“Is this honestly what you’re wearing for a date, young man?” Gina’s question got an angry scowl from her eighteen-year-old boy.
“What’s wrong with it?” Philip retorted. He was dressed quite fine, thank you very much!
“Jeans and a hoodie. Your torn, day-old hoodie that I told you to wash yesterday.”
“It’s comfortable! And this isn’t a real date, Mom!”
Philip could see Gina’s eyes flash red at his words. He was on thin ice. They lived in the nation of Schoka, a nation that had evolved in isolation from the rest of the world with its own quirky structures. It was slowly getting modernized, but a lot of those old-world rules and etiquette remained.
“I didn’t mean to snap, Mommy,” Philip bowed his head slightly in submission. Philip, much like a lot of youth, wasn’t Gina’s biological son, having been raised in communal towns with a bunch of other boys and girls.
He moved to the big city last year and got paired with his caretaker in Gina Flowers, a beautiful twenty-six-year-old architect. The ages below twenty-three were considered the ages where boys needed a firm, feminine mother figure in their lives to turn them into proper gentlemen. She was his “Mommy,” a specialized role in their culture that had additional responsibilities and authority to a usual mother.
Gina had come home from work and decided she didn’t want to make dinner and declared they were going out on a date. She had picked a nice restaurant by the lakeside and ten minutes ago told Philip that it was going to be a “special lesson” where the boy learns how to treat a woman.
“Corner, now,” Gina ordered the boy.
“Yes, Ma’am,” Philip quietly walked over to the corner of her bedroom, a familiar spot.
“You know I’m doing this for your sake, right, Philip?” Gina scolded. She was dressed in a T-shirt and blue jeans; the T-shirt stretched tight over her big breasts. “It is my duty as your Mommy to make you a proper man whom girls want to marry. Your cute looks will only get you so far.”
“I don’t want to get married! It sounds awful—like you don’t want to get married either, right? Why else would you choose to get stuck with me?” Philip snapped at her.
“This again?” Gina rolled her eyes, moving over to the boy in the corner. He was a handsome lad on the school athletics team with blonde hair and pale eyes. “I took you in because I like you, and I’ve always wanted to become a mommy first to a little troublemaker before settling in.”
Philip felt her palm on his rear, giving it a small squeeze. “You just like spanking me.”
“You are always so cute across my knee,” Gina didn’t refute his accusation. “And you will be going over it multiple times if you take me on a bad date.”
He felt her fingers slide over to unzip his jeans, sliding both his jeans and undies off. “Mommy, wait! Not right now!” Panic had set in.
“Oh, right now,” Gina concurred. “Step out of this stupid outfit. I want you to go to your wardrobe and pick some of the nice shirts and trousers I’ve bought for you.”
He blushed, complying as he moved out of the corner to peel his clothes off. His eyes flicked over to Gina, her makeup having been done, and a nice gold dress lying out on her bed. “Am I getting spanked now?” He asked timidly as he folded his t-shirt and jeans neatly.
“That’ll depend on what clothes you pick,” Gina replied. “And put these away. You will start wearing proper clothes from now on.”
He quickly slithered out of her room. They lived in a nice high-rise apartment in the middle of the city. Philip could see the flashing lights of cars and the glitzy buildings from out of the wide glass panes in the wall. He was thankful they were high up and couldn’t see him walk around their apartment in just his underwear.
But then again, he knew any wrong move today could end with him dragged across Gina’s long legs. Corporal punishment was so frequent and common that half the people didn’t even notice if a boy or girl his age was bent over and getting spanked.
Philip got into his room, putting away his comfy hoodie and jeans in the hamper and going to his wardrobe. It had a few of the regular clothes he liked to put on, plus a small collection of cute pajamas with an open butt flap, which Gina made him put on if she spanked him. Next to it were a couple of canes and a small bottle of special healing oils that Philip eyed nervously as he looked over at the expensive shirts she had bought for him.
