Training a Beginning Top - Advice Please

[ErosWired]

I find myself in the unusual position of training a 21-year-old guy how to Top. I, of course, am a total bottom, so it's not unlike a horse teaching horseback riding, yet here I am.

The guy is very interested in Topping, but for whatever reason has performance/ED issues when it comes down to the moment. We have established that he has no problems with his actual plumbing, and indeed he has an exceptional young cock, beautifully symmetrical, thick, straight, and yummy. His cum is also absolutely delicious. He approached me on Grindr (yes, I know) yet wonder of wonders, he was real, and appeared, on time, as described. Quite mature, and serious about wanting to Top me... if possible. He wanted to make sure I understood that he might not be able to, and I assured him I had no expectation other than that we would have fun getting to know each other.

He had not tried Viagra before, and after making sure there were no obvious contraindications (happily, he's a student in the medical care field, so was quite knowledgeable himself) so we agreed that he might try a medium dose to see if it assisted him with whatever problem might be affecting his erection.

It assisted.

Cutting to the chase, he fucked me very well indeed, shifting positions twice, finally lasting with a loud groan and collapsing into me in a sweaty, gasping heap. He said, "... After 30 failed attempts..."

1) Kudos to the man for getting back in the saddle again after 30 failures; and
2) Damn, he must really want to Top.

And yet, in the two weeks since, he hasn't tried again with anyone else. He says he wants my ass again tonight after 9pm. He says he hasn't shot in a week and needs to cum. I've told him all along that my ass is his for the taking whenever he wants it (how many 21-year-old guys have a dedicated ass to fuck?) but he hasn't been aggressive about taking advantage of it.

My question for all of you:

What advice would you give to a young man about how to Top? I can only advise him from a bottom's perspective, about what makes me responsive as a bottom, and about what I hope I supply for him in the experience. I can't guide him in how he should think of bottoms, what his approach toward them should be (other than what I hope happens to me), or any of those secrets only Tops know about bottoms and their asses. What would you say to a young man to give him the confidence to come in with a raging-hard cock and fuck like a champ? Because he has the potential.

Advice from Tops is especially sought, but all replies are welcome.

Edited February 27, 2019 by ErosWired

[phukhole]

It's obviously some mental issue that is keeping him from performing.  With help, he was able to get there and he enjoyed it (or he wouldn't be cumming back around). This makes me think that he hasn't come to terms with his same sex attraction yet.  He is probably still internalizing all the 'this is wrong" and "that's not normal" crap he's heard all his life.  I'm not sure it's a confidence thing, per se, though that could be part of it.  Makes me also wonder if he had some bad experiences with other not so understanding bottoms.  Long and the short of it is, he needs to feel comfortable and the only way to get there is practice.  You may need to make the first move and tell him, "I had a date that feel through and am SO horny.  Wanna cum over..."  He might not have believed you were willing to be his dedicated hole.  Play it up and hit him over the head with the fact that he can fuck you any time.  That's what I'd do!

[Read1]

This young, remarkably endowed young man, needs to be relaxed. No doubt about it. Have you played with him -- sucked on his tits, played/rimmed his ass, licked him all over with your tongue, etc. to see where his erogenous zones are? Beside him fucking you, do you allow him to play with you all over? A little exploration might just get him to relax, achieve and keep erections so he can go on to fuck and fill your hole. Turning your encounters into play time on repeated occasions might just awaken for him the beast (and sex pig) from within. Best of luck! OINK!

[ErosWired]

23 minutes ago, Read1 said:

This young, remarkably endowed young man, needs to be relaxed. No doubt about it. Have you played with him -- sucked on his tits, played/rimmed his ass, licked him all over with your tongue, etc. to see where his erogenous zones are? Beside him fucking you, do you allow him to play with you all over? A little exploration might just get him to relax, achieve and keep erections so he can go on to fuck and fill your hole. Turning your encounters into play time on repeated occasions might just awaken for him the beast (and sex pig) from within. Best of luck! OINK!

I concentrated on relaxation the first time, beginning with massage and slow tongue work over his torso. I always explore all my Tops’ exogenous zones (if given the chance) to find out what stimulates them most, and what doesn’t. With a man this young, I’m not sure he knows his own body well enough sexually to be sophisticated about his responses - and I don’t want to overdo it and scare him off. I think I can help him become attuned to his sexuality, but I’m not sure how to encourage the “Top-ness” in him, if you get what I mean, as I have no Top in me whatsoever. For instance, if he were to ask an Alpha what he should do with a bottom, what would an Alpha tell him? (And no, I don’t think “Get out of the way and let a real man fuck him” would be all that useful in this situation, however appropriate such advice might be.)

[Read1]

You're correct in taking baby pig steps. Another suggestion: as he plays with your body be verbal (slowly and increasing a bit each bb sex session), and encourage him to be verbal if he likes/loves something you're doing to his body. His nipples may not be attached to his boycock, but I'm sure that other erogenous zones are! Just my further two cents. Best of luck!

[Anonversecuck]

So hot to have an ass to fuck anyone you want it

[InsatiableBoy]

One positive experience may not be enough to counterbalance his negative experiences, so I'm in agreement it's likely psychological. I don't want to make any assumptions about how he is with his sexuality, though that could be a contributing factor. Spur of the moment doesn't seem to be working for him, and although he wants release his current performance anxiety seems to be in conflict with his desires.

