A Friendly Wager | free spanking story

Kathy was surfing the net one night, minding her own business, when she was interrupted by an instant message flashing on her screen, from someone who called himself PhDGary.

A professor...she thought. But no...turned out he was a school psychologist, and had scanned the member directory for females living in the same small town as he, and somehow came up with her name. They chatted politely for a few minutes, about the school system and their kids, and he even gave her some helpful advice about one of her children, who was having problems learning to read.

Soon Kathy looked forward to chatting with Gary, just about every night when they were both online. Kathy had a little fetish, one which she certainly never mentioned to Gary! She liked to be spanked, and no one but her husband and a few online friends knew this. She often frequented the AOL spanking chatrooms, and one night she got a message from Gary, asking her about the chatroom he had located her in...Get the Hairbrush. As their conversations had progressed beyond polite chitchat to franker subjects, she confided in Gary about her fetish, and while he didn't really share it, he was, to say the least, intrigued, and even kiddingly asked her if he might spank her one day.

He asked her quite politely one evening if he might visit her at the real estate office where she worked and take her out to lunch. They were both married so Kathy was a bit hesitant at first. But finally her curiosity got the best of her and she thought what the hell...and the very next day, she met Gary for lunch. He was a very attractive man in his late 40's, with silver- gray hair and an impressive moustache. Over lunch, the two of them bemoaned their respective weight gains over the holidays, and Kathy mentioned she was thinking of joining a local weight control group.

Suddenly a twinkle came into Gary's eye. "Tell you what," he said. "How about we make a little wager?"

"What kind of wager," Kathy asked.

"We diet together...if you lose 20 pounds first, I take you to dinner at the most expensive restaurant in town. And if I lose 20 pounds first...I get to spank you!"

"Not fair!" laughed Kathy. "Everyone knows men lose weight a hell of a lot faster than women!"

"OK then," said Gary. "Just to prove what a gentleman I am, I'll spot you 10 pounds! You only have to lose 10 pounds to my 20...how's that for an offer you can't refuse?"

Kathy couldn't resist. This just might be the little push she needed to lose that weight before the summer...and she was confident she could lose 10 pounds before Gary could lose 20.

As they left the restaurant, Gary said, "Oh by the way, Kathy, this is going to be a fun spanking, nothing sexual. Over my knee in the principal's office, with a paddle...your naughty schoolgirl fantasies come true!"

"Oh really," said Kathy. "You talk as if this is a done deal, like you can't lose."

"I only bet on sure things Kathy," said Gary, extending his hand. "Is it a deal?"

Kathy shook his hand. "It's a deal...and this is one bet you are NOT going to win!"

After their first week of dieting, Kathy anxiously approached the scale for her weekly weigh-in. Four pounds down! Great. However, Gary's loss was twice that! He caught her eye and kiddingly smacked his palm against the back of his other hand and she made an exaggerated grimace.

Week two...Kathy lost just one pound to Gary's four. Oh my, she thought, this wasn't looking good! The third week was the dreaded "time of the month" where she could have subsisted on Ritz crackers and water and not lost a single ounce...in fact, she gained a half pound. Gary, on the other hand had lost three more pounds, for a total of 15 to Kathy's four and a half. "Get that pleated skirt and those knee socks ready" he whispered in her ear.

Kathy made a dramatic comeback during the fourth week, losing four pounds to Gary's one. So now the scales tipped at Gary 16...Kathy eight and a half. The fifth week, it seemed, would be the culmination of their bet.

They arrived together that night, Kathy nervously in line right behind Gary. He got on the scale and let out a whoop. Four and a half pounds lost, bringing him over the 20 pound mark. He had an evil grin on his face as Kathy stepped up. She peeked over the counter, trying to see the digital readout as the clerk weighed her. "You lost a pound" the clerk announced smilingly. "Let's see...that's a total of nine and a half."

Kathy looked at Gary as they left and said nervously, "Well, Gary, I guess you have won, and it's time for me to pay up."

Gary patted her hand. "Kathy, I am absolutely dying to take you across my lap and spank you. It's what has kept me going these past five weeks, eating all this damn rabbit food. But honey, you don't have to go through with it if you don't want to. And guess what...whether you go through with it or not, I'm still buying you that dinner. We've both earned it!"

Kathy was thoughtful. "You know what, Gary...I don't want to back out. I never welch on a bet for one thing, and a deal's a deal."

Gary smiled. "Kathy, I was hoping you would say that! And now the only question is where and when?"

