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Headmaster's Secretary - Chapter III

"Liz goes back to Mr. Harper's."

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Liz was beginning that Monday quite excited about what might happen next after what she and Mr. Harper had done over the weekend. Luckily, her order for some new lingerie and office clothes had arrived, and she was busy sorting out what to wear today. 

Liz kept to the red lipstick but decided to put her hair up in a more traditional, ‘sexy secretary’ tight bun. Then she put on one of her new green velvet push-up bras and matching panties with built-in suspenders. She decided to team these with flesh stockings with a black seam and black medium-high platform heels. All this really made Liz look good; her arse looked plump and contoured and her breasts perfectly framed. 

Then she rummaged through her bag of shopping and found a dress much alike the dress Mr. Harper loved so much and had spunked on so much. It was dark blue tartan, a few sizes too small. Liz struggled to pull it over her breasts but managed it – just. It was short, and unlike her previous dress, it displayed her stocking tops when she sat. It also showed off her bum fabulously, and when she bent over in front of the mirror she saw her suspender straps and then her breasts in all their glory. The dress also had a small belt, which enhanced the illusion of the size of her bust and rear. 

Happy with what she wore, Liz headed off to work, taking a spare blouse and blue opaque tights, just in case. When Mr Harper looked at her she could see the little men in his head struggling to help him keep his composure. 

“Well, Miss Cummington, you have outdone yourself. Have you brought the extras?”

“Yes sir,” Liz answered, taking the blouse and tights from her bag.

“Good. Would you mind putting them in the fifth drawer down in that filing cabinet? They will be safe there.” 

“Of course sir,” Liz smiled, knowing exactly what he wanted. She turned round and bent over, keeping her legs straight and together. She pulled at the drawer but it was putting up a fight, so she gave it a few more tugs, feeling her breasts jiggle as she did so. 

“Here, allow me to give you a hand,” Mr. Harper said whilst leaning over Liz, supporting himself by putting a hand on her breast and holding the drawer with the other. His cock was pressed up against her rear. He pulled the drawer a few times, clearly not trying very hard, using it as an excuse to fondle Liz’s breasts and rub his cock against her bum. 

He managed to open the drawer and Liz put the blouse and tights inside, still bent over. She then braced herself on it, as she heard Mr. Harper undoing the zip of his trousers and then she felt him slide his cock between her legs. 

He held both her breasts and began to slide his cock back and forth between her legs, pleasuring her clit. She began to become wet. She heard children entering the school and the bustle of the morning beginning as Mr. Harper thrust his cock between her legs. She tried to resist but still let out a little-too-loud gasp. 

Mr. Harper put a hand over her mouth, slowing down his thrusts. “Best get to your desk, my dear,” he said. With that, he took his cock away and put it back in its lair. 

Liz stood up, straightened her dress and closed the cabinet drawer. Then she turned, closed the door and went over to her desk. 

As she made her way to her desk, she saw a man going up to it. He was old, with scruffy hair, and had the air of a history or geography teacher about him. As Liz sat behind her desk she could see him checking her out, and suddenly became aware that her nipples were showing through her blouse. 

“Do you have an appointment with Mr. Harper?” Liz said, locking eyes with the gentleman in an attempt to shift his gaze from her breasts.

“Er, yes. I am Mr. Glassman, here to talk about this term's trip to Duxford,” he answered, correcting his gaze awkwardly.

“Ah, very good. Please wait here and I will check if Mr. Harper is ready to see you,” Liz said, getting up and motioning for the gentleman to sit down as she turned and went back to Mr. Harper’s office. 

Knocking on Mr. Harper’s door, she looked around quickly. She saw the 'history teacher' looking her way and then quickly looking around. She wondered if he would having problems getting up.

“Mr. Glassman is here to talk to you about the Duxford trip; should I send him in?”

“Very good. Thank you, Miss Cummington. Please let Mr.Glassman through.”

Liz closed the door and made her way back to the history teacher. He was looking in the other direction, so she decided to lean in towards him and give him a good view down her cleavage. 

“Mr. Harper is ready to see you now, would you follow me?” Liz said, startling him as he turned his head. He got up and walked close behind Liz. She could sense him looking at her rear.

She returned to her desk. After the meeting, Liz was called into Mr. Harper’s office. 

“Thank you for coming in. Would you mind getting me a new pad? It’s in the cupboard.”

“Certainly sir,” Liz replied. 

As she entered the cupboard, she heard Mr. Harper come up behind her. She knelt to get the pad and heard a zip being drawn. “I never did check your underwear, and after this morning’s little outburst I believe we had better take precautions,” he said. 

He put a tie around Liz’s mouth as a gag. Then he lifted Liz’s dress up around her hips and pulled its neckline down around her breasts so that he could see her bra. Her breasts were pushed up and forced even more firmly together. 

