Part 1: The initial contact

There was no doubt that Scott was a ladies man, but the particular thing that separated him from his other womanizing friends was that he all the time treated his partners with respect and ensured that their sexual needs were met. There were a few one night stands, but that was not by design of Scott, but more of a conscious choice of his lover. More often than not, he had many repeat liaisons with a myriad of women. Scott had a particular type that he was attracted to, but he was not petty in that he understood that all women were sexual, sensual, and had needs. Because of this ideological approach, he found himself in bed with myriad of women of all sizes, races, and sexual preferences. This open minded approach served Scott well. Scott was a 5’9″, 175 lb., athletic brown haired 25 year old man with a healthy appetite for good food, partying, and women. He also possessed an 7.5 inch cock that had a 6″ circumference, coupled with a love for cunnilingus which served was appreciated in his numerous sexual encounters.

One particular Friday night, Scott was at his local pub that he frequented about four days a week. There were not many prospective girls around as they were probably out at the clubs dancing. This was the risk at Harold’s Pub, either feast or famine, but it was still a good night because Rick, the bartender, usually charged for every third drink. Around 11 PM, Scott uncharacteristically decided to call it a night and get a good night’s sleep, so he tabbed out with Rick and headed to the door.

“Leaving so soon?” was heard by Scott as he was leaving the bar area. Scott turned around to see a middle aged woman, plain looking, with shoulder length brunette hair, deep brown eyes, an intense face, with a confidence of self that had Scott doing a u-turn in a matter of seconds.

“Excuse me, are you talking to me?” Scott asked as he walked up to this intriguing woman sitting on the bar chair with her legs crossed and a cosmopolitan in front of her on the bar.

“Yes, I was asking why you were leaving so soon,” stated the mid 40’s aged woman.

“Well, I am here alone, no friends came out, and I figured that I would just go home instead of drinking too much here and then having to walk home. Plus, I might as well get a good night’s sleep since I tend not to most weekends,” stated Scott.

“That’s too bad. I was hoping you would have a drink or two with me. I am Joan and I like your look and if you have no one to hang out with, then you can join me and my friends.”

With that, the man sitting on Joan’s left left his seat and moved behind her to her right and sat two seats down among the rest of their friends. Since Scott had all the time been intrigued with older women, he took a seat, gestured to Rick and was rewarded with another Guinness in short order.

“Put it on my tab,” Joan stated as Rick nodded in affirmation. “My friends and I like to go out to a different bar once a month to get a feel for what is out there, meet new people, and add some variety. I am quite glad we chose this bar tonight.”

“I am flattered and must say that you are a woman of considerable command. I was ready to go, but the look in your eyes when I turned to see who had spoken to me drew me back,” Scott responded.

Scott and Joan talked and drank for roughly an hour and a half. They spoke about their backgrounds, careers, and even spoke of sexual preferences. Joan was divorced and very open about herself, political thoughts, and sex. It was actually refreshing to talk to her as opposed to a woman of Scott’s age where he was constantly fishing for answers and sometimes searching for depth. About a half hour into the conversation, Joan’s hand dropped to Scott’s crotch and she gently rubbed over his corduroy pants until his cock was pushing up near the hemline of his pants. Scott removed Joan’s hand from his crotch and adjusted his cock to point toward his right pocket of his pants so that it would have room to expand. He then took Joan’s hand and placed it back in his crotch. She smiled at him, wrinkled her nose, and giggled.

“I certainly like what I am feeling. Hope you are interested in older women,” Joan whispered.

“I wouldn’t be here if I wasn’t, but somehow I know you already knew that,” he retorted.

This is where they began to distribute ideas more of a sexual nature. Scott felt comfortable with this woman because she already had stated that she would never marry again. She was free, her daughter was in her early 20’s, and Joan enjoyed time for herself. Joan was raised as a Hasidic Jew and was actually in an arranged marriage. She had one daughter and suffered through an abusive, non-loving marriage for ten years. She left her husband roughly 12 years ago, pushed through a divorce, and built a career for herself while raising her daughter. This was now her time and she was not gonna be shackled by any societal constructs made to oppress women. Scott found himself enamored by this woman and reveled in the fact that he had luckily met her in his local hangout.

As the clock ran past midnight, Joan insisted on driving Scott home because he certainly had too much to drink. They walked out of the bar holding hands and Scott sported a hardon that could not be hidden. As Joan glanced down, she just smiled wryly. For a full hour, she had kept him hard at that bar stool and it would not go down. They entered her Ford Bronco and they were immediately at each other, kissing deeply with intertwined tongues like two teenagers. He finally was able to grab ahold of her ample tits which were remarkably still quite firm for a 45 year old woman. Joan put a stop to the make out session and drove the two miles to Scott’s house.

Scott begged Joan to come in the house as he had his own room and his other two roommates did not care as they all the time had their boyfriends over. Joan would not relent, but as he was still pleading, she undid his belt, unzipped his fly, and then finally released his cock. Scott shut his mouth, raised his hips and slipped his pants down to his ankles.