Just like him, Gina had been taken in by Frederick Flowers, a wealthy father who had provided her with this wealthy, independent lifestyle. She worked in his office and was a very accomplished architect in her own right. Both of them made sure Philip was set for the same path, which the teen was still coming to grips with.
He picked a white shirt and grey pants, the most boring combination, the likes of which Frederick would wear. Hopefully dressing up like her daddy would impress the wicked spanky witch of the west, he thought to himself as he made his way back. Ooh, how he wished he could’ve seen some of the biblical ass-whoopings Frederick spoke about giving Gina! The prim and proper lady is bawling her eyes out. There were supposedly videos of them in his collection, which he had been coaxing the old man to share with him.
Though sadly, it was his own ass that was in peril right now. “May I come in, Ma’am?”
“Yes, you may,” Gina answered as he got in, letting out a cute yelp. She had peeled her jeans and top off, leaving her just in her purple panties. The armless spanking chair had been moved to the middle of the room as she stood beside it, hand on her hip.
“This is nice, right?” He held up the shirt, trying to ignore her gym-toned body and her heavy, bare breasts that seemed to defy gravity.
“The Accrel Swiss shirt Daddy got you?” Gina nodded, seemingly impressed by his pick. “That does pair nicely with those pants.”
“Can I put them on then, Mommy?” Philip asked her.
“Not yet. Not before we have a discussion on how I expect my gentleman to behave during our date,” Gina said, sitting down and patting her thighs.
“Oh please, Ma’am, can we not have a spanking before we go?” Philip pleaded as he got down on his knees next to her, laying his head on her warm thighs. “I’ll be squirming all the time, and everyone will notice.”
Gina shook her head, picking him up with surprising strength as she draped him over her knee. “Oh no. You have earned this.” She slowly pulled down his underwear to his knees as his legs dangled up high.
“You can spank me when we get home then! How about that, Mommy? We have to get there in half an hour, and we’ll lose our reservation!”
His words gave Gina pause. “Hmmm, true,” she said, softly rubbing his butt. “But you will be getting it when we get home. You have been quite mouthy with me all evening, young man. Ever since I said we were going on a special date.”
“Because dates are for people who are like…in love and shhhit…yyeooww!” Philip yelled out as his words earned him two sharp spanks across each cheek.
“Language, mister!”
“I’m sorry!” Philip begged as he got two more spanks before she let him up.
“I will not tolerate any filthy language when we are out. No outbursts or angry rants. When we are out, you will be polite and respectful of me and any other women. And none of that cheek.” Gina wagged her finger at the boy.
“Yes, Mommy,” Philip nodded quickly as she stood up. “Do I still call you ‘Mommy’ when we are on a date?” He asked as she moved towards her dress.
“Why wouldn’t you? It’s how boys are expected to address other caretakers,” she said calmly.
“Alright, Mommy,” Philip looked at her, eyes focusing on her bare bust. He bit his lip. “Did…you take a lactation pill, ma’am?”
Gina smirked. “Surprised you even noticed; I just took it fifteen minutes ago. You pay waaay too much attention to my breasts, little boy.”
“But that’s for after the date when we get home, right, Mommy?” Philip asked her nervously. He was still getting used to the idea of breastfeeding, a special bonding ritual between the pair. The intimacy of which he liked as long as she didn’t go talking about it with everyone she knew.
“Oh, it depends on your behavior, Philip. As long as you’re a gentleman for the trip, you get to come back home and go to sleep in Mommy’s bed nursing my breasts,” Gina leaned down to bring him close to her bosom, dangling a small carrot. Which Philip took quickly, kissing and licking her perfect breasts as his cock twitched.
“But if you are annoying or argumentative or act like your usual bratty self, both your spanking and your feeding are going to be at the restaurant, in front of everyone,” Gina hummed, pulling away as he tried to latch on. “Now go put on your clothes. We need to be there before seven thirty.”
Philip rose up and went to put on his shirt, averting his eyes as he didn’t trust himself to not get aroused around Gina as she changed. He knew Mommy was in a position that was different from that of a traditional mother. She was expected to be the one who would guide him when it came to sex. Her responsibility was to ensure Philip turned out to be the right boyfriend material for a future lucky lady.
