Dan's Narrative: Chapter 2

Dan's Narrative: Chapter 2

Once more, my appreciation goes to AlphaBetaCajun for his editing skills.

Please take note that all characters involved in sexual activities are above the age of eighteen.

On a Saturday, Dan and a handful of his friends were playing D&D in their game room, a custom they'd established in middle school. They were a crew of timid, nerdy types like Dan. These guys were into Anime and fantasy games, bonding over their shared awkwardness during their adolescent days. Dan had already endured some good-natured jibes about his friendship with Madeline, who was referred to as the 'Elf Queen' among them. The afternoon drew to a close when Sheila made an appearance in the room. Dan informed his friends he'd be back soon as he made his way to the hallway to speak with his mother.

She said greetings, "Hey dear, I had a little chat with Donna, Madeline's mom. What an enjoyable woman, which is no surprise. By the way, she and her daughters are coming over for lunch tomorrow."

"Oh, that's fantastic, mom. Do you need any assistance?"

"Just tidy up this area. I'm confident that Madeline's younger sister would enjoy playing some video games." She offered a warm smile as she departed from the room.

Dan continued to engage in the game for a while longer before cleaning the theater room. He wished to ensure everything was in order for Madeline's arrival. He also tidied up his bedroom across the hall. Although he believed no one would see it, he wanted to be certain.

On Sunday at noon, Madeline and her family arrived. Frank had previously left to enjoy a round of golf before returning to New Haven. Dan breathed a quiet sigh of relief upon learning this news. When Madeline disappeared with Frank during the night before, he pondered the image of her with Frank's large penis in her mouth. The thought instilled fear and excitement in him. He dismissed these thoughts, reminding himself that Madeline wouldn't be interested in Frank. The man was sixty-one years old, after all! When he'd engaged with his mother, he'd been forty-three, and despite maintaining his fitness, he deemed it impossible for an eighteen-year-old girl to find him attractive, right?

The family arrived in an older model Camry. They were all adorned in casual dresses, and their hair and makeup were well-done, yet a bit fancier than their usual attire. Donna had told her daughters to make an effort for lunch, and it was evident they were related. Donna and Madeline shared similar builds, while Trina was a few inches taller, standing around 5'5". They all possessed long, light brown hair. Trina had hers braided, while Donna and Madeline had theirs pulled up, cascading down their backs. Madeline's dress only slightly covered her knees, and the top was more fitting than her customary loose clothing. Dan's eyes widened as he gazed at the expansion of Madeline's breasts and her slender figure.

Mom invited them inside and indicated the living room for introductions. Sheila remarked that her husband was engrossed in golf but was looking forward to meeting Donna and Trina on a separate occasion. Sheila served her and Donna white wine, while the younger ones had sodas. They chatted for a while, and Sheila suggested that Dan accompany Trina and Madeline to his game room, while she and Donna continued their conversation.

Unpredictably, Trina found Dan's game room to be incredibly impressive. At 16, she was an enthusiastic fan of video games and thrilled with the opportunity to play on a giant screen. Dan relished displaying his gaming skills. After eating lunch, they spent two hours watching Anime. The room was dimly lit, with Dan and Madeline sitting behind Trina on the large, plush theater seats. He was astonished when he slid his hands over the armrest and found Madeline's. She held his for a second, then released, but before she relinquished her grip, she removed the armrest completely and situated herself beside him. Dan's heart soared, and as he turned toward Madeline to discuss the show, he felt her lips meet his check with a tender kiss. Madeline released his hand, and Trina scrolled for another video.

Sheila called the teens back into the living room, where she and Donna were seated. The three teenagers sat on the sofa, Madeline nestled between Trina and Dan.

Sheila voiced, "I'm so happy to finally meet you, Trina. Your mom told me how talented you are in volleyball. Dan's sister Samantha also plays volleyball, you know. She's spending this year at Alto Prep in California and will be competing for Stanford next year."

"Cool!" Trina exclaimed, expressing her admiration for Stanford University.

"This summer, Samantha will be back home for a visit, and she'd probably love to chat with you about volleyball," Sheila shared with Trina. "Apparently, the laptop that you and Madeline use for schoolwork isn't functioning properly. Dan, did you receive a new laptop for Christmas? If so, it's time to part ways with your old one, wouldn't you agree?"

"Definitely! I haven't used it since I got my new one set up. I'll go grab it!" He dashed off and returned a few minutes later, carrying his old laptop in a protective carrying case. "Here you go. The power cord and a wireless keyboard and mouse are in there, if you're interested."

"You two are extremely generous," Donna remarked while looking at them, one by one. "You just have to let me know what I should pay you for the laptop."

"Don't even think about it!" Sheila put a comforting hand on Donna's shoulder. "Dan got that one when he was a freshman and has been pressuring his father for a more advanced one ever since."

The Walters left soon afterwards, and Donna embraced Dan and Trina, thanking them for their kind deed. Madeline lingered behind, and as the others left for their car, she beamed up at Dan and wrapped her arms around him, whispering in his ear, "Thank you for being there for me. You're a wonderful person."

Dan felt like he was walking on air the rest of the afternoon. Later, Sheila found him in his game room, and took a seat next to him. Catching sight of Donna's short dress that showcased her legs and her trim figure in a tasteful manner, Dan couldn't help but envision her without any clothes on, considering that he had witnessed her in various stages of undress numerous times the last few months.

"Donna and I had an enlightening conversation while the children were playing games," Sheila began. "In spite of the challenges she has faced, she has performed admirably while raising her daughters without a father figure present. You have to understand that Trina and Madeline have been without a masculine influence in their lives growing up. Do you know that Donna is working two jobs?"

Dan responded with a headshake. "It doesn't seem like Trina has spoken much about it."

"I'm going to have a conversation with Frank about the possibility of helping Donna find a better job that won't require her to work such lengthy hours," Sheila explained.

Changing the subject, she asked, "How do you feel about the idea of Trina coming over after school? Since you and Madeline have some classes together, I proposed that she visits you both to do homework and pass the time together. You could also take her home after dinner."

Dan couldn't hide his grin. "I think it would be nice. But do you know what Madeline's stance on this is?"

"Donna is going to discuss it with her. Rest assured that Madeline would love to see you more frequently, and you would have some alone time with her as well." Sheila gave Dan a knowing smirk.

Madeline texted Dan that same evening, "The subject of me coming over after school has been brought up by our moms. I don't want you to feel like you're babysitting me."

Swiftly, Dan replied, "I think that's a fantastic idea! We can accomplish our homework quickly, then enjoy gaming or watching movies."

Later, a smiling Madeline texted him, "That sounds perfect!"

Dan noticed that she included the same smiley face she used previously when sharing Frank's message.

Monday saw Madeline riding home with Dan. They quickly finished their homework, then played some video games until dinner time. He drove her back home afterwards. She greeted him with a tingly kiss on the cheek at her apartment door. They persisted with this new schedule during the week that followed. They held hands when watching movies, and Dan finally summoned the courage to kiss Madeline, but both of them seemed to be a bit clumsy at it. They often spoke about life after high school. Dan was planning on attending college in Boston, while Madeline had her sights set on a community college in Billington for the first two years to save tuition costs.

The following Monday, Dan and Madeline were sharing a snack in the dining room before starting their homework. Dan noticed that Madeline was significantly quieter than usual, but wasn't sure what to ask her. She remained behind for a bit, chatting with Sheila, before rejoining him to complete their assignments. She became her usual self on Tuesday, and was perky again on Wednesday. Each day, Madeline and Sheila spoke privately for a while. On Thursday, Madeline and Sheila retreated upstairs the moment they arrived from school. Sixty minutes later, Madeline entered the game room, and when Dan glanced at her, his eyes widened. Gone was the jeans and baggy sweater she had been wearing earlier; instead, she sported a short blue skirt that ended mid-thigh and a tight tank top that highlighted her generous bosom and revealed two inches of her belly.

"Well, what do you think?" She inquired, panting next to him at the table.

"You look fantastic! Have you been shopping?" he questioned, baffled.

Dan couldn't help but gawk at Madeline. Apart from last week when she wore a pretty dress for lunch, she was always clad in long slacks and loose tops. In this top, he could see that her breasts were larger than his mom's and had no droop in them. They appeared more like softballs on her chest, her slender torso making them look even larger. Madeline cracked open her Calculus book and commenced with her homework issues. Dan got busy with his own homework, but he could not seem to tear his gaze from Madeline's chest every several minutes. They finished up their exercises, and Madeline twisted around to gaze at Dan, catching him staring at her chest. She leaned over and pressed her lips on him, leaning back and granting him a beaming grin.

"I'm content you like my new attire. Your mother claimed she had lots of clothes for me to try out if I so desired."

