Life the Easy Way 02 - Dating

A few weeks after Jessica started her job and after countless attempts at trying to date the girl of his dreams; daily coffee runs for her, meals paid for and rides reimbursed by him. Brian finally still could not believe she said yes.

Jessica for her part was amused at his virgin attempts in pursuing her and only agreed after seeing the lavish gifts he had splashed on her. She had wanted to see how far she could break him. This does not mean anything in their relationship had changed. Nothing at all, in fact if anything changed, it would be that the teasing had gotten more intense! A sugar daddy! Or a sugar dummy in this case!

On this day, Jessica hopped up onto the side of his desk, causing her skirt to rise up and expose her beautiful thighs, as her legs dangled off the top. Brian could not help but repeatedly looked over at the sight of feminine glory. It was not long before Brian's cock was rock hard and tenting in his trousers.

'Lock the door, and come over' Jessica purred.

Brian rose with a crimson face, showing his tent to her gaze as he shuffled towards the door. He stood before her like a schoolboy even though he was older than her by at least 10 years.

'I noticed that you were staring while I was out the office with the other guys, is that little cock hard from looking at me? Aren't you making it too obvious? What did I say about keeping the relationship private?' Jessica continued purring. Sure the office had their doubts, and she relished the power she had over the other guys keeping them on edge and guessing her relationship status, not daring to approach but at the same time, receiving painful reminders of what they were missing out on.

Before Brian could apologize, her leg suddenly rose up quickly and her shoe kicked him right in the balls.

He fell to his knees, gasping for air and feeling sick in his stomach. As he knelt before her, recovering from her kick, his cock was still hard and throbbing in excitement.

Brian was really turned on from being put in his place with that sexy foot, and being on his knees before this superior woman!

'You obviously need to learn some respect for your better' As he knelt there, his eyes were level with her pretty knees, when she brought her foot up to his mouth. 'I want a proper apology from you Brian and you can start by kissing my feet.'

In adoring obeisance, he kissed the shoes of her feet. She then put her shoe on his face, and pushed him away. 'I have been on my feet all day all thanks to running your stupid work, I want you to remove my shoes.'

In total sexual heat, Brian removed one shoe and then the other while mumbling apologies.

His submissiveness has been completely brought out by her. Without realizing how openly he was displaying her surrender to her, he unthinkingly put his nose in her shoe and inhaled. The odor of her musky shoe was like aphrodisiac to him, causing him to groan with desire, she giggled at his reaction to her foot.

'My oh my, I think you have a crush on my feet. Jessica laughed. 'Take off your trousers, just checking to see if you remember our no underwear for you rule.'

Standing up and removing his pants, Brian stood before her showing his erection.

'How sweet, you are listening to my rules after all' Jessica laughed, as if there was any doubt that he would disobey her. She raised her leg and snapped her foot at his balls again. 'But you should be kneeling' as he dropped to his knees from the kick, wheezing from pain and sexual excitement.

The last kick was with her barefoot, and his balls could feel the shape and fleshy softness of that exquisite foot as it struck his testicles.

Brian realized that the blows from her had caused quite a pool of pre-cum to form at the tip and was dripping out.

'Brian, I think you are attracted to my feet, why don't you ask them out for a date?' Jessica giggled, the humiliation was obvious.

Brian willingly complied and promised her feet a pair of new shoes if they allowed him to date them much to the delight of Jessica, this was too easy!

'Aw you are so sweet!' Jessica laughed at his lack of self respect. 'Go ahead and make out with them, show them you are a good kisser.'

No further encouragement was needed, he gently held a foot, and lovingly gave repeated kisses to first one foot and then the other. Brian was getting really attracted to her feet thanks to her subtle promptings and could not stop himself from really worshiping them. His tongue darted between her perfectly shaped and manicured toes. She was a Goddess and he was just lucky to be there to worship her, at her beautiful feet.

At one point, Brian looked up and saw she was smiling in triumph because she had so easily conquered him with just her feet. As usual. That look caused him to shiver in sexual heat as he submitted to her powerful female dominance.

