Tess seeks long-term friend to help her atone for her sins
Author's note: this story gets off to a slow start - I do hope the build up was worth it for you. Although purely fictional, Tess is based on a real person. If she ever reads this she will know it is about her.
Tess knew she was different from a very early age. She came from the usual dysfunctional family - the product of an alcoholic dad and a mom who never saw or heard anything. It wasn't so much that she was physically abused, she wasn't; it was the emotional abuse.
Tess was always a little taller for her age and a lot smarter. She excelled at sports but always found a way to lose at the last moment. Her winning was like a slap in the face to her dad as he felt she was purposely upstaging him. What a fucked up way to grow up.
In college Tess did well academically. Since she saw what drinking did to her family, she refused to go out and party with her friends, opting instead to stay in and study. On those rare occasions when they could get her out Tess could nurse a beer like a pro. Her biggest fear was to get drunk, pass out at a frat and be the talk around campus the next day. Although she had had a few boyfriends in her life, she never - never let them get anything from her. Despite that, her dad still called her a fucking slut. She never wanted to give him the chance to hear that she had been fucked at a party.
After college Tess accepted a job out of state, all the way to the other coast. The physical distance, although significant, could not completely free her of the mind games they still played on her. But at least it was better than being at home. She was able to slowly reduce the number of calls back home to just once or twice a month.
Tess poured herself into work. She also spent her free time getting her MBA. She thrived in the challenges that were brought before her. She could out work and out think all of her peers. The problem she had at work was that she was not seen as a "team player" as she would not go out drinking or partying. Tess was never on the inside of things, never privy to the "in crowd". She couldn't stand the two-faced gossip that some of the other staff seemed to live for.
The good and the bad news of the manager she worked for was that he knew how hard she worked, hell he counted on it, but he refused to let her go to another department or move up the corporate ladder. Her hard work made him look good to upper management. He was able to climb the corporate ladder just by abusing her desire to be perfect in every project he threw at her. Those who knew her would pick up very quickly that Armand replaced her daddy. Rarely gave her praise and often belittling her in front of others.
Jason joined the ranks shortly after Tess had started. He was hand-picked by Armand because he showed a key insight into solving problems. The only reason Jason agreed to work for Armand was that Armand was a rising star and Jason would be able to get put on some really great projects. Knowing Armand hated doing any work himself, Jason knew he would be able to run the projects his way. "Give me three years and I am going to leapfrog his ass," Jason thought to himself.
The projects came fast and furious. Armand's special gift was putting himself in front of high-profile projects. He knew that his team would work night and day to deliver the projects on time, and at a level of sophistication that no other group could even begin to produce. Jason and Tess were typically working sixteen hour days, six or seven days a week. They worked well together. Working that closely for such long periods of time made them very close. Their closeness never turned sexual. Jason felt like a big brother to Tess. He was very protective of Tess. And Tess felt very safe with Jason around.
They often found themselves talking about their lives. Jason knew that Tess was a virgin. He understood how vulnerable she was emotionally. He nearly beat the shit out of Burton when Burton had tried to seduce Tess only to make fun of her in front of everyone at how bad of a kisser she was and that she wouldn't put out.
A few years into it, Armand became concerned that Jason was going to jump over to another manager. Fearing that Jason would spill the beans that it was Tess and Jason who did all the work, Armand accused Jason of slacking off and using his work computer to surf the internet. The only reason Jason had to use the internet was to do his shopping online because worked so much. Of course, had anyone checked Armand's computer, they would have seen all of the online games he spent his time playing.
Fucking Armand did everything he could to keep Jason from getting another job. It took a while but Jason was able to land another job, well below his skill set and former pay. But, at least he was working again. Tess couldn't afford to lose her job so her only choice was to do nothing but bury her head in work and act like she didn't see the shit that was going on around her; her mother had taught her how to cope with an ugly situation. Jason knew it Tess would catch hell if Armand had ever caught them talking or emailing her so he decided it was best to move on.
In less than a year, Armand decided it was time for him to jump ship. Unfortunately for him, I was already on the ship. So as not to get too far off track here, suffice it to say that Armand was here for too long before he somehow got caught with some company funds that were not his.
A few weeks later Jason received a call from Tess. Turns out that as shitty as a boss that Armand was, at least he valued the work that Tess could do and trusted her abilities completely. The same could not be said for the rest of the company. They had no idea of the value Tess brought to the table. They bumped her back down to the Admin pool and cut her pay. The petty politics in the Admin pool were driving her crazy. The cut in pay was just salt in her wounds. She had given so much to the company, all the late hours, all the details she tracked and the customers she saved were all for naught. Since Armand had taken all of the credit no one knew her skills and value.
