Yea as a young twink all the older guys wanted to fuck my ass and first times were not that pleasant. With time and experience though it will come and feel so natural. I do recommend an anal enema to clean things out and make room for his meat and load.
I also think using a butt plug or dildo will open you up and esp the sphinter muscle which is probably still tight.
At first you should use lube and dont be afraid to sit on top of him and direct his cock into your hole slowly. Once the mushroom head gets in then slowly sit down and the rest will push in easily. Kissing and fondling are important at that moment and then start moving your bodies together in sync. Tell him how you feel and let yourself go. He'll be back for sure
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