Being a single mother to a teenage boy isn’t easy, thought Allison Armstrong as she quickly finished up her emails before leaving her office. She looked up at the clock. It was three in the afternoon on a Friday. The brunette flipped her hair back and adjusted her jacket one final time before heading to her car. “See you on Monday,” she waved at her secretary.
“Bye, Miss Allison,” Her secretary, Annie, grinned back. “Are you going on any date this weekend, or is Ray Ray keeping you busy?”
The thirty-year-old executive sighed. Ray wasn’t her biological son. She had adopted him a few years ago after a bad breakup. It wasn’t the sanest of decisions, taking in a young, troubled older teen when she was still in her mid-twenties and struggling with getting her business off the ground. But she had no regrets. Ray had been her rock. He gave her a sense of purpose and responsibility she did not have till then as an adult.
An orphan herself with a big inheritance, she had been on a downward spiral for most of her life. Her model looks meant she had all sorts of men lining up to be with her. But Ray was the one who made her settle down.
“You know how things are with that little troublemaker, Annie,” Allison sighed at her twenty-one-year-old secretary. Annie occasionally babysat Ray when she had to go out of state for meetings. “Besides, it’s a Friday,” Allison added.
Fridays were the day of discipline in their country. Corporal punishment was a normal part of a teen’s upbringing, especially as they grew older.
“Ray had a rough week?” Annie smirked. She knew her boss had been busy for the past month with her big meeting, so she wouldn’t have been able to pay enough attention to the lad.
“Yeah. We had the Jeffersons project, so I couldn’t really deal with him all month. I had a long talk with him this morning to expect two days of spanking for all the mischief he had done! And the little brat skipped school on Wednesday to go to that new Emily Holt movie with his friends to add to everything,” Allison huffed.
“Emily Holt? The actress who looks like you?” Annie teased. “You know that’s a very erotic movie where she gets whipped all the time?”
“Maybe my young man’s projecting. Better make the lesson memorable,” Allison grinned. Spankings were one part of their life that Allison enjoyed. It provided a level of physical intimacy one normally didn’t get from an older boy. Indeed, their culture regarded the age of maturity at 23, which meant Annie herself was subjected to spankings from her mom and dad.
“Mmm…” Annie squirmed wistfully.
“Anything wrong, dear? Don’t tell me you are due one later today?” Allison smiled at her secretary. She seemed squirmy today, shifting in her seat.
“Yeah, I’m on restriction… had a beer with Philip yesterday,” Annie confessed. Philip was her boyfriend, who was twenty-three and allowed to drink while she wasn’t. “Mommy gave me a sharp strapping when I got home, but Daddy won’t be back till tonight,” Her blush grew as she spoke. The rule was that if one got spanked by one parent, then they also got it from the other. Restriction also meant taking her adult privileges away, with Annie only allowed to work and having to head straight back home.
“You are lucky to have both your mommy and daddy and Philip still in your life, Hon,” Allison replied with a warm smile. It was cute seeing how Mom and Dad became “Mommy” and “Daddy” when faced with a trip across their knee, even with a mature twenty-one-year-old like Annie. With Ray, she was Miss Allison or Mom on most days, but over the weekends, she became Mommy the moment she stepped into her home.
Annie returned the smile. “If you want to go get a drink on Sunday, I can look after Ray. I’m going to be sore tomorrow, but the restriction is lifted tomorrow.”
“Oh, hush. I’m not going to have my assistant waste her weekend babysitting. You would need a day off, especially after running around all month,” Allison added as she headed out to her car.
She was tempted by the offer, though. Allison had been working all month long on the project, so she could use a break. Annie was good with Ray, though her boy was a charmer who did get her assistant to indulge in his whims. Annie did not like to spank Ray even though Allison had given her permission.
But then again, discipline was seen primarily as a mother’s job in their country. It was an old-fashioned culture where physical discipline was a big part of their religious affairs, and spankings were very much mainstream. Her car passed by a store that sold disciplining tools for older teens and young adults. Allison looked over briefly, mentally thinking about how to go about today’s lesson.
