Chloe's Teacher

As if to reinforce the point, he moved the hand he had been using to squeeze the lube under her, and started to play around her clit again, in the same way as before: teasing it, not touching it. She moaned around the plug. With the skill and ease that comes with age and experience, Andy teased her clit until she was shaking, her breathing becoming incredibly short again. Then he held her there.

"Don't you dare cum," he said, the teasing holding her on a plateau, probably one good push on her clit away from an orgasm she could not control.

With the fingers that were massaging the lube he pushed a finger up, to the second knuckle; she was really tight. He wondered if he had selected a butt plug that was too big, but he only had one smaller. He moved the lube about, as she flinched against his finger. The discomfort in her arse appeared to help her stave off the orgasm that she was so desperate to have.

Andy mounted some pressure with a second finger, and was surprised that it slipped in next to the first without too much difficulty. However, Chloe cried out, "Jesus no." Andy worked the fingers together, stretching out her hole just a little more. Although her attention was definitely back somewhere else, she was clearly fighting not to cum, which pleased him; she was taking the instruction seriously.

With a deliberate suddenness, Andy removed all of his hands from her, leaving her there teetering on the edge of an orgasm, and watched as she slowly controlled her breathing and calmed herself.

"Well done," Andy said. "Bet that was not easy."

"No," she replied, a slight sound of churlishness to her voice. He slapped her arse hard, the ring of the clap of his hand on her cheek bouncing around the kitchen as she screeched in pain.

It was four or five breaths before she was able to speak, but then she said, "Sorry, master," her voice meek.

Andy picked up the plug from where it had dropped on the table as she screamed, and checked his watch; she had been here about an hour and 20 minutes. He could use another 40 minutes before she needed to go home. He lubricated the plug, and brought it down, one hand pulling open her crack to show the very-well-lubricated hole, the other bringing the very-well-lubricated plug to it.

"Relax and this will be easier, and less painful, but make no mistake Chloe, it is going in one way or another, so don't resist," his voice was back to very commanding.

"Yes, master; I will do my best," she replied.

There was a very pronounced flinch when the metal first touched her hole. Andy put pressure on immediately, and about 1.5 centimetres slipped up easily. Chloe was clearly trying to relax, and failing. He twisted the plug until it turned easily, and then, letting go with the hand holding her arse cheeks apart, moved that hand to her clit. She flinched again, but the desire to cum overrode anything else and she pushed into his hand. The fact he was not going to let her cum seemed to have escaped her thinking.

As she pushed into his hand, the length of the plug in her doubled, and she did not seem to notice. It was a third in—her arse was really tight. He leaned over to her ear and whispered into it, "You have only taken 1/3 of the plug. My cock is eight inches long and you will not be able to touch your fingers to your thumb when you hold it in your hand. How are you going to take that?"

Chloe visibly flushed at the description of his cock, but she did not try to say anything. She was building towards the orgasm that would be again denied. He pushed the plug, and she was clearly relaxed, because quite a bit slipped in, but the last part would be the hardest.

"Good Girl," he said. "You are getting there, but the next bit will hurt, and you need to relax, because I am going to force it." He wasn't going to force it, he didn't really want to put her off on the first visit, but he wanted to see her reaction.

He was to surprise to see her take a grip of the table, and then say, "Go for it."

He pushed hard, and she screeched in discomfort but it did move, and as he reduced the pressure not wanting to hurt, she said, "Don't stop, push. I can take it, master."

He pushed again hard, and there was a distinctive pop sound as it went in, her tight little sphincter closing around the thin part above the base. She was breathing heavily and for the first time he saw sweat on her back.

"Thank you, master," Chloe said, she was breathless, and there was strain in her voice, but she seemed to mean it.

Andy let her go, her orgasm that was building so well fading for the umpteenth time today. "Stand up," he said.

She did as instructed, and paused. "Oh my god, that feels so weird, and uncomfortable," she said. Then she moved her body about a little. "I can't walk home like this. Sorry, master."

"You can, and you will." There was no indication he was prepared to debate in his voice, and he knew it, "You can practice in here for 30 minutes, then you have to go."

She took a couple of steps, then he watched as she tried to relax. "Take your skirt and knickers off," he said, as he walked over and took a seat to watch. "I will take your knickers now, but you will obviously have to put the skirt back on."