"I find you appealing regardless of what you wear." Dan stated as they strolled toward the dining room.

"But you favor this more, don't you?" She addressed him with a smirk.

"Yes, I do. Is that okay?"

"Sure it is, buffoon! I cherish how you gaze at me."

They arrived at the dining room and bumped into Frank Scanlin. Dan didn't expect him to be around, but it wasn't unusual for him to drop by on Thursdays and remain until Sunday. Frank, once more, transfixed the discussion, focusing his attention on Madeline. He commented on how tan she looked, making her blush when he referred to her boobs.

"You used to have a top similar to this one, didn't you, Sheila?" Frank inquired.

"This is the exact same top, actually." Sheila smiled at Frank. "Madeline fills it out better than I ever did."

"It suits you well, Madeline, except for your bra straps." Frank referred. "What size bra do you wear, Madeline? With your youth, I'm sure you don't require the assistance."

Madeline blushed crimson, but before she could respond, Sheila intervened. "She's wearing a 32B, yet it's a tad snug. She could go up to a 32C, but I suspect that would be a bit too large. She certainly does not need the support."

Dan's face went beet red as his mother and her lover conversed so casually about Madeline's boobs. After dinner, Sheila demanded Dan's assistance in clearing the table, while Richard beat a hasty retreat upstairs. Frank and Madeline retired to the living room. When the dishes were cleared, Sheila and Dan parked at the dining room table. Dan was a bundle of nerves, realizing that Frank would likely talk to Madeline about Dan's deflowering his own mother. He didn't think Frank would divulge that information to Madeline, but he was still anxious about it. Sheila could tell Dan was fidgety.

"Dan, I understand you're worried about Madeline, but I can guarantee you everything will be okay. Madeline and I have had some engaging chats, and I think it's beneficial for her to have a conversation with Frank as well. She requires the guidance of a father figure, someone who's not scared to voice their views." Sheila patted Dan's arm, understanding that like his father, he was overly timid to make the first move.

It was nearly half an hour before Madeline and Frank emerged from the living room. Dan could discern that Madeline's cheeks were flushed, but Frank seemed as poised as ever, his hand at Madeline's back as he led her to the room. He offered Sheila a nod before the two women went upstairs.

"Madeline is a nifty girl, Dan. Brainy, also," Frank smacked Dan's shoulder and strolled back into the living room. A few moments later Madeline and Sheila emerged from the living room. Madeline had returned to her regular garb, while Sheila had donned a lacy camisole and coordinating panties. The material wasn't sheer, but the shadows of Sheila's nipples could be discerned through it. The top stopped below her navel, exposing her panties, the back revealing a lot of her firm rear. She and Madeline embraced, then she walked into the living room as Dan and Madeline went to take her home.

"Your mother is so radiant," Madeline opined as they traveled to her apartment. "I wish I'll appear that fantastic when I'm her age."

"You will. I'm sure of it." Dan grasped her hand. "What, uh, were you and Frank chatting about?"

"Simply issues," she replied cryptically. "It's fun chatting with someone older and knowledgeable. You're not perturbed, are you?"

"What?! Of course not!" Dan stuttered, not wanting Madeline to think he had any grounds for jealousy.

On Fridays, Madeline and Dan would drive to her apartment. Once they got there, Madeline would lean over the car's console. And when they kissed this time, her soft lips parted, allowing her tongue to tease his, leaving him aching for more. She broke the kiss with a giggle, then Dan walked her to her door, giving her a good night hug with a lingering embrace. Dan's house was eerily quiet when he arrived. He could hear his mother grunting rhythmically, a sign that Frank was fucking her. Dan went to his room, shut the door, and soon enough he had his favorite porn video playing. He stroked his four-inch penis while watching a petite young blonde suck an old man's huge cock.

From then on, Friday became their routine. Dan and Sheila would go upstairs to the master bedroom, where the girls would talk and select clothes for over an hour. Meanwhile, Sheila would start dinner. Sheila resumed wearing her sexy, revealing clothes, and Dan wondered if Madeline didn't even wear a bra. Her outfit choice in the evenings was either tight or low-cut or both. Some outfits were so thin the indentions of her small nipples were visible. Madeline acted as if it was all normal. Frank began visiting every week again, staying from Thursday for dinner to Sunday. Her outfits became sexier when he was there. Dan remarked on Madeline's outfits, commenting on how her perky tits looked under loose tops and the state of her nipples in tight shirts. The sight of her slim legs and small, firm butt bore no resistance from him. She would stand and turn for him to admire.

Several weeks later, Madeline joined the Saturday D&D group. Some couldn't make it every Saturday, but their game never failed. Madeline's character was an elf named Muriel. The group's artist, Trevor, drew each character, the elven warrior sporting long brown hair and facial features like Madeline's. Her bow-wielding character's tight, revealing outfit exposed a significant amount of cleavage. Madeline blushed upon receiving her drawing, but proudly displayed it on the table.

Every night after dinner, Dan and his mom waited in the dining room, while Frank and Madeline went into the living room alone. Dan would stop the car a few blocks away from Madeline's apartment on Thursdays and make out with her in the seat. Fridays were even better as they'd head back to the game room for an hour or more of making out, with Madeline taking the lead. Only recently did Dan gather the courage to put his hand on her leg and rub it, carefully stopping short of venturing too far.

One Friday, several weeks after Madeline started wearing revealing outfits, she came down in a pale green sundress that just barely covered her firm butt. The top hugged her breasts tightly, displaying her hard nipples. Having noticed her outfit, Frank commented, "It looks great. But it would be even sexier if you undid a couple more buttons." Madeline smiled at Frank and turned to Dan, asking him, "Do you like it?" Dan nodded, unable to express himself before Frank once again spoke. "I think there should be even more of her assets exposed for our viewing pleasure, don't you?"

Madeline gazed at Frank, unbuttoning two more buttons on her blouse nonchalantly while keeping her gaze fixed on him. Only one button remained beneath her perky breasts, and with this removed, Dan caught a glimpse of the snowy skin of her upper chest and her taut nipples pushing against her blouse. Everyone in the room was riveted to the sight of the valley of flesh displayed for all to see, and Dan couldn't help but notice that Madeline's complexion was flushed. After a moment, Frank stood and moved away, following by Richard. Dan couldn't stop staring at Madeline's exposed bosom, his erection aching terribly.

An instant later, Sheila called out, "Help me clean up these dishes, then we'll chat."

Dan was startled out of his reverie; yet, when he turned to see Madeline already in the living room, having slipped out of her chair.

"Help me with the dishes, then we can discuss things," Sheila asked gently, breaking Dan's gaze from Madeline's chest.

Minutes later, Sheila and Dan were seated together at the now-clean table. His heart continued to pound as he envisioned Madeline disrobing for Frank. Though Madeline had been dressing more outrageously lately, the sight of her shirt half-undone sparked curiosity in him. The knowledge that his mom had been with Frank years ago only added to his unease. Dan struggled to express his concern.

"I like Madeline a great deal," he whispered hoarsely. "But your rendezvous with Frank bothers me."

"Well, Dan, you need to understand that Madeline is still grieving her husband," said Sheila calmly. "She's seeking help from Frank, and if you support her, everything will be okay, I believe," she added.

"I will," Dan murmured, staring reminiscently at Madeline's chest. He remembered how she taught him to kiss by example.

"You two are close, your mom and me," Sheila noted, her leg resting on his thigh as she leaned over to offer him encouragement. "Care to show me how Madeline kisses you?"

Dan's pulse raced at the idea, and he followed his mother's instructions, passionately kissing her. He was surprised to feel his mom's bare thigh under his hand, and he withdrew; yet, she quickly grabbed him, allowing him to slide his hand further, feeling the smoothness of her hairless pussy.

In that moment, the door swung open, and Frank entered, caught in mid-action with Madeline pressed against his side. Dan watched as his mom casually pushed Madeline away, sliding her hand between Frank and Madeline to cup her backside. Sheila and Frank turned and walked away, and Dan was left to ponder the evening's events as he made out with Madeline. He was allowed to stay late without consequence, and she pulled him down for a long, deep French kiss, her fingers undoing the button hiding her nipples. Dan's hand found her waistband and gaped her dress a little, leaving it displaying the sumptuous cleavage of her full breasts, with the edges of her nipples barely poking through the thin cotton.

Suddenly, Sheila appeared and claimed Dan's hand, leading him back to the table. "I hope you enjoyed that kiss, Dan," she cooed, as their lips met again. Her fingers moved over his cheeks, stroking him gently, and then she sent him back to clean the table while she tended to the leftovers.

