First orgasm, first time anal [M/F] | 2016

I dated my former partner for just over 2 years. Let's call her Maria. When we first got together she confided in me that she had never had an orgasm. I was really head over heels for her, so obviously I was hoping we could change that. The first month or so into the relationship we were having lots of sex, but still no orgasm for her.

I was already into anal because another former gf and I used to do a bit of anal. It was and still is a big fetish of mine. I'm an anal top and love it. So I suggest to Maria that we try anal. She said she tried it with her ex once, but it wasn't great. I assure her that we'll take it slow with lots of foreplay and lube and maybe it will help her orgasm.

Maria is a beautiful, petite blond with a very sexy round ass. I was (and still am) very physically attracted to her. So, the first time we are gong to try anal I begin by going down on her. I get her nice and wet. While I'm down there I start to gently rub her asshole, using her own glorious pussy juices to softly press against her pursed anus. By this time she is really wet and horny. The basic taboo of it all is a huge turn on. It's new territory and super hot.

I get out some lube and get my fingers lubed up good. I start to gently enter her asshole with one of my fingers. Just a bit to start, working my way up to the entire finger. We take our time. She is really getting into it. After a while I start to insert two fingers, then three. So, eventually I'm finger-fucking her very tight asshole with three fingers and she is really going crazy. This is when I start to lube my cock up. I'm rock hard by this point. I don't have a very long cock, it's 6.5 inches, but it's quite thick.

She is on her stomach, ass slightly upturned toward me. I straddle her and slowly ease the head of my cock insid her ass. We are both absolute lunatics at this point because it's so hot. Eventually, after some slow easing in, I eventually get my full cock deep in her asshole. At this point I have her luscious, round ass in my hands and I've fully mounter her and I'm doing a slow pump in and out of her tight hole. Her pussy is dripping all over. Her ass is really lubed, she's loving it, so I say: "I'm really going to fuck your ass now. I'm gonna fucking pump your hole full of cock." She is yelling at me to fuck her hard at this point. I start really giving it to her, pumping the hell out of her asshole. It's super wet and hot, wrapped tightly around my thick throbbing cock. I grab her pony tail and bang her harder. It didn't take long and she tightens up and lets out a guttural yell.

For the first time in her life, she cums. With so much excitement as she tightens up (and I'm already on the verge anyway) I squirt a huge load into her asshole, pumping her full of hot cum. Just thinking about it again gets me rock hard.

Anyway, she absolutely loved anal after that. All she wanted was anal becaue it got her off every time. I was really spoiled. For two years straight all I did was continually fuck her beatufiul ass.