Bailey took the job because she needed it but didn’t expect to like it. Retail is a pain in the ass with all the weird hours and working holidays, but this job turned out to have one interesting element to it that was completely unexpected.

Working in at a chain drug store is usually boring with people buying vitamins, shampoo, skin crème, makeup etc. but there are other things that present interesting and sometimes funny or embarrassing situations, particularly with sex-related items like condoms and lube, for example. Unexpected people buying unexpected things, or large quantities of them, raise all sorts of questions in one’s mind which of course one can’t ask.

The surprising item purchase though turned out to be hairbrushes, specifically by men. The aisle with the brushes was in sight of the checkout area enough that she could see what they were doing, and it made her wonder where men bought their brushes for use on their hair because that certainly isn’t what they were in her store for.

Bailey is a tall, plain-looking girl who attracted attention with an outgoing, quirky friendliness that caught people off guard, men in particular. She had a pleasant face; friendly, happy, cute maybe, but not exactly pretty. She had a tall, slender body showing little shape, no athleticism, and small tits. Light brown hair hung straight to her shoulders looking well-kept, but not terribly stylish. She normally dressed rather plainly as well, and in her store uniform, only her black pants generated any interest.

Her height was clearly in her legs and though not shapely, their length and girth were very attractive, but it’s where they led that was her strong point, as she had a perfect, round, just-big-enough ass with a deep cleft accentuated by the thong panties she wore when she was trying to attract attention to it.

How appropriate it was then that she absolutely loved to get spanked and any man who enjoyed having a naughty girl across his knee for a good spanking, would be attracted to Bailey simply because she had this gorgeous, oh-so-spankable bottom! Being a switch, she was no stranger to taking a naughty boy’s pants down to punish his bottom properly with her hand, and her favorite implement, the hairbrush, but given the choice, she’d choose to have the brush applied to her bottom rather than his.

Her interest in spanking started with a boyfriend who reacting to some silly mistake, pulled her down over his knee and spanked her a dozen or two times over her flimsy skirt. Embarrassed, but also instantly intrigued, she filed those feelings away for the future not knowing how to explain them to herself let alone him. It wasn’t a natural reaction for him either so Bailey had to be a bit more overt when she wanted him to do it again; misbehaving was not enough to get a repeat performance.

She liked the ‘naughty girl’ emotions it raised, but it was the sting, the pain that really got her attention, especially when on that second occurrence she reached back and pulled her skirt up. It seemed like every nerve ending in her bottom was firing and made a direct connection to her dewy pussy which naturally led to increased liveliness in the sex that followed. He wasn’t all that excited by the actual spanking, but the way it turned her on was enough to have him continue.

Her desires escalated rapidly and the third time on her bare bottom was when she realized she was hooked, no longer satisfied with conventional sex; needing the extra stimulus that a stinging butt provided. He wasn’t all that thrilled with the increasing length and severity of the spankings she needed, but as her appetite for sex increased along with it, he went along.

On what would be their last night together, she pulled a heavy, wooden hairbrush from her handbag after the first fifty or so spanks with his hand and insisted that he ‘beat her bottom’ with it, which he reluctantly did. Thinking he might cure her of this kinky desire, he really let her have it but good, smacking the gorgeous bottom in his lap until he could see bruises starting to form, but his plan backfired as some demon in her was released for the physically demanding and exhausting sex that followed.

It turned out to be a fortunate/unfortunate story for her. Unfortunately, despite having had the best sex he had ever experienced, he had had enough of being almost frightened at this need she’d developed and broke up with her the following day. Fortunately, she now knew what she wanted and needed, and dealt with the loss of her boyfriend by admiring the purplish/blue bruises in the mirror.

Almost weekly she’d see a man checking out hairbrushes, which would immediately grab her attention, and as they avoided busy times, she was often free to keep an eye on them. The telltale sign that they had no intention of brushing their hair with it was when they would tap it against their palm, sometimes rather forcefully. In fact, it was this unmistakable sound that often drew her attention to such a customer. Taking their time to try and find just the right type of brush gave her the time to see if they needed ‘any help with anything’.

