I have only had oral with men, never anal. My interest in remedying that tends to wax and wane with my mood. I'm not really into guys right now but that's another aspect of my bisexuality that waxes and wanes.
I'd say that what counts as losing your virginity depends on your position. A bottom lose his at first penetration, a top loses his the first time he penetrates. For switches, I'd say it's the first time having it, regardless of position. All IMHO, though.
It hurts a little but it is far more enjoyable than it is painful. As for the virginity thing I think it is either I am a bottom so for me it was the first time I was taken by a guy
The thing that is important and worth remembering is that to really enjoy anal, you have to do it a lot. With dildos and real cock. The more you do it the more used to it it becomes. When you are fully relaxed and used to it the feeling is amazing. The sensation of a cock fucking you makes you really experience the stimulation of the inner G/spot and helmet sliding in and out. I must add that when you get to this stage you will want to do it every day, I know I do. The cock sucking is awesome too.
The thing about anal sex is its all about lubrication. If you prepare ahead of time to receive his Love all will go well. Half the guys are aware of the pain and are very tender when they give it. Eventually though, the pain goes away and its sexy and beautiful. Wonderful question.
Answer as soon as bottoms, filled with you cherry gone.
Good luck push deep ky lube.
Starting to experiment with anal is mainly about patience. And lube! If you desire to receive anal sex, remember, you don't have to take him in the first time. You should begin with having your partner "play". Perhaps rimming, get used to the feel. After a good rim, let him put a well lubed finger in, slowly. Do this a few times over several days. Then move on to a small butt plug. Always insert after being fingered, and ALWAYS use a lot of anal lube! Let the finger go in, maybe let him stretch a little. Move to the plug, let it stay in a bit. Eventually try to let it stay in long enough to get a good blow job while it's in. Get as horny as you can with it in. Before taking the dick, you may want to move to a slightly bigger putt plug. Let this process play out over several weeks. Every time you have sex, include butt play. If at any time you don't like it, you can end it and only proceed at your own terms, if at all. Even with all this prep, there's nothing like the first actual fuck. May want to get a bit boozy for that!
My first time it hurt a little but the pain gave way to pleasure