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How An Instructor Becomes A Pupil

"What started as a training course became a lesson for the instructor"

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Claire was a head-turner, mainly due to the size of her breasts. At 36DD, she was hard to miss. She was ample up top and had a trim, almost hourglass figure that she was not afraid to use to her advantage, and she was also well educated. She had an Honors Degree in Business and made sure that she had progressed through her jobs using her talent and not using her assets.

Claire had started a new job with a new team. They used a software package to which she had little exposure. So she was scheduled to attend a training course. During a break with her team members, they told her that the instructor was very introverted and would be sure to blush whenever he looked at Claire.

Claire decided that she could have a little fun when she was away. Even though she was married, her sex life had home had tailed off, and the excitement and spontaneity had gone from her marriage. She still loved her husband, but she was missing that vital spark.

She packed her clothes for the week, making sure she had her favourite underwear to put on. She knew there would be other people on the course, but she had already decided on Toby, the instructor. She arrived at the hotel late on Sunday evening, and the weather started to turn for the worse. The skies filled with dark, ominous clouds. It was going to be bad weather.

On the first day, Claire had already decided to wear her flat shoes, trousers, and a dark blue blouse, covered by a jacket. She had the top two buttons of her blouse undone, so her cleavage was visible but not overly so. On arrival, she was met by Toby, and he showed her to an office she would use while on the month-long course. She looked at Toby. He was six feet two inches tall, with a well-toned body, which she was sure was natural rather than time spent in a gym. He had brushed-back mousey blond hair and a well-trimmed beard. Glasses almost hid his blue eyes. Even with his looks, he seemed uncomfortable in approaching women.

As she bent down to put her computer case and handbag on the floor, she caught Toby checking out her rear, then she stood up and saw his eyes focus on her breasts. At that moment, she remembered what the other girls had told her and knew she could break this man and get him to do what she wanted.

The course began with the health and safety brief and introductions. There were another four people on the course. Two women and two men. They all worked in a similar field to Claire and were all about her age. The course settled down to Toby, showing them the functions of the software and giving them an overview before they broke for coffee. As they chatted, Claire caught Toby glancing at her breasts, and she knew then that she would have to bring him out of his shell.

It started to rain during the lunch break. The rain seemed to be coming down in heavy sheets. It was torrential. The course continued in the warmth of the classroom. They started to do a practical part of the course. They were given a link to download some files to practice the basics. Claire had already used this part of the software, so she loaded it up and saw that Toby was walking around, ensuring everyone had followed the instructions and was starting the practical.

Toby got to Claire's desk. She leaned back in her chair, making her chest pop out, and with Toby leaning over her shoulder, she looked up. Toby's eyes fixed on her cleavage, her blouse open enough for him to see her dusky blue bra under her blouse. She looked into his eyes and whispered, "You can look at them whenever you want."

Toby quickly averted his gaze and checked her screen. "Looks like you know what you are doing," he said before returning to his desk. Instead of standing up, Toby sat behind his desk and used a pointer to show the class various tasks that could be done from the screen they were on. Claire was sure that he was seated so he could hide his erection. They continued to use the software and try new functions until they broke for afternoon coffee.

After the break, they all went to their separate offices. Claire had a chance to catch up with her office emails and check for new projects. She also got a chance to check her phone. There was a message for Harriet in the office asking how Toby was. She replied that he was still in good condition and added a smiley face.

She left the office and drove back to the hotel. It was still raining, and the roads were challenging to navigate, so she went slowly and carefully. Finally, she got to her room and suddenly realized how tired she was from the training. It had taken it out of her. She lay naked on her bed, her mind focusing on Toby, his body, his eyes, wondering what his hands would feel like on her body.

The next thing she knew was her alarm going off. She woke up with a little bit of a shock. She had been asleep naked, on top of the bed. It felt marvellous to feel like this. She thought about what her husband would think if he slept naked. She showered and dressed, then went to the office. It was still raining, and the river at the side of the road had almost flooded.

The second morning passed quickly. Toby once again showed the class more and more functions and complex operations of the software. Claire had thought this was a simple course and was surprised at the power of the software. This morning she had decided to wear a tighter top. Instead of her blouse, she wore a knitwear top with a v-collar, which plunged into her cleavage, and she wore a skirt that swayed when she walked, highlighting her buttocks.

