This wasn't the first time my girlfriend had tried to stick a finger up my butt, and it wouldn't be the last. I breathed. I'm a bisexual man, and I had bottomed once before with a man. We'd been dating for months at the time, and he was typically the bottom, but since I really liked him, I thought I'd return the favor. It was an all-around mediocre experience: I was too drunk, it hurt, I thought I had to pee, and I kept asking if I was pooping on him. He finally snapped, "Zach, if you shit, you shit. Shit happens. Even though I was typically a top, men I'd dated had always asked me — actually more like begged me — to bottom. After that one not-great experience, I always declined. I had too many fears, pain being the main one.
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1. I'm pretty sure the butt wasn't made to be penetrated. Is anal sex bad for you?
Use lube. You have no idea how sexy male moans are. Start out by using a finger. Go slow. You have to remember that. Use your hands or a sex toy to play with them, so that she has the opportunity to get off, too. Foreplay still matters. You still have to put in effort. You still have to seduce her. Squeeze her ass.
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Despite increasing pop culture coverage, anal sex is still heavily stigmatized. While this might be true for some women, assuming it goes for all women is completely unfair. Woman A: It honestly does hurt, be prepared, and use lots of lube if you want an easier time. Woman B: At times, it can be uncomfortable, but I don't recall that it ever really hurt. I've had partners who are very attentive and listen to my needs, so I've never experienced pain. There are times, however, when a larger penis may cause cramping. Woman C: For me, it did. That first time was like, "Oh dear god, nothing is supposed to go in there. Like a lot of deep breathing and you have to let everything go.
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