A date and time was agreed upon, and Kathy and Gary were both as nervous as two schoolkids who were being sent to the principal's office for real! He had a key to the school, vacant for the summer, and he carried a duffel bag containing the paddle. She was dressed demurely in a pleated skirt, pullover sweater, knee socks and loafers, and looked years younger than her true age, 41. Kathy had attended Catholic school as a child and paddlings were commonplace. Ironically, she had been such a model student, bright and respectful, that she had never been paddled, not once! But she remembered being strangely thrilled and fascinated when other kids were paddled, not so much because of the pain she knew they were suffering, but because of the embarrassment and humiliation. There was a knot in her stomach as they approached the door to the principal's office. Gary unlocked the door and turned on the lights.

The look of it...the pale green institutional walls...and the smell of chalk and paper took Kathy back to her youth, and she indeed felt like a little girl of 10 again. Gary pulled out the sturdy desk chair and sat down, and rummaged in the duffel bag, withdrawing the paddle.

"Well young lady," he said. "What do you have to say for yourself?"

"I'm sorry," she stammered, cheeks flushed.

"Sorry for what?" he asked.

Kathy thought about that one for a while. "Sorry for that damn chocolate cake I ate during a bout of PMS! I would have won the bet if I hadn't."

"Too late to worry about that now, young lady. Seems you need a little lesson in self control, and we both know what that lesson has to be, don't we?"

Wow, thought Kathy, heart pounding. For someone who isn't a born spanko, he sure learns fast!

"Yes sir, I know," she said in a small voice.

"What do you think I should do to punish you, Kathy?" he said, pulling her closer to him.

"Spank me," she said softly.

"That's right, young lady. A spanking is what you richly deserve for eating an entire chocolate cake, PMS or not!"

Kathy became a bit concerned when she realized she was becoming sexually aroused by the proceedings...and she wasn't even over his lap yet! He was a very attractive man...and the 20 pounds lost had improved his physique immeasurably. She was suddenly quite gratified that she had herself lost almost 10 pounds, considering Gary would soon have a very good view of her ample bottom...well, it was slightly less ample now than it had been five weeks ago!

Their eyes met briefly, and Kathy realized that the arousal was mutual. He tugged gently on her wrist to take her across his knees, and he lifted his right knee to elevate her bottom in the manner of a seasoned spanker instead of the novice he truly was.

They had never discussed the logistics of the spanking. She wondered if he would try to take her panties down, and if he did try, if she would let him. This was totally uncharted territory for him, and he would gauge her reactions as they went along.

Gary began to rub her bottom through the short pleated plaid skirt she wore. Her calves were encased in white knee socks, and he was incredibly turned on by this vision of a beautiful mature woman dressed like a schoolgirl. He reached for the hem of her skirt, hesitating slightly to see if she would protest. When she didn't, he boldly lifted it to her waist. Underneath, she wore white cotton panties, with just a hint of dainty lace around the legbands. Her bottom was lush, and even the full cut panties couldn't hide the swell of her ample cheeks. Her thighs were soft and creamy white, and made him determined to get a glimpse of her bare bottom before this afternoon was over.

"I think your naughty behavior calls for a good, hard paddling, young lady," he said, really getting into it now! Kathy couldn't help but wiggle in anticipation, her legs parting slightly. Gary noticed that the crotch of her panties was damp, and his cock rose in excitement. He lifted the long wooden paddle high, and brought it down lightly on her pantied cheeks...the paddle was long enough to cover both cheeks simultaneously. She gave a little yelp and a nervous giggle...obviously that first swat hadn't done serious damage! Her lighthearted reaction emboldened him to give her a much harder swat the second time...and he was gratified by the loud "OWWW" that greeted it. She began, almost unconsciously, to arch her bottom upwards, inviting another, still harder, stroke of the paddle.

Gary was taken by surprise by Kathy's reaction to the paddling. Here he was, inflicting pain on a very willing woman, and she was obviously enjoying it immensely. As a psychologist, he supposed if he took the time to reflect on this, it would be an interesting case study. But as a man...well, his perspective was quite different. His own arousal, occasioned by indulging in a little spanking play, came as a total shock to him. He was an educated man, a feminist, married to an exceedingly bright, professional woman. He had never given a thought to what it meant to "dominate" a woman. But as he lifted the paddle again and again, bringing it down harder and harder across her plump bottom, he was gratified by her moans, her kicking, her discomfort, and most of all, by his control over the situation. Every now and then he paused in her punishment to stroke her bottom and waited for her reaction. Invariably she lay limp for a moment, in relief at the cessation of the punishment, but after just a few seconds, she became restless, moving about, breathing heavier, lifting her bottom up. This became his cue to resume paddling her, and the cycle began again.

