This was the beginning of the year and I want to say upfront that I was very sheltered growing up, inexperienced in a way that's hard to explain if you didn't grow up the way I did, and my brother's friends coming over to hang out and play games and sometimes sleep over felt completely normal and safe to me because that's just how it always was and I never thought about any of them that way even though I noticed that some of them were attractive and one of them in particular was cute in a way I tried not to think about too much.
That one ended up alone with me in my room at the start of the year when everyone else went out for food and we stayed back because neither of us felt like going.
We were just talking at first and then he asked what I had and hadn't done and I told him the truth which was not much, basically nothing, and he said he could help me figure out what I liked if I wanted and I looked at him for a second and said okay and what I meant was talk me through it and what he understood was something else entirely.
He moved to sit beside me on my bed and got his hand under my shirt before I had fully processed that we were doing this and I felt his hand on my tit, his palm flat at first and then his fingers finding my nipple and squeezing and I made a sound I did not plan on making and he took that as the confirmation it was and his mouth found my neck and started sucking there and I had never had anyone's mouth on my neck before and the feeling went straight down through my chest and between my thighs before he'd even gone anywhere near there and then he pressed his leg between mine and started moving his thigh slowly against my pussy through my jeans and I was already embarrassingly wet and he hadn't properly touched me yet and I could feel how wet I was through the denim and that made me even more embarrassed and even more turned on at the same time.
He asked if he could touch me and I said yes and he got my jeans open and his hand inside and his fingers slid through my pussy and found how soaked I already was and he held his fingers up so I could see them glistening and I wanted to disappear from embarrassment but also absolutely did not want him to stop, and he slid his hand back in and started working his fingers through me slowly and when he pushed one finger inside and felt how tight I was he said FUCK quietly under his breath and looked at me and started moving it slowly and I grabbed his arm with both hands and just gripped it and my hips were moving without me telling them to and I was so close already, SO close, from one finger and someone's thigh against me through jeans, which tells you everything about how inexperienced I was.
That's when he asked if he could try just the tip and I knew what that meant and I knew where it was going and I said yes anyway because I was too far gone to make careful decisions and I felt him move between my legs and then I felt the head of his cock right at the entrance of my pussy and the pressure of it there before anything had even happened was already making my brain short circuit and he started pushing in, just the tip, just the head, and I felt myself being opened up for the first time in my life and it was uncomfortable and overwhelming and so much more than I expected and I said oh god and grabbed his shoulders and he held still with just the head inside me and I could feel my pussy clenching around just that much of him and he groaned and said you're SO fucking tight and asked if he could get a little more in and I said yes, just a little, and he pushed further in and I felt more of his cock filling me and my legs were shaking and he held still again and asked if he could just fuck me and I looked up at him and could feel him there inside me and I thought about saying no and didn't and said yes instead.
He started moving and the feeling of his cock sliding in and out of me for the first time was something I had NO frame of reference for whatsoever, nothing I had heard or read had prepared me for what that actually felt like, and I was making sounds I had never made before and couldn't stop making them and he was going harder and deeper and I came before I even understood it was going to happen, suddenly and completely, clenching around his cock, and he followed right after, his whole body tensing over mine and staying still.
I've been thinking about it since January and haven't really stopped.