The Deep Dark Want

Since Cordelia would be too close to Buffy, Willow, and all the mayhem outside, Xander decided to try Casanova on Ms. Calendar. The time-imprisoned teenager has looped enough to know the seductive teacher would be alone in the computer lab of his high school. Xander finds it odd to be seeing her again after so long. It feels as though it’s been a thousand cycles since he’s even heard her voice. Even moments with his friends can be spread between tens or even hundreds of loops. Discovering Casanova’s costume and what he can do with women was like getting too close to a planet with a strong gravitational pull; difficult to escape.

Entering the deserted hallway of his school in his Casanova costume, Xander looked around the eerily silent hall and said to himself, “It’s been too long.”

Instantly, Xander thought about the time loop and hoped this worked. He needed to get out, but until he figured out how, he needed to maintain sanity. He looked up at the cheap placard on the wall that said Computer Class, then at the Library across the hall. Xander knew Giles was in there, but he also knew the man couldn’t help him.

Xander had already tried enough loops researching everything he could in the library. Even with Willow, other than a simple time loop spell for clocks, they found nothing on the scale of Xander’s problem. Giles, Willow, and even Ethan couldn’t help him. He turned his back on the library that’s like a second home—only better than his actual home—and gripped the handle of the computer class door at six on the dot.

Casanova was as suave as ever as he entered the classroom, immediately eying the foxy brunette at the end of the computer room. Her sharp jawline, full red lips, penetrating almond-shaped eyes, and dark-brown hair—messily done up—made her the most captivating teacher in the school. She was slim, with modest-sized breasts, and sensual, graspable hips. The professional charmer could tell that aside from her face, her gorgeous legs leading up to her perky ass were her best features. She was a beguiling beauty, and Casanova was eager for them to submit to each other.

Sadly, within the shorter time frame of the curse, he couldn’t get anywhere with the beautiful teacher. Miss Calendar knew Xander on a personal level and quickly realized that he wasn’t himself. She easily resisted the player’s advances because she was only interested in helping him. Ms. Calendar kept trying to talk him out of the persona, then simply raced to the library to get Giles to help him. When the curse ended, nothing meaningful happened with the sexy teacher.

Xander needed to set the stage. Since it appeared Casanova needed more time, he set up the Janus curse to last longer by calling Angel to come early to protect Buffy and Cordelia. He also subtly dropped Giles’ name around Ethan to urge him to move the statue to a second location and dropped Ethan’s name around Giles to make the man leave the library much earlier. Xander hoped with enough time and no one around to intervene, Casanova might figure out the script to turn Jennifer Calendar’s rejection into consent.

Upon entering the warm computer classroom, Casanova could once again tell the sensual teacher was sharp-witted and Xander knew he loved savvy and educated women. Intelligent women always wanted something and the adventuring philanderer had just enough intelligence, money, and power to seduce any type of woman he wanted, whether a maid, nun, lady, wife, or socialite. Miss Calendar’s want was to help Xander. With her knowledge of magic, she assumed he was possessed and needed to take him to Giles. However, the manipulative man refused to go.

Casanova stood there as she tried to pull his elbow and told the thin woman, “I’d certainly be willing to acquiesce to your request, my dear, however, how could you make demands of me without proper compensation first?”

Jenny looked at her possessed student—acting like an 18th-century aristocrat—and she was in disbelief as she asked, “Do you seriously want money right now?”

He closed his eyes in amusement before replying, “I find monetary wealth to be quite dull and overall useless to my truest and most enduring desires.”

Eying him suspiciously, she asked, “Which would be?”

Casanova leaned closer with perfect posture as he answered, “If you’d like me to be the moth, my lady, you’ll need to become the flame.” She scoffed, then took his wrist and pulled. Casanova didn’t budge for several seconds before calling out, “Cold! Much too cold. I see not a light, not a spark, not a flicker of warmth.” Xander took her hand, pulled her to him with ease, and quickly snaked it around his lower back. Their faces were inches apart as he spoke, “Warmer.”

“Will you stop dicking around,” she asserted, removing her hand from his.

When she tried once again to pull the boy toward the door, he wouldn’t move as he once again called, “Colder!”

With growing irritation, Jenny dropped his hand aggressively and yelled, “Xander!”

“I don’t know who that is,” Casanova casually said, mildly enjoying her frustration. “But if you wish to move Giacomo Casanova, a radiant beauty such as yourself can most certainly tempt me.” Xander walked around her backside, and when she pivoted around to keep him in front, he leaned forward again. He was so close to kissing her when she backed away, aghast.

“No,” she exclaimed, eying him warily, like she needed to be careful with him. “Stop! I’m not doing that. I can’t.”

“Then neither can I,” Giacomo easily responded before walking around the room without a bother in the world.

