NOTE: This content is intended for over 18 year old readers. If you are not over 18, please click here. The term “boy” in the leather and fetish vocabulary and in this article refers to an adult male who acts as the submissive to a more dominant, “older” man, usually referred to as Sir or Daddy.

Artwork by Joan Sarria (@joan_sarria)

I currently train two leather boys. One is my long-term partner and the other is a young man in his early thirties who has a partner of his own but who wants to submit to a leather daddy who can walk him through proper training procedures.

Part one of these notes focuses on the overall planning and the “storyline” i am trying to evoke in a training session. Part two will go through some suggested tips i have learnt along the way so far.

Creating Meaning in Boy Training

Last year, i was fortunate enough to have an erotic mentoring session with author and sex psychologist Don Shewey. We discussed what being a leather man meant to me and what i want to share and evoke with my boys when in a play or training session. Being an esteemable man, to me means holding myself with confidence, treating others well, and harnessing my masculine power so that i am respectful towards women, and an advocate and protector of the marginalized. Being a leather man/daddy means i give myself space to unleash the strong, dark animal instincts within me and enjoy my body and sexual energy in a way that tests my ability to use my power without overwhelming others with it. It allows me to experiment with a balance of strength and managing control. It lets me explore men’s bodies, inside and out, and to take responsibility for the pleasure of another.

When i am training a boy, i take them on a hero’s journey. There is a call to adventure, a meeting with the mentor, and a crossing of the threshold. Then there are a series of small tests to pass and an introduction to some allies. During this time, i repeat details of some culminating ideal, trying to evoke a sense of the boy needing to enter their innermost cave (“I am going to paddle your butt cheeks once for every year of your daddy’s life”; “Are you ready for your hole training, boy?”, etc). The ordeal then takes place. The reward is then seized, a resurrection and a return to the ordinary world with an elixir.


I like to start training with a pre-meeting some weeks before our first actual training session. During this discussion, we set some boundaries. I like to get a sense of what my boy wants out of the training and some of the things they are into. For example, one boy mentioned he doesn’t like humiliation, another said he wasn’t into pain.

One wanted to submit whole-heartedly, to be able to trust, and allow himself to be taken care of. During our discussion, i got a sense of how he analyzed everything and seemed to be in a constant process of assessing how well he lived up to his ideal of himself. I did know him a little outside of our training discussion and had observed this about him then, too, he reminded me of what it was like being in my late twenties and wanting to impress, reveal myself as i truly was, but also afraid that if i did so, that wouldn’t measure up or be appealing or understood. That self-critique and judging every action is exhausting. For this boy, i wanted to provide an experience where he would be drawn into his body through a mix of sensations and instructions so that for our training session he didn’t need to get caught up in his head so much. I wanted him to relax and just be content in himself and feel his body and see it appreciated by a man that i know he respects.

Another boy wanted to revel in his fetish, to try different kinks and see what he liked, to be opened up a little and be shown leather play. He wanted to be collared and to embrace his inner boy and please another man through service. For him, i wanted to plan a more scripted session of being interviewed to be a boy-in-training, being available for inspection (more on that below), and to be walked through a variety of different experiences so that i could gauge which pleasures really set him off.

Before a play session, i like to organize a catchup chat in advance to get a feel for where they are at. I like to see what their current pressures or stresses are, where their head is at, and how they are feeling generally in case i need to alter the training to address a particular concern they have at present. For example, one boy has had some personal issues i won’t go into, but as a result of our discussion, i planned a longer training session so he could just completely give over and unwind, without having to think his way out of his situation.

Goals in Boy Training

Training a boy is about taking someone on a sensual and sexual adventure in which by the end, you know yourself a little more, accept who you are, and can embrace and relish the joy of being you. One of the realizations i had when i read Loic Wacquant’s Body & Soul: Notebooks on Being an Apprentice Boxer, is that when someone steps into a boxing ring, there is no role or persona they get to hide behind. It is basically them as a human, in the moment, needing to physically respond and fight for oneself. In leather boy training, there is a role, one that is taken on willing: to be open and present and to give of oneself to another. But it is essentially you. What you do at work, how you behave or see yourself in your social circle, the story you let others see about you, all of that is stripped away. In leather boy training there is just your body and your physical presence in the moment. I love the contemplation: “Who are you when no one is watching?” My goal in training leather boys is to help them prepare to face that question whenever it arises. I want to give my boys a chance to sink deep into their bones and their bodies so that they can trust themselves and be able to act instinctively from who they really are and the values they hold. Take takes time, i believe, but is the longer term goal of training a boy.

The Hero’s Journey

The Hero’s Journey is the central plot of most leather boy training sessions. Here is how it breaks down in a training session:

Journey Stage: Training Notes

Call to Adventure Pre-training chat and discussion of goals and any new kinks interested in exploring for the session, I get to gauge where the boy is at in terms of what he needs from a session: to feel protected, to push his boundaries, to release himself from his thoughts and self-analysis, etc.

Meeting with the Mentor This generally takes place via text or by speaking quietly directly into the ear of my boy while i am holding him during dates or meetups between the pre-training chat and the training session date. I like to stir up the sense of desire by walking my boys through some of the activities we will do and by setting some requirements such as what jockstrap and socks to wear. I usually tell them what i want them to do when they first arrive.

