OK, this is my story about the first time I did a chick in the ass...
I had been going out with a girl, we'll call her Marie, for about 3 years. We'd had some wild sex the whole time, humping like rabbits, witih lots of oral too. Early on, I got her into a little ass play. I was pretty drunk on some beers, and always wanted to eat out a girl's ass. So we were 69ing (one of her favorites) and I just figured "fuck it" and took a couple quick tentative licks of her asshole, thinking that if she objected I'd just blame it on the alcohol. But, she didn't object, if anything she angled her butt so her asshole was right on my mouth. Knowing I had the green light I went to town on her ass, licking all around her browneye. I tried sticking my tongue in her anus, but it was still a bit too tight. I had my 2 big fingers in her twat, with my thumb working her clit, so I took my index finger out of her box and slowly slid it up her well-lubricated ass. She let out a loud moan, and her shithole was so tight that it was cutting of the circulation off to my finger, it was turning numb. I took it out to get the feeling back, licked it to get it lubed up again, and stuck it back in. I still had my middle finger in her pussy, and I started working them both in and out. Her heavy breathing, and the intensity that she starting sucking on my cock, told me she loved it. After a little bit of that, I started working the middle finger in, jamming 2 fingers up her tight pooper. She screamed "oh, God yes", and really started going down on my hard cock, I could feel my balls tapping on her chin. I started pulling my fingers all the way out and jamming them back in. After a bit of this I could see that her anus has a nice gape to it, so I took my fingers out and jammed my tongue straight up her ass while my thumb kept working the clit. Marie couldn't handle this, she stopped sucking my dick and just started screaming and moaning. I didn't take long until she had a gigantic orgasm, squirting a couple pints of pussy juice all over my face. Normally she'd hit me with a couple shots of juice, but this was like someone pouring a bottle of hot tasty pussy water all over my face.
We continued like that for a couple of years, but the anal fingering and licking was only part of the foreplay. I wanted do fuck her in the ass, but never had the courage to ask. I knew that I'd only get one chance, if she said "no", I knew it'd be "no" for life. And I cared for her deeply, so just randomly shoving up her ass wasn't an option.
Then, one night, I was doing her doggie-style, while I was wigging my thumb around in her asshole. She and I were pretty trashed on some Grey Goose (when I drink liquor I only go top shelf), and I thought this would be my best shot. I knew if I could get it in there once I could do it every time we fucked. I pulled my dick out and laid it in her crack, and said "hey". She looked back at me, and I said "Can I stick it in here?" while I ass-fucked her with my thumb. Without hesitation she nodded, and I'm wondering why I waited so long to do this. I took my thumb out of her ass and lined my dick up with her tight shitter. I slowly pushed it up there, and it was the sexiest thing I'd ever seen. She was still looking back at me, and I could see a little bit of pain on her face. I had about 2 inches in and I asked if she was OK. She told me to just hold where I was while she got used to it. After a minute or 2 she pushed her ass back on my cock. Another inch went in and she let out a really loud moan and said "OK, go slow". I pushed in about an inch, pulled out a little, pushed in another inch, and kept repeating the process until I was balls-deep.
I slowly pulled out and pushed it back in, working a little more in and out until she was taking the whole shaft with each thrust. I started getting a good rhythm going, even pulling it out and popping it back it in. I was giving it to Marie good, and she was LOUDLY moaning and panting. Just as I was about to bust my nut she screamed "It feels so good!". Sexiest thing I've ever heard, that was enough to send me over the edge and I blew a huge load into her ass. When she felt my cum hitting the inside of her ass, she started yelling "Oh God, it's so fucking hot, I can fell your cum up my ass and I love it! I want More! MORE!" I didn't disappoint, blowing by far and away the biggest load I ever blew, I felt like I was cumming for a good solid 2 minutes. I started to pull out, but she said "No, leave it in, I want it again". It didn't take long till I was hard again, and this time I gave it to her while we were both lying on our sides. Having just came, this time I banged that ass for over a half hour, and she had so many orgasms that I lost count.
I did her in the ass pretty much every night after that. The best thing was that Marie had no problem doing ass-to-mouth. Hell, it was her idea, one night she was on top with it in her ass, and out of nowhere she just hops off, starts blowing me, and just hops back on. After that it became a regular thing. And she really loved it when I came in her ass. Even when we were just having regular vaginal sex, I'd always warn her that I was about to bust, and she'd grab my dick and stick it up her ass to feel that hot load in her rectum. Me and Marie broke up about a year ago, but I still have the memories. Every once in a while I go on the tube sites and find a girl that looks like her so I can kind of re-live the experiences.