I was 12 yrs old and walking to my Dads. Parents divorced a year earlier. It was around 10 pm and actually warm for mid feb. A man stopped me as I was cutting down a back alley and asked me if I had a light. then BOOM!!! a white light and when I came to I was facedown on the snow and I seen a bit of blood on the snow. So vivid. Then I realized someone was pushing me. Then I felt the pain. I was being raped in my ass by a man. I could feel his cold hand reach under me and squeeze my balls painfully. Then he shot his cum in me and ran off into the night. I never told anyone this. Fast forward to a week ago and I'm on craigslist looking for a car and drift over to "encounters" and peruse. An add looking for a daddy draws my attention because I notice She is a he but dressed up like a girl. Cute actually. On a whim I emailed him. 2 minutes later he responds. I get that he's 15 and a tg. We make a date to meet up and the next day I'm sitting down with him at Timmies. He's nervous but stays with me. I tell him he's very cute. I offer him a ride home. In the van we sip our coffees and talk some more. He keeps flipping his hair out of his eyes. I put my coffee down and reach over and move his hair out of the way. I move over a bit and lean over to kiss him. He responds. We make out for a bit and I place his hand on my bulge. He starts rubbing as we kiss and I feel his nervousness. I unzip my jeans and he kneels down between the seats and stares up at me. Go ahead I tell him and he tentatively licks my shaft. Pretty soon he's taking half my cock in his mouth and I'm loving it. We are still in the Timmies parking lot. I run my hand under his jacket and feel his firm body. I pinch his nipples and he moans. I say lets finish this in the back and he goes willingly. We make out some more and I'm feeling his ass up. I start to push his pants down and I sit him back leaning with his hips just off the seat. I take his little cock in my mouth and start to message his bumhole. I straighten out and kiss him on the mouth and place my cock between his legs and tell him I want to fuck him. He pulls his skinny legs up by his knees and I place my cock at his asshole. I push and push. I'm his first daddy he says. Go easy. My head pops in and he hisses and squirms. I hold him still and push into him. So tight. He's sobbing and mewling and I am in him completely. He looks down between us and smiles a bit. but with tears. I lean forward and kiss him some more and then pull out a bit and drive forward. I am fucking this boy. I last maybe five minutes. I cum deep in his ass. I drive him home while he straightens out. We kiss a block from his place and he jumps out and heads home.

This is my first time with a guy too. Just so happens he's a boy.