Please Let Me Cum, Sir

AUTHORS NOTE - This is the latest story in the series. Feel free to continue to read on but to get to grips with the characters and the story so far, feel free to dip into the previous exploits. Above all...enjoy...

Wednesday

Jack had just finished a gruelling three hours of an intensive interview process. It had gone well, in his opinion. Grant - one of the directors - was finally taking his early retirement and his position needed filling up on the 18th floor and Jack had been the prime candidate for the job.

He sat back in his office chair and took a few moments. He revelled in the silence for a few minutes, taking stock and recapping some of his responses. He thought it had gone quite well but he was never someone who expected something for nothing, he always worked hard for things and he would wait for the response from the directors later.

Jack looked up at the clock, smiled and started to shut down his computer. He stood, pushed his creaking chair under the shabby desk and moved to grab his coat from the back of the unpainted door. He looked round at his small office and thought again at the potential move upstairs. He would find out within the hour at home. It had been tough today and he deserved to just go home and relax now.

He hadn't heard anything by the time he pulled onto his driveway. He cut the engine and stepped out of the car. Jack trudged towards his front door, unlocked the catch and opened the door. He looked backwards and saw that Anna was pulling into the driveway behind him.

She parked the car and jumped out of the driver's seat. "Well?" She enquired bubbly.

"They said they'd call before 6pm tonight," he replied.

She was wearing her tight, black pencil skirt which was cut just above her knees. Her legs were covered with a pair of sheen-finish black nylons with her high black heels. Jack's eyes explored upwards and saw that Anna was wearing a red, tightly fitted thin v-neck jumper. It hugged her curves and Jack could clearly see the shape of her pert breasts. Her tanned chest and collar bone clearly on show just below her pretty neck. Anna's hair was in a tight bun balled up on the top of her head. It showed off her beautiful face: her full lips, toned, soft skin and her big brown eyes.

"How do you think it went?" Anna asked, whilst making her way up the drive towards him.

"I thought it was good. We'll see soon," Jack replied.

She kissed him on the lips and smiled, "well, let's hope so."

Suddenly, Jack's phone started to ring in his pocket. He looked up at Anna and she quietly squealed.

Jack lifted it and saw it was the call he was waiting for. He exhaled and answered. Anna looked at him and waited, he could see that she was trying to hide the smile on her face.

"Jack," the voice at the end of the line said, "Wilson here. The directors and I were really pleased with your efforts today. We knew you'd impress us and we are rarely wrong."

Jack smiled. Anna let out another quiet squeal and clapped. She then hurriedly let herself into the house and closed the door behind her.

"Grant was making too many mistakes Jack," the voice continued, "and we don't like mistakes. We've always known you were meticulous and your track record is proof of that. Therefore, Jack, we would like you to join the directors and move up to the 18th floor."

Jack could barely hold in his excitement.

"Wow. Thank you Mr Wilson. That's...fantastic news sir. You won't be disappointed."

"I know, Jack. You start on Monday. So get in over the weekend and move your things up to Grant's office. Welcome aboard Jack. Don't celebrate too hard, you've got a busy week in front of you." With that, Wilson ended the the call.

Jack listened to the automated woman's voice on the end of the phone explaining that 'the other person has cleared' and he smiled. He looked down at his phone and closed the screen.

He had done it. Hard work and perseverance had paid off and he was moving up. He moved into the house and Anna stood in front of him. She threw her arms around him and kissed him deeply.

"Congratulations. I knew you would do it. Welcome to the 18th floor. All the best people are on the 18th floor!" Anna joked.

"Yes," Jack grinned, "we'll be working together now. You're now going to be my PA."

She stopped smiling and lowered her face whilst looking up at him with her big doleful eyes. "Yes, Mr Fraser. I'll be good, I promise."

Jack's cock instantly stirred from the playful way she said it and the way she looked at him.

"I'll do everything you tell me Mr Fraser," she continued, cheekily teasing him.

Jack laughed and wondered exactly how serious Anna was being. He thought he'd join in and see, "get inside Anna."

"Yes sir," she replied. Anna turned and walked inside through to the lounge. She stood in the middle of the room looking at him. "Anything else...sir?"