“Xand-” she tried when he cut in, “I’m afraid I-” “Fine! Giacomo,” she quickly corrected. “We need to figure out what’s going on, so you need to come with me right now. It’s for your benefit.”

Xander pressed his lips in a fake smile before remarking, “Colder. So very cold, I expect frostbite any second.”

Jenny sighed audibly before pressing the heel of her fists into her eye sockets. After a few seconds of silence, she sighed once more with determination. Jenny walked up to Casanova, caressed his left arm, getting a smirk out of him before planting her palm gently on his chest. She gazed into his amused eyes before softly asking, “Please?”

“Oh,” he hummed, leaning so close their noses almost touched. He asked, “Just a little more.”

With much more effort, Ms. Calendar committed to asking the possessed boy in her most sultry way. She pressed closer so her leg was between his and the tips of her breast grazed his chest. With big pleading eyes, she seductively asked, “Please, Giacomo. Won’t you come with me?”

Casanova smiled knowingly, remarking, “You do know your charms quite well, I see. To tell you the truth, I sense a deep-seated soul in you. The beautiful vessel before me appears to be but half the woman there is, isn’t there? Who are you truly, mademoiselle Calendar?” Jenny blinked in surprise and backed away. “Come now, do not be so startled.” Taking her hands and kissing them, he told her, “Your true self is the woman I crave, for what can be satisfying about half a meal?”

Thinking she had a chance, Jenny simply gripped his hands tightly and tried to pull him out of the room. From within his harnessed mind, Xander could tell Casanova anticipated she would physically force him. The professional philanderer could tell the difference between true submission and someone simply pandering to him. Xander didn’t budge an inch, and after a minute of constant pulling, Jenny gave up.

She glared at him but Casanova only smiled before assuring her, “If you’d like me to accompany you to a destination of your choosing, then I must insist on a kiss as payment, indecent though you might find it.”

Balling her hands into fists, she sternly asked, “How about I just knock your teeth out?”

Unworried, Casanova shrugged easily as he teased, “Do as you must, my lioness, but know my price will not change.”

Her steps forward easily telegraphed her intentions for an altercation. Once close enough, she tried to kick his shin, but he dodged her leg and prepared to do no more than defend himself. He would not attack, even when she charged forward and wrapped her arms around his torso to hoist him with great effort toward the door. He didn’t move more than a couple of steps, but she kept pulling.

Casanova enjoyed hearing her grunt and the smile on his face, so close to hers, annoyed her to no end. She suddenly pushed him away to force him to lose his balance, before pulling again. She only managed another second step and no more. Jenny leapt away from him when she felt his palms massage her hips and lower back. Instinctively, she grabbed a textbook on the nearby desk and hurled it at him.

He easily dodged it before laughing loudly, annoying her further as he boasted, “Such fierceness and yet you hold yourself back.”

“Xander-”

“Giacomo-”

“You’re not Giacomo Casanova,” she yelled back. “You’re Xander Harris! One of my students! Who I will not kiss!”

Other than her panting breaths, silence descended between them for a moment. Casanova stood straighter with his impeccable posture before easily reading her like a book. “Though your words seem to care for this student of yours, your actions would say otherwise. For you would rather physically incapacitate him with hazardous projectiles than pay me the paltry sum of a single kiss?”

“Xander, please, we don’t know what’s going on,” she pleaded with wide, animated palms. “This could be really bad!”

Moving forward until he was mere inches away from her, he leaned down to articulate, “Then I suggest you overcome your tired notions of social decorum and come to the conclusion that you are a woman refusing to use the only enchanting power over me that the God Almighty has so wonderfully bestowed upon you.”

He’s close enough to note the specks of red and green in her glaring brown eyes. Jenny squeezed her eyes shut, growled a bit in helpless frustration, then grabbed the sides of his face before giving him a quick kiss. Xander could tell Casanova expected that as well. Before she could pull away, he smoothly snaked his arm around her waist, rotated her body, and leaned her backward in one fluid motion. She yelped at the startling feeling of falling, but he held her firmly and kissed the surprised woman. Feeling as though she was going to fall back, her hands reflexively wrapped around his neck as he kissed her.

‘Wow,’ the restrained consciousness of Xander gasped. He couldn’t believe he was watching the hot teacher kissing him. The shock of it made him forget all about the time loop.

It took Jenny a long second of kissing to realize what Casanova’s done, another second to realize his tongue somehow ended up in her mouth, then another two seconds to ignore his impressive technique before finally tapping the back of his neck. She expected him to bring her up, however; he scared her with a quick drop, making her hold tighter and squeezing another four seconds of impressive kissing.

She just barely restrained her moan when he eventually brought her upright again. Jenny was surprised she didn’t hate the kiss and felt flushed. She hated him and the entire situation, but the kiss left a very warm impression. As Jenny straightened her shuffled clothes, the irate woman was ready to punch him if he gloated, but he seemed over it already.