As she got near her suburban home, she decided on a good whipping with her belt. The protocol was one spanking by both sets of parents, so with Allison being a single mom, she always gave him two sessions for each offence. Ray hated that but knew it was fair for him. He’d rather take it from his beautiful adopted mommy than have a man in his life smacking his butt.
Allison slowed her car in the garage and got out. She could hear that the TV was on. It stopped when she opened the door, and her heels clip-clopped across the hardwood floors of her big mansion. She made her way up to the living room, where her handsome young charge peered from behind the sofa.
“Heya, Miss Allison!” Ray beamed brightly. He was quite handsome these days with auburn hair and big oval glasses, wearing just a white t-shirt and black shorts.
“Home early, kitten?” Allison asked fondly as she put away her briefcase.
“The athletics team got caught doing acid,” Ray said enthusiastically, hoping to impress upon his adopted mom how the rest of his peers were even worse than him. “Miss Fell had to whoop them all, so she let us off two hours early.”
“What?” Allison gasped in shock.
“Miss Fell was livid! She got the senior cane out for it!” The boy added as his eyes followed her heaving bosom, almost mesmerised. He found Allison to be very attractive, especially when she wore her office outfit, which displayed her cleavage.
“Your school is the worst in the state!” Allison rolled her eyes. “And to think how much money I’m paying. I’m seriously considering taking you out and enrolling you somewhere else! You’d think an elite private school would have more civilised students!”
She walked over toward him. Ray nodded, “Aren’t you glad I’m not with the bad influence kids?” he gloated. Ray had grown up in an impoverished area and used to run with thugs and gang members. The ‘undesirables’ in Allison’s eyes. It was why Allison had him enrolled in the posh school, which he hated.
“Those brats are acting this way because of how pampered they are,” Allison countered. “Mommy and daddy are too rich and let them get away with murder. That doesn’t happen with you, does it?”
Ray looked up at her with a small gulp. “I don’t act that way. I’m not even friends with them. “Well, except Tilly, but she’s from your side.”
“Tilly was part of the group?” Allison raised her brow. Tilly was one of her best friend’s daughter.
“She said she didn’t do it,” Ray responded as Allison sat next to him. The boy leaned in, taking in her scent as he felt her toned form underneath her jacket. Ray was still smaller compared to Allison from his childhood malnutrition, and he was not the active type compared to his mother, who worked out every morning and kept her cheerleader frame.
Allison instinctively wrapped around the lad. The one big side effect of regular discipline was the intimacy and aftercare. Ray was much more physically affectionate with her than a teenage boy would be with his mother, and Allison liked to let him experience what he missed out on when he was younger.
“Jakob would be taking Tilly out to the woodshed right now,” She ran her fingers through his hair.
Ray momentarily fantasised about the sight. Her perky young butt bent over in her daddy’s woodshed, her crying with each lick. He did get to see Tilly’s butt for a split second today when he passed through the punishment room at the back when she was bent over for the cane. He had also seen her spanked bottom a few times when he visited them.
“Though it’s not Tilly you should be concerned about now, kitty cat,” Allison whispered into his ear, her palm drifting to his ass cheeks.
Ray groaned, “Was hoping you’d forget that.”
“Nope,” Allison chuckled.
“Do we have to do it…like now?” He pressed closer to her, slowly rubbing his nose against her cheek.
Allison let out a soft purr. He was so cute when he was trying to wiggle out of trouble. “We can have some comfort after you take your licks like a man,” She swatted his bum. “Now go. My room. Just your undies.”
Ray sighed, almost dramatically. “You know…it isn’t fair to make me take a man’s punishment and still treat me like a boy, Miss Allison,” He complained as he walked away towards her room.
Allison chuckled at his comment. He had certainly grown up, she understood. Ray had always been trying to act older than he was, so with her, it was Allison trying to teach him the opposite, to indulge more of his cuddly side with her. To let her take care of him and pamper him.
