She said ok but do it carefully. We didn’t know how it is done properly.Then we saw some pics in that book and tried similar positions. It was not g...ing properly, tiny hole etc. Then finally I applied some force and made it enter.She started pushing me out and saying, Bhaiya, ruko, bahot dard ho raha hai etc. She was almost into cries. I stopped and came out. She got blood. We both got worried. We thought we did something wrong and now some problem in the vagina. Then I helped her to clean her. Please feel free to contribute, thanks!)********I turned eighteen a month into my senior year of high school. Skinny, shy, good at math; I was last pick for the basketball team and last pick for the opposite sex. But by Christmas, I had gone from being terrified of girls to living the cliché as the official “sexually non-threatening platonic guy friend” of the five hottest chicks in school.As nice as it was to have popular friends and beautiful women to look at all day long, I was also. Shortly after I returned home, I had contacted Joanne and explained what happened. Just my luck, I had a chance to meet this incredible woman and I blew it over a silly dream of cycling across the continent. I got myself a job for six months, until I had enough money to go again, this time on the Greyhound. It might seem funny for a guy who works in aerospace, but I don’t like planes. March of 2005 found me living in Florida. It didn’t take me long to start chatting with Joanne again. By this. Me: Mmmmm.Chloe: Mmmmmm. I feel like I want more.Me: Me too!I decided to heat things.Me: Can I take your shirt off?Chloe: Hmmm. Let me think.I did not let her think muchMe: I’ll take that as a yes.Chloe: Hahaha. Good.I lifted her t-shirt. She opened her hands to let me remove her t-shirt smoothly. Her upper body was fully naked now. She crushed those squishy boobs into my chest. Now she was sitting on my lap with her legs curled behind my back tightly. You can search for ‘Gemini’ pose on.