Crossing the Threshold I like to receive my training boy when i am wearing my full leathers. I have prepared the playspace ( see Part 2 ), and have set aside an entry space, for example, i have cleared the living area and placed a chair for the boy to put his clothes on. I like to insist that, after a welcoming kiss, my boy comes in and strips in front of me and puts his clothes on the chair and his hands behind his back, ready for inspection. The boy has “crossed the threshold” and has now entered the training space with a fresh and clear mind.

Small tests Now starts the series of small tests. This usually begins with an inspection. When my boy is naked and standing to attention, hands behind his back, i usually get him to turn around for me and spread his ass cheeks. I might lick his crack or tongue his hole for a minute, slap his butt cheeks, run my hands up and down his quads. I inspect his body slowly, tweaking his nipples, licking his pits.

Then i get him to remove my leathers for me. He will take off my vest, then my shirt (i usually have a harness underneath and an arm band above my left bicep). I get him to kneel in front of me and i put one boot on the center of his chest. I might get him to lick my boot for a bit, then remove it. Then the other. After removing my pants, i am usually in a harness and jockstrap. I put my boots back on or sometimes swap to a pair of black kicks which are sometimes less clompy to move around in for later.

During this stage, we set a safe word, i get my boy to repeat it, and i start testing the threshold of his comfort level. I usually put nipple clamps on him, spit down his mouth, roughly turn him back and forth. Sometimes i am keen to feel the inside of his hole so i might roughly fuck him for a short while.

Introduction to allies Now we have time to introduce some of the playthings. I will usually put wrist and ankle restraints on him at this point. I will show the boy the paddle or flog i intend to use on him, introduce him to the sling, and any toys i plan to use on him, usually some form of ass-widening plug or pig hole.

Entering the innermost cave After the thorough inspection, some forced cocksucking, maybe a little bit of fucking, and the introduction to the toys, i will now usually bring the boy into the sling space area. There is usually some form of restraining at this stage. Lately i have been using gags with my boys which is fun. One boy in particular immediately goes into an ecstatic trance when there is a gag around his mouth, i think it is a culmination of everything he has envisioned as part of being a boy-in-training and he relishes living his dream. I will also tie the wrist restraints to the sling frame, preparing the boy for flogging or paddling.

The ordeal Part of the work of being a leather master is to cultivate a creativity that allows a boy to activate all their senses (come to think of that, i perhaps don’t use smell enough, apart from making my boys sniff deeply at my undeoderized armpits). The ordeal is a combination of pleasurable and painful sensations that raise the boy’s connection with their own body. There is an aspect of total submission in the ordeal, where the boy must just give over and trust their master and offer themselves totally.

The ordeal usually involves butt paddling, interspersed with light flogging, some nipple twisting, and rough handling in which i unhook the boy from his restraints and force him to suck my cock before he climbs into the sling, is restrained again, and brutally fucked by me and by me and a combination of toys i deliver into his hole.

The reward There are small rewards given throughout the ordeal. I have taken to applying ice cubes to a boy’s buttocks after the paddling, and i will often blow gently on his reddened ass cheeks as i rub the ice cube around his stinging butt. Of course, the brutal fucking is itself both an ordeal and a reward, and at the end of the session, being responsible for seeing his Sir/Daddy cum is the ultimate reward.

The resurrection The boy now gets to cum himself. I have a personal rule where bottoms aren’t allowed to cum first, but sometimes i do make my boys cum while i am fucking them, although i prefer it to be more like a resurrection, a return to their own power. After the fucking and paddling and ordeal, and having brought me to pleasure, my boys are usually high on the the sensory pleasures, and the endorphins of their experience. I let them suck my post-cum cock or hold me and kiss me as they cum up against me. They are arising anew, relishing in their own power and confidence of what they have gone through and what they have offered for the joy of another man.

The return to the ordinary world with an elixir I like then to bring the boy back into the living room, maybe with towels down on the couch first, where we sit, my arms around the boy while our breathing returns to normal. We share a joke or two about any fumbles i might have made (i usually bring this up as a way of reminding us both that we are humans, its not a porn act, shit happens but doesn’t detract from the experience in any way). I ask the boy what he got out of it, what he liked the most, etc. I usually compliment the boy at this stage, which is their elixir, in some ways, reminding them of their growth into a leather man in their own right. I usually have a present for my boy at this stage. For my own boy, every few training sessions, there is a gift of a new item of leather. Last training session he earned a leather jockstrap and now he is allowed to wear it whenever he chooses, not just when i tell him, as is the case with other items like his collar.

Final Training Prep

After i have worked out the hero’s journey for a training session, i take a few notes for myself, like a dot-point script, and i run through the scenario in my mind (see Part 2 for some of the do’s and don’t’s i have for this final planning).

Boy training is a little different to usual fetish and leather play. In fetish and leather play, it is about celebrating one’s kinks, and while each partner may take on a role (dom/sub, daddy/boy, trainer/pup, etc), that is just about good, wholesome fun between two consenting adults and their toy inventory. Boy training has a goal for the session in mind and uses sex and sensory experiences to encourage confidence and self-actualization.