The $50 bet

Kathy and her friend, Ginger, had a good time together exploring the nearby towns, art galleries, and restaurants. They also had a lot of long late night talks reminiscing and catching up on one another's lives. They were both 36 and couldn't believe that they had graduated from college fourteen years earlier. They both agreed that it had seemed like it was just the other day.

 
Unlike Ginger, Kathy was single and still looking for "Mr. Right". It wasn't due to a lack of looks or personality, both of which Kathy had in abundance. It was primarily due to the fact that she had taken a job teaching at a prep school in rural New England and accordingly she hardly ever met any eligible men. There were a few other male teachers at the prep school that showed some interest, but they were puny, bookish types and Kathy wasn't interested.

 
One day Ginger suggested that they go in town and work out at a gym where she was a member. They made their way into the main workout room and got on adjoining exercise bikes. Within a couple of minutes Kathy's eyes were drawn to a very big and good looking guy who came in and started warming up on the bench press.

 
"Who's that guy?" Kathy asked, motioning with her eyes.

"The one on the bench?" Ginger replied.

"Yeah"

"That's Derek Edwards, he's actually a very nice guy. Last summer I got a flat tire and I couldn't get it changed for like an hour. Then he pulled up and fixed it for me in about ten minutes."

"Did he try to get you to give him something in return?" Kathy asked skeptically.

"No. He was a perfect gentleman the whole time and wouldn't take any money even though I offered it to him. I found out that he was staying in a cabin just a little more than half a mile from us and so I insisted that he come down to our place for dinner. He did and he and Bob hit it off right away. They're both into football and all of that macho stuff so they were like long lost friends. He's a great guy."

"Well give me the scoop, then. What do you know about him?" Kathy pressed.

"Let's see, he's single, 28, straight, and owns his own business. I don't remember exactly where he's from but his parents have owned a cabin up here for years and they let him have it to himself a couple of weeks each summer. I asked him about getting married but he said that he's in no rush to settle down, that he's pretty happy as a bachelor. You can see his cabin from our place. If you want I'll show it to you when we get home." Ginger then excused herself to get some water.

 
Kathy then let her eyes roam hungrily all over Derek's body. He was very handsome with sparkling blue eyes and thick brown hair. He was also a very big man, standing about 6 feet 5 inches tall as compared to Kathy's 5 foot 4 inch frame. Derek was very powerfully built as well with broad shoulders and very muscular arms and legs. She couldn't tell much more about his build than that because he was wearing a baggy t-shirt and shorts. This made her think that he probably wasn't that vain since he wasn't trying to flaunt his physique.

On the ride home Kathy blurted out, "I wouldn't mind having a hot, steamy workout with that Derek."

Ginger began to giggle, "You're so bad!" After they both laughed for a while Ginger added, "Well he's definitely cute, I'll give you that. But unfortunately I wouldn't get your hopes up too high. You're my friend and I think you look great, but the only times I've seen him out with women he's with these gorgeous 20 to 22 year olds, still in or just out of college. That seems to be his type, no offense."

Undaunted, Kathy replied, "Who knows, maybe I can change his mind" and they both continued to laugh some more.

Over the course of the next few days Ginger and Bob encouraged Kathy to stay at their cabin for a few days after they left since they had to get back to work but the school year wouldn't start for another week or so. Kathy didn't want to impose but she did have to admit that the prospect of having the place to herself for a few days was pretty appealing. In the end she decided to accept their offer.

On the last day that the three of them were going to be together at the cabin, Ginger flopped down on the couch next to her friend and said, "Guess what?"

"What?" Kathy asked.

"Well, we've been invited to go down to the Steven's cabin tonight for an end of the summer cocktail party, and ... guess what else?"

"What?"

"Derek is going to be there."

"How do you know?" Kathy pressed, suddenly a lot more interested.

"Well, let's just say a little bird told me." Ginger smiled. "Who knows, the two of you alone up here, each with your own place ... Maybe you should make a move tonight."

Kathy blushed. "Look, you said that he only goes for young twenty-somethings, remember? I'd like to but I'm also not in a rush to get rejected either."

Ginger replied, "I'm just saying, 'nothing ventured nothing gained'."

"We'll see." Kathy replied softly.

Little did Ginger know that Kathy had been working on a plan ever since that day at the gym. She still had a little anxiety as to whether she would actually go through with it or not, but she reminded herself that she didn't have to make that decision right that minute. She would go to the cocktail party tonight but she would proceed according to her plan, not throw herself at him like Ginger had suggested.