At least half the time they’d be embarrassed by her attention, quietly say ‘no’ and run off to some other part of the store trying to make it look like that wasn’t the only thing they were there for, but just as often these same men would leave the store a bit later having purchased nothing.

The ones she enjoyed were those that weren’t trying to hide what they were after and with a little friendly prodding would admit the brush was needed to smack the bottom of someone in much need of a good spanking, which often as not was themself. Regardless of who was to be the recipient of his hairbrush purchase, the open conversation about spanking always got her panties quite wet, and for hours afterward, she’d be clenching her cheeks as though anticipating the next swat from the brush.

She’d walk up as they took one brush after another off the hooks and tapped their hand with it, testing the sound of it as much as the feel. Wielded properly almost any hairbrush can be an effective spanking tool, though there are several elements that make one better than another depending on your tastes, and she would try to help them sort out those needs to get the best hairbrush for their personal desires, all the while her own desires dripping into her panties.

It was late one evening when an attractive man, in his late twenties or early thirties, walked in and walking directly up to Bailey at the cash register asked where the hairbrushes were. She pointed and gave him the aisle number, got a friendly ‘Thank you’ and off he went. She was immediately intrigued as most guys didn’t want to call anyone’s attention in so open a manner to what they were looking for but resisted the temptation to run over and try to help him too soon.

Hearing various popping sounds, the obvious – to her – sound of a plastic brush with a mostly hollow body, she decided to see if she could help and went into the aisle with a friendly smile.

“Do you need any help with your selection?”

“Um … it’s kind of personal,” he said just a bit shyly, but not running out of the store either.

“Okay, but I think I know what you’re planning to use this brush for,” she said with a sincere look. Stroking her hand across her left cheek, she added, “… and having personal experience in that area, I think I could be helpful.”

He looked just a little embarrassed and wasn’t sure what to say or how to react to her forward statement and though aroused at her gesture, he still wasn’t sure if she really knew what he was looking for.

“Let’s start with a simple question. Do you want it to be playful or painful?” she asked with an impish smile and both hands quickly stroking her bottom as though anticipating the spanking herself.

“Painful, I think,” he replied still hesitant, “But all these don’t …”

“Yeah, the plastic brushes will take a lot more effort to provide a good … sting, and they don’t sound very threatening, do they?” He loosened up a bit, knowing now they were in fact on the same page.

“I was looking for a wooden one, kind of like this but thicker? Heavier?” he said pointing to the one wooden brush among all the plastic ones.

She perked up noticeably, suspecting he had some experience as well; just the kind of guy she’d been hoping would come looking for a good hairbrush and hoped she’d be able to put a plan she’d developed into action.

“Good. They sound better too, don’t they?” she asked, finally getting a bashful smile from him.

“I saw one in a … a video,” he said, not wanting to admit to having been the recipient of such a spanking. “She carried one around in her handbag … just in case, you know?”

‘Sounds like it’s gonna be used on his bottom,’ she thought to herself but made up her mind to go for it anyway. The store carried only one hairbrush that she considered worthy of being used to spank a naughty bottom and they usually only had one in stock, so she kept it hidden to avoid it being purchased when she wasn’t there, unavailable for use as part of her plan.

“We do have one brush like that, and I keep it right,” she paused fishing around behind some boxes on an adjacent shelf, “… here!” She held the brush in her hand and smacked it against her hand fairly hard, the sound and the action startling him a bit, but also showing some intrigue in his face. All wood with stiff bristles, it was shaped somewhere between a rectangle and an oval, with a large, flat back.

“This is the perfect brush for that naughty bottom,” she said seeing his interest visibly rise. “Three-quarters of an inch thick, solid oak, and a comfortable handle,” she said and smacked it against her palm again a little harder than before. “The edges are rounded to avoid the bruising that comes from a sharp edge and the weight will ensure it will be felt! … as soft or hard as you wish!”

