Erotic Couplings

Dan's Tale: Chapter 1

The journey to becoming Dan Boykin.

Spankmasters
May 27, 2024
22 min read
coming of ageDan's Story Ch. 01maturehungcuckold
Dan's Story Ch. 01
Dan's Story Ch. 01

Dan's Tale: Chapter 1

For those who have followed the Young Couple/Older Neighbor series, this story Elaborates on Dan Boykin's timeline from when he turned 18 up until his wedding to Callie, five years later. This can be read without prior knowledge of the other piece.

Kudos to AlphaBetaCajun for their editorial skills.

Remember, all sexually active characters in this tale are of age.

On Dan Boykin's 18th birthday, his parents took him out for a customary birthday meal. His younger sister Samantha had informed him earlier that day via text. Absent in the United States, Samantha was spending her senior year of high school at a prep school in Palo Alto. She had already received a full scholarship to Stanford to play volleyball. Dan had observed that his father's business partner, Frank Scanlin, awaited them in the driveway.

"Mr. Scanlin will be joining us for dinner," Dan's father, Richard, clarified. "You'll occupy the front seat with him."

Dan had recognized Frank Scanlin since birth. Frank was the owner of Atlas Consolidated, and his father held the position of company president. Frank was a frequent visitor to their home. Dan still remembered the weekends at their grandparents' house. In the summer, they would stay there for two weeks, with Frank visiting multiple nights. Dan could vividly recall many occasions where his mother served Frank beer at the dining table while the two discussed business. Samantha and him adored those moments.

The four sat at a table towards the back of the restaurant. Dan and Richard on one side, with Frank and Sheila to their opposing side. His mother was clad in a sundress with a generous neckline, exposing the small but perky breasts within. Dan observed that Frank had ordered for both his parents, causing them to look apprehensive. Frank maintained his usual jovial demeanor, inquiring about Dan's college plans, teasing about girlfriends, and complimenting his impressive SAT score. After they had completed their meal, Frank entrusted the keys of his Cadillac SUV to Richard, indicating for Dan to get into the rear. As Frank gestured, Sheila climbed into the center seat, with Dan and Frank both sliding in. The silence from Dan and his father persisted as the car proceeded. Dan noticed Frank's large hand tracing Sheila's thigh, causing her skirt to climb upwards against his movement.

"I first encountered your parents when your mother was two months pregnant with you, Dan," Frank disclosed. "I was expanding my company and sought an individual to run operations locally. A friend of my fraternity brother's father was involved in the local economic board, and he had endorsed Richard. I dined with your parents to ascertain if I deemed him an excellent candidate for the position. I was impressed by his expertise and resume."

Dan tried to focus on Frank, but his eye-popping mother's almost naked form made this challenging. When Sheila dislodged herself from Frank's lap, revealing her covered but clearly visible ass. He scrutinized the blue g-string, then noticed a dark blue butt plug protruding from her opening. Dan became aware of the nakedness beneath her panties, her exposed bald pussy.

"I first met your dad on a Monday, and I welcomed him and Sheila to dinner the following Friday. The moment I laid eyes on your mother, I intended to copulate her," Frank stated, turning his gaze towards Dan. "Feel free to address any questions you may have. Your mother will provide you with the appropriate information."

During the rest of the car ride home, Dan observed his mom sucking Frank's cock. His attention was drawn to how large it was and how much enjoyment Sheila seemed to derive from it. She grunted and drooled all over it. When she removed it from her mouth, she spread the slippery shaft on her face, then guided it down her throat, with her face buried in Frank's crotch and the sounds of her swallowing filling the car. Prior to reaching home, Frank gripped a handful of Sheila's hair and shoved her face up and down his cock, after which he pressed her down and grunted as he released his sperm down her throat. She then lifted her head and licked his cock clean before tucking it back into his pants. Her face glistened with moisture from her saliva and Frank's semen, and her eyes had a contented expression on them.