Mr. Harper sat her on the chair she had been fucked on so many times before. He pushed her panties aside and began to eat out her pussy. Liz squirmed and writhed with pleasure, giving muffled gasps as she got close to cumming. He stopped just as Liz was about to orgasm. He put her panties back in place, soaking up her juices. Then he stood up, kissed Liz’s breasts and played with her nipples. Suddenly, he stopped and took off Liz’s gag.

“Yes, I approve of your underwear. When school has finished and everyone has left you will return here, put a blouse on under your dress and tights under your stockings and meet me in the maths room.”

“Yes sir,” Liz replied with a gasp.

Later, when the rest of the staff had left, Liz went back to Mr. Harper’s office as instructed. He had already left, and had put the blouse and tights on his desk alongside a tie. Liz took them and went into the office to change. 

She put on the blouse and tie, but could only manage to pull the dress zip up if she put the neck of it under her breasts. This did look very hot, though, as it made her breasts bulge and this blouse could barely contain them. But there was another problem. Mr. Harper wanted her to wear the tights under her stockings, but the suspenders were part of her panties. She decided to forgo the tights and explain, as in any event it would create an opportunity for Mr. Harper to punish her.

Liz entered the classroom with the tights in her hand. Mr. Harper turned and looked her up and down. “I’m sorry sir…” she began.

But, before she could get any further, Mr. Harper broke in with, “Miss Cummington, you are in violation of uniform rules. One, you do not have a blazer on, and two, you are not wearing your tights. Put on your tights and blazer. Once you are decent, you will be punished.”

Liz walked to Mr. Harper and picked up the blazer he had put next to him. When she put it on, it had no physical effect on her but did draw the eye a little more. She then unclipped both of her stockings, took them off and then took off her panties. They were sodden from the day’s earlier antics. 

She bent over and put the tights on. They camel toed, and began to soak up her wetness. She put her panties and stockings back on and stood quietly in front of Mr. Harper with her hands on her lap.

“You have disobeyed my commands. You have been bad. You will be punished.” Before he had finished speaking Mr. Harper took a big handful of Liz’s arse in one hand and grabbed her head with the other. He kissed her roughly. 

Liz’s dampness began to seep through the tights and into the next layer. As he continued, she leaned into him more and ground against his crotch. She felt his cock stiffen just as she reached down to touch it.

“Come with me, I will punish you elsewhere. Gather your things and meet me at my car.” He gave her a short smack on the bum, leaving her confused and very horny. 

Liz liked dressing up for Mr.

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Harper’s perverted desires, but wasn't too keen on dressing now, as she would be outside the school where other people could see her. But she couldn’t dispute that it was exciting, and was making her very horny.

As she approached the car, Mr. Harper opened the door and came up quickly behind her. He grabbed a breast and thrust his other hand under her dress to start fingering her. Liz braced herself against the car and came all over his fingers. He put his fingers to her mouth and she licked them clean. 

They got in the car and she wondered what else Mr. Harper had in store for her. “I will need to borrow you for this evening. I am entertaining guests and require someone to serve them. I trust that you will be happy to oblige? But not before you have received your full punishment.” He looked Liz up and down. “You really do look wonderful in that.” 

He soon pulled into a lay-by down a forest road. It was a dark autumn night, and there wasn't another soul for miles. He leant over and kissed Liz, one hand holding her face and the other caressing her leg. Her hands searched up and down his legs and then settled on his re-hardening cock, which she began to rub. It was brimming with pre-cum, so she broke from the kiss and leant down to suck his cock. 

As she played with the shaft and nibbled the head, Mr. Harper pressed Liz’s head further down onto it until she took it all in her mouth. She started playing with her breasts as he moved his hand away from her leg and round onto her arse, giving it a hard slap.

“Good girl,” he said, trying to keep his load at bay.

She lifted her head from his cock and kissed him. “Let’s go outside,” she suggested. Mr. Harper seemed to like this idea, and opened the door. They got out and walked round to the bonnet, his exposed cock waggling from side to side. 

Liz began to kneel but Mr. Harper stopped her. He held her for a moment before carefully undoing the buttons of her blouse, moving the fabric aside to bring her breasts into view. Then he removed them from the bra and allowed them to be free. “Beautiful,” he said.

He pulled down her panties and tights, leaving them around her lower thighs. He gently pushed her onto the bonnet and she opened her legs dutifully. 

“Good girl,” he said again. Then he took his cock, holding the foreskin back, and slid it into her. As he pounded her, he held her legs, thrusting faster and faster, both getting ever closer to cumming, but slowing down in sections to kiss or play with her now free tits.

Just as he was about to cum he pulled out and shot onto Liz’s breasts.“You will now finish yourself off,” he commanded. Liz realised this was part of the punishment, and fingered herself in front of him, letting out a stream of cum and a long gasp.