Casanova walked to the door before proudly stating, “Now, let us see this Giles of yours.”

The pair then go across the hall and enter the deserted library. Finding no one on the center floor, Jenny rushed through the aisles on the elevated floor before rushing to his office, but she didn’t find hide nor hair of Giles. She realized whatever the problem was, either affected the Englishman as well or he was out trying to solve it with the others. The educator reasoned the next step had to be tracking down Giles or Buffy so they could help Xander.

Rushing back out to the main floor, Xander was standing with perfect posture in the center of the room with an arm affixed at the small of his back and eying her with a mixture of awe and desire. The fact that the persona had Xander’s face but was an impressive kisser unsettled her, among other base feelings she ignored.

“Let’s go,” she told him. As she walked toward the exit, she explained, “we have to find Giles or Buffy. Hopefully, they can tell us what’s going on.”

Xander didn’t move. He stayed at the center of the room. When she turned to him with a look of confusion on her face, as if to ask, ‘what now? Let’s go,’ he shook his head and told her, “The bargain was for a single kiss to relocate me to a single location. If you wish to move me elsewhere, it’ll naturally require another payment.”

Furiously inhaling deeply kept her from cursing as she cut herself from finishing, “You motherfu- mmn! Mmmnnn.”

“I understand,” Casanova said with Xander’s winning smile. “But I’m afraid I’ve developed a vigorous addiction to the taste of your sensual lips. They are utterly delectable,” he slowly finished.

“Fine, stay here,” she angrily told him, unwilling to put up with his shenanigans. “I’ll find him on my own.” When Xander moved to leave, passing her toward the exit, Jenny called out, “Xander! No, you have to stay here-”

Xander’s arms swiftly took her frame by her thin waist, and the friction dragged her blouse up enough for his hand to grip the skin of her lovely hip. Massaging her tender flesh with his thumb as he eloquently expressed, “You ask so much of me, and yet I only need so little in return.”

Their hips were touching, but she leaned back, conceding more of her leverage to him. She sternly looked into his brown eyes and firmly told him, “No.”

“I see and am saddened so,” Casanova said, releasing her from his embrace. “Well, I shall not, nor will I ever, force a woman to act on her innate salacious desires.”

Jenny smoothed down her blouse and nodded as she declared, “Good! You’re not a total scumbag then. Stay here. I’ll be back.”

Trapped within his mind, Xander’s consciousness raised his eyebrows as he watched his possessed body casually walk up the seven steps to the left that lead to the aisles of bookshelves on the elevated floor. He then gripped the railing and hurled himself onto the wooden table below with a bang loud that echoed throughout the room. Xander thought of wrestlers throwing themselves over the ropes to a table below, only he was the one getting hurt.

Jenny was halfway out the double doors of the library when she heard the meaty bang, then a wounded groan, and ran back in. Rushing to him, she saw him on the tile floor beside the sturdy table, gripping his shoulder as if injured. The chairs and table were pushed away, but none of the furniture was broken.

She helped the injured boy stand as she yelled, “What are you doing!”

Casanova accepted the pain and allowed her to check his aching shoulder as he voiced, “I couldn’t resist my curiosity to learn just how important this boy is to you.”

Stepping back, she glared at him as she attested, “So you are possessing him!”

“I am doing nothing of the sort,” he replied with a smirk, rotating his injured shoulder. Fortunately, Xander couldn’t feel it as the persona voiced, “From speech to form, I am the one and only Giacomo Casanova.”

Squinting and knitting the skin between her brow, she asked, “Then why say-”

He closed the distance between them but stood upright with dignity as he explained, “You seem to believe I am someone who I am not, thus, my brief experiment.” She looked at the elevated section where he jumped from, the wood table, then back at him as he continued. “If you would like me to refrain from injuring this body you claim to believe doesn’t belong to me, odd as I find that, then the burden of convincing me falls squarely on your slender shoulders.”

Her hands balled into fists as she realized the detestable lengths this man will go for his sexual urges. Infuriated, she yelled, “You’re even worse than a scumbag! You said you don’t force-”

“I leave the choice entirely to you, my lady,” he interrupted over her voice. He tilted his ear toward her to better hear her consent. When she held her tongue, Casanova asked, “No? Very well.”

The possessed Xander walked up the stairs again while she remained rooted in place, unwilling to succumb to his emotional manipulation. He looked at her resolve, and with his raised brows, gave her a second chance to stop him. Other than her tight jaw and angry eyes, she communicated nothing else. Xander proceeded to then slam his face into the wood railing.

“Xander,” she yelled as she rushed up the stairs to him. The trapped Xander within felt a slight dull pressure he assumed was the zing of pain and couldn’t believe how far Casanova was willing to go. As the beautiful teacher checked his bleeding left eyebrow, she begged, “Stop doing this!”