Once Frank left, he gave Dan and Richard a handshake, hugged Sheila, and exited the vehicle. The family walked into their home without exchanging any words, with Sheila carrying her dress. Dan, dazed, followed his parents into the living room where Sheila positioned him beside her on the couch and had Richard sit opposite them in the recliner. Undeterred by her naked, pierced breasts, Dan was unable to shift his gaze from them. He had fantasized about his mom several times whilst masturbating, primarily because he had witnessed her in risqué attire and swimsuits throughout his lifetime. At 38 years old, Sheila still had the appearance of someone in their mid-twenties. Her actions prompted movement across the room, resulting in Dan's head turning to see his father standing and disrobing as well. When Richard was naked, Dan was unable to deny the stark contrast in size between Frank's penis and his own father's. Dan blanched, certain his erection resembled his father's in size.

"Richard," Sheila suggested casually, "why don't you head up to bed? Dan and I would like to have a conversation."

Richard consented and vacated the room. Sheila then turned back to her son. "If you would like to listen to my tale, remove your clothing."

A combination of arousal and nerves caused Dan's trembling. While he could not avoid looking at his mother's hand stroking her pussy, he felt embarrassed to stare in that area. Her breasts, however, captivated his attention. He had imagined his mom naked frequently, mostly because of her attractive costumes and bikinis his whole life. Unsure of what to say, he finally managed to speak.

"What do you mean, mom?" Dan inquired, his voice barely audible.

"I imply if you wish to hear my story, take your clothes off," Sheila suggested, continuing to touch her pussy.

Dan reluctantly stood up, promptly discarding his shoes, slacks, boxers, and shirt. He took a seat again, covering his hardened penis with his hand.

"Sheila, you're my mom. I'm not interested in sex with you." Dan specified, the embarrassment evident in his expression.

A small smile played on her lips as she said, "Dan, I understand you have an erection. You're very much like your father in that regard."

"Mom, I know your stance on infidelity and all, but-"

"My positions on such matters have switched since my encounter with Frank," Sheila interrupted. "Richard is a submissive man. He enjoys the fact that his wife is a whore who craves other men's penises. I didn't recognize I was a slut until I met Frank. When I first met him, I was a twenty-year-old, pregnant wife. I considered my sex life good, albeit not great, but I was content. Frank entered the picture and showed me what I was missing. He never coerced me. In the space of a week, Frank became aware of Richard and me, and we had many conversations. By the third day, I was soaking through my panties just thinking about him. He recognized it and mentioned that he would be extending a job offer to Richard. He hinted that if I longed for him to penetrate me, I'd have to ask him in front of Richard," Sheila shared, stroking her clit as Dan's eyes were drawn her exposed folds. "Your father is a cuckold, Dan, and I'm your cuckquean. We grant each other sexual license. The open invitation is constantly available, Dan. All you have to do is ask."

Without a second thought, Dan immediately began playing with his mom's exposed pussy. His tongue found its way to her clit, tonguing it. She moaned, and his mother wrapped her legs around his head, urging him deeper. He could taste the love juice leaking from her core, which she motioned for him to devour.

I'd been working my job since 8 am and coming home to change out of work clothes into shorts and a t-shirt, but when Frank showed up on Monday, he asked me to dress nicer. I wore a cute sundress and he liked it. The next day, I put on a short skirt and top when he arrived. He greeted me with a cheek kiss upon arrival and departure. On Wednesday, Frank requested Richard's approval to take me out to lunch. He picked me up at 2 PM, and my outfit was a shorter skirt and tighter top. This time, while saying goodbye, he went in for a kiss on the lips, surprising me. Later that day, Frank dropped by while Richard was still talking to him. I could feel my sex ready for more of Frank's attention. While preparing for bed, I chose a conservative dark red lace nightgown coming down to mid-thigh, partially see-through and revealing my nipples and panties. My pussy was even dripping when he left, soaking my panties.

On Thursday, Frank served lunch at their house, asking me to get dressed after the meal. This time, I slipped into a light blue sheer lace camisole and matching g-string. However, Frank hadn't touched me in any explicit way since his arrival. My wet pussy caused my panties to soak through once more.

