Where it happened: Hawaii
My first time happened just a week ago. My parents and I went to Hawaii because it was my parents anniversary and they didnt want to leave me home. So one day I went down to the beach to sunbathe, and then a REALLY HOT GUY walked past me, smiling at me as he did so. I smiled back and couldnt stop thinking about his biceps and good looks. He must have been at least 19. The next day I saw him again, this time in the shop, when I was going to get an ice cream. He waved and winked at me, and I smiled and waved back. After I paid for my things at the till, he came over to me. He told me I was beautiful and made me blush with his comments. He then aksed me if I wanted to hang out. I was thinking SCORE! So we started hanging out for the next couple of days, till he started walking me to my Hotel Room and then after about 2 days, I asked if he’d like to come in. My parents were downstairs playing poker so I was alone in the room with him.
Then “things” led to other “things” and we were on the bed, naked and kissing. The next thing I know he caressed my nipples and rubbed his HUGE (about 9 inches, thick and strong) against my clit. Then he possitioned himself and entered. It was really sore and tight and I screamed in pain, and he put a pillow over my mouth so that nobody else would hear, all the while going in and out. I grabbed his shoulders and pushed him and he looked up and removed the pillow. I told him it really hurt and that I didnt want to do it anymore. He just said he’ll go slower and put it in slowly, but it was still painful. I told him to take it out but he said that the pain would go away if he pushed further. I didnt believe him but he still pushed in. Then I just heard a POP! sound and cried out in pain, tears in my eyes. He looked down to my vigina and smiled. “The cherry is popped” he said and I looked down. There was blood everywhere, but the pain was decreasing. He pulled out and cleaned himself, then put it in again and it actually felt great. He started picking up speed and i started humping to the rythm of his dick going in and out of my vigina. Then I wrapped my legs around his waist and moaned in pleasure as I came. After about 5 minutes he pumped harder and faster and quickly pulled out and came on my tummy. I took a shower and kissed him. Just then my parents walked in and asked me who he was, so I lied and told them he was room service. He left and I didnt see him again after that. I didnt even know his name!