i almost envy you, the first time is so arousing, just be sure to pay 1 hour to the shemale so she can open you up slowly and also cum all over you, also be sure to kiss and suck her cock for a while while masturbating yourself, rub her penis all over your face you'll love it... use poppers or weed so the pain is not overwhelming, and also be sure to be very very clean so you don't have to worry about accidents
your journey will make you very happy but be careful, shemale penis is the most addictive drug there is, you'll end up horny 24 hours a day and your ass tickling all the time will dominate your whole sexuality