She pulled him away from the railing by the hand and toward the book check-out desk for tissues as he replied, “You care for who you believe me to be-”

“Obviously I care about my students-”

“Then if you’d like me to stop,” he cut in as they reached the check-out counter. “Demonstrating how much you care as a woman would certainly travel a long way.” The pensive woman was eerily quiet as her hands grabbed the tissues and pressed them against his left eyebrow. She wasn’t gentle when she pressed the tissue against his cut, but the sight of his blood was upsetting her.

Casanova rested a palm tenderly on her slender shoulder, making her sharp, almond eyes focus on his as he softly voiced, “I understand your hesitation, my captivating lioness, but, I am merely removing the obstacles from your path to unmitigated pleasure. After our liberating union, you are free to deny and claim whatever sentiment you see fit.” She returned her focus to stopping the bleeding as he continued, “I ask again, shall I continue to test my theory or will you convince me to stop?”

Again, Jenny held her tongue. At her tensing jaw and brows, he nodded, stepped away from her, then banged the other side of his face into the hard surface of the Check-Out desk. The Xander harnessed within his mind felt his nose tingle a bit, like someone was gripping it too tightly, but nothing more. It didn’t feel broken, but blood began to drip from his nostril.

Casanova turned to her and asked her once again with his eyes for an answer. Though she clearly wanted to help, she forced herself not to move. She appeared in turmoil, raging with internal conflict as her fists were balled up tightly and she remained silent. Casanova tilted his ear closer toward her for an answer. When he didn’t get one, he fished around the desk beside them for any item that would work.

“Where did I see- ah.” Casanova grabbed the pen on the counter and before she could stop him, he promptly stabbed himself in the thigh.

“ALRIGHT! Stop! Just stop!” She repeated as she checked his bleeding thigh.

‘Holy hell, this guy’s crazy,’ Xander thought in amazed disbelief. Xander had Casanova’s memories to know he would go to any lengths to be with the girl he wanted, but to see it in person felt unreal. Jenny slowly removed the pen, and from the red streak at the tip, it didn’t appear like more than half an inch pierced through his skin.

Casanova leaned down to softly ask the woman inspecting his thigh wound, “Why should I stop, my lady? This form is my property and I can do with it as I please.”

Shaking her head, Jenny grabbed his hand and forced him to follow her out of the library. He hopped along beside her as they went back across the hall to her computer class. Casanova only allowed her to move him because he could see the submission in her eyes. She didn’t want to cross that line with her student, but she certainly didn’t want to do anything in Giles’ space. Jenny closed the door behind them and they were alone in her classroom.

Moving behind her, he pressed his chest against her back as he genuinely began, “I sympathize with your frustration. Truly, I do.” She didn’t move as he continued, “But it is a noble thing, accepting your primal urges to save this boy you seem so fond of. Think of nothing but that and allow yourself to be simply a woman with desires any man would be honored to satisfy.”

With a resigned sigh, Jenny pressed her forehead to the door as she insisted, “No clothes come off.”

The costumed Xander turned her around and looked her subdued face in the eyes before assuring her, “You have my word.”

As a leading expert on the subject of pleasuring women, Casanova knew what mattered most for them was being in the moment. When they think of concerning things like their husbands, getting pregnant, or their performance, it always leads to an unsatisfactory experience. And he can tell when they’re not fully in the moment. To make Jenny feel more present, he took the handkerchief from his coat and blindfolded her. As he did so, he asked her to match his breathing. Long, deep breaths oxygenated her cells to a higher degree of sensitivity.

It’s why the palm he suddenly placed on her sternum felt hotter and more sensual; as if they were doing something forbidden. Jenny had a weakness for the forbidden. Casanova pressed his body against her, keeping her sexy form between him and the door. The blindfolded woman felt his restrained erection against her belly as his nose gently brushed against her chin, lips, and nose, subtly tilting her face away.

“In and out,” he softly voiced, breathing in and out to remind her. Pressed flat against him, her breathing matched his own, pressing her B-cup breasts more into his inhaling torso. As he had the beauty match his breathing, his hands began massaging her slender body, beginning with her lower back and hips. He leaned in and pressed his lips against Jenny’s, but only for a moment. He could feel her mind was thinking too much.

He pulled back to encourage, “Set aside your reason, my lady…”

He kissed her again, pressing his lips expertly against hers. She’s still not returning the kiss, but with his hands coaxing more tentative pleasure from her, Casanova knew it was only a matter of time. He felt a quality hunger in her, as if it’s been a long time since she felt a man’s touch. He knew how much she wanted release, even if it wasn’t from him. Casanova pulled away and whispered, “Embrace that deep, dark, want.”