Her bottom was warm now to his touch, even through the panties, and he reached for the elastic waistband and waited. Kathy tensed just a bit, but then raised her bottom up, almost imperceptibly, to facilitate the lowering of her panties. Gary took a deep breath, then tugged them down with painstaking deliberation, the elastic teasing every inch of her soft skin as the panties descended to her knees. He feasted his eyes on the swell of her behind, the tender cheeks already blushing pink, and he rubbed the cool wood of the paddle up and down her buttocks and thighs.

Now that her bottom lay exposed before him, unprotected by even her thin cotton panties, Gary decided to be more conservative when he resumed paddling her. He didn't want to leave telltale bruises on her creamy, supple flesh, nor did he want to hurt her more than she enjoyed. So now he paddled her bare bottom slowly and sensually, pausing between swats to watch for her reaction, and enjoying the lovely rosy color that gradually diffused across the expanse of her fleshy mounds. The teasing spanks to her hot red cheeks were so stimulating, that soon Kathy began to shamelessly spread her thighs and press her swollen clit down against his hard thigh. As she moaned and pressed harder, grinding against him, he picked up the pace of the paddling, delivering short rapid swats to her jiggling cheeks. The paddling set off a chain reaction...each stroke set her body writhing over his lap, each motion of her pelvis pressed against him further stiffened his already swollen cock. The final volley of spanks...a set of ten hard punishing swats...brought her to the edge where pleasure and pain became indistinguishable, and the naughty schoolgirl became a woman again, pushing her body into the throes of an orgasm that startled her with its intensity and duration.

Her ragged breathing and low moans were the only sounds in the room as the paddling ceased. Gary longed to ask her to take his aching cock into her mouth, but he didn't dare. After all, he thought ironically, this wasn't "sexual," right? Kathy could feel his stiff, throbbing cock under her, however, and she thought it unconscionable not to relieve him, not to give him the same sweet pleasure he had given her. She had never sucked another man besides her husband...never...and she felt a pang of guilt that her thoughts were now turning in that direction. She could think of nothing but getting on her knees and graciously offering her mouth in homage to his hard cock.

Oh God forgive me, she thought, all those years of Catholic guilt bubbling to the surface, but something deep within her still compelled her to fall to her knees, and reach for the zipper of his straining trousers. She could smell her own love juices on the fabric of his pants as she unzipped him and eagerly released his swollen manhood. There was something so beautiful about a man's cock, she thought, the way it so eloquently expressed its arousal. A woman after all could cross her legs and act demure...but a man could hardly deny his feelings when his cock was standing straight up into a woman's face, as this one was. It was a tribute, really, to a woman's desirability, when a man's cock strained towards her mouth, needing the pressure of her warm lips around it.

She sighed with pleasure as she took him between her parted lips, and he looked into her eyes as she began to gently suck him. He lifted his hips, thrusting back and forth slowly, and she opened her mouth wider to receive him. His eyes feasted on her glowing face, her expression one of fulfillment as she sucked and kissed him toward climax. How he longed to come inside her warm, pouty mouth, but how could he dare hope for such a privilege, he thought feverishly. He readied himself to withdraw at the moment of orgasm, but incredibly, when she felt his body trembling toward release, she pulled him closer to her, forcing his cock deep into her throat, where it exploded in seemingly endless spurts of hot, pungent cum. She swallowed thankfully as he came, struck as always by the feminine receptiveness inherent in the act. The manifestation of his masculinity...she felt an overwhelming sense of protectiveness toward it as she sheltered his cock in her mouth for some moments even after he was spent.

Gary leaned forward to kiss the top of her head as she buried her face in his lap. He helped her to her feet and she found it difficult to meet his eyes. He lifted her chin, forcing her to look at him, and said, "Thank you, Kathy. That was totally unexpected...and totally unavoidable. So don't feel guilty, honey. It was something that has been brewing between us for weeks, and it just had to happen. And maybe, just maybe...it will never happen again, although that is a very difficult promise for me to make right now."

She declined his offer to take her for the promised dinner that evening. For one thing, she doubted she could sit comfortably on her sore bottom throughout the meal! They were both of them pensive as they returned home that evening to their respective spouses, wondering what would become of their friendship in the future. Both of them came separately to the same conclusion. Their relationship would have to be redefined in light of what had happened this afternoon. Maybe he would spank her again, and maybe he wouldn't. But they would see each other again and soon. Of that they were certain.

A friendly dinner between friends...and then? It remained to be seen.