Accidental anal (m/f) | 2016

I've been with my girl for more than ten years and had always been disappointed at her unwillingness to take my cock in her ass. I've always been an ass enthusiast and hers is a particularly lovely, big round firm one with a cute rosebud so you can imagine my disappointment. It was an ass that needed my cock in it.

The most I was allowed to do was rub my cock against her rosebud a little to get myself excited before fucking her pussy.

One night we were playing with massages and I was enjoying the view of her on her stomach with that amazing ass tempting me. As I applied more and more massage oil, I cheekily let some ooze between her ass cheeks each time. I saw her move her ass a little as the oil dribbled onto her rosebud but she said nothing; obviously enjoying having her back, neck and shoulders massaged.

I alternated between rubbing oil into her back, and massaging her neck and shoulders while cheekily also rubbing my cock between her ass cheeks. I'd been sneakily oiling my cock as well while oiling my hands so it was gliding between her cheeks nicely.

Usually when we did massages I would get to the point where I couldn't take any more and would enter her from behind. Not in the forbidden holy grail of her asshole but at least I could see the view from behind and rub her clit while I did.

So, this night, having reached the point of no more self control, I continued to massage her shoulders while pressing my cock into her warm, slippery vagina. Heavenly.

I reached around to tickle her clitoris...hmm. That's further away than I was expecting. My cock is definitely in...what's going on here? I investigate a little more with my fingers and find her pussy...and my cock isn't in it.

Holy shit. Am I in her ass? I am in her ass.

"Am I...umm...am I.."

Her smile tells me that I am. Is this okay? Am I hurting you? Yes it ok and no it feels fine.

Holy shit. I first tried to fuck a girl in the ass at 18 and had to stop as it was too painful for her. Two previous attempts with the same girl failed, too painful. Yet here I am up to my balls in that sweet little butthole.

I pull out just to have the pleasure of feeling my cock push it's way through her rosebud and into her tight anal passage. Mmhmm that feels damn good.

I start fucking her ass with long, deep strokes. I know she won't orgasm this way and that's disappointing but she's enjoying the closeness and the look on her face while my cock is buried in her asshole tells me her dirty side is enjoying this.

It's not long before I explode in her ass and deliver my sticky load direct to her bowels. Mmmmm. Wow.

I'm not sure it felt better than pussy, although it was nice and tight. The real pleasure is in knowing it's such a dirty deed. And after so many years of wishing and trying...wow.

Never lose hope :) use lots of lube, and make her feel safe, relaxed and loved.

Comments and PMs welcome as it's my first sex story!