Though she had to admit, Ray wasn’t the young teen he was when she took him in. As she walked towards her kitchen, she smiled, reminding herself of why he was in trouble. She poured herself a glass of white wine and slowly moved to her room, giving him enough time to strip to just his white briefs. His body had grown; his previously skinny frame was now filled out, with his bottom nice and plump.
Ray heard her walk into the room. He listened to her footsteps as she went over towards the cabinet, humming. He took a deep breath as he heard the rustling of her jacket, getting comfortable.
“What was the movie you wanted to see so badly that you skipped classes?” Allison asked him. Ray turned deep red.
“The…Logan Wilson movie.”
“Logan Wilson is just the supporting character in Sinful Maladies,” Allison retorted.
Ray didn’t turn around, not wanting her to see his face. The movie his friends wanted to see was an erotic thriller with Emily Holt, the new sex siren who kind of looked like a younger version of Allison. There was a scene in the movie where Emily takes a hard paddling when she was in college, and part of Ray was wondering how Allison would’ve looked in that position.
Her palm softly squeezed the boy’s buttocks, which got him to focus back on his predicament. “Turn around,” Her voice commanded.
Ray slowly turned, face reddening as he realised Allison had slipped off her shirt, leaving her in just her sheer black bra and work pants.
“It seems my little boy isn’t as little anymore,” Allison scolded, eyes flicking down to his crotch to see him slowly getting hard. “So I am going to have to make this a thorough lesson. Take off my belt.”
Ray felt a chill. He looked down at her black leather work belt. He had felt the sting of the belt more than a few times, often in her office if he got into trouble and she had to get him. His fingers went to unhook and slowly pull the supple leather strap off, trying to avoid looking at her breasts with her soft cleavage inches from his face.
“Here, Mommy,” Ray whispered submissively as he handed the belt over. When he was younger, he’d have fought back, but that usually meant a harder lesson. He learned very quickly that it was better to take his licks so he could get to the good parts after.
Allison smiled when he called her Mommy. “I have been neglecting your bottom all month. But that ends now. You have my full attention for the week, kitty cat,” She pulled him by his wrists, leading him to the bed, and stacked two pillows.
“Bend over,” She ordered, wrapping the belt around her palm.
Ray complied, his bottom quivering, his underwear barely providing any protection. Especially with how fit Allison was. The boy turned his head to look at her. Admiring her breasts as she raised the belt up high.
Crack!
The leather bit into the lad’s rump, earning a sharp gasp as he buried his face into the bed. “One, thank you, Mommy,” Ray counted.
Crack!
“Two, thank you, Mommy,” Ray knew the routine. Not counting meant Allison would repeat the stroke.
“Was seeing Emily Holt naked worth this, Ray?” Allison asked with an extra hard lash, her chest bouncing as she put her back into the stroke.
“Yeoww! Three, thank you, Mommy…Yeah!” He wiggled his ass.
“Yeah?” Allison smiled as she gave the fourth stroke, listening to him count. She moved over to her wine glass to take a sip, admiring the lines forming on his cute bottom. “What lewd thing did she do to have it be worth my belt?” She asked with three hard lashes.
Ray counted each stroke, his butt sizzling as she slowly pulled his underwear down to expose his arse to the cool air. “She gets whipped a lot…and she looks like you sometimes…”
Allison raised her brow. “So you were fantasising that it was me getting it in the movie?”
Crack!
“Oww! Seven, thank you, Mommy!” The lad turned around, eyes moist as he focused on her beautiful body, her heaving chest. “Maybe…” Roy said with an impish grin.
“I see…” Allison sipped her wine before putting the glass down. “We need a good long lesson then.” She slowly began working the belt down his flesh, each lick biting into his round orbs, leaving a nice red stripe. The thirty-year-old made sure the boy counted each lash. Around five strokes, she would take another sip of her wine so he had a small break. The clock slowly ticked on, the room filled with Ray’s cries and obedient counting.
“Thirty-six, thank you, Mommy!” He hiccuped.
