The Learning Curve

A True Love Of Skirts And Stockings

The summer was ending and once again Rob had to get ready to get back to work. This year would be different, Rob had become the Headmaster of a local prep school and he was looking forward to that atmosphere after 10 long years in the public school system.

All administrators had to report a week before the students. Rob got to the office early, wanting to make it his own and meet and greet his staff. He had a morning meeting and headed back to his office. Within the hour a woman walked in the door declaring that she was his executive assistant.

He seemed to become immediately attracted to her, but he soon got work back on his mind.

“And your name?”

“Oh, sorry, it’s Mary”, she replied

Mary seemed a little young to be experienced at supporting a higher-level boss, but he thought it would work out as long as they got to know each other’s work ethic.

Rob let her know that there was a lot of work to do before the semester started and to get started sooner rather than later. Throughout the day, Mary proved her efficiency in setting up student records, filing, and correspondence with parents. It was a good start. They were able to finish the day’s agenda by 4:30pm. Rob walked her to her car and headed home. Home, ha! He was going to an empty house. His live-in girlfriend of three years had left him at the end of last year’s school session.

The evening ended early for Rob, he headed to his empty bed. As he turned out the light, he realized that he had been thinking of Mary ever since he said good-bye to her that day. The more he thought of her, of her breasts, and her long legs, the harder he got. This raging hard on wasn’t going to go away by itself. His hand grasped his cock and he started jerking off furiously. It was so intense that he actually cried “Mary”! as he came, in fact his cum seemed to burst out of him, and up to his chest. After cleaning up a bit Rob feel asleep easily that night.

When he got to work the next day there were some tasks needing attention, that were new to him, having only been a public school employee. One was to approve the new school year’s uniforms. Mary informed him that two had arrived, one for the boys, and the other for the girls. Of the two of them, Mary was the busiest that day. Rob watched her run around the office, bending over to get files out of bottom drawers, reaching for supplies on high shelves. It started to drive him wild. He even started to wonder if she was doing it on purpose.

“Mr. Johnson you still haven’t approved the uniforms, we need to get that done today”, Mary said from the next room.

“Right, could you bring them out here for me”? Rob noticed it was already after 5:00pm and got back to the pile of papers still on his desk.

“Sure, I’ll be there in a minute”, she cheerfully answered.

What Rob saw next made him feel as though he had moved into a dream state. Mary was at the door. She smiled and asked, “Approved?”

Mary was wearing one of the girl’s school uniforms. She was about 5’4” and weighed all of 115 pounds. She even had white stockings on! The plaid skirt with a black sweater was so sexy. Rob was so stunned he couldn’t think of anything to say at first.

“Mr. Johnson, I think you need to check the supply closet with me”

Rob stood, his cock already semi-hard.

It was obvious to Rob that this woman hadn’t been fucked in a while. They barely spoke. No teases, nothing false. They just knew the other one had to get off. She was leaning against the back wall when he walked into the closet.

“Take the sweater off and your bra too”, Rob demanded.

She complied and he admired her tits. His hands and mouth were on them immediately. The feel of a warm woman’s body, of soft breasts and hard nipples sent tingles straight to his balls. Now is cock was straining against his pants.

“Take both your hands and lift up your skirt”, was his next demand.

She did as he asked and Rob got another surprise, she wasn’t wearing any panties. He was presented with a cute shaved pussy. His ex-girlfriend used to say that no one ever went down on her pussy like he did. He wanted to know if he still had that magic tongue, it had been a while since he exercised it. He dropped to the floor and Mary started to take her skirt off.

“NO! Don’t take the skirt off and don’t take your stockings off either”

“Yes Mr. Johnson”, was all that Mary said.

His fingers gently spread her lips. The scent of her flower was sweet and his tongue began to explore the inner lips, running up and down her slit, making her rosebud clit swell so he could suck on it. Rob ran a hand up and down her smooth and silky stockings. Mary held him to her as she first started to moan, but those moans grew when he darted his tongue and out of her pussy. Rob kept up his feast until Mary howled with pleasure and released the nectar of her cum on his mouth and face.

Now just his tongue on that tight cunt wasn’t enough. His cock was ready for her. Rob turned her towards the shelving and told her to hang on.

Again all she said was, “Yes Mr. Johnson”. Rob thought about how he would enjoy hearing that more often.

He threw her skirt up so it fell onto her back and presented her rounded ass and pussy to him. Mary heard his belt buckle and zipper being undone. Rob let his pants fell to his ankles, bent over Mary, grabbed her tits and slammed his cock into her. She cried out as his thick cock stretched her open.

For Rob it was heaven, her pussy was tight and juicy. It hugged his cock with force and begged for more. He started to pound her hard and deep. Then he noticed something on the shelf next to him, he picked up the small object and as he drove his cock balls deep into her, he smacked her across the ass with a ruler. The response from Mary was a bit unexpected for Rob, it was, “Ohhh yes Mr. Johnson, ohh yes!”

He kept it up, smacked her again, drove balls deep, pulled back, smacked her again, drove balls deep. It didn’t take long until the hot cum built up in him and his balls let it loose deep inside Mary.

Rob turned her around to face him. She was smiling as widely as he was. At the same time they said, “I really needed that”.

Then back to business. Rob told Mary, “Lick my cock clean and I’ll approve those uniforms, just as long as you keep one for yourself”.

“Yes Mr. Johnson”, was all she said.

Tags straight female   straight male   adult female   adult male   teasing   pussy licking   supervisor   boss   employee