Frank then privately messaged Richard and me, inviting us to his hotel room for dinner and drinks, claiming he had reserved a private suite. Before leaving, I stuffed my belongings in a bag. We arrived, and he treated my husband to a generous salary increase with stock options. By this, we were both astonished. When my husband questioned if the offer was connected to our sexual relationship, Frank chuckled and expressed that himself, his dick, was too important for his company's reputation.

While I ran to the ladies' room, I hid my soaked panties in the trash. At the table, Richard drank his bourbon with Frank while I sat next to Frank. His hand rested on my thigh and crept up on contact with my moist pussy. I further impressed him by displaying my control over my body, reaching the verge of climax but holding back.

Frank left for a minute, then asked me to go to his room. My husband stayed in the following room for privacy. When I got there, he ordered your father to the other room while Frank made himself comfortable. He lifted the skirt of my little black dress with enough length to showcase my braless breasts. My husband was confused, perhaps, seeing his wife's ass on display, so Frank instructed him to strip, promising a story he'd never forget about his wife becoming Frank's.

Then, Frank, my hubby, and I had four hours of the best sex we have ever experienced. His shaft was enormous - twice your dad's size. He knew how to use it to make me scream. As I left the room, my father silently acknowledged the gravity of what had just happened and imagined himself unloading on that dick. I was now a fuck toy to Frank, showing my husband the difference between ordinary sex and the incredible sex his boss offered me. My husband sat in that chair, watching Frank engage with me, and surely burning off some manly fluid.

"From that point on, Frank Scanlin possessed my body. I adored your father still, but whatever Frank did to me, I ended up enjoying immensely. Frank delighted in tormenting my expectant figure, and relished exhibiting me off to his acquaintances. My initial encounter with him getting me into the swing of things was through George Simpson. George was sixty-eight years old, while I was twenty with a prevailing baby protruding. Your dad had just started his fresh position a month or two ago, therefore around the period when I was somewhere close to four months gone with you. At first, I was working dawns, and this particular day Frank had texted me to notify me that a friend was going to pay me a visit at 3 pm and that I was to greet him wearing the blue camisole and underpants I used to wear the initial day Frank and I connected. I had never encountered Mr. Simpson previously, but the determination in his eyes on me sporting my attire when I opened the entryway sent a tingling sensation through me. He asked me about my expectancy when we were sitting on the object, and his palms soon scouted over each part of my body. By the time your father came back home around 6 pm that day, I had given up a quite large cumshot, then relaxed him into another erection. Mr. Simpson's cock was above-average sized, still bigger than your father's. We were both in the raw in the master room when your Dad strolled into the entryway. I was tracing Mr. Simpson's dick while he exploited my small mammary glands and pregnant tummy. I had cum at least four times, and as Mr. Simpson overflowed my pussy, I came a fifth time. I flourished at your Dad before guiding Mr. Simpson into the rest room and showering with him. Your dad was on the sofa in the front room when we returned."

"Did Mr. Simpson and you, um, share the same bed again?" Dan pondered aloud. He could pick up his mother's excitement as she continued rubbing the swollen vagina.

"Did Mr. Simpson and I take a tumble again? Sure. Mr. Simpson was ardently engrossed in my pregnant body, and Frank entirely supported this. He also authorized a couple more elderly pals of his to use my body at times. Throughout those two months that Frank was still working away, George would flit over every Wednesday. He arrived single some times, and other times he was accompanied by friends. One of his frequent pals was Jonas White, a seventy-five-year-old individual who relished my diminutive tits. By the time I was clocking in at six months pregnant, they had sprouted to respectably-sized B cup. Jonas frequently sucked them for many hours every time he was around. Additionally, Jonas adored ramming his erect penis into my asshole. He was the one who opened my posterior, and Frank and Rowan jointly subtly tutored me how to appreciate the pleasure of a penis in my vagina as well as a penis up my butt.

"Are Mr. Simpson and Jonas White, like...?" Dan was doing the math in his head.