'Brian, my feet needs to know that you will be a good lover. They heard that you had a less than average penis which is totally not acceptable but maybe your passion might win them over.' Jessica sang. 'Go ahead and rub your penis on them.'

Brian was faint from her tone, her words, her teasing, her scent and her presence! He spread his knees and mounted her foot. His penis was humping the top of one of her dangling feet. As he was sawing his dick across her foot, Jessica decided to have more fun.

'Oh no, my other foot is feeling left out, you better watch out' No sooner had she said it, her other leg snapped out at his balls. 'See what I mean? You better love the other one too!' she giggled as if she was not at fault. Watching him groan in pain but obvious arousal, as he mounted her other foot. This went on for several cycles, first humping one foot, getting kicked in the balls, and switching to the other foot. Each kick caused his pre-cum to leak even more.

'Brian, you are behaving like an excited puppy who humps my legs' Jessica declared proudly. 'Are you my puppy dog, Brian?'

"Yes, Go-Goddess J-Jessica' he spluttered, the works came out naturally.

Jessica beamed, she patted him on the head for calling her Goddess without her prompting, another step towards total submission. This action of hers, went on to cause him to hump her foot with more fervor, as Jessica took delight in delivering quick successive kicks to his balls.

Sensing his impending orgasm, Jessica decided to add another touch, she lovingly pushed his head to rest on her pretty knee, as he continued his frantic humping. 'That's my good doggie.' she cooed. Creating a tender moment for him, as she watched him put his lips to her knee and kissed it in appreciation for allowing him to have sex with her foot.

Most men would run at that point, most would be in total fear or disgust if not anger and indignation that a young girl would do something like that to them. But Jessica Mercedes had seen through Brian and manifested a perverted reaction in him, molding his submission to him at her will. Jessica's humiliating judgment of his inadequate manhood, his inadequate character was the ultimate control and dominance this young girl had over Brian. And she was not done with her pet project yet.

Brian exploded in orgasm on her foot. He froze mid hump, as cum dumped out in multiple spurts from his ball sac to her foot. It went on for far longer than his previous lonely masturbation sessions of one or two squirts. He held on hard, trying to control the trembling from the force of his orgasm.

Hearing Jessica's laughter at his self debasment caused a rare occurrence to him, a second orgasm. He felt his cock and balls began to tingle, and he returned to frantically humping her foot, he was in an emotional state and wanted this young girl to have complete rule over him. 'Oh Jessica, please let me be yours. Please! You own me!' Brian then went over the edge again, and his balls went into convulsions in a pitiful attempt to pump out more cum, but none came.

It was a dry orgasm as Brian screamed in pleasure, and babbled incoherent statements of love and devotion to Jessica.

Jessica Mercedes cradled his head on her knee and just laughed.

--

The week flew past and Jessica did give Brian little treats throughout, she seemed to be focused on her phone constantly and Brian had no courage to dissuade her from it. He would fetch her tea or coffee throughout the day and she would allow him to kneel beside her and massage her legs barely acknowledging him. There were a few times where she kicked off her shoes to show her perfect bare feet and Brian could not resist and kissed them in hunger as he moaned in lust. Brian was used to her distant attention, he knew that he was to work hard to prove his loyalty. Jessica was smoking hot and knew what a challenge it was to keep his spot at her place.

On Friday afternoon, there was a shuffle of activity outside his office as everyone prepared for an important event. Earlier in the day, Brian had seen Jessica in her usual tight fitting attire walking down the hall and chatting with guys and he had stopped for a good minute to watch her ass sway back and forth. A knock on the door snapped him out of attention, it was Jessica.

'Stand.'

Brian stood immediately, wanting to please and impress her with his obedience. He noted that the outside of his office still had a lot of activity.

'Oh, have you been thinking about me?' Jessica looked at his tent up trousers.

'I... ummm'

Jessica just laughed and took out her phone 'This is precious, I have to share this' walking towards him.

Brian started to panic and protest 'Wait... who are'

Jessica placed her finger over his lips and Brian snapped shut. He tingled at her slightest touch and inhaled deeply to take in her sweet perfume as she stood close.

