Gambler by Nature

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Betting on love.
5.7k words
4.5
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Detective Allison Marshal slowly rubbed her tired blue eyes as she continued to leaf through the the current crop of applications that were on her desk. The 32 year old divorced mother of one was a detective in the narcotics division was looking for a new rookie to join her squad. Much to her chagrin, the pickings this year were very slim.

She slowly got out of her chair to stretch, and as she did it was easy to see why she was known as the hottest cop on the force. The former colligate swimmer had kept her body in shape by getting in her laps at the local swim club and through her exhibitions as a martial arts enthusiast.

She had long blonde hair fell halfway down her back, long toned legs, and beautiful blue eyes that seemed to light up a room. She was blessed with a pair of beautiful 36c breasts that despite the birth of a baby, showed no hint of sag. Her lower body was blessed with long supple legs, toned from her daily exercise, and encased in a pair of skin tight stretch pants, which contoured her sensual hips and "unbelievable" behind.

As she sat back down she leafed again through the applications and came upon the name Jason Schmidt, for maybe the fifth time. He was tops in his class at the academy after serving 3 years in the marines. He seemed to have all the necessary qualifications, but at just 22 years old, Allison wondered if he was too young. She decided to bring him in the following Monday for an interview in an attempt to evaluate him for the squad.

Jason received the call and made his way to Allison's office at exactly 9am the following Monday.

"Please come in Jason. Have a seat," Allison said as she directed him to a chair.

"Thank you Ma'am," Jason replied as he sat down.

"Well I have seen your test scores from the academy. So tell me why you want to join the narcotics division," she asked.

"Well Ma'am I feel that I could make the most impact in this field. It seems to be a never ending war and I would like to do my best to attempt to ebb the flow of drugs in our society," he began.

Allison burst out laughing.

"Did you read that in a book," she laughed.

"Well I thought," Jason began as he turned noticeably redder by the second.

"Look just tell me what you think ok," she said.

"Ok Yes Ma'am," he replied.

"And Knock off the Ma'am shit. My name is Allison," she said.

"Ok Allison," Jason replied visibly relieved.

After he settled down a bit Jason explained that his older brother was a recovering addict and he saw first hand the destruction that it can do to a family. Also he had a couple of buddies from the marines that had suffered as well, and he wanted to try his best to help stop the flow of drugs and all the danger and pain that comes with it. After about fifteen minutes of talking to him, Allison realized that this was her guy for the squad. He seemed to have all the qualifications and passion needed for a dangerous and sometimes downright unpleasant job. She also noticed that he would blush a bit when she looked right into his eyes, and found the whole thing rather cute.

Jason for his part felt an immediate attraction to Allison, and rested his portfolio binder on his lap to hide the growing erection in his pants. Every time she looked at him he fidgeted uncomfortably in an effort to stop her from noticing his arousal. A battle which was becoming more difficult to win.

"Well Jason what do you think? Would you like to join the squad," she asked finally.

"Oh absolutely Ma'am. Oh I'm sorry I mean Allison," he smiled.

"Good. I'll introduce you," she said as they got up and went to meet the rest of the members of the squad

After a few months in the squad Jason and Allison began to get very close, and often would head out to the bar together after their shift. They began to form a very close friendship, with Allison becoming his confidant and unofficial big sister. She always offered him a female perspective on things and was very protective of him around the other members of the squad. They eventually got to the point where they could share everything with one another, and neither judged the others actions.

Jason for his part was always tormented when Allison told him stories of her dates, he found being with her an intoxicating elixir of passion and heartbreak , and many a night he would fantasize about her naked body wrapped around him, as she rode him until he exploded.

Every girl he was with he compared to Allison and every girl came up short. She haunted his dreams and lingered in his conciseness long after sleep released its grip on him, she was quite simply his ultimate fantasy.

One night after a long shift they went to the bar to bring the day down. Jason was talking about a girl he recently had begun seeing and her lack of enthusiasm in the bedroom.

After a while the alcohol was lowering inhibitions and Allison began to speak up about her experiences.

"Well to be honest with you I have never had an orgasm by a man," Allison said as she sipped her beer.

"You have to be kidding me," Jason replied as he looked dumbfounded.