Jack looked at her. She was serious. He started to wonder how far she would go. "Turn around and bend over for me."

Anna smiled. She slowly turned and bent far over. Jack could see the outline of some very thin panties through the thin skirt material. The slit in her pencil skirt rode up and Jack could see her long legs covered in her sheen tights. His cock started to grow.

"Like this, sir," Anna enquired, "is this right?"

Jack nodded. He moved up behind her and stroked her sexy arse over her skirt. She moved her arse a little from his touch. His cock was fully erect now and he moved up close to her arse. Jack started to grind his groin into her arse. She moved her hips in time with his thrusts.

"Am I doing well sir?" Anna teasingly asked.

Jack grunted his confirmation. He thrust forward again and felt the satisfaction in his cock. He thrust forward again and it pushed Anna forwards too.

He moved backwards and she looked back at him over her shoulder. "Now turn around and remove your jumper and skirt," he instructed.

Anna seductively turned around and looked directly into Jack's eyes. She placed her hands at the base of her jumper, "yes, sir," she muttered. Anna then lifted the jumper up over her waist and her head.

Jack stared at her sexy body. She had a tanned, toned stomach from hours of hard work in the gym. Her bra was black and it supported her breasts by pushing them up in the cups. He could see the top half of her breasts forced upwards by the bra and they started to create a channel of cleavage.

Anna continued to undress and moved her hands around her back. "Like this, sir?" She teased. She slowly undid the hidden zip at the back of her skirt. And watched Jack's reaction as she eased the material of the skirt over her hips and let it slide down her long, shapely legs. Anna then carefully stepped forwards in her high heels so that she was out of the skirt and left in a neat crumple on the floor.

Jack stared at this beautiful figure in front of him. Anna smiled and looked down at his trousers. His erection was clearly visible through the material and the thrusting against her arse had clearly left him in a very aroused state.

"Turn around and bend over," he commanded.

"Yes, sir," She replied and assumed the same position she had been in a few minutes earlier.

Her black small panties had more material than a thong around the back but less material than a regular pair of panties. The material was a fine mesh see-through material and was in the shape of a triangle that covered a small amount of her sexy arse.

Anna looked back at Jack again from over her shoulder, "am I getting it right, sir?"

Jack nodded and shuffled forward again up to Anna's arse. He stroked over the material and over her soft, pert arse cheeks. Whilst he continued to gently stroke across the material and over her arse, Jack used his other hand to undo his belt and trouser buttons.

Anna smiled when she saw his trousers slide down. Jack then placed both hands on Anna's hips and rested his erect cock (still inside his tight briefs) against the soft, mesh panties that covered her arse. He thrust his cock against her arse again. He felt the skin of his cock pull back and the head of his cock pulsed. He repeated the thrust a second time and then a third. Each time Jack thrust he felt Anna pushing back with her arse to meet each thrust. It was creating a tight, closed gap around his cock and he felt his balls start to tingle. He thrust forward one final time and, reluctantly, Jack stopped.

He stepped back and looked at Anna bent over in front of him again. She looked back at him over her shoulder again. "Sorry sir, have I done something wrong?" she teased.

Jack shook his head, "Turn around. Get on your knees and get my cock out."

Anna quickly turned around and dropped to her knees in front of Jack. Her eyes were level with his aching cock. She looked up from her position, "yes sir, of course."

Jack looked down into her big brown eyes and his cock started to ache at the sight. He could see the tops of her breasts: full and spilling over her bra.

Anna reached her hands up and started to gently ease down Jack's briefs. She moved in closer to lift the back of his briefs over his arse. She eased them down and her mouth almost brushed the tip of his fully erect cock. Jack could feel her hot breath against the head of his cock. Anna exhaled deeply as she saw it.

"Open your mouth wide for me," Jack instructed.

Anna looked up at him and, for a fraction of a second, Jack thought he had gone too far. "Yes sir," she agreed and she opened her mouth.

Jack could see her tongue laying flat on the bottom of her mouth and her big eyes were wide, expecting. He grasped his cock in his hand and slowly stroked his hand down his shaft and then back up. The action caused him to buck his hips a little. It brought the skin over the head of his cock and down his shaft. His balled up fist stopped below the ridge of the cock and then moved back up and over his cock's head.

