I could never ever tell anyone this. Hence the reason I am here. This is a very true story of an off the wall idea I had. First, about me. I am coming up on 20 now but I was 17 at this time. I am a white Male, slim and about 130 pounds. I had never experienced anal. Fingers, toys, nothing. I had heard from here and there about anal orgasms from guys and girls over the web and for some reason, after some drinking, I decided I wanted to secretly try it. But how? Craigslist. I posted an ad saying I was 18 wanting an anal experience. I got a lot of replies and finally I randomly picked a few. Everyone, and I mean EVERY guy, backed out bc of some reason or another. Only one person said he would meet me. I had already told him who was there and where I was so he says, "I will even drive there to prove it but if u say u will let me I want to do it." I was very hesitant. This is my first time and the only person who says he will come is an hour away and he is a huge cock black guy. I kept on talking to others and every min or two he would pop up insisting he come. I said okay but we had to meet behind the house bc people were there, which was a lie. He said that was okay. As he was coming, I gave him my cell # to text. We both had an agreement. He was going to park a little ways down and go behind the house. I’d meet him there. Cool. HE wanted me to undress or already be naked and already lived up and I said fine. 30 mins or so go by and no text. I’m thinking he isn’t coming. Relief. Then I see lights pass and I get a message. "I will be back there." I am freaked. I took my clothes off so slowly and was already nervous. "I’m here and waiting. Come out." I nervously replied and tried to meet some agreement…."okay um, gimme a minute trying to just get naked and come out quietly." Another partial lie. He said "good u will already be naked? I’m already hard" That is when I had to say something. I tried to get out with some kind of agreement. "Yea and u came a long way for me but really would it be okay if I came out naked and let u maybe touch my ass and stuff? We can maybe talk about it and I will still be lubed let u in me. I jus be sure u like what u see." He said okay! I pulled the sliding door open and crept slowly back and there he was. Completely naked like me and hr had a huge thick boner pointing straight at me. All I did was turn a d put my hands on the wall and I couldn’t say anything. I just couldn’t. A felt a hand slap my ass kind of hard and fingers rub my slick butthole. I wanted to say I guess u like me but lets talk a little about this. Maybe get out of it but no. All I choked out was "Ok so do you like it?" I felt a hand on my left hip pull and bend me down and the other hand pushed and straightened my back out and I didn’t see but could feel feet mounting the ground firmly right behind me and I I felt dick press against my ass and he said yes! I do! And the other hand grabbed my right hip and pulled and his dick went in about 2 inches or so and it felt so deep and painful. He pushed in and all I did was clench and push thinking he may slip out but one more push and he was like "okay halfway." Then he pushed hard and was in me 9.5 inches. My butthole was stretched over him and he stayed in me for a second and I was like, "oh my God I can’t do this." And he said ",You are doing it fine." And that is when he started really fucking me. He’d pull out to about right under the head and push back in at a hard, steady pace and all I am doing is staying limp, supported by his hands holding my waist, getting fucked in the ass by thick black dick. For at least 45 minutes it was "Ugh…ouch…oh god….umm..umm….umm…oh…umm..ugh…"
So painful. I finally put my hand on him to maybe slow it down or anything I could do. I asked, "okay! Are u gonna cum!? Ugh! Umm! Ouch! Are u cumming!!?? Umm…ugh…" He just kept on. What had to be like 15 minutes of no answer and pushing on him I finally gave up. Limp. Legs quivering and I said, "Fine just fuck me…" This steady, nonstop "okay! Ouch! ….ugh, umm…." fucking me lasted for another hour. He said he wanted to cum in me and I was like please! Please do! He trusted hard, very hard, into me and came in me. Finally. He pulled out and I turned around. He stood there, still hard and said thanks but are u done? Can I have maybe 10 more minutes? My swollen, painful, now full of cum butthole made me go to my knees without even thinking and inleaned forward and he already knew what to do. Mouth open, he put his cock in my throat and bobbed me back and forth for only a short bit until I felt his cock throb in my throat. He pulled out and let out a breath and said "wow thank you!" After that….he just grabbed his clothes and walked away. I wobbled into my house and went to the bathroom. I sat on the tub edge and felt cum dripping out of me. I got up and bent in front of the mirror a little and my ass was swollen, purple and cum coming out of me. I cleaned up and finally went to bed.
It was literally sore to sit for days. I had just been butt fucked for 2 or 3 hours, I deep throated black cock and I felt like I’d try it again after I was feeling better.

Maybe…round 2??