It didn't take long before Tess found herself out of a job. With the economy so screwed up and companies laying off so many workers, the only thing she could find was a part-time gig at one of those big chain restaurants serving tables at night.
For the next couple of years Jason tried every way he could to help Tess find a job. They would connect every couple of weeks. Inevitably, Tess would end up breaking down into tears. Jason would do what Jason could do - comfort her as best he could. He would treat her to lunch, pay for her to go to events to make connections, and pick up the phone when she would call at two in the morning complaining about her shift - When-Harry-met-Sally-esque. Tess finally secured a decent job at a large company.
Jason had hoped that this new job would finally make Tess happy, it didn't. One night while Tess was sobbing about her work and how she felt worthless at her job. As much as Jason cared for Tess, he was sick and tired of her "Poor me" attitude.
Finally Jason told her, "Fuck it, Tess. You need to grow a set of balls and quit whining. I'm exhausted and need to get some sleep. Good night."
Jason couldn't sleep well so he logged onto Lush so he could read some stories and maybe cyber with some of his lady friends. Lush was a good place for him. He not only read some great stories and chatted with some amazing women but he also wrote quite a few stories. Chatting, however, gave him the greatest pleasure. He was able to explore his sexual boundaries...which were surprisingly quite broad. He played daddy, dom, sub, son, brother, and basically anything that turned his partners on. He especially enjoyed being dominant. It was so natural for him.
This night he was able to connect with SubtleT. She was single and loved to be dominated. Within 20 minutes both had gotten off, signed off, and dozed off.
A couple of weeks later Tess called Jason and invited him to lunch at Radius on High street - their Maine Lobster BLT was to die for and worth every penny. When Jason arrived, Tess was already waiting for him. When he made his way over to the table Tess stood up and gave him a friendly hug. Tess was in a black/brown Ralph Lauren sleeveless printed dress that showed off her body very nicely. Despite the warmth of the restaurant, Jason took notice of Tess' nipples protruding from her chest. He was taken aback as he had never really thought of Tess as being a sexual person nor had he ever had anything but brotherly thoughts of her.
They chatted for a while as they waited for their lunch to come out. Jason sensed there was something Tess wanted to tell him. She was a bit fidgety and wouldn't look him directly in the eyes. "Is there anything wrong, Tess? You seem a bit anxious today."
"Um...yeah...I guess," she said as she picked at her salad. "I wanted to apologize for not standing up for you when Armand got you fired. I haven't forgiven myself. I'm sorry," she half whispered as she brought her hands up to cover her face in shame. "I...I...just couldn't say anything. I was just so scared when it all came down."
"Don't worry about it," Jason replied.
"No! It wasn't right. I should have said something. I was bad. I wish I could take it all back."
"OK, how about if I spank you," Jason said laughing, trying to lighten the mood.
"I would deserve it. I deserve to be punished," she responded.
At that point Tess nervously looked up at Jason. It was the first time since he arrived that she actually looked him in his eyes.
"Hmm," Jason thought to himself feeling a stir in his lap. "Would that make you feel better?"
"Yes," she whispered barely audible to even herself.
"If you are serious about this, then I want you to go to the ladies room and remove your bra and panties. Bring them back here and set them on the table," Jason told her.
Tess placed her napkin on the table, rose slowly then walked straight back to the restroom. For the first time in all the years they knew each other, Jason took notice of Tess' body. She was tallish, maybe 5'-8", 135 lbs, auburn hair down to her shoulders, a tight ass (she took Tae Kwon Do) and a very firm D cup.
A few minutes later Tess walked slowly out of the restroom. She looked like a nervous deer in the woods full of wolves. Her eyes were cast down and you could tell she was clutching something black in her hands. Her tits jiggled with each and every step. Her nipples had regained their stance and could be easily seen through the bodice of her dress. Jason stood and pulled her chair out for her. As he pushed in her chair he leaned down and whispered in her ear, "You need this, don't you?"
"Yes" came her quiet response. It was a response of relief, of yearning, of desire, of trepidation, of caution, of excitement, and of need all wrapped up in a single syllable.
"Tess, I know you better than anyone. I will do this because I love you as a friend. You will be safe but I will help you to test your limits."