He finished, bringing the glasses and dishes back to the kitchen. While Sheila rinsed them, he recalled how Madeline wore a dress without panties under it and wrestled with an erection as his fingers had brushed against her. The thought of his mom's naked thigh provoked his erection yet again; however, he relented, smiling wistfully.

"You like Madeline quite a lot, do you?" asked Sheila. "She's a good kisser, yes?"

He nodded, relaxing into Sheila's maternal care. Her gentle kisses were an unforgettable memory, but the sight of Madeline's exposed chest lingered in his mind. Sheila wanted to know if he thought her kiss was as good as Madeline's, but he couldn't say, so he simply nodded without verbally responding.

Sheila switched positions, sitting on Dan's lap suddenly, her pink dress riding high on her thighs. His eyes sparked with surprise as he saw she didn't wear any panties either, and the tip of his cock grew larger.

"Show me how you kiss Madeline now." Sheila demanded playfully.

He tilted his head, unable to respond, unsure if he should be.

"Kiss me like Madeline would," she suggested, moving closer to Dan and pulling his face to hers. He locked his lips with his mother's, receiving a sharp pang of guilt. After a daring moment, Sheila relinquished their lips and Dan found his hand casually resting against her naked hip. He squirmed instinctively when he touched her lips, remembering the volatile emotion sparked by her pussy, gratifying him with his first glimpse of her cleanly shaven pubic area.

Suddenly, Frank stepped into the room, his eyes darting between Madeline and Dan.

"I see you've taken Madeline's example and learned well, son," Frank praised. "I hope you show Madeline the same treatment; she's a superb kisser."

Dan nodded, stunned at the situation, only stuttering, "She's a very good kisser."

Sheila mouthed, "Thanks, Frank," and, saying goodbye, left the room with him. In time, Madeline took over; she straddled Dan on the couch in the game room, offering him her mouth. Dan's hand slid under her sundress and pressed against her panties. He hesitated, then adjusted her sundress to reveal the full extent of her impressive bosom.

"Quite a memorable kiss your mom shared with you, huh?" Madeline smirked. "Is she a succulent kisser?"

Dan hesitated, noting how Madeline had unfastened one more button between her breasts, exposing her swollen areolas. His hand felt along the matching swell of her waistband, causing him to shudder with anticipation.

"Hold up, who's better?" Madeline hissed, her lips finding his once more, her tongue slithering across his jawline and up to his ear.

"I don't know," Dan mumbled, feeling like he'd never experienced anything quite like this before. He wasn't sure what to say.

"It's alright if she is. You're only the second person I've kissed, so I need a lot of practice," Dan briefly contemplated whether Madeline had left a boyfriend behind when she moved to their town, when she whispered into his ear. "Mr. Scanlin was my first. He's been teaching me how to kiss and more. He says I'm a quick learner, but I need a lot more practice."

Dan's heart skipped a beat. He could feel the blood rush to his cock. He was concerned that Madeline might've slept with Frank Scanlin, the man who, eighteen years ago, had seduced his mother in a week and had her pregnant within the year. Dan felt Madeline's lips against his again. Her hand guided his hand to her hip, then pushed it inside her panties. He couldn't help but notice how Madeline's pussy was different from his mother's. The soft hair on her pussy lips, the lack of flabby, sagging lips compared to his mother's mines, and it felt much tighter. She moaned into his mouth when she felt his fingers glide through the short curls of her pubic hair. Dan hesitated beforeMadeline pushed his wrist down until his fingers were cupping her sex. He could feel the torrent of sensations that rolled over his brain as his fingers inched up her slit, grazing her clit, causing her to moan into his mouth. Dan's body tensed up as an involuntary moan escaped his lips. He felt his balls explode as he ejaculated in his pants. He forced himself to remove his hand from her panties and slumped back against the sofa, both astonished and mortified at his reaction.

"Oh god, Madeline. I'm sorry!" he stammered, trying to maintain his composure.

Madeline giggled as she pressed his now flaccid cock. "SURE." He could see that she was rubbing herself through her panties beneath her dress. Dan's mind flashed back to the memory of his eighteenth birthday when he had spied on his mom as she played with her pussy and fantasized about what her life must've been like with Frank Scanlin. This was different. Madeline was a girl his age, this was real, and the fact that she was now standing in front of him - so bold because of her time with Frank - terrified him. He needed to ask her to be his girlfriend, but the thought of her declining terrified him. He cleared his throat, taking a deep breath.

"M-Madeline? It's probably a crazy time to ask, but would you be my girlfriend?" he asked, trying to sound confident.

To his delight, Madeline beamed a radiant smile. "I was just wondering when you'd ask, Dan Boykin. Yes, I'll be your girlfriend," she said.

He couldn't believe he'd just asked her, but relief rushed through him. "There's just one condition," she continued.

"What's that?"

"You'll let me continue talking to Mr. Scanlin."

Dan felt slightly apprehensive but persuaded by Frank's words. "I want you to keep talking to Mr. Scanlin. I want him to keep teaching you stuff."

"I knew you'd say that." Madeline leaned in to kiss him before pulling away. "Now go clean up. I don't want to go home with my underwear soaked with cum."

Dan went to the bathroom, showered off, and took clean underwear from his drawer. As he exited the bathroom, Madeline was waiting for him, still wearing her skimpy sundress, her tits practically out of the dress now. "My school clothes are upstairs, but I don't want to bother them."

"I can go get your clothes." Dan offered, unsure of the situation.

"No. I don't want to disturb them," she responded. It seemed that they had both chosen to avoid going back upstairs. "I can just wear this home. I'm sure mom won't mind."

They departed, leaving behind some news that Madeline wanted to share. She knitted her fingers into Dan's hands and exclaimed, "Um, you might have forgotten! Mr. Scanlin set up a meeting for my mother. She's attending a job interview tomorrow at his friend's place. It looks promising, with regular hours from 9 to 5. Isn't that amazing?"

Dan's smile was warm, "Yeah, that's fantastic news! I think she'll nail it."

Their hands remained intertwined as they journeyed to Madeline's apartment. Before parting ways, she encircled her arms around Dan's neck, transferring a passionate kiss to him. The kiss continued until she pulled away, beaming at him. "Goodbye, my love." She whispered and sprinted to her door.

After a few minutes, Dan settled down in his room, his laptop open and focused on erotic content. A stiff arousal was throbbing to his rhythm. He was in a relationship! This moment of elation obscured the discomfort of hearing Madeline confess that she and Frank had shared a passionate kiss. She had also mentioned that he would teach her more, getting rid of Dan's discomfort. He gazed at the computer screen and visualized Madeline on her knees, Frank forcefully attempting to enter her tiny vagina. He shivered in discomfort and with a moan, he emitted his limited sperm.

The following day, Madeline sounded cheerful, "My mother was still awake when I returned late at night. She adored the dress, and I can't wait to start looking great! She phoned your mother yesterday and thanked her for the gift. She said she would see her today to accompany me shopping. Mom protested, but your mother was determined."

Their conversation flowed without a hitch and they ended their call. Dan took a shower, discovering a note from his mother explaining that she and Madeline were on a shopping spree. Madeline was absent that weekend, but they communicated via text. She revealed that his mother had gifted her a fresh set of outfits for school and soccer nights with Frank. She also mentioned that her other ones were intended specifically for her dates with Frank Scanlin, which Dan would have to wait to see.

On Monday morning, Dan hugged Madeline in one of their usual spots at the school entrance. He was perplexed by the visibly different look she showed off. She had a sleeveless, tight shirt ending just above her waist, paired with a short skirt, a denim jacket, and Doc Martens. Her makeup looked more enhanced than usual; her eyes were accentuated, and her lips were seductively shiny. He asked her, "Do you like your new outfit?"

She flashed him a wide grin, "It's good that my nipples aren't too exposed. I was considering going without the jacket but thought better of it. What do you think?"

Dan was shocked, so he queried, "What do you mean?"

She glanced around, making sure no one was paying attention, and undid her jacket, disclosing a glimpse of her nipples on her choice of lingerie. She tossed her jacket back on and locked eyes with Dan. "Alright, I'll show you more when we're alone."

During their drive, Madeline unbuttoned her jacket. She exposed her nipples to Dan multiple times. Once they arrived at Dan's home, she kept the jacket off, allowing her top's transparency to show through. Her mother, Sheila, warmly welcomed them and they hugged.

"I approve of your lovely, curvaceous silhouette in that sleeveless, tight shirt and short skirt!" Sheila smirked. "Your breasts have developed quite nicely and are much larger than mine when I was your age. Impressive, Dan!"

Madeline chuckled, "I did keep my vest on at school, but on the way home I thought Dan was going to get a neck injury the way he was looking over at me!"

