Experienced Bottoms - do you ever "mentor" new bottoms?

[backdoorjimmy]

A friend texted me yesterday and wants me to teach him how to bottom. He's never done anything with a guy before aside from kissing and mutual j/o. He's getting a hotel room this weekend and wants me to teach him how to ride a dildo and techniques for getting the most pleasure. I'm also going to be eating his ass off and on while we're alone. I've never really done anything like this before, and since I'm a total bottom, I'm worried that he's coming to the wrong guy. He's not going to be able to suck any dick unless he gets someone else to come through and he's definitely not getting any dick in his ass if I'm the only one he's coming to.

Have any other experienced bottoms helped someone ease into it? What kind of advice should I give him for his first time with a top? He only started fingering himself last week and I'm worried about ruining this for him.

[kinkysuBB]

I’ve both mentored and been mentored, though not as formally as your friend is describing. In my case I taught a guy to take my dildo, which was much bigger than anything he’d taken before. And in the same week a more experienced bottom was teaching me how to take fists.

If you’re comfortable with the idea of it it can be quite fun. Just make sure he knows what you’re comfortable with and not, and be prepared to take it very slowly. If he’s never done anything at all then what you consider tiny he’ll almost certainly consider huge. I’d imagine there’ll be a lot of explaining about lube and relaxing the sphincter and probably not a lot else the first time.

[akula]

lots and lots of lube

[ErosWired]

*sigh*

I can’t count the number of bottoms who have contacted me wanting me to mentor them. I find that the vast majority of these aren’t actually looking to learn anything - they’re just too lazy to find their own Tops and they want to hijack my hotel room and get fucked by the Tops who come for me. It’s gotten to the point now that I reject all requests out if hand.

The exception to this is at the bathhouse - it seems like just about every time I go, some sheepish, uncertain babe-in-the-woods bathhouse first-timer comes into my room to ask questions. I don’t know why they seem to gravitate to me - maybe it’s just the fact that I hang a sign on the open door to my room that says “Welcome! Cum on in!” Or maybe it’s just that I worked a public information desk for so long that I radiate something. Who knows. But they come in, I sit them down, calm their nerves, and have conversations that invariably involve extremely intimate details discussed matter-of-factly until we get them to the point that they feel they can have a good time at the baths. Often there is show-and-tell (and try) with the contents of my gear bag. They can touch me all they want. Sometimes I’ll end up giving them a tour of the facility; as often as not this concludes in the steam room where I position them strategically next to some guy with a hard cock and don’t leave until the cock is in their hand. This isn’t so much tutoring as facilitating, but it at least gets their ball rolling.

I have done some legit bottom tutoring. Most of my experience came in assisting my former Master when he would do sessions with new guys, but I also mentored in a club environment, that kind of thing.

Frankly, I find teaching other bottoms how to bottom about as engaging as teaching someone how to cook an egg. I can share information, tips, advice - but success in bottoming is defined by two things (one or both of which will matter to the bottom): the sense of personal physical gratification experienced; and the satisfaction the Top experiences. Psychological gratification for the bottom is tied to one, the other, or both. But regardless of which it is, I as a mentor have no real way of monitoring that as a process along the way to tell whether the guy in my care is making any progress.

Yes, I can check off the list, has he learned how to clean out, has he learned how to relax, has he learned how to stretch his ass, has he learned kegels. Much, much harder is to determine whether he’s learned the really vital skills - how to read a Top’s movements, rhythms, sounds, intent; how to know when to open up inside and when to clamp down on the cock; when to whimper, when to growl, when to stay silent. In order to teach him any if these things, I would have to be camped out inside his head while he’s being fucked so I could mentally whisper to him, Do it now...

So, I don’t bother comprehensively trying to mentor bottoms anymore. I can help them better on a forum like this by openly (very) sharing my personal experience and letting them then go learn for themselves what only they can only learn by doing anyway. And getting them through douching training bores the- well, bores the shit out of me.

I do, however, occasionally mentor Tops on how to be effective Tops. That may sound odd coming from an absolutely total bottom, but I have had very good success in helping a few men, particularly young men lacking in experience and self-esteem, realize confidence in their role as Tops or as readily Versatile partners.

