Well, this one is difficult to answer without going into details about past partners that are beyond what I’m willing to disclose. There’s specific stories involved, including personal details about their bodies and lives; those aren’t mine to give away.

That being said, I’m not a fan of anal. In my youth, I tried it a good bit because there was this idea that anal didn’t count as losing virginity. Then, years later, it would be the occasional thing where a new-ish partner would offer out in a way I wasn’t willing to decline. This was before I learned that it was okay to turn down offers like that.

Some women will indicate that anal can/should happen because they think that every man wants to do it, and either want to meet that standard, or want to give their partner something special. That second one is where I initially felt conflicted about turning it down.

So, back then, I would usually just not orgasm/ejaculate. I almost always used condoms anyway, so it wasn’t like it was obvious if I did or not.

It wasn’t until much later that I ran into someone that genuinely enjoyed anal for their own sake. And that makes a difference in how it feels, as well as the overall experience. When the woman is eager for it, enjoys the entire process, and wants another go at it after you recover, it becomes much more enjoyable. A partner that orgasms from anal is just different than someone that’s just taking it in the ass because they think they should.

Everything changes. Their movements, the sounds they make, how they approach leading into anal. If someone is into it, even the sensations of that first thrust change compared to someone that’s okay with it, but not into it for its own sake.

Now, I can’t say I’ve grown to love it. It’s still at the bottom (heh) of my list of places to put my penis. But when a partner is into it, I enjoy it and can reach orgasm as well. Which, enjoyment and reaching orgasm aren’t inherently tied together, as a tangent.

I started giving instead of receiving

I’ve always enjoyed giving. I’ve been lucky enough to have a few partners who really love it

More recently I’ve been experimenting with receiving

I’ve enjoyed being rimmed, but until relatively recently I hadn’t ever received anything penetrative

I jumped in the deep end a little while ago and my fiancée fisted me. It was fairly successful for a first attempt!

I’ve experimented solo a bit, as the videos I post show, but it’s still not something that really lights my fire. I have to be in a specific mindset and mood to enjoy it

I wanted to try something new so I bought a small dragon dildo from Bad Dragon. It was rough at first, mostly painful. It did give a new experience though as it felt like an orgasm lasted a bit longer when masturbating. Still haven’t come from just the dildo though, it’s just an addiction. I don’t use it all the time, just when I want something a bit more intense.