“Did Gramps take you on dates?” He asked her as he put his shirt on before getting his pants.
“He would often,” Gina replied with a small smile. “He enjoyed taking me to the nice hotels around the city when I was in your position.”
“Figures,” Philip muttered under his breath. “What I mean is…” He quickly backtracked when he saw her catch him. “…like… it’s very… girly.”
“Girly?” Gina laughed. “Going out on a date is girly?”
“Yeah, like…I dunno…like in the movies you like watching.”
“Do you mean romantically?” Gina was amused by his words. “Dear Goddess, what a dense boy you have blessed me with!
“Hey!”
“You need to learn to be romantic when taking a girl out,” Gina explained as she put on her dress.
“Hey! “You forgot your bra!” Philip pointed out. She looked much too revealing in his eyes. “That looks… slutty.”
The word escaped his lips right before his brain registered it.
“Second demerit for your spanking when we get home,” Gina scolded sharply, walking over to grab the thick spanking belt she used. “Put it on. In case you feel like making any more of such comments about my appearance when we are out.”
“No, ma’am.” Philip bowed his head submissively as he put the belt on, hoping she’d forget to use it on him when they got home. He allowed her to finish up, following the beautiful woman out of the door and down the lift to her car park. Gina chose her purple sports car for the trip.
“Can I drive?” he asked her. “The man is supposed to drive, right?”
Gina looked at the lad. “Fine. But you will not be reckless with it.”
Philip beamed as he got the key. Finally! Something good out of this!
“Lady Williamson’s south of the Oakland Bridge.”
“I know,” Philip replied impatiently, noticing her change in demeanor. Whatever, he thought as he drove. It wasn’t often she allowed him to drive; the long-standing tradition was cars weren’t allowed to be driven until he was twenty-one.
“Careful, Philip!” Gina snapped ten minutes later as he made another rash overtake.
“We need to be there in three minutes,” he responded, again driving recklessly. He was lucky to miss the police as he finally got to the restaurant. Turning to see an irate Gina glowering at him.
“We need to hurry, Mommy—yeoowww!” Philip cried as she grabbed and twisted his ear.
“Is this how you drive?”
“Owww…but we were late!” Philip begged, eyeing her with his big puppy eyes.
“We will discuss this,” Gina replied coldly as she got out. The valet by the parking area noticed the exchange and had a small smile as he took the key from a pouty Philip.
He followed Gina as she quickly made her way over to the reception. “Philip, you don’t walk behind your date ogling their ass. You walk beside them.”
Philip blushed when she made the comment loud enough for the lady receptionist to hear.
“But you have such a fine ass—um, posterior, Miss,” Philip replied, in his mind, with the perfect compliment. Gina did have a nice rear.
“Cheeky, isn’t he, Miss Flowers?” The receptionist grinned.
“Quite the charmer.” Gina rolled her eyes before giving an exasperated smile.
“Well, boys require more attention than girls, from my experience. I’m sure you can turn young Master Flowers into a proper man,” the receptionist smiled warmly. “We have your usual seat overlooking the lake. Near to the scolding room if you require a more… private conversation with your lovely date.”
Philip instantly disliked the woman. “What a bitch!” He muttered under his breath as she led the pair. Only to be rewarded with a firm swat to his bottom by Gina, loud enough to get the attention of the other patrons.
“You need to learn to stop vocalizing your stupid, intrusive thoughts, Philip,” Gina hissed into his ear as he was led to his table by the lady. The restaurant was extremely cozy with warm, woody hues and around twenty tables. The clientele seemed to be wealthy, a few older gentlemen and younger ladies, though there were a couple of boys his age with women slightly older than Gina’s.
“Oh, don’t you mind, dear. I’ve been at this establishment far too long to be bothered by a bit of lip,” the receptionist explained good-naturedly. Even your MMommy—”
“Oh come on, Lisa!” Gina shushed the receptionist.