"Both of them passed away a few years ago. I'd visit them on Mondays at the elderly residence they lived in. George had deteriorating memory so he didn't know where he or what he was doing most of the time, but he became aroused every time I engulfed his dick. After I swallowed his cum, he would smile as he napped. Jonas' mind was razor-sharp up until the end, but he suffered a stroke and was stricken with paralysis. His gorgeous, coal black knob still got firm, and he was always keen for me to perform cunnilingus on his dong until his cum flew into my gobsack. I mourn for both of them."

Dan experienced his mouse getting harder as his mom described hearing older guys have intercourse with her. "Um, did your dad know you were working it with different guys?"

"Your father rapidly recognized that what he preferred my lower part for didn't materialize," Sheila replied. "After my second weekend with Frank, the lone opportunity that your dad could spurt into my pussy was when it was already chock-full of another man's semen. I could scarcely sense his knob. Lucky for him, though, he took joy in my dingy, slick vagina. He couldn't begin to last longer than a minute after he started penetrating my flimsy, goopy vagina."

Dan experienced his mom's hand grasp the foundation of his shaft. He surged forward, and sensed the scorching, damper vagina ingulfing his cock. He palsied with the sensation. Her vagina wasn't tight under his dick, but it was like he had plunged his prick into a bucket of boiling wax. He could sense her supple, soft vagina lips pressed against his hairless crotch.

"Goshhh, MOMMMEEEE!!!" Dan had never perceived an experience remotely as pleasurable as his mother's vagina coating his penis.

Dear reader,

Do you enjoy anticipating the smooth texture of your mother's vagina? I barely feel you there, just like your father. Sheila shared this information with her child, whispering softly into his ear, "You know I got pregnant right after you were born. Richard and I were planning on waiting a couple of years, but Frank found me appealing when I was pregnant, so I didn't go back on birth control. Frank was the first and only man to penetrate my vagina until he got me pregnant."

Dan felt his testicles tighten and experienced orgasm within his mother's vagina. After a moment of rest, he repositioned against her, his mind exploration was loaded with what she had revealed. His younger sister, Samantha, was close in age, around a year younger, but she bore little resemblance to their father. With a towering size, dark features, athleticism, she was an embodiment of their father Frank Scanlin.

"Has Samantha been made aware of this, Dan?"

"Mom, you're implying my younger sister may have realized these facts," he responded hesitantly.

"Oh, honey, Samantha has known for a while." Sheila brushed her son's cheek lovingly, "Little girls tend to observe things keenly. I detected her casting me sly looks for several months before she inquired directly. Do you recall Samantha's visit to volleyball camp in New Haven prior to her freshman year?"

Dan tentatively nodded. He and Samantha were in the same grade, though he was held back a year because he was small. Samantha was an imposing figure, standing six feet tall at the onset of high school, substantial shoulders, long straight black hair, and mesmerizing cobalt blue eyes.

"During this period, she came to know a witty young woman named Samantha Goins. The latter's father worked in New Haven for Frank. Technically, the man raising her. The Samantha Goins resembled him exponentially, that everyone at the camp mistook them for twins. Upon her return, Samantha shared an intimate chat with your mom. Believe it or not, she exhibited similar traits as her biological father; confident, intelligent, and dominant. Mother divulged the entire truth to her."

"Then there's another Samantha, is that correct?" Dan inquired dubiously.

"Yes, love, I am not the only woman Frank has deceived and women who conceived due to him. You shouldn't be astounded when you realize a capable, virile man like Frank wouldn't be content with only one woman, such is his nature."

"Why use the same name for both?" Dan perplexed.

"Notably, Frank's middle name is Samuel."

Sheila bestowed a kiss on her son's cheek before heading upstairs. Belatedly, Dan had moved into this house when he was ten; a massive, sprawling one-story dwelling with the master suite and a couple of bedrooms on the upper floor, while the children's bedrooms were on the ground floor, each separated by a shared bathroom. Dan remembered how his father Dick often remained downstairs during some of Frank's many overnight visits, and his mother was excused upstairs when he was still in bed.