Kathy decided that she would dress very conservatively for the party so as not to draw any extra attention to herself. She picked out a long sweater that came past her waist and a peasant skirt that went down to her ankles. Additionally she decided that she would also wear her penny loafers as well as her glasses instead of her contacts. Ginger tried to get her to wear something a little sexier but to no avail. Kathy knew that she had a fair amount of sex appeal but there would be time for that later.

Having attended many fundraising and alumni functions at her school, Kathyn was a master at small talk. She had no trouble blending into the background at the party while acting interested in the idle chit chat that other people heading back to their regular lives tomorrow morning were engaged in. At one point Bob tapped her on the shoulder and officially introduced her to Derek. Kathy masked her true feelings and made some boringly polite conversation. Her main intent was to find out how long he was going to be up here. As he told her that he would be up another five days, she smiled inwardly, maybe she would go through with her plan after all. She encouraged him to talk about himself but she wasn't really listening, choosing instead to steal glances at his hairy muscular chest that was partly visible as the top two buttons of his golf shirt were undone. "He certainly does clean up well" she thought silently to herself.

 
The next morning Ginger, Bob, and Kathy all had coffee together and said their goodbyes. Soon after Ginger had the cabin to herself and plopped down on the couch. She stared at the ceiling for a while and debated her plan some more, would she or won't she go through with it? Getting up she wandered over and picked up a pair of binoculars off the coffee table and looked down the beach. Derek's cabin soon came into view. Nothing was going on there, for now at least.

Kathyn then got changed and decided to go on a long run. Living in a rural area Kathyn spent most of her free time jogging and occasionally practicing her karate. She had earned a black belt when she was in college and occasionally taught self-defense seminars for the female students. As a result she had a very lean and athletic physique which often caused people to underestimate her age from anywhere from 4 to 6 years. It was during her run that she decided that she was going to put her doubts aside and just go for it.

By secretly using these binoculars she had done a fair amount of spying on Derek during her stay and knew his routine pretty well. He worked out at the gym 4 days a week and usually got back after his workout a little after 6 p.m. Upon arriving home he would take a glass of ice water out on the beach in front of his cabin and just watch the sunset and the waves come in.

At about 5:30 she stepped in front of the full length mirror in the master bedroom and gave herself a look over. She had on a white lycra leotard that was slit high on both sides which offered a nice view of her trim legs as well as her bare feet. Her sandy brown hair was combed out and she had done her makeup as well. She had to admit, she looked pretty good.

She slowly made her way about halfway down the beach with the binoculars and waited. After a couple of minutes she saw a light go on in Derek's cabin and she felt a tingling of excitement. Laying the binoculars in the sand she strode further down the beach.

As if on cue Derek came out on the beach still clad in his workout gear just as she was approaching. She gave him a short wave and approached. She said "hi" and reintroduced herself. He said that he remembered her but didn't recognize her without her glasses. They made a little small talk and she smiled to herself as she noticed his eyes stealing glances at her bare legs and feet.

"So, you look like you just worked out, huh?" she offered.

"Yeah" he replied, "Actually I had a new personal best on my bench press today."

"Cool" she said, "And how much weight would that be?" she asked trying to stoke his ego.

"330 pounds" he said trying to sound nonchalant, though a little smile played at the corner of his mouth.

Kathy quickly did the math and figured that was nearly 3 of her that he had just bench pressed, which was a little intimidating. She pressed on, "I guess not too many guys want to get in a fight with you then." she added coyly.

His face became a little flushed and she could tell that he didn't like bragging about himself. Staring at the sand he said, "Well, honestly I haven't been in very many fights. I don't go looking for trouble and other guys see the way I look and figure that it might not be a good idea to fight me and just leave me alone, I guess." He knew that he was bragging a little but he tried to downplay it somewhat.

Kathy knew that now was the time to make her move. "Do you think that you could beat me up?" she asked sweetly.

Derek looked up at her stunned. After several seconds of silence he stammered,

"Why would I want to beat you up? I've never raised a hand to a woman in my life and you seem like a nice person so no, I wouldn't have any reason to want to beat you up at all."

Kathy knew that she had to up the ante. "O.K., I agree. You're right. Maybe I should put it another way. How do you feel about a little wager?"

"What do you have in mind?"

"A bet. I'll bet you say, fifty dollars that I can beat you up within five minutes. What do you say?"

Derek was shocked by what he heard come out of her mouth. He knew what he heard but it made no sense. Here was this cute and petite woman betting him fifty dollars that she could beat him up. He was easily a foot taller and a hundred pounds or more heavier than her. On top of that he had just told her that he had just bench pressed 330 pounds. What was she missing here?