Although I freely admit that I don’t fully comprehend how Tops think and what drives them, I can say with assurance that if I take one of these Men under my wing and into the safe harbor of my cunt, he’s going to go back out into the world as a man who takes personal pleasure in fucking another man and is confident in his ability to deliver satisfaction. I can accomplish this for him in a way I can’t with bottoms because I’m able to use my own skills to teach him how to enjoy fucking for himself, and can use my own physical response as feedback to help him refine his technique in giving pleasure (or pain) to a bottom. In teaching a Top, I can achieve synergy - in teaching a bottom, I can’t.

(As it happens, I currently have an opening for a Top training spot... but then, when wouldn’t I? 😉 )

[backdoorjimmy]

10 hours ago, subBottomKink said:

I’ve both mentored and been mentored, though not as formally as your friend is describing. In my case I taught a guy to take my dildo, which was much bigger than anything he’d taken before. And in the same week a more experienced bottom was teaching me how to take fists.

If you’re comfortable with the idea of it it can be quite fun. Just make sure he knows what you’re comfortable with and not, and be prepared to take it very slowly. If he’s never done anything at all then what you consider tiny he’ll almost certainly consider huge. I’d imagine there’ll be a lot of explaining about lube and relaxing the sphincter and probably not a lot else the first time.

I'm bringing lube and a few toys I don't use anymore. I asked him if he had any plugs or dildos and he said no, so I asked if he wanted me to pass some of mine off to him and he said yes. I have an old set of 3 plugs for beginners that starts off small and goes to medium, then large. I also have a fuckton of old dildos I don't use anymore. Some of them are special to me because they were my first toys when I was a budding little bottom boy so I won't give them away, but he can have the rest.

From talking to him I can tell it's going to be a long day. He said he panicked just sticking on finger in his ass so I'm not sure how far he's going to get.

[backdoorjimmy]

9 hours ago, akula said:

lots and lots of lube

Yep! I'm bringing lot's of lube with me.

[backdoorjimmy]

9 hours ago, ErosWired said:

*sigh*

I can’t count the number of bottoms who have contacted me wanting me to mentor them. I find that the vast majority of these aren’t actually looking to learn anything - they’re just too lazy to find their own Tops and they want to hijack my hotel room and get fucked by the Tops who come for me. It’s gotten to the point now that I reject all requests out if hand.

Luckily he's the one getting his own hotel room. I'm just coming through at 4 to spend a few hours with him and show him what to do. I offered him to come to my place but he's too squeamish because my mom might be home so he's getting a hotel room. It looks like an expensive hotel, too.

 

9 hours ago, ErosWired said:

Frankly, I find teaching other bottoms how to bottom about as engaging as teaching someone how to cook an egg. I can share information, tips, advice - but success in bottoming is defined by two things (one or both of which will matter to the bottom): the sense of personal physical gratification experienced; and the satisfaction the Top experiences. Psychological gratification for the bottom is tied to one, the other, or both. But regardless of which it is, I as a mentor have no real way of monitoring that as a process along the way to tell whether the guy in my care is making any progress.

This is what I'm worried about. I'm already exhausted just from texting back and forth with him. He's really sweet but he's closeted so his idea of being adventurous is rubbing the outside of his hole in the middle of the night with his bedroom door locked. He has no lube, no toys and just recently started fingering himself. I think a lot of this is about his fantasy of wanting to be taken by a man but he doesn't know where to begin.

He said that after we finish he wants to host men in his room all night. I didn't want to be rude so I didn't tell him that he's not ready for that. I'm hoping he'll figure it out tomorrow.

 

[evilalex]

Film it.

[kinkysuBB]

50 minutes ago, backdoorjimmy said:

Luckily he's the one getting his own hotel room. I'm just coming through at 4 to spend a few hours with him and show him what to do. I offered him to come to my place but he's too squeamish because my mom might be home so he's getting a hotel room. It looks like an expensive hotel, too.

 

This is what I'm worried about. I'm already exhausted just from texting back and forth with him. He's really sweet but he's closeted so his idea of being adventurous is rubbing the outside of his hole in the middle of the night with his bedroom door locked. He has no lube, no toys and just recently started fingering himself. I think a lot of this is about his fantasy of wanting to be taken by a man but he doesn't know where to begin.

He said that after we finish he wants to host men in his room all night. I didn't want to be rude so I didn't tell him that he's not ready for that. I'm hoping he'll figure it out tomorrow.

 

Well at least you’re starting early enough that if he panics you’ll still have plenty of time to rescue your evening.