Congruent thoughts about his mom's shopworn nudity and the way her pussy felt in his hand jolted Dan. Images of his mother's body kept materializing in his mind. His four-inch erection regained turgidity as he jerked off onto his abdomen before tidying up, retreating into sleep.

The following day, Dan was occupied in a friendly game with his peers when his cell buzzed, acknowledging a message from his sister. Permitting his friends a quick escape, he removed his headphones and fielded his phone.

"Hey Samantha," greeted Dan.

"Hi, Danny! How will you not inform me about your recent experience with mom's now battered vagina?" Samantha said, her voice merry.

"Well, Samantha, I...," Dan trailed off, flustered.

"C'mon dude, I got a vivid image of your recent intimate encounter!" Samantha asserted lightheartedly.

Dan could not help but feel aroused by her voice. Against his better judgment, his four-inch stiff shaft responded to her inquiry. "It was majestic," Dan replied, still flustered.

"I'd guessed as much! When will your intended visit me?," she inquired mischievously.

"Soon," Dan replied, his tone emulating a sense of reluctance mingled with excitement.

Their conversation carried on for a while longer, discussing other random matters. Eventually, they signed off, and Dan returned to his gaming.

Days passed, and Dan consciously strove to come to terms with the fact of his mother's infidelity but struggled. Finally the day came when he decided he should meet with his sister to clarify doubts. At the crossroads between indecision and the decision to meet her, his phone beeped signaling a message from her.

"En route to your place, Danny. See you soon."

In response, he simply nodded.

I had to head off to the gym, but I couldn't help but congratulate you for losing your virginity! Love, YOUR annoying little brother! Yep, my mom told me about that, too.

After graduating when I was 18, I thought things would change between my parents a bit. However, it remained mostly the same. The major difference was that my mom was no longer hiding things from me. I came home from school one day and heard my dad on the phone in the living room. I got a drink from the fridge on the way to my room and looked into the living room as I walked past. I saw my dad sitting in the big chair while my mom knelt naked between his legs. He was wearing a suit, but my mom had his cock out and was slowly taking it in her mouth as she spoke to a business associate on the phone. When she spotted me, she simply smiled and waved, never missing a beat in the conversation.

My mom was either naked or in sexy lingerie all the time in our house from then on. When my dad was visiting on the weekends, it was so obvious - no secrecy. I'd often walk by and see my parents in various sexual acts. Most evenings, my dad would be in his recliner while my mom and dad cuddled on the couch. I'd usually just go to the kitchen, but I'd catch glimpses of my mom sucking my dad's cock, riding him, or just lying half-naked on his lap as he gently handled her buxom body. When my dad wasn't there during the week, my mom would invite me to join her on the couch for a chat. Our conversations consisted of her telling me stories of all the horny things she did for my dad over the last 19 years. Of course, I always had to be naked while my dad sat in the recliner, jerking off as his mom shared her wild tales. My dad encouraged me, making it a point to rub his big cock hungrily on his open wife's naked body. I did that a lot.

By the end of my first semester of my final year at high school, I almost felt ready to write an entire book about raunchy sex, all thanks to my mom's stories. To the outside world, she looked like the innocent housewife. She's barely 5 feet tall, with shoulder-length blonde hair and sparkly blue eyes. She volunteered at the school library and was even involved with the volleyball boosters despite her daughter not being there, but no one could guess she had tiny, pierced nipples or that sometimes she had a huge butt plug under her sundress when she was there. I knew my mom looked innocent, but in reality, she was a shameless whore for my dad. Knowing my parents' crazy marriage only made Dan's fantasies more intense. He spent loads of time jerking off to his own mom's stories and watching pornography every day.

