First time was with a hung trans escort

>be 19, fresh out of high school
>making good money roofing for the summer before going to college
>guy on roofing crew keeps bragging about fucking whores he found on Backpage
>take a look myself, end up looking at trans escorts
>end up contacting one that catches my eye, claims to be 9in...top only
>explain to her how i was a virgin and very nervous, she tells me everything I need to know about bottoming
>go to her condo
>immediately she puts me on my knees and lifts her dress
>timidly start sucking her cock
>it keeps getting bigger and bigger, having trouble getting much more than the head in my mouth
>tells me it's time to loose my card
>takes me by hand to bedroom, strips me naked and has my lay down on my stomach
>starts licking my asshole, hear bottle of lube opening
>feel the cold on my ass, start to feel the head of her dick probing my hole
>head pops in and it hurts
>slowly slides in balls deep and starts fucking me
>gradually picks up pace for what felt like an eternity, now ruthlessly being fucked
>pain gave way to pleasure
>moaning like a bitch in heat
>flips me over to missionary
>looks me in the eyes as she tells me she's going to cum
>proceeds to blow a massive load deep into my ass

I went back several times that summer, sessions kept getting longer and longer. She really enjoyed using me as her fuck doll.