His interest was now unmistakable, but she really got him going when she reached back and gave her right cheek a good, hard smack with the brush just before handing it to him. He took it from her with a look that said he really wanted to get spanked. He looked it over taking note of the features she’d mentioned, smacked his own hand a few times, and then picking up the dangling price tag, looked disappointed.

“Wow. A hundred bucks! That’s really expensive!”

“It is, but I think you’ll find it's worth it,” she said gauging his reaction and decided to enact the last part of her plan. “You see, this brush comes with an unusual warranty. Would you like to see it?” she asked and, getting a nod, went back to the front counter to retrieve something from her handbag and returned to him handing him the ‘warranty’ she had made up herself.

“This company knows what people use their hairbrushes for,” she explained as he read.

 THE HERTZMORE BRUSH COMPANY

Thank you for considering one of our handmade hairbrushes. We know you have many choices of brushes for your special purpose, and our prices are considerably higher than conventional hairbrushes, but we believe you’ll agree that our unique warranty makes it worth your consideration.

Our hairbrushes are made from the highest quality wood, both sanded and finished by hand to ensure maximum comfort for you as well as the recipient of its use. The heavier weight and shape of our brushes have been carefully designed to provide the impact you are both expecting.

To give you the confidence you need to be comfortable with your purchase, we offer you the opportunity to try our brush with a trial and demonstration after which if you are not completely satisfied, the full purchase price will be refunded.

After your purchase, the representative who provided this warranty will make an appointment with you for the sole purpose of providing a trial of the awesome capabilities of our brushes, both giving and receiving a real and complete demonstration of its amazing properties.

We stand behind our products and in addition to our unique warranty, guarantee that at least the purchase will be painless!

©Hertzmore Brush Company

“Is this for real?” he asked clearly interested, but not believing.

“Mm-hm,” she said with a devilish smile.

“When could we … you know, do the demonstration?”

“Tonight, if you like!” she said, her bottom begging for a beating and that squishy feeling in her panties.

“Wow. When do you …”

“I get off at ten. I could come straight to your home after,” she interrupted.

“How long is the … demonstration?

“You get at least an hour,” she said emphasizing ‘at least’ and hoping it would be longer. “Unless you don’t like the brush … and want to cut it short,” she added with a disappointed tone.

“Not much chance of that,” he mumbled. “You’re sure?” he asked now in a full voice.

“Oh yes!” she said her desire visibly on display again and her cheeks clenching in anticipation.

“Okay. Let’s do it!” he said nervously and followed her back to the cash register.

With a nervous smile, he handed the brush back to her and she scanned the barcode. It wasn’t really a hundred-dollar brush, it normally costs less than twenty dollars, but who would believe such a cheap brush would come with such a ‘warranty’, so Bailey had repurposed an old SKU and ‘Hertzmore Hairbrush w/extra warranty - $100’ came up on the cash register display. Smiling at her subterfuge she noticed he’d seen the display as well and shook his head still with an element of disbelief.

“I’m Bailey,” she said pointing to her nametag. “… and I see your name is Justin?” she said looking at his credit card as she hit the key to finish the credit card transaction.

“Yes, Justin. Nice to meet you, Bailey!” he replied with a nervous smile.

“Well, Justin, if you’ll give me your address, I’ll see you in a little over an hour.”

She wrote down his address and mobile number and he left, seemingly happy. Now it was her turn to be nervous, realizing she was taking a significant risk going to the home of a person she’d just met, and not just for a cup of coffee, but it was what she was really going for that overpowered her fear. She resisted the temptation to satisfy the hunger between her legs both wanting the anticipation to build, but also knowing her manager was still in the store somewhere.

Justin left with some apprehension as well, still not believing what had happened, and even more what was supposedly going to happen. He’d gone into the store only to buy a hairbrush initially to use on himself, hoping to satisfy a need created by a girlfriend who’d spanked him three times and dumped him, but if this were on the level, he wouldn’t be spanking himself tonight.

