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More From Anal Sex, Explained. The right lube is twice as important as it is when having vaginal sex, which is already super-important. You'll also probably feel like you have to anyway.

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But now that I'm someone's girlfriend, it turns out that when you really like someone, you're more willing to try things you never thought you'd try. Whatever you do, don't force it.

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Between thin water-based lubes like Astroglide and thicker ones KY , go with the thicker ones, because they don't dry out as quickly. I was afraid I would be labeled as being gay.

How do I give my guy anal pleasure?

Even if you're monogamous, a condom is probably a good idea. At least, in my minimal experience.

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A Complete Beginner's Guide to Anal Sex

All materials on this website are copyrighted. Dec 16, I also tried such a desire in my teenage years, the pleasure is great and there is nothing wrong to feel it. Make sure your fingernails are smooth. It might take several sessions for him to learn to relax enough for you to penetrate him more deeply.
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  1. When I was fifteen, I discovered that inserting a finger or two into my anus while masturbating really intensifies my orgasms and I have been enjoying this ever since.