Anna flashed a glance down at the action and then back up at Jack. He repeated the action. She looked intently into his eyes, "shall I suck it sir? I could place it in my mouth and my tongue could circle the head."

Jack groaned.

"I could suck it really tightly. It would be warm and wet like my tight, wet pussy."

Jack started to feel his orgasm building. He stopped stroking and just gripped his cock.

"Tell me what you want sir." Anna kept her mouth open and stared at Jack's cock. "Tell me..."

"Stick your tongue out," Jack instructed.

Anna instantly completed the request and Jack eased the head of his cock down near to her tongue. The pre-cum on his cock had started to build at the tip. He lowered his cock onto her tongue. It felt warm and wet. He just left it on there and never moved. She deftly curled her tongue to create a soft pad that enveloped the head of his cock.

Jack stroked slowly one more time and groaned out loud. Pre-cum spilled onto her tongue. She never closed her mouth around the head of Jack's cock. She just had her mouth wide open and her tongue half sticking out. Jack stroked back and forth twice more and the head of his cock bulged.

Suddenly he stopped. He felt his orgasm building and had to stop.

"Why did you stop sir?" Anna queried. "Were you going to cum in my mouth? Were you going to milk your cock in my sweet mouth? You could, you know? Just tell me, sir." Her eyes were big and her cheeks were flushed. Jack knew she was aroused.

"Are you wet?" He questioned her.

She bit her lip, looked up at him and nodded in a silent, pleading way.

"Do you want to touch yourself?" Now it was Jack's turn to tease her. "Stand up, show me," he commanded.

Anna stood up and she was very close to his face. She kept her eyes locked into his and she lowered her hand slowly down her slender stomach and down into her panties. Jack could feel the material of her panties on the tip of his cock as she pushed her hand down towards her pussy.

Anna slid a finger into her pussy, "hmmmm," she groaned. She then brought her finger up between their mouths. Jack looked down at her wet finger. Anna eased her tongue out of her mouth and licked the top of her finger clean of all her juices.

"See, sir. I'm so wet. I need to touch it. Pleeeease let me touch my pussy," Anna begged.

Jack smiled and shook his head, "sit on the table and part your legs," he instructed.

Anna almost ignored him and started stroking her pussy. She looked at Jack and then followed his instruction to the word.

Jack looked at her on the edge of the table with her legs splayed wide. Her panties were wet, he could see the moist outline on the black material.

"Like this, sir," she queried. She knew he was looking down at her wet crotch. "See how wet I am sir, please help me."

Jack moved over towards the table and removed his shirt and tie whilst on the way. His erect cock bobbed in front of him. He stood in between Anna's wide legs and his cock pushed against her pussy. The soft material of her panties was blocking the entrance but it felt really good on the tip of his cock.

"Hmmm, sir," Anna softly groaned, "I can feel your hard cock. It's so close to my pussy."

Jack held onto Anna's hips and thrust his cock up and forwards. The material on her panties gripped the skin of his cock softly and pulled the skin back. His thrust upwards had pushed his cock against Anna's clit.

"Ohhh," she moaned, "that feels good sir. Please do it again."

Jack slid back and then thrust forward again. She moaned again, louder this time. He slowed his thrust and then started to grind his cock against her panty covered pussy over and over again. He could feel the material against the tip of his cock and it was intense. Jack could feel her panties were damp from both Jack's pre-cum and Anna's wet pussy juices.

"Ohhhh...sssir, it's rubbing against my clit. Ffffffuuck it feels good," Anna moaned.

"Do you want to cum Anna?" Jack whispered. Their faces were very close together and they were looking into each other's eyes.

She bit her lip, "sir, please let me cum. Shhiiiit, I'm close...please don't stop...I'm going to cum."

But Jack did stop.

He found it incredibly difficult to pull away because he was close to orgasm too. But he pulled away from Anna and left her moving her hips in search of that final thrust.

"Ohhhhh...hmmmmnnn. Fuck, I'm so close," she groaned.

Jack grabbed each side of her panties and roughly pulled them down her legs. He tossed them down on the floor and used his hand to spread Anna's legs again. He looked down at her wet pussy. The moisture had built up and the outside of her pussy lips were glistening.

