Chris really didn’t know when he first became fascinated with spanking. Spanking; certainly not the craziness of his mother chasing him around the kitchen with the dreaded “wooden spoon” in an attempt to land a glancing blow over something silly. No, a spanking as an adult that was formal over the knee spanking was what he was always curious about. If he had to guess, it was from the books he read and the movies and television that he saw growing up, as there seemed to be a lot of it going on back then.

It was a rite of passage in his high school that a guy, on his eighteenth birthday, would go to the adult book store, since it would be legal. Chris went with Randy, older by a month and his best friend, and who had waited for Chris to turn eighteen so that they could both go together. They were agog at the blatant sex on display: movies, magazines, books, sex toys, clothing, etcetera. Chris was surprised to find an entire aisle of the store dedicated to spanking in its various forms.

There was something about the idea that got his dick rising. Randy noticed right away and pulled a single scene spanking movie from the shelf. “My treat, birthday boy!” he said as he paid the rental fee and headed to one of the viewing booths. Chris, a little shy, kind of ambled over until he thought no one was looking, and then joined Randy.

As with most porn, the plot was thin, the dialogue cheesy, and the acting reminiscent of a grade school play. In this case, a “teenage” failing student at a private girls’ school was being spanked for poor grades by her Adonis headmaster. Of course, she had to be fully nude, and just happened to have a rather large hairbrush in her purse.

After a somewhat superficial but very noisy punishment over his knees, he briefly fingered her and then pushed her to the floor, where she proceeded to deep throat Adonis until he came all over her breasts. Chris ignored the blow-job. Instead, he became very interested in the shapely curve of the girl’s bottom, and how nice it looked draped over Adonis’ lap; how the hairbrush made it jiggle with each blow; how sexy it looked with dark pink splotches covering each cheek; and how much the girl seemed to like it (probably the best acting in the whole vignette).

“Didn’t do much for me,” Randy commented, as he noticed the bulge in Chris’ pants, “but I guess you liked it just fine.”

Unfortunately, Chris never got to enjoy any hands-on experience with spanking. He was too shy to ask any of his dates, and none ever gave any indication that a spanking was something that they’d ever consider. Still, Chris never stopped thinking about what it would be like to use a hairbrush to “pink up” a delightfully rounded pair of ass-cheeks (it was his go-to masturbatory fantasy). And so, instead, he collected hairbrushes.

****************************

“I think she likes you,” Randy chided, as he and Chris sat at the bar, celebrating their fortieth birthdays. Randy had just introduced him to Karen, a woman in his office who just happened to be there. Karen had excused herself to go “powder her nose” with one of her girlfriends; girl-speak for trading intel.

“So what is she really like?”

“Same age as us, maybe a little younger. Quiet, mostly, but not shy. Wicked wit, too. Somewhat of a behind the scenes instigator. Doesn’t date a lot and never seems to stay in a relationship very long when she does. Something tells me that she’s a real tiger in the sack, and the guys she picks can’t handle it. Come to think of it, she may be too much for you. You won’t get her into bed with that 'aw shucks' approach you normally come to the plate with.”

“Hey, women like a gentleman.”

“My opinion, what she’s looking for is a firm hand on the tiller.”

*******************************

“So, Karen, what do you think about Chris? Nice guy, huh?”

“I don’t know, Carol. He seems a little unassertive.”

“The guy’s a gentleman, unlike that sleaze-ball Randy.”

“Yeah, I guess. Still, I like someone who’s a little more take-charge.”

“You mean someone who’ll throw you down on the bed and fuck your brains out, instead of the other way around!”

“Well, yeah, and I’m not sure Chris is that guy.”

“C’mon, give the guy a shot.”

********************************

They were at a restaurant. It was their third date, and they hadn’t gotten beyond kissing at the door and holding hands. Both were frustrated with the lack of progress, but for entirely different reasons, and neither would bring it up. Karen was waiting for Chris to take charge and move things to the next physical level, whilst Chris kept waiting for a sign that Karen had feelings for him like he was beginning to have for her. They had finished eating, and were in somewhat of a quiet moment, when Randy and Carol walked up.

Karen was kind of surprised since Carol considered Randy to be a sleaze, and excused herself so that she could get the lowdown. Chris was also surprised that Randy had asked Carol out, since her disdain for him was pretty evident.

