The first time I tried to bottom I was pure ignorant, I wanted to try , but knew nothing, I watched a few videos , it never tried , I was at a friends . I was giving him head and he ask if I have ever bottomed . I said no , I have played with a couple toys . But I have never bottomed . He said he would like to top me, when he said it I got this incredible Rush . I said okay , so he stood me up. And faced me at his desk . He bent me over , I felt his hand on my ass. And a finger touch my hole . He ran his finger around and the slowly inserted his finger, it hurt but not bad . He then stood up . Put on a condom . And used something I think it was Vaseline, And when he tried to enter . He couldn’t . I was to tight, eventually he forced the head in, and it hurt to much to continue , he took the condom off. And I sucked his dick tell he pulled out and cum in my hands . He then pushed my hands onto my hard dick and balls . And once I did that he sucked me off ,
That was years ago . He only likes getting a blow job . I go see him every once in a while , and suck his dick, and balls . The jack off .
Not a great end , but fun

I could add the first time I was trully penetrated, I was introduced to a new friend, it started with giving each other head . His dick was 7.5 but thinner then mine . One day while we were undressing , as soon as my shorts hit the floor he walked up behind me. And reach around and was playing with my dick and balls . And he whispered in my ear. Can I take you . I didn’t catch on at first., but then I said I won’t do unprotected, he said he has condoms and lube . I said I don’t know . Last line to hurt bad . He said it will hurt . I will go slow until you are okay . So I agreed,
He put on a condom , I always wanted to suck on a dick with a condom on, so I did that for a couple minutes, then her bent me over the arm of a couch , I felt the lube . And then his dick , he slowly went in , and it did hurt, but nothing like the first time . He said okay I’m all the way in . I ran my hand between my legs and reach behind me and I could feel his balls aginst me , he the pulled slowly out . This went on for a while . And I said if you want to go hard you can . And he did . And it was crazy cool , he just kept going , it seemed like 20 minutes, it wasn’t but it felt like it . He pulled out . And rolled me over and sucked me off . The third time was even better .