My suggestion is to build his anticipation. Schedule a time with him let's say a week from now and tease the ever loving shit out of him the entire time. A while back I was talking with a Dom, and after an initial inspection, he sent me on my way with the plan to play a week later. He'd check in with me daily, have me show him how excited I was, and even had me train throughout the week. My training was to edge myself but not cum two to three times a day until our scheduled time, and I was absolutely forbidden from cumming at all until we met. By the time we actually played I was rock hard from the time I headed over to his place until he finally let me cum. Not to mention I was so horny I was ready to obey commands before he even issued them.

Now this is obviously not something a sub would ordinarily do, and also turns the whole D/s dynamic on its head. However if you're committed to helping him through this you might consider tapping into your inner Dom to make it happen.

 

[ErosWired]

36 minutes ago, InsatiableBoy said:

Now this is obviously not something a sub would ordinarily do, and also turns the whole D/s dynamic on its head. However if you're committed to helping him through this you might consider tapping into your inner Dom to make it happen.

Your points are well taken. Unfortunately, and I say this with complete conviction, I have no inner Dom, of any kind. That’s the main reason for this topic.

He has, as it happens, just left after our session. I tried to get him started with some foreplay, but he was eager to fuck, so I figured, strike while the iron is hot... as it were.

He was erect to begin with, had a couple of false starts when he had trouble  zeroing in on my hole in doggy position, and he asked if he could have a Viagra. I gave him what he asked for, but I knew he didn’t need it; I assumed missionary to give him better access, and he was plowing me waaaaay sooner than that V would have had any time to act. He flipped me to a couple of different positions, then asked if I wanted his cum in me.

When he came, it was like a convulsion, and his voice went up in pitch, then he shuddered and went still for a bit, until I felt I needed to ask if he was okay. He replied that he had just had the most intense orgasm of his life. (Naturally, I would love to credit the unique qualities of my ass with this result, but modesty forbids. )

In the afterglow, after I tongued him clean, we spooned and talked for about an hour as I worked on getting to know him better, and getting him to feel more comfortable with me. Time well spent, I think, especially as I learned that he had been feeling bad because he felt like he was using me just for sex (!!). Bless him. I think I got him straightened out on that score - in any case, he wanted another look at my ass after he got dressed.

Yeah, he’ll be back. The sex is pretty fucking good. ?

[hungry_hole]

11 hours ago, ErosWired said:

I find myself in the unusual position of training a 21-year-old guy how to Top. I, of course, am a total bottom, so it's not unlike a horse teaching horseback riding, yet here I am.

He may a bottom. Imagine yourself at 21 years old and someone trying to train you as a top. Why would you assume he's a top?

[ErosWired]

4 hours ago, hungry_hole said:

He may a bottom. Imagine yourself at 21 years old and someone trying to train you as a top. Why would you assume he's a top?

He came to me specifically because he wanted help Topping.

[Pozlover1]

I just lick their butthole

[Bwccummer]

Not sure what hang up be. My guess is can be stress if a student in studying. Next could be psychological in being able to perform. I can only share my experience. I think a reason first time trouble as a top was had some psychological issues to deal with. 

I think subconsciously at time had thoughts of feeling this is wrong. Also at time still think of hear how is a sin and in the Bible. Also had worry of keeping discrete and if worry others hear can effect performance. 

Over time in with other guys start to learn to perform. Note wrote about, but took a few guys in trying to top until find someone felt comfortable enough and patient. Now I can top or bottom. I no longer have feelings of sin, guilt or this is wrong as long as both are adults are 18 and older and consent.

Best advice is not push or rush. As others posted may need to contact are available.

He may also worry if reliable or not. Sadly many flake or just never show up. Reassure the times are available. Last advice is use a lot of lube. The time I was a bottom had to use a lot of lube to get his thick long 8" inches or so girth in my hole.

[Qban]

I’m intrigued by the concept that someone would need to be “trained” to be a top; I always thought most people top or bottom based on their personal preference and/or the dynamics of the situation - at least that’s always been the case for me.  I never feel any shame when I want to get fucked or think any less of the bottoms I fuck who really enjoy it.  I think if he’s ashamed of it then it’s either not for him or it’s something he needs to deal with in his own head before brining someone else into the picture.  If that’s the case, just being trained in the mechanics of topping sn’t going to help.  Of course if he gets off on doing things he’s ashamed of it’s obviously a whole different ball game...but it doesn’t sound like this is the case.

[ErosWired]

2 hours ago, Qban said:

 

I’m intrigued by the concept that someone would need to be “trained” to be a top; I always thought most people top or bottom based on their personal preference and/or the dynamics of the situation - at least that’s always been the case for me.

 

I was surprised by it too, and sort of intrigued, to the point that I want to know what’s going on with him. As I’ve mentioned elsewhere, the Top mindset is a deep mystery to me, and to encounter a young man on the cusp of it may offer me a chance to get some insight into how it develops.

Or not. He’s not a big talker so far, so it may take some time...

[find91]

2 hours ago, Qban said:

I’m intrigued by the concept that someone would need to be “trained” to be a top; I always thought most people top or bottom based on their personal preference and/or the dynamics of the situation - at least that’s always been the case for me.  I never feel any shame when I want to get fucked or think any less of the bottoms I fuck who really enjoy it.  I think if he’s ashamed of it then it’s either not for him or it’s something he needs to deal with in his own head before brining someone else into the picture.  If that’s the case, just being trained in the mechanics of topping sn’t going to help.  Of course if he gets off on doing things he’s ashamed of it’s obviously a whole different ball game...but it doesn’t sound like this is the case.

There's a big difference being a top and a competent or good top. That aside he may be starting to explore his sexuality and honestly bottoming looks painful and sounds complicated with all the douching and shit. So It might scare him away from trying to bottom. IDK just throwing out a theory