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Every boy is different and requires a different approach

A talk between CastroKink and MasterMarc about experiences with newbies.

MasterMarc: Hi CastroKink. It’s great to have you here with us. You are, as many people can read out of your nick, a San Francisco based Master and we want to talk today a little about the work with newbies, with guys who haven’t any kinky experiences but they feel curiosity and also kind of need to start to live their desires. But before we talk about that, I want to know a little more about you. For how long are you living your kinks, when and how have you started?

CastroKink: Hi MasterMarc. Like many kinky guys, I started doing things with other boys I did not even realize we’re kinky at the time. We were just experimenting. My earliest memorable kinky clue is of me saving jars of piss when I was about 11 or 12 years old.

I’m 1992 during college in Pittsburgh, my boyfriend and I went to a BDSM play party at someone’s house. I was put in a rack and then flogged, whipped, and shocked. Though my boyfriend didn’t get into it, I was hooked! Around the same time, I bought my first impact implement, a riding crop I had for 20 years.

I’ve always enjoyed younger, smaller boys and as I’ve gotten older, my natural craving to dominate (and mentor) them grows even stronger.

I took a long break during a 13-year monogamous vanilla relationship. Never again!

But, I’ve since aggressively made up for lost time. I play nearly every day. I am heavily engaged in the BDSM community here in San Francisco and manage a group dedicated to the technical instruction of BDSM.

MasterMarc: Yes that’s true, I’ve to say that looking back my first sadistic games started with 7 years and yes, it is hard to live a vanilla relationship without having sm. Allways in crises you feel that you’re missing something important. For how long are you now acting as master and how has to be a good master in your eyes?

CastroKink: It is difficult to say how long as it has been part of my life on and off to varying degrees for more than 20 years. My activity increased greatly after I left the aforementioned relationship in 2013. I now dom in sessions five or more times most weeks.

What makes a good master? That is not an easy question to answer as there are so many factors.

A good master is empathic. He senses and understands the feelings his boy is experiencing. He knows intuitively when his sub is in the right headspace and uses that to orchestrate a meaningful experience for both parties. The master knows that it is his job to create a safe space for his sub to be able to let go without fear of harm. The sub must trust his dom to protect and care for him while in service.

A good master is creative. I have seen several doms repeat essentially the exact same scene every time they play. That is a red flag to me. It tells me that the master is not paying attention to his sub as every sub has different needs. A good dom adapts his style to the one needed for his boy to surrender completely.

A good master has technical skill in the techniques he is using. A dom needs to know what he is doing, particularly with things that can cause serious harm if done improperly. Before a single tail whip is ever used on a sub, that master had better been practicing for quite a while. And I can’t tell you how many times, I’ve seen circulation-restricting rope ties used in ignorance. There are many techniques which require less skill and have less risk than others. I always encourage inexperienced doms to start with those. In San Francisco, I manage the Ring SF which hosts monthly workshops on technical aspects of BDSM.

A good master subs on occasion. Personally, I never inflict on someone anything I have not had or am not willing to have done to me. It is really important to understand how different things feel, both physically and emotionally.

Finally, a good master understands that his boy deserves tremendous respect. Even if I am doing a humiliation session spitting, pissing, and beating a boy, it is always done out of respect for that sub and his deep-rooted needs. And out of session, the sub must be treated with love and care.

MasterMarc: I agree with you in most of the points you have mentioned. Just the point that a good master has also to be a sub from time to time is something i don’t agree. But if he has not the sub experiences than he has to have even more empathy and sense of responsibility. But of course for many tops it can help to be a sub from time to time. How important are for you your toys and equipment?

CastroKink: For the purposes of conducting a really good session, none of my gear is terribly important. A fantastic session starts and ends with a deep exchange of power. The sub willingly surrenders control in exchange for the absolute trust in me to take care of him. I don’t need gear to do that. In fact, first sessions with a new sub are usually light on gear intentionally. While I do enjoy gear-intensive sessions, they aren’t my main focus.

That being said, I do have gear I use more often than not. For bondage, I’m very fond of rope. I find the time is takes to restrain someone in relatively complex ties is time I use to build the connection between myself and my bottom. I also enjoy the creativity rope allows versus simply clipping someone’s restraints to a cross.

I am quite attached to my bag of small plastic clips. They’re incredibly effective for building an endorphin rush. With a small surface area and medium tension, I can use a LOT of them. I have had over 50 on a sub’s balls, for example. I enjoy clip/clamp play because of the inevitability of the pain of removing them. With other types of pain play such as flogging, if the sub says stop, you stop and the pain ends. But with clips, once they are on, they are going to have to come off to end the pain. There is no way for the play to stop and the pain to fade until they do. Unfortunately, the exact clips I use most are no longer manufactured. When I heard, I bought every one of them I could find.

I recently bought a new heavy wooden strap with a nice wooden handle at a charity auction held by The 15 Association, of which I’m a member. I have been getting great use out of it and suspect it will be a favorite for decades. It make great sound when it strikes and leaves nice wide redness wherever it lands.

One more note about gear: When one of the first questions a prospective sub asks is about whether I own specific gear, it can be a red flag for me. It is often a clue that the sub is looking for a pre-planned fantasy rather than great connected play..