*********************************

“How long have you guys been dating? I thought you couldn’t stand Randy. I can’t believe he asked you out!”

“Since that night you met Chris. And, well, he didn’t really ask; it was more of a command. He told me that it was his birthday, and that I was going to blow out his candle. Then he grabbed my hand and put it on his 'candle'. More like a fuckin’ torch!” She paused as she quickly remembered their first encounter. Her pussy twitched. “So, anyways, what about you and Chris? What’s the deal with his 'candle?'”

“Wouldn’t know,” Karen admitted. “He is a great guy, and I like him a lot. Warm, funny, smart, attentive as all hell, and generous. He’s a hand-holder, and I bet his fingers have some real promise. And a great kisser. Just wish he’d try my other lips. He’s everything that a normal woman would want; to fall in love with. But that’s as far as we’ve gotten. I’m not sure this is going to work out.”

“You mean you haven’t…?”

“No, and I’m not sure that he’s even attracted to me that way. Are you sure that he isn’t gay?”

“God, I don’t think so. Do you want me to talk to Randy about it?”

“Hell no! I think that I’ll just cut my losses. Tonight is our last night.”

***********************************

“So, you two kids, how’s it going?”

“She’s a great gal Randy,” Chris said, “everything you said she was, and more. The kind of woman I’d want to fall in love with.” Chris sighed. “Oh, and a great kisser.”

“But?”

“But what?”

“Have you fucked her yet?”

“Well, no, but…”

“She kissed anything besides your mouth?”

“No, but…”

“You?”

“No.”

“What are you waiting for?”

“A sign, a signal …”

“What, like a burning bush? Dude, her bush is there for the burning! But you gotta strike the match. She won’t do it for you.”

“How do you know?”

“That first night, she told Carol that she was looking for someone to throw her on the bed and fuck her, not the other way around. She didn’t think that was you. Carol had to beg her to go out with you. You need to step it up. Quit looking for love. Look to get laid. The love can come later.” He saw Carol come out of the ladies’ room with Karen. “Heads up! I’ve got a plan. Follow my lead.”

**************************************

The guys both stood up as the girls approached the table. “We’re going to Chris’ place for a drink,” Randy announced. Chris saw the look that passed between Carol and Karen, and then between Carol and Randy, and knew that the evening was doomed.

Karen was quiet on the drive. Fortunately, Chris lived pretty close to the restaurant, so the uncomfortable trip was short. When they got there, Randy offered to help mix the drinks, and when they were alone in the kitchen, Randy whispered, “Mission aborted, dude. She’s going to break up with you.”

“Huh? What? How do you know?”

“They talked in the bathroom. You waited too long to make your move. She doesn’t think that you’re attracted to her 'in that way'. Man, she even thinks that you’re gay.”

“Fuck!”

****************************************

Karen and Carol were walking around, looking at the townhouse as neither had been there before. Karen noticed that Chris seemed to have a lot of hairbrushes. Fancy, plain, some even looked like antiques. There wasn’t any place that they stood where there wasn’t a hairbrush in reach.

Carol laughed. “The better to spank you with, my dear.”

Karen was holding one in her hand as Carol spoke, and the words caused a pleasant twinge in her belly. What kind of person would want to spank someone else? What kind of person would want to be spanked? And why did just the mention of spanking cause such a reaction? She quickly pushed the thoughts out of her head. “Are you sure he’s not gay?”

“I’m sure. Well, Randy is. They’ve known each other since high school.”

“You talked to Randy!?”

“Well, just about that,” not admitting that she’d actually blabbed everything.

****************************************

You could cut the tension with a knife as they sat and drank, pretty much in silence. As soon as they were done, Chris offered to drive Karen home, and she accepted. Chris walked Karen to his car, and Randy walked Carol to his. As soon as they were out of earshot, Randy grabbed Carol. “What a disaster. I feel sorry for Chris. I think he was falling in love with Karen.”

“Really? And instead. he’s getting dumped tonight. That’s gotta suck.” A pause, then, “Hey, listen… um… what’s the deal with all of the hairbrushes? It’s kind of creepy.”

“Oh, that. My boy Chris has a spanking fetish. Never acted on it, but man is he prepared if he ever gets the chance.”

“He likes to be spanked? Are you sure he’s not gay?”

“No! No! He wants to do the spanking. And definitely on a woman’s ass. Trust me. He’s just never had the chance.”

