How to Become a Legendary Sir

Hundreds more articles like this can be found

at the Kink Mentoring Archives… Spread the word!

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Papa Tony:

First off, I recognize the amazing arrogance of the subject line.  Who the heck am I to claim any inside information on becoming "legendary"?

Well, it happened to me, and now, decades later, I gladly give away my trade secrets.

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After twelve excruciating years of being in the Catholic school system in the 1960's, I graduated with a painful understanding of just how unprepared I was, for the real world of being a kinky gay male.  Going to the prom with a girlfriend (twice) had zero relevance to a young leatherman briefly living in Boys Town, West Hollywood in the mid-1970's.

First, I tried to learn from men my own age, and that was a bust.  Most of them were just as lacking in wisdom and sophistication as I was.  Then, I found older leathermen, and I discovered exactly how to get the hard-earned wisdom that would sustain me for the rest of my life:

I asked nicely.

After every single play session, I'd ask my playmate "How could I have done that better?"  Every man found this flattering and encouraging.  In fact, I can't recall a single time that somebody didn't honor my request in the spirit in which it was asked.  However, keep in mind, forty years later, my memory may be faulty.

I mentor younger gay leathermen every day.  Imagine me wearing a t-shirt that says "MENTOR" across my chest.  I don't OWN such a shirt, but I'm making a point here:

Now, imagine your playmate/date/trick wearing an invisible version of that same shirt.  When he gives you an after-play "report card," he is handing you big handfuls of what you need the most:  FEEDBACK.

Feedback leads to wisdom, which leads to confidence, ending up with serenity in your role as a Sir.  Nothing is more sexy and attractive in a Sir.  Truly.  Muscles, money, penis size and $3,000 outfits are all VERY nice (I've had them all, in the past), but confidence, kindness and charisma are what impress the boys the most, for the long-term. 

Pay close attention to what your sub says. Honor his opinions, even if you had a different perception of what happened.  Be open to differing perspectives.  His viewpoint is honest, and richly valuable.

In fact, after a play-session, it's a great idea to order an eager submissive to send you a detailed email before he sleeps tonight, listing what he liked (or did NOT like), and why. And how strongly he feels about it.

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So, back to title justification:  How does this lead to any form of "legendary" status?  Easy!  Being known as a sensitive, perceptive and attentive Top will result in bottoms flying at you butt-first from every direction, and dropping hankies and soap everywhere that you go. Your dick will get smaller, because you will be getting laid so much, you will be wearing it down like the eraser on a pencil! Before long, you will be leaving men smiling at both ends, every time! 😀

Back to being serious:

- YOUR VALUE WILL NEVER DECREASE. You know how older gay men can spend a lot of time complaining about becoming old and undesirable? That doesn’t apply in the case of a Sir who has been actively gaining wisdom, and a sterling reputation. I can be the oldest guy at the play-party, bar or other social event, and eyes will be shining, and tails wagging all around me, hoping for a chance.  This advice really, really works, brothers.

Here is a secret:  The sub trains the Sir.  Yeah, yeah - every porn video says otherwise.  After nineteen collared boys, and multiple collared slaves, I am STILL learning the craft, and I am learning it through the desires, quirks and valuable feedback that I gain after every session.

I STILL ask.  Nicely.

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Check this video to see how to get feedback DURING a play-session.  That way, everything flows well, everybody wins, and nobody complains afterward.

Tips For Leather/Fetish Swap Meets

Hundreds more articles like this can be found

at the Kink Mentoring Archives… Spread the word!

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Papa Tony:

I shared this with the young Sirs that I mentor, and I figured that it was worth sharing here, as well:

Local, kinky affinity groups periodically host Leather Swap Meets.  In San Diego, we have Club X  (website) and FetishMenSanDiego (website).  We also have a private individual who has been stepping into his power as a community leader.  The picture above this shows a typical, large and successful event.   I can't wait!

These swap meets are not meant as a profit center… just a courtesy for local kinky players who want to prioritize, and clear up some space in their closets, toy chests and dungeons.  If you don't belong to your local affinity group, I recommend at least getting their newsletter, or following them on Facebook or Fetlife.

One good, solid Swap Meet can be a delightful way to fill your toy bag, play-space or closet with gear, at a fraction of the normal cost.  Plus, your new acquisitions comes into your life a bit well-worn and LIVELY, with the history of the player who passed it along to you…

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Arrive early. Don’t let other people scoop up all the good deals before you get there.

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BRING CASH. The sellers are not corporations, they are generally heavy kink players, and they don't take credit cards. If you don’t have enough cash, leave a deposit to reserve the sale until you can get back from an ATM.

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If it fits you, and if it makes you feel sexy, BUY IT NOW!!!!! Don’t say “Let me think about it” and wander away. You’ll see it next on somebody else, wearing a big smile, and wearing YOUR item. You’ll never see it again. The regret can be terrible.

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Ask every vendor if everything that they have is on the table. I’ve lost some excellent deals, because there was some great stuff that I didn’t see before I passed on... such as a SUPERB Mister S Leather Sleep Sack in perfect condition (sold new for $1,699).

For fifty bucks.

The seller had it in a wagon behind him. I didn’t know this until he had agreed to sell it to another guy first. I was courteous and calm, but inside, I was furious with myself for forgetting this simple rule.

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Don’t badger the vendor for a better price. It ain’t that kind of scene. These are usually well-known and respected community members.  You’re gaining a big bonus already, by gathering part of their Tribal history into your life.

A friendly interaction can gain you points in the local community. A competitive, zero-sum hard-driven bargain can cause bad ripples. YOU may not know the vendor, but a lot of local movers and shakers DO.

I’ve seen many of these Leather Swap Meets. I’ve never seen any bad prices. Only excellent, gratifyingly low prices.  Have a great time!

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Let’s assume that you are open to buying uniform gear, you authority-figure fetishist, you.

If you find a uniform shirt with great insignia, emblems, patches or badges, BUY IT NOW. The way that it fits your body is immaterial.

The decorative items attached to the shirt are what is valuable. Buy a shirt from a uniform store, or online, and of the same design, that fits you reasonably well. Bring both shirts to a local tailor. Have them swap the insignia, and tailor the new shirt to conform beautifully to your shapely form.

Money well spent. HOWEVER…

Right after 9/11, everybody was putting firefighters and police on a pedestal, and they got arrogant.  In the state of California, the right-winger, anti-gay First Responder types lobbied to get a law passed, and they succeeded. Their logic was: “Gay men are RIDICULING us by wearing uniforms!”   Pound for pound, uniform gear is more expensive than leather. So, I am NOT going to spend thousands of bucks to make fun of somebody.  Really.

So, it is now a $1,000 misdemeanor to wear California insignia if you aren't an official.  This doesn't seem to apply to outdoor Halloween parties, but it's pretty serious the rest of the year.  To get around this:

- Wear a jacket on the way to your next uniform party.  Or,

- Get all of the insignia that you want, that applies to any other jurisdiction.  My own New York Corrections Officer gear seems to draw admirers, just as well as my CHP gear.  "Oh, OFFICER!  Arrest me!"