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She cried the whole time

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Age when it happend: 15
Where it happened: Lake
Langauge: English
Sex: Male
Rating: 3
Category: Straight

I had this girlfriend and we had been dating for awhile, We were both 15. We kissed and made out quit a bit but she would never let me do her. I had to guilt her into giving me a blow job, because she hated oral sex, but I loved it. There was one night that we had been to a cookout, I was really wanting to make out (or get her to go a little further) so I convinced her to take a walk with me down by the lake. I was hoping to try to get a little further then we had been. We got down to the dock and sat there with our feet in the water, and I started kissing her and putting my hands under her shirt to play with her tits. She let me do this with no problem, I kept kissing her hoping to distract her a little, I slipped one hand up her leg and under her skirt. I started rubbing her pussy with my thumb. She didn’t let on that she really liked it but she didn’t complain either. So I kept doing this, until I nudged her to lay on her back. I told her I wanted her to rub my dick so she pulled my shorts and underwear down and started rubbing my dick. Eventually I got her panties off, and kept on rubbing her slit with my thumb then just to suprise her I slipped my fingers in a little. She kinda sucks in her breath, Eventually, I am betwen her legs and keep up the fingering and kissing and sucking on her. I moved a little bit and she put her hadns on my back and I start kissing her stomach, really fast I put my face between her legs and give her a lick, she sucked in her breath and grabs my haed and says to stop. but I do it one more time, and then grab her wrists so she can’t move my head. I keep licking her.
I go back and start sucking her titties again and her neck, I am rock hard by now, and I am really wanting to stick it in, So I ask her can I stick it in, but she says no, I say only a little, and she still says no. I keep kissing her but I make sure my dick is touching her pussy, I start beggin her please just let me stick it in. just a little. She still says no, and I tell her my dick is hirting so bad, because I need to do it. then an idea comes to my head that I can make her feel guilty,. So I say I love you, don’t you love me too? she says she loves me but does not want to do it yet. Then she says, I’ll give you a hand job. but I tell her no, that is not good enough. I keep beggin her. she starts crying a little and says I do love you I just am not ready. But I keep kissing her. I slip my finger in her she was really wet, then I slip two fingers in and start rubbing them in and out of her. she was breathing really hard. So I just put the tip of my dick agaist her and just barely push in, I am thinking that she is so wet, that I’ll just slip in and she won’t know. but she sits up a little and says no stop. I pushed her back down and say I’m sorry I just want to try. I keep begging her, and she starts crying, then she says It’ll hurt. I say I’ll go slow, I just want to see what a pussy feels like on my dick. and ask if she wouldn’t want to know what if feels like to have a dick in there.
She is still crying but then gives in and says ok. I was so excited I put my dick up there and start to it in but I miss, and then I grab my dick and guide it in, she arches her back a little and pushed on my arms and says to stop that it hurts so I pull out a little, but just having the tip felt so good I need more. I put it back in. and push a little more this time, it was hard to get it in. She really starts crying now and begging me to get off of her. but I say we already did this much. So I pull out only a little then push harder the third time, and I felt my dick hit something. she is trying to turn over but I hold her shoulders down and kiss her. I whipser to her it will be alright. So she says you are hurting me. So I stop moving but I don’t pull it out. I tell her let me just stay like this for a second. She is still kind of crying, but then I starts suckig her titties again, and I say I want to push it in more, so she finally says ok and I push a little more and whatever my dick was hitting kinda moved out of the way or something because I got my whole dick in that time. I say let me keep doing it, She doesn’t say no this time she is just holding her breath and tears are still in her eyes.
It feels so good. I keep pushing in and out but I am trying to go slow, it is feeling really good and I move a little faster. Until my dick goes limp. and then I pull out of her, I say oh my god that was awesome! didn’t you like it? she says no it hurt the whole time. After that it was really hard to get her to let me even suck on her titties, I don’t want to stop at just fingering her ansymore. I always wanted to fuck her after that. And I had to always talk her into letting me stick my dick in her. We did it every weekend for about 3 months before she said it didn’t hurt anymore. She said she didn’t like it that night but I think she did.

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