Lisa, the beautiful redhead, let out a cute giggle. “Miss Gina frequented our restaurant with Master Frederick over the years. Even earlier, when Master Frederick had Miss Emily and Miss Lily as his wards…this was his spot.”
Philip nodded. Emily and Lily were Gina’s adopted sisters of sorts, the first wards of Frederick. Lily had gone on to marry and move out of the country, but Emily and her boy were still a regular part of their lives.
“How old is Gramps then?” Philip asked Gina as he sat down.
“He’s in his sixties, I think?” Lisa queried.
“He’s seventy-four,” Gina replied as she watched Lisa settle Philip into his seat. “Was born three years before the war.”
“And he got me connected with Doctor Mosley,” Lisa added proudly, leaning next to Philip. “Which means you and your family get an eighty percent discount every time you eat here.”
Philip blinked in surprise as he nodded shyly.
“It’s the food that brings us here every time, Lisa,” Gina replied.
“Of course, Miss Gina. What can I get you two then? We have a fine sailfish that got delivered twelve minutes ago and a 4’43” vintage RRose Hoxwine.”
“Oh, no alcohol, sadly. The ’43 vintage sounds divine,” Gina handed Philip the menu. “I’ve taken a lactation pill earlier, and I don’t want Philip getting drunk off of me.”
Lisa laughed as Philip looked absolutely mortified at Gina saying that part out loud. “Hey! That’s… private.”
“Oh, hardly, dear,” Lisa reassured the boy. “I’ve got a tiny munchkin around 220, and he still gets my milk every other day. Safest way to pass on the age-pausing medications.”
“See? “It’s not just to humiliate you,” Gina explained to the boy. “Well, he gets it usually when he’s spanked, so Philip still sees it as part of his punishment.”
“Can we just eat? Too much information,” Philip complained cutely. “I’ll have a chicken parm.”
“And I’ll have two rib eyes and a sailfish,” Gina ordered. “And some of your special truffle fries from the side for us both.”
“As you wish, Miss. Would you like a bottle of wine to go then? Once the young master is tuckered out,” Lisa offered.
“That would be lovely,” Gina smiled as she left, turning her attention to Philip. Gramps got her a special appointment with Dr. Mosley; his treatments range in the millions. How old do you think she is?”
“Twenty…wait, she remembers you getting your butt melted in her late thirties?” Philip enjoyed the momentary displeasure on her face as he mentioned her getting beaten by Frederick.
“She’s in her mid-fifties,” Gina replied. “She’s married to the owner of the restaurant. It’s primarily catering to families who have got their lifespans extended, like with Gramps and us.”
“So kooky are people who are medieval when it comes to whipping sweet, innocent cuties like me.”
“Philip, mind your lip,” Gina warned.
“Well, you do,” Philip said, playfully sticking his tongue out. “And Robbie says the same about Aunt Emily.”
Gina’s lip thinned at the comment. “Well, your cousin is a pest. If anything, Emi is too soft on him. If you start behaving like Robbie, chasing girls all around the city, you won’t be sitting down till you’re thirty.”
“I’m not going to be staying with you till I’m thirty, am I?” Philip frowned.
“Who knows? Dad wants to retire and have you and Robbie start looking after the businesses. And the government is debating changing the age where boys would be emancipated to thirty owing to the increase in average lifespans.” Gina sipped from her glass of water as she eyed his annoyance.
“That’s not fair! “You’ll still not be an adult under those rules; you’re just twenty-six!” Philip complained.
Gina laughed. “It’ll mostly affect those who get their aging slowed, like you and Robbie from nursing,” she explained. “Mommy’s milk does more than heal up your sore buns; it keeps you from growing older. You will be able to live up to a hundred and seventy odd.”
Philip listened to her. She had explained it to him before, but it was still new to him, having grown up in the outskirts of the city without any technology or fancy medicines. “So I won’t look like an old man? Wait, does it mean you will still look like this?”
“I probably won’t look older till around eighty,” Gina replied as the food was brought over by Lisa.