They broke for lunch, and Claire took her phone out of her purse. It had been on silent while the course was on. She found she had several missed calls. She looked at the number and did not recognize it, but it had a local dialing code. She rang the number and found it was the hotel. They informed her that due to the hotel's location, and the amount of rain, it was highly likely that the road would be closed and that they were very sorry. Claire said that she would make alternative arrangements for the night.

Claire asked the others where they were staying and checked to see if she could get a room. She called the hotel and was informed that it was fully booked. However, after checking for other hotels in the area, they were either fully booked or inaccessible due to the flood. So she asked Toby if he knew anywhere. He told her that he might know a place in the village where he lived, and it would be easier if he gave her a lift.

This was partially the answer she wanted. Now all she needed to do was to get him to take her to his house. By the end of the day, the rain still had not eased off. She walked out to Toby's car. Her top was soaked, clinging to her breasts, the outline of her bra visible. Toby held the car door open for her, and Claire thought he was doing it to ensure he got a good view of her breasts.

The coldness of the rain was making her nipples begin to harden, and they were showing through her top. Toby drove carefully through some large puddles that filled the road. She knew her car would not have made it. Finally, they arrived in a small village. There were the usual places, two pubs, a church, and a small shop. Toby stopped outside the Red Dragon, climbed out of the car, and went inside. He appeared moments later and sat in the driver's seat.

"Looks like there is no room at the inn."

"Well, in that case, it looks like you are stuck with me," Claire responded.

Toby looked shocked, as if unsure how to answer. He began to mutter something, but Claire continued,

"Look at it this way, and I have nowhere to go. My car is still at the office, and I must stay somewhere. I am sure you have a sofa, so let's go to the shop, get a bottle of wine, a microwave meal, and make the most of it."

She had just made Toby take her to his house. Toby drove a hundred yards to the shop. They went in and got food and wine. In the process, Claire made sure her top got another soaking. Not only did her top get wet, but the wind was blowing the hard rain, soaking her skirt. Sitting back in the car, she could feel her wet panties sticking to her. The fact that she would have Toby that night added to the wetness.

They went into the block of flats where Toby lived. He had a one-bedroom apartment. The kitchen area and main room were open-plan; two doors led off the room, one to the bedroom and the other to the bathroom. The lounge had a two-seated sofa, coffee table, and TV stand. Below the TV were the latest gaming platforms and a load of games. The kitchen was fully equipped, but it was a bachelor pad where he seldom entertained women.

Claire was still soaked; she needed to get out of her clothes and get them dry. She asked Toby if he had anything she could wear. He came out of his room with various garments, mainly jogging pants and tops. She quickly looked through them and told Toby to turn around and take them back. She followed him into his bedroom. She looked around his room and decided that he had no women in it; it was a man's room. She opened his wardrobe, selected a long shirt, and told him she needed to change and dry her clothes.

Toby said that he would find something to eat while she was changing. Instead of using his room, Claire went into the bathroom. Claire left the door slightly ajar; she knew where Toby was standing by the countertop in the kitchen, and he would be able to see the mirror. Standing before the mirror, and peeled off her soaked knitwear top. Pulling it over her head, she looked in the mirror and checked to see if Toby was looking.

She smiled to herself when she saw his eyes transfixed on her. She tried to make it look as casual as possible as she turned around and pulled down her skirt, revealing her light blue lacy panties. She slipped her hands inside the waistband and slid them down her legs. Turning around again, she was once again facing the mirror. She put her hands behind her back and undid the clasps of her bra. Letting her bra fall off her shoulders and then onto the floor.

Claire felt the cool air hitting her; her nipples seemed to get even harder. They were already hard from the rain, and her wet bra had not helped. Now the excitement of being watched was adding to the cold air. For a moment, she forgot about Toby. She ran her hands under her body, cupping her breasts and then slightly lifting them, and her fingers touched her nipples. A wave of bliss ran through her body. She suddenly remembered where she was and pulled her hands away.

She took the shirt off the hook, slipped her hands into the sleeves, and then buttoned it up. She picked her clothes off the floor and walked out into the main area of the flat. Toby just stood and looked at Claire; his eyes were torn between looking at her legs and her breasts. Claire broke the silence by asking where the dryer was. Toby quickly moved the side and opened the cupboard door that hid a washer-dryer.