Allison paused, putting the belt away. “This is a break; we aren’t done. You’ll get the next part at bedtime,” She flipped the lad around, smirking as she looked at his crotch. He had ejaculated in the middle of the lesson at some point.
“Go clean up, kitten. And no clothes for the rest of the day,” She leaned to kiss his cheek and let him up. Ray blushed at her words as he stood up, awkwardly walking over to her bathroom.
“Can’t I keep my T-shirt on, Ma’am?” he asked. He hated it if she had friends over and he had to be nude.
“You know the rules, darling – no clothes for naughty boys and girls who get spanked on a weekend,” Allison reminded him, watching him get into the bathroom. She took the time to get rid of the soiled pillowcases.
Ray took a shower before drying himself, his backside on fire. He looked at himself in the mirror, his body now a bit fuller instead of the skinny frame from years before. His bottom was red and swollen, almost shiny like an apple.
Rah walked out of the bathroom, letting out an audible gasp as he saw Allison had taken her pants off, leaving her in just her revealing bra and panties. Her bottom was turned to his side as she fixed the bed, the pale muscular orbs a complete contrast from his own well-whipped flesh. She looked over when he gasped.
“You’re not a little boy anymore, Ray – so it’s time for me to start training you to be less… excited… to be around women and see us as just sex objects,” Allison informed the lad. “Which means starting today, you’ll be seeing a lot of me like this.”
Ray blushed and nodded as he approached her. It was something he knew happened. A lot of his friends were under this aversion therapy, designed to get them to be more comfortable around women. With the girls regularly spanked and often kept nude, often in public, a lot of the times the boys ended up getting erections or losing control. The women in the family were in charge of re-educating them or often hired specialist disciplinarians if they didn’t want to deal with sexual matters with their boys.
Allison, though, did not find it taboo. She knew she’d be dealing with this with Ray when she adopted him. It was a different dynamic between them too, with Allison younger and way more attractive than the other mothers. She sat on the bed and pulled him into her lap for a warm cuddle. She placed gentle kisses on his cheek as she softly massaged his buttocks.
“You may not be a kid anymore, Ray. But you still are my boy till you turn twenty-three.”
Ray smiled, face mushed into her chest. Breasts were seen as the symbol of motherhood in their culture, something not considered as sexual. Allison let him see it as his warm safe space; she hummed as he rested on her bosom. It was common for boys and girls to suckle on them as they got older, a reminder of her maternal position.
“I…did kinda think of you with the movie. Emily Holt looks like a young you,” He whispered. He paused, considering his words. “I don’t know if thinking that way is wrong.”
“It’s important to get any troublesome thoughts out of your system, Kitty Cat,” Allison smiled. “And I don’t mind. You are a boy of age now, and it is normal for boys and girls to feel this way about sex and spankings sometimes. What I do not approve of is skipping classes. You will take your licks for that.”
“I thought I did take them well,” Ray countered, lips parting expectantly. “And you said comfort after.”
Allison laughed. “Such a cheeky boy,” she hummed, slowly taking her bra off. He blushed. This was his new favourite part about getting spanked, the old traditional way of maternal comfort.
“This is just a small one; you still have the rest of your whipping at bedtime,” She watched his eyes go wide as he was slowly guided to them. “Give them each a small kiss. You may suckle for a few minutes, but afterwards it’s time for you to go finish up your chores.”
Ray seemed mesmerised as he slowly latched on. His mouth suckling her small pebbled nipple. His friends and even Annie got to do this, but they didn’t have the perfect breasts Allison had, nice and firm and youthful.
“Good boy, come on now,” She kissed and hummed, letting him have a few more minutes before she had the reluctant boy disengage. “Chores,” she said again. “We can have a special night on Mommy’s breast after I finish with your whipping.”
She got up, pulling her bra back on.
For Ray, the rest of his day was a daze as he did his chores fully naked. Allison applied some quick healing cream on his buttocks so they’d be ready for round two, but they still ached. Allison also walked around in very revealing underwear, her fitness model physique and toned buttocks presented, which he couldn’t look away from. The few minutes with her are still in his mind: the closeness and her shape as she bent to get the wok as she cooked. There was something sensual about how Allison glided around the kitchen making their dinner. And for the boy, it was a bit too much stimulation.
