Randy teaches me about sex

So this all starts with a sleep over at my friend Randy's house when we were about 18. Randy and I were life long friends but this night made changed it all. Now Randy and I would normally look at porn together late at night but this night we went a bit further then just looking at it.

So we are both sitting there hard ons poking thru the slit it our boxers as we were stroking away right in front of each other no cares in the world. But as we were jerking off he goes do you wonder how it feels to be with a girl. Me being a virgin and horny I said yeah. He goes ok I have an idea but I don't want you to think I'm gay.

I already get the idea of where he's going and secretly wanted him to go there but I just go ok what's your idea. He then pulls out baby oil and goes we put this in your butt crack and the other one slides his dick between the cheeks. I agree to this and we decide to flip a coin. I won the coin toss and decide to play the role of the girl first.

He lubes up my crack and slides his cock between my cheeks for a min or two and then it's my turn. To be honest this wasn't very fun it didn't feel that good. So after our failed at temp he and I decide that idea doesn't work but were both super horny so after a little replanning we decide we have to fuck the hole not the crack. I told him that seemed gay to me bye I was also super horny so I agreed to the idea.

I got to fuck him first so he laid on his stomach and I got up right behind him put baby oil on his hole and slid it inside of him. It felt amazing it was so tight and warm and nice I started going to work for a few mins before he said we have to switch. So now it's my turn to return to being the "girl" I got in the same position he did and he got up behind me and instead of using baby oil he spit on my hole and slid it in. It hurt for a few seconds but after the first few strokes I began enjoying it.

He was only about 5 inches but those 5 inches filled me so nicely. He started thrusting faster and faster until I finally felt him go as deep as he could go and then thrust in and out a few more times before I heard him say I'm going to cum do you want me to pull out? I said do guys normally pull out of their "girl"?

As soon as I said that he thrust one last time and starting shooting his load inside me. It felt so good taking his load that I began to shoot mine. Randy and I continued this on for a year or so where I learned how to take dick a bunch of new ways.