Joan kissed him on the mouth and whispered, “Let me take care of this for you. But you will keep your hands off of my head and I want you to play with those sensitive nipples you told me about.”

She immediately took her hand, placed it at the base of his cock and began to run her hand up the backside with her thumb pushing pre-cum up to her waiting tongue. As the pre-cum began to ooze out of his hole, she licked with the tip of her pointed tongue and took it all in. Joan then licked up the underside of Scott’s cock, slowly, flattening her tongue and lapping at the thick cock. She continued this for a few minutes and then opened her mouth and enveloped the head of his cock with her mouth. She swirled her tongue around his cock head and began sucking and dropping ever so slightly lower onto Scott’s cock. As she sucked and swirled, she continued to to pump the lower half of his cock with her hand, milking him and working him up quickly. Scott continued to squeeze, rub, and draw circles around his nipples as instructed, but then left his touching to tap Joan on the shoulder.

“I said keep your hands off,” Joan said sternly.

“B-but, I am going to cum soon,” stuttered Scott.

“Good, that’s the point.”

And then she attacked his cock with greater zeal than before by driving her mouth down longer and quicker onto his cock so that more than half of his cock was driving into her throat. It did not take long after she increased her pace and Scott began to spurt stream after stream of cum down her throat. Joan sucked greedily and took all of his seed down her throat without letting any precious drop escape her wanton mouth. She then kept him in her mouth as he began to shrink. Once his cock receded, Joan moved her hand to its base and firmly squeezed and rode her hand up to force any more cum out of his flaccid cock. After she completed her last swallow of his seed, she gave him her number which was already written on a napkin from the bar.

“I expect a call tomorrow my dear,” she declared.

Scott pulled up his pants and babbled, “I will, I promise.”

As Joan backed out of his driveway, she admired his ass as he walked to the back door. A wicked grin appeared across her face as she wondered to herself how nice it will be to own that ass.

Part 2:

Scott called Joan at home at 12 o’clock and her daughter, Sarah, answered and said that she would not be home until at least 3:00. Scott called back at 4 and Sarah answered again, annoyed, and then called her mother to the phone. Joan informed Scott that she was pleased that he had called and asked if he enjoyed himself last night. Of course, Scott was beside himself and stumbled through an answer of yes. Joan then asked Scott if he was serious about his sexual desires but Scott was confused and conveyed that he was not what she was referring to.

“Well, my dear one, you alluded to the idea that you really would like to serve a woman. Was that just a crude way of you trying to get in my pants or are you genuinely interested in serving a woman, truly serving a woman and not a little girl?’ Joan questioned.

“Y-y-y-yes, I would like to see what it is like to serve a woman. I love to eat pussy and ever since I was young, I have had dreams, fantasies, and stimulating feelings about a woman in charge, dictating what I do, how I do it, and for whom I do it for,” Scott was able to push out of his breathless self.

“If you would like me to take control of things my dear, then I most certainly will, but you have to figure out that you will not question me, contradict me, or spurn me in any way,” Joan stated matter of factly.

Scott agreed to those terms and swore that he would follow Joan’s instructions and do whatever she wanted. Joan told him to be ready in a half an hour as she was going to come pick him up and they were going out. Joan showed up in her Bronco and pulled in the driveway. Scott bolted down the stairs and out the door to meet his older lover. As she exited the car, he ran up to her enthusiastically and went to grab, hug and kiss her. Joan extended her arm and stopped his advance. She instructed him to get in. Scott followed her instructions and began driving. As he drove to nowhere in particular, she proceeded to unzip his pants, pull out his cock, and then give him another blowjob. After she was done sucking him off and swallowing his entire load, she instructed him to drive back home. She gave him a peck on the cheek, and then instructed him to go back inside, do not touch himself and to have a good night. This scene took place for three more days, just as it had the first time she picked him up.

On Wednesday, Joan showed up again after work and had Scott drive her vehicle. Unlike the prior four days, she did not immediately go down on him. Instead, she pulled his cock out and began to play with him a bit and at the same time she placed her fingers under his nose and had him sniff. Scott finally had the first whiff of her scent and he was overwhelmed by her dense and pungent scent. She placed her fingers on his lips and he unconsciously opened his mouth and sucked on her fingers. Joan then removed her fingers, reinserted them into her pussy and then brought them up to Scott’s nose again, with him wanting to lick again, but she would not place them on his lips. Scott inhaled, all the while Joan was jerking on his cock. Joan then instructed Scott to finger her and then bring his fingers to his nose. As he brought his wet and sticky fingers to his nose, Joan bent down and began to suck his cock. As he drove, smelling her must on his fingers, and enjoyed Joan’s sucking, she brought him to an even more intense orgasm than the previous ones.

“Joan?”

