At the time, this particular gf was a complete freak compared to me. I was still getting over some repression, but she knew what she wanted and wanted it all the time. She had brought up anal before but I was kind of hesitant. Between sanitary issues and potentially irrational fears of damage to her asshole, I was very against it. She was obsessed tho, she would beg me to fuck her in the ass. I did what I could to ease myself into it. I started teasing the edge of her asshole with my finger while I ate her out or fucked her. Then I got comfortable enough to be a knuckle or two deep. Until I got to the point that I'd have nearly a whole finger massaging the inside of her ass anytime we fucked. I thought that would be my limit.

One night I figured if I'm comfortable using a finger, then a toy should be absolutely no issue. We used toys fairly often. She had a pink vibrator, roughly the same size of my cock, that was her favorite. I would normally alternate teasing her clit and shoving it in her mouth as I fucked her. This time after pulling the vibrator out of her mouth, I massaged it around her ass and asked if she'd like it here. She groaned out a begging yes. I brought it back to her mouth and told her to get it ready then. She gorged herself on the vibrator, taking it down her throat till she gagged and covered it with drool.

As soon as I pressed the vibrator against her asshole I could feel gentle vibrations. Once it was all the way in I couldnt move. Her pussy was vibrating around my cock making it feel like I was having constant micro orgasms. After adjusting to it, I started fucking her wildly. This woman had a famously wet pussy but she outdid herself that night. Our thighs and stomachs were slick with her juices. I flipped her over doggy style so I could control the vibrator better and enjoy the view. Normally, I could tell when she orgasmed everytime. Her moans would raise in pitch and her pussy would clamp down around my cock like nothing I've experienced since. This time her pussy was convulsing so much and her moans were so aggressive I had no idea. I was intoxicated by her moans and the feeling of her pussy vibrating. I came harder and deeper in her than I ever may again.

After how enthusiastic she was about that experience she finally convinced me to fuck her in the ass, the next time we got to it. This time I used the vibrator in her pussy while I fucked her in the ass. She loved it even more than the other way around. I fucked her ass with everything I had and left her a breathless, leg twitching mess. Unfortunately, it wasnt for me. Feeling the vibrator through her helped me cum, just barely. Its a novel experience and if I have a future partner that really really wants me to fuck them in the ass, then I would. That's gonna have to be a special occassion thing tho.