“Well, that’s good. I don’t want my Mommy to look like an old hag,” Philip teased.
“Somebody seems quite smitten by his mommy,” Lisa chuckled.
“He can be a charmer if he tries really hard.” Gina smiled fondly at the lad.
Philip blushed for a moment before he noticed the mountain of food Gina ordered. “That’s too much! I take it back; you will look like a big fat pig if you eat all of that!”
“Oh hush, your mommy has taken lactation pills. That just goes to her breasts for a day for you to drain,” Lisa chided him.
“Eat, baby,” Gina smiled as she began to work her way through the steaks. “Oh, it’s incredible, Lisa! Please give my compliments to your boys.”
“Of course, they’ll be thrilled to hear it,” Lisa beamed and walked off, letting the two eat.
“It’s seriously good!” Philip gushed.
“Lisa’s boys are the chefs; she took them in from your old village thirty years ago,” Gina explained. “We can take the leftovers—”
Her words were interrupted by a sharp smack from behind. Both Philip and Gina turned around – a beautiful blonde girl in her early twenties was bent across their table and a handsome man was in the process of peeling her panties down. Lisa quickly made her way over with a thin cane.
Philip watched on with his cheeks flushing as the cane was tapped against her rear.
“What did she do to earn a public whipping?” Gina wondered as the first stroke fell.
“One, Daddy! I’m sorry for sucking cock!” The blonde yelled out.
“That answers the question,” Gina laughed.
“Does… she have a butt plug?” Philip asked Gina urgently. Gina noticed a small, uneven protrusion in the girl’s rear hole as she was struck again.
“That’s ginger. Lisa must’ve gotten it before the punishment.” “Used to hate those!” Gina reminisced, leaning over to cut and slice Philip’s chicken as she fed him. The rest of the restaurant was halfway paying attention to the caning while continuing to eat, as if this were a regular occurrence.
For the more sheltered Philip, it was still relatively new. It had been mostly his private tutors at her dad’s place with his cousin and the more conservative parts of town where public discipline wasn’t as prevalent. He did see his cousin get his ass blistered by his aunt, but that was family. This was a beautiful young lady getting her skin tattooed, counting the strokes, and confessing how she sucked off a friend’s dick in the middle of a famous restaurant.
“I used to get plenty of this.” Gina stroked his cheek with her thumb as the twelfth stroke was delivered. She sensed he was both getting aroused and flustered by this exchange. “It’s normal here. Most of the patrons here either used to be boys and girls like you or have one.”
“It’s a bit…” Philip looked away as the girl’s daddy picked her up and held her. “I’m not going to be spanked like this here, right? Like…there’s a room inside for you to take me, like at the mall.”
“I…well, it’s perfectly normal for me to tan your hide on the spot if I wanted to. Though you don’t want to be smacked like this?” Gina questioned.
“In private, please,” Philip replied softly. His eyes went all around the room after that, seeing if there were others who could get spanked. One girl seemed to be sniffling and adjusting her skirt. He had gotten an erection that was quite visible, and he hoped they wouldn’t leave soon.
“Alright, darling. Though I must say, you have been a very pleasant date so far.” Gina leaned in to kiss his cheek.
“I have?” Philip blinked. “But I haven’t done anything big or said anything clever.”
Gina laughed out loud at the lad’s words. “Is that what you think you need to do to impress a woman, darling?”
“Well…yeah, that’s what they do in the movies,” Philip pouted, sensing she was teasing him. He looked away, back to the woman, to see her now in her caretaker’s arms as he massaged her striped rump.
“Oh, I have so much to teach you,” Gina smiled. Lisa made her way over with her bright smile and a small bag.
“Your wine and a small dessert for the young master if he fancies a late-night snack,” Lisa said as she grabbed the leftovers.
“Your special chocolate?” Gina asked.
“Yes, Miss Gina. I put an extra bar in for you. I remember all the times…” Lisa smirked, looking at the squirming, spanked girl. Gina blushed, knowing she meant the years where her daddy would have her on display with a piece of ginger stuck out of her bottom. The chocolate was a special treat at the end.