Towards the end of his final year in high school, Dan met Madeline Walters. She was new at the school and they were paired for Chemistry Lab by Mr. Dobbins. Dan and Madeline, both nerds, spent hours talking during class. After a few weeks of lunching together and plenty of texting, Dan built up enough courage to invite Madeline over for dinner. She happily agreed, saying she'd be home by 9. Madeline was short, around 5'1", with long, light brown hair, hazel eyes, and wore glasses. Despite her frumpy style of dress, Dan thought she was gorgeous. She had such expressive eyes, and her juicy, pouty lips. She wasn't heavy into make-up. When he told his parents about Madeline, they urged him to invite her over. So that Friday, Madeline rode home with Dan after school. Her mom trusted her, telling her to be home by 9 PM. Madeline had on a long skirt and sweater, plus she had a little makeup on. To my parents, they wanted her to make a good impression. Dan felt nervous, never having dated before.

Sheila awaited Dan and Madeline's arrival. Her outfit consisted of a knee-length skirt and a loose, thin sweater, which accentuated her stomach a bit. She hugged Madeline and instructed her to sit at the table with the snacks Sheila had prepared.

"It's such a pleasure to meet you, Madeline!" Sheila excitedly informed Madeline, her face beaming with enthusiasm. "Dan hasn't stopped talking about you. He says you're the most attractive girl in school, and he's right. You're a doll!"

"Mom!" Dan blushed, embarrassed.

Madeline blushed as well, but her smile couldn't be hidden. She found it endearing that Dan thought so highly of her.

"We're going to watch some videos, right?" Dan asked his mom.

"That's fine. I'll let you know when dinner is ready."

Dan and Madeline ventured into the game room, which was right next to Dan's bedroom. This area had four theater seats and a projection TV with surround sound. Dan had connected his gaming computer to the TV to play his video games. At the back of the room was a small table where Dan studied. There was also a couch positioned to the side where Dan enjoyed reading comics.

"Wow, Dan, this is amazing!" Madeline expressed her excitement as Dan showed her the setup. "My tiny 36 inches TV and Switch seem insignificant in comparison."

"Yeah, I set this up by myself." Dan settled in with the remote and turned on the system.

Madeline sat beside Dan and they watched two episodes of Demon Slayer. She had already seen these episodes, but never on such a huge screen before. Dan couldn't help but observe how much Madeline was enjoying herself. He knew her dad had died when she was ten, and her mom struggled with the bills, as well as raising two daughters. Dan suddenly realized how fortunate his circumstances were in comparison.

Just as Sheila entered the room and instructed them to clean up for dinner, Dan caught a glimpse of Frank Scanlin, also known as Frank, in the background. Despite the fact that he spent a couple of weekends a month with them, Dan was still caught off guard by Frank's presence.

Dan's eyes widened when he saw that Frank would likely have sex with his mom soon. Dan sat across from Madeline, who was at the head of the table, while Frank was at the head of the table as well. Sheila was positioned next to Madeline, and Richard was beside Dan. Frank swiftly shifted the focus of the conversation at the table as they enjoyed their meal, frequently directing the majority of his attention toward Madeline. By the time dinner concluded, Madeline felt more at ease discussing various topics with Frank.

"Richard, should you not be preparing some reports for me?" Frank requested, rising and allowing Madeline to exit the dining room before him.

Richard didn't possess any reports, but he interpreted this as a dismissal. He left the dining room, not before glancing back at his son, who was assisting his mom in the kitchen. He remarked to himself that Madeline looked much smaller than she had from afar.

Madeline felt a sense of unease as she sat on the couch next to Frank in the living room. She'd found the conversation at the dining table enjoyable, but being alone with him had her feeling insecure. Frank remained seated next to her and continued talking, gently prompting her to share more about her past.

Dan couldn't help but peer into the living room from the kitchen while Sheila cleaned up.

"It's alright, honey. Frank is simply getting to know Madeline. You enjoy her company, don't you?" She assuaged Dan, patting his arm. "She's adorable. And petite. Have you kissed her yet?" Sheila and Dan had just finished cleaning the dining room when this conversation took place.

Dan shook his head. "I'm not quite sure. It's difficult for me to determine if she wants me to do it or not."