I had a guy literally run away in the middle of doing something like this recently. Literally, I went to the bathroom and I heard the front door slamming. I’d played with him once before in a threesome with a top, and then we’d tried to arrange this mentoring thing a few times (always at his instigation) and this was the first time he’d actually showed. Like your guy, super cute and wants to be a whore, but just nowhere near ready. He messaged me again tonight wondering can we hang out again but I’ve given up now.

Good luck, and let us know how you get on!

8 minutes ago, evilalex said:

Film it.

As much as my exhibitionist streak is turned on by this idea, please don’t film it, you’ll terrify him!

[ErosWired]

2 hours ago, backdoorjimmy said:

From talking to him I can tell it's going to be a long day. He said he panicked just sticking on finger in his ass so I'm not sure how far he's going to get.

Oh, Lord. This is going to be one of those deals where (if he actually goes through with this at all) you’re going to have to sit him down somewhere comfortable before any clothes come off and before you open up you bag of gear, and just talk. All the texting you’ve done doesn’t mean a thing - you’re going to have to show him that you absolutely will not hurt him and will not let anything bad happen to him in the whole experience.

He may think he wants to be taken, but right now, he needs to know that he is in complete control of everything that’s going to happen, even if that means he decides it’s too much for that evening and calls a halt. Be prepared for your long night to potentially be a short night.

2 hours ago, backdoorjimmy said:

he's closeted so his idea of being adventurous is rubbing the outside of his hole in the middle of the night with his bedroom door locked. He has no lube, no toys and just recently started fingering himself. I think a lot of this is about his fantasy of wanting to be taken by a man but he doesn't know where to begin.

If this is his current stage of development, I’d say him getting a hotel room and asking you to come do some demonstrations is his equivalent of me throwing all good sense out the window and agreeing to let a dark, angry-looking Top with “Fag Killa” tattoed on his bicep tie me up, slam me, and whore me out to a large, violent street gang for an entire weekend.

 In no way is he ready to take anon cock in a hotel room, and it probably wouldn’t be safe to leave him to do it, even if the security measures at the expensive hotel were such that an anonymous stranger could get to the room in the first place. Not telling you what to do, but if I were in your place, I would tell the guy (assuming he hasn’t bolted on you before this) that you think he’s sexy and plucky and hot, but let him know straight-up that he’s got some experimenting and self-discovery still to do before he’s anywhere near ready to try what he’s contemplating.

1 hour ago, subBottomKink said:

As much as my exhibitionist streak is turned on by this idea, please don’t film it, you’ll terrify him!

I concur. Absolutely do not take a camera. If the way you describe your friend is anywhere close to accurate, he is in a very vulnerable place right now. Tread carefully.

One other practical tip, by the way - take all those hand-me-down dildos you’re planning to give him and run them through your dishwasher before you pack them up. Better to make sure everything’s squeaky clean. You’ll be dealing with virgin ass, after all. 🙂

[Ozpig]

I began mentoring bottoms for my ex - particularly in helping them get fucked properly, encouraging them to take him raw and helped several through their discomfort from his thick 8" cut  cock. I quite got off on it, particularly with the many young Asian boys (which he ended up having an absolute bent for) and I also enjoyed watching their transformation from shy young guys having difficulty to becoming cumsluts for him

[Guest Graham]

I would absolutely love to bottom I have tried a few times recently but I am way too tight , I used to bottom 18 years ago and was fine not sure why I have a problem 

[Pozguyinchi]

I have younger 20 somethings ask for my advise from time to time. I am more than happy to mentor them. When I was in my early twenty’s the only poz guys I knew were in their 40s and 50s and from a different era. It’s nice to have someone closer to your age to relate to.

[bbzh]

I realize from reading all these posts that there are levels to this. And everyone has their own journey from Beginner to Intermediate to Advanced Bottoming. For me, the basic themes would be diet, how to clean out, playing with toys, importance of lube, how to relax, and setting boundaries. All too often bottoms get conditioned (mostly through porn) to think they must give up agency over their bodies once they allow themselves to be penetrated. Wrong. I am not going to put up with abuse or pain for someone else's gratification. Never have, never will.

As beginning bottoms advance to the next levels, one can add in special topics like poppers, shower attachments, lube injectors, finding a lube they as bottoms enjoy, best sexual position for their pleasure, PrEP, gang bangs, anonymous hook-ups, and let's not forget sexual health especially if they aspire to be cum sluts. Gotta know where to go get those infections cleared up or have those warts removed. 😆 

[evilalex]

🙄