My actual first attempt was raw.. My friend and I were 15 and had been sucking each other for a couple of years, we only made each other cum once with oral though.. we had always attempted to sit on each others cocks but never actually penetrated. one night at his parents place (they were out) I was sitting on one of the recliners when he came over and pulled my cock out and started to suck it. I was so horny I was getting ready to actually cum when he pulled off.. I told him I was to close to cumming, but he pulled out some vaseline and said he wanted me to fuck him.. he got on all fours in front of me so I did the natural thing and lubed up his hole and my cock. I then started to push it in and could not get it to go. I had never fucked anyone to this point girl or guy so I really did not know what I was doing, I grabbed his his and pushed really hard and my cock went right in.. he immediately jumped up and got off my cock explaining how much it hurt.. I was still super turned on so I asked him to fuck me instead with the same results.. He got it in me and I jumped up and off him too with the pain of it.. so I did get my first cock in me raw. fast forward 25 years, still fantasizing about getting fucked I meet a guy online and we get together and start to suck each other a few times. After a few meetings I admit that I have always wanted to get fucked. to feel a mans cock in me and know he is getting off. Well he is more than happy to help out but insists on condoms, so I agree and I have to admit it did hurt when he put his cock in me but it was over with pretty quick, we started a regular thing at least a couple times a month we would get together and suck, then he would condom up and fuck me. (it never didn't hurt). One day we we got together at my place and we sucking each other I was rimming him a little, this really seemed to turn him on, next thing I know he has me on my back with my legs over his shoulders and I can feel his raw cock poking at my hole.. He starts to penetrate me and I make a little face with the feeling of a dry cock going in me.. he pulls back and lubes me with his spit and immediately puts his cock back on my hole and starts pushing in me. I feel myself open to his cock then feel his balls on my ass.. He looks down at me and asks how it feels, its at this point I realize he is in me raw and it doesn't hurt.. It feels good, I tell him this and he starts to move in and out of me. I am amazed at how good his cock feels going in and out of me. After a minute or so he looks down at me again and asks me if he can cum in me, without hesitation I say yes and with that he closes his eyes and starts to moan, I can feel his cock throb in me and then the warmth of his cum as it flows into me. I was hooked! I had a man in me with no condom, I was in awe of how good it felt and I had the intimacy of a man cumming in me.
I have never gone back to condoms since.
I know this is more like two separate stories, but in my mind I always wanted that feeling of intimacy of a mans bare cock in me since that first penetration..