 
"Are you serious?" he asked her.

"Yes I'm serious. Why? Did I stutter?" she retorted.

Derek's mind began to race. Maybe it was he that was missing something. Something was definitely wrong with this picture. He glanced over at her again and she held his gaze and smiled back. She didn't appear to be the least bit nervous or afraid. His ego wouldn't allow him to say "no" and give her the impression that he was somehow afraid of her. Derek didn't want to fight her but he decided that he wouldn't have to. She had clearly said, "within five minutes" so he figured that the best thing to do was to humor her and then use his superior height, reach and strength to keep her at bay for the duration. That way he could keep his ego intact and at the same time make an easy fifty bucks. She might be a little crazy but he would still take her money if she was going to make a bet like that.

 
"O.K." he stammered, "If you really want to do this I guess I'll be glad to take your money." He had wanted to sound nonchalant but his voice didn't cooperate. His mind was still racing trying to figure out what was going here.

"Sounds good to me" Kathy replied confidently as she stepped closer in towards him. "When do you want to start?"

"Whenever you're ready is fine with me", he blurted.

"Say 'go' and we'll start" she smiled.

His mind raced. She seemed way too confident. "Go", he said almost by instinct.

The word was still coming out of his mouth when Kathy sprang into action. With catlike quickness the tiny fingers of her right hand shot out and jabbed into his eyes. Before he knew what was happening Derek let out a howl. Instinctively his hands moved up to cover his eyes as pain seared through his brain. He bent backwards at the waist so as to put more distance between his attacker and his burning eyeballs. Unfortunately for him, this protective motion caused his hips to thrust forward at the same time.

Kathyn didn't rush. Her first blow had caused some damage and he was in no position to defend himself at the moment. Taking a deep breath she gauged the distance and then snapped a sharp kick upwards into his unprotected testicles. Her kick landed perfectly and smashed his balls in between her foot and his pelvis. Derek let out a high pitched shriek as his torso came flying forwards nearly doubling him over.

 
She had anticipated this and stepped in close so that she was now standing chest to chest with him. His eyes were still closed tightly and his hands moved around frantically trying to cover his groin. Unfortunately for Derek, his hands were blocked from doing so since her body was in the way. Grabbing two fistfuls of his t-shirt for leverage, Kathy drove her knee upwards once, twice, three times into his now searing balls. Derek's legs went limp and his body collapsed towards the ground. The pain was excruciating. Kathyn wasn't that surprised at his reaction since she had learned long time ago that a man's true Achilles heel was between his legs. As he fell she kept her grip on his shirt and simultaneously pulled upward and outward shredding his shirt and exposing his torso.

She felt a stirring in her loins as she stared down at the thick pectoral muscles covered in dark curly hair. Her eyes continued to roam over his well developed shoulders, arms, and abdomen. It was a heady feeling seeing this fine specimen of manhood and knowing that it was she that had exposed him.

 
Shaking her head she realized that she had to get back to business. By this time Derek was curled up into the fetal position with both his hands covering his package. Taking aim Kathy delivered a heel kick directly into his solar plexus which forced all of the air out of his lungs with a whoosh. Just as she had planned, his hands slid up to protect the area she had just struck. Hooking her first two fingers on the sides of his hips she pulled his shorts and boxers down his legs, over his feet, and tossed them to the ground. His manhood was now fully exposed and Kathy smiled what she saw. Rising from a mat of black hair was a very long thick cock which hung down between his very large bulbous balls. He was definitely a big man in every respect. 

Turning her attention to his feet she pried off his size 13 tennis shoes and flung them along with his socks off behind her. She then allowed herself a good long look at his completely naked male form lying beneath her. Ravenously her eyes scurried from his chest down to his crotch down his legs and back again. She was getting a little hot and bothered now but she had to stay in character a little while longer.

 
"Had enough or do you want some more?" she snapped.

Derek's hands instinctively cupped around his testicles again, "Please don't hurt me any more" he cried meekly.

"Don't worry" she paused, "Is your cabin open?"

"Yes" he replied, wondering why she would ask such a question.

She jogged towards the cabin and returned a few minutes later saying, "Spread your legs."

Derek was afraid of her inflicting any more punishment on his throbbing testes but he was in no position to resist as his body was still racked with pain. Keeping his hands in place he cautiously moved his knees further apart. He was relieved when he saw her place an ice pack down underneath his groin and gave him some immediate relief from the pain.

"Open your eyes wide" she said next.

Again he complied and she squirted several eye drops into his sore and teary eyes.

"Now drink this" she said as she held a cup of cool water to his lips. He took a few sips and began to relax.