Sheila and Madeline giggled as Dan turned red. He trailed after them into the house, and shortly thereafter they were working side by side on their assignments. Once they'd finished, they shifted onto the sofa and started kissing. Madeline led Dan's hand to her breasts, letting him feel them through her thin shirt. After a few minutes, she brought her hand up his leg to his crotch.

"I never thought I'd enjoy dressing sexy like this, but it's fun," she informed him while fondling his erection. "I like how you check me out. And how I get you horny."

Dan struggled to keep his focus on the sensation of Madeline's firm nipple against his palm instead of the sensations coursing through his crotch. "Do you like Frank checking you out, too? I mean, he's teaching you what turns me on. He gets hard just like you, only his cock seems enormous."

"Yep, I do. Isn't that okay? He's helping me learn what turns you on. He has a large member just like you, it's just very pronounced."

"Have you ever... touched him there?" Dan gulped, imagining Madeline's small hand on Frank's massive penis.

"Yeah, I did. Through his pants. It feels warm, throbbing, and it's so much bigger than yours." Madeline slid her hand up Dan's leg to his groin, using her free hand to caress his erection. "After we kiss for a while, and he rubs my clit, his cock reaches that far down his leg!"

Dan gasped, contemplating Madeline's detailed account of her making out with Frank. "Have you cum while you two... you know, kissed?"

"Uh-huh," Madeline continued unabashedly, guiding Dan's hand between her thighs. "Mr. Scanlin said he likes how wet I get when I'm turned on. And he knows how not to make me cum. He's really good at it. He makes me cum fast."

For a few minutes, Dan traced his fingertips over Madeline's soaked panties while they kissed. When she moved his hand under her skirt and onto her exposed pussy, he felt her moist slit. She spread her legs further, then demonstrated how to transfer her juices from her pussy to her clit by stroking his finger between her opening and clitoris.

"Hmm, that's the spot. Keep moving your finger down to make it wet, then back to my clit," she instructed him, eyes closed and barely containing a smile. "Do you feel how wet I am? Mr. Scanlin makes me even wetter, but he's much more experienced. Kiss me, Dan. I'm about to cum for you."

Dan turned his head and they kissed more passionately, his hand sliding in a circle near her clit as he stroked her. Her thighs quivered and she gasped at a sudden climax, then shifted her hips so he could reach her breast with the same hand. He toggled her hard nipple until she moaned, and soon he was unable to contain himself. He moaned as he ejaculated in his underwear.

The two of them repeated their rendezvous a couple of times throughout the week. It was a bit troubling for Dan to cum in his pants, but Madeline seemed to enjoy it, so he didn't mind. He was developing a fascination with her damp snatch, even though he'd yet to see it. He felt a deep pride in making her cum. She reciprocated by encouraging him to explore her body, even showing him how to fondle her breasts.

When Thursday came around, Dan and Madeline were slightly uneasy about the evening ahead. Sheila had invited Mr. Scanlin to join them for dinner. Dan couldn't help but feel a slight fear that he'd have to sit through an intimate conversation without objection. Rhonda sent them upstairs once dinner was over, while Dan retreated to the game room and Frank to his study. An hour later, Madeline made an appearance in the game room, adorned in a short, black nightgown with a matching lace thong. The nightie was a couple of inches below her ass, leaving her behind completely visible. As soon as she sat on the sofa next to Dan, she threw her arms around his neck and kissed him, her legs spread wide.

"Mr. Scanlin loved this outfit," she murmured coyly. "And my pussy got so wet reminiscing about him. I'm sure yours is too."

Dan's eyes widened when he studied her sodden lace thong, his palm tracing the wet material. "Oh my god, Madeline, you are incredibly wet."

Madeline sat back and smiled. "Mr. Scanlin found me very sexy in this. What do you think? Is it enticing?"

Dan's free hand reached up to fondle her naked breasts while he worked his palm over her sodden panties, absorbing the moisture. "I think it's very seductive."

Madeline stood and opened his pants to remove the sodden underwear, then slid back onto the sofa as if to advertise her own soaked panties. "Maybe you can kiss me with it on this time."

"I recognize that I can't stop it." She murmured softly as she kissed his neck and ear. "He's aware of how to touch me to get me soaking wet. One more reason I'm so damp is that he informed me tomorrow he's going to allow me to take his manhood out and play with it!"

Dan groaned upon hearing his girlfriend discuss playing with Frank Scanlin's large penis. Her vagina was so wet that when Dan inserted his hand into her panties his fingers were instantly slick with her fluid. He swiftly found her clitoris, though when he rubbed it she flinched and put her hand on his, stopping him.

"We don't have much time until I have to go home." She informed him. "Mr. Scanlin made me cum a lot this evening, so I'm already highly sensitive. I will make you cum, though."

She found his hard lenis through his trousers and rubbed it.

"You like knowing Mr. Scanlin doesn't hold back getting me so drenched, don't you?" She asked while gripping his cock.

"Yes, I do." Dan gritted his teeth as he was on the verge of coming already.

"Are you thinking about me touching his bare penis tomorrow? It will be the first penis I ever touch. Do you want him to show me how to give a blowjob as well?"

"Mhmm," Dan's hand inside her panties was barely moving, his finger sliding over her damp vagina lips. He continuously envisioned his mother choking on Frank Scanlin's thick penis, wondering how long it would be before his girlfriend was swallowing the older man's gunk.

"I'm happy. I'm extremely eager to taste his come." She chuckled and moved her other hand between Dan's legs, feeling for his testicles through his trousers. "I'm certain Mr. Scanlin will provide me with a lot more to taste than you!"

Dan groaned and released, his thoughts racing because of the thought of Madeline tasting Frank's sperm before even seeing his small cock. She turned on the bathroom and switched her garments, where Sheila had delivered her school outfit. Once Dan cleaned up and dressed, he took her home. They chatted about school, and Dan recalled that their Senior Prom was only a few weeks away. He stopped near her apartment and switched towards her for a moment. They were holding hands, and as he turned he saw her acquire a doubtful gaze upon her face.

"You understand I'm not very skilled at stuff like this, so if I do it wrong I'm sorry." He turned his shoulders and grabbed her other hand, holding them both. "Madeline, will you go to Senior Prom with me?"

Madeline's face transitioned from apprehensive to cheerful in an instant. "Oh my gosh! Yes, Dan, of course I will! Oh, you silly person, you had me terrified. I thought you were disturbed about my arrangements with Mr. Scanlin tonight."

Dan sighed in comfort, understanding that he created Madeline happy. He was so thrilled that he couldn't conceal but exclaim, "I'm not upset in any way regarding tonight. I can't wait to hear what you and Frank get up to."

"MMMM, hearing you state that excites me. I'll be damp all day tomorrow pondering it." She leaned over and they shared a number of kisses. Following, he took her to her apartment. Prior to entering, she leaned into Dan's ear and murmured, "I want you contemplating me handling Mr. Scanlin's penis when you rub your penis tonight." Dan shivered and could really only nod since he realized that was what he'd be doing.

Throughout the entire day at school on Friday, Dan had trouble focusing due to the things that were going to occur in his residence that evening. At lunch, Dan shared about the prom to his friends, as well as Madeline saying the singles should attend even if they didn't have anyone to accompany them. The three seniors, Trevor, Nate, and Zander, replied they would think about it. Madeline stated there were typically groups of unattached girls at proms that would be more than satisfied to dance with the boys as a group. However, they still sounded hesitant but did not say "no."

Madeline told Dan various times during the day that she was a mix of fearful and excited about seeing her first penis later, conveying that her vagina was currently overflowing. When they got to his house after school, they spent some time kissing, but she wouldn't let him touch her below the waist since she desired to delay until Mr. Scanlin. As soon as supper was over, she and Sheila hurried upstairs. After Richard left, Frank glanced over at Dan, who was already starting to clear the dishes.

"You're an excellent male, willing to let your girlfriend spend time with me, Dan." Frank asserted as he walked towards the living room, stopping at the doorway. "I understand you're taking her to prom. I believe it's a stellar idea if I spend somewhat more time with her for the following few Fridays to ascertain she is prepared for you. Are you okay?"

As Dan tried to digest Frank's words, his heart was racing with questions. How long would he be spending with Madeline? Most prom couples ended up getting their own rooms after the event. Would Madeline's mother allow it? Fear gripped him as he turned toward Frank and looked him in the eye before glancing down. "No sir, I won't mind if you think she needs more time with you."

"Excellent," Frank nodded, headed towards the living room.

Not long after, Dan was in his game room when his mother entered. She told him, "I've put Madeline's clothes in the bathroom." She passed by the sofa and sat next to him, wearing a sheer blue gown that barely concealed her nether region. Her panties had the same sheer quality, revealing her bald pussy which bulged against the thin material. She reached out and stroked his cheek, grinning at him as he sat stiffly. She knew how nervous he was and that he secretly desired this scenario.