As his hands caressed her sensitive hips, he kissed her once again, lowering his pelvis to press more against her womanhood. And when he pinched her butt, she squealed into his mouth, allowing him to dive his tongue inside.

“Mnn,” she moaned as his tongue danced inside her mouth. Blindfolded and hot against him, Jenny felt like her senses were acutely sensitive to his machinations. His hands, in particular, were very adept at finding her sensitive spots and caressing far more pleasure than she wanted to feel in this situation. His innate intuition of the pleasure centers of the female form, and for several long minutes, his hands massaged her sexy body with expert influence.

Casanova ended the kiss and nibbled at her neck. Something about her wiles told him she liked it rough, and he massaged her ass with a strong grip, coaxing a small whimper out of her luscious red lips. Her nipples hardened against his chest, her pelvis felt hotter, more humid, and he could feel her body softening to accept him. Casanova kissed and nibbled back to her red lips and was greeted with a more willing kiss. From his hot body pressing her against the door, strong methodical hands caressing her, to the erection she felt pulsing against her stomach, a blushing Jenny was losing her ability to think.

To keep her in the moment, Casanova pulled away and nibbled her earlobe a bit before whispering, “My hands will not take your garments off. However, they will go underneath them.” It ensnared some of her reason back and her jaw moved to speak when he added, “I agreed to your terms. I’m a man of my word.”

Her blindfolded head turned left and then down in thought. When she raised it again, he kissed her, and she allowed it until his warm hands moved deftly under her blouse. At the hot feel of his hands on her bare skin, she pulled away to ask, “How much longer?”

“Five minutes,” he whispered between nibbling at the sensitive spot on her neck. He was so good her head lulled and rested on his shoulder.

“P-Promise,” she gasped as his hands pulled and contracted her tense back and hip muscles to vibrate with ticklish satisfaction.

His clever lips pulled back to speak, “A man of my word. You may count the time yourself, my dearest.” He continued necking her sensual nape as his hands masterfully coaxed all manner of pleasure from her soft, sensitive breasts. Her hard nipples were teased, pinched, and caressed with care, and Jenny was once again being overwhelmed by how good he was.

She couldn’t stop how aroused she was feeling and leaned against him, resting her head on his shoulder and breathing deeply. Casanova removed his right hand, making her flesh tingle, unbuttoned and unzipped his jeans, which sounded like a chainsaw in Jenny’s ears. His right hand guided her left hand to his steely erection under his open jeans, but over his boxers, and he kissed the aroused woman as his hand kept hers against his pulsing member.

When his left hand pinched her nipple, her moan opened her mouth more to heavy tongue caressing, and for the first time, Jenny kissed back. It was instinct. She was being overwhelmed with a buzzing pleasure and she needed to return some of it to keep her sense of control for the next few minutes. Knowing that it would be over soon, Jenny simply went along with it. She didn’t think about how good he felt. Only that it would be over soon, so nothing she did would really matter. As if he read her thoughts, he tested her resolve by deftly moving his right down her twitching abdomen to the hem of her skirt and then under her panties.

“Mnn,” she moaned before stopping their kiss. “Wait-” she voiced before catching her breath. His fingers were already touching her sensitive slit. His fingers were quickly becoming coated with her love juices, making her equal parts hot, aroused, and embarrassed.

“Absolutely dripping,” he remarked.

“Wait,” she tried.

“Why, when you’re grasping mine,” he replied, and Jenny hadn’t even noticed her hand was indeed gripping his rock-hard erection through his boxers. “We have but a minute and seconds.” His fingers were massaging her wet sex, and sensing how confident he was added to the pleasure, making her entire pelvis shudder at his ministrations. “You’re so close, my dear,” he whispered.

The flushed Jenny remained quiet even when he inserted a finger as his thumb expertly massaged her extended clitoris. Casanova fingered her sensitive love tunnel as masterfully as everything else he’s done, moving her closer and closer to the ever-glorious edge with surprising efficiency. Seconds felt like minutes, and Jenny couldn’t keep her sweet whimpers and moans from escaping her clenched jaw. She was blushing furiously, and even under the blindfold, her eyes were closed. Everything he was doing made her knees weak and her body sparkled.

“Holy shit,” she gasped, pressing her face into Xander’s neck as Casanova curled his fingers inside of her dripping sex, stroking a bundle of pleasure nerves. The ecstasy shot up her spine to her buzzed brain and she knew her wanton body was on the precipice of a massive orgasm.

“I’m… I’m almost,” she started as her legs started to tremble at the imminent release when—from across town—Giles seemingly smashed the statue of Janus.

Xander felt himself being released from the harness whoosh into his own body. His senses were no longer dulled by the costume. The pain from his wounds, pleasure from her hand, and shock of being dropped into that moment stopped his soaked fingers, making her open her eyes to the sudden halt of pleasure.

