This was a few years ago when I was in my early/mid 20s. I'd had a breakup earlier that year, and was desperately horny. I'd gotten into the habit of sometimes anonymously sharing nudes with strangers online - particularly grindr. I'd talked to a lot of guys who wanted to fuck me, use me, some even said they would rape me (I have a rape kink but never experienced anything non consensual). 

At this time I'd been on T for quite a while and had top surgery. I was quite slim, hairy, with a flat chest, beard/stubble, longish hair, and a shaved pussy. It turned me on a lot to share pics of my body with strangers who would tell me what they'd do to me. I almost never shared selfies because I never really had intentions to meet up with any of these guys though and often deleted the app, only to do it all over again.

There was one profile that always caught my attention on the grid. His name on there just described his cock: thick 9 inch. He essentially had a blank profile though, no pictures of himself on there. I sometimes had my selfie up, sometimes didn't. I one day decided to start talking to him and we shared nudes. His cock was pretty big. I was still incredibly nervous, but part of me did want to meet up with him because I'd not had much experience with hung guys. We'd also sent face pics to each other.

I got cold feet and ghosted him until my curiosity got the better of me probably less than a week later. We agreed he would pick me up in his van, take me to his place, and he would fuck me. 

It was maybe 30 minutes later, after I'd showered, that he was pulling up near where I lived and I got in the passenger seat of his van. I was so nervous. And honestly it was really awkward, but I was turned on. I kept having thoughts about asking him to just take me home, I'd changed my mind, but I didn't say anything. I asked him something inane about the size of his cock but other than that the drive was quiet and tense and awkward. 

We got to his place and he invites me in. I have a drink because I am so nervous. This entire time we haven't even spoken about protection although I did bring some condoms with me, in my coat pocket. We go upstairs to his room (I think it was a shared house, he was in his 40s and had a small room with a single bed) and I take my coat off, lay it on his desk, and he starts to get undressed then undressed me.

I'm so nervous. He starts to kiss me but I don't really want to be kissed so turn away. Which is a bit stupid considering mere minutes later we are both naked, and I'm sat on his bed while he stands next to me and I suck his huge brown cock. It was very big indeed. I'm only sucking it for a couple of minutes before he pushes me onto my back on his bed and he starts to eat my pussy. This too only lasts a couple of minutes. In my head I'm thinking about the unmentioned condoms that are still in my coat pocket. I want to say something but I don't, and he's on top of me now and lining up his big raw cock with my pussy. 

He slides it in and starts fucking me completely raw. It hurts a bit at first. The entire time he's trying to kiss me and honestly I'm not really enjoying it, turning my head away. I'm starting to moan, and hoping he isn't going to cum inside me, but I don't say anything. Internally I'm panicking but then it starts to feel good. But it really only lasts maybe four minutes before he tells me he's going to cum, and he asks me where do I want it. In a panic I tell him to cum on me, cum on me. He pulls out and cums on my pussy. 

I am completely underwhelmed. I ask if we can go again and he says he is done (lol). He drops me back off home and asks if I enjoyed it and I lie and say yes. It was honestly the most pitiful sex I have ever had. I felt used. Regardless, I was stupid and so we continued to talk on grindr. He told me he wanted to own my pussy. And that next time, he was going to cum in my pussy. 

I eventually came to my senses, deleted the app and never spoke to him again. 

I'm still on grindr every now and then and sometimes I see his profile. I fantasise a lot about sex with strangers, but I've never done anything like that since. But I still look back on it and it makes me wet knowing I took a stranger's big cock inside my little pussy, totally raw, and I didn't even know his name, and really he could have cum deep inside of me if he had been less considerate. He basically just used my pussy to get off.

I don't know if that is tragic, or hot, or both.