Jason was new to the small city in the foothills of the rocky mountains town having been forced to relocate for work. While he enjoyed access to the outdoor activities he had longed for in the city he found himself frequently frustrated with the pace and mono culture of his new environment.
Surrounded by flannel shirts, boots, pickup trucks and Subaru's he felt like the outsider he was. In Orlando his new Mercedes and tailored clothes conveyed his status. Here people rolled their eyes and took every opportunity to disparage how well his car would perform come winter.
The effects of COVID on his life were mixed. He was finally living his dream of living in the mountains while working remote but missed the daily interaction and respect of his employees that fueled his ego.
With little in common with the majority of locals he befriended a small group of business leaders while they offered great conversation and advice on his career progression he missed the physical intimacy of a girlfriend. Turning to the internet and online dating sites didn't help. Everyone local knew each other and didn't use them and everyone else he was interested in was too far away to be practical.
One day while lamenting his circumstance to his elderly friend. She mentioned her single niece Sere had moved home from Miami a couple weeks prior. The Florida connection caught Jason's attention and he asked what she was like. Joyce chuckled at his enthusiasm and explained that Sere never really fit in in her hometown because of her intelligence and drive. Jason's struggled to keep calm as he asked if Joyce thought Sere might be interested in meeting him. She replied, "maybe, I'll ask."
A few days later Jason received a text containing Sere's contact info. A day later he called her and they made arrangements to meet at a small bistro for lunch later in the week.
Jason arrived early to get a quiet corner table where they could talk with minimal interruption. It had been months since his last date and longer since he had felt the relief of an orgasm from anything other than his hand. He was not going to mess this up.
Sere arrived exactly on time and as Jason stood to greet her she noticed his eyes drift across her body pausing momentarily on her ass and breasts before connecting with hers. Amused, she sat and took a sip of the mimosa he had ordered for her in advance. "Nice thouch", she thought.
She explained that she works as a human resources director for a large employment agency in Miami wher her primary responsibilities were conflict resolution and disciplinary action. When COVID started she began working from home and desired to be closer to her aging family and put in a request to relocate.
Jason, wanting to impress talked about his role as VP of finance at a tech firm headquartered in Orlando, his similar journey to the mountains and how he managed conflict in his division. Just as he was reaching the climax of a story describing a incident of cross cultural misuderstanding the witress arrived to ask if theyd like another round of mimosas. Without thinking Jason snapped, "not right now we're talking."
Caught off guard the waitress stepped back to leave and Jason noticed Seres posture straighten and lips tighten from a gentle smile to a stern look. He knew he had messed up, quickly apologized to the waitress and asked Sere if she'd like another. Sere replied, "I think I'm good for now." "It's actually getting later than I thought and I should probably go soon."
Jasons gut sank as he asked the witress to box up the desserts he and Serre had been planning on ordering and asked for the check. Jason followed Sere to her car holding the neatly packed desserts in silence. His mind spinning to come up with a something to say as we watched her perfect ass bounce with every tense step she took. Reaching her car she opened the door and slipped into the drivers seat. With a smiless face she extended her habd to receive the desserd and asked him if he had something to say. Not wanting to show weakness he simple asked, "will I see you again?" She smiled gently as she said maybe before closing the door and driving off.
Two weeks passed before Jason received a text from Sere asking if he would like to join her on a hike at her familys ranch. During that time he agonized over his behaviour and how his ego had cost him the opportuity to hold that perfect ass in his hands as he fucked her until she begged him to stop. Seeing her invite he immediately replied yes with no hesitation. His ego wouldn't interfere again.
He was releived when she answered the door of the guest house where she was staying on the ranch with a big smile and made no mention of the previous incedent. The ranch was 40,000 acres and she had packed sandwiches and water in a backpack for their hike. As they set off she asked him to carry it which he happily did. They walked, talked and laughed for hours enjoying the beautiful scenery of mountains, valleys, elk and deer.
He was exhausted, overwhelmed by feeling of infatuation for this beautiful woman and proud of himself for repairing the damage he had done on their first encounter with having to apologize to her. As they reached the door of the guesthouse she invited him in for mojitos. He accepted feeling confident that he would at least get a kiss.
She led him to the kitchen where as she handed him a knife and asked him to make a charcuterie plate to accompany the drinks. As he worked she placed a drink next to him from behind before wrapping her arms around his waist and periodically steal pieces of fruit for herself and to feed to him.
The feeling of her breasts against his back made him uncontrollably hard and he could feel knees begin to shake and the wetness of his precum when she started to kiss his neck and stroke him through his pants as he worked. When the plate was full she moved their drinks to the heavy wooden table in the kitchen and asked him to bring the food and a couple of plates.
They sat acros from eachother eating in scilence. Sere smiling and staring into his eyes while she stroked him under the table with her foot. Only stopping to refill their mojitos or when she noticed he wsas gettig close to climaxing. In the exctacy of the moment Jason couln't hold the intensity of her gaze. His eyes focusing anywhere but on hers.
