Try massaging his lower back just above the cleft, then circle round, using scented lube-oil to his perineum ( the ridge between his balls and his arsehole ). Caress this up and down lightly, then spiral slowly in towards and round his arsehole. DO NOT HURRY. Let him suck one of your forefingers as you do so. The press the knuckle of your bent thumb into the hollow of his back-passage. Do it SOFTLY but in a slow Regular Rhythm. If you combine this with pressure on his Perineum with the fingers of your free hand, he will beg for more. No words are needed to get him going this way ! His body movements will tell you how much further he wants you to go ! This method has worked well for me on a number of occasions, BUT Remember while he may enjoy all of this, it may not mean he wants finger penetration. A lot of men enjoy the sensation of pressure against the Ring-muscle, but only that.
It might be worth your trying to talk him into giving you exactly that sort of massage, by telling him that you will demonstrate on him. 20 cnets to a dollar he will want to go on to fuck your arsehole, which will entitle you ( well, sort of ) to do the same sort of thing to him later !
Have fun
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Bella
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