Untraining Yourself Ch. 03

"May I?", and he gestured at her feet, still in their plain white crew socks. She nodded, and he kneeled in front of where she was sitting on the couch and carefully tugged off one sock and then another. He held one foot in each hand and she thought she could see a faint pink creep into his cheeks. She got the feeling that he was asking for permission, and she remembered that she was supposed to be the one in charge here, the trainer, the one who set the expectations and did the evaluating.

"I'd like for you to rub my feet now, Ariel." She kept the tremor out of her voice, trying hard to channel the men who had trained her so confidently, who had been so sure of their entitlement to her body in ways much more intimate than what she was requesting. "Show me you know how to take care of a girl's feet."

Ariel closed his eyes for a moment and made a sound in his throat that was almost a purr, and when he opened them she saw a look that she'd previously seen mostly on herself -- a little fear, a little shame, mixed with desire and wanting to impress. He took her right foot in both of his hands and murmured something too softly to hear. She asked him to repeat it and he told her that she had beautiful soles.

Emily had never thought much about that before, but trying to see them through his eyes, she lingered on her freshly-painted crimson toenails, which she'd done herself the prior week. Her feet were slight, with her second toe almost as long as her big toe and her skin fair enough for the blue veins to show through.

Ariel was now rubbing hard on her arches, and she found herself crying out softly, enjoying both the sensation of his hands on her and the idea that she was entitled to this pleasure, to this act of being served. She noticed the strangeness of it -- her clothes still on, no feeling that it was her obligation to give him an orgasm the way she had with her trainers. She didn't feel like she was hiding anything from him the way she had with David, and she wasn't trying to please him the way she had wanted to with Benjamin.

He kept rubbing -- hard on her arches, then more softly on her heel and the top of her foot, then between her toes, and repeating. She sank further into the couch, occasionally eating a strawberry or having a sip of the wine. They were largely silent, but he would occasionally murmur about how pretty her feet were, or she would make little moans of pleasure, or remember to tell him that he was doing a good job. (She thought about telling him that he was a good boy, but decided that might be strange or unwanted.)

He brought her feet closer to his face and, on an impulse, she told him to kiss them, hoping that this would be a fitting and appropriate act for her to request in her role as a pretty girl taking what she wanted. Ariel nodded and began with her toes, one-by-one, before lifting one delicate foot at a time over his face and kissing her arches. He asked for permission to use his tongue, and Emily felt for the first time the sensation of big licks from her heel all the way to her toes, and the sensation was almost overwhelming -- she felt it not just in her foot, but also in the tingling of her pussy in response. She gasped out a thank you, and he smiled and told her that it was his pleasure.

After Ariel was done, he took a break and drank some water and settled next to Emily on the couch. She wanted to tell him how good that had felt, but to do so in a way that was that was sophisticated and adult and in-charge, not like a girl who was looking for his approval. She thought about what her mentor had told her that had made her feel good, and she tried to mimic that. "You did a very good job with that. It's important to know how to take care of a girl and show her you're focused on her pleasure when she's training you, and I could tell that you were doing that."

Ariel looked at her in what she thought might have been amusement, but he was smiling and he thanked her. She was encouraged by his response and decided to keep going.

"I want to see your body now." And at that, his smile disappeared, and he looked a little shy and turned-on, and Emily had to channel her mentor again. "Take your clothes off for me and show me all of yourself."

For a moment she wasn't sure if he was going to follow her instructions, but he did, slipping off his tee-shirt first and then his jeans and folding them deliberately and putting them on the table. She prompted him to take off the soft black boxer briefs that had been revealed, and he took those off as well and added them to the pile. He stood up, naked now, his arms by his sides, and Emily was fascinated by this dynamic, so exactly inverted from what she was used to. She could feel her pussy, wet and insistent, although what it wanted, she was not entirely sure of.

She heard her own voice, strong and bold, and she was not sure where it had come from. "I want to see all of your body, Ariel. Turn around for me. Show me all of you." He obeyed, slowly turning, displaying his thin, tall body for her. His penis was long and thin and hard, and she liked that he wasn't trying to cover it or hide from her. He had a long pink-and-white scar on his left shoulder blade and she wanted to kiss it all of a sudden but wasn't sure if that would be too intimate or not in line with the roles they were inhabiting.

Now that he was naked, she couldn't decide what to do with him, although she liked the idea of just keeping him that way, enjoying the display. In a training session, the girl was responsible for the man's erection -- for making him hard, giving him the best orgasm that she could, and then making sure to get all of his semen inside of her. If he ejaculated in her butt or her vulva that was fine, but otherwise it was her job to swallow it, even if that means scooping it up from wherever he had chosen to cum on her body and putting it in her mouth.