"I think she does, but both of you seem hesitant. Girls her age require affection, or they're prone to find someone who appreciates them." Sheila revealed her belief that Madeline wanted Dan to make a move on her.

Dan admitted, "I truly like her. She's easy to talk to."

"She's very pretty. And small. Have you kissed her?" Sheila asked Dan, who had just helped his mom close the dining room.

Frank unexpectedly appeared in the doorway, with Madeline by his side. He had his arm wrapped around Madeline's waist, and she rested against him.

"Hey Dan, why not take your girlfriend for a scoop of ice cream on the way home?" Frank nudged Dan towards Madeline with a wink.

Dan hesitantly replied, "Um, okay... if you want me to."

Madeline smiled and nodded. They said their goodbyes to Sheila and left. Twenty minutes later, Dan and Madeline were sitting in his car in the parking lot of the ice cream parlor. Dan's heart beat wildly, as he was incredibly nervous. They polished off their ice cream cones and sat silently in the car for a moment. Dan then started the engine and drove towards Madeline's apartment complex. He stopped the car and turned to Madeline.

"Um... Madeline, I had a great time with you today." Dan glanced at her.

"I did too, Dan," she said, glancing back at him. "Your mom was so nice. And Mr. Scanlin is a gentleman."

Dan's mind came to a halt as he recalled the images of his mother having sex with Frank. He felt his small dick harden, but forced himself to think straight. "Would you like to come over again? Or go out with me?"

She agreed, "That sounds like a plan."

Dan beamed, his cheeks hurting from the wide smile. He got out of the car and walked around to open Madeline's door. They entered her apartment and met her sister, Trina, and her mother, Donna. They chatted for a moment before he left.

"Oh, one more thing, Mom," Dan recalled. "Mom wanted me to give you her phone number."

Donna took the paper, "I'll call her soon."

On the drive home, Dan was still elated over Madeline's kiss on the cheek, the first kiss from a girl other than his mother or sister. He thought about their conversation and how frustrated he was with his lack of experience. However, he was soon distracted when he walked into the living room and saw his dad naked on the recliner. Frank was on the sofa with Madeline's mother, Sheila, on top of him while her ass undulated rhythmically up and down on Frank's lap. Dan's gaze strayed to Sheila's dripping pussy, before Frank spoke.

"Dan, could you come here for a moment, please?" Frank requested with a casual tone, lightly kneading Sheila's clit, causing her to moan.

Dan paused before walking into the living room. Despite Dan's present state of mind, Frank casually displayed his mother's nudity, "I found your chats with Madeline enjoyable. She's a very attractive girl, don't you think?"

Dan struggled to respond to Frank's blunt remark. "Y-yes, she's very attractive."

"I could imagine how excited you must be about potentially dating her." Frank continued to pay attention to his mother's needs while Dan's eyes were glued to his mother's pussy. "I'm sure there's an amazing body under those loose clothes."

Despite the awkward situation, he couldn't deny that Madeline looked great. "Y-yes, she certainly does."

"You know, fresh, tight and young pussy is a delight," Frank added, as he brought Sheila to a climax. "Her mother's still got a fantastic body, but there's nothing like a young girl's pussy."

"F-f-Frank, please let me finish," Sheila begged.

Eventually, Dan was able to tear his eyes away from his mother's almost exposed crotch, only to find Frank still staring at him. "Remind Madeline that I hope to meet her again soon."

"I'll do it," said Dan, barely able to speak with his now dry lips. He stood there for one more minute, watching as his mom squirmed in Frank's lap, her fingers tightly gripping Frank's arms as she fought to maintain her composure. At a nod from Frank, Dan left the room, and just before reaching his own room, he heard his mom cry out in ecstasy.

Dan sent Madeline a message as soon as he got to his room, relaying Frank's message. She responded with a smiley face. They chatted for a bit longer, with Dan watching porn and stroking his little penis the entire time. Less than five minutes later, after telling Madeline good night, Dan caught his small load on a napkin while watching a video of a big older man forcing his huge erection into a smaller, younger woman, all while her timid husband watched from the floor.

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