I've always had a bit of a crush on him. Anyway, he was my ride home, because he lives just up the street from me. But instead of leaving at 1:00 when...they finished playing, we actually got caught up chatting at the bar for a while. A couple of my friends joined us, and we all ended up speaking about sex. This friend has the same attitude about it as I do- free and open about everything. I noticed his body language while we were talking seemed a bit flirtatious, but I wasn't too sure what to. So he put on the condom and got some more lube. The bed was high and he pulled my bum to the edge so he could stand and push his big cock into me. Even though he had prepared my it hurt more than any other time. I said its no good it hurts too much, its too big. He said are you sure because I am all the way in now. The pannick subsided as the pain eased and I said ok but be slow and gentle. He was very gentle and a couple of minutes later It felt great and he was fucking me while holding my. More

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