“I don’t remember seeing them here,” Gina whispered conspiratorially, eyeing the two.
Lisa leaned in. “That’s Mr. Honn and his girl Beatrix. They’re regulars. Mr. Honn moved back into the city a couple of years ago; he works in shipping.”
“And his girl?” Gina asked.
“She’s twenty-one, maybe a little older than your young master over here,” Lisa hummed. “Though she might be perfect for Miss Emily’s boy. She is a little… adventurous though, as you have heard.”
“Robin is the same; Emily has her hands full with him. And I had him in mind; Philip is still not fully trained yet.” Gina eyed him with a smile.
“Are you two talking about setting me up with a date?” Philip scowled.
“Well, it’s natural for boys and girls in the middle years to be on dates supervised by their caretakers, dear,” Lisa explained.
“When you are over twenty-one,” Gina added. “Not before. You are still a baby; you have much to learn.”
He frowned, not sure what to think as Lisa went to pack the leftovers and Gina paid for the meal. He made his way out to the parking lot, looking around. The city was beautiful at night; he wished Gina would let him explore more! His cousin got to be more independent in his twenties; that was still a while away for him.
“How was dinner?” He heard Gina’s voice from behind.
“I want to drive back,” Philip declared.
Gina shook her head, grabbing the keys, and got into the car. “Oh no. You have a painful discussion waiting back home in my room. A proper debriefing, so to speak.”
Philip gulped. He got in, looking at Gina nervously. Her breasts were now distressingly close to spilling out. She looked especially beautiful. Mommy always looked beautiful when she was going to punish him.
He waited behind as they got home, picking up the take-home bag as he let her walk in front.
“What did I say about walking behind me?” She asked sharply as they got to their door.
“Not to,” he hung his head submissively as he moved closer. He felt her cup his chin, lifting it up. Her light eyes twinkled as she leaned in for a quick peck on his lips.
“Thank you for a wonderful date, my love,” Gina beamed. “Now, why don’t you go to my room and get comfortable?”
“Comfortable? You’re going to whip me!” Philip complained, blushing pink at the unexpected kiss.
“Hmm? Most boys would be thrilled to be invited into a girl’s bedroom on a first date to be half naked,” she winked, quickly swatting his butt. “Now go on.”
He gave a small, annoyed huff and made his way over. Unbuckling and putting away the belt, knowing she was going to use it on him. Philip was only summoned to Gina’s bedroom for punishments, and half the time she wore him out to the point he’d sleep in her bed. He looked around the expensive bedroom, eyes deliberately avoiding the armless spanking chair in the middle as he heard her footsteps.
He tensed as she opened the door. Gina was a lot scarier; now she was all business. “On your feet, take your shoes off, young man. Hands on top of your head.”
“Yes, Mommy,” Philip settled into his submissive state, taking off his socks and shoes and putting them away as Gina entered her walk-in wardrobe. He heard her rummaging around as he stood in position with his hands on his head.
As she got out, Philip saw she had her gym shorts on and an open robe. In her hand were her small light paddle and a small bottle of oil. Her breasts were open and swaying as she walked over, settling by the side of the bed. Philip obediently moved next to her, eyes drifting between her bare breasts and the paddle. It was less painful than the thick hairbrush she used when she was mad.
“Most of the dates I’ve gone on with your Gramps end with me with every inch of my bottom on fire. So does Robby with Aunt Emily,” Gina whispered as she unhooked his pants and underwear and slid them down his legs.
“That’s not helpful information,” Philip complained. Gina giggled, bending the teen across her long legs, his torso on the bed.
“What I meant was… it’s normal, expected for you to be spending a lot of hours over Mommy’s lap,” she cooed, uncorking the bottle as she poured the oil across his fleshy nether cheeks. “This is where boys learn best.”
He felt her soft hands massage the oil into his rump. Slightly playing with his crack, her index finger gently tracing the insides as it feathered over his bottom hole. He shivered, remembering the girl with the ginger inside her hole. “Not there,” he whispered.