"It's okay, Dan, Frank isn't forcing Madeline into anything she doesn't want. I've spoken to her about everything. What worries her the most is disappointing you. She cares deeply for you and wants you to be happy. I hope you're reassuring her that you're in support of what she's doing. You want her to continue meeting with Frank, right?"

Dan's mind was bustling with ideas. His cock was throbbing as he gazed at his mother's outfit, which showcased every inch of her body. He was fixated on her pierced nipples and the damp spot in the crotch of her panties. He wondered what Madeline was wearing – was she playing with Frank's cock already? The thought was almost enough to make him moan out loud. He glanced at his mother, gulping out, "I do want her to keep seeing Mr. Scanlin. I don't think we'd have made this much progress without him guiding her."

"It's admirable of you," she smiled at him. "Would you like me to talk to Madeline's mother about you two having a room after the prom?"

Dan nodded, "That would be great, mom. I hadn't even considered it."

"I'm sure Donna will be fine with it. She knows how much you like Madeline. Now, how would you like to practice some kissing?"

Dan's eyes lit up as his mother scooted closer on the sofa, tossing aside her top to leave her only in her sheer panties. They made out, Dan running his hands all over his mother's small body. He entered her panties and found a significant contrast between his mom's and Madeline's. His mom's pussy was completely hairless and her lips were loose and floppy, making it easy to slide his finger inside. On the other hand, Madeline's pussy was adorned with a fine bush of soft hair, and her lips tightly pressed together, making him have to part them to reach her clit. After a while, she moved away and kissed his cheek, pulling her hand out of her panties. His finger was coated with her juices.

"You're pretty good at finding your way around a pussy," Shelia smiled at him. "Is Madeline giving you specific directions on how to touch her?"

"Yes, she's telling me what Mr. Scanlin does to her, and I'm trying to emulate it," Dan said. "She says Mr. Scanlin is better at making her cum, but I'm starting to get better at it."

"That's great," Shelia concludes, standing up and making her way towards Madeline and Frank's room. "I'm going to check on them. Frank will probably be sending Madeline over to you soon."

Just about half an hour later, Madeline entered the game room. Dan had been staring at his phone but his gaze locked onto her as she walked in. She was wearing a sheer blue teddy with straps that ran down underneath her breasts. The top had an exceptionally long V cut-out, exposing most of her beautiful tits. The crotch of her panties was pushed out, uncovering one of her pretty pussy lips. As she got closer, he could see that she had mascara running down her face, her cheeks were flushed a deeper shade, and her eyes sparkled bright. She had tears of joy in her eyes and her lips curved into a wide grin.

"Are you okay, Madeline?" Nervously, he asked, watching the evidence of Frank's cum dripping down her face, chin, neck, and the slopes of her breasts. "Frank cums a lot," Madeline chuckled.

“I'm good!" she giggles.

She sat next to him and absent-mindedly traced her finger along her chin, wiping off a glob of cum that was about to drip. As Dan observed, she opened her mouth and sucked her finger clean.

"Cum tastes good. Next time, I'm aiming to catch it all in my mouth. I didn't expect it to blow out like that." She chucked, then moved on to unbuttoning Dan's trousers and underwear, sliding them down.

"Oh man." Dan moaned as he felt his girlfriend's hand on his member for the first time. He looked down to find that her hand only just managed to cover all but the tip of his shaft.

"I can even wholly encompass Mr. Scanlin's cock with both of my hands," she stated, squeezing his slender penis, "and my fingers can't even get a full grip on him, either. Do you like when I compare your member to Mr. Scanlin's? I can tell by your state that it's a solid YES, she said with a mischievous smirk. Do you want to hear what occurred tonight, Dan?"

Dan nodding, almost daring not to speak out of pure excitement.

"Mr. Scanlin was quite taken with my attire. It didn't take him long to unfasten the crotch area in order to finger my pussy. I was so frisky, I'm guessing I achieved my first climax in less than a minute. He took his pants and underwear off, and I had my first glimpse at a genuine penis in person. I was already aware it was sizable through touch, but it seemed enormous! We locked lips for an extended period of time. His digits were all over me, pulling down my top to expose my breasts, then teasing my pussy at the very same time. I was stimulating his colossal dick simultaneously. It felt incredible, warm and hard, its tip frequently dripping precum. Following some time, he had me lay my head on his muscled belly so that I could get a close-up look at his equipment. He showed me how to handle it and how to caress his scrotum without hurting them. His balls are massive!"

Madeline's head laid on Dan's hairless stomach, and she descended her hand to his testicles. Dan could feel the former state of cum slathered onto her cheek against his abdomen.

"There were three or perhaps four climaxes while we were engaging each other. His furry stomach tickled my cheek. After a while, he had me lie my head on his torso and fondle his balls while he thrusted his finger in and out of my vagina. I could hear it slurping as I was that wet. Frank proceeded to massage my anus. That felt odd yet pleasurable, but I was highly anxious."

Dan was experiencing an elevated sense of arousal as he watched Madeline pivot and lower her head over his erect penis. She peered into his eyes and licked her lips. He could feel her warm makeup-smudged breath on his erection.

"Mr. Scanlin instructed me to suck his cock if I wanted." Her eyes sparkled with mischief. "I didn't hesitate. His phallus truly filled my mouth, causing my eyes to well-up from the stretch. He stated I performed admirably for my initial vocation as an oral feminist, even though I could hardly accommodate his head and a few inches. He sounded certain I would quickly learn how to deepthroat him."

Madeline began pumping his shaft with her fingers before licking lightning-fast along the underside to pull out some extra precum, depositing this on her tongue.

"Mmm, your precum is delicious, too!" she teasingly teased him, stroking his cock steadily. "Are you OK with your girlfriend confessing to liking the taste of your sperm and craving a strokeable massif cock to splatter all over her?"

"Oh God... Madeline!" Dan had never been turned on this much by this type of chattiness from his girlfriend. He could also visualize his Madeline wrapped around Frank, her head cupped into his lap as she wiped her tearful eyes. The wickedness gleaming from her face now resonated in his mind. Her forehead and cheeks glistened with the maturing cum of Frank Scanlin, yet she indicated that she's going to follow suit with Frank.

"Mr. Scanlin mentioned that it took your mother an entire month to learn to deepthroat his manhood. I'm going to try to do it sooner. I want to take in all of his expansive penis. You can't possibly compare your miniature member to his."

He pressed his pelvis against her clenched fist, his face still positioned over his erect cock. When his climax struck, Dan's eyes shut in pure pleasure. The feeling of his girlfriend's tight grip on his member as he came was unique and surpassed any other experience he had had. He felt the three pulsating bursts within him, and as he settled back into the cushion, he reopened his eyelids to find Madeline admiring his now diminished penis.

"I guess that's what I had to ask about," she said, sporting a flirtatious grin. "It was much more different compared to Mr. Scanlin's experience. I had it in my mouth when he ejaculated, and the force with which his semen sprayed over my face and breasts was astounding. It physically startled me, that's how strong it was. His produce was thicker but not as sweet as yours, though I admire them both."

She lifted her palm to her lips before returning it to her mouth, licking away the traces of Dan's seed.

"I guess I'm something of a cum expert, huh? Mr. Scanlin's was powerful and intense, whereas yours was more gentle. They all taste good."

After an unfinished sentence, Madeline leaned in toward Dan. Perceiving her past activities with Mr. Scanlin, he was reluctant to reciprocate. Then he remembered his mother's advice to be considerate; so, instead of mournfully turning his face away, he reluctantly returned her kiss. He felt the sticky remnants of her lips, reminiscent of the taste of bleach on his tongue, but the sound of her moans silenced his reluctances. They continued their embrace for a while, and she eventually sat up to leave for the bathroom.

"I'll need to clean up before returning home." She bared a playful smile and touched his cheek before sauntering towards the restroom.

Dan's gaze followed her, resting on the visible thong of her teddy, leaving her firm rear exposed. He closed his eyes and pondered over thoughts, picturing Mr. Scanlin indulging in Madeline's sexuality. Although she had first kissed Frank and allowed him to pleasure her, would there be more activities before him?

Minutes later, Madeline emerged from the bathroom, dressed in casual attire as she had been that day. She had taken a bottle of water from the refrigerator and carried two glasses. She set one down before Dan and took a long sip.

"You would be astonished at how parched I get after performing such duties." She grinned, noticing Dan's partially untouched glass.

"I'll instruct mother to leave a pitcher of water in the refrigerator for you."