Chloe complied, slipping both down and stepping out. She picked up the skirt and folded it over a chair back, then she picked up her knickers, and walked over to hand them to Andy. Her walk had a look of discomfort to it, but Andy was admiring her beautiful curvy legs. they were not athletic, but they were not fat either; they looked really good. When she approached him for the first time, he got a good look at her pussy. It was completely bald, soft looking, her perfect little lips coming together softly, with delicate folds at the tops of her legs. Her pink arse he had seen, and it looked lovely as it moved when she walked.

"Keep walking about until it feels natural," Andy said, feeling his erection growing by the moment.

"Yes, master," Chloe replied, smiling at him, her eyes on his dick, hidden in his jeans.

He watched as she walked away. The plug was all but concealed by her buxom cheeks; it really was the best thing he had watched in years. Although her top half was covered by her blouse and a bra, he could get a pretty good idea of what she looked like. She would be shapely, not slim, but he loved curves. Her tits were big, and he spent a minute thinking about resting his head in them.

After about 5 minutes of walking about, she seemed very natural like the butt plug had been forgotten. "You okay?" he asked. "Your walking is normal again."

"I am. Thank you, master," she replied. She came over and sat on the table in front on him, displaying her pussy to him, a cute smile on her face.

"How will you know if I cum when I am not with you?" she enquired. Her voice made this seem like a genuine question, not an attempt see if she could get around the rules.

"I can't," Andy said. "It is about your desire to relinquish control to me, and it is about trust. However, if you follow the rules, when you do get to cum, you will appreciate waiting more than you can know."

"OK," she said simply, and moved her foot, to massage the bulge in his jeans. She tried moving her foot very gently, to imitate the subtle way he had excited her earlier, but obviously she failed due to lack of experience, and because a foot can't be that subtle. "Want me to take care of that?" she asked, voice all coy.

"Actually, no. You can play if you want—although you should ask permission first, in the future—but you can't touch it or see it yet, through the clothes only. You have to dream what it is like." He smiled as he said it, knowing the wait would be as frustrating as not cumming. He wanted her as frustrated as she had ever been when he decided what her next lesson would be.

She rubbed with her foot for a minute or two more, but when it was clear he would not give in, she stopped and got up. She turned around and bent over. "Does it look okay?" she enquired.

Andy could not have asked for a better view. Her round bottom was inches in front of his face, the pink of her spanking delighting him, making his cock strain. He wanted that arse. He moved his hand and stroked her. She moaned gently at the touch, as he enjoyed the soft, young skin under his hand, stroking up her legs onto her arse and back, then up the inner thigh, grazing her pussy lips, to her obvious twitch. He then waited a moment then tapped the plug. She yelped, and spun to look at him, a look of evil on her beautiful face that looked completely out of place.

"I think it is time for you to put your skirt on and walk home, my little pupil," Andy said.

"Yes, master," Chloe said with a lot of deference in her voice. She walked over and picked up her skirt, and then stepped into it, and pulled it up.

Chloe walked back to him and put her arms around him before he could do anything, her head placed just under his chin. She held that position for a moment, then moved, looking up, and kissed the bottom of his chin. He moved his head, brought his lips to hers, and delicately kissed her, pulling her in. He could feel her excitement.

After a minute of kissing her, he let her go and they walked to the door. "You know what you need to do?" Andy asked.

"Yes. Home, butt plug out and cleaned when I am alone, then photo of sex toys. You will tell me which one. Then I will photo both that and the plug inside me for you. You will tell me when my next lesson is. Oh, and I am not allowed to cum, is that it?" Chloe's words flooded out in a stream.

"Yes," Andy replied as he handed her the lube. She dropped it into a pocket. "Give me your phone so I can put in my number." She did so; he typed in his number, gave it back to her, then opened the door. She danced through, and he watched her walk with a spring in her step up the drive.

As he looked out onto the road, he saw Matt, her dad, walking towards her. He said, "I was worried, and coming to look for you."

"Don't worry, daddy, I was safe. And I am super happy! Andy has agreed to tutor me and mentor me in some of the things I need to study. He is wonderful." Chloe shouted as she turned and blew a kiss. Andy laughed, and put his hand up to Matt in greeting.

"Cool. Cheers, Andy," he said loud enough to be clear.

"No worries. I think it will be fun," Andy replied. "Until Friday, Chloe," he continued with a wave, and walked back in, closing the door behind him. Oh fuck, what had he just started?