"No I'm serious. I mean I have had them, but only by manual methods," she replied as she held up a hand.

"I have heard of that," Jason replied.

"As a matter of fact my old girlfriend Kelly couldn't do it without oral sex," he replied.

"Now you are just playing with me," Allison snapped back.

"No I am serious. She could not get off unless I went down on her. True story," he replied.

"You know you have to pay special attention to the regions down there, then things start happening," he laughed.

"I tell you something though, that girl made me perfect my craft down there," he laughed.

"Really," Allison said intrigued.

"Oh yeah! Sometimes I would have to spend the better part of the night down there just to get things started. But after a while you get the system down and it takes 5 minutes," he replied.

Allison suddenly felt a bit of moisture between her legs and shifted uncomfortably on her barstool.

"So now you tell me something that you have never don," she said trying to change the subject.

"Oh I don't know," he replied hedging

"Oh c'mon I told you," she pushed.

"Ok. I have never had sex without a condom on," he replied.

"Never," Allison questioned.

"Nope, Always wanted to, but never got the chance. I guess now you can't be too safe. On the bright side I have never even had a cold," he said as they both laughed.

They talked more into the night and had a few more beers until the football game came on, and when it was over Allison lost the bet and paid the 5 bucks she owed him. After a few more drinks they started to bet on everything, who would go to the bathroom first, what would the person sitting next to them order, until finally Jason had an idea.

"I have a bet for you Allison. That is if you are big enough to take it," he started.

"Yeah bring it on big boy," she replied.

"Well let me start by saying that we both are obviously attracted to each other. And we both like being with each other," he began.

"Yeah so what's your point," Allison said a bit of blush on her face.

"Well what if I bet you that I can give you an orgasm," he said.

"What! What are you talking about," she demanded.

"Well I bet you that I can give you an orgasm. If I lose I will baby-sit Gracie every Friday and Saturday night for a month."

"And if you win," she queried.

"Then I get to make love to you without wearing a condom."

"I'll tell you what I will even get myself tested and abstain from sex until the big day," he laughed.

Allison didn't know how to react, as she was a bit thrown by the whole thing. On the one hand she was very attracted to Jason, but then again there was a large age difference and the department found on office romance. Just as she was about to say something, she thought better of it and got up to leave.

"I'm going home now Jason," she said.

"Wait Allison, look I'm sorry ....I just,"

"Forget it. Look my mom can only stay till 10 tonight so I have to go," Allison said as she headed for the exit like the building was on fire.

"Oh beautiful," Jason cried as he drank his beer.

"I'm such an idiot. Man I blew it!"

The next few days Jason tried to avoid Allison as best he could, but when you work in a squad it is hard to avoid your commander. Wednesday night he was working late as his desk when he got a call, and after a few minutes of small talk Allison got to the point.

"So I have been thinking about what you said," she opened.

"Yeah. Look Allison I am sorry about that. I really over stepped my bounds and I apologize," he replied.

"So does this mean that you don't want to do it," she questioned.

"What! Ahh no I do want to do it. I just thought that maybe you,"

"Because I have been thinking about it and I want to take the bet," she replied. "Are you sure about this," Jason asked her.

"Yes. Now hurry up and come down," she said as she hung up the phone.

Jason made his way quickly downstairs to her office and when he knocked on the door, she told him to enter. He closed and locked the door behind him, as she motioned to a chair for him to sit down.

"Well are you ready," she asked him as they looked at each other.

"Yes. Are you sure you are ok with this," he asked her again.

"Yes," she responded.

At her response Jason approached, and as he pushed her legs apart, knelt between them.

Allison's heart was pounding as he gently pushed her skirt up, exposing her tight blue panties to her new recruit. He smiled at her reassuringly as he gently began to slowly caress her mound through the tight fabric of her panties. A slight moan escaped her lips, and he could feel her heat below his thumb, as he continued to slowly circle and outline her pussy through the fabric.

She leaned her head back and moaned again as his exploration increased to below the waist band, and gentle brushes of her naked sex. He could feel her wetness on his thumb, and saw her knuckles had gone white from gripping the sides of the chair as hard as she could, as he continued his assault.