“Good to know,” Carol said, smiling. As soon as Randy wasn’t looking, she dashed off a couple of quick texts to Karen.

***************************************

Karen felt her phone vibrate in her purse, but was in no mood to answer it. She could tell that Chris had something on his mind, and she certainly had something on hers. They drove in silence to her apartment, and walked in silence to her door. She unlocked the door and began opening it, intentionally not giving him the chance to give her a goodnight kiss. She was surprised when he stopped her. “We need to talk,” he said.

“Now, out here?” she asked, hoping to avoid a scene.

“Yes now; but no, not out here.” He pushed the door open and walked in without waiting. Karen, a little surprised by the assertiveness, followed.

She closed the door. “Okay, talk.”

“Look,” he started, rather sternly. “I know that you like me a lot. That you find me ‘warm, funny, smart, attentive as all hell, generous and a great kisser’. Oh yeah, and ‘everything that a normal woman would want to fall in love with’.”

“How do you know…?”

“Except,” Chris went on, his voice rising, “you. Look, I’m sorry that I’m not the 'bad boy' you were hoping for.” He was really agitated, and they both knew it. “Can I get a drink of water?”

“Sure, glasses are in the top cabinet on the left, over the sink.” Karen was a little surprised at how emotional Chris had become. While he was in the kitchen, she took the opportunity to see who had texted her, figuring that it was Carol. The messages surprised her.

“OMG! The hairbrushes ARE for spanking. Girls!”

and, “Randy says Chris loves you.”

Just then Chris walked back into the room. “Look, if you’re going to dump me, just…”

“You love me?” she asked.

“Um, who told you that?”

“Is it true?”

“It could be. I guess we’ll never…”

Karen took his hand. “I’m sorry.”

“It’s…”

“No, it’s not. You were hoping to fall in love. I was looking to… well…”

“Get thrown on the bed and fucked?”

“Who told you that?”

Chris smiled. “Is it true?”

“Yes. Look, I’m sorry that things didn’t work out…” Chris pulled her to him and kissed her on the lips. She pulled away from his lips, but not his arms. “And I’m sorry if I…” He interrupted her again with another kiss on the lips, but harder. She put her arms around his neck. “And you are the kind of guy that I’d like to fall in love…” This time her words were cut off by his tongue forcing itself into her mouth.

His hands moved down her back to cup her ass, gripping it so tight through her dress that it hurt. He ground his erection against her pussy. She moaned with the passion that he was igniting. The feeling that she felt in her belly when she was holding the hairbrush was back. It became clear to her what she needed to do.

“I haven’t been very nice to you,” she said, her eyes holding his. “I want t … no; I need to make it up to you.”

“How…”

“Wait here,” She said, as she ran to her bedroom. It took just seconds to find a hairbrush. Then she stopped. She liked a man that took charge, and Chris seemed to be that after all. But, was she ready for this? To be spanked? To be spanked sexually?

She went back into the living room. He was sitting on the couch. “Here.” She held the hairbrush out to him. “Spank me.”

Chris held the brush. “No, I…”

Karen lay across his lap. “Yes, you can. I want you to.”

Chris ran his trembling hand lightly over her offering, and she trembled in return. He had to be dreaming, except that she didn’t disappear as he lifted her dress onto the small of her back, exposing a pair of black lace panties. The shape of her pale twin globes was glorious, perfect.

He shifted and her legs parted, just enough to see a hint of wetness in the lace gusset between her thighs. He rubbed her cheeks through just the panties now, and she sighed and squirmed. He drew her panties down; she lifted just enough to help them pass her hips to the crease between her thighs and cheeks.

'He can see how aroused I am now,' she thought, as she let her hips fall back down onto his lap, feeling Chris’ erection pushing into her belly. 'And I can feel how aroused he is.' She felt his hand on her bare skin, caressing each cheek. She arched herself, giving him more to feel; a better target, a better view. His hands were gone for just a few seconds, and then she felt the sting of the hairbrush as Chris delivered the first blow.

WHAP! Chris’ aim was for the center of her right buttock, but it was off and hit the underside, just above her thigh. WHAP! The second was spot on where he had first intended. WHAP! He followed with a third, this time a little higher. The entire side was now a light pink. He was gaining confidence.

