Pleasuring the anus

To begin, put a generous amount of water-based lube on one or two fingertips make sure you replenish the lube often and gently massage the area around the outer rim. Once he's riled up, test the waters by gently sliding just the tip of your middle finger inside. If he clenches his sphincter muscles, which encircle the anal opening, pull your finger out and continue rubbing the outer area to help reduce his tension. Then, try to insert your fingertip again. If he likes how this feels and is up for trying more anal action, gradually move your finger in deeper, taking care not to scratch the delicate tissue inside.
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How do I give my guy anal pleasure?

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20 Anal Sex Tips for Beginners - Hot Tips for Anal Foreplay, Fingering, and Sex

Hi Guys! Try these anal fingering techniques to warm her up for anal sex and give her very pleasurable anal orgasms! Ladies click here. It is also a great way for you to give her very pleasurable anal orgasms. Actually, you should attempt to give her an anal orgasm with your finger first before attempting to use your penis. This will give her a great introduction to anal pleasure as well as prepare her for your penis. The reason why you can give her amazing orgasms through anal fingering is because with your fingers you will be able to stimulate indirectly her G-Spot and maybe even the back of her deep spot!
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So You Want to Try Anal Sex

Anal masturbation is an erotic stimulation focusing on the anus and rectum. For humans, common methods of anal masturbation include manual stimulation of the anal opening, and the insertion of an object or objects such as fingers, tongue, phallic-shaped items, water play, or sex toys such as anal beads , butt plugs , dildos , vibrators , or specially designed prostate massagers. Pleasure can be derived from anal masturbation due to the nerve endings in the anal and rectal areas.
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Learning how to anally finger your girl properly can be one of the most rewarding things you embark on. With anal fingering, you can actually give a girl anal orgasms which we will mention later , as well as even stimulate her G-spot — this is because the anus and vagina are actually only separated by a thin membrane, which allows sensations from one hole to be felt in the other. Anal fingering stimulates a girl mentally and emotionally. That being said, there are a few unique differences that you need to keep in mind when first doing this.
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