MasterMarc: Hehe, i understand what you mean. If a boy is asking online too much about gear I could say, that he should better go to a sex shop and wank in front of the shelving. 🙂 You have also a lot of experiences with newbies. You’ve told me, that you normally use less toys and gear in such sessions. But can you tell us about your approach with inexperienced guys? What do you talk with him before the session and how do you act when he is arriving?

CastroKink: While I play with boys at all levels, I do play with a lot of inexperienced boys. I am drawn to youth, innocence,, and open minds. The last is the most important. Sometimes, more experienced subs have their minds made up about what a scene is supposed to be like or exactly what they like and at what level. I’m an explorer. I want to go on an adventure with my sub during which neither of us know the destination. I almost always go into a session without a gameplan. I like to read my bottom and feed off the shared energy we create while we play.

Sometimes, the boys I play with are completely new to kink. Other times, they have done some bondage or other light play, but no SM. One boy I played with a few months ago had never had gay sex before, let alone kinky gay sex. I have found that I am skilled at establishing the trust needed to help a new boy relax enough to enjoy the experience of discovery with me.

Obviously, every boy is different and requires a different approach. With novices, I generally over-communicate in the pre-session negotiation. I can’t just ask him, “What are your hard limits?” if they don’t know what a hard limit is or don’t have an understanding of the types of kinks out there. I point him to my Tumblr blog which is entirely pics and videos of my play with other boys. I tell him to spend time scrolling through it then I ask him which posts turn him on the most and which scare him. I always ask what he is looking to get out of subbing.

I am also transparent and open about who I am–he gets my full name, my phone number, and my address. He is encouraged to contact other boys I’ve played with or to stalk me on Facebook. And he is encouraged to let someone know when and where he is going to be playing. This is all done to reassure an understandably nervous novice that he’s perfectly safe. I find this approach to be effective and appreciated.

The style I use when the boy arrives varies depending on what I believe is going to coax out the sub space within the boy. A few boys need a protocol-driven encounter. They need unforgiving instructions and a rigid set of rules. Most, however, need a more laidback approach. I greet them warmly at the door. Once inside, I talk about safety and safe words. Then I usually have him undress and use a lot of dominant body contact during his stripping to reinforce that his role is to be naked and under my control (and protection). I acknowledge his anxiety, often mentioning that, “Anxiety and anticipation are the same emotion.”


MasterMarc: Trust is really important and you have told us about some confidence-building measures before the action. How can you make this feeling even more intensive during you session? 

CastroKink: Good question. So much of it is instinct now, I am not sure if I have ever tried to articulate it. I’ll do my best to highlight at least a few of the things I do.

With most novices, I start slowly and communicate a ton. After blindfolding a new sub and establishing a basic power dynamic, I will start with something familiar like putting him on his knees and rubbing his face in my crotch. It is something most boys are familiar with from vanilla sex so it eases them into the scene. Then I’ll move to something a bit less familiar but not too far off. Perhaps I’ll have him lick my boots. Each of these little things will be praised gently and add to the new sub’s confidence and submissive headspace.

Once I feel the boy is in the right headspace, I’ll usually collar and cuff him to be led to a play space. The act of being led blindfolded and shackled without running into anything will add to his trust that I will not let him be hurt. Then I’ll move on to bondage. Often this is done with rope. Rope is something easy to up the intensity of at any pace depending on my sub’s reactions. With each successive binding, trust builds.

I like to do two or three scenes in a first session with breaks in between. The downtime often helps the endorphins take hold and the sub to feel at ease.

MasterMarc: Often people don’t see, how much work it is for a responsible master to handle new boys. You really need to learn to read them first. How should somebody without experiences know, what his limits are, so to talk about limits just help to know more about his experiences and taboos. But often what they say that their limits are just come out a gap of information and experiences. What is your approach in this mine field of limits and no-gos?

CastroKink: Helping a boy find and expand his limits is a special joy for me. First sessions with a novice are very exploratory. After establishing the power exchange and restraining or tying the boy, I will try various activities and watch what they respond positively too and what they respond negatively too. I watch for those subtle contractions that tell me something isn’t working and switch gears when I see them. I communicate a lot and I insist my sub does as well. I’ll check in frequently and pause play until I get a response.

I also tend to do multiple short scenes in a session with breaks in between (rather than one long scene.) I’ll use the break for a bit of care and discuss the experience so far. Then move on to another short scene. For example, the first time I played with my (since collared) boy, we started with bondage and spanking/paddling, then a short break followed by electro. After another short break, we did assplay and I fucked him. By breaking up the activities, nothing was too overwhelming for someone who had never done serious kink before.

Often boys only exposure to BDSM has been on the Internet and often that’s studio-produced fantasy porn that does not convey authentic play. They come in to my playspace with a false perception of what play will be like. It’s my role to give them a genuine experience that makes them long for more.

MasterMarc: It is really interesting to talk to you, but for now we have to make a break. We will continue our chat very soon and I’m sure our readers are also interested to read more. Meanwhile people can contact you on Recon and visit your Tumblr blog. Thank you, CastroKink, and see you soon again.


Visit CastroKink’s Tumblr.


Hey, if you're cruising on KINKFINITY, you probably know I'm the master of this fetish blog. BDSM isn't just sex for me; it's a lifestyle I've embraced for over 25 years. Along the way, I've met some fantastic kinksters—some dropping by my massive 200m2 dungeon for parties, others for days or weeks, and a few as 24/7 long-term slaves. Swing by my Bluesky account for more:

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