“You can call me mistress when we are alone my pet,” Joan responded.

“Mistress, may I please pleasure you and serve you as a servant should?” asked Scott.

“You will do as you are told and you will certainly serve me my pet, but when I decide, as you are not in charge. You wanted me to control you and I am in control and we will do what I choose, when i choose. Are you upset with what has been happening between us my dear pet?”

“No Mistress, I just wondered that I would be serving you.”

“Patience my pet, Mistress is exploring you and understanding what you need as I make sure that the needs of those who serve me are met as well as my own.”

Again, Joan had a smirk on her face as her plan was working. She knew this athletic, young macho man would try to bottom her in some manner and was unaware of the true idea of being a submissive who would serve a Mistress without question. He was becoming impatient, but she was also conditioning him to respond to her. Joan knew she was not a beautiful woman, but she also understood that she bore a presence and a power of persuasion. The same characteristics that served her well in catapulting her advertising career, also served her well in the bedroom. She was implementing those talents on Scott, and, hey, his cock was lovely, his cum tasted sweet, and she was slowly manipulating him to freely kneel before her.

The next day Joan picked up Scott again, but she maintained the driver role. She instructed Scott to pull his cock out of his pants and present it to her. She went on to compliment Scott on his fine cock and then asked him whose cock it was. Scott was confused and stated that it was his cock. In an instant, she slapped his balls and told Scott to reconsider his answer. She asked him again whose cock it was. Scott took the hint and told Joan that it was her cock. She smiled and continued to drive. Joan pulled into the mall parking lot, but parked a great distance away from any store in a remote area. She instructed Scott to strip and then go in the back seat. Scott was hot, horny, and thinking that he was finally going to fuck this woman. Joan joined Scott in the back seat, turned toward him, lifted her skirt and commanded, “LICK.”

Scott was on her in an instant, lapping her slit and sucking in her juices. He relished eating pussy and he was finally eating out his 45 year old Mistress and relishing each drop of her glorious pussy. Joan enjoyed the intense attention and as she approached her first orgasm, she grabbed the back of Scott’s head and pulled him closer and deeper into her pussy.

“Yes, my pet, worship your Mistress, suck that pussy, make me cum on your face, MMMMMMMM, UUUHHHH,” were the sounds that Joan made as she came for the first of three times on Scott’s face. After she had cum on his face multiple times, Joan bent down and gave Scott his daily blow job. Scott did not last long and blew a large load into Joan’s wanton mouth. After he was done cumming, Joan released his cock from her mouth and kissed her way, closed mouthed, up Scott’s body. Once she reached Scott’s lips, she pulled him to her for a deep soulful kiss. When she opened her mouth to kiss, Scott was introduced to his first taste of male cum. Joan shared his entire load with him and Scott knew he should swallow obediently. After they lay in each others arms for a bit, Scott was instructed to dress, and then Joan drove him home.

Friday reverted back to most of the other days. When Joan picked up Scott, he was already rock hard as he neared her vehicle. Joan exited the driver’s seat and Scott was instructed to drive. As he pulled out of the driveway, Joan immediately released his cock and began to stroke him. She raised the hem of her dress to expose her pussy, already wet and the scent of her in the air.

“Play with my pussy pet and jump on the highway and drive toward the city.”

Scott did as ordered by inserting two fingers into Joan’s pussy with his middle finger pulsing against her g-spot as his thumb rubbed her clit. Scott brought his lover to a quick orgasm and as his hand became a bit tired, he began to pull his fingers out. Joan squeezed his balls firmly and stated, “Do not stop until you are instructed.” Scott continued to play with her pussy until she came two more times. At this point, Joan instructed him to bring his hand to his nose and continue to breath in her aroma. Joan then instructed Scott to turn around and head back home. As he drove, still smelling his fingers as instructed, Joan sucked on his cock and then intermittently would release him from her mouth and just play with him. Scott thought that he would cry from the frustration of Joan’s edging, but he knew that it was a matter of time until he was blowing his load in his Goddess’s mouth. As they turned into Scott’s driveway, he still had not cum yet. Joan released him from her mouth again and then folded his cock back into his pants and zipped him up.

“Now listen pet, if you are truly serious about serving me, then you will demonstrate that you are ready to take the next step. You are not permitted to touch yourself nor are you permitted to discover some slut to take care of your needs. You are to stay in tonight and think only of your Mistress and whether you truly want to serve her. If you choose that you want to serve me, then you will call me when you are through with your coaching duties and I will give you my address. You will be coming over tomorrow to stay overnight, so be sure that your schedule is clear through Sunday afternoon. If you do not call me, then I know that you are not truly serious. You may now go inside.”

Scott stared at Joan dumbfounded as she grinned at him with a wicked smile. He said nothing and she stared at him with a knowing look. After exiting the Bronco, Scott walked to his back door, never looking back, frustrated, confused, and more sexually excited than he had ever been in his life.