I was 21, an age when everything is sort of do-or-die, especially regarding love. Lying on your side in the spooning position won't allow penetration that's as deep. Again, judge her reaction to decide whether or not you should proceed.
That's perfectly fine, but you absolutely should never feel forced to have anal sex with anyone. What does it feel like the first time?
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Anal sex is considered a high-risk sexual activity, so condoms will put your mind at ease and minimize the risk of transmitting any kind of infection. It's a muscle we're talking about, so you can strengthen it.
If it didn't, this wouldn't be a topic of conversation. Anal sex was something I would just never, ever do.