“Ray, why are you rubbing your penis?” Allison’s sharp voice cracked through the air like a whip.
Ray yipped, not realising what he was doing. He looked down, his hand on his shaft almost by its own power.
“It was an accident! I wasn’t thinking!” He gasped truthfully. His eyes could see the annoyance in her eyes.
“Touch yourself again and I’ll march your butt to the garden and wear you out with the switches!” She walked over to bend him across the dining table. “Maybe that will teach you, having the neighbours see how you act.”
She began peppering his arse with a dozen crisp slaps. Ray yelped softly with each blow on his tender strapped backside.
“I’m sorry!” He begged with a shiver as he felt her palm replaced by the thick wood of her spatula. “Mommy, not the spoon, yeoow!” His cries filled the kitchen as Allison delivered ten spanks, her tennis form translating into making each blow a bolt of pain for the teen.
“Up, get the plates out,” Allison ordered, pausing to gently hug and kiss Ray’s cheek. “And no touching your willy.”
Ray was subdued for the rest of the night. Eating his dinner in silence, not making much small talk even though Allison tried. The lad realised by the end, however, that she didn’t seem angry.
“Am I not in trouble for touching myself, Miss Allison?” He asked her gently as he cleaned the plates.
Allison looked at him. “I told you. It’s not out of the norm for a boy your age to have sexual thoughts,” She leaned to slowly ruffle his hair.
“Even with…like…seeing you?”
“Does it bother you, dear?” Allison questioned. “Spankings and our special aftercare are… intimate acts; a lot of women find it hard to go through with it with older boys and girls. I can have a professional disciplinarian come deal with your punishments if you don’t want me to spank you. Amanda is the one who deals with a couple of friends; I can get her if you’d like.”
“What?” He shook his head. “No! Like… I trust you…” He looked at her with doe eyes. “I don’t want anyone else.”
He knew of Miss Amanda Rock, who was on call whenever his friends needed to be punished.
“Good,” Allison nodded. “If you’re done, you can go wait for me in your room for the final part of your whipping. Tomorrow we will deal with all the other mischief you had gotten into over the past month when I wasn’t around.”
Ray gulped but nodded. She had explained it to him earlier before she left for work. He walked over to his bedroom, checking his arse in the mirror. The healing cream was quite potent, working deep into his muscles, so his bottom was just nice and pink from her use of the spatula.
He went to his phone, texting his friends. He knew that most of them would be in the middle of their Friday punishments. Justin was the only one who responded, Tilly’s brother, who told him how their mom and dad took the girl to the woodshed after learning she was taking drugs. Justin was especially gossipy, telling him how his twin sister confessed and how mad their mother was.
He was so engrossed in his chat that he didn’t hear Allison come in. She had taken a shower and just had on her panties and a black silk robe, the belt in her hand.
“Ray,” she called out. Ray turned around, blushing as he put his phone down.
“Was talking to Justin about Tilly.”
“I called Sabrina,” Allison smiled. “She and Viktor are livid. Tilly is probably going to be sore for a couple of weeks.”
Ray nodded, eyeing the belt. “But not me, right?”
“Oh, you’re…well, not an angel, but I am impressed by your judgement in this regard. I remember you telling me about that group being trouble at the start of your school year.”
Ray moved so she could sit by his side. “They seemed…off. They acted like they owned the place. I didn’t vibe with them at all.”
He looked at Allison, hesitating. “So…like…Tilly. What’s going to happen to her?” He knew Allison would have the juicy details from Miss Sabrina, Tilly’s mom. Perhaps he’d even be allowed to go watch her punishment if they felt a public lesson would be beneficial. It wasn’t unusual for the women to punish the boys in front of each other.