The first time this girlfriend showed this dominant side, he thought he’d just be told what to do in bed, satisfying her needs first and he liked that idea, but then he’d made some silly mistake and was told he needed a spanking. Before he could even find the words to object, he found himself bare-assed and across her knees about to get spanked for the first time in his life. He managed one word, ‘Hey!’ before the spanking began, her hand hitting him all over his naked bottom at a brisk pace and ever-increasing intensity.

Eventually, the shock of the situation wore off and he found himself enjoying both the intimacy; his bare mid-section laying across her equally bare and shapely thighs, with one arm around his waist holding him tightly in position, while the other rubbed his sore cheeks between flurries of spanks … and the submission; doing what he was told and paying the price for failure with a good old-fashioned spanking on his bare bottom.

What really surprised him was when the pain started to feel pleasurable, a feeling he didn’t trust until he found he was genuinely disappointed when she stopped. It wasn’t exactly arousal he felt during the spanking, but he knew he liked it and wanted more, and the sex afterward was amazing, for him anyway.

A few days later she decided he needed to be spanked again, and this time he participated quite willingly, with the same end result, but it was the third time that really cemented his interest in this submissive activity. Declaring that her hand wasn’t hurting him enough, she produced a hairbrush seemingly out of thin air and after showing it to him in a threatening manner proceeded to paddle him good and hard with an unknown, but large number of swats.

The suddenly much more intense pain of the brush on his already-spanked bottom fixed his attention on the concentrated sting of each swat and though he squirmed, cried, and complained about it, he knew he wanted, no, needed this on a regular basis. He wanted to be told he’d been a bad boy and get spanked first and finished off with a good paddling from the hairbrush. He was completely hooked when with his punishment complete, he was made to worship her dripping wet pussy as she sat firmly on his face.

She called about a week later and broke up with him for some bullshit reason, leaving him devastated; not because he liked her particularly much, but because he would sorely miss the intense spankings with hand and hairbrush. A few weeks later he read about self-spanking and found himself shopping for a hairbrush at the drug store.

Time passed slowly for them both, but they got quite excited when she rang the doorbell of the small house he rented just a few blocks from the store.

“Hi, Justin!”

“Hi, Bailey! Come in,” he said as he stepped aside to let her pass and followed her into the small living room into which the front door opened. “Would you like something to drink? I’m afraid I only have beer and wine.”

“A glass of white wine would be nice,” she replied sitting on the sofa. She smiled and squirmed a bit when noticing the chair in the middle of the room with the brush on the floor beside it.

“Here you go,” he said returning with two glasses of wine, placing his on the coffee table. “I can’t believe we’re really doing this!? Are you really gonna spank me? … with the brush?”

“We’re both going to get spanked, Justin,” she corrected to his surprise.

“Really? You want me … to spank you too?” he said his nervousness returning.

“Well, it is part of the demonstration of the brush; ‘both giving and receiving a real and complete demonstration’,” she said a little concerned that she might not get what she wanted most out of this game. “… and I think I should get spanked first so you know this is all on the level.”

“Okay,” he said with a small smile that put her mind at ease. “I … like you, Bailey. You’ve been very nice and … and honest with me.”

“Oh. Well, thank you … but that’s hardly the kind of thing you’d say before taking a naughty girl over your knee for a good spanking,” she said with a suggestive smile.

“So … you’ve been a naughty girl, have you?” he asked, trying to get into a role he wasn’t used to.

“Yes, Daddy! I’m sorry,” she said cutely and noticed he seemed to like being called that.

“I think you know what naughty girls get, don’t you Bailey?”

“Yes, Daddy,” she said softly, “They get spanked. Are you gonna spank me now?” she asked, really enjoying the little girl role, and anxiously awaiting being taken over ‘Daddy’s’ knee for her spanking.

“Yes, little girl,” he said to her visible delight and got up to sit in the chair. “You’re gonna get a good spanking. Now come here,” he said pointing at the floor to his right. She got up feeling the squishy wet gusset of her panties between her legs and went to his side.