WHAP! WHAP! WHAP! Karen let out a little yelp of pain as he now covered her left side with spanks as he had the right. She could feel the heat from her abused bottom radiating into her core. WHAP! WHAP! WHAP! It was the right again, as he hit harder and faster; WHAP! WHAP! WHAP as he returned to the left.

Her ass was starting to smart now; but she wanted more. Her pussy wanted more. She wiggled her ass, as if taunting him. WHAP! WHAP! WHAP! WHAP! WHAP! WHAP! He alternated back and forth between each cheek this time. “Faster! Harder! Spank me!” The words escaped her mouth almost before they crossed her brain. Her pussy was soaking.

Chris’ was amazed at his own reaction to the spanking. His cock was harder than it had ever been. He was torn between the desire to keep spanking Karen harder and faster, and his desire to plow into her pussy. WHAP! WHAP! WHAP! WHAP! The decision was made for him, as he hit her so hard and so fast that he lost his grip on the brush.

Karen was sobbing now as Chris pulled her up from her supine position; she with her arms around his neck and he holding her in his arms as he stroked her back and kissed her hair. “I’m so sorry,” she choked, barely able to breathe as her emotions washed over her. Her ass was on fire, and it hurt to sit on his lap. And yet all that she could feel was his arms around her, and how good that felt. And that her pussy was as hot as her ass cheeks. And that this spanking was what she wanted; what she needed.

Chris could feel the heat from her freshly spanked bottom seep into his legs. He was surprised to also feel her pussy soaking his crotch, and that he was still hard as nails. He shifted, pushing his hardness up against her. As she moaned, his fingers found her hot, wet opening. He looked down into her tear-stained face and softly kissed her as his fingers played havoc in her pussy, along her lips, across her clit. They kissed harder, and harder still, until their tongues were practically wrapped around each others’. His fingers were as talented as she’d hoped they’d be. He found her G-spot, and Karen climaxed.

Karen was now beyond wanting him inside her; she needed him inside her. Unwrapping herself from his arms, she stood, pulling her dress over her head to reveal the hard nipples of her firm B-cup breasts poking through the black lace of her matching bra. It soon joined her panties on the floor as she gave Chris his first glimpse of her soft blonde pubic hair.

Chris stood, kicking off his shoes as he did so; followed quickly by his shirt, pants and boxers. He usually liked to get undressed in stages, but his seven-inch cock, the size of its arousal now quite obvious to Karen, wasn’t in the mood to wait.

She faced away from him and kneeled on the couch, her hands gripping the back, jutting her crimson globes as she spread her legs. Her pussy was so swollen with lust, so dripping with her juices, that Chris’ brain could register nothing else. He was behind her in a heartbeat; his hard-on a heat-seeking missile that penetrated her defenses in one swift thrust. She was so wet, so hot, so tight, that he almost lost his load.

Karen cried out at the force of the insertion. She felt the head hit her deepest part, his girth stretching her beyond anything that she’d ever had in her. His abdomen hit her sore ass just as his balls swung hard against her clit. The pain/pleasure combination was incredible as he grabbed her hips and pulled her on and off his cock, repeatedly striking against both areas as he continued to bottom out inside her. Her whole body was vibrating.

Chris, for his part, could get no end of watching his penis pumping in and out of Karen’s well-stretched pussy; of her red ass shimmying on each thrust. When she had her second orgasm, she was so tight and he so deep in her that he could feel every contraction as she cried out in pleasure. She became incoherent as he continued to piston in and out. This was sex like he’d never had before.

“Cum in me!” She finally screamed. “Cum in me!”

He grabbed her firm breasts for leverage, and drove himself as deep as he could. She was certain that the pain she felt, deep in her pussy, was his cock breaching her womb; that she had never been penetrated so completely; and as he came, that she had never had so much sperm so deep into her. She came with him.

He kissed her neck, her shoulders, her back as he slowly withdrew. She whimpered at the loss of fullness that her pussy had experienced. Chris sat down against the arm of the couch, and Karen snuggled up against him. “You never answered my question,” she finally was able to say.

“You mean, do I love you?”

“Yes.”

“Does it matter if that isn’t… that I’m no … what you’re looking for?”

He was still holding her, and she began to hold him back. She leaned into him and kissed him, softly; her pussy still humming with arousal; his hot load still deep in her belly; the pain in her bottom turning to a pleasant ache. “I think this… you… are exactly what I’m looking for.”