We made out for 2-3 hours, with his friends walking in and out of the room (though we couldn't care less). Finally, we got over it and he didn't asked to continue (probably because he wanted to leave a good first-impression on me). We left our night as is, he kissed me goodbye.
The next day, I actually had to move out of the residence because I found an apartment nearby with a roommate. He helped me moved for a bit, and he wrote me a very sweet poem. It completely melted my heart.
At that time, Andy was having problems with his own housemates, so he ended up staying at Will, my novelist ex-neighbour's place a lot. I ended up going back to visit them everyday.
On the same week, that weekend, it was a long weekend and Will was going home 3 hours away from the city. He planned to be away all weekend.
I continued to visit Andy that day Will left for home and I brought him breakfast. We spent the day together, and we ended up making out on Will's bed. He was honestly such a good kisser. While we were kissing, he was on top of me and I could feel his penis already hard pressing against me.
Right then, he started fondling my boobs. He told me how he loved my mole on my left boob and how sexy it was. It was honestly feeling quite good, and his fingers traveled lower and reached my pants. He unbutton my pants and reached in, and slowly rubbing my clit. I could feel that I was already really wet.
I did mentioned that I was a virgin, but I had received oral sex from my ex bfs a few times before, so I wasn't particularly holding back. Plus it was feeling really good that I couldn't tell him to stop.
He asked me if he could take of my shirt, and I nodded. He started kissing me on my boobs, while he rub my clit, then he slid a finger into me and started rubbing me inside my pussy as he lick and suck on my nipples. I had honestly never felt so good before and I could not stop him at that point.
He started kissing lower until he reached my pussy, and started licking me around while he rubs me inside with two fingers. I'd never felt such strong pleasure before and I just spread my legs for him to lick me on my clit while fingering me. I was breathing so hard and fast.
Right then, he asked if he could put his penis in. At that point, I was so blinded with pleasure that I could not reject him. He took out his 8 inch penis and tried to push it in. I had honestly never seen a penis that big before and it did scared me. He actually could not get it inside me because I was so tight, and I felt this sharp pain as he tried to push inside me.
I started tearing and I told him to stop. He actually had no clue that I was a virgin, so he asked the very obvious question at that point if I was a virgin, and I nodded.
He said we could stop, but I told him I wanted to continue. He gave me a very soft, gentle kiss on the lips and then tried to put his penis at the opening while he pushed in. I was in so much pain that I dug my nails so deep into his back.
He asked if I was OK. At that point, I had tears running down my eyes, but I nodded. He started moving slowly inside me and it was hurting me so much, but I bear with the pain. Fortunately, he had not had sex for a few weeks and it only took him 1-2 minutes to cum. And he pulled it out and shoot it on me.
It only occurred to me afterward that we weren't having protected sex (i did go see a doctor the next day for birth control, and after that, he did become my boyfriend and we did have thousand more times of sex...
