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

[backdoorjimmy]

On 8/28/2020 at 8:23 PM, subBottomKink said:

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!

 

This is almost exactly what happened. He texted me yesterday to call it off because he was too nervous. He said he rubbed his hole and it felt uncomfortable, so he didn't want to go through with it **(sigh)** At least he let me know in advance not to waste my time trying to help him.

After that I gave him some real talk (at least from my POV). I told him that the only person who can teach him about anal is either:

1. Himself, through experimenting and exploring. Or,
2. A patient lover who will take their time and keep him comfortable while they try things that are new to him.

I told him that asking another bottom for help is going to be a huge waste of his time. I like hanging out with him and I'd love to eat his ass anytime he wants me to, but I'm not going near his hole until he's sure that's what he wants.

 

[ErosWired]

6 hours ago, backdoorjimmy said:

I told him that asking another bottom for help is going to be a huge waste of his time.

That was diplomatic. Asking another bottom for help is going to be a huge waste of the other guy’s time, that much is obvious. He’s not going to make much progress of any kind until he gets his own head untangled.

[kinkysuBB]

So, advancing this a little bit. The guy I mentioned above, who was “mentoring” me in fisting, taking bigger toys, etc. has suggested we start doing it again. I’m certainly keen.

I wonder is this different though? He initially did this for me in the context of a group party we were both participating in anyway (it was the same with me “mentoring” the other bottom I mentioned). It’s also more of a mutually beneficial thing, because he’s also teaching me how to be a top for FF/toy fucking, which curiously enough I’m enjoying.

There’s no doubt it’s someone with more experience teaching someone with less. But I’m not exactly a virgin.

Have people done this successfully at a more advanced stage?