“Make yourself decent. You will leave my cum and yours there as a reminder” Mr. Harper said as Liz rolled her tights and panties back into position. He wiped his cock on her breasts, minding the huge pool of cum that he had just made. When Liz buttoned her blouse, the cum created a transparent patch where the fabric clung to her flesh.

“I am not finished with you yet. Get into the car,” he said. After some time the car pulled into a drive and Mr. Harper got out, indicating that Liz should follow.

It was quite a large house, typical of the countryside. She went through the grand reception room and then ascended a spiral staircase, turned a corner and found herself in a bedroom. On the bed was a maid’s uniform: a little cap, fishnets and a few other garments. 

“You will change into the uniform, you will leave your things on the bed, and I will get something from the kitchen.” With that, Mr. Harper left, closing the door behind him.

Liz looked around, still in her cum-soaked school uniform/office clothes. She walked over to the outfit, and saw it was very small. So either Mr. Harper had misjudged Liz’s size or he had been naughty and planned for it to be small. 

She revelled in taking off her cum-soaked tights and panties, unclipping the stockings, putting the panties back on again and rolling up the fishnets. Then she took the blazer off and set it down on a chair. 

As she bent her arms back to get at the zipper of her dress, the buttons on her blouse gave way and her breasts broke free. “Oh dear, I can bet I’ll be getting some extra punishment for that,” she said. 

She continued slipping off her dress, the rest of the blouse and the tie, laying each item on the bed. Then she looked once more at the maid’s outfit and tried it on. It wasn't one of those sexy maid’s outfits that Liz definitely didn’t have hanging in her closet at home, but a proper maid’s uniform: traditional black with white accents, a zip going up the front from the mid-section and a small apron.

Liz pulled the zip up as far as it would go. She was left with a visible cleavage comparable and the dress was so short that the tops of her stockings showed. When she bent over, the dress rode all the way up, revealing her panties and suspenders, and the zip would give a little each time. 

She then noticed a garter which finished off the outfit. She stepped back into her heels and almost instantly, Mr. Harper returned. He was carrying a jug of something in one hand and a bag in the other. 

He set them both down on the table and walked over to Liz. “Ah, excellent; is it a good fit? Would you mind doing a little twirl? Move around a little, raise your arms and bend over like you did when you showed me your new uniforms,” Mr. Harper said, smiling.

Liz turned round slowly with her hands on her lap, and then again with them raised. Then she walked away from Mr. Harper, turned round and bent over. He could see down the dress quite well. 

As she bent over, the zip gave a bit, so when she stood up straight again a little more cleavage and a little more bra were on show. She stopped in front of him, turned round and bent over once more. As before, the dress rode up and Mr. Harper had a full view of her panties, stockings and suspenders.

“Everything is looking good, you just need to add a few things,” said Mr. Harper, pushing Liz back down as she started to straighten up. He took a handful of breast and unzipped his cock for another bout of clit teasing. He held each breast, playing with them, making the nipples erect until they showed beneath her bra and dress. He pounded her for a long time, rubbing his cock on the outside of her pussy, making it ever wetter and making her want to feel it inside her even more.

“Turn around, get on your knees and finish me off,” he said, catching his breath. Liz turned around and dropped to her knees. The zip had given a lot more after Mr. Harper’s foray into her breasts and nearly all of her bust was now on display. 

She took hold of the shaft in one hand and cupped his balls with the other. Slowly stroking him, she felt his cock twitch, and even before she had the opportunity to open her mouth, he came. It wasn’t quite as much as earlier; he clearly needed to recharge a little longer, but it was still a good amount. 

The cumshot didn’t have quite enough power to reach her face, but it landed on the collar of her dress. The second volley struck her left breast. Liz took his sticky cock and licked off the last of the cum. Mr. Harper then drew back and walked over to the table and picked up the bag.

“Would you please go over to the foot of the bed and bend over,” Mr. Harper said, his cock beginning to soften. Liz got up and walked over to the bed, but before she bent over she made sure to zip up the front of her dress in case it became fully undone.

“Open your legs, please,” he ordered.

As she did, she felt the familiar sensation of a vibrator being placed in her pussy. Next, she felt something she was not expecting: something cold, covered in lube, was being placed in her arse.“Fuck,” Liz let out instinctively.

“Don’t swear, Miss Cummington. You don’t want to increase your punishment into tomorrow,” Mr. Harper said, giving Liz a sharp spank. “I am entertaining this evening and you will be the service. The food has been prepared. All you do is bring the dishes out in order, serve the guests drinks and manage their requests,” Mr Harper said, motioning Liz to stand.

She followed Mr. Harper downstairs and was shown the food, the dining area, the reception room and the hall where she was to stand and receive the guests.

After half an hour or so of being shown around the house, told which meals to bring out, and where Mr. Harper kept all his booze, Liz heard the doorbell ring. She trotted off to answer it, breasts almost breaking free as she approached the door. 
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Written by MissCummington
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