“You know what to do,” he said expecting her to just lay across his lap.

“Yes, Daddy,” she replied as she pulled the zipper of her pants down and tugged the tight waist down over her hips, below her cheeks, and left them at mid-thigh. Justin’s surprise turned to shock when her panties were the next to go, giving him an up-close view of her clean-shaven pussy; a perfect cameltoe with puffy lips and a tight slit.

Loving the surprise she saw on his face, she smiled at him as she bent to lay in his lap and asked in her cute, little girl voice, “Why do I always have to get spanked on my bare bottom, Daddy?”

Surprised, but also thrilled that he’d been wrong to assume that the so-called ‘demonstration’ would be with clothes in place because he now correctly assumed that his spanking would be on his bare bottom as well. Having never done this, he tried to draw on the little experience he had and putting his left arm around her waist, pulled her to him and placed his hand across her bare bottom, noticing for the first time how beautiful and shapely her bottom was.

“Wow, Bailey! Your bottom is so …” he started.

“Spankable?” she suggested looking back at him with a smile.

“Yes … spankable! … and naughty girls need to be spanked, don’t they?” he asked as he began smacking her perfectly round cheeks playfully. He knew he should warm her up first, at least that’s what he’d been told when he’d been spanked, and although knowing the intensity ramped up steadily, he was unsure where to start and how quickly to proceed.

“Ow! Yes, Daddy! Thank you for not spanking me so hard,” she said, happy that he understood she wanted it harder and started to feel that delicious sting. “Ooo!” she cooed wondering to herself as she had many times before, ‘What is it about an over-the-knee spanking that gets me so hot?’ The position, the submission, and the exquisite sting all conspired to get her so fucking wet!

Justin was enjoying it more than he’d expected, largely because he could see how much she was enjoying it, that submissive ‘please her first’ attitude taking hold. Harder and harder he spanked keeping a watchful eye on her reaction and body language, but also absolutely loving the way her reddening cheeks reacted to the spanks, the firm globes jiggling and swirling just enough to be extremely exciting and producing a pronounced bulge in Justin’s shorts.

The role-playing forgotten for the moment, the spanking continued with their mutual sexual desire unmistakable as they traded audible expressions of pleasure.

“Oh, Daddy! Do you have to spank me with the hairbrush?” Bailey said giving Justin the cue he needed to transition to the brush.

“Yes, Bailey! We would be done by now if you hadn’t lied to me about what you did, so now you’re going to get a good, hard paddling on your bare bottom with the brush!” he said as he reached down for the brush and tapping it on her cheeks first, resumed spanking harder than Bailey was expecting.

“Oh! Ow! Ohh! Ow-ow-ow! Oh my …” she cried and looking back at Justin tried to communicate with her eyes that yes, it was hard, but it was exactly what she wanted. Squirming and gasping aloud she was reminded that although it wasn’t arousing anymore, this is the way she wanted to be spanked. The pain built in her crimson, red cheeks and while she didn’t know why, she knew she loved it, wanted it, relished it, and needed it.

Her amped-up reaction to the painful spanking had Justin thinking that he might like to continue giving as well as getting spankings. Happy that he’d correctly read her facial message, he continued the paddling at a slower, but very steady pace, stopping only once for some soothing caresses of her tortured bottom, her deep breaths signaling pleasure, while raising her bottom asked for more.

Feeling she had about had enough; she tucked her bottom in in an unsuccessful attempt to evade the punishing paddle. Without any warning he suddenly stopped, leaving her feeling like it was good timing, but she would like just a little more.

“Ow! Oww! Owww! Oh fuck!” she screamed as Justin, seemingly reading her mind gave her a dozen more, six in a row on each cheek and much harder. Obviously, he hadn’t read her mind but had again reverted to his personal experience knowing that he liked a hard finale to his spanking, again giving her just what she wanted.

“Justin … that was so … so perfect!” she praised, to Justin’s delight, and stayed in place giving him a wonderful performance of a naughty girl reaching back to rub her sore bottom.

