8 years ago I answered an ad on Craig’s list . He said come to my office and we can talk . I drive by at least three times before I built up the nerve to go in. He was there alone , he said let go into an office. We walked in and sat down , we made small talk , then he asked if he could see my dick, I sat there for a second , stood up , took off my shoes, shorts and underwear . And sat back down . He took his off , he walked up to me , and I bent over a little and took him in my mouth . He was perfect . I sucked him Untell he was ready to cum, and shot in my hand . About once a week I would go see him , about the fourth time, he asked if I’ve ever bottomed , I said no, but I have had a couple toys . He said he wanted to try , he said he has lube , I said okay , so he put me over an examining bed, and started by touch me , his hands were on my ass, one slide under and cupped my balls , and then I felt it , a little pressure . It was starting to hurt , he kept pushing . And then stopped . All he got was just his head . He used more, and then tried again , this time he went head deep and it wasn’t as bad . And he kept popping his dick out, then replacing it . And in doing that he went a little deeper , it started hurting again , but instead of stopping. He went balls deep , it hurt so freaking bad . I tried to get up but he held me there and then slowly pulls half way out and back in, a couple times of that and it was easing up , when I thought it was going okay is when he pulled all the way out and slammed back in . The pain came back for a second , he didn’t stop this time . He kept pulling almost all the way out, and slam back in , Untell he was close , he pulled out and stepped back . I just kinda slithered. To the floor . I look up and he is pulling the condom off and stepping up to me, I took him in my mouth, he didn’t last long before he started cuming . When he pulled out, I spit what he gave on a towel . I want to bottom bare to completion some day .