But here, she realized that she didn't have to give him an orgasm if she didn't want to. She could even have him give her one - or more than one! - and leave him hard, or she could allow him to touch himself for her, or anything she wanted could be hers. It startled her, thinking about the variety of options, until she realized that Ariel was still standing naked in front of her waiting for her guidance. She decided that, even though her trainers had never done this, that it would be permissible for her to ask him for his thoughts, since she had warned him about her inexperience.

"Ariel?"

"Yes, Ms. Emily?"

"What are some things you could... you could do for me?"

He smiled shyly at her. "I could show you how my body opens up to take a toy, if you wanted. Or I could...use my mouth on you?" His voice turned up at the end hopefully.

Emily had a complicated set of feelings about receiving oral sex. She had long inner lips that peeked significantly past her outer labia, and she'd felt shy about them for so long. Her mentor had gone to significant measures, having her practice a greeting with new trainers where she would present her pussy to them and show them whatever they wanted to see, even pulling her lips apart to display her insides if they desired. And when she, in a moment of panicked defiance, had refused to let herself be licked there, he had tied her up and she had it done to her over her objections, as she was forced to relax and accept that her body was not hers to ban access to, but rather for eligible men to use as they pleased.

Forced to bear it, she found the most intense pleasure from it, and wanted more, but she still felt a bit shy at the idea of a man with his face between her legs, seeing all of her up-close like that. Recently, David, the first man she'd gone to bed with in Canada, David, had brought her to orgasm that way, but she was already so worked up when he started that she was past the point of self-consciousness. She was not sure not what it would be like to have Ariel see her like that - how it would mix with the fact that he was the one trying to please her, and her role was to train, to evaluate, to have what pleased her. It intrigued her to think about, but she was not sure if she was ready for this.

She decided to start by having him open himself up for her and to see what that was like. She'd had anal sex before - it was something all girls in training were expected to learn - but it had never occurred to her that a man might want to be penetrated there, or even that this could be possible. She was fascinated at this idea, and she didn't want to pretend to be more experienced with this than she was. She hoped that this would not be a repeat of the condom debacle, where her ignorance about this topic would mark her as odd.

Ariel didn't have to be asked more than once, and as soon as Emily had requested this, he was ready with a bottle of lube and a red toy that was shorter than a penis but quite thick. He got on his knees, put the lube on the toy, and wiggled it into his ass until he was able to take all of it. He looked a little embarrassed, and Emily thought that she must have displayed her newness to this topic, because he asked her if she'd ever done this before. She shook her head, but he didn't seem surprised, and he pulled the toy in and out like he was fucking himself with it. Emily gasped, confused and turned-on, and when he offered her a turn, she took over and felt Ariel's ass clenched around the toy, stretched out, filled with it.

As she fucked him, it started to feel extremely right, and she could tell he was getting closer to orgasm by his soft little moans. "Touch yourself for me", she ordered, emboldened by his responses and by the feeling of penetrating him, and he grabbed his cock and began tugging on it as she continuing to fuck him with the toy. "Show me what a good boy you are for me", she ordered, and his eyes opened wide with shame and pleasure. "Show me how much you need this," she said, and finally, he had an orgasm, shooting cum all over his belly and legs as she watched.

After Ariel finished he was immediately in the bathroom, and he came out in a robe, holding the freshly-washed toy. He looked sheepish and had a little bit of the shyness from when had initially met, and Emily once again wanted to reassure him, but now had only the faintest idea of how to do that. "You were...um...a really good boy before. That was really cool." That did appear to work, as Ariel grinned and thanked her. He offered to give her an orgasm, but Emily decided she had some things to figure out on her own about the experience she'd just had.

She instead took him up on his other offer of another glass of wine, and they both sipped from their glasses, their hands occasionally held in one another's, or her head resting on his shoulder, warm and mostly silent until she decided it was time to go home. They exchanged phone numbers and she found herself reaching for a hug as he walked her out, and she pressed her body against his for a moment before leaving.

Walking home, she felt both confused about what had happened, but also more settled, more grounded. She'd been able to go on an app and have a new experience and keep herself safe, and she was proud of that. She'd been honest about her desires without feeling like she needed to share everything. And seeing the look in Ariel's eyes as she fucked him with the toy, seeing how much he needed to be filled and approved-of, Emily felt less like her training has broken her -- less like she had failed utterly to be a good girl, but was now stuck with this unique and shameful set of longings as a result of her upbringing and training-- and more like maybe her longings were not that strange, and her training had been good preparation for exploring her desires in the spirit of bravery that being a trainee had equipped her with.

When she got home, Emily saw the letter on her table where she'd left it, but it no longer made her feel the way she had earlier. She knew that leaving had been what she needed to, and while she was still grateful for some of the lessons her mentor had taught her, she no longer felt the weight of his opinion of her, and this pleased her.