As the meals were ready, he put them on the coffee table and sat down while Claire was putting her clothes in the dryer. Claire accidentally dropped her clothes on the floor. She bent down to pick them up and remove her knitwear top from the pile. She was hoping Toby had a good view of her exposed buttocks, and even possible he might see the wisps of hair from her pussy between her legs.

Claire felt the excitement of exposing herself to Toby. She wanted him to be excited, and she hoped she could bring him out of his shell. She had already seen the bulge in his trousers and knew she would not be disappointed, but she had to get him to believe in himself, give him confidence, and make him want her.

They had their meals and a couple of glasses of wine. Toby sat on the sofa while Claire sat on the chair at an angle. Instead of her plate on her lap, she had it on the table. She had to lean over every time she got a forkful of food. The top of her shirt was open enough for Toby to see her breasts. She would make sure he was leaning forward at the time so he could see. After they had eaten, Claire quickly got the plates before Toby had a chance. He did his best to be a good host, but Claire had other ideas.

Claire put the plates in the sink, and instead of sitting back on the chair, she sat on the sofa with Toby.

"Now, to make this perfect, you could massage my feet."

Toby looked across as Claire lifted her legs and put them on Toby's lap. He had not massaged a woman's feet before. Toby had lost his virginity at University. He had been to a party and met up with a girl. However, he was not the party type. He studied hard and played sports, mainly rugby, and cricket, and although he would go to the bar after a rugby game, he did not drink to excess, unlike many other players.

The party was in his accommodation block and on the same floor. A few people had just passed a set of mid-term exams. He was still waiting for his results, and he was trying to study for some extra credits. The party had got louder and seemed to have moved along the corridor towards his room. He resigned himself to the fact he was not going to either get more studying done or get any sleep, so he might as well see what was happening.

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He was dressed in a rugby shirt and baggy shorts and flip-flops on his feet. He had gone down the corridor to the main communal area. The music got louder, and he found that most of the people there were girls. Toby looked around. Some girls were already quite drunk, they were dancing on the tables, and there was a general noise. He saw at least two pairs of girls kissing and groping each other and another couple of lads kissing girls. Then, suddenly, two girls accosted Toby. He knew them reasonably well.

"Come on, Toby, have some of this." One of the girls handed him a relatively strong vodka and coke. "Come on, drink it up."

Toby drank it, and as he was doing so, one of the girls had her hand on his crotch.

"Jackie, look what I found." She pulled the top of his shorts away, and Jackie looked down to see that the other girl was holding Toby's erect cock.

"Come on, let's have some fun."

Toby was shocked at their behavior, but the feeling of another person's hand on his cock was overriding any other emotion. Between the pair of them, they almost dragged Toby into their room. For some men, this would have been a total fantasy. Two women, drunk with drink and lust, were going to use him for sex. For Toby, it was his worst nightmare.

He tried vainly to protest, but that just seemed to enhance their enthusiasm. They pushed him down onto one of the beds. Jackie was pulling off her clothes as fast as she could. The other girl, Wendy, pulled Toby's shorts down and started to go down on his cock. She put her mouth on his cock, slurping her wet mouth up and down; with one hand, she stroked him, and the other was caressing his balls. It was his first blowjob, and it was obvious that Wendy had done this before. Suddenly he exploded into her mouth. His cum filled her mouth and dribbled out and dripped on his groin. Wendy, now completely naked, was straddled over his face, her pussy grinding on his mouth. He could hardly breathe; he automatically opened his mouth, with his tongue lapping her juices as she leaned down to lick his cum from the base of his cock. Jackie stripped naked and then rubbed his soft cock on her pussy, while she was holding Jackie's firm tits. She could feel Toby begin to harden.

"Look, he is ready."

Wendy almost pushed Jackie away as she straddled Toby and pushed his almost hard cock inside her pussy. When Toby felt her pussy gripping his cock, he stiffened inside her. She started to bounce up and down on him. Jackie was holding his arms down. He was being used. Wendy fucked him until he came for a second time. Wendy climbed off his soft cock. She was on all fours as Jackie fingered Wendy's pussy, and tasted the mixture of the juices. Then, Wendy started to suck his cock. It took a little longer, but again Toby was hard. Finally, it was Jackie's turn. She climbed onto Toby. As she faced him, she grabbed his hand and put them on her tits.