Scrambling off his lap with his help, she ended up kneeling beside him with a satisfied smile. Walking on her knees she moved in front of him, between his legs, reached up to the waistband of his gym shorts, and slipping her fingers into the elastic on both sides began tugging them down, Justin lifting his hips to allow them to pass with his steely shaft popping out of its confines in the process.

“Thank you for spanking me, Daddy!” she said, and feeling this was the proper way to show appreciation for her deliciously sore bottom, tugged on his knees to get him to the edge of the chair. She took him in her mouth and with the addition of her hands licked, sucked, and stroked him to a powerful ejaculation, shooting several feet in the air and landing partly on the coffee table next to his glass of wine, Justin still moaning while she let him shrink in her mouth.

“Bailey, that was amazing,” he gushed as they stood and hugged each other. “I’ve never … done that before,” he confessed.

“I could tell, but only at the beginning. You learned fast!” she said to a frown growing into a smile, “and you wielded the hairbrush like a pro!”

She liked that Justin was beaming with pride as they stood apart. Bending down she stepped out of the pants around her ankles, but pulled her panties up tight against her pussy, the cool dampness from before mixing with the warm juices more recently produced. She suspected that he’d done as well as he did only because of his natural desire to please a woman, but with a little coaching he’d get better at it. She hoped that desire would show itself again when it was his turn to thank her since the perfect pain in her bottom was making her wetter still.

Justin was relieved when she suggested they sit and talk for a while. It seemed right to have some separation between the two spankings, but even more, he was still a bit nervous about having someone new spanking him, the realization that his bottom would be bare was both extremely exciting and a little embarrassing as well, as it should be.

Bailey encouraged him to tell her about his first experience with spanking; his only experience she found out. He felt better when he learned that her first experience had been similar in that they’d only been given enough real spanking to know they craved it when their partners had left them, the difference being that Bailey’s had been quite a while ago with several opportunities for more spanking since, while Justin’s was still agonizingly fresh in his mind having occurred only a month before.

“You know it was very naughty of you to trick me as you did in the store,” Bailey started and interrupted his real objections to her lies, “getting me to pull my pants down and lay across your knees so you could spank me! … really hard! My bottom still hurts!” Rubbing her bottom, she saw Justin catching on to her provocation.

“I’m sorry! I didn’t mean to …”

“It doesn’t matter what you meant to do!” she interrupted, “The fact is you brought me here, plied me with alcohol, and took me over your knee to give me a spanking on my naked bottom!”

“I’m sorry, Miss! I really am!” he replied, slipping easily into this more familiar role. “I’m gonna get punished, aren’t I?”

“Yes, Justin. It’s only fitting that you be disciplined at least as much as I was! … and a good, hard spanking is clearly the only proper way to punish you,” she said noting that he was getting off on the repartee as much as she was.

“Do I have to pull my pants down?” he whined, playing his role perfectly and seeing her threatening nod continued, “Please don’t spank me with the hairbrush!? It hurts so much!”

She didn’t answer him right away, choosing instead to start the proceedings by getting up and sitting in the chair. Solely for his pleasure she started pulling her uniform shirt up and off as she sat, then reaching back for the clasp of her bra, removed it as well revealing her small, but beautifully shaped breasts, which left her naked apart from her panties. She wanted them soaking wet when it was time for him to remove them later.

Pointing at the floor in front of her, she wordlessly instructed him to stand before her and once there told him to remove his shirt. As he pulled the shirt over his head, he felt his pants and underpants being yanked down forcefully and left around his ankles. A slap to his calf told him to step out of the pants, after which Bailey tossed them away indicating he wouldn’t need them any longer.

Justin was beside himself with desire, his stiff dick pointing straight at her like an empty flagpole. Being a panty freak he loved that she was naked but for her tight, white panties. He still couldn’t believe this was all happening but couldn’t wait to feel her hand smacking his bottom. He didn’t have to wait long as she turned him sideways in front of her and started spanking him much harder than he’d ever been at the beginning.

