On a free evening he inquires whether she would be up for a leather session in bed. She agrees, so he already takes some leather clothes for her and puts them on the bed. The long pants and the top, as well as the cap and gloves. The cap gives her a really strict dominatrix look, guaranteed to drive Kevin wild. Some half an hour later, she comes over to the bedroom and without saying anything starts putting on the leather. The sight of the pants sliding over her fine ass make him ask to kiss it; a wish that is granted as usual. Their sessions are more about the leather fetish and his arousal with a strict dominatrix look than with actual strict BDSM play. Sure, he likes to be tied up and teased, but she is not into strict roleplay. Therefore he is usually allowed to touch her leather all the time and does not have to earn it. He sometimes would like it to be more strict, but that would be too obvious topping from the bottom. As she has put on all the leather clothes, she asks, "What do you want to do?"
He tells her that there is a fantasy that he wants to talk about while he masturbates himself and her fondling him. So she sits down next to him and lets her hands move all over his body, giving special attention to all his sensitive parts. "I would really like to cum on your leather boots," he says. This is not the first time that he has spoken about it with her since he saw those videos, so she knows how this will go and says "Well, but you know that you have no interest in licking up your mess after you have cum," which is undeniably true. And that's exactly where the new training idea comes in. While she caresses his nipples with her leather gloves, he has one hand on her leather ass and the other between his legs, stimulating himself just enough to ride the edge but not cum yet. The "Don't you want to continue telling me your fantasy?" gets him to focus a bit more on the story he is telling. Continuing, he proposes that she could feed him some precum while he is still horny. He would likely not object, especially if she would hold his chin with one glove and dig thumb and index finger into his cheeks. Then the second hand would stick a finger with a bit of precum deep into his mouth, making sure it all gets in there. After sucking it off from her finger, she would make him some humiliating complement like "Well done! If you keep being so eager, you can cum on my leather boots in no time."
While being careful not to have an orgasm just yet, he stimulates himself a bit slower. The pinching of his nipples makes it harder to focus, her gloves over his face are a sure way to make him fall deeper into his leather fetish. He continues the narrative of the training: "When I consistently suck off my precum," he shudders with a mix of fear and excitement at the words he just said, "you start to feed me just a fingertip of cum right after the orgasm. Perhaps we could start with ruined orgasms first, this way I am still very horny." She continues to fondle his sensitive parts and listens to his fantasy with curiosity. "When I am trained to a point where I don't object to small amounts, the training will continue with larger amounts." He pauses for a bit because he is not sure whether this is really heading into the right direction, second thoughts make him a bit hesitant. All the time he hopes that she would start with feeding him precum right on this evening, but so far it has not happened. Perhaps she did not get the hint, perhaps she does this on surprise at some point later?
The excitement make him swallow down the second thoughts for now. There never was any pressure or force to do something he did not like, so there was no reason to fear something bad would happen to him. "When I have progressed so far that I can reliably eat up all my cum even after a full orgasm, I would be allowed to shoot my load over your black leather boots." This seems like a distant future to Kevin, so many training steps in between. And while sucking off precum seemed like something he pull off, sucking off semen after an orgasm was quite a different thing. While thinking about it, it seemed rather nasty. But yet, he is so turned on by the whole idea that the storytelling just continues: "It would be so hot to be tied to the bed and having you sit on the side of the bed and jacking me off with your leather gloves. Perhaps even sitting on my face!" He starts panting with arousal and continues after catching his breath again, "And then after being so aroused by kissing your leather clad ass, you would let me cum into your leather clove where you formed a cup for all my load. I would not see any of this since I could only see (and kiss) your beautiful ass. You would then hop off my face and feed me the handful of cum, telling me that this is a non-negotiable part of my training."
She smiles and just asks "Would like to cum to this fantasy now?" and gladly he does. While cumming, she slides a finger of her leather glove into his mouth, making him explode all over his chest.