"Oh God...mmmmn...oh Jason," Allison moaned as she began to feel a pressure building up inside of her.

She suddenly felt a new pressure on her mound and looked down to witness Jason licking her mound through her soaking wet panties. She moaned with pleasure as she felt the satin panties get pushed deeper and deeper into her, and the wicked delight with the front of her soaking wet panties being pulled off the surface of her mound as he pulled back to remove his tongue.

She gazed down at him with lust filled eyes, and when their eyes met, he smiled wickedly as he ripped off her panties, exposing her femininity in all of its glory. She involuntarily shivered as she felt the cool air on her hot, exposed sex.

There before him was the reward he had longed for. He gently bent down and inhaled her sex deeply, the musky scent driving him insane with lust and desire. His desire was taking control of him now. He wanted to taste her, to hear her squeal with pleasure, and so he did.

"Oh my God," she cried as his tongue slid deeply into her dripping pussy.

He began to explore every pocket of her sex, using his tongue like an examination probe he explored every millimeter of her femininity and savored the taste along the way. He plunged his tongue into her deeper and deeper, leaving no region ignored nor neglected.

His tongue teased her labia and massaged her clit, while his finger slid deep up inside of her. He loved the way she tasted, the salty flavor coating his tongue and filling his mouth.

"Oh baby...oh you're so good...oh god...don't lose it baby...oh please......oh please...oh God," she cried as she felt the passion begin to build inside of her.

Jason responded by clamping his hands to her ass and feasting on her pussy like a starving man. His tongue went into overdrive, fueled by all the sleepless nights of desiring his mouth where it was right now, between the legs of his fantasy woman.

She could feel the release coming and gripped the back of his head, while grinding her pussy into his face. He slowly circled his tongue inside of her and gently massaged her clit, as he moved his hands firmly around her waist. She moaned with delight and gently stroked his hair as he continued to feed on her femininity.

"Oh baby yes.....oh please.....God....don't stop baby....oh please.....oh Jason," she cried as powerful waves of pleasure began to form inside of her.

Inspired by her squeals of delight he began to suck on her for all he was worth. He darted his tongue inside of her faster and faster as she ground her sex into his face harder and harder.

"Oh God Jason......oh .....Oh...please...oh.....Goooooooooooodddddddddd," she cried as all of the pleasure points erupted inside of her like one big explosion. Her pleasure seeped throughout her entire body and surrounded her like a warm blanket

She lay back on the chair with her eyes closed and chest heaving, completely exhausted and open as he lapped up all of her juices. When she opened her eyes she was looking directly into his face and was aroused to see it covered in her juices.

"So how did you like it," He questioned her.

"That was amazing," was all she could muster still delirious from her first ever "male caused" release.

"So do I win the bet? Did you have one," he asked her with a wry smile on his face.

"Yeah I think I did," she replied as she leaned back in her chair, unconcerned about covering up for the sake of decorum.

"Ok well then I win. When can I collect," he gloated.

"I have to drop the baby off at my mothers. Come by my house on Sunday afternoon," she said as she got up from her chair and pushed her skirt back down.

"And for heaven sake wipe your face off," she said as she threw him a paper towel

"Oh and Jason," she said as he was leaving.

"Yes,"

"Don't forget to get tested," she winked at him as he left

Jason was true to his word and got tested that evening. He had the results in 48 hours and handed them to Allison on Wednesday of that week. She reviewed them and called him at his desk.

"Dinner at my place on Sunday. Come down to my office for lunch," was the message she left on his voice mail.

"Come in," she called as he knocked on the door.

"Hi Allison, did you see my results," he queried.

"Yeah I did. Ok Jason I will honor my bet," Allison replied.

"Oh my God this is so great! I can't believe this is going to happen," Jason replied as his heart was pounding.

"There is just one thing Jason," she said.

"What is that," he replied.

"No sex of any kind until Sunday," she said.

"You must promise me," she said.

"Ok I promise," he replied.

"I have assigned you a stake out for 4 days starting tonight," she replied.

"Allison I said I would and you can trust me. If this is about me abstaining then," he began.

"No it has nothing to do with that. This needs to be done. You start tonight understood," she lectured.