"Squeeze them."

Toby mauled her tits as she rode him. Wendy was watching and playing with herself as Jackie rubbed her clit. Wendy reached down to add to her excitement. She felt Toby once again let out his seed. She kept rubbing her clit until she came, with Toby still inside her. The girls climbed off Toby and went in the shower. As they left, Jackie said, 'Told you he would be a good fuck, but fuck me, I need my bed, so thanks, Toby, see you tomorrow.'

That was Toby's queue to leave. He grabbed his shorts and returned to his room. His mind was all over the place. It was true he was no longer a virgin, but he had not gone to the party, intending to lose it that way. On the contrary, he had wanted it to be unique and private. But instead, he felt abused and violated. It was at that moment he had become almost a sexual recluse.

With his reflection over, he looked down at Claire's feet. There were dainty and well-kept. He put his on them and was surprised to feel how soft they were. Claire guided him along, telling him how to press his thumb into the balls of her feet and rub her toes. Claire laid back against the arm of the sofa and, without thinking, undid another button on her shirt. At first, Toby did not notice his total concentration focused on Claire's feet. Her cleavage is now fully exposed, so much so it should be the underside of her tits. He felt Claire's feet move in his lap. Her heel was rubbing against his swollen cock. There was no hiding his erection. Claire could feel it too. She moved her foot back and forth over the length of his shaft hidden in his trousers.

'You seem to be enjoying this. How about we move from the sofa?'

Claire said it more as a command than a question. Toby knew he was under her spell. He just nodded in agreement. As Claire got to the bedroom, she wondered how to approach him. She could feel his nervous tension, his apprehension, but she wanted him to take her to make her his own. Standing by the bed, Claire could see it had been made with precision; the duvet was carefully placed, the pillows in perfect symmetry. She pulled back the duvet and found the sheet flat and tucked in, and it was just as she expected.

She stood in front of Toby close; she put her hands out and slowly undid the buttons on his shirt. He stood in silence, his eyes fixed on her hands. Claire pushed his shirt off Toby's shoulders and let it fall, then lowered her hands to the waistband of his trousers.

"Has it been a while?"

"Yes, and never like this," Toby replied

Her hands expertly undid his trousers and then unzipped his flies. Then they pushed the waistband of his hips. Toby's trousers fell to his ankles. He stayed stood stock-still. With his pants down, the only thing stopping his cock now was his boxers. Claire looked at the tent between Toby's legs. Her mouth became a little dry, but she could feel a building up of wetness between her thighs.

"Undress me."

Toby seemed to snap out of his trance-like state. He nervously undid the last three remaining buttons of Claire's shirt. Claire shrugged her shoulders; the shirt fell to fall, leaving her naked and fully exposed to Toby. She watched his eyes as they went from her face to her knees, looking over her body intently.

"Toby, I am yours; I want you. I need you. I want you to have your way with me. I want you to fuck me."

Toby stood still, barely moving a muscle.

"Toby, what's wrong?"

"I have never done it like this before. I do not know what to do." He confessed.

"Oh Toby, let me guide you; let me show how to please a woman, in particular this woman. But you have to promise me one thing."

'"What?"

'"That when I have guided you, you take control and make me yours. Can you do that?"

Toby paused. He knew he wanted to. He knew he should be able to, but could he? There was a naked woman in front of him, enjoying his body, wanting him, not like his first encounter. This was completely different. She wanted him to be in charge. She wanted him to be in control.

"Yes, I can." He replied with just a slight air of confidence.

"Good. Now come over to her."

Toby climbed onto the bed. Clare reached over and pulled down his boxers; his cock sprang up to attention. She was happy with what she saw. He was not shaved but had his pubic hair trimmed. His cock had about a three-inch girth; his foreskin pulled back, exposing the purple head and a little drip of precum on the tip.

She pulled Toby's head towards her and then guided it to her breasts. Her nipples were already hard from anticipation, and she drove his mouth to her nipples.

"Suck them and bite them."

Toby was in total compliance. His mouth around each hard nipple in turn. He sucked hard on each nipple and then held each one between his teeth and bit, not too hard but challenging enough for Claire to let out a little moan.

"That's it, now go down and suck my pussy."

