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OK, well, my boyfriend and I went with a bunch of people down to the shore after our junior prom last year (I am now a senior, as is he). I am extremely shy and all I had ever done with him or anyone was kiss and let him go up my shirt. Jimmy (my bf) wasn’t shy he’s just extremely sweet.
Well, the first night down there, we just got drunk, curled up ,and slept next to each other. We spent the next day out on the beach and that night I was sunburned and kind of sore. Jimmy started sto rub aloe on my back at about midnight, and all of the sudden he had untied my bikini top, which really didnt bother me that much since he had been up there before. I rolled over and he poured more aloe onto my stomach, then began rubbing it onto my naked breasts, which are about a 36C.
Soon Jimmy was laying on top of me, kissing me on the mouth, neck, and breasts. He ran his fingers up and down the sides of my body until he started to pull at my bikini bottoms. Then he asked if I wanted to have sex and I said yes, surprisingly, so he stopped and put on a condom. He kissed my neck again and took his dick in his hand, slowly guiding it towards my wet pussy. I felt his thick head go in and it hurt because I am extremely tight. He pushed a little further and I started to cry. He asked me if I wanted him to stop, but even though I did I told him to keep going anyway. He held my shoulders and pushed himself into me. I remember screaming in pain because Jimmy is about 6′, 180 lbs and I am about 5’2″, 110 lbs. He is extremely muscular, and I remember him picking me up off the bed and holding me to him passionately, but it hurt so bad I blacked out until it was over. I wasn’t regretful, though, because I slept in his arms all night long. We made love one more time that night, but have not done it again since; however we are still together and don’t feel in any rush to do it again.

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