Where it happened: Bestfriends house
Langauge: English
Sex: Male
Rating: 5
Category: Straight
My bestfriend was a guy, we always hung out and watched movies and stuff. I first met him when he moved into our neighborhood and his mom needed a babysitter for his little sister. We had been friends for about 4 or 5 years. He had had girlfriends and I had had boyfriends, but neither of us had ever “done the deed.”
One night while we were hanging out and watching movies we started talking about how we were kind of nervous about having sex. He said he was afraid of looking like an idiot and not knowing what to do. He said that the guy has all the pressure, because “basically the girls just have to lay there.” I told him that was bull. Bit I said that I would kinda like to know what to expect and what it felt like before it came up for me to really put up or shut up. And he agreed. We decided that since we were just friends there would really be no pressure about sex and we could try to figure the whole thing out together.
So, we decided before summer was over we would have sex. His mom was going to take his sister to a beauty pageant out of town. I said why don’t we do it one of the nights that his mom was gone, and we could be at his house by ourselves. He agreed. I went and bought some condoms and he had bought some too. I told my mom that I was going to go hang out, then went to his house. When I got there I was feeling really nervous. He let me in and asked if I wanted a Coke. I said Yes. We started watching a movie and after awhile he asked “Do you still want to do this?” and I said “Yes, if he still wanted to.”
He said well not downstairs in the living room lets go upstairs to the bedroom. First we were going to go to his moms room cuz it is a bigger bed. But I said I heard that sometimes girls bleed, and if the sheets were changed on his moms bed she might ask why. So we go to his room. And both of us sit on the bed. We talk a little bit, then we start taking off our own clothes. Except for our underwear. We decided that we should probably try making out a little because that is the way it would be with our bf or gf. He kissed me on the mouth, but it was a little awkward. But he kept kissing me on the neck and shoulders, then started to slip my bra staps down. He put his hand on my boob the stopped all of a sudden and his face was red. I asked what was wrong. “I thought you did stuff with your girlfriend. And he says her boobs are not as big as mine or as soft. THAT made be feel awkward! I just said thanks and started to kiss him. I took my bra off and then my panties. And laid back on the bed . he took off his underwear, and laid down beside me. He wasn’t even starting to get hard. So I started rubbing his penis, He asked if she should start rubbing my vagina and I just nodded. He got hard pretty quick. He got up and got a condom, it took a few tries to get one on. Then he got between my legs and I could feel his penis bumping around down there. He held my waist and kept trying to slip it in. I told him to hold it and put it in. My heart was beating so hard, I bet he could feel it. He pushed against my vagina and it barely started to go in but wouldn’t I put my hand down there and tried spreading my vagina open a little bit, while he tried to push in again. It took a few times trying then he finally pushed in a little. It hurt so bad! “I must have mad a noise because he asked “Does it hurt?” I could only nod/’ He started to pull back out. I told him don’t pull it out it too forever to get it in this far. So he pushed harder, And said, I feel something. I don’t think it will go in any more. Is it supposed to?” I kinda got a little frustrated, How am I supposed to know?! I haven’t done this before!” ‘Just push a little more.” He did and I felt something move or whatever and he got in further. I told him to be still a minute. It was hurting like crazy but I figured it could not hurt anymore then this. “Ok” I told him “start going in and out” the first time he must have pulled too far out because he came all the way out, but he got back in pretty easy. He started pumping in and out, he was watching my face and asked if it was still hurting, I nodded.
“He said want me to stop?” and I shook my head. “Try going faster.” Everytime he went it it felt like he was going to split me in two and it was hitting something up inside me, like the top of my vagina or something. He went a little faster then got a weird look on his face, and pumped a couple o more times then moaned really loud. He laid on top of me, then rolled over. When he did his penis dragged out and the condom came off, part of if was still in me. Raised up a little to look down and get the condom. He raised up too and saw all this blood. He started freaking out. Oh my god, did I rip something? Or do something?” “I don’t know, I’ve never done this before. Remember I said I read where girls sometimes bleed?” he nodded. “Do girls bleed every time or just the first time?” “I think only the first time.” I said I thought only the first time. I got up and took a shower and washed the blood off, It hurt to walk! And I hurt inside for a couple of hours after. We washed the sheets and made his bed back. We didn’t know what to do with the condom so he wrapped it up in some toilet paper then went and dropped it into the sewer drain across the street.
About 6 months later I had sex with my boyfriend and it was a completely different experience. I wasn’t as nervous and even tough my boyfriend’s penis was thicker then my best friends, it didn’t bang against anything and it didn’t hurt afterwards. But I did bleed a little bit again but not again after that.
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