Getting her first look at his fleshy round cheeks, she couldn’t wait to see how they’d react to her spanking hand, enjoying the way they bounced and jiggled in this relaxed position as she spanked him harder than she’d originally intended, so enthralled with the sight as she was.

The sting was building rapidly with this unexpectedly harsh beginning and while his mind and ass were saying ‘Yes!’, his cock was saying ‘No’ and shrunk to a fully flaccid state. While every hard swat was pure joy for him, his body reacted involuntarily, twisting, and pulling away to evade her punishing hand.

While still preferring to be the one getting her backside beaten, there were times like this when she truly enjoyed the dominant role. While her reasons for spanking him like this so suddenly had been purely for her own pleasure, she liked that his erection had subsided and used his squirming as an excuse to move on to the next phase of his spanking.

“Stop squirming,” she ordered but seeing he was unable to comply she stopped and added, “Get over my knee! If you thought that was hard, just wait!”

Taking his wrist, she moved him in one smooth motion to her side and over her left knee only, her right leg lifted over his to clamp him tightly between her thighs. This was a new feeling for him, being restrained as he was, which triggered a stirring in his crotch only to be cut short by the resumed, painful spanking. ‘Oh my god!’ he thought, as the pain and pleasure mixed in his brain left him feeling like he never wanted it to end.

“Oh, Miss! You’re spanking me so hard!” he cried making it sound more like a compliment than a complaint.

“You deserve a good, hard spanking, don’t you? Come on! Tell me!”

“Yes, Miss! I deserve to be spanked and paddled really hard! Spank me! Spank me!” he said his voice rising and desire oozing out of his words.

Having mentioned paddling she suspected he was ready for the hairbrush, but she wasn’t. She liked the flesh-on-flesh contact and stepped the intensity up, building to a crescendo of both spanking and scolding before changing to the brush, his grunts, and louder exclamations proof that she was getting to him.

‘Oh fuck!’ he thought as she spanked harder and harder all the while telling him how much worse the hairbrush was going to be. This was a unique experience for him, not just because he’d spanked Bailey, but the way she handled him. He liked it … a lot! Bailey was such a sweet girl both at the store and when he’d spanked her, but a real disciplinarian towards him, a feeling felt especially strongly as she switched to a pattern of several spanks on one spot, and a repeat performance on the other cheek, and then stopped.

“Oh my god!” he screamed as his body arched and stiffened in response to Bailey’s fingernails being scraped over those two spots she’d just sensitized for him.

“Mmm, I think you enjoyed that a little too much, hm? Do you like getting spanked, Justin?” she asked teasingly and getting no response added loudly, “Answer me!” with a few even harder spanks.

“Yes, Miss! Ow! I like getting spanked! Oww! You can … OW! … spank me some … Ugh! … some more if you want to!”

“Of course, I can! I can spank you as long as I want to!” she said reaching down for the brush, “but you’re liking this too much! It’s supposed to hurt, so that’s why I’m going to use the HAIRBRUSH!” she said swatting each cheek in turn on those last two syllables

‘Here we go’ he said to himself sensing the imminent arrival of the brush, yelping loudly, “Yeow!” when he felt those first two. The pain level seemed to double as those two spots felt like they were on fire, and he was doubting his ability to take as much as he’d given Bailey assuming that was the minimum he would get.

Bailey liked the bright red spot she’d created on each cheek but felt she may have gotten carried away with wanting to be sure he felt the difference between her hand and the brush with those first two swats. For the first time his hand came up to try and rub away the pain, but she pulled his arm up behind him with her left hand and resumed paddling him, but not as hard as those first two.

‘Oh, that feels good!’ he thought as the swats rained down at a slower, but just as steady pace as the spanking. Thinking the first two had numbed his bottom, these hurt but in a good way, not realizing Bailey had backed off on the force of the spanking.

“Hurts a little more, doesn’t it, Justin?” she said mockingly.