A single tear rolled down her right cheek. Jason wiped it with his finger and brought it up to his mouth tasting her salty tear. Taking his seat he began eating salad once again. Tess wasn't sure what she should do with the lingerie she held tightly in her hands so she just kept holding them. She felt completely exposed despite having the dark dress on. She could swear that everyone knew what she had done and that only a slut would have done such a thing in public. She had never, NEVER done anything like this before. She never even thought of doing something like this and yet she had never been so turned on.
"Are you wet?"
"Yes" came her reply.
"I want you to place your bra and panties on the table. Do you understand?"
"Yes" she replied but hesitated as the waiter was coming with their lunch and she could swear that the people at the next table over were staring at her.
"That was not a request. From this point forward, for as long as we both agree to do this, you do what I say and when I say it. Now put your bra and panties on the fucking table."
As quickly as she could, without trying to be noticeable, she lifted her hand onto the table and placed her most private clothing on the table between the two of them. The waiter smiled at them both and walked back to the kitchen.
"Since you are new to this, my dear Tess, I am going to keep your punishment to a minimum. Keep in mind, that from here on out, your punishments will be severe and delivered promptly. Hike up your dress and spread your legs."
Tess obeyed immediately. Her heart was thumping in anticipation. Her pussy was flowing and she thought for sure she was going to leave a puddle. Oh God! She could smell her own sex!
"Take this carrot and make yourself cum" Jason ordered, handing her a leftover baby carrot from his earlier salad.
Again Tess obeyed immediately. As she began to play with herself in the middle of the restaurant during lunch with a carrot, Jason pulled out his phone, lowered it beneath the table and took a video of the secret action.
Tess began to breath heavily. She was driven on by her need to do as she was told. The cold carrot teased her clit over and over again. She slipped it into her dripping cunt. With her other hand she gripped the table tightly. Her eyes closed and she let out a soft deep guttural moan. When she finally came down from her high she opened her eyes and saw Jason beaming at her. She new she did well.
The waiter came over and asked them if they saved room for dessert. Jason declined and asked for the bill. He placed three twenty dollar bills on top of her lingerie and escorted Tess to the door. As he walked her out he kept one hand on her ass the whole time. As they walked past a table with four well-dressed businessmen, Jason lifted her skirt up so that she showed them the bottom of her bare ass...making them all glad they chose this restaurant for lunch.
Jason told Tess to call in sick for the rest of the day as he had plans for her. When they got to his car, Jason opened her door for her and helped her in. As he did, he told her to hike up her dress. He wanted easy access to her charms. The drive to her place took only minutes but did offer a few chances for her to show off her moist pussy to more than a few people in other cars and some pedestrians. Each time someone could see her pussy, the wetter it became. The last three blocks she had Jason's fingers rubbing her clit. Unfortunately for her, he ordered her not to come.
When they arrived at her condo, Jason ordered her to strip and just stand in her living room. He positioned her so that her hands were behind her head with her chest thrust upwards and her legs slightly opened. She was both terrified and excited at the thought that one of her neighbors would be able to see her through the half-opened windows. She could feel her juices running down her legs. It took every ounce of self-restraint to keep her hands from away from her pussy.
Jason, in the meantime, walked into her bedroom and searched through her bedside stand. Within seconds he found her dildos, the lube, and some romance novels.
He turned on her computer and went through her search history. He discovered her naughty little secrets; the secrets that she watched porn quite often. Porn that featured spanking and a little bit of Dom/sub. She was also frequenting a site with which he was intimately aware, Lush. When he clicked on link to take him to the site, he noticed an all too familiar profile pop up - SubtleT. "Very interesting" he thought. "I know exactly what she likes as we have role-played quite a bit over the past several months...and all of it on the kinky side"
Jason returned to the living room to find Tess exactly as he had left her. He sat on the couch. "Grab me a beer from the fridge" he told her. As Tess turned around and started to walk towards her kitchen, he ordered her to get down on her hands and knees and crawl to get it. "But first, crawl over here as I have something for you"
Tess crawled over to where Jason was sitting on her couch. In his left hand he held her butt plug. In his right, a tube of lube which he set down on the side table. "Suck this. I don't think you deserve to use any lube for your earlier indiscretion. Do you?"
"No sir," she said ashamedly while realizing that she had better get plenty of spit on the plug if she was going to have any relief from when it got shoved up her ass. Taking the butt plug in her mouth she began to lick it. She wished she had done a better job of washing it but then thought that she really did deserve this. She had been bad and needed to be punished.
Once it was wet enough with her spit, Jason took it from her, ordered her to turn back around and spread her ass cheeks apart. With her head turned to the side on the carpet Jason grabbed the back of her hair and began shoving the butt plug in her ass. As soon as the tip of the plug touched her rosebud, Tess let out a little whimper. As he shoved more of it up her tight ass a deep moan escaped from her lips. Finally the plug pushed its way completely into her ass.