After a few drinks Jason asked if he could have another. Sere replied, "yes, I'll make more while you clean up." As Jason began washing dishes, Sere again began strokinghim from behind while kissing his neck. As she rubbed him his hips involuntarily began to move with the rhythm of her strokes. With one hand she unfastened his belt removing from its loops and placing it on the counter before unbuttoning his pants and freeing his penis into her warm hand just as he finished washing the last plate. "Turn around" she requested. As he rotated to face her she adpeptly adjusted and tightened her grip eyes fixed on his. "Take off you pants so I can inspect the goods she said calmly with a mocking laugh.
His pants, still damp from the sweat of the days hike and a breif rain shower, wouldn't fall to the floor freely. Her grip tightened as he adjusted his position trying to help them down . She held her hand firmly in position against each movement so that he felt a sharp pain in his penis with every move and felt it going flaccid. His heart racing with excitement and fear he laughed nervously before gurinting from the sharp pain of a sudden squat to free one leg and then the other.
Sere laughed a genuine laugh and asked him, "did that not feel nice?" Embarrassed and not sure what to say. Jason kept his eyes pointed to the floor and nodded his head, no. Sere, loosened her grip and began fondling his balls with one hand while stroking him with the other. She softly pulled his balls and he moved forward to kiss her. Still averting his eyes from hers he placed his hands on her hips sliding them down across her ass gently lifting her to her toes before moving up her sides to cradle and caress her breasts.
She took a deep biting his lower lip as she pushed him away by his throbbing cock. Using it like a control stick. With renewed confidence his gaze locked onto hers as she asked "you want to get fucked tonight don't you?" "Yes, I do" he said with a smile moving in for another kiss while she held him back.
"I want to fuck you tonight too.Do First I need to clear the air about something though. When we met for brunch you snapped at the waitress. I need you to know that I find that kind of behavior disrespectful to me and women in general. Do you understand?" I do, he replied.
"Good then you'll also understand that I need to know that you will respect me as a woman, my judgement and accept that there are consequences for failure to offer that respect. Do you agree?" Jason nodded yes. His scrotum tight and cock throbbing in her hands as she continued to massage him.
"Are you willing to accept my judgement in choosing the appropriate consequences for your insulting actions?" As he agreed, she released her grip, picked up his belt off of the counter and instructed him to benover the kitchen table. Jason froze, unsure of if his ego would allow him to experience this secret fantasy.
Sere interrupted his thought process stating, "Bendover or get dressed and leave my house." He rested hus elbows on the table with his ass slightly out. "You will lay flat on your chest. I will allow you to hold the edges of the table but you must receive your puishment without moving or making a sound. Do you agree?"
"Yes, Sere"
"Thats another thing. My name is Serendipity. I only allow my friends and family to call me Sere. After your actions the other day you are not yet either. From now on you can call me Sere in public but when we are together you will refer to me as Serendipity and if when you are being punished you will call me Mistress Serendipity. Understood?
"Yes Mistress Serendipity"
She could see the slow drips of precum falling from between his legs as she doubled up the belt and swung it across his muscular ass. Landing with a loud crack his back arched as he yelped and his hands moved to rub wher the contact had been made. As he did she struck again landing a firm blow across the back of his hands and thighs.
"I told you that you must not move or make a sound during your punishment. This is your warning. From now on you will receive 5 more strokes for each infraction. If you cannot control yourself I will bind and gag you as necessary to complete your punishment. You can leave anytime but if you do we are done. Do you agree to these terms?"
"Yes, Mistress Serendipity"
She could see he was hard again and stroked him again until a long droplet of his juices fell to the floor. Then walking to the wall he was facing removed a small canoe paddle while saying to herself just louldy enough for him to hear. "Think we'll start with this."
The paddle was firmer and had less of a sting. The perfect warm up tool. It repeatedly landed with a muffled slap as she alternated between his cheeks periodically tapping his upper thighs. She was impressed by how well he endured the two dozen warming strikes. When she finished. She laid the paddle on the table in so he could look at it and picked up the belt.
It was time for the lesson to begin and the hardon to end. Her first swing landed evenly across both cheeks and while he remained still he let out a loud moan. "Stand up and face me she ordered." "Your moan has earned you the gift of five more strikes and showm me you lack self control. For that reason,I'm going to gag you. Please hand me your boxers or leave my house."
Jason walked over to retreive his sweat and precum soaked boxers from the floor where she has instructed him to take off his pants. He was so turned on anc close to cuming he could barely walk. His entire body shaking from the adrenaline rush. He handed his boxers knowing what was coming next.
"Open your mouth," she directed in a calm business like manner. He did and she stuffed his dirty bioxers in his mouth. He could taste the saltiness of his own fluids confused about if he should be revolted or turned on.