She tip-toed and whispered into his ear noting his shiver 'Are you going to trust me?' glancing at the tiny wet spot at his trousers and watching him nod dumbly at her words.

Way too easy.

'Kneel' giggling as she watched Brian fall to his knees.

Jessica turned and walked to the door, adding an extra sway now that his face was at her ass level. She locked the door and walked back over, bending over to expose a ton of cleavage. 'I hope you are not too busy, I have something to tell you.' she giggled. She strode over to the couch and sat down crossing her legs sexily. 'All fours, thank me for coming by.' she smiled.

Brian fumbled and crawled over, thanking her profusely for giving him attention. He pecked at her shoes.

Jessica used her foot and pushed Brian back to his knees before placing a heel in his crotch 'My my, aren't you excited' she sang. 'Off with it.' as she watched him pulling his pants to his knees.

'So, as you know, I have been a little preoccupied lately' Jessica raised her shoe to lightly brush his cock drawing a gasp. 'I mean sooo many men have been messaging me constantly and I think I have finally found a new boyfriend,'' she laughed as she saw his eyes go wide and panicked. She let the silence float in the room, enjoying the tension she created. She reached out and cupped his chin 'Oh sweetie, don't worry, I am not replacing you. I am just letting you know that I am going to add one more to my little play den for... I guess you could say, sexual purposes. A girl like me can never have too many.' Her finger gently stroked his chin. She knew what her intimate touch and her words could do to him and was eager to take him to the next level of submission. Jessica watched as his eyes went from desperation, to relief, to a little disbelief before resigning to his fate. Her own eyes sparkled as she watched him accept his place as he dumbly nodded.

'Good' Jessica said simply.

'Now, I have a hot date tonight' Jessica leaned back and lightly used her heel to stroke the length of his prick. 'Why don't you polish my shoes for me?'

Brian's body moved on his own accord as he grasped her foot and began lapping at her shoes as Jessica played with her phone. He sneaked several peeks up her legs and saw flashes of her tiny pink panties and could see the bottom of her perky round ass cheeks. He was jealous of her date but at the same time knew that he could never stop Jessica from doing what she wanted. How could he? He was just thankful that he was still a part of her life.

Her voice brought him out of his trance. 'Oh, has it been 30 minutes?' Jessica yawned before standing up, putting her phone away. 'Good job doggie! It's so shiny now' she patted his head as he beamed with pride.

'Now I suppose you should get a little reward for your obedience. Hmmm. Oh, before that, do you have a little cash you could give me for the weekend?' Jessica said in a girl teasing voice.

Brian looked up at her blankly, a sweaty mess on the floor with his pants down. He took out his wallet and was unsure of how much to give to her, so he just handed it to her.

Jessica took out all his bills without looking and handed it back. 'Purrfect, well I guess I know the reward you are after even if you don't know it yourself. I really am so attentive to you' she giggled at her own joke. 'I saw you checking out my ass today, you weren't very subtle. People may talk if you're not careful.'

Jessica positioned herself with her ass inches from his face 'You love it don't you?' she teased. 'Well I mean, you love every inch of me. You do anything just to kiss it. Here is your chance. You can stoke yourself while kissing it for just a few minutes, a reward for being a good boy today.'

Jessica pulled up her short skirt revealing a curvy pert ass that was the most inviting object he has ever seen. He pushed his face into an ass cheek with a kiss, then started to kiss her ass greedily, not wanting to miss an inch. He kissed the curves on the bottom, kissed her ass crack up and down as Jessica pushed her ass back gently into him. He used 2 fingers to stroke himself as he knew that he would not last long, alas he was right. Brian could not hold back anymore and kissed deep into Jessica's ass crack, burying his face into it as he spurted into the ground, less than a minute.

Jessica Mercedes pulled her skirt back down and before he knew it, kissed him on the cheek and gave him a light slap before she turned around and strode out his office leaving him where he was, dazed, half-naked, in the middle of his office thinking of how lucky he was.