Questions for bisexual men exploring for the first time

[WilliamG]

I think OP has more issues with the fact that he didn't enjoying penetrating the other guy as much as he thought he would.
But again, it was your first time...I'm sure you were nervous or even with a lot of expectations. I don't know if your first time with a girl was great, most of the times it is not but it gets better.

Well put. I would put hooking up with a guy for the first time is like your 18-19 year old self learning about sex again. You're questioning everything. My first times with a guy was at age 64 (66 now). I really took to bottoming.

 

[WilliamG]

As a bottom, i never leave the lube to chance. If I'm going into a situation where there's any remote likelihood of needing it, I get it done first. If it doesn't then happen all I've wasted is a few squirts from the bottle. If it does ( hopefully) happen then I've avoided the pain, and being prepared makes it all much more spontaneous and enjoyable. On a practical point, I have a lube injector which gets it exactly to where it's needed.

Be prepared! You take it to another level though being already lubed. I do deep clean before I head out. I carry my fanny pack with condoms, lube, wipes, and trash bag. I find if I can just finger a good dab, then lube him a bit... I'm a happy camper. But the pre-injection plan is next level... Especially for cruising.

 

[ILoveGames48]

The thing is.. could it been a possibility or his fingering you .. you may tensed up making it tighter and more uncomfortable for you.

It doesn’t matter who I am with but the key word is trust .. if you can’t trust the guy you are with then you will tense up.. instead of relaxing and enjoying the moment

More than likely he wanted to finger your ass and be all way in massaging your prostates as he deepthroated your cock so if you cum you’d shoot it down his throat .. plus a lot of times you will cum more and that’s what he wants..

 

[jamiesux]

Give it a little time. Sadly, when done properly, it can feel incredible. What he was trying to do was wonderful (in my opinion). But he assumed you were ready for it. And of course you were not.

So now is the time to figure out what you enjoy. While he did give you a bit of a bad experience... Maybe not completely abandon the idea of anal play. You might be amazed what it feels like when done gently and with some lubrication. Maybe try some little toys on yourself to experiment? Many of us got into it this way. You control the motion and learn what you like so you can tell the guy what works. Then when you hookup again... You have the experience.

That said, there are guys that completely detest anal. And that's fine too. But I would give it a couple chances practicing on your own and then decide. I mean, a LOT of us use plugs or dildos when masturbating anyway...

I know a gay guy who does not do any anal. Full stop.

 

[WilliamG]

I know a gay guy who does not do any anal. Full stop.

Very common.

 

[niceandkinky]

I can't imagine how it would have felt for me to get anally fingered if I hadn't had very much time to explore this myself before. Even though I was used to putting stuff in there, it felt pretty weird when another person did it at first. As lots of the folks here say, it's about trust. I think so, too. In my experience, things like that tend to take time, too. And that's what makes it so nice when you've gotten used to it.
I wish you and everybody the possibility to explore your sexuality in your on time and your own ways. I think it's most fun then.

 

[csohio]

Following as a very curious mwm. Appreciate all the supportive posts.