“Yes, Miss! Oww!” he answered but wasn’t going to tell her how much he liked it and soon he wasn’t liking it so much as she gradually stepped up the energy of the swats, his body cringing and protesting the harsh punishment. He was at his limit, but she pushed past it without hesitation.

The brush had amplified Bailey’s enjoyment of her dominant role wanting to spank him harder and harder but realized that if she pushed him too far, he might not want to do this again, and she definitely wanted to experience both sides of hairbrush spanking again with Justin. His panting and almost screaming reached a level where she feared she’d gone too far and backed off to a few playful swats on each cheek before stopping.

“You took your spanking very well, Justin,” she said releasing the arm she’d held back, loving the way his hands furiously rubbed his cheeks as the bruises continued to develop their color.

“Thank you for spanking me, Miss,” he said in a halted manner with his breathing still unsteady.

She helped him up, delighted in the way he still tried to ease the pain. Still holding both burning buns, he moved to stand in front of her and knelt between her legs. Both expecting this show of gratitude, she slid to the edge of the chair, legs spread, and he moved in taking her panty-covered pussy in his mouth hoping her panties were sopping wet with her juice. He wasn’t disappointed as he pulled them into his mouth, sucking the savory scent of her cunt into his mouth as though tasting a fine wine, Bailey gasping at the extreme pleasure of seeing him drink her in.

“Oh god! Take my panties off and eat my pussy, Justin!” she begged with a desire she hadn’t felt in a long time. Even the removal of her panties was a near-orgasmic feeling as he slowly peeled the fabric away from her swollen lips, long tendrils of her sticky fluid breaking away only after stretching to an inch or two. Those connections now broken, her panties rolled into a string as he slid them down her legs and off, only to be thrown over to wear his underwear lay as well.

Justin loved this part having developed his technique with much practice and dove in, tongue first to show her what he could do. Using a tease and denial method, he’d bring her to the edge with one activity; sucking her labia, penetrating her with his tongue, or flicking her clit, only to stop and move on to something else, as her disappointed moaning signaled that he’d done it right.

Using his fingers sparingly, his tongue did most of the work, until he was ready to make her cum then with his mouth and tongue working on her clit, one finger and then two slid inside to slowly fuck her tight pussy, both activities accelerating till she was near the edge. Gasping with the approaching climax, he triggered it with a fingertip first just pressing on her anus, then pushing it up to the first knuckle.

“Oh fuuuucccckkkk!” she screamed as wave after wave crashed over her with her legs trembling and her body jerking spasmodically, the extraordinary torment continuing as Justin didn’t let up for a second. Heavy uneven breathing, grunts, and groans were all she could manage as the immense pleasure gripped her repeatedly.

The spasms having subsided, she pulled Justin’s face up to hers and kissed him with her tongue savoring the taste of her in his mouth and all over his face. Moaning into each other’s mouth they wordlessly expressed their mutual gratitude for the incredible time together.

Standing up, they caressed each other’s battered bottoms loving both the soothing touch and the occasional stabbing pain their fingers wrought.

Retrieving their clothes, Justin put only his shorts on and enjoyed watching Bailey dress. She may not have been a pretty girl, but to Justin, she was absolutely gorgeous. Watching her trying to pull her tight pants over her sore bottom was arousing in itself, noticing for the first time how the tight pants enhanced her perfect bottom.

While they had certainly been intimate enough that going the next step might seem a forgone conclusion, they guessed that neither of them would want to do anything more, choosing instead to savor the memory of what they’d already done.

“We probably shouldn’t … you know,” Justin said feeling it had to be confirmed with words.

“Maybe next time,” she said hopefully.

“Will there be a next time?”

“Would you like there to be a next time?” she asked, lobbing the ball back into his court.

“Do I have to buy another brush?” he asked jokingly.

“No. I think the one you have is more than adequate, don’t you?” she asked, rubbing her sore bottom enticingly with that devilish smile he’d come to like.

“Definitely! I’ll …”

“Call me!” she said with an implied ‘or else!’.