Pete, twenty years old, needed a haircut but was tired of the same old generic cut he got at the local barbershop. He searched online for an alternate option instead. 

He found a listing of personal ads for hair cutting services, and his eyes were drawn to one ad with a headline that said, "Haircuts Available for Good Boys," with a picture featuring a woman holding clippers. 

Her face was turned away from the camera, hidden behind her brown hair. She looked to be in her forties and in good shape. Pete was intrigued by her mysterious posture, accompanied by the curious caption. A hint of excitement emerged from deep within him, and he decided to reach out. 

The day of his appointment finally came. He didn't know why he was feeling so nervous; maybe it was because he was meeting a stranger at her house; maybe it was more than that. She'd been very quick and professional in her online communication, which slightly eased his worries. He spent some extra attention that morning on his appearance, naturally wanting to impress her.

He arrived early and sat in his car, waiting anxiously for the appointment time. At about five 'til, he shook off his nervous energy and knocked on her door. A few seconds later, the door opened, and the woman greeted him enthusiastically. Her eyes were kind and nurturing, and her smile tempered his nervousness. She was wearing a comfortable black shirt with spaghetti straps over her chest, revealing the tops of her breasts. Her pencil skirt ended at the tops of her knees. 

With his excitement building, he followed her inside her small but cozy house. She led him downstairs, where she had a small barber station set up. She had him sit and covered his clothes with an apron. 

"What are we looking to do, sweetie?" she asked as she ran her hand through his long, curly hair. "I love how curly your hair is." 

Pete loved her soft touch and her caring tone. He told her what he usually gets at the barbershop, and she smiled down at him approvingly and got to work. 

They filled the time with small talk. He loved how reassuring and touchy she was. She would often touch his shoulders and hold his head in place as she cut his hair. He felt taken care of in such a nurturing, maternal way that he felt a deep connection with her, even though they had just met. 

She would stand in front of him, holding his face still with her hands, and bend forward to check her work. Pete's eyes were repeatedly drawn to her breasts, which swelled out of her shirt when she leaned over in front of him.

She finished with the clippers and began touching him up expertly with her scissors. As she moved around him and leaned into him, she didn't seem to mind letting her breasts rest against him. He obviously didn't mind either and was acutely aware every time, wanting to just curl up in their warmth. 

She finished up her work and stood behind him with her hands on his shoulders. "You've been such a good boy for me, sweetie," she said, smiling at him in the mirror. Her words and smile sent chills through his body.

"I'm glad you think so, but I'm kinda curious," he said, trailing off hesitantly.

"About what?" she questioned.

"About what happens to the boys who aren't so good for you," he said coyly, gauging her reaction closely. 

She looked down at him with a flash of deviousness. "Well, bad boys get punished in this household," she said salaciously. "I sure hope you've been well behaved lately," she warned teasingly. 

"Well, I try to be a good boy, but I'm not always perfect," he replied, very much enjoying where this was going. 

Her countenance dropped as she feigned disappointment. "Hmm, that's not what I like to hear. Do I need to go get my hairbrush? It's very useful for dealing with naughty boys."

Pete was fully erect at this point from their interaction. "Well, I mean, I was pretty disrespectful to my mom the other day, but other than that, I've been an angel." 

She gasped at his confession playfully. "And did she give you a well-deserved spanking?"

"Well, no, I'm a little old for that. She was a little hurt, and I felt bad, but nothing happened."

"Nonsense. You are not too old to be spanked, only old enough that a spanking over your pants won't be sufficient." 

Pete's eyes got bigger at her words, not out of fear but out of pure thrill. 

She continued, "There's no way I'm allowing you to get away with disrespecting your mother."

"I don't think you should allow that either," he said as he met her eyes with intense thirst. 

That was all she needed to snap into action. She removed the apron carefully, making sure the cut hair didn't spill on him. His boner was revealed, pressing against his khakis along his leg. A dark wet spot had appeared in his pants, where pre-cum had seeped out. She looked at it and back up at him with an equal thirst in her eyes. "Let's go upstairs. You're gonna get it so hard," she threatened. 

