![]() ![]() Related: Anal Sex 101: Why are Guys Obsessed!? It might take several sessions for him to learn to relax enough for you to penetrate him more deeply. Give him some time to adjust to the way your finger feels. Hint: Make sure your fingernails are smooth. 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. Then, try to insert your fingertip again. 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. ![]() Once he's riled up, test the waters by gently sliding just the tip of your middle finger inside. 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. If going beyond his back door is off-limits, he'll let you know. Just make sure you take it slowly so you can suss out his boundaries. Since your guy likes what you are doing so far, he may want you to explore this nerve-packed area further. For some men, the backside is strictly taboo territory for others, it's a turn-on that can intensify their pleasure.
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