I've never shared this story with anyone, but I've never been so horny in my entire life since I created an account here reading all the hot stories, so felt it's a good time to share. True story here, this happened to me when I was very young.
At the time I barely knew how sex worked, never had a real bf, and had just sucked and been fucked maybe a couple times. I grew up in a different country so there was a sort of craigslist equivalent there. One day I posted an ad saying that I was "looking for a bf" (yeah, right), and got tons of replies. But one in particular stood out. It was an older guy, I forget his age but probably in his 50ies so almost 3x my age. He said he was looking for a young boyish twink and wanted to take me to a hotel and make love to me like a woman and that he would pay me for it if I let him do what he wants.
First I was offended and frankly disgusted and didn't even reply. But I kept thinking about it for some reason. Something about the thought of being treated like a woman as he said turned me on a lot. And also the idea of having another man paying me to be able to use me as he wants was very sexy to me, while still feeling it was degrading. After a week or 2 of thinking about it constantly, I decided it was time to give it a try and replied.
The man replied almost instantly, saying I made the right choice and that he would take good care of me. We chatted a bit and convened to meet on a following Friday where he would pick me up not far from my place after I was done with school, take me to the hotel to spend the night, and drop me back at my place the next day. We didn't really discuss much what we were going to do, even though I asked multiple times, but he just said I had to be obedient and do what he says.
I was SO nervous on the day he picked me up. I'm already very shy by nature, so you can imagine I was a nervous wreck going in a complete stranger's car and being his "woman" for the night. When I got in he was literally devouring me with his eyes. Said he was glad I was very twinky as he likes his boys looking innocent. The drive to the hotel felt like forever, but I don't think it was more than a 20-30 mins drive. It was way out of town near a highway, and I was very nervous arriving there and almost backed out. He probably saw I was nervous because he told me not to worry, that he'd be gentle and I'd have a good time, and that helped me relax a little.
Once inside he wasted no time and as soon as the door closed he started kissing me passionately. I had never kissed a man at the time so it felt really weird. He was very forceful about it too. Then he removed my shirt, and told me to kneel in front of him. I had an instant of hesitation and he told me to hurry up, and I obliged. He was still dressed then, and didn't even bother undressing, and just unuzipped and pulled out his cock and told me to kiss it and smell it and tell him how beautiful it is. Now I was not a total stranger to cock at the time as I had blown I think 2 guys and been fucked twice too, but it had always been after long makeout sessions with lots of cuddling and sweet words and all that. So finding myself like this on my knees with a stranger's cock in front of me felt really uncomfortable. I probably managed to lick and usher a few words uncomfortably about his cock, and I like the he kept ruffling my hair and gently rubbing his hands over my face. I felt very vulnerable and liked the attention he was giving me while I made his cock go from limp to hard.
When he got fully hard though his attitude changed. What was once gentle ruffling of my blond hair became fists who grabbed my hair and held my head in place. He told me to open my mouth, and didn't even ask me to suck him - instead he pushed his cock all the way down my throat while keeping my head still. I was pretty shocked then, had never had a cock in my throat before. I was gagging a lot and asked me to stop, but he told me if I want to satisfy him and serve like a woman I have to get used to it and that I should stop complaining. Still in shock, I did my best but probably wasn't very good at it, although I remember him saying he liked to hear me gag.
After a while he probably got bored or likely there was too much teeth, and he told me it was time to make a real woman out of me. He put me back on my feet and went back to kissing me intensely, but this time one of his hands started playing with my hole and he started fingering me roughly. It hurt and he wasn't gentle about it, but we stayed like this for a while and my hole started loosening after a while.
He put me on the bed on my back, lifted my legs and started approaching me with his erect cock getting clearly ready to enter me. This is when I started fighting back and telling him I didn't want to get fucked without a condom. He was actually very nice about it, stopped for a minute, told me he just fucks his wife and he's only been with very few twinks, and that I had nothing to be worried about. I was still hesitant, but figured I could trust him, so I went back in position. He entered me slowly while caressing my chest. He clearly had no interest in my cock, but he pinched my nipples hard while entering me. It didn't hurt so bad because he had fingered me well before, but felt very different to the couple times I had been fucked with a condom.
He started fucking me harder and harder, telling me sweet words, caressing me gently, I really felt like a woman that time. His constant pinching of my nipples, and the feeling of his raw cock going inside and outside of me made me shoot my load very quick all over myself. He lasted a few minutes after that, and he had a deep groan and said things along the lines that I was now his boy and that my ass was his. Then he collapsed on me and passionately kissed me for a while before we fell asleep.
He fucked me 3 other times that night, as I found myself woken up by his raw cock entering me and I just took it. Come morning after a last fuck he told me it was great and that he would love to see me regularly. He insisted on paying me for this, saying that I had been very obedient and I deserved it. Took me back to my place, and not an hour later messaged me to see if I was available the very next Friday for the same thing. I ended up seeing him for several months almost every week. He brought me gifts sometimes like pieces of underwear or t-shirts that made me look cute, and he was always paying me for it. Inside my head I was turned on by the idea of giving up my ass raw in exchange of that, even if that felt wrong.
After a few months I moved to a bigger town for college so we couldn't meet anymore. He emails me a few times asking how things were going and if I was coming back for the holidays, but we kinda lost contact after a bit. He's the first I've let fuck me bareback, and the only one I've let do that before a loooong time. I was thinking about these memories fondly as I just had my first anon cumdump scene last weekend, and I think it was a great introduction for me to bareback sex. I regret nothing, except the fact that it took me many years after this to accept going back to bareback.
This was a bit of a longer post than I anticipated, but I hope you'll find it interesting as this is the story the way I remember it. I've actually never told this story to anyone, there's a bit of a stigma with it being first bareback and then being paid for it, so I've kept it to myself, but this felt like a good place to share it for the first time.