"I don't need to return home for another hour. Are you in need of assistance in setting up the table for D&D?" Dan complied, unable to detach his mind from his current emotional state.

He fetched the D&D supplies from the shelf, and they prepared the dice, maps, and notepads. Madeline's idea appealed to him, but part of him dreaded the boys' reactions.

His girlfriend sketched her idea with added enthusiasm, describing her campaign and even soliciting his mother for assistance in constructing her "cave." He found her suggestions to be delightful, and when he voiced his approval, she became thrilled, bestowing him with a hug. They discussed the preliminary details. Although it was simple, he acknowledged her efforts.

"I grant you my approval. I will tell the guys on the morrow that we will have a short side campaign beginning in a week." Dan's affection intensified. Less than an hour ago, she had been attired provocatively, exuding eroticism before Frank, who had forced his way into her mouth and pushed his fingers into her, both in an intensely sexual manner, leading to his release. Yet now, his girlfriend was talking to him just as she had in high school, concerned with organizing their friends' D&D game.

He clasped his arms around her, heartfelt words escaping his lips. "I love you, Madeline."

Caught off guard by the sentiment, Madeline embraced Dan, their lips locking sensually. "I love you, too, Dan. I was afraid you would believe I was slutty enough to be your girlfriend."

He held her tighter, whispering, "I cherish your advances, and I'm thankful you allow guidance from Mr. Scanlin." He recalled his mother begging him to consider her remarks and offered her a kiss.

The prom event was three weeks away. In the middle of their D&D game session, Madeline inquired if they had intentions to attend and the boys responded in the negative, claiming they wouldn't blend, and no one would dance with them. She assured them that she would at least dance one slow number with the one who visited, and they should not skip their senior celebration. Dan encouraged them by revealing that Madeline devised a side campaign for the upcoming two Saturdays with the intention to assist them to comfortably attend the prom. The enthusiasts were hesitant but couldn't resist the chance of a new game. They hesitated, but as usual, they chose to get involved. As they departed, Madeline gifted them with their costumes and a character sheet for the following two Saturdays.

One Sunday, Sheila and Donna accompanied Madeline to purchase a gown, while Richard took Dan to get a tux. Maddie continued to visit Dan after school. Dan had yet to fully witness Maddie's nakedness, though she allowed him to explore it. He couldn't fathom her vagina's intense heat, strength, and wetness. She even allowed him to penetrate it. She clarified that Mr. Scanlin gave her workout methods, including kegels to maintain her vagina's tightness. Not only did she perform oral sex on his manhood but also gave him hand-jobs, although she occasionally played with his testicles. This resulted in Dan frequenting her twice each week, and each Friday, though he could not last long, he ____ because Maddie was preoccupied with Frank for around two hours every week, and her lustiness engrossed in Frank's organ resulted in terrible jaw pain.

On the following Saturday, Dan picked up Maddie early, and they commenced creating a setup for their friends to partake in their D&D's campaign. Trevor, Nate, and Zander acceded to participate. They had never come in costumes, but each brought their nerf weapons they knew about from when they were young. Their weapons provided the look of actual arms, with slivers of black and silver to signify the edge, and brown for wood and leather to show wear and tear. Dan's nerf bow and arrows would participate for Maddie, who hinted that she would employ them against their foes. They entered the game area, adorned in their costumes, glancing around in anticipation. Trevor had a battle ax, Nate a bastard sword, and Zander a curved scimitar. Dan selected a round shield and a gladius.

The 'cave' was established in the spacious room adjaccent to Daniel's bedroom. Instead of a bed, they formed a wide space on the floor. They used several big bean bags covered in dark sheets to appear like boulders when positioned and organized a nest on the futon. Two smoke machines and some affordable multicolor LED lamps created a creepy ambiance. The room's door was left ajar, covering the doorway with a black cloth. The boys were all gathered in the game room at midday while eagerly awaiting Maddie's arrival. Trevor excelled in handheld fighting instruments, Nate wielded a long sword, and Zander donned a curved sword suitable for sports, while Daniel held a shield and a sword. A guilty smile lit Maddie's thoughts as she entered the room, and it seemed her confidence had increased in the last few months. She removed her coat, revealing her outfit underneath, which included a long, black leather cloak reaching the ground. Her long, loose braid fell down her back, yet they could only view her thighs owing to the skirt covering the boots she wore on her feet. She carried her makeshift bow and had an arrow quiver on her shoulder, concealed beneath the cloak. She boldly walked to the room's center, clutched the cloak off her shoulders, and revealed her lewd dress in one swift motion. The boys gawked as sketches don't display details, and Madeline exuded an exceptional level of confidence.

Madeline instructed us to kill the succubus that inhabited a secluded cave. Eager to accept the townspeople's request, we gathered in the hall, waiting for the task at hand. Sheila, the sexually enticing seductress, noticed our gaze drifting toward her as she drastically posed, showcasing her appealing physique.

Dan's attention quickly shifted from his adoring girlfriend to the captivating image of his friends. They stood, dumbfounded, until Trevor decided to take action.

"I'm fearless. Take me to the cave, Madeline!" Trevor declared, eliciting approval from his friends.

With a wave of her hand, the madam directed Trevor to the dark hallway leading to the cryptic grotto. As the ax-wielding adventurer moved deeper into the cavernous chamber, we lingered behind, watching the scene unfold from a safe, yet eager distance.

Upon entering the gloomy chamber, Trevor's vision readjusted to the fainter illumination. In this eerie setting, lifeless forms huddled on various makeshift beds. A few armatures littered the ground, serving as warnings of prior struggles. Finally, he beheld the form of Dan's mother: Sheila. With the grace of a mystical enchantress, she lounged atop an abundant pillow mound, nearly dressed from head to toe in glittering adornments.

"You're under the influence of a love potion," Madeline advised Trevor. "Anything you do for the next 15 minutes will be solely for the entity before you."

The bewitched knight mulled over the prophetic statement, regarding his mother's undoubtedly impure intentions as consuming their passion. Fueled by an irresistible swell of affection, Sheila approached him. The rest of us found it impossible to avert our eyes as we swooned over the illicit act.

Her hand snaked across the fluid motion from Trevor's shoulder to his back, unity drawing them even closer together. Gripped by the hypnotic state, Trevor's body slumped gracefully into position. Overwhelmed with a desire to experience this ultimatum, Sheila, the demoness, gently nuzzled her face toward his ear.

"I'm not your mum, merely a succubus," she declared in a breathtakingly sensual tone. "Open your mouth. I'm about to show you how a woman kisses her lover." For the first time, he felt the soft, sultry miasma of a woman's lips envelop his. Her tongue snaked past his lips, tasting his terror and vulnerability. Certifying his dreamland existence, she caressed his body as her menacing persona desperately tried to enslave her victims.

"I'm exhibiting a bit more of my nasty side," she whispered, falsely disguising her indecent intentions. Releasing her grip on him, Sheila's ravenous scream pierced the silence, bidding him an abrupt farewell.

Nate, Zander, and Dan, faced with the enticing lure of their own seductress, could not escape her allure. Each boy explored her naked form as she affectionately taunted our insatiable lusts. Immediately dazed but enraptured, we returned to the game room, drowned in the lustful thoughts of her vulnerable gardens.

"To obtain our award, we must vanquish the succubus," Madeline ordered. "Dan and I will team up and take her on." We followed her directives, anticipating the arrival of an ardent showdown.

As Dan and Madeline swept past the corridor, their sturdy figures appeared in view. Our expectations were far more innocent. We watched through the gap between the shower curtains. Sheila reclined naked on a bed of pillows, revealing her true sinister intent.

"The sheer passion of watching you grope those innocent young men stirs my loins!" she uttered. Peering at her face, Madeline grinned diabolically. "Who does that long-stemmed phallus belong to?"

Dan's jaw dropped in disbelief. "Zander?"

"Precisely," she taunted, elevating her hips provocatively. "Beg the succubus to let you taste his delectable essence." Unsettled, Dan squatted, grasping the metallic bar directly above the tableau.

Fervour set the stage as chaos ensued. Dan and Madeline walked into the crimson-tinged chamber, but Sheila's rampancy consumed her appetite for seduction. Flourishing her undressing, she caught sight of Dan and Madeline's captivated gazes. Waving her arms to disrobe further, she excitedly called off for Dan to replace his usual weapon with something more akin to a toy for her to mimic.

"I'm not your mum, but a twisted creature lurking in this abyss. If you want to win, we'll need to unite our strength ... Pity you've lost your sword." She pushed Dan to defend himself.

Total silence crept upon the scene. They found themselves alone with the succubus. Sheila had an imperious, enchanted hold over all the males. They discovered that the encountering of each cast a rich, satisfying, tangy experience which was distinctively enlightening.