She led the way up the stairs as Pete watched her hips sway in her tight skirt. His legs felt like jello as he climbed up after her. He couldn't believe what was about to happen, and a little bit of fear was now creeping in at the thought of the unknown pain that was imminent.

They walked through her house and entered her bedroom. She disappeared into her bathroom and quickly emerged with a hairbrush in hand. She sat down on the edge of her bed and looked up at him expectantly. "Pants down, young man," she ordered.

Pete hesitated. "How much is this going to hurt?" he protested. 

"Oh, it's really going to hurt," she said matter-of-factly, "and you're not getting out of this. Bad boys get spanked. You're going to take your punishment like a good boy, or you will make it worse for yourself. Now take off your pants—your shirt too."

Her blunt tone only excited him further, proving to him that he wanted this no matter how much it was going to hurt. 

"Yes, ma'am," he said as he unbuckled his belt and slid his pants off. He removed his shirt, revealing his toned upper body. She looked him up and down. "You're such a handsome young man," she complimented.

"Thank you, ma'am," Pete said, blushing. 

"Come here, sweetie," she said sweetly as she motioned him forward. He walked forward and stood in front of her with his hard penis poking out through his underwear toward her. 

She smiled up at him and reached up, wrapping her fingers around the band of his underwear. "Do naughty boys get their bare bottoms spanked?" she asked, letting her fingers rest on the inside of his underwear. 

He nodded. 

"And are you a naughty boy?"

"Yes, ma'am."

"That's right," she said as she slowly slid his underwear down his legs, allowing his penis to spring out towards her. As she bent down, lowering his underwear down to his ankles, her face was positioned very close to his penis. She paused in this position and looked up at him, saying, "I'm very impressed at how big you are, young man." Pete beamed proudly as she returned to her upright position.

Maintaining eye contact, she began slowly hiking her skirt up her delicious thighs. Once her thighs were bared, she ordered, "Bend over."

"Yes, ma'am," he replied as he laid his naked body across her bare thighs. Pleasure rushed through his body as his penis pressed into her legs. She guided him into place until his body was fully supported by hers. "You have such a cute bottom," she said as she rubbed it softly. "I'm going to enjoy this." 

She raised her hand and slapped his right cheek hard. The high-pitched sound and the sharp sting were delicious as Pete's body reacted more in pleasure than in pain. She slapped his left cheek even harder, which made Pete moan and arch his bottom in the air for more. 

She indulged him and spanked his bare ass hard and fast with her hand. Pete began grinding himself on her leg in rhythm to her spanks and felt himself getting close to an orgasm. As his moans increased, she noticed this too and stopped spanking him.

"Oh, no, you don't, not yet anyway. Have you forgotten this is supposed to be a punishment?" she said as she picked up the wood-backed hairbrush. 

The first spank stung like hell, and Pete quickly realized this part wasn't going to be quite as pleasurable. The second spank came quickly on the other cheek, followed by another on the same spot as the first. He flinched in pain and let out more of a groan this time. "Hmm, that's a much more appropriate response," she said approvingly. 

She continued spanking his bare bottom all over with the hard hairbrush. Pete took it as well as he could, but as the blows from the unrelenting wood continued, he began moving around on her lap, trying to avoid the harsh spanks. "Where do you think you're going? Good boys stay put for their spankings. Are you a good boy?"

"Yes, ma'am."

"Then stay still." She leaned over him, holding his body tightly to her, as she hit his ass over and over again. The hairbrush was starting to do significant damage as his red cheeks grew darker, especially when she focused the hairbrush on one spot. 

She loved the response she got when she'd spank his sit spot repeatedly. Once again, he could no longer keep himself still. He jerked his body against her grasp. 

"You just earned yourself more, young man," she scolded. 

She put her outside leg over his legs, locked him into place, and began driving the hairbrush down on his ass. His cries grew louder as she pounded his ass repeatedly. 

After making sure his entire ass was deep red, she stopped and rubbed his burning ass gently as he cried softly. "It's ok, honey; we're almost finished. I have a bath brush hanging up in my shower. Please, go get it."

"Yes, ma'am," he sniffled in compliance.

"Good boy," she said approvingly.