A cool late summer breeze came up off the lake and washed over his exposed body. Kathy then laid down beside him and began gently rubbing her hand back and forth over his chest. Though the pain he felt was still substantial, it began to give way to pleasure as he enjoyed the sensation of her hand stroking his bare chest in the cool evening air. Before long his feelings were betrayed as his cock rose and became fully erect. She smiled a wide smile as she began to realize the power she was exerting over him.

 
She then softly kissed him on the mouth and began to move her hands all over his bare torso. He kissed her back and realized that he was now consumed with passion for her. Their tongues plunged deeper into each other's mouths and they both became progressively more aroused.

Suddenly she pulled away from him and began to stand up. He was filled with a simultaneous fear that she was either going to begin attacking him again or that she was going to leave. There wasn't much time to entertain either of these thoughts as she stood to her full 5 foot 4 inch height and then looked down at him and smiled warmly. She was a vision standing there backlit by the setting sun.

His lust for her caused him to pant as she silently lowered herself and sat upon his taut masculine chest. Leaning forward she pressed her sex down into his face and instantaneously he began to pleasure her with his tongue. His hands reached up to fondle her small but perky breasts as she began to moan softly. Shortly thereafter her moans became increasingly louder and her pelvis began to rock back and forth in a gentle rhythm. After several minutes she felt as if all her internal organs had melted and began to gush out of her. She screamed aloud as waves of pleasure washed over her.

 
After taking a few moments to catch her breath she maneuvered herself back down towards his waist. Gently she took hold of his member and start to jerk it. Derek couldn't believe his luck. The still considerable pain in his balls and lower abdomen gave way to ecstasy as the two continued their lovemaking. Though he tried to last as long as he possibly could, the combination of her beauty and dominance over him was too much. Before he knew it he climaxed inside of her as tiny spasms rippled all through his body.

It was dark now and Derek was about to drift off to sleep when she placed a hand on his shoulder and shook it lightly, "Walk me home?" she asked.

Her question took him by surprise. They hadn't spoken in what seemed like hours and her voice jolted him back to reality. "Uh ... sure" was the only reply he could muster.

Kathy rose and lightly brushed the sand off herself. She stepped over and gathered up all of his clothes and shoes and tucked them under one arm. She then extended a hand downward and helped Derek very slowly struggle to his feet. He let out a low moan as he stood up straight as his genitals and stomach were still considerably sore. Very gently he brushed himself off where he could do so without pain. Other more difficult to reach places would just have to wait. 

She grasped his hand in hers and slowly they made their way out to the road. Derek was walking bow legged in order to keep his thighs from brushing up against his throbbing testicles. They turned left and began walking back towards the cabin where Kathy was staying.

 
It suddenly dawned on Derek that he was walking completely naked down a public road. Thankfully most of the other residents had cleared out a couple of days earlier but he was seized with the fear that it would only take one car to come around a corner and the driver would see him in all his glory. He found it a little disconcerting that she was dressed and gathered up his clothes but never offered his clothes to him, like it was normal for him to always walk around nude. He thought that the two of them would make for a disconcerting sight if anyone saw them: a big naked guy being led by the hand of a much shorter, slimmer and woman in leotard. He then decided that it wouldn't be very long until they arrived at her place and then she'd give him back his clothes so he decided not to ruin the mood by saying anything.

Soon thereafter they arrived at the front door of Bob and Ginger's cabin. As they approached Derek cleared his throat and asked, "Do you mind if I come in for a little while?"

Kathy stood and faced him and said, "It's pretty late, so I think I'm going to call it a night." Then suddenly she placed her ear to his chest and left it there for a few seconds. Turning back to face him she kissed him gently on his left nipple and said, "You've got a good heart, I can tell" and then she turned and opened the door. "By the way" she added "I think I'm going to keep these if you don't mind" motioning with her left arm that still held his clothes and shoes. Derek could only shake his head back and forth slightly. "Great, thanks. Bye" she said and shut the door behind her.

 
Derek stood and stared blankly at the door for a little while. This had truly been one of the most bizarre nights of his life. If someone at the gym had told him that before he went to bed that night that he would be beaten up by a girl in leotard, stripped naked, have mind hand sex with a woman he had only recently met and then made to walk completely nude down a public road he would have said that they were crazy, yet here he was. Slowly he turned and gingerly made his way back towards the road with his crotch still burning and gravel digging into the bottoms of his bare feet. His mind was swimming with questions and thoughts, all of which were about her. Mostly he wondered if he would ever see her again. Suddenly a smile crept across his face, he would have to see her again. After all, he still owed her 50 bucks.