Angrily, she reflexively demanded, “Why!”

Slowly, a surprised Xander raised her blindfold before cautiously replying, “Uh, I’m... back.”

Still wrapped in dwindling tendrils of pleasure, a panicked Jenny Calendar paused, as if she wasn’t sure that mattered when factoring what she was on the verge of experiencing. In that specific loop, Xander waited on her lead. It took her a few conflicting seconds, but when she regained higher brain function, she hesitantly pulled away, leading to a very awkward rest of the night. Giles showed up to the library, where they waited twenty-five minutes later, irate by his encounter with Ethan, then Xander walked home to repeat the day again.

In the following loop—because Xander couldn’t refrain himself from doing it again—the very moment she paused when she realized he was back, he didn’t wait for her to lead. His fingers continued pleasuring her. Her will to stop was replaced with her need to climax—to get off—and she didn’t stop him.

Pumping curling fingers as his thumb massaged her love button, she gripped his body and pressed her forehead into his neck as the fat pleasure coil at the core of her womanhood finally burst. Her pussy clamped on his fingers as her mouth opened into an oval O. Like a minute-long continuous explosion of fireworks on the 4th of July, her body rippled continuously with every wave of pleasure wrecking her system.

Xander’s brain was also closed to higher reasoning as he enjoyed the feel of the shuddering Jenny against him. To experience his sexy teacher lean her feverishly hot weight on him, pressing her breasts and hard nipples against his chest, was so exhilarating, being trapped in a time loop didn’t even bother him. His forearm burned with lactic acid buildup from the constant jerking motion and his throbbing cock ached to be snug inside the beautiful woman.

Xander loved it, wanted more, and asked, “Me too?”

At his voice, she regained her senses and realized her hand was still stroking his dick. Even if she felt very much aroused, she felt more clear-headed, and Jenny slowly removed her hand. Xander did so as well, and to his own surprise, tasted his fingers in front of her, eying her with daring as he did so. With her half-lidded, seductive eyes, she returned a wanton expression of arousal, but held herself back.

At Jenny’s insistence, they waited for Giles in the library as far apart as they could. Neither one said anything out of a mixture of shame, desire, confusion, and expectations. But more importantly, they stayed quiet because when Xander tried to make light of the situation, she pleaded with him not to speak. Her shame mixed desires couldn’t take it when he asked, “So, they should probably put a warning label on this costume, huh?”

Her glare made him remain quiet.

When Giles finally returned to the library, he had a brown bag in his hand Xander assumed contained the broken pieces of the Janus statue. More importantly, the man was very distracted and irate. He barely explained the gist of the night’s mayhem to them and couldn’t see Jenny trying to reach out to him. He didn’t even notice Xander’s injuries. The mildly abrasive Giles quickly explained having to deal with a curse that affected the town’s people, then dismissed them to be alone.

“That’s it?” The flustered Jenny asked with frustration, “You had to deal with a curse?”

“P-Please,” Giles voiced halfway to his office. “We can speak more tomorrow. Good night.”

Xander cautiously asked Miss Calendar, “Take me home?”

Giles leapt at the chance to be alone and absentmindedly told Jenny that would be a good idea before hastily walking to his office and closing the door swiftly behind him. The beautiful woman watched Giles speed away before turning to Xander. At the sight of him, she couldn’t help the blush rushing to her cheeks, likely recalling what they had just done. Raising his eyebrows to ask for a lift again, a despondent Jenny sighed before nodding.

On the quiet drive to his house, Xander embraced his daring and put his hand on her thigh, and in that loop, she slowly removed it before dropping him off, then rushing home. In the following loop, after being dropped off, Xander took his father’s car to her place and learned she went straight home to relieve herself with her purple dildo. He had to knock on her door repeatedly and run away. That level of annoyance told the Sherlock and Casanova within that she was pleasuring herself and didn’t want to be interrupted.

On the following loop, he asked her just as her hand was about to remove his from her thigh, “Why go home to a toy?” Then he squeezed her hot thigh, noting the signs of desire, restraint, and conflict on her sharp face. Having been Casanova enough times, he could tell she wanted to feel more, but was also cognizant of all the reasons not to.

“You helped keep that psycho from killing me,” Xander tried. “Let me help you.” After thirty tortuous silent seconds, Jenny hesitated to turn the steering wheel several times before deliberately turning her car around. Feeling a new adventure ahead, Xander cautiously asked, “Where are we going?”

“I… you’re hurt. I have a med-kit at home,” she hesitated to reply, then drove the rest of the way to her apartment in silence.

