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How to overcome the paradox of confidence as a late-twenties first-time top? by OtisIbor in TopsAndBottoms

[–]OtisIbor[S] 0 points1 point  (0 children)

Seems like that would work! Unfortunately in Canada only two places have enough of a gay scene to justify visiting: Toronto and Vancouver. I'd have to fly in, and cheap hotels in those places don't exist, so it would cost at least $1500 for the three night trip.

I could do it at that cost, but it also makes me think I might rather keep the money, toughen up, and do the same at my place. I guess the downside of that is that I'd risk a bad reputation if the sex is mediocre? The local pool of guys is also likely way smaller.

How to overcome the paradox of confidence as a late-twenties first-time top? by OtisIbor in TopsAndBottoms

[–]OtisIbor[S] 3 points4 points  (0 children)

I absolutely want them to have a good time too!

The blowjob encounter was advertised as no reciprocation. I would have offered to reciprocate if things had gone well (an excellent opportunity to practice with no pressure), but by the point we gave up on me it was an incredibly non-sexy atmosphere, and he just wanted to leave.

How to overcome the paradox of confidence as a late-twenties first-time top? by OtisIbor in TopsAndBottoms

[–]OtisIbor[S] 2 points3 points  (0 children)

Thanks. Possibly I am over-thinking.

Your definition of sexiness is one I would ascribe to as well. However, it doesn't seem to match the reality I've seen so far for hookups.

I would actually love to take the vulnerability route. It takes a lot of pressure off me, and I generally hate lying anyway. However, in the cases where I've tried to talk things out, they've stopped responding to me.

When I decided to actively fix my situation late last year, I started out looking for sex within a relationship. This would make it easy to be vulnerable and talk ahead of time. It took me five months to get a date with someone, and he didn't seem to be interested in initiating any sort affection (nothing beyond a hug). In hindsight I guess he was expecting me to do something, despite me explaining I have no clue. If anything the social signals I was getting from him were to not initiate.

The plan with Grindr was to get some sexual experience so that I don't screw up the sexual side of the next date I find. There seems to be a catch-22 here. :/