly. “It - there’s no pain. Just feels tight.”

  “Good.” He looked immensely relieved. “I’m going to go a little deeper now, okay?”

  Jill nodded, placing a palm against his heaving chest in confirmation. Max made a sound that was half-groan, half-grunt as he flexed his buttocks and then pushed inside of her once, twice, and then a third time until he was all the way in.

  “Jesus, this feels like heaven,” he panted, holding himself completely still for several seconds to let her get used to his full possession, even though the effort was visibly testing his physical control. “You’re tight as a fist, love, but so wet and hot and delicious around my cock. I want to stay just like this for as long as I can, enjoying every second of having you, but I need to come too badly right now.”

  “It’s all right,” she whispered to him, stroking his chest comfortingly. “Please. I want you to.”

  With a groan, Max began to move inside of her, still with control but with enough force that she couldn’t quite stifle the tiny whimpers of pain that escaped her throat. He was too big, she thought wildly, far too much for her, and all she could think about was how unprepared she was for this, how she felt completely dominated by his big, powerful body. But when the tears began to slowly seep out the corners of her eyes, she shut them tightly, determined that Max not notice her discomfort and think he had to stop.

  As if sensing her discomfort and rising fear, he kissed her then, immediately distracting her from any anxiety she might have been experiencing. His hand cupped her breast, tweaking the nipple between his forefinger and
thumb, and she sighed with pleasure, her earlier discomfort suddenly forgotten.

  He gave one final, powerful thrust, his body stilling as he climaxed, his head falling back as he cried out his pleasure. Jill glanced up at him from beneath her wet lashes, and the pain was instantly forgotten as she stared at him, enthralled. He was so magnificent, so primal and thoroughly masculine, that she couldn’t help touching him - running her hand up and down his chest before flattening her palm over his taut abdomen. She had been so tense and worried about losing her virginity, about the pain that really hadn’t been all that bad, that she hadn’t taken the time to properly enjoy his beautiful body, hadn’t felt quite brave enough to caress him in the same way he had done to her. But here and now, when he was still shuddering in the aftermath of his orgasm, when he was perhaps a little vulnerable and therefore less intimidating, she could touch him a bit more freely.

  Max gave a little shake of his head, then blinked his eyes open slowly. He grasped her suddenly bold hand in his, stilling its motion.

  “If you keep that up, sweet, I’m going to want a repeat of what just happened,” he told her in a husky voice. “And since you’ve had quite enough for your first time, we should save any additional experimenting for later. Easy now, hmm?”

  Jill bit down on her lip as he slowly and carefully eased out of her, though try as she might she couldn’t stop herself from wincing. Max frowned, and turned her cheek to one side, his thumb finding the telltale trace of tears.

  “I hurt you. Damn. And when I was trying so hard to be careful,” he swore softly. “I’m so sorry, love. You should have told me.”

  She was quick to deny his assumptions. “No, no! It didn’t hurt, honestly. I mean, there wasn’t actual pain, just - well, like I said before, a little discomfort, some tightness, that sort of thing. But you didn’t hurt me, Max, I promise.” She touched his lips with her fingers. “You aren’t capable of hurting me,” she whispered. “You couldn’t hurt anyone.”