Xander learned in that loop to keep quiet and not talk his way out of her apartment with dumb and immature jokes. In the following loop, she bandaged his wounds in silence. They were in the living and dining room area of her one-bedroom apartment. Xander was seated on her kitchen chair as she disinfected and bandaged the cut on his forehead. When it came to his leg, Xander took his jeans off and leaned on the edge of her dining table. Jenny paid attention to the hard-on he wasn’t hiding by not looking at it while she treated his bloody wound. The moment she was done, he leaned over and kissed her.

She pulled away to affirm, “One night, you hear me? One night and nothing more.”

“Promise,” he said, but he knew he was going to come back for more. Having sex with someone he knew was far more exciting than the sexy strangers he was doing. And though he knew it’d be sad that she wouldn’t remember, he put that out of his mind for the moment. Being able to have sex with the gorgeous Jenny Calendar was too amazing to waste brain cells on any other thoughts.

Still, with no practice on her as Casanova, Xander knew he’d have to learn her erogenous zones on his own. Fortunately, he accumulated a wealth of experience and used the first few loops to read her body the way Casanova does and react accordingly. Keeping her in the moment, he wrapped his arms around her slim waist and lifted her off her feet.

“EEEKKK!” Jenny yelped in surprise, holding herself up by his shoulders.

Eying her like he was ready to devour her, he asked, “Bedroom?”

Jenny signaled to her left, and he walked them into her dark bedroom. Xander knew she’d be less nervous in the dark and feel more sensations in her feverish body without her sight. With nothing but moonlight coming through the window, he laid her on the bed before snatching her lips once again. Their tongues played with each other in her mouth as his deft hands removed each article of her outfit until she was in her underwear.

He pulled away before dragging her butt to the edge of the bed, where he teasingly pulled her panties down her sexy legs. Xander then spread her legs, massaging her inner thighs and basking in her woman scent. The eager teenager could see she was leaking before he began lapping up her savory nectar, and Jenny closed her eyes at the sensation of a skillful tongue devouring her melting sex.

“Mmnnn,” she moaned as her feverish body was so aroused by his eager lapping, she squirmed in place. She unclasped her bra, releasing her tits from their cotton confinement so she could fondle her own breasts. Her hands caressed and stroked the warm, smooth flesh as she pulled and pinched her hard nipples.

Feeling her inner thighs tremble, Xander hummed softly as he ate Jenny out. His hands massaged her ass and thighs as his tongue insistently probed her dripping vagina. Her moans increased in volume and frequency the longer they went. Despite how much he relished her sweet pussy, he paid attention to her reactions, like Casanova would, and found what she liked from the catalog of examples in his mind.

It shocked Jenny how good the teen between her legs was, and that surprise only made her more sensitive. When she began bucking her pelvis and contracting around his lapping tongue, he could tell Jenny was getting closer. Xander inserted a finger into her dripping hot hole as he began sucking and licking her sensitive clitoris, ripping out a deep moan from her open mouth.

“Xander!” she called out. “I’m almost…” He inserted a second finger and rotated his tongue as he sucked at her love bud. “Right there! Right there!” she yelled when his fingers caressed her G-spot. His curling fingers pumped into her leaking silk palace, building to a high crescendo.

“I’m Cu-Cuuumming! Oh my ffffffuck! I’m cumming, I’m cumming, I’m cummmmmmm,” she moaned out to the dark room as her back arched and she climaxed into his mouth. Her pelvis bucked sporadically as her love mound quivered for minutes.

Jenny felt her legs be raised and hooked on his shoulders before his cock was sliding into her sensitive pussy, spreading her dripping slit by a respectable margin. He’s not the biggest she’s ever had, and she half expected him to blow his load the moment he put it in, however, she was pleasantly surprised. It was clear Xander knew how to use his manhood, and grew hot knowing that she was going to cum from his dick.

Xander groaned as he fully sheathed himself inside her. She felt amazing, and the fact that he knew her only added to the euphoria. He imagined all the guys in school who openly talk about fucking Ms. Calendar and filling her with their seed. Xander wanted to do the very same, but he couldn’t think about his desires just yet. He slowly pulled out as he lowered his pelvis. He mentally located her sensitive sex folds before slamming back in. As he slowly built a rhythm, clapping his pelvis under her thighs, Jenny gripped the bedsheets when her whole body started bouncing under him. Xander relished the sight of her B-cup breast bouncing with his every thrust.

“MMn… mmmmn… Yessss! Yess! I love it! Ah! Harder, Xander! Fuck me harder!” her wailing filled his ears as their musk filled the room.

When Xander felt her legs tense, he gripped underneath her knees and brought them to her shoulders before fucking her like she hadn’t felt in a long time. He pumped relentlessly in and out of her gushing womanhood And Jenny loved it. She recalled Casanova’s words and truly set aside her reason in favor of her deep, dark want. Xander felt like the lower half of his body was itching to explode, but he held firm because hers was trembling more and more. He knew she would be much more sensitive and wanted to cum with her.