"Yes Allison," he replied.

"Look I'm sorry but I need my best people on this. Besides I'll make it up to you on Sunday," she said.

"Yeah I know. It's just so far away," he replied a bit of dejection evident in his voice.

"I'll tell you what. How about lunch," she asked.

"Yeah ok. What do you want," he asked.

"Well something high protein," she said as she got up from her desk.

There was a strange look in Allison eye as she walked toward Jason and quite unexpectedly knelt down in between his legs.

"Well what do we have here," she said as she unzipped his pants and slipped her hand inside.

"What if somebody hears," Jason moaned as she grabbed his shaft and began to lightly stroke him.

His inhibitions were quickly flowing out of him as her hand found its mark and began to tease his cock with wickedly erotic strokes. He began to thrust himself forward and match her strokes, as she pulled out his cock. He looked down and saw her smiling wickedly as she licked her lips seductively and spit on his cock.

"Allison. What about the people outside? I don't think we can do this," He said halfheartedly as he felt his beautiful commanders' hot breath on his cock.

"Oh give me just a minute, you know how hungry I get," Allison replied as she inched his cock closer to her mouth.

He moaned as he felt the feel of her hot saliva on his cock and looked down just in time to see slowly begin to lick his shaft. He squirmed as her tongue made her way up his shaft from the base to the head, and when she reached the head, she spit again directly on the head.

"But Ally," was his reply as she pulled him to her and took him into her mouth.

"Oh God oh...Oh baby...Oh yeah," he moaned as she began to pump him harder into her mouth. Her eyes never left his as he witnessed more and more of his cock disappear into her heavenly mouth.

"You know what I want daddy...you know honey...give it to me baby...give mommy what she wants....feed me baby," she said as she popped him back into her mouth and began to suck him harder.

Jason leaned back and moaned deeply as the wonderful feel of his commanders' mouth, combined with her slurping sounds and fuck me eyes, was quickly driving him towards eruption.

"Oh God Ally...oh God...oh fuck...ooh....," he cried as he erupted inside of her mouth.

Her lips formed an impenetrable wall around his cock as she swallowed all his seed and fed of him like a nursing puppy. She lingered between his legs and continued to milk him until she had gotten every last drop, then stood up and kissed him passionately.

"I love the way you taste Jason," she said.

"My god. That was amazing Allison," Jason said as he began to calm down from his eruption.

"Now I think that can tie you over till Sunday," Allison said triumphantly.

"Oh absolutely," Jason said.

"Good I'll see you on Sunday then," she said as he zipped up.

"Yes Sunday," he replied still a bit frazzled as he left.

The four days of the stakeout were the longest days of Jason's life, and so when Sunday finally arrived, he went right from his shift to Allison's house.

He knocked on the door and his heart skipped a beat when she answered. She was dressed in a pair of low cut jeans that clung tightly around her seductive hips, long toned legs, and tight firm behind. The jeans hung low to show the waistband of her thong above the waistband of her jeans.

Her black belly shirt pulled tightly against her skin, and strained greatly to cover her size c breasts, ending just above her navel, and exposing her flat stomach. Her long blonde hair was pulled back, and her beautiful blue eyes were filled with excitement. He could see from her broad smile that she was excited about this as well.

"Well how was the stakeout Jason," Allison asked as she showed him inside.

"It was fine. A bit long, but all in all pretty good," he replied.

"Well I hope you like turkey. I am making it for dinner," she said.

"Are you kidding? Of course I do. It smells delicious," he said.

They made their way to the dinning room, but before Allison could make it to her chair, Jason grabbed her from behind and kissed her passionately.

"Whoa. Hold on their boy. What about dinner," Allison said as she broke their embrace.

"Allison I want you," Jason said.

"I know but what about the turkey," she said as he began to kiss her again.

"Let's have it for breakfast," he said.

Allison could feel the heat between her legs beginning to grow, and as his hands began to press her mound through the tight a single thought came into her mind: Fuck the Turkey!

"Ok baby," she said as she grabbed his hand and led him to the bedroom. As she walked before him His eyes were locked on her perfect ass, and as he saw her tight jeans highlight every perfect inch of it, his cock was making his pants very uncomfortable.

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