Ask GayDemon: Anal Virgin

I’m nervous about my first time with a guy. I decided recently that I am only attracted to men, not women. Will it hurt? I don’t want to ruin my hole. Is there a way to make it more pleasurable?
-Hole in One

"Ruin my hole"? Such language! Do you fuck guys with that dirty mouth?

It will totally hurt and your hole will be utterly destroyed forever. All the professional seamstresses in the world will not be able to put you back together. You'll be like a discarded stuffed animal in the bargain bin of a thrift store whose hole is blown out.

And all that damage just from kissing. Imagine if you get fucked.

Dream it and be it. If you have this horrible stereotype that receptive anal sex is painful, then you wouldn't conceive of doing anything to prepare for the situation and it will most likely hurt to some degree. Which is different than it causing physical damage. You do need to separate the idea of being gay from anal, in that everyone has an asshole and people of all orientations and genders may get into anal sex. You can get the classic book Anal Pleasure & Health by Jack Morin.

Or the classic gay movie Anal Pleasure & Destruction and jack off to it. Way less reading.

Porn flicks generally don't show the preparation portion, though sometimes show elements of it, like massage, kissing (yes getting excited and wanting it matter to the situation), positioning, lubrication, taking breaks. You don't need to perform for someone. You just need to be you, with honest desire (or not so say no), relaxation, arousal, fun, all that. You may choose to only have anal sex with someone you're in a relationship with and keep casual sex to oral or other. But even if you have casual anal sex, that requires a partner who is a solid communicator, flexible, adaptable and patient.

Say he ha a position he prefers as a top but it doesn't feel comfortable for you. Maybe he wants take you from behind, but you need eye contact. If he can't adapt to your needs without sacrificing his own (or vice versa), then you two are not compatible. It might feel better for you to be on top to start and if he's not into that, then his loss. There are plenty of other dicks in the sea (of dicks).

Do know that enemas are not required (and in fact can cause imbalances in your system). Try asking folks about their experiences. And that includes the guy you're with, who may also have been on the receiving end. You may want to try topping as well.

Overall, you don't need to fit into some role, and don't need to associate being with a man (anally or otherwise) with being somehow ruined.

I also suggest incorporating anal play into your masturbation, which may include toys or just your hand. Just practice good hygiene with everything, including proper care of toys (which a good sex toy shop can tell you all about).

You may then want to show off fucking yourself to a guy, and that can inform how you like to take it. You're in control at all times, can slow down or say no at any time, even after saying yes, even moaning yes. It's your body, your choices, your desires, and nothing needs to be ruined.

Though you may find some dirty talk of "Ruin my hole!" hits the spot.

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