“Tilly is under holy restriction. She’d be serving at the temple every day after school for a while,” Allison explained. “Sabrina has decided Tilly was acting too big for her birches, so sadly for her, she won’t be wearing any for the next few weeks.”
Ray’s eyes widened. “Even in public? Like at school?”
“Oh yes. And you will endure the same fate if I find you are doing drugs or smoking or drinking before you turn twenty-three,” Allison warned.
“What? Mommy, come on. “Drinking is fine, right? Not right now, obviously, but like…when I’m eighteen,” Ray added quickly, seeing her expression change.
“Ray, if I find out you were drinking before you are fully emancipated, you’ll spend a whole month on my tit like a baby.”
Ray blushed at the words. Which wasn’t all that bad in his eyes as he looked at her cleavage. They had lactation pills which were used at the temple of the mother goddess. Allison had nursed Ray a couple of times after he turned sixteen as part of their religious rituals. It was seen as a method for humiliation and punishment, especially with those in their early twenties, but Ray enjoyed the few times he was allowed to suckle her breasts, something which was still new for the lad.
“Okay,” he said submissively.
“Hmmm. Perhaps you could use a day of restriction tomorrow. Going to watch a movie like that is definitely grounds for reminding you of your place.”
Ray looked at her; her lips curled up in a slight grin. He’d enjoy that. “Would there be anyone around to see it?” He had seen Annie be made to suckle on her mother’s breast with her red arse cheeks on display; that was definitely embarrassing for his mother’s secretary, letting Ray see her in that state.
“Perhaps we can visit Sabrina and Tilly, and you can compare which mommy’s milk is better,” Allison seemed to be in a better mood right now.
Ray smiled, leaning close to her. “Just us two. And no belt now if you are going to punish me again for the same thing.”
“Hmmm,” Allison wrapped around him, letting her robe slip open as he was pulled into her lap. “You know that you get a double dose of the belt – if I had a husband, you would be getting one from your daddy too.”
“And you already gave me a belt whipping from daddy’s perspective. Mommies are meant to be nicer,” His palm gently cupped her breasts, giving gentle butterfly kisses on them.
“Mmmm… So putting you in restriction is Mommy’s punishment?” She teased. “Perhaps…fine, I’ll indulge a little.”
She kissed his cheek. “You will spend the whole day tomorrow on my breasts. No other food. And you will be spending the day naked. You will also be given two spankings as a general punishment for every act of mischief I wasn’t around for this month.”
“Deal!” Ray replied quickly. He wasn’t the most behaved when she wasn’t around, and this was a “get out of jail free” card, which Allison didn’t usually allow.
“That was a bit too fast,” Allison frowned. “You weren’t staying up past midnight playing video games with your friends when I wasn’t around, were you?”
“I’ll take the punishment and won’t incriminate myself any further,” Ray grinned back.
Allison bit her cheek. “Fine. Though I said no belt, I didn’t say no spanking now,” She quickly flipped the boy over to his stomach, across her bare thighs.
“What?” Ray frowned, realising he had been conned in his haste. “Just your hand then?”
Allison rubbed his back. “Alright, dear. No need to count then,” The spanking with the spatula and the belt had already left him nice and sore, so she wasn’t going to whip him hard anyway. Her palm raised up high, slapping his left cheek and then his right.
“Mommy’s boy needs a firm hand to keep you in line,” She scolded him lovingly as she smacked, her breasts swaying vigorously with each slap. They’d be bigger in size tomorrow once she had her lactation pills. Allison smiled, remembering how Ray was so mesmerised by them the first time she told him he got to suckle as part of their rituals. Ray yelped as he tried to keep his composure, not wanting to give her the satisfaction of getting him to cry with just her hand.
As time went on, Ray got more and more animated before the seventh minute, when his cries were loud enough. Allison gave a final set to his thighs before letting him up. Letting the boy latch on to her nipple once more. “Go on, baby.”
He softly suckled, eyes moist as he watched the beautiful woman who had taken him in.
Allison ran her fingers through his mop of hair. “Such a sweet thing. You will always be Mommy’s boy.”