Anna watched Jack looking at her pussy. "I'm...I'm sorry sir," she mustered, "I'm so w-wet."

Jack moved back to his position in between her legs. There were no panties or material to stop him this time. He placed his cock length ways against her slit. The head of his cock rested just above her clit. The rest of his shaft was nestled against her wet lips.

He looked at her, directly into her eyes. She stared back at him and seemed to nod.

Jack thrust slowly again. The feeling was better with the wetness. He was easily able to slide his shaft backwards and forwards with the natural lubricant.

"Ohhhh ffffuck," Anna groaned.

He thrust again and watched as his cock ran up between the outside of her pussy lips and nudged over her clit. Her wet lips wrapped themselves around his shaft. The image made his cock pulse. He felt his balls tighten again.

"Please sir, ppllleeeaase..." Anna was grinding against his cock now. She started to shake.

Jack stopped again. He knew she was close. He was too.

"Jack...sorry, sir...please. I'm so c-close."

Jack took his hard shaft in his hands and lowered the head of his cock to the entrance of her pussy lips.

Her eyes widened when she felt the tip against her entrance.

"I want to see you use your hand on your clit. I want you to use it very slowly. No cumming unless I say so, is that clear?" Jack stated.

"Yes sir."

She lowered her hand to her pussy and it went straight to her clit. She started circling it, using two fingers. Her hips instantly started moving to match the attention from her fingers. "Ffffuck...oh god," she groaned.

Jack kept the tip of his cock nestled between her pussy lips, teasingly near the entrance. He, too, started stroking his shaft very slowly.

Anna could feel the slow movement of his cock against her pussy and it was adding to the sensation for her. She looked at him and whined. Her body was starting to shake. "Sir...p-p-p-pleeeease can I cum. Oh god...oh god...I'm so close. Fucking hell."

"Pardon?" Jack responded. He wanted her so close to the edge and was willing to make her wait longer. He was really close too though and was slowing down his strokes, wondering if he would last.

"Ohhhhh...I need to cum so badly. Oh...oh...oh...ffffuck. Can I cum? Please? I've been such a good girl."

That last statement caused Jack's cock to bulge. He groaned when she said it and Anna knew the reaction it has caused in him. She smiled through her moans. She had slowed her stroking to almost a stop. Both of them were extremely close. Her legs were really shaking: she had been close to cumming a few times tonight and the need to orgasm had grown in her.

"Hmmmmn...Jack," she looked serious at that moment and deep into his eyes, "please, please let me cum."

Jack stroked back along his cock again and gently thrust forward. His cock pushed against her opening.

"Fffffuuuck...Jack, pleeease," she moaned.

Jack stroked his cock back one more time and looked at Anna. "Cum for me," he demanded.

Anna instantly sped up her strokes and her moaning started to grow louder.

Jack pushed his cock into her pussy. He felt the tight opening grip the head of his cock and pull the skin back over the head of his cock. He continued deeper and thrust into her. His hips ground against her pussy and Jack felt the head of his cock up against the roof of her pussy. The head of his cock felt huge deep inside her tight pussy. She moved her hips to meet his thrust: her hands furiously stroking over her clit.

He slid his cock back out and he felt his orgasm. As he pulled his cock clear he felt the cum spurting out of his cock. He was cumming without touching his cock. The cum stream spurted out over Anna's pussy and over her fingers.

"I'M CUMMING! OH, FUCK, FUCK, FUCK...NNNNNGGGGGG!" Anna screamed as Jack's cum hit her body.

Jack felt another stream of cum leave his cock and dribble onto her pussy lips. He then grabbed his cock and eased a slow deep stroke down his slippery cock.

"Fffffuuucking hell Jack. Oh my god," Anna groaned. "Did you just cum without stroking?"

He nodded.

"That's so fucking sexy," she moaned. "It felt good with that cock of yours in my pussy. It shocked me..in a REALLY good way. I just never expected it. Fuck, I'm so wet."

She was still circling her pussy and his cum had dribbled over her pussy lips.

"Now," he said, "to plan for my new move."

Anna's eyes glinted as she thought of all the naughty things she wanted to do with him in his new office. "Yes," she whispered whilst looking directly at him, "yes...sir" she giggled.