The pain was unpleasant as Chloe sat on the toilet extracting the Butt Plug; she had her other hand over her mouth in case she made too much noise. There was a pop as it came out, and she relaxed, feeling her heart rate slow, and breathing returning to normal. She could not believe she was here. Less than three weeks ago, she had made the decision to progress down this path. Two weeks of trying to get his attention and...nothing. Then two things happened in one day to start the ball rolling, and two days later, today, success.
Chloe had first been introduced to the idea of control games, subs and doms when she had spent lazy sunny afternoons in the school holidays in Andy's garden with Max, his son. She had never done anything with Max, but when they were exploring one afternoon they had found a stack of magazines in Andy's study. Max seemed quite uninterested in anything other than the pictures of naked women, but Chloe had loved the stories, and the images of red, spanked bottoms. She had read stories every afternoon that she and Max were alone. She had nearly been caught so many times, but it was the only place she knew to get her fix of reading about women tied up and spanked. There was much more to them than that, and she was a little older before she really got the idea of power games, and then a little older still when she realised that she was really turned on by the idea of a man having total control of her.
She had her first proper boyfriend at seventeen, but he was more scared of spanking her than she was of taking the spanking, and the idea of dominance was completely beyond him. Then just after she had turned eighteen, she met her second boyfriend. He was happy to slap her arse, and tie her up, but he really had no clue what to do with it. She had got more out of two hours with Andy than from the three months of trying to teach her ex-boyfriend.
So, three weeks ago, as boyfriend two was slapping her arse, and she was getting exactly zero out of it, she decided that she needed a man that knew what he was doing, and that meant an older man—probably somebody old enough to upset her dad. All that evening she thought about it, and kept coming back to the same point: she knew a man, old enough, experienced enough, and just about attractive enough to meet her requirements. The reason she was cautious was that it was a high-risk person—Andy. Andy might freak and tell her dad in an attempt to protect himself, and even if he agreed, there was still a lot of risk. He lived across the road, he was married, and Chloe was sure his wife would not be impressed.
Then there was Max. she was friends with Max, so both location and situation caused risk. She would have to create a reason to be at Andy's; it was not somewhere she could go unnoticed. It took her three days to come up with the leadership studies, but it fitted perfectly. Andy was a successful leader near the top of a large organisation, and as part of the education part of her work placement, she needed to study leadership, and get a mentor. Andy was perfect.
By the time she went to sleep that night she had what she wanted to say mapped out. The only issue was she had no idea how to start a conversation like that. A couple of days of thinking, then she decided it would be better if he started the conversation, and started to engineer reasons for the two of them to come into contact. He ignored or missed all of them. Then, a genuine mistake, leaving her coffee on the car roof started it. It was like it was planned when she arrived home that night and his arse was pointing at her as he gardened. Everything was moving, and she planned to go apologise to get into a situation where she could ask. Then, on the day after, when she planned to do it, she chickened out. As if fate was not going to let her leave unsatisfied, the next day gave her a now or never moment, and she took it. From start to finish it went nothing like her plan; she said everything she needed to, but not one thing she planned to say came out the way she had foreseen it.
So here she was, looking at the butt plug he had forced into her, made her wear home, and she knew she had to get it back in at some point in the next two days, too. 'Fuck knows how,' she thought. Actually, she didn't care; her arse was red—she had been spanked properly for the first time in her life—and she had to do what he said. 'Happiest I've ever been,' she thought.
Chloe wiped. It felt weird; she had never used lube before. Nothing had been in her arse before either, and the feeling as she wiped it away was very strange. Her hole was a little sensitive. 'Only to be expected,' she thought to herself.
Once she was comfortable, she washed and cleaned the plug, it felt so strange in her hands as she soaped it, and then rinsed it clean. She sniggered as she dried it on the hand towel; her sister and brother would probably wipe their faces with that, tonight. She secured the plug in her hand, unlocked the door and walked quickly to her bedroom, closing the door behind her. She exhaled loudly as soon as the door was closed. She hadn't realised, but she had held her breath all the way from the bathroom to her room. She walked to her bedside table, opened the bottom draw, took out a locked box, and placed it on the bed with the plug beside it. Chloe located her car keys on her dresser; the padlock key next to her car key slipped into the lock and released the box. Inside, she looked at the two toys: the little pink rabbit, about four inches long with mouldings that she loved to bounce on her clit; and the big bully, a pale skin-tone 'lifelike' penis, about 9 inches long, and fat, with balls at the bottom.