Madeline agreed, "Yes, you're correct." Meanwhile, she retrieved a bag concealed behind the futon.

After approximately five minutes, Dan resembled someone who had been physically abused. His face was painted to resemble bruises and cuts, his shirt was ripped in several pieces, and a phony blood-stained wound was caused on his forearm. Alone, he returned to the game room, demonstrating signs of severe intoxication.

"The succubus has taken Muriel!" He yelled, falling onto the couch as the other three players approached. "She placed a spell over us both, bound Muriel, and battered me unconscious before forcing me out of the cave. We require medical attention in town then we must rescue Muriel!"

After a moment of dramatic pause, Dan stood up. "Okay, that's it for now. We'll resolve this next Saturday. Guys, make sure to buy your prom tickets before the big event, or else Madeline might be upset."

Once the players departed, Dan headed back into the cave to turn off the smoke machine. Discussing possible modifications to the storyline, Madeline and Sheila remained seated on the futon. As he observed, he noticed that his mother was dressed in an open gown, her pierced nipples and bald pussy were exposed. Although Madeline didn't openly gawk at Sheila's body, she occasionally glanced at it.

"Madeline has been sharing her plans for next time with me. Are you satisfied?" Sheila questioned Dan.

"Yeah, definitely." He looked toward Madeline. "Has anything changed since we discussed it?"

"Partially. I believe adding some blemishes to my looks would seem more authentic. Also, I'll endeavor to prevent the succubus from siphoning my life essence. I've thought about something enjoyable to tease our friends with as well!" She announced. "You're certain that you'll like the alterations we've proposed?"

"If you assure me so." Dan had to accept that his friends' reactions to Madeline's revealing outfit caused him sexual excitement. He pondered what additional surprises she may have planned.

The following week paralleled the previous one, apart from Madeline instructing Dan to abstain from ejaculation until their next D&D weekend meet. He was already on edge when Madeline entered the game room on Friday evening after her session with Frank. He couldn't help feeling his erection spike at the sight of her. She was dressed in a tight white tank top that barely concealed her ample chest and donning only a white cotton thong. Her eyes appeared glossy, and her lips were slightly enlarged due to stretching over Frank's giant penis.

"Frank got you exceptionally aroused tonight, didn't he?" Dan asked, admiring Madeline's body from top to bottom. "By the way, your crotch appears quite damp. Did you discover a delectable treat earlier?"

Silently, she replied, "Frank always makes me wet." Then she ran her hand along her belly, displaying her still damp panties and the stringy cum-covered material that had adhered to them. "Would you like me to tell you about Frank's cruel adventures with me?"

"I'd be honored," Dan responded, gazing at her wet fingertips before returning his attention to her genitals.

"After I performed oral sex on him for up to an hour, I was instructed to remove my panties while standing. With my hand on my clit, he released his seed." She then narrated how she rubbed her fingers into Frank's sperm, becoming sexually aroused.

Her lusty speech had a significant impact on Dan's libido. He anticipated seeing her wet panties and the cum smeared on her hand. Yet, he desired to witness her actual pussy rather than her thong. He wished for her to share her private parts with him.

However, she merely displayed one of her gloved and cum-coated fingers, ensuring Dan could detect the musty odor of her corrupted pussy. Then she licked off the cum from her digits as she grinned.

"Can you detect the strong aroma of my pussy, Dan?" She proclaimed before sharing, "I've promised Mr. Scanlin that I'll withhold my climax until prom night, but you may have my oral favors tomorrow if you've been a good boy this week."

In this story, Dan didn't protest when Madeline perched on his lap and kissed him using her filthy mouth. His libido was so high that he feared he was about to climax from just the sensation of her bare backside against his covered penis, yet he somehow managed to restrain himself. Some time later, she had traded her school outfit for her skirt and top, and as they pulled up outside of her apartment, she elevated her skirt to reveal that she was still wearing her cum-soaked underwear.

She told Dan, "I'll see you tomorrow! You'll be picking me up at nine so we can prepare for D&D, right?" They embraced outside of her apartment.

"Yes. I'll be there. I adore you."

"I love you as well!" She grinned, planting a kiss on his cheek prior to disappearing inside.

Following an afternoon of setting up the smoke machine and including a narrow table in the cavern, Dan was dispatched away to let Madeline and Sheila conclude their preparations. Madeline had inscribed his lines for him, and instructed him to begin at precisely 12:15 PM. While he waited in the game room, wearing his ensemble consisting of a bloodied sleeve and various dried blood, the gentlemen arrived. They were excited for another opportunity to possibly more than kiss Dan's practically naked mom. The group discussed the previous episode, and Dan informed them that he had heard what had transpired in the cave. Dan explained that as long as they didn't disclose anything to anyone outside of the group, Madeline and Sheila intended to provide an even more fulfilling experience. They zealously agreed, vowing that nobody would learn about the events in the cave.

At the designated 12:15 PM, Dan commenced his narrative: "Gentlemen, the succubus has taken our comrade, Muriel. Tonight is the full moon, and if we don't rescue her before sunrise tomorrow, she will perish. I spent the final bit of our gold purchasing potions to safeguard us from succumbing to the succubus's influence once more. In addition, I found a scroll that illustrates how to break the spell that mutated an innocent woman into that detestable creature."

Dan distributed Caprisun-filled pouches to serve as their potions. He also displayed the scroll. It featured a graphic of a naked woman lying on a bed, with arrows pointing at various regions of her body and guidelines detailing how to break the hex. The three exchanged concerned glances, then placed their hands on the table, nodding to Trevor.

"After we subdue the devil, use this potion to safeguard yourself from the succulent liquid emitted by the demon," Dan handed Trevor a jar boasting Arabic-looking text.

After that, the trio advanced toward the cave. The spooky music was playing, but they could also hear inaudible moans emanating from inside. They promptly entered the room and dispersed, with Dan in the center and Trevor behind him. Nate and Zach flanked Dan.

"Holy moly!" Zach exclaimed upon gazing at what lay ahead.

The table Dan had arranged was covered in a dark red blanket. On it lay Madeline. Ropes bound her wrists, with a chain affixed to them overhead, keeping her arms tightly taut. Her buttocks were perched at the edge of the table, and her boots had been discarded, with ropes around her ankles fixed to the table legs, forcing her legs to spread apart. Her corset's upper three fasteners had been undone, leaving most of her breasts uncovered. She still wore her skirt, and Sheila's head was hidden beneath it. From the sounds emerging from the ball gag in Madeline's mouth, it appeared that Sheila was vigorously licking Madeline's pussy.

Sheila was completely naked, her body smeared in gold and green paint, a long tail extending from her buttocks. Sheila didn't seem to notice the quartet's entrance, although Madeline had, as she displayed a painful expression on her face as she moaned and attempted to utter words simultaneously.

"Capture the succubus! I will help Muriel!" Dan bellowed, recalling the arrangement even as he endeavored not to gape at his naked mom licking his girl's pussy.

Nate and Zach hesitated, then discarded their weapons and advanced toward Sheila. Madeline was thrashing violently, and each of the lads viewed her bosom bobbing on her chest, wherein a small brown nipple emerged as she shifted. Nate and Zach grabbed Sheila's arms, wrapping them together. Then, Zach hurried to catch her kicking legs, grasping her ankles. Sheila now lay stretched out, with her legs touching. Her smooth pussy mound protruded from her groin, and her pierced nipples bobbed as she breathed heavily in their clutches. Instantly, Madeline approached Sheila's hip across from Zach. She snatched one of Sheila's ankles and drew it toward her chest, where her knee pressed against her stomach.

"Come on, Zander! We need to stop her!" Madeline shouted above the music, enjoying how exposed Sheila was in front of her friends. She noticed that with her corset loosened, every movement showed off her bare breasts, and her pussy was just barely hidden under her skirt. She moved back and forth deliberately to give the guys a good view of her perky tits and stiff nipples.

Zander quickly pushed Sheila's other leg against her chest, copying Madeline. Sheila's wet pussy was completely on display now, her wet lips hanging down. They could see the plug embedded in her ass with its tail sticking out. Trevor knelt between her legs and opened the jar of thick, gooey lube.

"Cover her pussy first. That'll help protect you from the acid." Madeline advised. "Then coat your hand."

Trevor dipped his hand into the jar, then started spreading the lube all around Sheila's pussy. When she felt his hand on her tender lips, she moaned and wriggled her hips like she was trying to escape. He quickly coated her crotch, then used his left hand to spread more lube on his right hand. He glanced back at Dan, who was staring over his shoulders, then looked over at Madeline.

"Are you sure?" His hand was inches from Sheila's wet pussy.

