This was a long time ago, but the memory remains fresh as I often remember it as the day we turned kinky. I was 26 (M) and she was 24 (F), newly in a relationship and loved fucking. But I’m not a fan of blood, so fucking on her period was a no no for me. But she was extra horny, and we never used condoms. Both tested and she was on the pill. She proposed anal, I was a mild germaphobe and asked if we could start in the shower. She agreed, but also surprised by saying I’ve been eating extra fiber and cleaning her tummy well to prepare for it. That made me so hard, we made out in the living room and smoke a j as a pre fucking ritual. I would normally not go down on her during her period, but in the shower I had zero hesitation licking her clit and finger fucking her. She had lube on her, and I used it to finger her asshole as i ate her. She really seemed to enjoy the new sensation.

I don’t know how long I stretched her ass with a few fingers, before moving to a butt plug. We had used these before. I started lubing her up, and fucking her asshole with the plug. She got used to that smooth metal. But when we tried my cock. She froze up and it wouldn’t go in. We decided to go back to the bed since the risk of falling was big in the slippery shower.

In the bedroom, I started with the toy, making out. I had read only that she needs to relax and not be worried. I told her that I wanted her to relax, and not be worried. I kissed her and calmed her but foreplay and jokes. She quickly got ready after and said please try now. And it didn’t take long for my lubed up cock to start entering. She was in mild pain, I stopped and reminded her, that I don’t wanna hurt her or want her to not enjoy the first time. She started to breathe again and slowly accepted my cock. I hugged her and started with very slow movements, asking her at every step how she was doing. And making sure she was not uncomfortable. Not long after I was literally fucking her asshole. Her moans were so loud. She asked me to go hard by the end, but I had already cum a few times considering her asshole was so tight. I really fucked her fast and balls deep, before cummimg deep in her ass.

The best part was next day, when she couldn’t walk straight. I was like shit did I hurt you, she almost sarcastically said “are you serious? You fucked the shit out of my asshole!”. Dhe explained that she loves pain, but wanted someone who she could trust to not hurt her asshole. Be a douche, but once her asshole was relaxed and she started enjoying it, the pain was a bonus. That’s when I realized even my average but thick cock can cause serious pain when used correctly. And I realized I’ve done the same to get pussy, but that she could take like a champ!

We got kinker and wilder after that