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I knew that this was going to be his first anal experience with a man, so it was essential not to rush things and to put him in the best conditions. So I prepared him for a long time by caressing his buttocks and complimenting him on their softness and I spread them slightly to discover his little anus which quivered when my hand ventured towards it. I heard him moan softly when my tongue came to rest there and lick him for a long time to cover him with saliva to facilitate the next step. My fingers replaced my tongue and gradually slipped into him to soften and relax his little hole which still offered some resistance. Then I told him "As soon as I feel you relaxed and ready, I will replace my fingers with my penis" I then heard him whisper weakly "Yes go ahead, I'm ready". The expression on his face mixed both desire and fear, desire for this new relationship he wanted and worry about this penetration which would certainly change the course of his life. I then placed my cock against her throbbing anus and slowly forced entry, her sphincters very slowly opened under the thrust of my glans and her complaints and moans accompanied the progression of my cock in his little tight ass of virgin...