“Not your booty hole?” Gina teased. “Relax, you haven’t done anything to earn a punishment there.” Gina quickly spanked him, six smacks on alternating cheeks. He let out soft yelps, his natural pride taking over, and trying to be as quiet as possible.
“That doesn’t mean it’s off limits. Every inch of your backside is mine to punish. Just like your cousin, just like that girl you saw,” she peppered his flesh with a dozen more spanks before grabbing the paddle.
“I’m going to give you thirty with the paddle,” Gina explained, tapping the wood against his buttocks. “This is for failure to dress properly. When I say we are going out in public, I expect you to be presentable. No hoodies, no dirty clothes, no sweatpants. You will wear the nice clothes that I’ve picked for you. Is that clear?”
“Yes, Mommy,” Philip reached for a pillow, burying his face into it so he wouldn’t make any noise. He soon felt the sharp sting of the paddle, his cry muffled by the pillow. Gina always spanked hard; she always wanted tears before she was done. He took the slow, methodical paddling with as much grace as he could muster, wiggling around her thighs as he slowly counted down the smacks.
“Twenty-nine…thirty!” Gina lovingly played with his hair, leaning over to flip him to his back. “Good boy. I’ll let you nurse for a bit before we get the belt, okay?”
He nodded. Gina had the most amazing breasts he had ever seen on a woman. Firm yet impressively round and taut with small, sensitive nipples. His cousin had told him the women could cum from him nursing, and Philip had gotten Gina to moan the last time.
He adjusted so he was lying on her side as he pressed into her. Philip leaned into her warm bosom, his mouth enveloping the pink nub as she reached around his back, rubbing his paddled rear.
“Now, we need to address your driving. I can’t believe how reckless you are! A proper gentleman would…mmmm…” Gina was distracted by his tongue flicking across her nipple as he held her. The warm intimacy and the rhythmic suction slowly stimulated her. “Good boy, my sweet darling boy.”
“I’m a good boy for driving recklessly?” Philip felt the urge to be cocky… which unfortunately caused Gina’s eyes to sharpen. She squeezed his ass cheek painfully.
“You’re being awfully cheeky for a boy who is due a long talk with Mommy’s belt,” Gina warned as he yelped and buried his face into her skin, renewing his suckling vigorously.
Gina relaxed, her index finger again tracing the ring of his bottom hole to get a nervous shiver from Philip. Even his cousin Robby would get awfully quiet whenever Aunt Emily threatened to take him to her bedroom for some ‘special’ punishment. The last time when the two got disciplined together by Emily and Gina, Philip was sent to get the paddles from Emily’s punishment cabinet, and he had seen a strapon harness and a medium-sized purple dildo tucked behind.
“Aunty Emily is very strict with Robby if he puts his life in danger. Perhaps I should start holding you to the same standards,” Gina hummed, lovingly kissing his cheek.
“I’m sorry, Ma’am. I’ll take my whipping,” Philip replied, unlatching from her left breast. He leaned to kiss her on the lip, letting Gina taste her milk.
“Hmm? Now?” Gina asked. “Alright then, baby, maybe it’s best to get it over with.”
She stood up, stacking two pillows in the middle while he held onto the stress pillow, one he liked to cry into. “Do you think you can take fifty strokes?”
“No, Mommy, that’s too much!” Philip protested. “You have already paddled me!”
“Alright, twenty then. Your endurance will increase the more you have my milk.” Gina doubled the belt. He could take about three dozen, but his bottom seemed sore already. She gave his licks slowly, letting him feel each stripe as he kicked his feet and cried into the pillow. Going up and down his buttocks and covering every inch in bright, glowing red from the oil.
When she was done, Gina scooped him up again. Philip had been completely worn out by this point, the boy gratefully latching onto her breast as he nursed. “I’d call this a successful first date. Not many boys can say they get to sleep with their girl.”
Philip smiled weakly. Their relationship was quite unconventional, but he couldn’t help but enjoy this.