He climbed off her lap and retrieved the bath brush. It felt so heavy in his hand, and he knew his throbbing ass was about to be fully blistered. Knowing this, he still submitted to her commands. He handed her the bath brush and awaited her orders with his eyes on the floor. 

"Oh, honey, look at me," she said sympathetically. He looked up at her. She continued, "I know it hurts, but you need to learn not to disrespect mommy, or really any other woman in your life. Do you know what the wheelbarrow position is?"

He nodded.

"Please get in position."

Compliantly, he turned around, put his hands on the floor, and positioned his knees up on the bed next to her hips. He backed up toward her as far as he could go and put his face down close to the floor. 

His legs were wrapped around her and spread, and his ass was positioned perfectly for her and her hefty bath brush. She patted his bare cheeks with the large, round brush head. "This is going to hurt, darling, but I expect you to stay in position. Am I understood?"

"Yes, ma'am," he said shakily.

"Good," she said as she landed a hard spank squarely on his right cheek. 

"Ohhhh," he groaned, his whole body tensing up. "WHAM!" Another blow landed on his left cheek, making him drop from his hands to his elbows. 

This position only made him even more vulnerable, and she took advantage, raining hard swats on his tender bottom. The heavy brush had no give as it pounded Pete's ass relentlessly. His intermittent cries turned into one long howl as she continued. 

Pete did his best to make it to the end. She finally stopped as Pete was weeping with his face on the floor. She massaged his throbbing cheeks until he stopped crying.

His legs were still spread in front of her, and she noticed his arousal returning as she rubbed his cheeks softly. "Ohh, honey, you took your punishment like such a good boy," she cooed as she let her finger trail down his crack to his tight hole. "Do you like this?" she asked as she circled the tip of her finger around the rim. 

"Ohh, god, yes," he moaned as he spread as far as he could for her. 

"Hmm, I bet you do, but it appears not all of your ass has been spanked properly. Your cheeks are nice and red, but there's a lot of skin here that's been left untouched. It appears we have unfinished business to attend to."

He froze at her words.

"Petey, please be a dear and go get a wooden spoon from my kitchen. I think the small round head will be perfect for this."

"Please, ma'am," he pleaded.

"Now is not the time, honey. You are still being punished. Go do as you're told."

"Yes, ma'am," he replied submissively. He got up, retrieved her wooden spoon, and handed it to her.

"Back into position," she commanded.

He got back into the wheelbarrow position and hid his face in his arms on the floor. 

"Good boy," she replied happily. He was fully spread out for her as she patted his sensitive skin between his cheeks with the spoon head. She connected with his hole, making his body flinch and jolt. 

She continued a light pitter-patter of spanks on his hole and the surrounding area, making sure to include his exposed balls once in a while to keep him from getting used to the sensation. After lightly spanking up and down his crack, she increased the power to a harder spank, which made his legs instinctively close in protection.

She spread her legs out, pushing his legs open, and she held one of his cheeks open as she spanked his asshole hard, sending his body into a frenzy. She continued spanking his sensitive skin until every part of it was glowing red.

She set the spoon down. "It's all over, honey," she purred as she put both her hands on his exposed ass and resumed massaging his cheeks, allowing him to catch his breath. 

Muffled moans of pleasure escaped his mouth as she kneaded her thumbs deeply into his burning skin. His penis remained hard, dangling between her legs.

She repeated how good a boy he was, reassuringly, as her fingers began exploring his exposed genitals. She teasingly played around the opening of his tight hole, gently squeezed his balls, and pressed against his pleasure nerves repeatedly. The sensations he was feeling were bringing him close to orgasm once again.

"You were so good for me that you deserve a reward," she said as she wrapped her hand around his penis and began stroking. He had been brought so close already that he came into her lap within seconds. 

She rubbed him reassuringly for a while before having him stand up. She stood up, embraced him lovingly, and held him. Her warm embrace almost made him want to cry again, and he wanted to stay in her arms forever.

She finally let go, and he put his clothes back on. She smiled as she watched him get ready to go. "Whenever you need a haircut again, you make sure you come here. I'll take good care of you."

He looked back at her, smiling shyly. "I promise, I will."