Xander rammed his nearly six-incher into her yielding pussy, rocking the woman and the bed under him. Jenny couldn’t believe how much pleasure he was pulling out of her; as if he knew how and where to light her on fire. Her quivering sex was gripping him tightly, and she couldn’t stop thinking of how amazing the pleasure buzzing her brain felt. His confidence was too unexpected to not be overwhelmed by the boy pumping inside of her. Her whole body was his, and they both knew it. Jenny cursed and moaned as she felt her orgasm approaching with haste. Her legs trembled and her pulsing love tunnel gripped him harder as his thrusts became more forceful.

“I’m almost there,” she yelled as her back began arching. “Yes! Yes! Yes! Yeeuss! YESS! FUCCKK! I’M CUMMING! I’M CUMMING! YOU’RE GOING TO MAKE CUM! YOU’RE MAKING ME CU-CUMMMMMMMM!!”

Her legs spasmed shut around his waist and Xander brought his weight down on her as her quivering vagina clamped down on his raging cock. Her toes curled and her eyes rolled to the back of her head as her entire body was wracked with wave after wave of intense ecstasy. All electrical signals in her body snapped and crackled blissfully as her orgasm melted her from the inside out for several minutes. She was sweaty and boneless under him, but Xander wasn’t done.

He’d just managed to hold on and when she settled down some, he slowly withdrew before turning her listless body over and thrusting back inside her hot moisture center.

“AHHH!” she moaned, feeling another massive climax track her down again with a vengeance. She held onto the sheets as she called behind her, “Wait! I’m still sensitive!!!”

He cut her off when he shoved himself back into her moist slit. Xander groaned in tandem with her loud moaning. He loved the sight and sound of her sweaty form succumbing to the pleasure he was giving her. It’s what he always wanted; fucking Jenny Calendar, his hot teacher. The gorgeous woman was squeezing him harder, and he knew he was seconds away.

“I’m gonna cum,” he heaved around the vigorous flesh-on-flesh clapping. “Can I cum inside?”

“Do it! Cum- Cum inside me! Fill me up,” she yelled just before he buried his entire length into her tight, spasming lane and orgasmed inside her. When she felt a pool of hot liquid fill her insides, Jenny clamped down on his love tool once again and squeezed every last drop of his man-milk into her hungry womb. After a minute of heavy breathing, he leaned down to kiss her as their quivering bodies settled down from their high.

“Oh… my… God,” she hummed in delight, and that was more than enough for Xander’s flesh tower to stand right up. “Wait,” she tried when she felt him roll on top of her. “I need a little more time.”

“That’s fine. I’ll just be up here,” Xander replied, before taking her smallish, beautiful, tear-drop breasts in his mouth. He hooked his cock between her legs, and before long, they were rutting like horny animals again. Xander fucked Jenny in every position he could think of and came inside of her no less than nine times. He was simply too excited to stop having sex with her for long. Again and again, the pair did it in a variety of positions, losing themselves in pleasure, and all the while, Xander was paying attention to what made her moan the loudest to repeat them. After dozens of loops with the sexy Miss Calendar, Xander was capable of giving her multiple orgasms and making her scream his name to the high heavens.

Through the various loops, he had come to learn through their pillow talk that she’s been going through a dry spell. He had to ask, “How long?”

“…Seven months,” she weakly said, burying her head in her pillow from embarrassment.

“Seven months!” he yelled in shock.

“It’s not like I’m saving myself or anything, but…”

A look came over her and Jenny never finished that sentence, no matter how many loops he asked. Xander was fine with that. He didn’t want to get too deep since he could feel the monotony getting to him. He could save the things he didn’t know the same way his parents hid a bottle around the house, just in case he needed the jolt.

His first twenty times with Jenny were pure joy. The next twenty times were still fun, but felt increasingly repetitive. By the end of the next twenty, it was a grind for him not to think about waking up alone. Every morning, Xander would wake up alone on his smelly bed, in his disgusting room, and he could feel the steady loss of his hope and buildup of anxiety. The worst part was always the moments just before he reset.

Jenny would always hold him tightly, fully satisfied and slumbering. Her room was clean and pleasant with the moonlight streaming in, and he didn’t want to leave. She’d rest her head on his chest and her naked body felt so warm and comforting against him; it made looping back all the worse. Her thigh was over his and she was leaking his sperm from her essence, making him dread resetting. But, of course, Xander had no choice and always looped back.

Laying in his smelly bed after being ripped from Jenny’s embrace once again, Xander could feel how close he was to losing hope and decided on a change to retain his sanity. Rather than focusing on escaping the time loop, he remained stubborn about his deep, dark wants.

“Welp, Cordy,” he sadly said with a long sigh. “Guess I'll see you later.”