OMG ! This reminded me when i was fucked for the very first time, it hurt but a nice hurt and when i got used to a cock in my tight ass i wanted it all the time...
My first time was with a tutor that had spanked me for not doing my homework. After the spanking when I stood up and had a raging boner, he took that as his que to teach me to be a gay boy. First it was sucking him, then he put me on the table with a pillow and used some lube and fingers. Then he entered me so so gently. Let me grow accustomed to him. It was such an awesome experience but when he came inside me I came hands free. First times are always the best if done right, and he did.