"That's better. Now go get me that beer. Don't you dare let that butt plug fall out."
Tess felt like a dog fetching its master a stick. As she crawled out of the room Jason watched her ass intently. He loved seeing the black butt plug as it moved about from her slow crawl to the kitchen. When she finally reached the kitchen, Jason told her that she was to walk slowly back into the living room with his beer. He love to see a beautiful woman try to walk as normal as possible with a butt plug shoved up her ass.
She handed him the beer and instinctively knelt down beside him. "Tess, I have been giving our little conversation in the restaurant some thought. I agree completely that you need to be spanked for not trying to help out when I was fired a few years back. You shall receive fifty swats for your gross indiscretion. I saw a nice wooden hairbrush on your bedside stand. Please retrieve it for me."
Tess crawled into her bedroom and grabbed the hairbrush. She began to get up to return to the living room but realized that Jason had not given her permission to do so, like he did with the beard. She thought it best to crawl back in with the brush in her mouth.
"Very good, Tess" Jason told her as he patted her on her head. Tess felt very proud of herself at that moment. Strangely, she could not remember the last time she felt proud of herself.
While Tess had been away, Jason had found some binder clips sitting on her desk. He also found some extra sets of keys there as well. So when she delivered her brush to him, to be used for her own punishment, Jason had her sit up facing him. He leaned down and kissed each breast. Her nipples were beautiful, like long pencil erasers standing proud just waiting for his tongue. Her nipples had always been sensitive. She had on more than one occasion made herself cum just by playing with them.
Jason flicked them with his fingers. It sent chills down her spine. When he grabbed them between his fingers and thumbs it startled her and she let out a little squeak. Then she saw the binder clips sitting on the couch next to him. Out of curiosity she had actually tried putting one of them on her nipple the year before. As soon as it clamped down, the pain was so intense that she couldn't take it off fast enough.
Jason grabbed her left nipple and pulled it toward him. With his free hand he opened the clamp and released it just behind her nipple. It hurt like fucking hell and she instinctively pulled away from him. Jason grabbed the binder clip and pulled her back towards him saying, "Tsk, tsk, tsk. That just cost you an extra five swats. Do it again and we will add another ten on top of that!"
He took her right nipple and proceeded to do the same thing, though this time Tess remained perfectly still.
"Very good, Tess. You are a quick learner. I am very proud of you." Tess beamed at the compliment.
"Now Tess, you are to receive fifty five swats. I want you to drape yourself over my lap with your head facing to my right. You are not to do anything to prevent me from swatting your ass in any way. If at anytime you make that mistake we will add another ten swats to your punishment. Further, you are to count each stroke for me and you are to thank me for each one. Failure to do so will require us to start over from the beginning. Before I do so, I have one more thing to add." With that Jason took out the heavy sets of keys and attached them to the binder clamps. A sharp jolt of pain coursed through her boobs, but she did not make a move or a sound.
When Tess had positioned herself correctly, Jason couldn't help himself and massaged her buttocks. He leaned down and kissed each firm cheek. He couldn't believe what he was really about to do. He just knew that she absolutely needed this. She needed this from him.
Grabbing the hairbrush Jason raised his left hand and began with the first swat. It landed squarely on her left cheeks. Tess jumped a little from the suddenness to the sting. Her first instinct was to rub her bottom, but she knew better. "One, sir. Thank you sir." she said.
As Jason continued administering her corporal punishment, Tess began to moan. Within ten strokes she had her first orgasm. Not only was Jason's leg getting soaked but so was the brush. Half way through the punishment Jason stopped to take a good look at his work. His pant leg was soaked with her cum. When he stuck his two of his fingers in her pussy she let out a deep moan and came once again bucking on his lap with wild abandon. He pulled the butt plug from her ass and shoved it directly in her mouth. "Do not drop it when you count each stroke."
As he began the swats again it took all of Tess' concentration to mumble out the count and to thank him without letting the butt plug fall from her mouth. At this point the orgasms came one after another. As one was beginning to wane another was started. Tess had never experienced anything like this at all in her life.
When it was finally over Jason rubbed her bright red ass for at least the next ten minutes. He gingerly kissed the spots that needed some extra attention. When he was done, he removed the butt plug from her mouth and set it on the side table. He pulled her up to him and embraced her in a warm loving hug that made her feel safe. She finally felt that she could let go of the guilt that had been haunting her. All was forgiven.