Chloe knew he would choose the bully, when she snapped the photo and sent it to his number. She put all three things in the box, then pulled the lube from her pocket, and placed that in there too. She locked the box and put it away; she would carry out his task later, although part of her wanted to take out the rabbit and cum. She really needed to cum.
She walked out the room, saying to herself, 'I want to build the trust, and there is no point having a teacher if I am going to cheat.' She was not sure she would be believing that by Friday, but it was the intention she was starting with.
She walked into the kitchen and said to her mother, "Can I help you with anything?"
As her mother said, "Please, can you set the table?" her phone buzzed.
She looked, the text from Andy read, "You know which one, don't you?"
"The bully?" she texted back.
As she pulled knives and forks from the draw, and thumbs up came back. She settled into the evening, planning to go to bed about 9 p.m. to achieve what he wanted, but was sure she would find it hard not to cum then too.
About ten past nine, Chloe closed her bedroom door and sat down on the bed. She was both excited and scared. The idea of getting that butt plug back up was not appealing at all, as she opened her draw and extracted the lockbox. Once open, she took out the plug, the lube, and her bully. She sat looking at them for a moment, trying to decide the best way to do this, but she knew she needed to get the plug in first. She got up and stripped naked, looking at herself in the mirror before she returned to the bed. Her normal thought of, 'I should lose a few pounds,' went through her head.
As she sat on the bed it occurred to her that neither of her boyfriends had ever commented on her being fat. Boys did that, especially after breaking up, but they hadn't. However, the thing that stuck in her mind was that Andy had taken time with her curves today. He had stroked them, ran his hand over them, appreciated them, and he had not even seen her amazing tits yet. Chloe loved her tits; they were big, but pert. They sat firmly on her chest, there was no sag, and definitely no hanging down. She ran her left hand under her right boob, firm in feel, but soft to the touch. Andy was going to love them. Actually, she thought, Andy is probably going to punish them, and with that thought, she felt her pussy twitch.
Chloe laid back onto the bed, raised her knees and, with a big glug of lube on her fingers, reached down for her arse. As she moved past her pussy, she could feel how hot and wet it was. Chloe was neither as delicate nor skilled at applying the lube as Andy, and to be frank she felt a little daft doing it to herself. She tried to emulate his motions, but it just did not work from this angle. After a moment, she started to think her more 'slap it and rub' approach was actually working. All the area around her hole was very well lubricated now, she took a deep breath, and pushed her finger in.
Chloe was mildly surprised by the feeling of her finger in her arse. As she moved it about, spreading the lube, she pondered to herself. 'I really didn't like this when I tried it before, but it doesn't feel bad now. Is it different because I know I have to, because I know he will not accept failure?' While she could not say fingering her arse felt good, it was definitely better than the first time. Shame that finger was about to be replaced with something nowhere near as comfortable, at least as it went in.
She grabbed the plug, and gently positioned it. The metal was cold, but it seemed to slip on the lube OK. After a couple of calming breaths, she pushed; her hole immediately felt stretched. She stopped pushing as the discomfort was too much. In a very ginger manner, she moved the plug out, then in. It was moving fine, so it was not a lack of lube; it was her sensitive little hole, complaining about the demands she was making of it. She used a finger to measure, and guessed about half of it was in, that both impressed and disappointed her. Chloe knew that if she didn't have to take the photo tonight, she would have given up then, but this was not her choice. Master had told her to do it, which meant she had to do it. Without thinking about it, she pushed hard. The plug moved a lot, but was still not in, and she had squeaked loudly. She sat completely motionless, her arse hole burning with discomfort, listening for any indication that somebody in the house was going to respond to her noise. Thirty seconds passed and there was nothing. She could hear the TV downstairs, and there were still the tiny vibrations of bass sent through the house by the music in her brother's room, but nothing else.
Chloe started to breathe again, trying to ignore the discomfort. Deliberately and slowly, she took deep breaths. Then, with her left hand she covered her mouth, and with her right she shoved as hard as she could. Chloe, sobbed into her hand, as there was a pop of the plug making it all the way in. She felt sick, but it was done. She felt a tear on the hand over her mouth, but actually she did not care; she was really proud of herself.
