As me and my wife Jenny got more into this kink and she got comfortable with the idea that I'd listen and not judge her, and in fact was turned on and ecstatic that she told me these stories, I got more details that got left out in earlier stories.

A big one was this guy she hooked up with shortly after a breakup with a long term boyfriend. She had met him online while very sad about this relationship ending. He lived a few cities over and got her a train ticket to come see him. She was somewhere around 18-19, he was in his late 20s.

He got her very drunk when she arrived. She's a major lightweight, she weighs like 100 lbs and it really only takes 2 drinks before her balance is compromised. He fucked her raw and came inside her, something she would basically never let a guy do normally.

I already thought this story was insanely hot, though it was something she was really ashamed of and reluctant to tell me. BUT, there was a major detail she left out of that first telling of the story.

The first time i fucked her ass she ended up loving it. I was pretty experienced with anal, Id gone through the "trial and error" phase of learning how to introduce it comfortably with a past girlfriend. She was really surprised at how much she enjoyed it, she actually cums harder when I'm in her ass than her pussy. Having her clit rubbed while getting her ass fucked is basically the ultimate orgasm to her. She even went as far as telling some of her friends they shouldn't think of anal as automatically off limits, one friend of ours actually let her boyfriend try it because of Jennys encouragement

When I asked her if she'd tried it before, she told me her ex had wanted to fuck her ass, but he didn't know what he was doing. The one time he got it in he basically shoved his whole cock in one push and it was insanely painful, she immediately pulled away and she didn't let him try again.

I was very proud, believing myself to be the first guy to fuck her ass, and also getting her to love it. We still do anal regularly to this day after being together for 10 years, if I go too long without fucking her ass she'll actually get sad lol.

But, my pride at being the first in her ass was struck down. One night during foreplay while I asked her to tell me details about the guy she took the train to see, she admitted to me that he had actually been the first one to fuck her ass. She was so drunk that she didn't protest at all. He just pulled straight out of her pussy and slid his cock into her ass, no lube or warm up.

She just took it without protesting. She was far away from home in a strange man's house, drunk and disoriented, so she just let him do what he wanted. The alcohol dulled the discomfort and probably helped her relax. This guy then started switching back and forth between her pussy and ass, which is something you really shouldn't do to a girl, and I'm sure he knew that. He was just treating her like a whore he could do anything she wanted with, and she took it.

Her memories of that night are such a blur that actually does not know which hole he ended up cumming in. He may have been the first man to cum inside her ass. But regardless, now I knew I wasn't the first to fuck her ass. I had 3 long term girlfriends before her. With the first, I took her virginity. With the two after that I had been the first one to fuck their ass.

With Jenny though, the girl I love most in the world, I was not the first to anything. All of her holes had been used by other men before me. She had been afraid to tell me before because she had still thought of anal as something scary and unpleasant, and she felt humiliated by the fact that she'd let this man do it to her.

Luckily I was able to change her opinion and she found out something new she enjoyed sexually. I can't wait to cum in her ass again tonight lol