Debbie Does You #7 - The Learning Curve

I have gotten so much inspiration from my pals at Viva Ponta, this is one more.
Enjoy BL.















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.

You Are Mine! - Part One

To read about the last job I did for my boss check out A Team Player At Work


The fantasy weekend wore me out, but it was fun. This was still the best job I ever had. Once I got back to my cottage I ran a very warm bath along with sea salts, took my clothes off, letting them fall to the floor, and got in to soak. My overused nipples and pussy felt so much better as the water washed up against my skin. I stayed in the tub until the water began to cool off and finally got out and into my silk pajamas. I crawled into bed alone for the first time in days and fell asleep in minutes.

Feeling so refreshed when I woke up, it was as though I was a new woman. As I walked from my bedroom to the kitchen I noticed something that reminded me that requests from my boss are made even as I sleep. There was an envelope that had been shoved under my door. The stationery was familiar and I tingled a bit thinking about what may be written there.

What I saw was a new way my boss wanted to play. I was his sex maid and I had to do the job I was instructed to do. That was never more true than with Michael’s latest note:

Debbie:
I’m giving you your clothing allowance a little early this month. I have already picked out the clothes I want you wearing tomorrow night. Everything is ready for you to try on and pick up at Lee’s Dress Shop. Be ready at 8:00pm tomorrow night. Keep in mind that you are my maid and you will do as I say. You will stay at the cottage and I will come to you there.
Looking forward to you, Michael.
PS: never forget you are mine.

The tone of the note was a little different than usual, but I followed his instructions and headed to the dress shop. When I got there I introduced myself and was treated with some of the finest customer service I had ever experienced. The clothing was all boxed up. I knew that Michael knew my sizes very well so I decided I would try them on at home. I paid for everything and headed home.
I took all the bags and boxes to my bedroom and immediately began my investigation. I had not yet really dressed up for Michael in any costumes, but it looked as though that was going to change. For the first time I was to dress up as what I was, a sex maid. I relaxed for the rest of the day, until it finally got to be time to get ready for my boss.

After showering, and trimming my pussy just the way Michael liked it, I started to get dressed. I put on his favorite perfume, Victoria Secret’s Rapture and then dove into the new outfit. The first thing I noticed is that there were no panties, so I started with the stockings. They were fishnet and had thick elastic at the top to help keep them up, no garters necessary; the bra was a lacy thin material that would show off my nipples once I was properly aroused. Next I put on the thick vinyl choker, and then I pulled up the tight fitting short plaid skirt and adjusted it. He had chosen one that was so short that I couldn’t bend over without my ass peaking out. The top was a button down white shirt with tails. I tucked it into the skirt, put on a pair of dangling pearl earrings, a touch of make-up and waited.
I was surprised when I looked at the clock, it was 8 o’clock, but Michael wasn’t at my door yet. Usually he was early when I had a date to perform my duties. As I sat on my chair, I began to realize what I was going to be that night. I was to be his. I was going to be reminded of my role here and I knew it. It was then that I heard his footsteps on the slate slabs outside my door. He came up to the porch and entered the cottage without even knocking.

I gasped at first, but within a split second I understood the circumstances and wasn’t really surprised.
“Good to see you ready Debbie”, Michael said. I just smiled and nodded, unsure of what he exactly wanted from me.
Michael told me to stay seated and proceeded to ‘get some things off his chest’.
He said that he needed me to understand some things about my job. Michael told me that we had some great times together so far, and I agreed with him. Then things seemed to take a nasty turn. He told me that I was becoming quite the whore, that the latest party showed my true side. This surprised me and when I tried to explain myself he told me to shut up.
“From now on you remember one thing bitch, you’re mine. That means this is the only cock you get, understand?”, Michael asked quite forcefully.
“Yes sir”, was my only answer and that seemed to please him.

Then it was time to be inspected. Michael wanted to be sure that I did everything right when I got dressed. He told me to stand up and came close to me, running his hands up my stockings and pushing my skirt up. He said I had the stockings, garter, and skirt on right, but that I hadn’t trimmed my bush correctly.
“Get your trimmer for me Deb”, he commanded.
I quickly ran into the bathroom and got my special electric trimmer and brought it out to him. He pushed my skirt up and told me that he wanted to see a bare little girl pussy. He ran the trimmer over what was left of the hair on my snatch and shaved my pussy bald.
Michael let the skirt fall back to its original place and stood up to inspect me above the waist. Again everything seemed correct at first, but he didn’t like that I had buttoned the shirt almost all the way up. He yanked at the buttons and tore the blouse apart, exposing the bra, and pulling the tails from the skirt.
“You like being treated as the slut you are don’t you Deb?”, he asked.
Again my only answer was, “Yes sir”
“You are beginning to understand”, he said as he smiled and pushed me back onto a stool.

Next Time: The Maid Gets Made