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The very next day, I went out and bought my first box of non-latex condoms. Romantic and sensual. Using protection during anal sex is important to reduce your risk of catching an STI. You may have to repeat the above several times over the course of several days in order to feel comfortable with something inside of your hole. I know some guys who are good to go after one squirt. Use lots of lubricant! Once you are mentally ready, you need to get physically prepared.

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You could also try lying on your side, with your knees up close to your chest — this is often what I would suggest when using anal toys, as it makes it easier for insertion, so may help make penetration easier for you.

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This works for most guys too, although douching bulbs and enemas will not clean your ass as deeply and thoroughly as hoses and shower attachments can. NHS 'Is sex painful the first time? Some guys find that using a desensitizing lubricant for anal works best — particularly for newbies or for men who have large partners. How to kiss a guy and make out the right way.

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October 22, Reply.

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