"Yes! Do it!" Madeline urged.

Dan watched as his friend inserted his hand into his mom's pussy. Sheila let out a groan when she felt her pussy being spread open. Dan had no idea this was going to happen. Madeline and Sheila must have added it this morning. He knew his mom's pussy was loose, but had no idea it would be able to stretch so much. Trevor had four fingers in her vagina, and as they all watched in amazement, he curled his fingers to fit his thumb inside. Sheila let out a moaning wail and her body shook. Her chest heaved with each breath.

"Feel around for the charm." Madeline instructed as Sheila moaned, her head tossing from side to side.

They saw Trevor's wrist twisting as he felt around in her pussy, then he exclaimed, "I feel something!" He bent his head down in concentration. "I can hardly reach it."

"Push deeper, and when you get it, make a fist around it." Madeline grabbed a handful of lube in her free hand and smeared it on Trevor's wrist and Sheila's stretching pussy lips.

Trevor pushed again, triggering another moan from Sheila. "OK, I have it in my fist."

"Pull back slowly," Madeline started rubbing Sheila's large clit with her slippery hand.

Sheila's pussy lips were stretched so thin that her clit was exposed at the top of her vagina. As soon as Madeline began to rub her clit, she jerked and moaned, "Oh yes! Fuck me, please!" They all watched as Trevor pulled his fist out, Sheila's entire pussy gaping, ready to be filled again. When his fist was partially exposed, lodged in her pussy, Madeline took her hand off Sheila's clit and grabbed Trevor's wrist, stopping his motion.

"Push it back in. Let's make sure there's no other charm deeper." Madeline released Trevor's wrist and resumed rubbing and flicking Sheila's throbbing clit frantically.

Trevor paused with his fist holding Sheila's pussy wide open. He took a deep breath, glancing back at Dan. Dan nodded quickly, and Trevor pushed. Sheila couldn't help but shriek out, "OH God yes! Fill me, please!"

For the next ten minutes, Trevor fisted Sheila's pussy while she humped against him and grunted out her orgasms. Madeline kept rubbing her clit furiously. The other three guys watched, stunned, as Trevor's wrist bone slipped into Sheila's pussy, and when he twisted his fist and pulled it partially out, she begged him to shove it back in as she arched up against his fist. She finally collapsed onto the cushions, and when Trevor pulled his clenched fist completely out of her now wide open pussy, her fat lips stayed parted, revealing her immense opening. Trevor opened his fist and they saw a diamond-shaped gem the size of a large grape in his palm.

Everyone released their hold on Sheila, and after Madeline motioned for them to leave, she covered Sheila with the red sheet from the table. Madeline walked into the game room, where the others waited. Trevor had washed his hands, and the guys were huddled around him.

"It felt wild! It was soft and hot inside. I could feel it pulsing every time I moved." Trevor was saying.

They looked up as Madeline walked over. Her corset was still hanging open, showing off her bared breasts. She went to the fridge and grabbed drinks, knowing she'd give them a glimpse of her bare ass when she bent over. Handing them drinks, she took a seat at the table, ignoring how her corset sagged open.

"That concludes our little side mission." She said.

"Dude, it was so cool!" exclaimed Zander. "Are you and Dan's mom planning on doing another one of those things soon?"

Madeline chuckled, "perhaps, or maybe we'll just let you guys hang out with us without the need for pretending."

Dan was standing behind Madeline, so she couldn't see the surprise on his face. She leaned back in her chair and spread her legs, giving Zander a peek up her skirt.

"For now, though, I need to chat with Dan alone. We're heading to his room. I can hear the shower running, but Mrs. Boykin said she wanted to have a one-on-one chat with each of you before you leave. Trevor, you should go first. Give her about fifteen minutes to get cleaned up." Madeline stood up, holding Dan's hand and they walked across the hall to his room.

After fifteen minutes, Trevor returned to the cave room and found soft jazz playing instead of menacing music. Sheila had washed off the body paint and was wearing a short, see-through black robe. She smiled at Trevor and invited him to sit next to her on the futon.

"I want you to understand how careful you were at the start," she patted his shoulder while looking up at him, "but I think you soon realized how much my pussy likes to be stretched."

Trevor looked down Sheila's open robe and saw her pussy was still open slightly. "Yep, I was a bit worried initially about doing it, but once everything fit, it was fantastic."

"Yes, it was. I haven't had a cum that forceful in a while. And you must need to cum as well, don't you?" She leaned forward and reached for his belt, encouraging him to lift his butt to pull his pants and underwear down.

She pulled him close and they kissed for a while before she lay her head on his lap. Five minutes later, she had swallowed his cum and snuggled against him.

"Not every girl will like swallowing your cum, and many your age will freak out if you tried to fists them. If you take anything from this experience, remember that you don't need to be afraid of girls. Just talk to them and don't be afraid to ask what they like and don't like. Also, swear to secrecy about what takes place in this room."

Trevor swore, at which point Sheila sent him out and instructed him to let Nate in. Nate spent 30 minutes making out with the older woman until he, too, blasted his load into her mouth. When she had Zander on the futon with his pants around his ankles, she let out a contented sigh.

"Holy cow, Zander, your dick is huge!" She shook his cock in her hand, her fingers unable to touch around it. "Ever had a hot, wet pussy on this sexy turkey? You didn't feel a woman's mouth on this big sausage yet?"

"Nope, ma'am," he grunted out, watching as a large bead of pre-cum formed and dripped onto her fingers.

"Well, how about I give you a blow job today, and one day maybe I'll let you screw me? I think Madeline's going to want a taste of this yummy cock, too." Sheila grinned at him, then lowered her head and sucked his cock's head.

Zander watched in awe as Dan's mom stuffed his entire eight-inch, thick member into her throat, humming appreciatively as she positioned her head on his meat stick. Five more minutes passed before he fired a large load of cum into her eager mouth. Sheila emphasized to Nate the importance of keeping this encounter a secret, which Nate agreed to with enthusiasm.

As soon as Dan closed the door to his bedroom, Madeline was pressed against him, kissing him while she pushed his pants down and freed his hard cock. She broke the kiss and sat on the edge of his bed, teasing his cock with her fingers.

"Enjoyed seeing your mom cumming with Trevor's fist in her pussy?" She inquired, feeling her skin against his. "Dan, she was wearing cummy panties from the night before, so your mom got to lick Mr. Scanlin's dried sperm off my pussy."

"Wow, that sounded hot," Dan said, "Did they see your pussy when they were pushing your mom away?"

"I'm almost sure they did. When they pulled your mom away from me, both Nate and Zander were staring right at my crotch. Trevor even took a look." Her fingers were casually rubbing his cock and balls, sending chills throughout his body. "You're okay with that, right?"

"Yep, I understand," Dan agreed, not wanting her to feel guilty. "Did you enjoy the audience?"

"Mhmm. Knowing those guys could see me with my erect nipples and wet pussy turned me on a lot."

"You know, I still haven't seen your private area," Dan shared, caressing her back while rubbing her bottom through her skirt.

"I'll show you after our senior prom next Saturday," she smiled at him. "It'll be worth the wait!"

They exchanged kisses for a while, then Madeline descended to Dan's stomach and licked his member before swallowing it. She sucked on it, later retracting and looked up at Dan.

"I can't help but wonder how massive Zander's cock is," Madeline told Dan as she laced her tongue around his balls. "I adore sucking your dick, but the sensation of Mister Scanlin's hefty one filling my throat is even hotter. I wonder if Zander's cock would fit me perfectly."

"Oh man, Madeline. I'm so close to cumming!" Dan felt his cock spasming, but just before he achieved climax, Madeline halted sucking him and whispered closely into his ear.

"Imagine me choking on and swallowing Zander's huge cock after I let Nate and Trevor finish inside my mouth. Maybe I could indulge in your guys' cocks while you play video games." She clutched Dan's shaft tightly, her thumb gliding across the sensitive head. "Would you appreciate it if your girlfriend becomes your friends' cum guzzler?"

Dan croaked "yesyes" as his cock jerked, his cum ejaculating onto his stomach.

Madeline giggled and kissed his earlobe, "You may announce the good news to your friends after prom, ok?"

She gripped his shrinking cock then sang it into her mouth, guzzling the remaining hot liquid, then cleaned his belly of the remaining cum.

"Swallowing your semen makes me crave a massive, thick load. I wish Mr. Scanlin was here so I could fill my tummy with his fullness."

Dan's head was spinning with the incredible events of the day. Had he really consented to inform his friends that Madeline would be their mutual cock slut?

Read also:

• Ruthie's Dedication and Zeal
• Love and Truth Aid in Rescue Mission
• Anu's Collision Chapter 2
• The Erroneous Mile-High Incident