Claire pushed his head between her legs. Then, laying on her back, she raised her knees, spreading her legs wide, exposing her wet pussy to Toby. She began to grind her hips as Toby began with tentative licking. He grew more confident as Claire started to moan again; he could feel her pussy getting wetter as his tongue slid up and down between her parted lips.

'"That's it. Lick it more, put your tongue in and fingers."

Toby began to probe Claire's pussy more. He slipped a finger in, followed by a second finger, and then began to slide them in and out while his tongue somehow managed to find her clit. It had popped out like a tiny penis head, and his tongue was flicking around it. Then, suddenly, Claire loudly moaned, her legs quivering in mid-air. Toby could see little ripples over her stomach as Claire's orgasm hit her.

Claire grabbed behind her knees, lifting her buttocks from the bed. She thought, if I am going to do this, I will do it now.

"Lick my ass."

Toby was in a position to do precisely that. First, his tongue rimmed the edge of her asshole, and then he pushed his tongue in and out.

"That's so good. Grab my tits."

Toby reached up to Claire's body, his hands finding her enormous tits. He gripped them hard, now with more and more confidence. Claire knew that she had broken him now. Now she needed to let him unleash himself on her.

She felt another wave building up inside her body. Toby's tongue was going deep into her anus, his hands almost ripping at her tits. It felt so good. Now she wanted more.

"Fuck me. Fuck my holes hard."

Toby changed his position. He was on his knees between Claire's legs. His stiff cock was at the entrance to her drenched pussy. He pushed his hips forward gently. Claire felt her pussy stretch around Toby's thick cock as he penetrated her labia and entered her. She reached down and grabbed Toby's buttocks and pulled them hard towards her. Fuck, she thought, his cock feels so good inside her.

Toby began to rock his hips back and forth as Claire lifted her hips to meet his thrusts. Toby hit her G-spot with almost every thrust.

'Harder.'

It was only a word of encouragement needed. Toby thrust his hips back and forth, at times almost pushing Claire up the bed. His balls were slapping between Claire's ass cheeks as Toby leaned down and started to bite Claire's hard nipples. This time there was hesitation, no gentleness; he bit them hard, tugging them with his teeth, pulling her tits up, and then letting them go. Claire pushed her head back into the bed. Her orgasms were happening so fast and close together that they had built into one continuous bout of pleasure. Suddenly Toby stopped.

"Turn over!" he said.

Claire was now a servant to Toby. She looked down and saw the sheet soaked from her juices. Toby's cock was shining in the light, her juices making it glisten. She wanted to taste it, but Toby had other ideas. Obediently, Claire got on all fours. Her nipples brushed against the sheet; the slight roughness made them tingle. She felt Toby's hands spreading her ass cheeks. She was expecting his cock to slide into her pussy, but instead, she felt the tip pressing against her wet asshole. She began moving forward, but Toby held her cheeks hard and spanked her! She squealed. Toby did not stop; he pushed his hips forward; he felt Claire's anus opening as he made his cock deeper into her ass. She felt his cock deep inside her, his balls slapping against her wet pussy lips. She began arching her back and lifting her head; suddenly, she moaned even louder as Toby ran his fingers through her hair and then pulled her head back, grabbing a handful.

He was riding her like a horse. His deep thrusts made her hips go back and forth, her head pulling up and down. She had an intense orgasm. Her whole body was shaking as she collapsed onto the bed. Toby's cock slipped out of her ass with an audible plopping sound. He lifted her hips as he thrust forward again, but his cock hit hard into her pussy. He had only a few thrusts before he sent his seed deep inside Claire. She felt him pumping inside her. She was barely able to move as he filled her.

Toby, too, had collapsed on the bed. He was lying on his back, his body covered in beads of sweat. Claire looked at him and saw his semi-flaccid cock, covered in her juices and still with beads of cum on the tip. She moved to take it into her mouth, licking his shaft clean, tasting the sweet mixture of her pussy and Toby's cum.

She kissed him deeply. Her sweaty breasts rubbed against his chest. They held each other tight as their mouths tasted each other, and their tongues intertwined. Claire could not believe how good this had been. As they kissed, Claire could feel Toby starting to get hard again, the wet tip of cock pressing against the inside of her thigh.

"I think we need to go in the shower."

Published 
Written by ReligousEagle
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